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Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
. It is an
alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...
with the
chemical formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...
. Its formula can be also written as or (an
ethyl group In organic chemistry, an ethyl group (abbr. Et) is an alkyl substituent with the formula , derived from ethane (). ''Ethyl'' is used in the International Union of Pure and Applied Chemistry's nomenclature of organic chemistry for a saturated ...
linked to a
hydroxyl group In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy g ...
). Ethanol is a volatile,
flammable A combustible material is something that can burn (i.e., ''combust'') in air. A combustible material is flammable if it ignites easily at ambient temperatures. In other words, a combustible material ignites with some effort and a flammable mat ...
, colorless liquid with a characteristic wine-like odor and pungent taste. It is a
psychoactive A psychoactive drug, psychopharmaceutical, psychoactive agent or psychotropic drug is a chemical substance, that changes functions of the nervous system, and results in alterations in perception, mood, consciousness, cognition or behavior. Th ...
recreational drug Recreational drug use indicates the use of one or more psychoactive drugs to induce an altered state of consciousness either for pleasure or for some other casual purpose or pastime by modifying the perceptions and emotions of the user. When a ...
, the active ingredient in
alcoholic drink An alcoholic beverage (also called an alcoholic drink, adult beverage, or a drink) is a drink that contains ethanol, a type of alcohol that acts as a drug and is produced by fermentation of grains, fruits, or other sources of sugar. The c ...
s. Ethanol is naturally produced by the
fermentation Fermentation is a metabolic process that produces chemical changes in organic substrates through the action of enzymes. In biochemistry, it is narrowly defined as the extraction of energy from carbohydrates in the absence of oxygen. In food ...
process of
sugar Sugar is the generic name for sweet-tasting, soluble carbohydrates, many of which are used in food. Simple sugars, also called monosaccharides, include glucose, fructose, and galactose. Compound sugars, also called disaccharides or double ...
s by
yeast Yeasts are eukaryotic, single-celled microorganisms classified as members of the fungus kingdom. The first yeast originated hundreds of millions of years ago, and at least 1,500 species are currently recognized. They are estimated to constitut ...
s or via
petrochemical Petrochemicals (sometimes abbreviated as petchems) are the chemical products obtained from petroleum by refining. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sou ...
processes such as
ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene i ...
hydration. It has medical applications as an
antiseptic An antiseptic (from Greek ἀντί ''anti'', "against" and σηπτικός ''sēptikos'', "putrefactive") is an antimicrobial substance or compound that is applied to living tissue/skin to reduce the possibility of infection, sepsis, or putre ...
and
disinfectant A disinfectant is a chemical substance or compound used to inactivate or destroy microorganisms on inert surfaces. Disinfection does not necessarily kill all microorganisms, especially resistant bacterial spores; it is less effective than st ...
. It is used as a chemical
solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...
and in the
synthesis Synthesis or synthesize may refer to: Science Chemistry and biochemistry *Chemical synthesis, the execution of chemical reactions to form a more complex molecule from chemical precursors ** Organic synthesis, the chemical synthesis of organ ...
of
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
s, and as a fuel source. Ethanol also can be dehydrated to make ethylene, an important chemical feedstock. As of 2006, world production of ethanol was , coming mostly from Brazil and the U.S.


Etymology

''Ethanol'' is the
systematic name A systematic name is a name given in a systematic way to one unique group, organism, object or chemical substance, out of a specific population or collection. Systematic names are usually part of a nomenclature. A semisystematic name or semitrivial ...
defined A definition is a statement of the meaning of a term (a word, phrase, or other set of symbols). Definitions can be classified into two large categories: intensional definitions (which try to give the sense of a term), and extensional defini ...
by the
International Union of Pure and Applied Chemistry The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...
for a compound consisting of an
alkyl group In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl is derived from a cycloalk ...
with two carbon
atom Every atom is composed of a nucleus and one or more electrons bound to the nucleus. The nucleus is made of one or more protons and a number of neutrons. Only the most common variety of hydrogen has no neutrons. Every solid, liquid, gas, and ...
s (prefix "eth-"), having a single bond between them (infix "-an-") and an attached
functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...
−OH group (suffix "-ol"). The "eth-" prefix and the qualifier "ethyl" in "ethyl alcohol" originally come from the name "ethyl" assigned in 1834 to the group − by
Justus Liebig Justus Freiherr von Liebig (12 May 1803 – 20 April 1873) was a German scientist who made major contributions to agricultural and biological chemistry, and is considered one of the principal founders of organic chemistry. As a professor at th ...
. He coined the word from the
German German(s) may refer to: * Germany (of or related to) **Germania (historical use) * Germans, citizens of Germany, people of German ancestry, or native speakers of the German language ** For citizens of Germany, see also German nationality law **Ger ...
name ''Aether'' of the compound −O− (commonly called "ether" in
English English usually refers to: * English language * English people English may also refer to: Peoples, culture, and language * ''English'', an adjective for something of, from, or related to England ** English national ide ...
, more specifically called "
diethyl ether Diethyl ether, or simply ether, is an organic compound in the ether class with the formula , sometimes abbreviated as (see Pseudoelement symbols). It is a colourless, highly volatile, sweet-smelling ("ethereal odour"), extremely flammable liq ...
"). According to the ''
Oxford English Dictionary The ''Oxford English Dictionary'' (''OED'') is the first and foundational historical dictionary of the English language, published by Oxford University Press (OUP). It traces the historical development of the English language, providing a com ...
'', ''Ethyl'' is a contraction of the Ancient Greek αἰθήρ (', "upper air") and the Greek word ὕλη (', "substance"). The name ''ethanol'' was coined as a result of a resolution on naming alcohols and phenols that was adopted at the International Conference on Chemical Nomenclature that was held in April 1892 in Geneva, Switzerland. The term ''alcohol'' now refers to a wider class of substances in chemistry nomenclature, but in common parlance it remains the name of ethanol. It is a medieval loan from
Arabic Arabic (, ' ; , ' or ) is a Semitic languages, Semitic language spoken primarily across the Arab world.Semitic languages: an international handbook / edited by Stefan Weninger; in collaboration with Geoffrey Khan, Michael P. Streck, Janet C ...
'' al-kuḥl'', a powdered ore of antimony used since antiquity as a cosmetic, and retained that meaning in
Middle Latin Medieval Latin was the form of Literary Latin used in Roman Catholic Church, Roman Catholic Western Europe during the Middle Ages. In this region it served as the primary written language, though local languages were also written to varying deg ...
. The use of 'alcohol' for ethanol (in full, "alcohol of wine") is modern and was first recorded in 1753. Before the late 18th century the term "alcohol" generally referred to any sublimated substance.


Uses


Medical


Antiseptic

Ethanol is used in medical wipes and most commonly in antibacterial
hand sanitizer Hand sanitizer (also known as hand antiseptic, hand disinfectant, hand rub, or handrub) is a liquid, gel or foam generally used to kill many viruses/bacteria/microorganisms on the hands. In most settings, hand washing with soap and water is ge ...
gels as an
antiseptic An antiseptic (from Greek ἀντί ''anti'', "against" and σηπτικός ''sēptikos'', "putrefactive") is an antimicrobial substance or compound that is applied to living tissue/skin to reduce the possibility of infection, sepsis, or putre ...
for its bactericidal and anti-fungal effects. Ethanol kills
microorganism A microorganism, or microbe,, ''mikros'', "small") and ''organism'' from the el, ὀργανισμός, ''organismós'', "organism"). It is usually written as a single word but is sometimes hyphenated (''micro-organism''), especially in olde ...
s by dissolving their membrane
lipid bilayer The lipid bilayer (or phospholipid bilayer) is a thin polar membrane made of two layers of lipid molecules. These membranes are flat sheets that form a continuous barrier around all cells. The cell membranes of almost all organisms and many vir ...
and denaturing their
protein Proteins are large biomolecules and macromolecules that comprise one or more long chains of amino acid residues. Proteins perform a vast array of functions within organisms, including catalysing metabolic reactions, DNA replication, respo ...
s, and is effective against most
bacteria Bacteria (; singular: bacterium) are ubiquitous, mostly free-living organisms often consisting of one biological cell. They constitute a large domain of prokaryotic microorganisms. Typically a few micrometres in length, bacteria were among ...
,
fungi A fungus ( : fungi or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and molds, as well as the more familiar mushrooms. These organisms are classified as a kingdom, separately from ...
and
virus A virus is a submicroscopic infectious agent that replicates only inside the living cells of an organism. Viruses infect all life forms, from animals and plants to microorganisms, including bacteria and archaea. Since Dmitri Ivanovsky's 1 ...
es. However, it is ineffective against bacterial
spores In biology, a spore is a unit of sexual or asexual reproduction that may be adapted for dispersal and for survival, often for extended periods of time, in unfavourable conditions. Spores form part of the life cycles of many plants, algae, f ...
, but that can be alleviated by using
hydrogen peroxide Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscous than water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution (3% ...
. A solution of 70% ethanol is more effective than pure ethanol because ethanol relies on water molecules for optimal antimicrobial activity. Absolute ethanol may inactivate microbes without destroying them because the alcohol is unable to fully permeate the microbe's membrane. Ethanol can also be used as a disinfectant and antiseptic because it causes cell dehydration by disrupting the osmotic balance across the cell membrane, so water leaves the cell leading to cell death.


Antidote

Ethanol may be administered as an
antidote An antidote is a substance that can counteract a form of poisoning. The term ultimately derives from the Greek term φάρμακον ἀντίδοτον ''(pharmakon) antidoton'', "(medicine) given as a remedy". Antidotes for anticoagulants are s ...
to
ethylene glycol poisoning Ethylene glycol poisoning is poisoning caused by drinking ethylene glycol. Early symptoms include Substance intoxication, intoxication, vomiting and abdominal pain. Later symptoms may include a decreased level of consciousness, headache, and seiz ...
and
methanol poisoning Methanol toxicity (also ''methanol poisoning'') is poisoning from methanol, characteristically via ingestion. Symptoms may include a decreased level of consciousness, poor or no coordination, hypothermia, vomiting, abdominal pain, and a specific s ...
. Ethanol serves this process by acting as a
competitive inhibitor Competitive inhibition is interruption of a chemical pathway owing to one chemical substance inhibiting the effect of another by competing with it for binding or bonding. Any metabolic or chemical messenger system can potentially be affected b ...
against
methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a ...
and
ethylene glycol Ethylene glycol (IUPAC name: ethane-1,2-diol) is an organic compound (a vicinal diol) with the formula . It is mainly used for two purposes, as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odo ...
for
alcohol dehydrogenase Alcohol dehydrogenases (ADH) () are a group of dehydrogenase enzymes that occur in many organisms and facilitate the interconversion between alcohols and aldehydes or ketones with the reduction of nicotinamide adenine dinucleotide (NAD+) to N ...
. Though it has more side effects, ethanol is less expensive and more readily available than
fomepizole Fomepizole, also known as 4-methylpyrazole, is a medication used to treat methanol poisoning, methanol and ethylene glycol poisoning. It may be used alone or together with hemodialysis. It is given by intravenous, injection into a vein. Common ...
, which is also used as an antidote for methanol and ethylene glycol poisoning.


Medicinal solvent

Ethanol, often in high concentrations, is used to dissolve many water-insoluble medications and related compounds. Liquid preparations of
pain medications An analgesic drug, also called simply an analgesic (American English), analgaesic (British English), pain reliever, or painkiller, is any member of the group of drugs used to achieve relief from pain (that is, analgesia or pain management). It ...
, cough and cold medicines, and mouth washes, for example, may contain up to 25% ethanol and may need to be avoided in individuals with adverse reactions to ethanol such as
alcohol-induced respiratory reactions Alcohol-induced respiratory reactions, also termed alcohol-induced asthma and alcohol-induced respiratory symptoms, are increasingly recognized as a pathological bronchoconstriction response to the consumption of alcohol that afflicts many people ...
. Ethanol is present mainly as an antimicrobial preservative in over 700 liquid preparations of medicine including
acetaminophen Paracetamol, also known as acetaminophen, is a medication used to treat fever and mild to moderate pain. Common brand names include Tylenol and Panadol. At a standard dose, paracetamol only slightly decreases body temperature; it is inferior ...
,
iron supplement Iron supplements, also known as iron salts and iron pills, are a number of iron formulations used to treat and prevent iron deficiency including iron deficiency anemia. For prevention they are only recommended in those with poor absorption, h ...
s,
ranitidine Ranitidine, sold under the brand name Zantac among others, is a medication used to decrease stomach acid production. It is commonly used in treatment of peptic ulcer disease, gastroesophageal reflux disease, and Zollinger–Ellison syndrome. I ...
,
furosemide Furosemide is a loop diuretic medication used to treat fluid build-up due to heart failure, liver scarring, or kidney disease. It may also be used for the treatment of high blood pressure. It can be taken by injection into a vein or by mouth ...
,
mannitol Mannitol is a type of sugar alcohol used as a sweetener and medication. It is used as a low calorie sweetener as it is poorly absorbed by the intestines. As a medication, it is used to decrease pressure in the eyes, as in glaucoma, and to lower ...
,
phenobarbital Phenobarbital, also known as phenobarbitone or phenobarb, sold under the brand name Luminal among others, is a medication of the barbiturate type. It is recommended by the World Health Organization (WHO) for the treatment of certain types of ep ...
,
trimethoprim/sulfamethoxazole Trimethoprim/sulfamethoxazole, sold under the brand name Bactrim among others, is a fixed-dose combination antibiotic medication used to treat a variety of bacterial infections. It consists of one part trimethoprim to five parts sulfamethoxazo ...
and
over-the-counter Over-the-counter (OTC) drugs are medicines sold directly to a consumer without a requirement for a prescription from a healthcare professional, as opposed to prescription drugs, which may be supplied only to consumers possessing a valid prescr ...
cough medicine Cold medicines are a group of medications taken individually or in combination as a treatment for the symptoms of the common cold and similar conditions of the upper respiratory tract. The term encompasses a broad array of drugs, including a ...
.


Pharmacology

In mammals, ethanol is primarily metabolized in the liver and stomach by
alcohol dehydrogenase Alcohol dehydrogenases (ADH) () are a group of dehydrogenase enzymes that occur in many organisms and facilitate the interconversion between alcohols and aldehydes or ketones with the reduction of nicotinamide adenine dinucleotide (NAD+) to N ...
(ADH) enzymes. These enzymes catalyze the
oxidation Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a d ...
of ethanol into
acetaldehyde Acetaldehyde (IUPAC systematic name ethanal) is an organic chemical compound with the formula CH3 CHO, sometimes abbreviated by chemists as MeCHO (Me = methyl). It is a colorless liquid or gas, boiling near room temperature. It is one of the mos ...
(ethanal): :CH3CH2OH + NAD+ → CH3CHO +
NADH Nicotinamide adenine dinucleotide (NAD) is a coenzyme central to metabolism. Found in all living cells, NAD is called a dinucleotide because it consists of two nucleotides joined through their phosphate groups. One nucleotide contains an aden ...
+ H+ When present in significant concentrations, this metabolism of ethanol is additionally aided by the
cytochrome P450 Cytochromes P450 (CYPs) are a Protein superfamily, superfamily of enzymes containing heme as a cofactor (biochemistry), cofactor that functions as monooxygenases. In mammals, these proteins oxidize steroids, fatty acids, and xenobiotics, and are ...
enzyme
CYP2E1 Cytochrome P450 2E1 (abbreviated CYP2E1, ) is a member of the cytochrome P450 mixed-function oxidase system, which is involved in the metabolism of xenobiotics in the body. This class of enzymes is divided up into a number of subcategories, includ ...
in humans, while trace amounts are also metabolized by
catalase Catalase is a common enzyme found in nearly all living organisms exposed to oxygen (such as bacteria, plants, and animals) which catalyzes the decomposition of hydrogen peroxide to water and oxygen. It is a very important enzyme in protecting t ...
. The resulting intermediate, acetaldehyde, is a known carcinogen, and poses significantly greater toxicity in humans than ethanol itself. Many of the symptoms typically associated with alcohol intoxication—as well as many of the health hazards typically associated with the long-term consumption of ethanol—can be attributed to acetaldehyde toxicity in humans. The subsequent oxidation of acetaldehyde into acetate is performed by
aldehyde dehydrogenase Aldehyde dehydrogenases () are a group of enzymes that catalyse the oxidation of aldehydes. They convert aldehydes (R–C(=O)) to carboxylic acids (R–C(=O)). The oxygen comes from a water molecule. To date, nineteen ALDH genes have be ...
(ALDH) enzymes. A mutation in the ALDH2 gene that encodes for an inactive or dysfunctional form of this enzyme affects roughly 50% of east Asian populations, contributing to the characteristic
alcohol flush reaction Alcohol flush reaction is a condition in which a person develops flushes or blotches associated with erythema on the face, neck, shoulders, and in some cases, the entire body after consuming alcoholic beverages. The reaction is the result of an ac ...
that can cause temporary reddening of the skin as well as a number of related, and often unpleasant, symptoms of acetaldehyde toxicity. This mutation is typically accompanied by another mutation in the
alcohol dehydrogenase Alcohol dehydrogenases (ADH) () are a group of dehydrogenase enzymes that occur in many organisms and facilitate the interconversion between alcohols and aldehydes or ketones with the reduction of nicotinamide adenine dinucleotide (NAD+) to N ...
enzyme
ADH1B Alcohol dehydrogenase 1B is an enzyme that in humans is encoded by the ''ADH1B'' gene. The protein encoded by this gene is a member of the alcohol dehydrogenase family. Members of this enzyme family metabolize a wide variety of substrates, includ ...
in roughly 80% of east Asians, which improves the catalytic efficiency of converting ethanol into acetaldehyde.


Recreational

As a
central nervous system The central nervous system (CNS) is the part of the nervous system consisting primarily of the brain and spinal cord. The CNS is so named because the brain integrates the received information and coordinates and influences the activity of all par ...
depressant A depressant, or central depressant, is a drug that lowers neurotransmission levels, which is to depress or reduce arousal or stimulation, in various areas of the brain. Depressants are also colloquially referred to as downers as they lower the ...
, ethanol is one of the most commonly consumed
psychoactive drug A psychoactive drug, psychopharmaceutical, psychoactive agent or psychotropic drug is a chemical substance, that changes functions of the nervous system, and results in alterations in perception, mood, consciousness, cognition or behavior. ...
s. Despite alcohol's psychoactive and
carcinogenic A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive substan ...
properties, it is readily available and legal for sale in most countries. However, there are laws regulating the sale, exportation/importation, taxation, manufacturing, consumption, and possession of alcoholic beverages. The most common regulation is prohibition for minors.


Fuel


Engine fuel

The largest single use of ethanol is as an engine
fuel A fuel is any material that can be made to react with other substances so that it releases energy as thermal energy or to be used for work. The concept was originally applied solely to those materials capable of releasing chemical energy but ...
and
fuel additive Petrol additives increase petrol's octane rating or act as corrosion inhibitors or lubricants, thus allowing the use of higher compression ratios for greater efficiency and power. Types of additives include metal deactivators, corrosion inhib ...
.
Brazil Brazil ( pt, Brasil; ), officially the Federative Republic of Brazil (Portuguese: ), is the largest country in both South America and Latin America. At and with over 217 million people, Brazil is the world's fifth-largest country by area ...
in particular relies heavily upon the use of ethanol as an engine fuel, due in part to its role as one of the world's leading producers of ethanol.
Gasoline Gasoline (; ) or petrol (; ) (see ) is a transparent, petroleum-derived flammable liquid that is used primarily as a fuel in most spark-ignited internal combustion engines (also known as petrol engines). It consists mostly of organic co ...
sold in Brazil contains at least 25%
anhydrous A substance is anhydrous if it contains no water. Many processes in chemistry can be impeded by the presence of water; therefore, it is important that water-free reagents and techniques are used. In practice, however, it is very difficult to achie ...
ethanol. Hydrous ethanol (about 95% ethanol and 5% water) can be used as fuel in more than 90% of new gasoline-fueled cars sold in the country. The US and many other countries primarily use E10 (10% ethanol, sometimes known as gasohol) and E85 (85% ethanol) ethanol/gasoline mixtures. Over time, it is believed that a material portion of the ≈ per year market for gasoline will begin to be replaced with fuel ethanol. Australian law limits the use of pure ethanol from sugarcane waste to 10% in automobiles. Older cars (and vintage cars designed to use a slower burning fuel) should have the engine valves upgraded or replaced. According to an industry
advocacy group Advocacy groups, also known as interest groups, special interest groups, lobbying groups or pressure groups use various forms of advocacy in order to influence public opinion and ultimately policy. They play an important role in the developm ...
, ethanol as a fuel reduces harmful
tailpipe emissions Exhaust gas or flue gas is emitted as a result of the combustion of fuels such as natural gas, gasoline (petrol), diesel fuel, fuel oil, biodiesel blends, or coal. According to the type of engine, it is discharged into the atmosphere through an ...
of carbon monoxide, particulate matter,
oxides of nitrogen Nitrogen oxide may refer to a binary compound of oxygen and nitrogen, or a mixture of such compounds: Charge-neutral *Nitric oxide (NO), nitrogen(II) oxide, or nitrogen monoxide *Nitrogen dioxide (), nitrogen(IV) oxide *Nitrogen trioxide (), or ni ...
, and other ozone-forming pollutants.
Argonne National Laboratory Argonne National Laboratory is a science and engineering research United States Department of Energy National Labs, national laboratory operated by University of Chicago, UChicago Argonne LLC for the United States Department of Energy. The facil ...
analyzed greenhouse gas emissions of many different engine and fuel combinations, and found that
biodiesel Biodiesel is a form of diesel fuel derived from plants or animals and consisting of long-chain fatty acid esters. It is typically made by chemically reacting lipids such as animal fat (tallow), soybean oil, or some other vegetable oil with ...
/petrodiesel blend ( B20) showed a reduction of 8%, conventional
E85 E85 is an abbreviation typically referring to an ethanol fuel blend of 85% ethanol fuel and 15% gasoline or other hydrocarbon by volume. In the United States, the exact ratio of fuel ethanol to hydrocarbon may vary according to ASTM 5798 that ...
ethanol blend a reduction of 17% and
cellulosic ethanol Cellulosic ethanol is ethanol (ethyl alcohol) produced from cellulose (the stringy fiber of a plant) rather than from the plant's seeds or fruit. It can be produced from grasses, wood, algae, or other plants. It is generally discussed for use as a ...
64%, compared with pure gasoline. Ethanol has a much greater research octane number (RON) than gasoline, meaning it is less prone to pre-ignition, allowing for better ignition advance which means more torque, and efficiency in addition to the lower carbon emissions. Ethanol
combustion Combustion, or burning, is a high-temperature exothermic redox chemical reaction between a fuel (the reductant) and an oxidant, usually atmospheric oxygen, that produces oxidized, often gaseous products, in a mixture termed as smoke. Combusti ...
in an
internal combustion engine An internal combustion engine (ICE or IC engine) is a heat engine in which the combustion of a fuel occurs with an oxidizer (usually air) in a combustion chamber that is an integral part of the working fluid flow circuit. In an internal combus ...
yields many of the products of incomplete combustion produced by gasoline and significantly larger amounts of
formaldehyde Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section F ...
and related species such as acetaldehyde. This leads to a significantly larger photochemical reactivity and more
ground level ozone Ground-level ozone (O3), also known as surface-level ozone and tropospheric ozone, is a trace gas in the troposphere (the lowest level of the atmosphere of Earth, Earth's atmosphere), with an average concentration of 20–30 parts per billion by v ...
. This data has been assembled into The Clean Fuels Report comparison of fuel emissions and show that ethanol exhaust generates 2.14 times as much ozone as gasoline exhaust. When this is added into the custom ''Localized Pollution Index (LPI)'' of The Clean Fuels Report, the local pollution of ethanol (pollution that contributes to smog) is rated 1.7, where gasoline is 1.0 and higher numbers signify greater pollution. The
California Air Resources Board The California Air Resources Board (CARB or ARB) is the "clean air agency" of the government of California. Established in 1967 when then-governor Ronald Reagan signed the Mulford-Carrell Act, combining the Bureau of Air Sanitation and the Motor ...
formalized this issue in 2008 by recognizing control standards for formaldehydes as an emissions control group, much like the conventional
NOx In atmospheric chemistry, is shorthand for nitric oxide () and nitrogen dioxide (), the nitrogen oxides that are most relevant for air pollution. These gases contribute to the formation of smog and acid rain, as well as affecting tropos ...
and Reactive Organic Gases (ROGs). More than 20% of Brazilian cars are able to use 100% ethanol as fuel, which includes ethanol-only engines and
flex-fuel A flexible-fuel vehicle (FFV) or dual-fuel vehicle (colloquially called a flex-fuel vehicle) is an alternative fuel vehicle with an internal combustion engine designed to run on more than one fuel, usually gasoline blended with either ethanol fu ...
engines. Flex-fuel engines in Brazil are able to work with all ethanol, all gasoline or any mixture of both. In the U.S. flex-fuel vehicles can run on 0% to 85% ethanol (15% gasoline) since higher ethanol blends are not yet allowed or efficient. Brazil supports this fleet of ethanol-burning automobiles with large national infrastructure that produces ethanol from domestically grown sugarcane. Ethanol's high
miscibility Miscibility () is the property of two substances to mix in all proportions (that is, to fully dissolve in each other at any concentration), forming a homogeneous mixture (a solution). The term is most often applied to liquids but also applies ...
with water makes it unsuitable for shipping through modern pipelines like liquid hydrocarbons. Mechanics have seen increased cases of damage to small engines (in particular, the
carburetor A carburetor (also spelled carburettor) is a device used by an internal combustion engine to control and mix air and fuel entering the engine. The primary method of adding fuel to the intake air is through the venturi tube in the main meteri ...
) and attribute the damage to the increased water retention by ethanol in fuel.


Rocket fuel

Ethanol was commonly used as fuel in early
bipropellant The highest specific impulse chemical rockets use liquid propellants (liquid-propellant rockets). They can consist of a single chemical (a monopropellant) or a mix of two chemicals, called bipropellants. Bipropellants can further be divided into ...
rocket A rocket (from it, rocchetto, , bobbin/spool) is a vehicle that uses jet propulsion to accelerate without using the surrounding air. A rocket engine produces thrust by reaction to exhaust expelled at high speed. Rocket engines work entirely fr ...
(liquid-propelled) vehicles, in conjunction with an
oxidizer An oxidizing agent (also known as an oxidant, oxidizer, electron recipient, or electron acceptor) is a substance in a redox chemical reaction that gains or " accepts"/"receives" an electron from a (called the , , or ). In other words, an oxid ...
such as liquid oxygen. The German A-4 ballistic rocket of
World War II World War II or the Second World War, often abbreviated as WWII or WW2, was a world war that lasted from 1939 to 1945. It involved the vast majority of the world's countries—including all of the great powers—forming two opposin ...
(better known by its propaganda name ), which is credited as having begun the space age, used ethanol as the main constituent of ''B-Stoff''. Under such nomenclature, the ethanol was mixed with 25% water to reduce the combustion chamber temperature.Braeunig, Robert A
"Rocket Propellants"
''Rocket & Space Technology'', 2006. Retrieved 23 August 2007.
The design team helped develop U.S. rockets following World War II, including the ethanol-fueled
Redstone rocket The PGM-11 Redstone was the first large American ballistic missile. A short-range ballistic missile (SRBM), it was in active service with the United States Army in West Germany from June 1958 to June 1964 as part of NATO's Cold War defense of W ...
which launched the first U.S. satellite. Alcohols fell into general disuse as more energy-dense rocket fuels were developed, although ethanol is currently used in
lightweight Lightweight is a weight class in combat sports and rowing. Boxing Professional boxing The lightweight division is over 130 pounds (59 kilograms) and up to 135 pounds (61.2 kilograms) weight class in the sport of boxing. Notable lightweight boxe ...
rocket-powered racing aircraft.


Fuel cells

Commercial fuel cells operate on reformed natural gas,
hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-toxic, an ...
or methanol. Ethanol is an attractive alternative due to its wide availability, low cost, high purity and low toxicity. There is a wide range of fuel cell concepts that have entered trials including
direct-ethanol fuel cell Direct-ethanol fuel cells or DEFCs are a category of fuel cell in which ethanol is fed directly into the cell. They have been used as a model to investigate a range of fuel cell concepts including the use of PEM. Advantages DEFC uses Ethanol i ...
s, auto-thermal reforming systems and thermally integrated systems. The majority of work is being conducted at a research level although there are a number of organizations at the beginning of the commercialization of ethanol fuel cells.


Household heating and cooking

Ethanol fireplaces can be used for home heating or for decoration. Ethanol can also be used as stove fuel for cooking.


Feedstock

Ethanol is an important industrial ingredient. It has widespread use as a precursor for other organic compounds such as ethyl
halide In chemistry, a halide (rarely halogenide) is a binary chemical compound, of which one part is a halogen atom and the other part is an element or radical that is less electronegative (or more electropositive) than the halogen, to make a fluor ...
s, ethyl
ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...
s, diethyl ether, acetic acid, and ethyl
amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituen ...
s.


Solvent

Ethanol is considered a universal
solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...
, as its
molecular A molecule is a group of two or more atoms held together by attractive forces known as chemical bonds; depending on context, the term may or may not include ions which satisfy this criterion. In quantum physics, organic chemistry, and bioche ...
structure allows for the dissolving of both
polar Polar may refer to: Geography Polar may refer to: * Geographical pole, either of two fixed points on the surface of a rotating body or planet, at 90 degrees from the equator, based on the axis around which a body rotates * Polar climate, the c ...
,
hydrophilic A hydrophile is a molecule or other molecular entity that is attracted to water molecules and tends to be dissolved by water.Liddell, H.G. & Scott, R. (1940). ''A Greek-English Lexicon'' Oxford: Clarendon Press. In contrast, hydrophobes are no ...
and
nonpolar In chemistry, polarity is a separation of electric charge leading to a molecule or its chemical groups having an electric dipole moment, with a negatively charged end and a positively charged end. Polar molecules must contain one or more polar ...
,
hydrophobic In chemistry, hydrophobicity is the physical property of a molecule that is seemingly repelled from a mass of water (known as a hydrophobe). In contrast, hydrophiles are attracted to water. Hydrophobic molecules tend to be nonpolar and, th ...
compounds. As ethanol also has a low
boiling point The boiling point of a substance is the temperature at which the vapor pressure of a liquid equals the pressure surrounding the liquid and the liquid changes into a vapor. The boiling point of a liquid varies depending upon the surrounding envir ...
, it is easy to remove from a solution that has been used to dissolve other compounds, making it a popular extracting agent for botanical oils.
Cannabis ''Cannabis'' () is a genus of flowering plants in the family Cannabaceae. The number of species within the genus is disputed. Three species may be recognized: ''Cannabis sativa'', '' C. indica'', and '' C. ruderalis''. Alternatively ...
oil extraction methods often use ethanol as an extraction solvent, and also as a post-processing solvent to remove oils, waxes, and
chlorophyll Chlorophyll (also chlorophyl) is any of several related green pigments found in cyanobacteria and in the chloroplasts of algae and plants. Its name is derived from the Greek words , ("pale green") and , ("leaf"). Chlorophyll allow plants to a ...
from solution in a process known as
winterization Winterization is the process of preparing something for winter. Humanitarian aid In emergency or disaster response situations, such as managed by the UNHCR, winterization activities include the distribution of items including blankets, quilts, ...
. Ethanol is found in
paint Paint is any pigmented liquid, liquefiable, or solid mastic composition that, after application to a substrate in a thin layer, converts to a solid film. It is most commonly used to protect, color, or provide texture. Paint can be made in many ...
s,
tincture A tincture is typically an extract of plant or animal material dissolved in ethanol (ethyl alcohol). Solvent concentrations of 25–60% are common, but may run as high as 90%.Groot Handboek Geneeskrachtige Planten by Geert Verhelst In chemistr ...
s, markers, and personal care products such as mouthwashes, perfumes and deodorants. However,
polysaccharides Polysaccharides (), or polycarbohydrates, are the most abundant carbohydrates found in food. They are long chain polymeric carbohydrates composed of monosaccharide units bound together by glycosidic linkages. This carbohydrate can react with w ...
precipitate In an aqueous solution, precipitation is the process of transforming a dissolved substance into an insoluble solid from a super-saturated solution. The solid formed is called the precipitate. In case of an inorganic chemical reaction leading ...
from aqueous solution in the presence of alcohol, and ethanol precipitation is used for this reason in the purification of DNA and
RNA Ribonucleic acid (RNA) is a polymeric molecule essential in various biological roles in coding, decoding, regulation and expression of genes. RNA and deoxyribonucleic acid ( DNA) are nucleic acids. Along with lipids, proteins, and carbohydra ...
.


Low-temperature liquid

Because of its low freezing point of and low toxicity, ethanol is sometimes used in laboratories (with
dry ice Dry ice is the solid form of carbon dioxide. It is commonly used for temporary refrigeration as CO2 does not have a liquid state at normal atmospheric pressure and sublimates directly from the solid state to the gas state. It is used primarily a ...
or other coolants) as a
cooling bath A cooling bath or ice bath, in laboratory chemistry practice, is a liquid mixture which is used to maintain low temperatures, typically between 13 °C and −196 °C. These low temperatures are used to collect liquids after distillation ...
to keep vessels at temperatures below the freezing point of water. For the same reason, it is also used as the active fluid in
alcohol thermometer The alcohol thermometer or spirit thermometer is an alternative to the mercury-in-glass thermometer and has similar functions. Unlike the mercury-in-glass thermometer, the contents of an alcohol thermometer are less toxic and will evaporate qui ...
s.


Chemistry


Chemical formula

Ethanol is a 2-carbon alcohol. Its
molecular formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...
is CH3CH2OH. An alternative notation is CH3−CH2−OH, which indicates that the carbon of a
methyl group In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many ...
(CH3−) is attached to the carbon of a
methylene group In organic chemistry, a methylene group is any part of a molecule that consists of two hydrogen atoms bound to a carbon atom, which is connected to the remainder of the molecule by two single bonds. The group may be represented as , where the '< ...
(−CH2–), which is attached to the oxygen of a
hydroxyl group In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy g ...
(−OH). It is a constitutional
isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Iso ...
of
dimethyl ether Dimethyl ether (DME; also known as methoxymethane) is the organic compound with the formula CH3OCH3, (sometimes ambiguously simplified to C2H6O as it is an isomer of ethanol). The simplest ether, it is a colorless gas that is a useful precursor ...
. Ethanol is sometimes abbreviated as EtOH, using the common organic chemistry notation of representing the ethyl group (C2H5−) with Et.


Physical properties

Ethanol is a volatile, colorless liquid that has a slight odor. It burns with a smokeless blue flame that is not always visible in normal light. The physical properties of ethanol stem primarily from the presence of its hydroxyl group and the shortness of its carbon chain. Ethanol's hydroxyl group is able to participate in hydrogen bonding, rendering it more viscous and less volatile than less polar organic compounds of similar molecular weight, such as
propane Propane () is a three-carbon alkane with the molecular formula . It is a gas at standard temperature and pressure, but compressible to a transportable liquid. A by-product of natural gas processing and petroleum refining, it is commonly used a ...
. Ethanol's
adiabatic flame temperature In the study of combustion, the adiabatic flame temperature is the temperature reached by a flame under ideal conditions. It is an upper bound of the temperature that is reached in actual processes. There are two types adiabatic flame temperature: ...
for combustion in air is 2082
Celsius The degree Celsius is the unit of temperature on the Celsius scale (originally known as the centigrade scale outside Sweden), one of two temperature scales used in the International System of Units (SI), the other being the Kelvin scale. The ...
or 3779
Fahrenheit The Fahrenheit scale () is a temperature scale based on one proposed in 1724 by the physicist Daniel Gabriel Fahrenheit (1686–1736). It uses the degree Fahrenheit (symbol: °F) as the unit. Several accounts of how he originally defined his ...
. Ethanol is slightly more refractive than water, having a
refractive index In optics, the refractive index (or refraction index) of an optical medium is a dimensionless number that gives the indication of the light bending ability of that medium. The refractive index determines how much the path of light is bent, or ...
of 1.36242 (at λ=589.3 nm and ). The
triple point In thermodynamics, the triple point of a substance is the temperature and pressure at which the three phases (gas, liquid, and solid) of that substance coexist in thermodynamic equilibrium.. It is that temperature and pressure at which the subli ...
for ethanol is at a pressure of .


Solvent properties

Ethanol is a versatile solvent,
miscible Miscibility () is the property of two substances to mix in all proportions (that is, to fully dissolve in each other at any concentration), forming a homogeneous mixture (a solution). The term is most often applied to liquids but also applies ...
with water and with many organic solvents, including
acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main component ...
,
acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscib ...
,
benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...
,
carbon tetrachloride Carbon tetrachloride, also known by many other names (such as tetrachloromethane, also IUPAC nomenclature of inorganic chemistry, recognised by the IUPAC, carbon tet in the cleaning industry, Halon-104 in firefighting, and Refrigerant-10 in HVAC ...
,
chloroform Chloroform, or trichloromethane, is an organic compound with chemical formula, formula Carbon, CHydrogen, HChlorine, Cl3 and a common organic solvent. It is a colorless, strong-smelling, dense liquid produced on a large scale as a precursor to ...
,
diethyl ether Diethyl ether, or simply ether, is an organic compound in the ether class with the formula , sometimes abbreviated as (see Pseudoelement symbols). It is a colourless, highly volatile, sweet-smelling ("ethereal odour"), extremely flammable liq ...
, ethylene glycol,
glycerol Glycerol (), also called glycerine in British English and glycerin in American English, is a simple triol compound. It is a colorless, odorless, viscous liquid that is sweet-tasting and non-toxic. The glycerol backbone is found in lipids known ...
,
nitromethane Nitromethane, sometimes shortened to simply "nitro", is an organic compound with the chemical formula . It is the simplest organic nitro compound. It is a polar liquid commonly used as a solvent in a variety of industrial applications such as in ...
,
pyridine Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with a d ...
, and
toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon. It is a colorless, water-insoluble liquid with the smell associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) at ...
. Its main use as a solvent is in making tincture of iodine, cough syrups etc. It is also miscible with light aliphatic hydrocarbons, such as
pentane Pentane is an organic compound with the formula C5H12—that is, an alkane with five carbon atoms. The term may refer to any of three structural isomers, or to a mixture of them: in the IUPAC nomenclature, however, pentane means exclusively the ' ...
and
hexane Hexane () is an organic compound, a straight-chain alkane with six carbon atoms and has the molecular formula C6H14. It is a colorless liquid, odorless when pure, and with boiling points approximately . It is widely used as a cheap, relatively ...
, and with aliphatic chlorides such as
trichloroethane Trichloroethane (CHCl) may refer to either of two isomeric chemical compounds: * 1,1,1-Trichloroethane (methyl chloroform, CClCH) * 1,1,2-Trichloroethane 1,1,2-Trichloroethane, or 1,1,2-TCA, is an organochloride solvent with the molecular formula ...
and
tetrachloroethylene Tetrachloroethylene, also known under the systematic name tetrachloroethene, or perchloroethylene, and many other names (and abbreviations such as "perc" or "PERC", and "PCE"), is a chlorocarbon with the formula Cl2C=CCl2 . It is a colorless liq ...
. Ethanol's miscibility with water contrasts with the immiscibility of longer-chain alcohols (five or more carbon atoms), whose water miscibility decreases sharply as the number of carbons increases. The miscibility of ethanol with
alkane In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which ...
s is limited to alkanes up to
undecane Undecane (also known as hendecane) is a liquid alkane hydrocarbon with the chemical formula CH3(CH2)9CH3. It is used as a mild sex attractant for various types of moths and cockroaches, and an alert signal for a variety of ants.Hölldobler B, Wils ...
: mixtures with
dodecane Dodecane (also known as dihexyl, bihexyl, adakane 12, or duodecane) is an oily liquid ''n''-alkane hydrocarbon with the chemical formula C12H26 (which has 355 isomers). It is used as a solvent, distillation chaser, and scintillator component. It ...
and higher alkanes show a
miscibility gap A miscibility gap is a region in a phase diagram for a mixture of components where the mixture exists as two or more phases – any region of composition of mixtures where the constituents are not completely miscible. The IUPAC Gold Book define ...
below a certain temperature (about 13 °C for dodecane). The miscibility gap tends to get wider with higher alkanes, and the temperature for complete miscibility increases. Ethanol-water mixtures have less volume than the sum of their individual components at the given fractions. Mixing equal volumes of ethanol and water results in only 1.92 volumes of mixture. Mixing ethanol and water is
exothermic In thermodynamics, an exothermic process () is a thermodynamic process or reaction that releases energy from the system to its surroundings, usually in the form of heat, but also in a form of light (e.g. a spark, flame, or flash), electricity (e ...
, with up to 777 J/mol being released at 298 K. Mixtures of ethanol and water form an
azeotrope An azeotrope () or a constant heating point mixture is a mixture of two or more liquids whose proportions cannot be altered or changed by simple distillation.Moore, Walter J. ''Physical Chemistry'', 3rd e Prentice-Hall 1962, pp. 140–142 This ...
at about 89 mole-% ethanol and 11 mole-% water or a mixture of 95.6 percent ethanol by mass (or about 97%
alcohol by volume Alcohol by volume (abbreviated as ABV, abv, or alc/vol) is a standard measure of how much alcohol (ethanol) is contained in a given volume of an alcoholic beverage (expressed as a volume percent). It is defined as the number of millilitres (mL) o ...
) at normal pressure, which boils at 351K (78 °C). This azeotropic composition is strongly temperature- and pressure-dependent and vanishes at temperatures below 303 K. Hydrogen bonding causes pure ethanol to be
hygroscopic Hygroscopy is the phenomenon of attracting and holding water molecules via either absorption or adsorption from the surrounding environment, which is usually at normal or room temperature. If water molecules become suspended among the substance ...
to the extent that it readily absorbs water from the air. The polar nature of the hydroxyl group causes ethanol to dissolve many ionic compounds, notably
sodium Sodium is a chemical element with the symbol Na (from Latin ''natrium'') and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable iso ...
and
potassium hydroxide Potassium hydroxide is an inorganic compound with the formula K OH, and is commonly called caustic potash. Along with sodium hydroxide (NaOH), KOH is a prototypical strong base. It has many industrial and niche applications, most of which exp ...
s,
magnesium chloride Magnesium chloride is the family of inorganic compounds with the formula , where x can range from 0 to 12. These salts are colorless or white solids that are highly soluble in water. These compounds and their solutions, both of which occur in natu ...
,
calcium chloride Calcium chloride is an inorganic compound, a salt with the chemical formula . It is a white crystalline solid at room temperature, and it is highly soluble in water. It can be created by neutralising hydrochloric acid with calcium hydroxide. Ca ...
, ammonium chloride,
ammonium bromide Ammonium bromide, NH4Br, is the ammonium salt of hydrobromic acid. The chemical crystallizes in colorless prisms, possessing a saline taste; it sublimes on heating and is easily soluble in water. On exposure to air it gradually assumes a yellow c ...
, and
sodium bromide Sodium bromide is an inorganic compound with the formula Na Br. It is a high-melting white, crystalline solid that resembles sodium chloride. It is a widely used source of the bromide ion and has many applications.Michael J. Dagani, Henry J. Ba ...
.
Sodium Sodium is a chemical element with the symbol Na (from Latin ''natrium'') and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable iso ...
and
potassium chloride Potassium chloride (KCl, or potassium salt) is a metal halide salt composed of potassium and chlorine. It is odorless and has a white or colorless vitreous crystal appearance. The solid dissolves readily in water, and its solutions have a salt ...
s are slightly soluble in ethanol. Because the ethanol molecule also has a nonpolar end, it will also dissolve nonpolar substances, including most
essential oil An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the o ...
s''Merck Index of Chemicals and Drugs'', 9th ed.; monographs 6575 through 6669 and numerous flavoring, coloring, and medicinal agents. The addition of even a few percent of ethanol to water sharply reduces the
surface tension Surface tension is the tendency of liquid surfaces at rest to shrink into the minimum surface area possible. Surface tension is what allows objects with a higher density than water such as razor blades and insects (e.g. water striders) to f ...
of water. This property partially explains the "
tears of wine The phenomenon called tears of wine is manifested as a ring of clear liquid, near the top of a glass of wine, from which droplets continuously form and drop back into the wine. It is most readily observed in a wine which has a high alcohol conten ...
" phenomenon. When wine is swirled in a glass, ethanol evaporates quickly from the thin film of wine on the wall of the glass. As the wine's ethanol content decreases, its surface tension increases and the thin film "beads up" and runs down the glass in channels rather than as a smooth sheet.


Flammability

An ethanol–water solution will catch fire if heated above a temperature called its
flash point The flash point of a material is the "lowest liquid temperature at which, under certain standardized conditions, a liquid gives off vapours in a quantity such as to be capable of forming an ignitable vapour/air mixture". (EN 60079-10-1) The fl ...
and an ignition source is then applied to it. For 20% alcohol by mass (about 25% by volume), this will occur at about . The flash point of pure ethanol is , but may be influenced very slightly by atmospheric composition such as pressure and humidity. Ethanol mixtures can ignite below average room temperature. Ethanol is considered a flammable liquid (Class 3 Hazardous Material) in concentrations above 2.35% by mass (3.0% by volume; 6
proof Proof most often refers to: * Proof (truth), argument or sufficient evidence for the truth of a proposition * Alcohol proof, a measure of an alcoholic drink's strength Proof may also refer to: Mathematics and formal logic * Formal proof, a con ...
). Dishes using burning alcohol for culinary effects are called
flambé :''Flambé is also a type of ceramic glaze.'' Flambé (, , ; also spelled flambe) is a cooking procedure in which alcohol is added to a hot pan to create a burst of flames. The word means "flamed" in French. Flambéing is often associated with t ...
.


Natural occurrence

Ethanol is a byproduct of the
metabolic process Metabolism (, from el, μεταβολή ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cell ...
of yeast. As such, ethanol will be present in any yeast habitat. Ethanol can commonly be found in overripe fruit. Ethanol produced by symbiotic yeast can be found in bertam palm blossoms. Although some animal species, such as the pentailed treeshrew, exhibit ethanol-seeking behaviors, most show no interest or avoidance of food sources containing ethanol. Ethanol is also produced during the germination of many plants as a result of natural anaerobiosis. Ethanol has been detected in
outer space Outer space, commonly shortened to space, is the expanse that exists beyond Earth and its atmosphere and between celestial bodies. Outer space is not completely empty—it is a near-perfect vacuum containing a low density of particles, pred ...
, forming an icy coating around dust grains in
interstellar cloud An interstellar cloud is generally an accumulation of gas, plasma, and dust in our and other galaxies. Put differently, an interstellar cloud is a denser-than-average region of the interstellar medium, the matter and radiation that exists in t ...
s. Minute quantity amounts (average 196 ppb) of endogenous ethanol and acetaldehyde were found in the exhaled breath of healthy volunteers.
Auto-brewery syndrome Auto-brewery syndrome (ABS) (also known as gut fermentation syndrome, endogenous ethanol fermentation or drunkenness disease) is a condition characterized by the fermentation of ingested carbohydrates in the gastrointestinal tract of the body cause ...
, also known as gut fermentation syndrome, is a rare medical condition in which intoxicating quantities of ethanol are produced through
endogenous Endogenous substances and processes are those that originate from within a living system such as an organism, tissue, or cell. In contrast, exogenous substances and processes are those that originate from outside of an organism. For example, es ...
fermentation Fermentation is a metabolic process that produces chemical changes in organic substrates through the action of enzymes. In biochemistry, it is narrowly defined as the extraction of energy from carbohydrates in the absence of oxygen. In food ...
within the
digestive system The human digestive system consists of the gastrointestinal tract plus the accessory organs of digestion (the tongue, salivary glands, pancreas, liver, and gallbladder). Digestion involves the breakdown of food into smaller and smaller compone ...
.


Production

Ethanol is produced both as a
petrochemical Petrochemicals (sometimes abbreviated as petchems) are the chemical products obtained from petroleum by refining. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sou ...
, through the hydration of
ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene i ...
and, via biological processes, by fermenting sugars with
yeast Yeasts are eukaryotic, single-celled microorganisms classified as members of the fungus kingdom. The first yeast originated hundreds of millions of years ago, and at least 1,500 species are currently recognized. They are estimated to constitut ...
. Which process is more economical depends on prevailing prices of
petroleum Petroleum, also known as crude oil, or simply oil, is a naturally occurring yellowish-black liquid mixture of mainly hydrocarbons, and is found in geological formations. The name ''petroleum'' covers both naturally occurring unprocessed crud ...
and grain feed stocks.


Sources

World production of ethanol in 2006 was , with 69% of the world supply coming from Brazil and the U.S. Brazilian ethanol is produced from
sugarcane Sugarcane or sugar cane is a species of (often hybrid) tall, Perennial plant, perennial grass (in the genus ''Saccharum'', tribe Andropogoneae) that is used for sugar Sugar industry, production. The plants are 2–6 m (6–20 ft) tall with ...
, which has relatively high yields (830% more fuel than the fossil fuels used to produce it) compared to some other
energy crops Energy crops are low-cost and low-maintenance crops grown solely for energy production by combustion (not for food). The crops are processed into solid, liquid or gaseous fuels, such as pellets, bioethanol or biogas. The fuels are burned to g ...
. Sugarcane not only has a greater concentration of sucrose than corn (by about 30%), but is also much easier to extract. The
bagasse Bagasse ( ) is the dry pulpy fibrous material that remains after crushing sugarcane or sorghum stalks to extract their juice. It is used as a biofuel for the production of heat, energy, and electricity, and in the manufacture of pulp and building ...
generated by the process is not discarded, but burned by power plants to produce electricity. Bagasse burning accounts for around 9% of the electricity produced in Brazil. In the 1970s most industrial ethanol in the U.S. was made as a petrochemical, but in the 1980s the U.S. introduced subsidies for
corn-based ethanol Corn ethanol is ethanol produced from corn biomass and is the main source of ethanol fuel in the United States, mandated to be blended with gasoline in the Renewable Fuel Standard. Corn ethanol is produced by ethanol fermentation and distillation ...
. According to the Renewable Fuels Association, as of 30 October 2007, 131 grain ethanol bio-refineries in the U.S. have the capacity to produce of ethanol per year. An additional 72 construction projects underway (in the U.S.) can add of new capacity in the next 18 months. In India ethanol is made from sugarcane.
Sweet sorghum Sweetness is a basic taste most commonly perceived when eating foods rich in sugars. Sweet tastes are generally regarded as pleasurable. In addition to sugars like sucrose, many other chemical compounds are sweet, including aldehydes, keto ...
is another potential source of ethanol, and is suitable for growing in dryland conditions. The
International Crops Research Institute for the Semi-Arid Tropics The International Crops Research Institute for the Semi-Arid Tropics (ICRISAT) is an international organization which conducts agricultural research for rural development, headquartered in Patancheru (Hyderabad, Telangana, India) with several r ...
is investigating the possibility of growing sorghum as a source of fuel, food, and animal feed in arid parts of
Asia Asia (, ) is one of the world's most notable geographical regions, which is either considered a continent in its own right or a subcontinent of Eurasia, which shares the continental landmass of Afro-Eurasia with Africa. Asia covers an area ...
and
Africa Africa is the world's second-largest and second-most populous continent, after Asia in both cases. At about 30.3 million km2 (11.7 million square miles) including adjacent islands, it covers 6% of Earth's total surface area ...
. Sweet sorghum has one-third the water requirement of sugarcane over the same time period. It also requires about 22% less water than corn. The world's first sweet sorghum ethanol distillery began commercial production in 2007 in
Andhra Pradesh Andhra Pradesh (, abbr. AP) is a state in the south-eastern coastal region of India. It is the seventh-largest state by area covering an area of and tenth-most populous state with 49,386,799 inhabitants. It is bordered by Telangana to the ...
,
India India, officially the Republic of India (Hindi: ), is a country in South Asia. It is the seventh-largest country by area, the second-most populous country, and the most populous democracy in the world. Bounded by the Indian Ocean on the so ...
.


Hydration

Ethanol can be produced from
petrochemical Petrochemicals (sometimes abbreviated as petchems) are the chemical products obtained from petroleum by refining. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sou ...
feed stocks, primarily by the
acid In computer science, ACID ( atomicity, consistency, isolation, durability) is a set of properties of database transactions intended to guarantee data validity despite errors, power failures, and other mishaps. In the context of databases, a sequ ...
-
catalyzed Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...
hydration Hydration may refer to: * Hydrate, a substance that contains water * Hydration enthalpy, energy released through hydrating a substance * Hydration reaction, a chemical addition reaction where a hydroxyl group and proton are added to a compound * ...
of ethylene. It is often referred to as synthetic ethanol. The catalyst is most commonly
phosphoric acid Phosphoric acid (orthophosphoric acid, monophosphoric acid or phosphoric(V) acid) is a colorless, odorless phosphorus-containing solid, and inorganic compound with the chemical formula . It is commonly encountered as an 85% aqueous solution, w ...
,
adsorbed Adsorption is the adhesion of atoms, ions or molecules from a gas, liquid or dissolved solid to a surface. This process creates a film of the ''adsorbate'' on the surface of the ''adsorbent''. This process differs from absorption, in which a ...
onto a porous support such as
silica gel Silica gel is an amorphous and porous form of silicon dioxide (silica), consisting of an irregular tridimensional framework of alternating silicon and oxygen atoms with nanometer-scale voids and pores. The voids may contain water or some other l ...
or
diatomaceous earth Diatomaceous earth (), diatomite (), or kieselgur/kieselguhr is a naturally occurring, soft, siliceous sedimentary rock that can be crumbled into a fine white to off-white powder. It has a particle size ranging from more than 3  μm to le ...
. This catalyst was first used for large-scale ethanol production by the
Shell Oil Company Shell USA, Inc. (formerly Shell Oil Company, Inc.) is the United States-based wholly owned subsidiary of Shell plc, a UK-based transnational corporation " oil major" which is amongst the largest oil companies in the world. Approximately 18,000 ...
in 1947. The reaction is carried out in the presence of high pressure steam at where a 5:3 ethylene to steam ratio is maintained. This process was used on an industrial scale by
Union Carbide Corporation Union Carbide Corporation is an American chemical corporation wholly owned subsidiary (since February 6, 2001) by Dow Chemical Company. Union Carbide produces chemicals and polymers that undergo one or more further conversions by customers befo ...
and others. It is no longer practiced in the US as fermentation ethanol produced from corn is more economical. In an older process, first practiced on the industrial scale in 1930 by Union Carbide but now almost entirely obsolete, ethylene was hydrated indirectly by reacting it with concentrated
sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular formu ...
to produce
ethyl sulfate Ethyl sulfate (IUPAC name: ethyl hydrogen sulfate), also known as sulfovinic acid, is an organic chemical compound used as an intermediate in the production of ethanol from ethylene. It is the ethyl ester of sulfuric acid. History This substance ...
, which was
hydrolyzed Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysis ...
to yield ethanol and regenerate the sulfuric acid:


From carbon dioxide

Ethanol has been produced in the laboratory by converting
carbon dioxide Carbon dioxide (chemical formula ) is a chemical compound made up of molecules that each have one carbon atom covalently double bonded to two oxygen atoms. It is found in the gas state at room temperature. In the air, carbon dioxide is transpar ...
via biological and
electrochemical Electrochemistry is the branch of physical chemistry concerned with the relationship between electrical potential difference, as a measurable and quantitative phenomenon, and identifiable chemical change, with the potential difference as an outco ...
reactions.


Fermentation

Ethanol in
alcoholic beverage An alcoholic beverage (also called an alcoholic drink, adult beverage, or a drink) is a drink that contains ethanol, a type of alcohol that acts as a drug and is produced by fermentation of grains, fruits, or other sources of sugar. The c ...
s and fuel is produced by fermentation. Certain species of
yeast Yeasts are eukaryotic, single-celled microorganisms classified as members of the fungus kingdom. The first yeast originated hundreds of millions of years ago, and at least 1,500 species are currently recognized. They are estimated to constitut ...
(e.g., ''
Saccharomyces cerevisiae ''Saccharomyces cerevisiae'' () (brewer's yeast or baker's yeast) is a species of yeast (single-celled fungus microorganisms). The species has been instrumental in winemaking, baking, and brewing since ancient times. It is believed to have been o ...
'')
metabolize Metabolism (, from el, μεταβολή ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cell ...
sugar Sugar is the generic name for sweet-tasting, soluble carbohydrates, many of which are used in food. Simple sugars, also called monosaccharides, include glucose, fructose, and galactose. Compound sugars, also called disaccharides or double ...
, producing ethanol and carbon dioxide. The chemical equations below summarize the conversion: Fermentation is the process of culturing yeast under favorable thermal conditions to produce alcohol. This process is carried out at around . Toxicity of ethanol to yeast limits the ethanol concentration obtainable by brewing; higher concentrations, therefore, are obtained by
fortification A fortification is a military construction or building designed for the defense of territories in warfare, and is also used to establish rule in a region during peacetime. The term is derived from Latin ''fortis'' ("strong") and ''facere'' ...
or
distillation Distillation, or classical distillation, is the process of separation process, separating the components or substances from a liquid mixture by using selective boiling and condensation, usually inside an apparatus known as a still. Dry distilla ...
. The most ethanol-tolerant yeast strains can survive up to approximately 18% ethanol by volume. To produce ethanol from starchy materials such as
cereal A cereal is any Poaceae, grass cultivated for the edible components of its grain (botanically, a type of fruit called a caryopsis), composed of the endosperm, Cereal germ, germ, and bran. Cereal Grain, grain crops are grown in greater quantit ...
s, the
starch Starch or amylum is a polymeric carbohydrate consisting of numerous glucose units joined by glycosidic bonds. This polysaccharide is produced by most green plants for energy storage. Worldwide, it is the most common carbohydrate in human diets ...
must first be converted into sugars. In brewing
beer Beer is one of the oldest and the most widely consumed type of alcoholic drink in the world, and the third most popular drink overall after water and tea. It is produced by the brewing and fermentation of starches, mainly derived from ce ...
, this has traditionally been accomplished by allowing the grain to germinate, or
malt Malt is germinated cereal grain that has been dried in a process known as " malting". The grain is made to germinate by soaking in water and is then halted from germinating further by drying with hot air. Malted grain is used to make beer, wh ...
, which produces the
enzyme Enzymes () are proteins that act as biological catalysts by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrates into different molecules known as products. A ...
amylase An amylase () is an enzyme that catalyses the hydrolysis of starch (Latin ') into sugars. Amylase is present in the saliva of humans and some other mammals, where it begins the chemical process of digestion. Foods that contain large amounts of ...
. When the malted grain is
mashed Mashed may refer to: * Mashed, that created from mash ingredients * Mashed, the result of a mashing * Mashed, the result of a mashup (music) * ''Mashed'' (album), a 2007 mashup album * ''Mashed'' (video game), a vehicular combat video game * ...
, the amylase converts the remaining starches into sugars.


Cellulose

Sugars for
ethanol fermentation Ethanol fermentation, also called alcoholic fermentation, is a biological process which converts sugars such as glucose, fructose, and sucrose into cellular energy, producing ethanol and carbon dioxide as by-products. Because yeasts perform this ...
can be obtained from
cellulose Cellulose is an organic compound with the formula , a polysaccharide consisting of a linear chain of several hundred to many thousands of β(1→4) linked D-glucose units. Cellulose is an important structural component of the primary cell wall ...
. Deployment of this technology could turn a number of cellulose-containing agricultural by-products, such as
corncob A corncob, also called corn cob, cob of corn or corn on the cob, is the central core of an ear of corn (also known as maize). It is the part of the ear on which the kernels grow. The ear is also considered a "cob" or "pole" but it is not fully ...
s,
straw Straw is an agricultural byproduct consisting of the dry stalks of cereal plants after the grain and chaff have been removed. It makes up about half of the yield of cereal crops such as barley, oats, rice, rye and wheat. It has a number ...
, and
sawdust Sawdust (or wood dust) is a by-product or waste product of woodworking operations such as sawing, sanding, milling, planing, and routing. It is composed of small chippings of wood. These operations can be performed by woodworking machinery, ...
, into renewable energy resources. Other agricultural residues such as sugarcane bagasse and
energy crop Energy crops are low-cost and low-maintenance crops grown solely for energy production by combustion (not for food). The crops are processed into solid, liquid or gaseous fuels, such as pellets, bioethanol or biogas. The fuels are burned to g ...
s such as
switchgrass ''Panicum virgatum'', commonly known as switchgrass, is a perennial warm season bunchgrass native to North America, where it occurs naturally from 55°N latitude in Canada southwards into the United States and Mexico. Switchgrass is one of the ...
may also be fermentable sugar sources.


Testing

Breweries and
biofuel Biofuel is a fuel that is produced over a short time span from biomass, rather than by the very slow natural processes involved in the formation of fossil fuels, such as oil. According to the United States Energy Information Administration (E ...
plants employ two methods for measuring ethanol concentration. Infrared ethanol sensors measure the vibrational frequency of dissolved ethanol using the C−H band at 2900 cm. This method uses a relatively inexpensive solid-state sensor that compares the C−H band with a reference band to calculate the ethanol content. The calculation makes use of the
Beer–Lambert law The Beer–Lambert law, also known as Beer's law, the Lambert–Beer law, or the Beer–Lambert–Bouguer law relates the attenuation of light to the properties of the material through which the light is travelling. The law is commonly applied t ...
. Alternatively, by measuring the density of the starting material and the density of the product, using a
hydrometer A hydrometer or lactometer is an instrument used for measuring density or relative density of liquids based on the concept of buoyancy. They are typically calibrated and graduated with one or more scales such as specific gravity. A hydrometer ...
, the change in specific gravity during fermentation indicates the alcohol content. This inexpensive and indirect method has a long history in the beer brewing industry.


Purification


Distillation

Ethylene hydration or brewing produces an ethanol–water mixture. For most industrial and fuel uses, the ethanol must be purified.
Fractional distillation Fractional distillation is the separation of a mixture into its component parts, or fractions. Chemical compounds are separated by heating them to a temperature at which one or more fractions of the mixture will vaporize. It uses distillation to ...
at atmospheric pressure can concentrate ethanol to 95.6% by weight (89.5 mole%). This mixture is an
azeotrope An azeotrope () or a constant heating point mixture is a mixture of two or more liquids whose proportions cannot be altered or changed by simple distillation.Moore, Walter J. ''Physical Chemistry'', 3rd e Prentice-Hall 1962, pp. 140–142 This ...
with a boiling point of , and ''cannot'' be further purified by distillation. Addition of an entraining agent, such as
benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...
,
cyclohexane Cyclohexane is a cycloalkane with the molecular formula . Cyclohexane is non-polar. Cyclohexane is a colorless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohexan ...
, or
heptane Heptane or ''n''-heptane is the straight-chain alkane with the chemical formula H3C(CH2)5CH3 or C7H16. When used as a test fuel component in anti-knock test engines, a 100% heptane fuel is the zero point of the octane rating scale (the 100 point ...
, allows a new ternary azeotrope comprising the ethanol, water, and the entraining agent to be formed. This lower-boiling ternary azeotrope is removed preferentially, leading to water-free ethanol.


Molecular sieves and desiccants

Apart from distillation, ethanol may be dried by addition of a
desiccant A desiccant is a hygroscopic substance that is used to induce or sustain a state of dryness (desiccation) in its vicinity; it is the opposite of a humectant. Commonly encountered pre-packaged desiccants are solids that absorb water. Desiccant ...
, such as
molecular sieves A molecular sieve is a material with pores (very small holes) of uniform size. These pore diameters are similar in size to small molecules, and thus large molecules cannot enter or be adsorbed, while smaller molecules can. As a mixture of molecu ...
,
cellulose Cellulose is an organic compound with the formula , a polysaccharide consisting of a linear chain of several hundred to many thousands of β(1→4) linked D-glucose units. Cellulose is an important structural component of the primary cell wall ...
, or
cornmeal Cornmeal is a meal (coarse flour) or a cell membrane ground from dried corn. It is a common staple food, and is ground to coarse, medium, and fine consistencies, but not as fine as wheat flour can be.Herbst, Sharon, ''Food Lover's Companion'', ...
. The desiccants can be dried and reused.
Molecular sieve A molecular sieve is a material with pores (very small holes) of uniform size. These pore diameters are similar in size to small molecules, and thus large molecules cannot enter or be adsorbed, while smaller molecules can. As a mixture of molecu ...
s can be used to selectively absorb the water from the 95.6% ethanol solution. Molecular sieves of pore-size 3 
Ångstrom The angstromEntry "angstrom" in the Oxford online dictionary. Retrieved on 2019-03-02 from https://en.oxforddictionaries.com/definition/angstrom.Entry "angstrom" in the Merriam-Webster online dictionary. Retrieved on 2019-03-02 from https://www.m ...
, a type of
zeolite Zeolites are microporous, crystalline aluminosilicate materials commonly used as commercial adsorbents and catalysts. They mainly consist of silicon, aluminium, oxygen, and have the general formula ・y where is either a metal ion or H+. These pos ...
, effectively sequester water molecules while excluding ethanol molecules. Heating the wet sieves drives out the water, allowing regeneration of their dessicant capability.


Membranes and reverse osmosis

Membranes can also be used to separate ethanol and water. Membrane-based separations are not subject to the limitations of the water-ethanol azeotrope because the separations are not based on vapor-liquid equilibria. Membranes are often used in the so-called hybrid membrane distillation process. This process uses a pre-concentration distillation column as the first separating step. The further separation is then accomplished with a membrane operated either in vapor permeation or pervaporation mode. Vapor permeation uses a vapor membrane feed and pervaporation uses a liquid membrane feed.


Other techniques

A variety of other techniques have been discussed, including the following: * Salting using
potassium carbonate Potassium carbonate is the inorganic compound with the formula K2 CO3. It is a white salt, which is soluble in water. It is deliquescent, often appearing as a damp or wet solid. Potassium carbonate is mainly used in the production of soap and gl ...
to exploit its insolubility will cause a phase separation with ethanol and water. This offers a very small potassium carbonate impurity to the alcohol that can be removed by distillation. This method is very useful in purification of ethanol by distillation, as ethanol forms an
azeotrope An azeotrope () or a constant heating point mixture is a mixture of two or more liquids whose proportions cannot be altered or changed by simple distillation.Moore, Walter J. ''Physical Chemistry'', 3rd e Prentice-Hall 1962, pp. 140–142 This ...
with water. * Direct
electrochemical reduction of carbon dioxide The electrochemical reduction of carbon dioxide, also known as electrolysis of carbon dioxide, is the conversion of carbon dioxide () to more reduced chemical species using electrical energy. It is one possible step in the broad scheme of carbon ...
to ethanol under ambient conditions using
copper nanoparticle A copper nanoparticle is a copper based particle 1 to 100 nm in size.Khan, F.A. ''Biotechnology Fundamentals''; CRC Press; Boca Raton, 2011 Like many other forms of nanoparticles, a copper nanoparticle can be prepared by natural processes or t ...
s on a carbon nanospike film as the catalyst; * Extraction of ethanol from grain mash by
supercritical carbon dioxide Supercritical carbon dioxide (s) is a fluid state of carbon dioxide where it is held at or above its critical temperature and critical pressure. Carbon dioxide usually behaves as a gas in air at standard temperature and pressure (STP), or as ...
; *
Pervaporation Pervaporation (or pervaporative separation) is a processing method for the separation of mixtures of liquids by partial vaporization through a non-porous or porous membrane. Theory The term ''pervaporation'' is a portmanteau of the two steps of the ...
; *
Fractional freezing Fractional freezing is a process used in process engineering and chemistry to separate substances with different melting points. It can be done by partial melting of a solid, for example in zone refining of silicon or metals, or by partial crys ...
is also used to concentrate fermented alcoholic solutions, such as traditionally made
Applejack (beverage) Applejack is a strong alcoholic drink produced from apples. Popular in the American colonial era, the drink's prevalence declined in the 19th and 20th centuries amid competition from other spirits.Michael Foley, ''Drinking with the Saints: The S ...
; *
Pressure swing adsorption Pressure swing adsorption (PSA) is a technique used to separate some gas species from a mixture of gases (typically air) under pressure according to the species' molecular characteristics and affinity for an adsorbent material. It operates at nea ...
.


Grades of ethanol


Denatured alcohol

Pure ethanol and alcoholic beverages are heavily
taxed A tax is a compulsory financial charge or some other type of levy imposed on a taxpayer (an individual or legal entity) by a governmental organization in order to fund government spending and various public expenditures (regional, local, or n ...
as psychoactive drugs, but ethanol has many uses that do not involve its consumption. To relieve the tax burden on these uses, most jurisdictions waive the tax when an agent has been added to the ethanol to render it unfit to drink. These include bittering agents such as
denatonium benzoate Denatonium, usually available as denatonium benzoate (under trade names such as Denatrol, BITTERANT-b, BITTER+PLUS, ''Bitrex'', and ''Aversion'') and as denatonium saccharide (BITTERANT-s), is the most bitter chemical compound known, with bitternes ...
and toxins such as methanol,
naphtha Naphtha ( or ) is a flammable liquid hydrocarbon mixture. Mixtures labelled ''naphtha'' have been produced from natural gas condensates, petroleum distillates, and the distillation of coal tar and peat. In different industries and regions ''n ...
, and
pyridine Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with a d ...
. Products of this kind are called ''denatured alcohol.''


Absolute alcohol

Absolute or anhydrous alcohol refers to ethanol with a low water content. There are various grades with maximum water contents ranging from 1% to a few parts per million (ppm). If
azeotropic distillation In chemistry, azeotropic distillation is any of a range of techniques used to break an azeotrope in distillation. In chemical engineering, ''azeotropic distillation'' usually refers to the specific technique of adding another component to genera ...
is used to remove water, it will contain trace amounts of the material separation agent (e.g. benzene). Absolute alcohol is not intended for human consumption. Absolute ethanol is used as a solvent for laboratory and industrial applications, where water will react with other chemicals, and as fuel alcohol. Spectroscopic ethanol is an absolute ethanol with a low absorbance in
ultraviolet Ultraviolet (UV) is a form of electromagnetic radiation with wavelength from 10 nanometer, nm (with a corresponding frequency around 30 Hertz, PHz) to 400 nm (750 Hertz, THz), shorter than that of visible light, but longer than ...
and visible light, fit for use as a solvent in ultraviolet-visible spectroscopy. Pure ethanol is classed as 200
proof Proof most often refers to: * Proof (truth), argument or sufficient evidence for the truth of a proposition * Alcohol proof, a measure of an alcoholic drink's strength Proof may also refer to: Mathematics and formal logic * Formal proof, a con ...
in the US, equivalent to 175 degrees proof in the UK system.


Rectified spirits

Rectified spirit, an azeotropic composition of 96% ethanol containing 4% water, is used instead of anhydrous ethanol for various purposes. Spirits of wine are about 94% ethanol (188 proof). The impurities are different from those in 95% (190 proof) laboratory ethanol.


Reactions

Ethanol is classified as a primary alcohol, meaning that the carbon that its hydroxyl group attaches to has at least two hydrogen atoms attached to it as well. Many ethanol reactions occur at its hydroxyl group.


Ester formation

In the presence of acid catalysts, ethanol reacts with
carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic ...
s to produce ethyl
ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...
s and water: : RCOOH + HOCH2CH3RCOOCH2CH3 + H2O This reaction, which is conducted on large scale industrially, requires the removal of the water from the reaction mixture as it is formed. Esters react in the presence of an acid or base to give back the alcohol and a salt. This reaction is known as
saponification Saponification is a process of converting esters into soaps and alcohols by the action of aqueous alkali (for example, aqueous sodium hydroxide solutions). Soaps are salts of fatty acids, which in turn are carboxylic acids with long carbon chains. ...
because it is used in the preparation of soap. Ethanol can also form esters with inorganic acids.
Diethyl sulfate Diethyl sulfate (DES) is a highly toxic, combustible, and likely carcinogenic chemical compound with the formula (C2H5)2SO4. It occurs as a colorless, oily liquid with a faint peppermint odor and is corrosive to tissue and metals. Diethyl sulfate ...
and
triethyl phosphate Triethyl phosphate is an organic chemical compound with the formula (C2H5)3PO4 or OP(OEt)3. It is a colorless liquid. It is the triester of ethanol and phosphoric acid and can be called "phosphoric acid, triethyl ester". Its primary uses are a ...
are prepared by treating ethanol with sulfur trioxide and
phosphorus pentoxide Phosphorus pentoxide is a chemical compound with molecular formula P4 O10 (with its common name derived from its empirical formula, P2O5). This white crystalline solid is the anhydride of phosphoric acid. It is a powerful desiccant and dehydra ...
respectively. Diethyl sulfate is a useful ethylating agent in
organic synthesis Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...
.
Ethyl nitrite The chemical compound ethyl nitrite is an alkyl nitrite with a chemical formula C2H5NO2. It may be prepared from ethanol. : Uses It is used as a reagent with butanone to yield the dimethylglyoxime end product. Ethyl nitrite is the main ingre ...
, prepared from the reaction of ethanol with
sodium nitrite Sodium nitrite is an inorganic compound with the chemical formula NaNO2. It is a white to slightly yellowish crystalline powder that is very soluble in water and is hygroscopic. From an industrial perspective, it is the most important nitrite ...
and sulfuric acid, was formerly used as a
diuretic A diuretic () is any substance that promotes diuresis, the increased production of urine. This includes forced diuresis. A diuretic tablet is sometimes colloquially called a water tablet. There are several categories of diuretics. All diuretics in ...
.


Dehydration

In the presence of acid catalysts, alcohols can be converted to alkenes such as ethanol to ethylene. Typically
solid acid Solid is one of the four fundamental states of matter (the others being liquid, gas, and plasma). The molecules in a solid are closely packed together and contain the least amount of kinetic energy. A solid is characterized by structural ri ...
s such as alumina are used. :   CH3CH2OH → H2C=CH2 + H2O Since water is removed from the same molecule, the reaction is known as intramolecular dehydration. Intramolecular dehydration of an alcohol requires a high temperature and the presence of an acid catalyst such as
sulphuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular formu ...
. Ethylene produced from sugar-derived ethanol (primarily in Brazil) competes with ethylene produced from petrochemical feedstocks such as naphtha and ethane. At a lower temperature than that of intramolecular dehydration, intermolecular alcohol dehydration may occur producing a symmetrical ether. This is a
condensation reaction In organic chemistry, a condensation reaction is a type of chemical reaction in which two molecules are combined to form a single molecule, usually with the loss of a small molecule such as water. If water is lost, the reaction is also known as a ...
. In the following example,
diethyl ether Diethyl ether, or simply ether, is an organic compound in the ether class with the formula , sometimes abbreviated as (see Pseudoelement symbols). It is a colourless, highly volatile, sweet-smelling ("ethereal odour"), extremely flammable liq ...
is produced from ethanol: :2 CH3CH2OH → CH3CH2OCH2CH3 + H2O


Combustion

Complete combustion of ethanol forms carbon dioxide and water: :C2H5OH (l) + 3 O2 (g) → 2 CO2 (g) + 3 H2O (l); −ΔHc = 1371 kJ/mol = 29.8 kJ/g = 327 kcal/mol = 7.1 kcal/g :C2H5OH (l) + 3 O2 (g) → 2 CO2 (g) + 3 H2O (g); −ΔHc = 1236 kJ/mol = 26.8 kJ/g = 295.4 kcal/mol = 6.41 kcal/g Specific heat = 2.44 kJ/(kg·K)


Acid-base chemistry

Ethanol is a neutral molecule and the pH of a solution of ethanol in water is nearly 7.00. Ethanol can be quantitatively converted to its
conjugate base A conjugate acid, within the Brønsted–Lowry acid–base theory, is a chemical compound formed when an acid donates a proton () to a base—in other words, it is a base with a hydrogen ion added to it, as in the reverse reaction it loses a ...
, the
ethoxide In chemistry, an alkoxide is the conjugate base of an alcohol and therefore consists of an organic group bonded to a negatively charged oxygen atom. They are written as , where R is the organic substituent. Alkoxides are strong bases and, w ...
ion (CH3CH2O), by reaction with an
alkali metal The alkali metals consist of the chemical elements lithium (Li), sodium (Na), potassium (K),The symbols Na and K for sodium and potassium are derived from their Latin names, ''natrium'' and ''kalium''; these are still the origins of the names ...
such as
sodium Sodium is a chemical element with the symbol Na (from Latin ''natrium'') and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable iso ...
: :2 CH3CH2OH + 2 Na → 2 CH3CH2ONa + H2 or a very strong base such as
sodium hydride Sodium hydride is the chemical compound with the empirical formula Na H. This alkali metal hydride is primarily used as a strong yet combustible base in organic synthesis. NaH is a saline (salt-like) hydride, composed of Na+ and H− ions, in co ...
: :CH3CH2OH + NaH → CH3CH2ONa + H2 The acidities of water and ethanol are nearly the same, as indicated by their
pKa PKA may refer to: * Professionally known as: ** Pen name ** Stage persona * p''K''a, the symbol for the acid dissociation constant at logarithmic scale * Protein kinase A, a class of cAMP-dependent enzymes * Pi Kappa Alpha, the North-American so ...
of 15.7 and 16 respectively. Thus, sodium ethoxide and
sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkali ...
exist in an equilibrium that is closely balanced: :CH3CH2OH + NaOH CH3CH2ONa + H2O


Halogenation

Ethanol is not used industrially as a precursor to ethyl halides, but the reactions are illustrative. Ethanol reacts with
hydrogen halide In chemistry, hydrogen halides (hydrohalic acids when in the aqueous phase) are diatomic, inorganic compounds that function as Arrhenius acids. The formula is HX where X is one of the halogens: fluorine, chlorine, bromine, iodine, or astatine. A ...
s to produce ethyl halides such as
ethyl chloride Chloroethane, commonly known as ethyl chloride, is a chemical compound with chemical formula CH3CH2Cl, once widely used in producing tetraethyllead, a gasoline additive. It is a colorless, flammable gas or refrigerated liquid with a faintly sweet ...
and
ethyl bromide Bromoethane, also known as ethyl bromide, is a chemical compound of the haloalkanes group. It is abbreviated by chemists as EtBr (which is also used as an abbreviation for ethidium bromide). This volatile compound has an ether-like odor. Prepara ...
via an SN2 reaction: :CH3CH2OH +
HCl HCL may refer to: Science and medicine * Hairy cell leukemia, an uncommon and slowly progressing B cell leukemia * Harvard Cyclotron Laboratory, from 1961 to 2002, a proton accelerator used for research and development * Hollow-cathode lamp, a spe ...
→ CH3CH2Cl + H2O These reactions require a catalyst such as
zinc chloride Zinc chloride is the name of inorganic chemical compounds with the formula ZnCl2 and its hydrates. Zinc chlorides, of which nine crystalline forms are known, are colorless or white, and are highly soluble in water. This salt is hygroscopic and ev ...
. HBr requires
refluxing Reflux is a technique involving the condensation of vapors and the return of this condensate to the system from which it originated. It is used in industrial and laboratory distillations. It is also used in chemistry to supply energy to Chemical ...
with a
sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular formu ...
catalyst. Ethyl halides can, in principle, also be produced by treating ethanol with more specialized halogenating agents, such as
thionyl chloride Thionyl chloride is an inorganic compound with the chemical formula . It is a moderately volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately per year bein ...
or
phosphorus tribromide Phosphorus tribromide is a colourless liquid with the formula P Br3. The liquid fumes in moist air due to hydrolysis and has a penetrating odour. It is used in the laboratory for the conversion of alcohols to alkyl bromides. Preparation PBr3 ...
. :CH3CH2OH + SOCl2 → CH3CH2Cl + SO2 + HCl Upon treatment with halogens in the presence of base, ethanol gives the corresponding
haloform In chemistry, trihalomethanes (THMs) are chemical compounds in which three of the four hydrogen atoms of methane () are replaced by halogen atoms. Many trihalomethanes find uses in industry as solvents or refrigerants. THMs are also environmenta ...
(CHX3, where X = Cl, Br, I). This conversion is called the
haloform reaction In chemistry, the haloform reaction is a chemical reaction in which a haloform (, where X is a halogen) is produced by the exhaustive halogenation of an acetyl group (, where R can be either a hydrogen atom, an alkyl or an aryl group), in the ...
. An intermediate in the reaction with chlorine is the
aldehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl grou ...
called
chloral Chloral, also known as trichloroacetaldehyde or trichloroethanal, is the organic compound with the formula Cl3CCHO. This aldehyde is a colourless oily liquid that is soluble in a wide range of solvents. It reacts with water to form chloral hydrate ...
, which forms
chloral hydrate Chloral hydrate is a geminal diol with the formula . It is a colorless solid. It has limited use as a sedative and hypnotic pharmaceutical drug. It is also a useful laboratory chemical reagent and precursor. It is derived from chloral (trichl ...
upon reaction with water: :4 Cl2 + CH3CH2OH → CCl3CHO + 5 HCl :CCl3CHO + H2O → CCl3C(OH)2H


Oxidation

Ethanol can be oxidized to
acetaldehyde Acetaldehyde (IUPAC systematic name ethanal) is an organic chemical compound with the formula CH3 CHO, sometimes abbreviated by chemists as MeCHO (Me = methyl). It is a colorless liquid or gas, boiling near room temperature. It is one of the mos ...
and further oxidized to
acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main component ...
, depending on the reagents and conditions. This oxidation is of no importance industrially, but in the human body, these oxidation reactions are catalyzed by the
enzyme Enzymes () are proteins that act as biological catalysts by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrates into different molecules known as products. A ...
liver alcohol dehydrogenase Alcohol dehydrogenases (ADH) () are a group of dehydrogenase enzymes that occur in many organisms and facilitate the interconversion between alcohols and aldehydes or ketones with the reduction of nicotinamide adenine dinucleotide (NAD+) to N ...
. The oxidation product of ethanol, acetic acid, is a nutrient for humans, being a precursor to
acetyl CoA Acetyl-CoA (acetyl coenzyme A) is a molecule that participates in many biochemical reactions in protein, carbohydrate and lipid metabolism. Its main function is to deliver the acetyl group to the citric acid cycle (Krebs cycle) to be oxidized for ...
, where the acetyl group can be spent as energy or used for biosynthesis.


Metabolism

Ethanol is similar to
macronutrients A nutrient is a substance used by an organism to survive, grow, and reproduce. The requirement for dietary nutrient intake applies to animals, plants, fungi, and protists. Nutrients can be incorporated into cells for metabolic purposes or excret ...
such as proteins, fats, and carbohydrates in that it provides calories. When consumed and metabolized, it contributes 7 calories per gram via ethanol metabolism.


Safety

Pure ethanol will irritate the skin and eyes. Nausea,
vomiting Vomiting (also known as emesis and throwing up) is the involuntary, forceful expulsion of the contents of one's stomach through the mouth and sometimes the Human nose, nose. Vomiting can be the result of ailments like Food-poisoning, foo ...
, and intoxication are symptoms of ingestion. Long-term use by ingestion can result in serious liver damage. Atmospheric concentrations above one part per thousand are above the European Union
occupational exposure limit An occupational exposure limit is an upper limit on the acceptable concentration of a hazardous substance in workplace air for a particular material or class of materials. It is typically set by competent national authorities and enforced by legi ...
s.


History

The fermentation of sugar into ethanol is one of the earliest
biotechnologies Biotechnology is the integration of natural sciences and engineering sciences in order to achieve the application of organisms, cells, parts thereof and molecular analogues for products and services. The term ''biotechnology'' was first used b ...
employed by humans. Ethanol has historically been identified variously as spirit of wine or ardent spirits, and as
aqua vitae ''Aqua vitae'' (Latin for "water of life") or aqua vita is an archaic name for a concentrated aqueous solution of ethanol. These terms could also be applied to weak ethanol without rectification. Usage was widespread during the Middle Ages a ...
or aqua vita. The intoxicating effects of its consumption have been known since ancient times. Ethanol has been used by humans since prehistory as the intoxicating ingredient of
alcoholic beverage An alcoholic beverage (also called an alcoholic drink, adult beverage, or a drink) is a drink that contains ethanol, a type of alcohol that acts as a drug and is produced by fermentation of grains, fruits, or other sources of sugar. The c ...
s. Dried residue on 9,000-year-old pottery found in China suggests that
Neolithic The Neolithic period, or New Stone Age, is an Old World archaeological period and the final division of the Stone Age. It saw the Neolithic Revolution, a wide-ranging set of developments that appear to have arisen independently in several parts ...
people consumed alcoholic beverages. The inflammable nature of the exhalations of wine was already known to ancient natural philosophers such as
Aristotle Aristotle (; grc-gre, Ἀριστοτέλης ''Aristotélēs'', ; 384–322 BC) was a Greek philosopher and polymath during the Classical period in Ancient Greece. Taught by Plato, he was the founder of the Peripatetic school of phil ...
(384–322 BCE),
Theophrastus Theophrastus (; grc-gre, Θεόφραστος ; c. 371c. 287 BC), a Greek philosopher and the successor to Aristotle in the Peripatetic school. He was a native of Eresos in Lesbos.Gavin Hardy and Laurence Totelin, ''Ancient Botany'', Routledge ...
(–287 BCE), and
Pliny the Elder Gaius Plinius Secundus (AD 23/2479), called Pliny the Elder (), was a Roman author, naturalist and natural philosopher, and naval and army commander of the early Roman Empire, and a friend of the emperor Vespasian. He wrote the encyclopedic '' ...
(23/24–79 CE). However, this did not immediately lead to the isolation of ethanol, even despite the development of more advanced distillation techniques in second- and third-century
Roman Egypt , conventional_long_name = Roman Egypt , common_name = Egypt , subdivision = Province , nation = the Roman Empire , era = Late antiquity , capital = Alexandria , title_leader = Praefectus Augustalis , image_map = Roman E ...
. An important recognition, first found in one of the writings attributed to Jābir ibn Ḥayyān (ninth century CE), was that by adding salt to boiling wine, which increases the wine's
relative volatility Relative volatility is a measure comparing the vapor pressures of the components in a liquid mixture of chemicals. This quantity is widely used in designing large industrial distillation processes. In effect, it indicates the ease or difficulty of u ...
, the flammability of the resulting vapors may be enhanced. The distillation of wine is attested in Arabic works attributed to
al-Kindī Abū Yūsuf Yaʻqūb ibn ʼIsḥāq aṣ-Ṣabbāḥ al-Kindī (; ar, أبو يوسف يعقوب بن إسحاق الصبّاح الكندي; la, Alkindus; c. 801–873 AD) was an Arab Muslim philosopher, polymath, mathematician, physician ...
(–873 CE) and to
al-Fārābī Abu Nasr Muhammad Al-Farabi ( fa, ابونصر محمد فارابی), ( ar, أبو نصر محمد الفارابي), known in the West as Alpharabius; (c. 872 – between 14 December, 950 and 12 January, 951)PDF version was a renowned early Isla ...
(–950), and in the 28th book of al-Zahrāwī's (Latin: Abulcasis, 936–1013) ''Kitāb al-Taṣrīf'' (later translated into Latin as ''Liber servatoris''). In the twelfth century, recipes for the production of ''aqua ardens'' ("burning water", i.e., ethanol) by distilling wine with salt started to appear in a number of Latin works, and by the end of the thirteenth century it had become a widely known substance among Western European chemists. The works of
Taddeo Alderotti Taddeo Alderotti (Latin: Thaddaeus Alderottus, French : Thaddée de Florence), born in Florence between 1206 and 1215, died in 1295, was an Italian doctor and professor of medicine at the University of Bologna, who made important contributions ...
(1223–1296) describe a method for concentrating ethanol involving repeated
fractional distillation Fractional distillation is the separation of a mixture into its component parts, or fractions. Chemical compounds are separated by heating them to a temperature at which one or more fractions of the mixture will vaporize. It uses distillation to ...
through a water-cooled
still A still is an apparatus used to distill liquid mixtures by heating to selectively boil and then cooling to condense the vapor. A still uses the same concepts as a basic distillation apparatus, but on a much larger scale. Stills have been used ...
, by which an ethanol purity of 90% could be obtained. The medicinal properties of ethanol were studied by
Arnald of Villanova Arnaldus de Villa Nova (also called Arnau de Vilanova in Catalan, his language, Arnaldus Villanovanus, Arnaud de Ville-Neuve or Arnaldo de Villanueva, c. 1240–1311) was a physician and a religious reformer. He was also thought to be an alche ...
(1240–1311 CE) and
John of Rupescissa :''Johannes de Rupescissa may also refer to Cardinal Jean de La Rochetaillée'' Jean de Roquetaillade, also known as John of Rupescissa, (ca. 1310 – between 1366 and 1370) was a French Franciscan alchemist and eschatologist. Biography Af ...
(–1366), the latter of whom regarded it as a life-preserving substance able to prevent all diseases (the ''
aqua vitae ''Aqua vitae'' (Latin for "water of life") or aqua vita is an archaic name for a concentrated aqueous solution of ethanol. These terms could also be applied to weak ethanol without rectification. Usage was widespread during the Middle Ages a ...
'' or "water of life", also called by John the '' quintessence'' of wine). In
China China, officially the People's Republic of China (PRC), is a country in East Asia. It is the world's most populous country, with a population exceeding 1.4 billion, slightly ahead of India. China spans the equivalent of five time zones and ...
, archaeological evidence indicates that the true distillation of alcohol began during the Jin (1115–1234) or
Southern Song The Song dynasty (; ; 960–1279) was an Dynasties in Chinese history, imperial dynasty of China that began in 960 and lasted until 1279. The dynasty was founded by Emperor Taizu of Song following his usurpation of the throne of the Later Zhou. ...
(1127–1279) dynasties. A still has been found at an archaeological site in Qinglong,
Hebei Hebei or , (; alternately Hopeh) is a northern province of China. Hebei is China's sixth most populous province, with over 75 million people. Shijiazhuang is the capital city. The province is 96% Han Chinese, 3% Manchu, 0.8% Hui, an ...
, dating to the 12th century. In India, the true distillation of alcohol was introduced from the Middle East, and was in wide use in the
Delhi Sultanate The Delhi Sultanate was an Islamic empire based in Delhi that stretched over large parts of the Indian subcontinent for 320 years (1206–1526).
by the 14th century. In 1796, German-Russian chemist Johann Tobias Lowitz obtained pure ethanol by mixing partially purified ethanol (the alcohol-water azeotrope) with an excess of anhydrous alkali and then distilling the mixture over low heat. French chemist
Antoine Lavoisier Antoine-Laurent de Lavoisier ( , ; ; 26 August 17438 May 1794), When reduced without charcoal, it gave off an air which supported respiration and combustion in an enhanced way. He concluded that this was just a pure form of common air and th ...
described ethanol as a compound of carbon, hydrogen, and oxygen, and in 1807 Nicolas-Théodore de Saussure determined ethanol's chemical formula. Fifty years later,
Archibald Scott Couper Archibald Scott Couper (; 31 March 1831 – 11 March 1892) was a Scottish chemist who proposed an early theory of chemical structure and bonding. He developed the concepts of tetravalent carbon atoms linking together to form large molecules ...
published the structural formula of ethanol. It was one of the first structural formulas determined. Ethanol was first prepared synthetically in 1825 by
Michael Faraday Michael Faraday (; 22 September 1791 – 25 August 1867) was an English scientist who contributed to the study of electromagnetism and electrochemistry. His main discoveries include the principles underlying electromagnetic inducti ...
. He found that sulfuric acid could absorb large volumes of
coal gas Coal gas is a flammable gaseous fuel made from coal and supplied to the user via a piped distribution system. It is produced when coal is heated strongly in the absence of air. Town gas is a more general term referring to manufactured gaseous ...
. He gave the resulting solution to
Henry Hennell Henry Hennell FRS (''c.'' 1797 – 4 June 1842) was an English chemist. Hennelll was one of the founders of the Chemical Society of London and was a member of the first elected Council of the Chemical Society. He was elected F.R.S. in 1829. He w ...
, a British chemist, who found in 1826 that it contained "sulphovinic acid" ( ethyl hydrogen sulfate). In 1828, Hennell and the French chemist
Georges-Simon Serullas Georges-Simon Serullas (2 November 1774 in Poncin – 25 May 1832 in Paris) was a professor of pharmacy notable for being the first to publish a work on Iodoform, an early antiseptic and disinfectant. Biography He was a professor and head pharm ...
independently discovered that sulphovinic acid could be decomposed into ethanol. On page 368, Hennell produces ethanol from "sulfovinic acid" ( ethyl hydrogen sulfate). Thus, in 1825 Faraday had unwittingly discovered that ethanol could be produced from ethylene (a component of coal gas) by acid-catalyzed hydration, a process similar to current industrial ethanol synthesis.In 1855, the French chemist
Marcellin Berthelot Pierre Eugène Marcellin Berthelot (; 25 October 1827 – 18 March 1907) was a French chemist and Republican politician noted for the ThomsenBerthelot principle of thermochemistry. He synthesized many organic compounds from inorganic substance ...
confirmed Faraday's discovery by preparing ethanol from pure ethylene. (Note: The chemical formulas in Berthelot's paper are wrong because chemists at that time used the wrong atomic masses for the elements; e.g., carbon (6 instead of 12), oxygen (8 instead of 16), etc.)
Ethanol was used as lamp fuel in the U.S. as early as 1840, but a tax levied on industrial alcohol during the
Civil War A civil war or intrastate war is a war between organized groups within the same state (or country). The aim of one side may be to take control of the country or a region, to achieve independence for a region, or to change government policies ...
made this use uneconomical. The tax was repealed in 1906. Use as an automotive fuel dates back to 1908, with the
Ford Model T The Ford Model T is an automobile that was produced by Ford Motor Company from October 1, 1908, to May 26, 1927. It is generally regarded as the first affordable automobile, which made car travel available to middle-class Americans. The relati ...
able to run on
petrol Gasoline (; ) or petrol (; ) (see ) is a transparent, petroleum-derived flammable liquid that is used primarily as a fuel in most spark-ignited internal combustion engines (also known as petrol engines). It consists mostly of organic co ...
(gasoline) or ethanol. It fuels some
spirit lamps An alcohol burner or spirit lamp is a piece of laboratory equipment used to produce an open flame. It can be made from brass, glass, stainless steel or aluminium. Uses Alcohol burners are preferred for some uses over Bunsen burners for safety pu ...
. Ethanol intended for industrial use is often produced from ethylene. Ethanol has widespread use as a solvent of substances intended for human contact or consumption, including scents, flavorings, colorings, and medicines. In chemistry, it is both a solvent and a feedstock for the synthesis of other products. It has a long history as a fuel for heat and light, and more recently as a fuel for internal combustion engines.


See also

*
1-Propanol Propan-1-ol (also propanol, n-propyl alcohol) is a primary alcohol with the formula and sometimes represented as PrOH or ''n''-PrOH. It is a colorless liquid and an isomer of 2-propanol. It is formed naturally in small amounts during many ferme ...
*
Butanol fuel 220px, Butanol, a C-4 hydrocarbon is a promising bio-derived fuel, which shares many properties with gasoline. Butanol may be used as a fuel in an internal combustion engine. It is more similar to gasoline than it is to ethanol. A C4-hydrocarbon ...
*
Ethanol-induced non-lamellar phases in phospholipids The presence of ethanol can lead to the formations of non-lamellar phases also known as non-bilayer phases. Ethanol has been recognized as being an excellent solvent in an aqueous solution for inducing non-lamellar phases in phospholipids. The fo ...
*
Isopropyl alcohol Isopropyl alcohol (IUPAC name propan-2-ol and also called isopropanol or 2-propanol) is a colorless, flammable organic compound with a pungent alcoholic odor. As an isopropyl group linked to a hydroxyl group (chemical formula ) it is the simple ...
*
Rubbing alcohol Rubbing alcohol is either an isopropyl alcohol or an ethanol-based liquid, with isopropyl alcohol products being the most widely available. The comparable ''British Pharmacopoeia'' (''BP'') is surgical spirit. Rubbing alcohol is denatured and un ...
*
tert-Butyl alcohol ''tert''-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as ''t''-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. ''tert''-Butyl alcohol is a colorless solid, which melts near roo ...
*
Timeline of alcohol fuel Ethanol, an alcohol fuel, is an important fuel for the operation of internal combustion engines that are used in cars, trucks, and other kinds of machinery. * Ethanol was first isolated from wine in approximately 1100 and was found to burn shortl ...


References


Further reading

* . * * *


External links


Alcohol (Ethanol)
at ''
The Periodic Table of Videos ''Periodic Videos'' (also known as ''The Periodic Table of Videos'') is a video project and YouTube channel on chemistry. It consists of a series of videos about chemical elements and the periodic table, with additional videos on other topics i ...
'' (University of Nottingham)
International Labour Organization
ethanol safety information



* ttp://webbook.nist.gov/cgi/cbook.cgi?Name=ethanol&Units=SI National Institute of Standards and Technologychemical data on ethanol
Chicago Board of Trade
news and market data on ethanol futures * Calculation o
vapor pressureliquid densitydynamic liquid viscositysurface tension
of ethanol
Ethanol History
A look into the history of ethanol


Industrial ethanol production process flow diagram using ethylene and sulphuric acid
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