Ethanol, also called alcohol, ethyl alcohol, and drinking alcohol, is
a chemical compound, a simple alcohol with the chemical formula C
5OH. Its formula can be written also as CH
2−OH or C
5−OH (an ethyl group linked to a hydroxyl group), and is often
abbreviated as EtOH.
Ethanol is a volatile, flammable, colorless
liquid with a slight characteristic odor. It is a psychoactive
substance and is the principal type of alcohol found in alcoholic
Ethanol is naturally produced by the fermentation of sugars by yeasts
or via petrochemical processes, and is most commonly consumed as a
popular recreational drug. It also has medical applications as an
antiseptic and disinfectant. The compound is widely used as a chemical
solvent, either for scientific chemical testing or in synthesis of
other organic compounds, and is a vital substance utilized across many
different kinds of manufacturing industries.
Ethanol is also used as a
clean-burning fuel source.
2.1.3 Medicinal solvent
2.3.1 Engine fuel
2.3.4 Household heating
2.6 Low-temperature liquid
3.1 Chemical formula
3.2 Physical properties
4 Natural occurrence
5.2 From CO2
5.3 From lipids
Molecular sieves and desiccants
6.3 Membranes and reverse osmosis
6.4 Other techniques
6.5 Grades of ethanol
6.5.1 Denatured alcohol
6.5.2 Absolute alcohol
6.5.3 Rectified spirits
7.4 Acid-base chemistry
10 See also
12 Further reading
13 External links
Ethanol is the systematic name defined by the International Union of
Pure and Applied
Chemistry (IUPAC) for a compound consisting of alkyl
group with two carbon atoms (prefix “eth-”), having a single bond
between them (infix “-an-”), attached functional group −OH group
The “eth-” prefix and the qualifier “ethyl” in “ethyl
alcohol” originally come from the name “ethyl” assigned in 1834
to the group C
5− by Justus Liebig. He coined the word from the German name Aether
of the compound C
5 (commonly called “ether” in English, more specifically called
“diethyl ether”). According to the Oxford English Dictionary,
Ethyl is a contraction of the Ancient Greek αἰθήρ (aithḗr,
“upper air”) and the Greek word ὕλη (hýlē,
The name ethanol was coined as a result of a resolution 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
Oxford English Dictionary
Oxford English Dictionary claims that it is a medieval
loan from Arabic al-kuḥl, a powdered ore of antimony used since
antiquity as a cosmetic, and retained that meaning in Middle
Latin. The use of “alcohol” for ethanol (in full, “alcohol
of wine”) is modern, first recorded 1753, and by the later 17th
century referred to “any sublimated substance; distilled spirit”
use for “the spirit of wine” (shortened from a full expression
alcohol of wine). The systematic use in chemistry dates to 1850.
Main article: Short-term uses and function of alcohol
Ethanol is used in medical wipes and most common antibacterial hand
sanitizer gels as an antiseptic.
Ethanol kills organisms by denaturing
their proteins and dissolving their lipids and is effective against
most bacteria and fungi, and many viruses. However, ethanol is
ineffective against bacterial spores. 70% ethanol is the most
effective concentration, particularly because of osmotic pressure.
Absolute ethanol may inactivate microbes without destroying them
because the alcohol is unable to fully permeate the microbe's
Ethanol may be administered as an antidote to methanol and
ethylene glycol poisoning.
Ethanol, often in high concentrations, is used to dissolve many
water-insoluble medications and related compounds. Liquid preparations
of cough and cold remedies, pain medication, and mouth washes may be
dissolved in 1 to 25% concentrations of ethanol and may need to be
avoided in individuals with adverse reactions to ethanol such as
alcohol-induced respiratory reactions.
Ethanol is present mainly
as an antimicrobial preservative in over 700 liquid preparations of
medicine including acetaminophen, iron supplements, ranitidine,
furosemide, mannitol, phenobarbital, trimethoprim/sulfamethoxazole and
over-the-counter cough medicine.
Alcohol is extensively metabolized by the liver, particularly
via the enzyme CYP450. Ethyl
Alcohol increases the secretion of
acids in the stomach. The metabolite acetaldehyde is responsible
for much of the short term, and long term effects of ethyl alcohol
Alcohol (drug) and Alcoholic drink
As a central nervous system depressant, ethanol is one of the most
commonly consumed psychoactive drugs. It can lift mood, cause
feelings of euphoria, decrease anxiety, and increase sociability and
Energy content of some fuels compared with ethanol:
Dry wood (20% moisture)
(85% ethanol, 15% gasoline)
Liquefied natural gas
(60% propane + 40% butane)
(high-octane gasoline, not jet fuel)
(90% gasoline + 10% ethanol)
The largest single use of ethanol is as an engine fuel and fuel
Brazil in particular relies heavily upon the use of ethanol
as an engine fuel, due in part to its role as the globe's leading
producer of ethanol.
Gasoline sold in
Brazil contains at least 25%
anhydrous 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. Brazilian ethanol is produced from sugar cane and
noted for high carbon sequestration. The US and many other
countries primarily use E10 (10% ethanol, sometimes known as gasohol)
E85 (85% ethanol) ethanol/gasoline mixtures.
USP grade ethanol for laboratory use.
Ethanol has been used as rocket fuel and is currently in lightweight
rocket-powered racing aircraft.
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
According to an industry advocacy group, ethanol as a fuel reduces
harmful tailpipe emissions of carbon monoxide, particulate matter,
oxides of nitrogen, and other ozone-forming pollutants. Argonne
National Laboratory analyzed greenhouse gas emissions of many
different engine and fuel combinations, and found that
biodiesel/petrodiesel blend (B20) showed a reduction of 8%,
E85 ethanol blend a reduction of 17% and cellulosic
ethanol 64%, compared with pure gasoline.
Ethanol combustion in an internal combustion engine yields many of the
products of incomplete combustion produced by gasoline and
significantly larger amounts of formaldehyde and related species such
as acetaldehyde. This leads to a significantly larger
photochemical reactivity and more ground level ozone. These data
have 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 Localised 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
California Air Resources Board
California Air Resources Board formalized this
issue in 2008 by recognizing control standards for formaldehydes as an
emissions control group, much like the conventional
NOx and Reactive
Organic Gases (ROGs).
World production of ethanol in 2006 was 51 gigalitres
(1.3×1010 US gal), with 69% of the world supply coming from
Brazil and the United States. More than 20% of Brazilian cars are
able to use 100% ethanol as fuel, which includes ethanol-only engines
and flex-fuel engines. Flex-fuel engines in
Brazil are able to
work with all ethanol, all gasoline or any mixture of both. In the US
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 population of ethanol-burning automobiles with large
national infrastructure that produces ethanol from domestically grown
Sugar cane not only has a greater concentration of sucrose
than corn (by about 30%), but is also much easier to extract. The
bagasse generated by the process is not wasted, but is used in power
plants to produce electricity.
In the United States, the ethanol fuel industry is based largely on
corn. According to the Renewable Fuels Association, as of 30 October
2007, 131 grain ethanol bio-refineries in the United States have the
capacity to produce 7.0 billion US gallons (26,000,000 m3)
of ethanol per year. An additional 72 construction projects underway
(in the U.S.) can add 6.4 billion US gallons (24,000,000 m3)
of new capacity in the next 18 months. Over time, it is believed that
a material portion of the ≈150-billion-US-gallon
(570,000,000 m3) per year market for gasoline will begin to be
replaced with fuel ethanol.
Sweet sorghum is another potential source of ethanol, and is suitable
for growing in dryland conditions. The International Crops Research
Institute for the Semi-Arid Tropics (ICRISAT) is investigating the
possibility of growing sorgham as a source of fuel, food, and animal
feed in arid parts of
Asia and Africa.
Sweet sorghum has one-third
the water requirement of sugarcane over the same time period. It also
requires about 22% less water than corn (also known as maize). The
world’s first sweet sorghum ethanol distillery began commercial
production in 2007 in Andhra Pradesh, India.
Ethanol's high miscibility 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) and attribute the damage to the increased water retention
by ethanol in fuel.
Ethanol pump station in São Paulo, Brazil
Ford Taurus fueled by ethanol in New York City
USPS truck running on
E85 in Minnesota
Ethanol was commonly used as fuel in early bipropellant rocket (liquid
propelled) vehicles, in conjunction with an oxidizer such as liquid
oxygen. The German
V-2 rocket of World War II, credited with beginning
the space age, used ethanol, mixed with 25% of water to reduce the
combustion chamber temperature. The V-2's design team helped
develop U.S. rockets following World War II, including the
ethanol-fueled Redstone rocket which launched the first U.S.
satellite. Alcohols fell into general disuse as more efficient
rocket fuels were developed.
Commercial fuel cells operate on reformed natural gas, hydrogen or
Ethanol is an attractive alternative due to its wide
availability, low cost, high purity and low toxicity. There are a wide
range of fuel cell concepts that have been trialled including
direct-ethanol fuel cells, 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 commercialization of ethanol fuel cells.
Ethanol fireplaces can be used for home heating or for decoration.
Further information: § Reactions
Ethanol is an important industrial ingredient. It has widespread use
as a precursor for other organic compounds such as ethyl halides,
ethyl esters, diethyl ether, acetic acid, and ethyl amines.
Ethanol is miscible with water and is a good general purpose solvent.
It is found in paints, tinctures, markers, and personal care products
such as mouthwashes, perfumes and deodorants. However, polysaccharides
precipitate from aqueous solution in the presence of alcohol, and
ethanol precipitation is used for this reason in the purification of
DNA and RNA.
Because of its low melting point (−114.14 °C) and low
toxicity, ethanol is sometimes used in laboratories (with dry ice or
other coolants) as a cooling bath 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 thermometers.
Ethanol (data page)
Ethanol is a 2-carbon alcohol. Its molecular formula is CH3CH2OH. An
alternative notation is CH3−CH2−OH, which indicates that the
carbon of a methyl group (CH3−) is attached to the carbon of a
methylene group (−CH2–), which is attached to the oxygen of a
hydroxyl group (−OH). It is a constitutional isomer of dimethyl
Ethanol is sometimes abbreviated as EtOH, using the common
organic chemistry notation of representing the ethyl group (C2H5−)
Ethanol burning with its spectrum depicted
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.
Ethanol is slightly more refractive than water, having a refractive
index of 1.36242 (at λ=589.3 nm and 18.35 °C or
65.03 °F). The triple point for ethanol is 150 K at a
pressure of 4.3 × 10−4 Pa.
Ethanol is a versatile solvent, miscible with water and with many
organic solvents, including acetic acid, acetone, benzene, carbon
tetrachloride, chloroform, diethyl ether, ethylene glycol, glycerol,
nitromethane, pyridine, and toluene. It is also miscible with
light aliphatic hydrocarbons, such as pentane and hexane, and with
aliphatic chlorides such as trichloroethane and
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 alkanes is limited to alkanes up to
undecane: mixtures with dodecane and higher alkanes show a miscibility
gap 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, with up to 777 J/mol
being released at 298 K.
Mixtures of ethanol and water form an azeotrope 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) at normal pressure, which
boils at 351K (78 °C). This azeotropic composition is strongly
temperature- and pressure-dependent and vanishes at temperatures below
Hydrogen bonding in solid ethanol at −186 °C
Hydrogen bonding causes pure ethanol to be hygroscopic 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 and potassium hydroxides, magnesium chloride, calcium
chloride, ammonium chloride, ammonium bromide, and sodium bromide.
Sodium and potassium chlorides are slightly soluble in ethanol.
Because the ethanol molecule also has a nonpolar end, it will also
dissolve nonpolar substances, including most essential oils and
numerous flavoring, coloring, and medicinal agents.
The addition of even a few percent of ethanol to water sharply reduces
the surface tension of water. This property partially explains the
"tears of wine" 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.
An ethanol-water solution that contains 40% alcohol by weight (about
56% by volume) will catch fire if heated to about 26 °C
(79 °F) and if an ignition source is applied to it. This is
called its flash point. The flash point of pure ethanol is
16.60 °C (61.88 °F), less than average room temperature.
The flash points of ethanol wt % concentrations
49 °C (120 °F)
36 °C (97 °F)
29 °C (84 °F)
26 °C (79 °F)
24 °C (75 °F)
22 °C (72 °F)
21 °C (70 °F)
20 °C (68 °F)
17 °C (63 °F)
17 °C (63 °F)
Dishes using burning alcohol for culinary effects are called Flambé.
Ethanol is a byproduct of the metabolic process 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 anerobiosis.
Ethanol has been detected in outer
space, forming an icy coating around dust grains in interstellar
clouds. Minute quantity amounts (average 196 ppb) of endogenous
ethanol and acetaldehyde were found in the exhaled breath of healthy
volunteers. Auto-brewery syndrome, also known as gut fermentation
syndrome, is a rare medical condition in which intoxicating quantities
of ethanol are produced through endogenous fermentation within the
94% denatured ethanol sold in a bottle for household use
Ethanol is produced both as a petrochemical, through the hydration of
ethylene and, via biological processes, by fermenting sugars with
yeast. Which process is more economical depends on prevailing
prices of petroleum and grain feed stocks. In the 1970s most
industrial ethanol in the United States was made as a petrochemical,
but in the 1980s the United States introduced subsidies for corn based
ethanol and today it is almost all made from that source.
Ethanol for use as an industrial feedstock or solvent (sometimes
referred to as synthetic ethanol) is made from petrochemical feed
stocks, primarily by the acid-catalyzed hydration of ethylene:
4 + H
2O → CH
The catalyst is most commonly phosphoric acid, adsorbed onto a
porous support such as silica gel or diatomaceous earth. This catalyst
was first used for large-scale ethanol production by the Shell Oil
Company in 1947. The reaction is carried out in the presence of
high pressure steam at 300 °C (572 °F) where a 5:3
ethylene to steam ratio is maintained. In the U.S., this
process was used on an industrial scale by
Union Carbide Corporation
and others, but now only
LyondellBasell uses it commercially.
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 to
produce ethyl sulfate, which was hydrolyzed to yield ethanol and
regenerate the sulfuric acid:
4 + H
4 → CH
4H + H
2O → CH
2OH + H
CO2 can also be used as the raw material.
CO2 can be converted using such organisms as Clostridium ljungdahlii,
Clostridium autoethanogenum or Moorella sp. HUC22-1.
CO2 can be converted using electrochemical reactions at room
temperature and pressure.
Lipids can also be used to make ethanol and can be found in such raw
materials such as algae.
Yeast in winemaking
Ethanol in alcoholic beverages and fuel is produced by fermentation.
Certain species of yeast (e.g., Saccharomyces cerevisiae) metabolize
sugar, producing ethanol and carbon dioxide. The chemical equations
below summarize the conversion:
6 → 2 CH
2OH + 2 CO2
11 + H
2O → 4 CH
2OH + 4 CO2
Fermentation is the process of culturing yeast under favorable thermal
conditions to produce alcohol. This process is carried out at around
35–40 °C (95–104 °F). Toxicity of ethanol to yeast
limits the ethanol concentration obtainable by brewing; higher
concentrations, therefore, are obtained by fortification or
distillation. The most ethanol-tolerant yeast strains can survive up
to approximately 18% ethanol by volume.
To produce ethanol from starchy materials such as cereal grains, the
starch must first be converted into sugars. In brewing beer, this has
traditionally been accomplished by allowing the grain to germinate, or
malt, which produces the enzyme amylase. When the malted grain is
mashed, the amylase converts the remaining starches into sugars.
Main article: Cellulosic ethanol
Sugars for ethanol fermentation can be obtained from cellulose.
Deployment of this technology could turn a number of
cellulose-containing agricultural by-products, such as corncobs,
straw, and sawdust, into renewable energy resources. Other
agricultural residues such as sugar cane bagasse and energy crops such
as switchgrass may also be a sources of fermentable sugars.
Infrared reflection spectra of liquid ethanol, showing the -OH band
centered at ≈3300 cm−1 and C-H bands at ≈2950 cm−1.
Near infrared spectrum
Near infrared spectrum of liquid ethanol.
Breweries and biofuel plants employ two methods for measuring ethanol
concentration. Infrared ethanol sensors measure the vibrational
frequency of dissolved ethanol using the CH band at 2900 cm−1.
This method uses a relatively inexpensive solid state sensor that
compares the CH band with a reference band to calculate the ethanol
content. The calculation makes use of the Beer-Lambert law.
Alternatively, by measuring the density of the starting material and
the density of the product, using 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
Ethylene hydration or brewing produces an ethanol–water mixture. For
most industrial and fuel uses, the ethanol must be purified.
Fractional distillation at atmospheric pressure can concentrate
ethanol to 95.6% by weight (89.5 mole%). This mixture is an azeotrope
with a boiling point of 78.1 °C (172.6 °F), and cannot be
further purified by distillation. Addition of an entraining agent,
such as benzene, cyclohexane, or heptane, 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.
At pressures less than atmospheric pressure, the composition of the
ethanol-water azeotrope shifts to more ethanol-rich mixtures, and at
pressures less than 70 torr (9.333 kPa), there is no
azeotrope, and it is possible to distill absolute ethanol from an
ethanol-water mixture. While vacuum distillation of ethanol is not
presently economical, pressure-swing distillation is a topic of
current research. In this technique, a reduced-pressure distillation
first yields an ethanol-water mixture of more than 95.6% ethanol.
Then, fractional distillation of this mixture at atmospheric pressure
distills off the 95.6% azeotrope, leaving anhydrous ethanol at the
Molecular sieves and desiccants
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Apart from distillation, ethanol may be dried by addition of a
desiccant, such as molecular sieves, cellulose, and cornmeal. The
desiccants can be dried and reused.
Molecular sieves can be used
to selectively absorb the water from the 95.6% ethanol solution.
Synthetic zeolite in pellet form can be used, as well as a variety of
plant-derived absorbents, including cornmeal, straw, and sawdust. The
zeolite bed can be regenerated essentially an unlimited number of
times by drying it with a blast of hot carbon dioxide.
other plant-derived absorbents cannot readily be regenerated, but
where ethanol is made from grain, they are often available at low
cost. Absolute ethanol produced this way has no residual benzene, and
can be used to fortify port and sherry in traditional winery
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 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
A variety of other techniques have been discussed, including the
Salting using potassium carbonate 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 with water.
Direct electrochemical reduction of carbon dioxide to ethanol under
ambient conditions using copper nanoparticles on a carbon nanospike
film as the catalyst;
Extraction of ethanol from grain mash by supercritical carbon dioxide;
Fractional freezing is also used to concentrate fermented alcoholic
solutions, such as traditionally made Applejack (beverage);
Pressure swing adsorption.
Grades of ethanol
Main article: Denatured alcohol
Pure ethanol and alcoholic beverages are heavily taxed 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 and
toxins such as methanol, naphtha, and pyridine. Products of this kind
are called denatured 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) levels. If azeotropic
distillation 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 and
visible light, fit for use as a solvent in ultraviolet-visible
Pure ethanol is classed as 200 proof in the U.S., equivalent to 175
degrees proof in the UK system.
Rectified spirit, an azeotropic composition of 96% ethanol containing
4% water, is used instead of anhydrous ethanol for various purposes.
Wine spirits are about 94% ethanol (188 proof). The impurities are
different from those in 95% (190 proof) laboratory ethanol.
Further information: Alcohol
Ethanol is classified as a primary alcohol, meaning that the carbon
its hydroxyl group attaches to has at least two hydrogen atoms
attached to it as well. Many ethanol reactions occur at its hydroxyl
In the presence of acid catalysts, ethanol reacts with carboxylic
acids to produce ethyl esters and water:
RCOOH + HOCH2CH3 → RCOOCH2CH3 + 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
because it is used in the preparation of soap.
Ethanol can also form
esters with inorganic acids.
Diethyl sulfate and triethyl phosphate
are prepared by treating ethanol with sulfur trioxide and phosphorus
Diethyl sulfate is a useful ethylating agent
in organic synthesis. Ethyl nitrite, prepared from the reaction of
ethanol with sodium nitrite and sulfuric acid, was formerly used as a
Strong acid desiccants cause the partial dehydration of ethanol to
form diethyl ether and other byproducts. If the dehydration
temperature exceeds around 160 °C (320 °F), full
dehydration will occur and ethylene will be the main product.
2 CH3CH2OH → CH3CH2OCH2CH3 +
H2O (ca. 120 °C)
CH3CH2OH → H2C=CH2 +
H2O (above 160 °C)
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 =
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
Specific heat = 2.44 kJ/(kg·K)
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, the ethoxide ion (CH3CH2O−), by reaction with an
alkali metal such as sodium:
2 CH3CH2OH + 2 Na → 2 CH3CH2ONa + H2
or a very strong base such as sodium hydride:
CH3CH2OH + NaH → CH3CH2ONa + H2
The acidity of water and ethanol are nearly the same, as indicated by
their pKa of 15.7 and 16 respectively. Thus, sodium ethoxide and
sodium hydroxide exist in an equilibrium that is closely balanced:
CH3CH2OH + NaOH ⇌ CH3CH2ONa + H2O
Ethanol is not used industrially as a precursor to ethyl halides, but
the reactions are illustrative.
Ethanol reacts with hydrogen halides
to produce ethyl halides such as ethyl chloride and ethyl bromide via
an SN2 reaction:
CH3CH2OH + HCl → CH3CH2Cl + H2O
These reactions require a catalyst such as zinc chloride. HBr
requires refluxing with a sulfuric acid catalyst. Ethyl halides
can, in principle, also be produced by treating ethanol with more
specialized halogenating agents, such as thionyl chloride or
CH3CH2OH + SOCl2 → CH3CH2Cl + SO2 + HCl
Upon treatment with halogens in the presence of base, ethanol gives
the corresponding haloform (CHX3, where X = Cl, Br, I). This
conversion is called the haloform reaction. " An intermediate in
the reaction with chlorine is the aldehyde called chloral, which forms
chloral hydrate upon reaction with water:
4 Cl2 + CH3CH2OH → CCl3CHO + 5 HCl
H2O → CCl3C(OH)2H
Ethanol can be oxidized to acetaldehyde and further oxidized to acetic
acid, 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 liver alcohol dehydrogenase. The
oxidation product of ethanol, acetic acid, is a nutrient for humans,
being a precursor to acetyl CoA, where the acetyl group can be spent
as energy or used for biosynthesis.
Alcohol § Toxicity
Pure ethanol will irritate the skin and eyes. Nausea, vomiting,
and intoxication are symptoms of ingestion. Long-term use by ingestion
can result in serious liver damage. Atmospheric concentrations
above one in a thousand are above the European Union occupational
Further information: Distilled beverage
The fermentation of sugar into ethanol is one of the earliest
biotechnologies employed by humans. The intoxicating effects of
ethanol consumption have been known since ancient times.
been used by humans since prehistory as the intoxicating ingredient of
alcoholic beverages. Dried residue on 9,000-year-old pottery found in
China suggests that
Neolithic people consumed alcoholic beverages.
The medieval Muslims used the distillation process extensively, and
applied it to the distillation of alcohol. The Arab chemist Al-Kindi
unambiguously described the distillation of wine in the 9th
century. The process later spread from the
Middle East to
Italy. Production of alcohol from distilled wine was later
recorded by the School of Salerno alchemists in the 12th century.
Mention of absolute alcohol, in contrast with alcohol-water mixtures,
was later made by Raymond Lull in the 14th century.
In China, archaeological evidence indicates that the true distillation
of alcohol began during the 12th century Jin or Southern Song
dynasties. A still has been found at an archaeological site in
Qinglong, Hebei, 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 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 described
ethanol as a compound of carbon, hydrogen, and oxygen, and in 1807
Nicolas-Théodore de Saussure
Nicolas-Théodore de Saussure determined ethanol's chemical
formula. Fifty years later,
Archibald Scott Couper
Archibald Scott Couper published
the structural formula of ethanol. It was one of the first structural
Ethanol was first prepared synthetically in 1825 by Michael Faraday.
He found that sulfuric acid could absorb large volumes of coal
gas. He gave the resulting solution to Henry Hennell, 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 independently discovered that sulphovinic acid
could be decomposed into ethanol. 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.
Ethanol was used as lamp fuel in the United States as early as 1840,
but a tax levied on industrial alcohol during the Civil War made this
use uneconomical. The tax was repealed in 1906. Use as an
automotive fuel dates back to 1908, with the
Ford Model T
Ford Model T able to run
on petrol (gasoline) or ethanol. It fuels some spirit lamps.
Ethanol intended for industrial use is often produced from
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.
Cellulosic ethanol commercialization
Ethanol-induced non-lamellar phases in phospholipids
Timeline of alcohol fuel
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Look up alcohol or ethanol in Wiktionary, the free dictionary.
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