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Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic
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
formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...
C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a light, volatile, colourless,
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 ...
liquid with a distinctive alcoholic odour similar to that of
ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a ...
(potable alcohol). A polar solvent, methanol acquired the name wood alcohol because it was once produced chiefly by the
destructive distillation Destruction may refer to: Concepts * Destruktion, a term from the philosophy of Martin Heidegger * Destructive narcissism, a pathological form of narcissism * Self-destructive behaviour, a widely used phrase that ''conceptualises'' certain kin ...
of
wood Wood is a porous and fibrous structural tissue found in the stems and roots of trees and other woody plants. It is an organic materiala natural composite of cellulose fibers that are strong in tension and embedded in a matrix of lignin ...
. Today, methanol is mainly produced industrially by
hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organic ...
of
carbon monoxide Carbon monoxide ( chemical formula CO) is a colorless, poisonous, odorless, tasteless, flammable gas that is slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the simp ...
. Methanol consists of a methyl group linked to a polar hydroxyl group. With more than 20 million tons produced annually, it is used as a precursor to other
commodity chemicals Commodity chemicals (or bulk commodities or bulk chemicals) are a group of chemicals that are made on a very large scale to satisfy global markets. The average prices of commodity chemicals are regularly published in the chemical trade magazines an ...
, including formaldehyde,
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 compon ...
,
methyl tert-butyl ether Methyl ''tertiary''-butyl ether (MTBE), also known as methyl tert-butyl ether and ''tert''-butyl methyl ether, is an organic compound with a structural formula (CH3)3COCH3. MTBE is a volatile, flammable, and colorless liquid that is sparingly sol ...
, methyl benzoate,
anisole Anisole, or methoxybenzene, is an organic compound with the formula CH3OC6H5. It is a colorless liquid with a smell reminiscent of anise seed, and in fact many of its derivatives are found in natural and artificial fragrances. The compound is m ...
, peroxyacids, as well as a host of more specialised chemicals.


Occurrence

Small amounts of methanol are present in normal, healthy human individuals. One study found a mean of 4.5  ppm in the exhaled breath of test subjects. The mean endogenous methanol in humans of 0.45 g/d may be metabolized from pectin found in fruit; one kilogram of apple produces up to 1.4 g of pectin (0.6 g of methanol.) Methanol is produced by
anaerobic bacteria An anaerobic organism or anaerobe is any organism that does not require molecular oxygen for growth. It may react negatively or even die if free oxygen is present. In contrast, an aerobic organism (aerobe) is an organism that requires an oxygenat ...
and
phytoplankton Phytoplankton () are the autotrophic (self-feeding) components of the plankton community and a key part of ocean and freshwater ecosystems. The name comes from the Greek words (), meaning 'plant', and (), meaning 'wanderer' or 'drifter'. Ph ...
.


Interstellar medium

Methanol is also found in abundant quantities in star-forming regions of space and is used in astronomy as a marker for such regions. It is detected through its spectral emission lines. In 2006, astronomers using the
MERLIN Merlin ( cy, Myrddin, kw, Marzhin, br, Merzhin) is a mythical figure prominently featured in the legend of King Arthur and best known as a mage, with several other main roles. His usual depiction, based on an amalgamation of historic and le ...
array of radio telescopes at
Jodrell Bank Observatory Jodrell Bank Observatory () in Cheshire, England, hosts a number of radio telescopes as part of the Jodrell Bank Centre for Astrophysics at the University of Manchester. The observatory was established in 1945 by Bernard Lovell, a radio astr ...
discovered a large cloud of methanol in space across. In 2016, astronomers detected methanol in a planet-forming disc around the young star TW Hydrae using the Atacama Large Millimeter Array radio telescope.


Safety

Methanol is highly flammable. Its vapours are slightly heavier than air, can travel and ignite. Methanol fires should be extinguished with dry chemical,
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 tran ...
, water spray or alcohol-resistant foam.


Toxicity

Ingesting as little as of pure methanol can cause permanent blindness by destruction of the optic nerve. is potentially fatal. The median lethal dose is , ''i.e.'', 1–2 mL/kg body weight of pure methanol. The reference dose for methanol is 0.5 mg/kg in a day. Toxic effects begin hours after ingestion, and antidotes can often prevent permanent damage. Because of its similarities in both appearance and odor to
ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a ...
(the alcohol in beverages), it is difficult to differentiate between the two; such is also the case with denatured alcohol, adulterated liquors or very low quality alcoholic beverages. Methanol is
toxic Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a subst ...
by two mechanisms. First, methanol can be fatal due to effects on the central nervous system, acting as a central nervous system depressant in the same manner as ethanol poisoning. Second, in a process of toxication, it is metabolised to
formic acid Formic acid (), systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH and structure . It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Est ...
(which is present as the formate ion) via formaldehyde in a process initiated 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 product ...
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 NAD ...
in the
liver The liver is a major organ only found in vertebrates which performs many essential biological functions such as detoxification of the organism, and the synthesis of proteins and biochemicals necessary for digestion and growth. In humans, it ...
. Methanol is converted to formaldehyde via alcohol dehydrogenase (ADH) and formaldehyde is converted to formic acid (formate) via
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). The conversion to formate via ALDH proceeds completely, with no detectable formaldehyde remaining. Formate is toxic because it inhibits mitochondrial cytochrome c oxidase, causing hypoxia at the cellular level, and metabolic acidosis, among a variety of other metabolic disturbances. Outbreaks of methanol poisoning have occurred primarily due to contamination of drinking alcohol. This is more common in the developing world. In 2013 more than 1700 cases nonetheless occurred in the United States. Those affected are often adult men. Outcomes may be good with early treatment. Toxicity to methanol was described as early as 1856. Because of its toxic properties, methanol is frequently used as a denaturant additive for ethanol manufactured for industrial uses. This addition of methanol exempts industrial ethanol (commonly known as " denatured alcohol" or "methylated spirit") from liquor excise taxation in the U.S. and other countries. During the course of the
COVID-19 pandemic The COVID-19 pandemic, also known as the coronavirus pandemic, is an ongoing global pandemic of coronavirus disease 2019 (COVID-19) caused by severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). The novel virus was first identif ...
, the U.S.
Food and Drug Administration The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food ...
(FDA) found a number of hand sanitizer products being sold that were labeled as containing
ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a ...
but tested positive for methanol contamination. Due to the toxic effects of methanol when absorbed through the skin or ingested, in contrast to the relatively safer ethanol, the FDA ordered recalls of such hand sanitizer products containing methanol, and issued an import alert to stop these products from illegally entering the U.S. market.


Applications


Formaldehyde, acetic acid, methyl ''tert''-butylether

Methanol is primarily converted to formaldehyde, which is widely used in many areas, especially polymers. The conversion entails oxidation: :2 CH3OH + O2 -> 2 CH2O + 2 H2O
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 compon ...
can be produced from methanol. Methanol and
isobutene Isobutylene (or 2-methylpropene) is a hydrocarbon with the chemical formula . It is a four-carbon branched alkene (olefin), one of the four isomers of butylene. It is a colorless flammable gas, and is of considerable industrial value. Producti ...
are combined to give methyl ''tert''-butyl ether (MTBE). MTBE is a major octane booster in gasoline.


Methanol to hydrocarbons, olefins, gasoline

Condensation of methanol to produce
hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic In chemistry, hydrophobicity ...
s and even aromatic systems is the basis of several technologies related to gas to liquids. These include methanol-to-hydrocarbons (MtH), methanol to gasoline (MtG), methanol to olefins (MtO), and methanol to propylene (MtP). These conversions are catalyzed by
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 po ...
s as heterogeneous catalysts. The MtG process was once commercialized at Motunui in New Zealand.


Gasoline additive

The European Fuel Quality Directive allows fuel producers to blend up to 3% methanol, with an equal amount of cosolvent, with gasoline sold in Europe.
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 an ...
uses more than 4.5 billion liters of methanol per year as a transportation fuel in low level blends for conventional vehicles, and high level blends in vehicles designed for methanol fuels. In recent years, however, most modern gasoline-using vehicles can use a variety of alcohol fuels, resulting in similar or higher horsepower, but for a simple change in the vehicle's software settings and possibly a 50 cent seal or tube part.


Other chemicals

Methanol is the precursor to most simple
methylamine Methylamine is an organic compound with a formula of . This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine. Methylamine is sold as a solution in methanol, e ...
s, methyl halides, and methyl ethers. Methyl esters are produced from methanol, including the transesterification of fats and production of
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 wit ...
via
transesterification In organic chemistry, transesterification is the process of exchanging the organic group R″ of an ester with the organic group R' of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst. The reaction ca ...
.


Niche and potential uses


Energy carrier

Methanol is a promising energy carrier because, as a liquid, it is easier to store than hydrogen and natural gas. Its
energy density In physics, energy density is the amount of energy stored in a given system or region of space per unit volume. It is sometimes confused with energy per unit mass which is properly called specific energy or . Often only the ''useful'' or extra ...
is, however, lower than methane, per kg. Its combustion energy density is 15.6 MJ/ L ( LHV), whereas that of ethanol is 24 and gasoline is 33 MJ/L. Further advantages for methanol is its ready biodegradability and low environmental toxicity. It does not persist in either aerobic (oxygen-present) or anaerobic (oxygen-absent) environments. The half-life for methanol in groundwater is just one to seven days, while many common gasoline components have half-lives in the hundreds of days (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 ato ...
at 10–730 days). Since methanol is
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 biodegradable, it is unlikely to accumulate in groundwater, surface water, air or soil.


Fuel

Methanol is occasionally used to fuel
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 combust ...
s. It burns forming carbon dioxide and water: : 2 CH3OH + 3 O2 -> 2 CO2 + 4 H2O Methanol fuel has been proposed for ground transportation. The chief advantage of a methanol economy is that it could be adapted to gasoline internal combustion engines with minimum modification to the engines and to the infrastructure that delivers and stores liquid fuel. Its energy density, however, is less than gasoline, meaning more frequent fill ups would be required. However, it is equivalent to super high-octane gasoline in horsepower, and most modern computer-controlled fuel injection systems can already use it. Methanol is an alternative fuel for ships that helps the shipping industry meet increasingly strict emissions regulations. It significantly reduces emissions of sulphur oxides (SOx), nitrogen oxides (NOx) and particulate matter. Methanol can be used with high efficiency in marine diesel engines after minor modifications using a small amount of pilot fuel (Dual fuel). In China, methanol fuels industrial boilers, which are used extensively to generate heat and steam for various industrial applications and residential heating. Its use is displacing coal, which is under pressure from increasingly stringent environmental regulations. Direct-methanol fuel cells are unique in their low temperature, atmospheric pressure operation, which lets them be greatly miniaturized. This, combined with the relatively easy and safe storage and handling of methanol, may open the possibility of fuel cell-powered consumer electronics, such as laptop computers and mobile phones. Methanol is also a widely used fuel in camping and boating stoves. Methanol burns well in an unpressurized burner, so alcohol stoves are often very simple, sometimes little more than a cup to hold fuel. This lack of complexity makes them a favorite of hikers who spend extended time in the wilderness. Similarly, the alcohol can be gelled to reduce risk of leaking or spilling, as with the brand " Sterno". Methanol is mixed with water and injected into high performance diesel and gasoline engines for an increase of power and a decrease in intake air temperature in a process known as water methanol injection.


Other applications

Methanol is used as a denaturant for ethanol, the product being known as "denatured alcohol" or "methylated spirit". This was commonly used during the U.S. prohibition to discourage consumption of bootlegged liquor, and ended up causing several deaths. These types of practices are now illegal in the U.S., being considered homicide. Methanol is used as a
solvent A solvent (s) (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a ...
and as an antifreeze in pipelines and windshield washer fluid. Methanol was used as an automobile coolant antifreeze in the early 1900s. As of May 2018, methanol was banned in the EU for use in windscreen washing or defrosting due to its risk of human consumption as a result of 2012 Czech Republic methanol poisonings. In some
wastewater treatment plants Wastewater treatment is a process used to remove contaminants from wastewater and convert it into an effluent that can be returned to the water cycle. Once returned to the water cycle, the effluent creates an acceptable impact on the environme ...
, a small amount of methanol is added to wastewater to provide a carbon food source for the denitrifying bacteria, which convert
nitrate Nitrate is a polyatomic ion with the chemical formula . Salts containing this ion are called nitrates. Nitrates are common components of fertilizers and explosives. Almost all inorganic nitrates are soluble in water. An example of an insolubl ...
s to nitrogen gas and reduce the nitrification of sensitive aquifers. Methanol is used as a destaining agent in polyacrylamide gel electrophoresis.


Production


From synthesis gas

Carbon monoxide and hydrogen react over a catalyst to produce methanol. Today, the most widely used catalyst is a mixture of copper and
zinc oxide Zinc oxide is an inorganic compound with the formula . It is a white powder that is insoluble in water. ZnO is used as an additive in numerous materials and products including cosmetics, food supplements, rubbers, plastics, ceramics, glass, cement ...
s, supported on alumina, as first used by ICI in 1966. At 5–10 MPa (50–100 atm) and , the reaction :CO + 2 H2 -> CH3OH is characterized by high selectivity (>99.8%). The production of synthesis gas from methane produces three moles of hydrogen for every mole of carbon monoxide, whereas the synthesis consumes only two moles of hydrogen gas per mole of carbon monoxide. One way of dealing with the excess hydrogen is to inject
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 tran ...
into the methanol synthesis reactor, where it, too, reacts to form methanol according to the equation :CO2 + 3 H2 -> CH3OH + H2O. In terms of mechanism, the process occurs via initial conversion of CO into CO2, which is then hydrogenated: :CO2 + 3 H2 -> CH3OH + H2O where the H2O byproduct is recycled via the water-gas shift reaction :CO + H2O -> CO2 + H2. This gives an overall reaction :CO + 2 H2 -> CH3OH, which is the same as listed above. In a process closely related to methanol production from synthesis gas, a feed of hydrogen and CO2 can be used directly. The main advantage of this process is that captured CO2 and hydrogen sourced from
electrolysis In chemistry and manufacturing, electrolysis is a technique that uses direct electric current (DC) to drive an otherwise non-spontaneous chemical reaction. Electrolysis is commercially important as a stage in the separation of elements from n ...
could be used, removing the dependence on fossil fuels.


Biosynthesis

The catalytic conversion of methane to methanol is effected by enzymes including methane monooxygenases. These enzymes are mixed-function oxygenases, i.e. oxygenation is coupled with production of water and NAD+: :CH4 + O2 + NADPH + H^+ -> CH3OH + H2O + NAD^+ . Both Fe- and Cu-dependent enzymes have been characterized. Intense but largely fruitless efforts have been undertaken to emulate this reactivity. Methanol is more easily oxidized than is the feedstock methane, so the reactions tend not to be selective. Some strategies exist to circumvent this problem. Examples include Shilov systems and Fe- and Cu containing zeolites. These systems do not necessarily mimic the mechanisms employed by metalloenzymes, but draw some inspiration from them. Active sites can vary substantially from those known in the enzymes. For example, a dinuclear active site is proposed in the sMMO enzyme, whereas a mononuclear iron ( alpha-oxygen) is proposed in the Fe-zeolite. Global emissions of methanol by plants are estimated at between 180 and 250 million tons per year. This is between two and three times larger than man-made industrial production of methanol.


Quality specifications and analysis

Methanol is available commercially in various purity grades. Commercial methanol is generally classified according to ASTM purity grades A and AA. Both grade A and grade AA purity are 99.85% methanol by weight. Grade "AA" methanol contains trace amounts of ethanol as well. Methanol for chemical use normally corresponds to Grade AA. In addition to water, typical impurities include acetone and ethanol (which are very difficult to separate by distillation). UV-vis spectroscopy is a convenient method for detecting aromatic impurities. Water content can be determined by the Karl-Fischer titration.


History

In their
embalming Embalming is the art and science of preserving human remains by treating them (in its modern form with chemicals) to forestall decomposition. This is usually done to make the deceased suitable for public or private viewing as part of the funeral ...
process, the ancient Egyptians used a mixture of substances, including methanol, which they obtained from the
pyrolysis The pyrolysis (or devolatilization) process is the thermal decomposition of materials at elevated temperatures, often in an inert atmosphere. It involves a change of chemical composition. The word is coined from the Greek-derived elements ''p ...
of wood. Pure methanol, however, was first isolated in 1661 by Robert Boyle, when he produced it via the distillation of
buxus ''Buxus'' is a genus of about seventy species in the family Buxaceae. Common names include box or boxwood. The boxes are native to western and southern Europe, southwest, southern and eastern Asia, Africa, Madagascar, northernmost Sou ...
(boxwood). It later became known as "pyroxylic spirit". In 1834, the French chemists
Jean-Baptiste Dumas Jean Baptiste André Dumas (14 July 180010 April 1884) was a French chemist, best known for his works on organic analysis and synthesis, as well as the determination of atomic weights (relative atomic masses) and molecular weights by measuring v ...
and
Eugene Peligot Eugene may refer to: People and fictional characters * Eugene (given name), including a list of people and fictional characters with the given name * Eugene (actress) (born 1981), Kim Yoo-jin, South Korean actress and former member of the si ...
determined its elemental composition.A report on methanol to the French Academy of Sciences by J. Dumas and E. Péligot began during the Academy's meeting of 27 October 1834 and finished during the meeting of 3 November 1834. See: ''Procès-verbaux des séances de l'Académie'', 10 : 600–601. Available on:
Gallica
The complete report appears in: J. Dumas and E. Péligot (1835) "Mémoire sur l'espirit de bois et sur les divers composés ethérés qui en proviennent"(Memoir on spirit of wood and on the various ethereal compounds that derive therefrom), ''Annales de chimie et de physique'', 58 : 5–74; from page 9 ''Nous donnerons le nom de ''méthylène'' (1) à un radical ... (1) Μεθυ, vin, et υλη, bois; c'est-à-dire vin ou liqueur spiritueuse du bois.'' (We will give the name methylene (1) to a radical ... (1) ''methy'', wine, and ''hulē'', wood; that is, wine or spirit of wood.)
They also introduced the word "methylène" to organic chemistry, forming it from
Greek Greek may refer to: Greece Anything of, from, or related to Greece, a country in Southern Europe: *Greeks, an ethnic group. *Greek language, a branch of the Indo-European language family. **Proto-Greek language, the assumed last common ancestor ...
''methy'' = "alcoholic liquid" + '' hȳlē'' = "forest, wood, timber, material". "Methylène" designated a "radical" that was about 14% hydrogen by weight and contained one carbon atom. This would be CH2, but at the time carbon was thought to have an
atomic weight Relative atomic mass (symbol: ''A''; sometimes abbreviated RAM or r.a.m.), also known by the deprecated synonym atomic weight, is a dimensionless physical quantity defined as the ratio of the average mass of atoms of a chemical element in a giv ...
only six times that of hydrogen, so they gave the formula as CH. They then called wood alcohol (l'esprit de bois) "bihydrate de méthylène" (bihydrate because they thought the formula was C4H8O4 = (CH)4(H2O)2). The term "methyl" was derived in about 1840 by
back-formation In etymology, back-formation is the process or result of creating a new word via inflection, typically by removing or substituting actual or supposed affixes from a lexical item, in a way that expands the number of lexemes associated with the c ...
from "methylene", and was then applied to describe "methyl alcohol". This was shortened to "methanol" in 1892 by the International Conference on Chemical Nomenclature. The
suffix In linguistics, a suffix is an affix which is placed after the stem of a word. Common examples are case endings, which indicate the grammatical case of nouns, adjectives, and verb endings, which form the conjugation of verbs. Suffixes can carry ...
-yl, which, in organic chemistry, forms names of
carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon make ...
groups, is from the word ''methyl''. French chemist Paul Sabatier presented the first
process A process is a series or set of activities that interact to produce a result; it may occur once-only or be recurrent or periodic. Things called a process include: Business and management *Business process, activities that produce a specific se ...
that could be used to produce methanol synthetically in 1905. This process suggested that carbon dioxide and hydrogen could be reacted to produce methanol. German chemists Alwin Mittasch and Mathias Pier, working for Badische-Anilin & Soda-Fabrik (BASF), developed a means to convert synthesis gas (a mixture of
carbon monoxide Carbon monoxide ( chemical formula CO) is a colorless, poisonous, odorless, tasteless, flammable gas that is slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the simp ...
,
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 tran ...
, and
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, a ...
) into methanol and received a patent. According to Bozzano and Manenti, BASF's process was first utilized in Leuna, Germany in 1923. Operating conditions consisted of "high" temperatures (between 300 and 400 °C) and pressures (between 250 and 350 atm) with a
zinc Zinc is a chemical element with the symbol Zn and atomic number 30. Zinc is a slightly brittle metal at room temperature and has a shiny-greyish appearance when oxidation is removed. It is the first element in group 12 (IIB) of the periodic t ...
/
chromium oxide Chromium oxide may refer to: * Chromium(II) oxide, CrO * Chromium(III) oxide, Cr2O3 * Chromium dioxide (chromium(IV) oxide), CrO2, which includes the hypothetical compound chromium(II) chromate * Chromium trioxide (chromium(VI) oxide), CrO3 * Ch ...
catalyst. US patent 1,569,775 () was applied for on 4 Sep 1924 and issued on 12 January 1926 to BASF; the process used a chromium and
manganese oxide Manganese oxide is any of a variety of manganese oxides and hydroxides.Wells A.F. (1984) ''Structural inorganic chemistry'' 5th edition Oxford Science Publications, . These include * Manganese(II) oxide, MnO * Manganese(II,III) oxide, Mn3O4 * Mang ...
catalyst 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 recy ...
with extremely vigorous conditions: pressures ranging from 50 to 220 atm, and temperatures up to 450 °C. Modern methanol production has been made more efficient through use of catalysts (commonly copper) capable of operating at lower pressures. The modern low pressure methanol (LPM) process was developed by ICI in the late 1960s with the technology patent since long expired. During
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 World War II by country, vast majority of the world's countries—including all of the great power ...
, methanol was used as a fuel in several German military rocket designs, under the name M-Stoff, and in a roughly 50/50 mixture with hydrazine, known as
C-Stoff C-Stoff (; "substance C") was a reductant used in bipropellant rocket fuels (as a fuel itself) developed by Hellmuth Walter Kommanditgesellschaft in Germany during World War II. It was developed for use with T-Stoff (a high-test peroxide) as an oxi ...
. The use of methanol as a motor fuel received attention during the oil crises of the 1970s. By the mid-1990s, over 20,000 methanol " flexible fuel vehicles" (FFV) capable of operating on methanol or gasoline were introduced in the U.S. In addition, low levels of methanol were blended in gasoline fuels sold in Europe during much of the 1980s and early-1990s. Automakers stopped building methanol FFVs by the late-1990s, switching their attention to ethanol-fueled vehicles. While the methanol FFV program was a technical success, rising methanol pricing in the mid- to late-1990s during a period of slumping gasoline pump prices diminished interest in methanol fuels. In the early 1970s, a process was developed by
Mobil Mobil is a petroleum brand owned and operated by American oil and gas corporation ExxonMobil. The brand was formerly owned and operated by an oil and gas corporation of the same name, which itself merged with Exxon to form ExxonMobil in 1999. ...
for producing gasoline fuel from methanol. Between the 1960s and 1980s methanol emerged as a precursor to the feedstock chemicals acetic acid and
acetic anhydride Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a col ...
. These processes include the Monsanto acetic acid synthesis, Cativa process, and Tennessee Eastman acetic anhydride process.


See also

*
Aminomethanol Aminomethanol is the amino alcohol with the chemical formula of H2NCH2OH. With an amino group and an alcohol group on the same carbon atom, the compound is also an hemiaminal. In aqueous solution, methanolamine exists in equilibrium with formald ...
* Methanol (data page) * Trimethyl carbinol


References


Further reading

* Robert Boyle, '' The Sceptical Chymist'' (1661) – contains account of distillation of wood alcohol.


External links

*
Methyl Alcohol (Methanol)
CDC/NIOSH, links to safety information

* ttp://www.npi.gov.au/resource/methanol Methanol Fact Sheet– National Pollutant Inventory {{Authority control Alkanols Alcohol solvents Anatomical preservation Biofuels Energy storage Hazardous air pollutants Human metabolites Neurotoxins Oxygenates Commodity chemicals GABAA receptor positive allosteric modulators ur:میتھنال