ethanol

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Ethanol
Systematic name Ethanol[1]
Other names Absolute alcohol Alcohol Drinking alcohol Ethyl alcohol Ethyl hydrate Ethyl hydroxide Ethylic alcohol Ethylol Grain alcohol Hydroxyethane Methylcarbinol
Identifiers
CAS number	64-17-5 Y
PubChem	702
ChemSpider	682 Y
UNII	3K9958V90M Y
EC number	200-578-6
UN number	1170
DrugBank	DB00898
KEGG	D00068 Y
MeSH	Ethanol
ChEBI	CHEBI:16236 Y
ChEMBL	CHEMBL545 Y
RTECS number	KQ6300000
ATC code	D01AE06,D08AX08, V03AB16, V03AZ01
Beilstein Reference	1718733
Gmelin Reference	787
3DMet	B01253
Jmol-3D images	Image 1
SMILES CCO
InChI InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3 Y Key: LFQSCWFLJHTTHZ-UHFFFAOYSA-N Y InChI=1/C2H6O/c1-2-3/h3H,2H2,1H3 Key: LFQSCWFLJHTTHZ-UHFFFAOYAB
Properties
Molecular formula	C2H6O
Molar mass	46.07 g mol−1
Exact mass	46.041864814 g mol−1
Appearance	Colorless liquid
Density	0.789 g/cm3
Melting point	−114 °C, 159 K, -173 °F
Boiling point	78 °C, 351 K, 172 °F
log P	-0.18
Vapor pressure	5.95 kPa (at 20 °C)
Acidity (pKa)	15.9[2]
Basicity (pKb)	-1.9
Refractive index (nD)	1.36
Viscosity	0.0012 Pa s (at 20 °C)
Dipole moment	1.69 D
Pharmacology
Routes of administration	Intramuscular Intravenous Oral Topical
Metabolism	Hepatic
Hazards
MSDS	External MSDS
EU Index	603-002-00-5
EU classification	F
R-phrases	R11
S-phrases	(S2), S7, S16
NFPA 704	3 2 0
Flash point	13–14 °C
Autoignition temperature	362 °C
LD50	5628 mg kg−1 (oral, rat)
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a solvent, and as a fuel. In common usage, it is often referred to simply as alcohol or spirits.

Ethanol is a 2-carbon alcohol with the molecular formula CH₃CH₂OH. Its empirical formula is C₂H₆O. 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 ether. Ethanol is often abbreviated as EtOH, using the common organic chemistry notation of representing the ethyl group (C₂H₅) with Et.

The fermentation of sugar into ethanol is one of the earliest biotechnologies employed by humanity. The intoxicating effects of ethanol consumption have been known since ancient times. In modern times, ethanol intended for industrial use is also produced from ethylene.^[3] 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 an essential 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.

Ethanol is the systematic name defined by the IUPAC nomenclature of organic chemistry for a molecule with two carbon atoms (prefix "eth-"), having a single bond between them (suffix "-ane"), and an attached -OH group (suffix "-ol").^[1] Ethyl redirects here; such usage almost always refers to a part of this sub-grouping inside a larger molecule.

History

Ethanol has been used by humans since prehistory as the intoxicating ingredient of alcoholic beverages. Dried residue on 9,000-year-old pottery found in China imply that Neolithic people consumed alcoholic beverages.^[4]

Although distillation was well known by the early Greeks and Arabs, the first recorded production of alcohol from distilled wine was by the School of Salerno alchemists in the 12th century.^[5] The first to mention absolute alcohol, in contrast with alcohol-water mixtures, was Raymond Lull.^[5]

In 1796, Johann Tobias Lowitz obtained pure ethanol by filtering distilled ethanol through activated charcoal. Antoine Lavoisier described ethanol as a compound of carbon, hydrogen, and oxygen, and in 1808 Nicolas-Théodore de Saussure determined ethanol’s chemical formula.^[6] Fifty years later, Archibald Scott Couper published the structural formula of ethanol. It is one of the first structural formulas determined.^[7]

Ethanol was first prepared synthetically in 1826 through the independent efforts of Henry Hennel in Great Britain and S.G. Sérullas in France. In 1828, Michael Faraday prepared ethanol by acid-catalyzed hydration of ethylene, a process similar to current industrial ethanol synthesis.^[8]

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.^[9] Original Ford Model T automobiles ran on ethanol until 1908.^[10] With the advent of Prohibition in 1920, ethanol fuel sellers were accused of being allied with moonshiners,^[9] and ethanol fuel fell into disuse until late in the 20th century.^{[dubious – discuss]}

Physical properties

Ethanol burning with its spectrum depicted

Ethanol is a volatile, colorless liquid that has a slight odor.^[11] 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.

Solvent properties

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.^[12][13] It is also miscible with light aliphatic hydrocarbons, such as pentane and hexane, and with aliphatic chlorides such as trichloroethane and tetrachloroethylene.^[13]

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.^[14] 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^[15]). 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.^[12][16] Mixing ethanol and water is exothermic. At 298 K, up to 777 J/mol^[17] are set free.

Mixtures of ethanol and water form an azeotrope at about 89 mole-% ethanol and 11 mole-% water^[18] or a mixture of about 96 volume percent ethanol and 4% water at normal pressure and T = 351 K. This azeotropic composition is strongly temperature- and pressure-dependent and vanishes at temperatures below 303 K.^[19]

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.^[13] Sodium and potassium chlorides are slightly soluble in ethanol.^[13] Because the ethanol molecule also has a nonpolar end, it will also dissolve nonpolar substances, including most essential oils^[20] 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.

Mixtures of ethanol and water that contain more than about 50% ethanol are flammable and easily ignited. Alcoholic proof is a widely used measure of how much ethanol (i.e., alcohol) such a mixture contains. In the 18th century, proof was determined by adding a liquor (such as rum) to gunpowder. If the gunpowder still burned, that was considered to be “100 degrees proof” that it was “good” liquor — hence it was called “100 degrees proof”.

Ethanol-water solutions that contain less than 50% ethanol may also be flammable if the solution is first heated. Some cooking methods call for wine to be added to a hot pan, causing it to flash boil into a vapor, which is then ignited to burn off excess alcohol.

Ethanol is slightly more refractive than water, having a refractive index of 1.36242 (at λ=589.3 nm and 18.35 °C).^[12]

Production

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.^[21] Which process is more economical depends on prevailing prices of petroleum and grain feed stocks.

Ethylene hydration

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, represented by the chemical equation

C₂H₄ + H₂O → CH₃CH₂OH

The catalyst is most commonly phosphoric acid,^[22] 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.^[23] The reaction is carried out with an excess of high pressure steam at 300 °C. 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,^[24] but now almost entirely obsolete, ethylene was hydrated indirectly by reacting it with concentrated sulfuric acid to produce ethyl sulfate, which was hydrolysed to yield ethanol and regenerate the sulfuric acid:^[25]

C₂H₄ + H₂SO₄ → CH₃CH₂SO₄H

CH₃CH₂SO₄H + H₂O → CH₃CH₂OH + H₂SO₄

Fermentation

Ethanol for use in alcoholic beverages, and the vast majority of ethanol for use as fuel,^{[citation needed]} is produced by fermentation. When certain species of yeast (e.g., Saccharomyces cerevisiae) metabolize sugar they produce ethanol and carbon dioxide. The chemical equations below summarize the conversion:

C₆H₁₂O₆ → 2 CH₃CH₂OH + 2 CO₂

C₁₂H₂₂O₁₁ + H₂O → 4 CH₃CH₂OH + 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. Toxicity of ethanol to yeast limits the ethanol concentration obtainable by brewing; higher concentrations, therefore, are usually obtained by fortification or distillation. The most ethanol-tolerant strains of yeast can survive up to approximately 15% ethanol by volume.^[26]

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. For fuel ethanol, the hydrolysis of starch into glucose can be accomplished more rapidly by treatment with dilute sulfuric acid, fungally produced amylase, or some combination of the two.^[27]

Cellulosic ethanol

Sugars for ethanol fermentation can be obtained from cellulose.^[28][29] Until recently, however, the cost of the cellulase enzymes capable of hydrolyzing cellulose has been prohibitive. The Canadian firm Iogen brought the first cellulose-based ethanol plant on-stream in 2004.^[30] Its primary consumer so far has been the Canadian government, which, along with the United States Department of Energy, has invested heavily in the commercialization of cellulosic ethanol. 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 enzyme companies are developing genetically engineered fungi that produce large volumes of cellulase, xylanase, and hemicellulase enzymes. These would convert agricultural residues such as corn stover, wheat straw, and sugar cane bagasse and energy crops such as switchgrass into fermentable sugars.^[31]

Cellulose-bearing materials typically also contain other polysaccharides, including hemicellulose. When undergoing hydrolysis, hemicellulose decomposes into mostly five-carbon sugars such as xylose. S. cerevisiae, the yeast most commonly used for ethanol production, cannot metabolize xylose. Other yeasts and bacteria are under investigation to ferment xylose and other pentoses into ethanol.^[32]

On January 14, 2008, General Motors announced a partnership with Coskata, Inc. The goal is to produce cellulosic ethanol cheaply, with an eventual goal of US$1 per US gallon ($0.30/L) for the fuel. The partnership plans to begin producing the fuel in large quantity by the end of 2008. In June 2009, this goal is still ahead of the firm. By 2011 a full-scale plant will come on line, capable of producing 50 million US gallons (190,000 m³) to 100 million US gallons (380,000 m³) of ethanol a year (200–400 ML/a).^[33]

Prospective technologies

Ethanol plant in Turner County, South Dakota

The anaerobic bacterium Clostridium ljungdahlii, discovered in commercial chicken wastes, can produce ethanol from single-carbon sources including synthesis gas, a mixture of carbon monoxide and hydrogen that can be generated from the partial combustion of either fossil fuels or biomass. Use of these bacteria to produce ethanol from synthesis gas has progressed to the pilot plant stage at the BRI Energy facility in Fayetteville, Arkansas.^[34] The BRI technology has been purchased by INEOS.

The bacterium E.coli when genetically engineered with cow rumen genes and enzymes can produce ethanol from corn stower.^[35]

Another prospective technology is the closed-loop ethanol plant.^[36] Ethanol produced from corn has a number of critics who suggest that it is primarily just recycled fossil fuels because of the energy required to grow the grain and convert it into ethanol. There is also the issue of competition with use of corn for food production. However, the closed-loop ethanol plant attempts to address this criticism. In a closed-loop plant, renewable energy for distillation comes from fermented manure, produced from cattle that have been fed the DDSG by-products from grain ethanol production. The concentrated compost nutrients from manure are then used to fertilize the soil and grow the next crop of grain to start the cycle again. Such a process is expected to lower the fossil fuel consumption used during conversion to ethanol by 75%.^[37]

An alternative technology allows for the production of biodiesel from distillers grain as an additional value product.^[38] Though in an early stage of research, there is some development of alternative production methods that use feed stocks such as municipal waste or recycled products, rice hulls, sugarcane bagasse, small diameter trees, wood chips, and switchgrass.^[39]

Testing

Infrared reflection spectra of liquid ethanol, showing the -OH band centered at ~3300 cm⁻¹ and C-H bands at ~2950 cm⁻¹.

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 industry.

Purification

Ethylene hydration or brewing produces an ethanol–water mixture. For most industrial and fuel uses, the ethanol must be purified. Fractional distillation can concentrate ethanol to 95.6% by volume (89.5 mole%). This mixture is an azeotrope with a boiling point of 78.1 °C, and cannot be further purified by distillation.

Common methods for obtaining absolute ethanol include desiccation using adsorbents such as starch, corn grits, or zeolites, which adsorb water preferentially, as well as azeotropic distillation and extractive distillation. Most ethanol fuel refineries use an adsorbent or zeolite to desiccate the ethanol stream.

In another method to obtain absolute alcohol, a small quantity of benzene is added to rectified spirit and the mixture is then distilled. Absolute alcohol is obtained in the third fraction, which distills over at 78.3 °C (351.4 K).^[14] Because a small amount of the benzene used remains in the solution, absolute alcohol produced by this method is not suitable for consumption, as benzene is carcinogenic.^[40]

There is also an absolute alcohol production process by desiccation using glycerol. Alcohol produced by this method is known as spectroscopic alcohol—so called because the absence of benzene makes it suitable as a solvent in spectroscopy.

Grades of ethanol

Denatured alcohol

Pure ethanol and alcoholic beverages are heavily taxed, but ethanol has many uses that do not involve consumption by humans. 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.^[41][42]

Absolute ethanol

Absolute or anhydrous alcohol refers to ethanol with a low water content. There are various grades with maximum water contents ranging from 1% to ppm levels. Absolute alcohol is not intended for human consumption. If azeotropic distillation is used to remove water, it will contain trace amounts of the material separation agent (e.g. benzene).^[43] 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 spectroscopy.^[44]

Pure ethanol is classed as 200 proof in the USA, equivalent to 175 degrees proof in the UK system.^[45]

Rectified spirits

Rectified spirit, an azeotropic composition containing 4% water, is used instead of anhydrous ethanol for various purposes. Wine spirits are about 188 proof. The impurities are different from those in 190 proof laboratory ethanol.^[46]

Reactions

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 group.

Ester formation

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 pentoxide respectively. 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 a widely used diuretic.

Dehydration

Strong acid desiccants cause the dehydration of ethanol to form diethyl ether and other byproducts. If the dehydration temperature exceeds around 160 °C, ethylene will be the main product. Millions of kilograms of diethyl ether are produced annually using sulfuric acid catalyst:

2 CH₃CH₂OH → CH₃CH₂OCH₂CH₃ + H₂O (on 120 °C)

Combustion

Complete combustion of ethanol forms carbon dioxide and water vapor:

C₂H₅OH (l) + 3 O₂ (g) → 2 CO₂ (g) + 3 H₂O (g); (ΔH_c = −1371 kJ/mol^[47]) 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, the ethoxide ion (CH₃CH₂O⁻), by reaction with an alkali metal such as sodium:^[14]

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 equilbrium 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 halides to produce ethyl halides such as ethyl chloride and ethyl bromide via an S_N2 reaction:

CH₃CH₂OH + HCl → CH₃CH₂Cl + H₂O

These reactions require a catalyst such as zinc chloride.^[25] HBr requires refluxing with a sulfuric acid catalyst.^[25] Ethyl halides can, in principle, also be produced by treating ethanol with more specialized halogenating agents, such as thionyl chloride or phosphorus tribromide.^[14][25]

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.^[48] " An intermediate in the reaction with chlorine is the aldehyde called chloral:

4 Cl₂ + CH₃CH₂OH → CCl₃CHO + 5 HCl

Oxidation

Ethanol can be oxidized to acetaldehyde and further oxidized to acetic acid, depending on the reagents and conditions.^[25] 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.

Uses

As a fuel

The largest single use of ethanol is as a motor fuel and fuel additive. More than any other major country, Brazil relies on ethanol as a motor fuel. 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 cars sold in the country. Brazilian ethanol is produced from sugar cane and noted for high carbon sequestration.^[53] The US uses Gasohol (max 10% ethanol) and E85 (85% ethanol) ethanol/gasoline mixtures.

USP grade ethanol for laboratory use.

Ethanol may also be utilized as a rocket fuel, and is currently in lightweight rocket-powered racing aircraft.^[54]

Australian law limits of the use of pure Ethanol sourced from Sugarcane waste to up to 10% in automobiles. It has been recommended that older cars (and vintage cars designed to use a slower burning fuel) have their valves upgraded or replaced.^[55]

Ethanol as a fuel reduces harmful tailpipe emissions of carbon monoxide, particulate matter, oxides of nitrogen, and other ozone-forming pollutants.^[56] Argonne National Laboratory analyzed the greenhouse gas emissions of many different engine and fuel combinations. Comparing ethanol blends with gasoline alone, they showed reductions of 8% with the biodiesel/petrodiesel blend known as B20, 17% with the conventional E85 ethanol blend, and that using cellulosic ethanol lowers emissions 64%.^[57]

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.^[58] This leads to a significantly larger photochemical reactivity that generates much more ground level ozone.^[59] These data have been assembled into The Clean Fuels Report comparison of fuel emissions^[60] and show that ethanol exhaust generates 2.14 times as much ozone as does gasoline exhaust.^{[citation needed]} When this is added into the custom Localised Pollution Index (LPI) of The Clean Fuels Report the local pollution (pollution that contributes to smog) is 1.7 on a scale where gasoline is 1.0 and higher numbers signify greater pollution. The 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).^[61]

Ethanol pump station in São Paulo, Brazil where the fuel is available commercially.

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.^[62] More than 20% of Brazilian cars are able to use 100% ethanol as fuel, which includes ethanol-only engines and flex-fuel engines.^[63] 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. 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 as a surprisingly efficient fuel to produce electricity.^{[citation needed]}

A Ford Taurus "fueled by clean burning ethanol" owned by New York City.

The United States fuel ethanol industry is based largely on corn. According to the Renewable Fuels Association, as of October 30, 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.^[64]

United States Postal Service vehicle running on E85, a "flex-fuel" blend in Saint Paul, Minnesota.

One problem with ethanol is its high miscibility with water, which means that it cannot be efficiently shipped through modern pipelines, like liquid hydrocarbons, over long distances.^[65] Mechanics also have seen increased cases of damage to small engines, in particular, the carburetor, attributable to the increased water retention by ethanol in fuel.^[66]

Alcoholic beverages

Ethanol is the principal psychoactive constituent in alcoholic beverages, with depressant effects on the central nervous system. It has a complex mode of action and affects multiple systems in the brain, the most notable one being its agonistic action on the GABA receptors.^[67] Similar psychoactives include those that also interact with GABA receptors, such as gamma-hydroxybutyric acid (GHB).^[68] Ethanol is metabolized by the body as an energy-providing nutrient, as it metabolizes into acetyl CoA, an intermediate common with glucose and fatty acid metabolism that can be used for energy in the citric acid cycle or for biosynthesis.

Alcoholic beverages vary considerably in ethanol content and in foodstuffs they are produced from. Most alcoholic beverages can be broadly classified as fermented beverages, beverages made by the action of yeast on sugary foodstuffs, or distilled beverages, beverages whose preparation involves concentrating the ethanol in fermented beverages by distillation. The ethanol content of a beverage is usually measured in terms of the volume fraction of ethanol in the beverage, expressed either as a percentage or in alcoholic proof units.

Fermented beverages can be broadly classified by the foodstuff they are fermented from. Beers are made from cereal grains or other starchy materials, wines and ciders from fruit juices, and meads from honey. Cultures around the world have made fermented beverages from numerous other foodstuffs, and local and national names for various fermented beverages abound.

Distilled beverages are made by distilling fermented beverages. Broad categories of distilled beverages include whiskeys, distilled from fermented cereal grains; brandies, distilled from fermented fruit juices; and rum, distilled from fermented molasses or sugarcane juice. Vodka and similar neutral grain spirits can be distilled from any fermented material (grain, tomatoes or potatoes are most common); these spirits are so thoroughly distilled that no tastes from the particular starting material remain. Numerous other spirits and liqueurs are prepared by infusing flavors from fruits, herbs, and spices into distilled spirits. A traditional example is gin, which is created by infusing juniper berries into a neutral grain alcohol.

In a few beverages, ethanol is concentrated by means other than distillation. Applejack is traditionally made by freeze distillation, by which water is frozen out of fermented apple cider, leaving a more ethanol-rich liquid behind. Ice beer (also known by the German term Eisbier or Eisbock) is also freeze-distilled, with beer as the base beverage. Fortified wines are prepared by adding brandy or some other distilled spirit to partially fermented wine. This kills the yeast and conserves some of the sugar in grape juice; such beverages not only are more ethanol-rich but are often sweeter than other wines.

Alcoholic beverages are sometimes used in cooking, not only for their inherent flavors but also because the alcohol dissolves hydrophobic flavor compounds, which water cannot.

Just as industrial ethanol is used as feedstock for the production of industrial acetic acid, alcoholic beverages are made into culinary/household vinegar: Wine and cider vinegar are both named for their respective source alcohols, whereas malt vinegar is derived from beer.

Feedstock

Ethanol is an important industrial ingredient and has widespread use as a base chemical for other organic compounds. These include ethyl halides, ethyl esters, diethyl ether, acetic acid, ethyl amines, and to a lesser extent butadiene.

Antiseptic

Ethanol is used in medical wipes and in most common antibacterial hand sanitizer gels at a concentration of about 62% v/v 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, but is ineffective against bacterial spores.^[69]

Treatment for poisoning by other alcohols

Ethanol is sometimes used to treat poisoning by other, more toxic alcohols, in particular methanol^[70] and ethylene glycol. Ethanol competes with other alcohols for the alcohol dehydrogenase enzyme, lessening metabolism into toxic aldehyde and carboxylic acid derivatives,^[71] and reducing one of the more serious toxic effect of the glycols to crystallize in the kidneys.

Solvent

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 perfumes and deodorants. It may also be used as a solvent in cooking, such as in vodka sauce.

Historical uses

Before the development of modern medicines, ethanol was used for a variety of medical purposes. It has been known to be used as a truth drug (as hinted at by the maxim "in vino veritas"), as medicine for depression and as an anesthetic.^{[citation needed]}

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.^[72][73] 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.^[74] Alcohols fell into general disuse as more efficient rocket fuels were developed.^[73]

Pharmacology

Ethanol binds to acetylcholine, GABA, serotonin, and NMDA receptors.^[75]

The removal of ethanol through oxidation by alcohol dehydrogenase in the liver from the human body is limited. Hence, the removal of a large concentration of alcohol from blood may follow zero-order kinetics. This means that alcohol leaves the body at a constant rate, rather than having an elimination half-life.

Also, the rate-limiting steps for one substance may be in common with other substances. For instance, the blood alcohol concentration can be used to modify the biochemistry of methanol and ethylene glycol. Methanol itself is not highly toxic, but its metabolites formaldehyde and formic acid are; therefore, to reduce the concentration of these harmful metabolites, ethanol can be ingested to reduce the rate of methanol metabolism due to shared rate-limiting steps. Ethylene glycol poisoning can be treated in the same way.

Drug effects

Pure ethanol will irritate the skin and eyes.^[76] Nausea, vomiting and intoxication are symptoms of ingestion. Long-term use by ingestion can result in serious liver damage.^[77] Atmospheric concentrations above one in a thousand are above the European Union Occupational exposure limits.^[77]

Short-term

Effects on the central nervous system

Ethanol is a central nervous system depressant and has significant psychoactive effects in sublethal doses; for specifics, see "Effects of alcohol on the body by dose". Based on its abilities to change the human consciousness, ethanol is considered a psychoactive drug.^[79] Death from ethyl alcohol consumption is possible when blood alcohol level reaches 0.4%. A blood level of 0.5% or more is commonly fatal. Levels of even less than 0.1% can cause intoxication, with unconsciousness often occurring at 0.3–0.4%.^[80]

The amount of ethanol in the body is typically quantified by blood alcohol content (BAC), which is here taken as weight of ethanol per unit volume of blood. The table at right summarizes the symptoms of ethanol consumption. Small doses of ethanol, in general, produce euphoria and relaxation; people experiencing these symptoms tend to become talkative and less inhibited, and may exhibit poor judgment. At higher dosages (BAC > 1 g/L), ethanol acts as a central nervous system depressant, producing at progressively higher dosages, impaired sensory and motor function, slowed cognition, stupefaction, unconsciousness, and possible death.

Ethanol acts in the central nervous system by binding to the GABA-A receptor, increasing the effects of the inhibitory neurotransmitter GABA (i.e., it is a positive allosteric modulator).^[81]

Prolonged heavy consumption of alcohol can cause significant permanent damage to the brain and other organs. See Alcohol consumption and health.

In USA, about half of the deaths in car accidents occur in alcohol-related crashes.^[82] The risk of a fatal car accident increases exponentially with the level of alcohol in the driver's blood.^[83] Most drunk driving laws governing the acceptable levels in the blood while driving or operating heavy machinery set typical upper limits of blood alcohol content (BAC) between 0.05% and 0.08%.^{[citation needed]}

Discontinuing consumption of alcohol after several years of heavy drinking can also be fatal. Alcohol withdrawal can cause anxiety, autonomic dysfunction, seizures, and hallucinations. Delirium tremens is a condition that requires people with a long history of heavy drinking to undertake an alcohol detoxification regimen.

Effects on metabolism

Ethanol within the human body is converted into acetaldehyde by alcohol dehydrogenase and then into the acetyl in acetyl CoA by acetaldehyde dehydrogenase. Acetyl CoA is the final product of both carbohydrate and fat metabolism, where the acetyl can be further used to produce energy or for biosynthesis. As such, ethanol is a nutrient. However, the product of the first step of this breakdown, acetaldehyde,^[84] is more toxic than ethanol. Acetaldehyde is linked to most of the clinical effects of alcohol. It has been shown to increase the risk of developing cirrhosis of the liver,^[68] multiple forms of cancer, and alcoholism.

Drug interactions

Ethanol can intensify the sedation caused by other central nervous system depressant drugs such as barbiturates, benzodiazepines, opioids, phenothiazines, and anti-depressants.^[80]

Magnitude of effects

Some individuals have less effective forms of one or both of the metabolizing enzymes, and can experience more severe symptoms from ethanol consumption than others. However, those having acquired alcohol tolerance have a greater quantity of these enzymes, and metabolize ethanol more rapidly.^[85]

Long-term

Birth defects

Ethanol is classified as a teratogen. See fetal alcohol syndrome.

Other effects

Frequent drinking of alcoholic beverages has been shown to be a major contributing factor in cases of elevated blood levels of triglycerides.^[86]

Ethanol is not a carcinogen.^[87][88] However, the first metabolic product of ethanol, acetaldehyde, is toxic, mutagenic, and carcinogenic.

Natural occurrence

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.^[89] Ethanol produced by symbiotic yeast can be found in Bertam Palm blossoms. Although some species such as the Pentailed Treeshrew exhibit ethanol seeking behaviors, most show no interest or avoidance of food sources containing ethanol.^[90] Ethanol is also produced during the germination of many plants as a result of natural anerobiosis.^[91] Ethanol has been detected in outer space, forming an icy coating around dust grains in interstellar clouds.^[92]

See also

Pharmacy and Pharmacology portal

References

Further reading

• The National Institute on Alcohol Abuse and Alcoholism maintains a database of alcohol-related health effects. ETOH Archival Database (1972–2003) Alcohol and Alcohol Problems Science Database.
• Boyce, John M., and Pittet Didier. (2003). “Hand Hygiene in Healthcare Settings.” Centers for Disease Control, Atlanta, Georgia, United States.
• Sci-toys website explanation of US denatured alcohol designations
• Smith, M.G., and M. Snyder. (2005). "Ethanol-induced virulence of Acinetobacter baumannii". American Society for Microbiology meeting. June 5 – June 9. Atlanta.

Appendix

Thermophysical properties of mixtures of ethanol with water and dodecane

Excess volume of the mixture of ethanol and water (volume contraction)	Heat of mixing of the mixture of ethanol and water	Vapor-liquid equilibrium of the mixture of ethanol and water (including azeotrope)
Solid-liquid equilibrium of the mixture of ethanol and water (including eutecticum)	Miscibility gap in the mixture of dodecane and ethanol

External links

Wikimedia Commons has media related to: Ethanol

• International Labour Organization ethanol safety information
• National Pollutant Inventory – Ethanol Fact Sheet
• National Institute of Standards and Technology chemical data on ethanol
• ChEBI – biology related
• Chicago Board of Trade news and market data on ethanol futures
• Calculation of vapor pressure, liquid density, dynamic liquid viscosity, surface tension of ethanol
• U.S. National Library of Medicine: Drug Information Portal – Ethanol
• Ethanol History A look into the history of ethanol

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