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Ethanol
From Wikipedia, the free encyclopedia

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a powerful 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 an alcohol fuel. In common usage, it is often referred to simply as alcohol or spirits. Ethanol is a straight-chain alcohol, and its molecular formula is C2H5OH. Its empirical formula is C2H6O. An alternative notation is CH3CH2OH, 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 organic reactions 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 byproducts of petroleum refining.[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

Systematic name Ethanol[1] Other names Absolute alcohol Drinking alcohol Ethyl alcohol Ethyl hydrate Ethyl hydroxide Ethylic alcohol Ethylol Grain alcohol Hydroxyethane Methylcarbinol

Identifiers CAS number PubChem ChemSpider UNII EC number UN number DrugBank KEGG MeSH ChEBI ChEMBL RTECS number ATC code 64-17-5 702 682 3K9958V90M 200-578-6 1170 DB00898 D00068 Ethanol CHEBI:16236 CHEMBL545 KQ6300000 D01AE06 (http://www.whocc.no/atc_ddd_index/?

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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").

code=D01AE06) ,D08AX08, V03AB16, V03AZ01 Beilstein Reference 1718733 Gmelin Reference 3DMet 787 B01253
SMILES InChI

Contents
1 History 2 Physical properties 3 Production 3.1 Ethylene hydration 3.2 Fermentation 3.3 Cellulosic ethanol 3.4 Prospective technologies 3.5 Testing 3.6 Purification 3.7 Grades of ethanol 3.7.1 Denatured alcohol 3.7.2 Absolute ethanol 3.7.3 Rectified spirits 4 Reactions 4.1 Ester formation 4.2 Dehydration 4.3 Combustion 4.4 Acid-base chemistry 4.5 Halogenation 4.6 Oxidation 5 Uses 5.1 As a fuel 5.2 Alcoholic beverages 5.3 Feedstock 5.4 Antiseptic 5.5 Treatment for poisoning by other alcohols 5.6 Solvent 5.7 Historical uses 6 Pharmacology 7 Drug effects 7.1 Short-term 7.1.1 Effects on the central nervous system 7.1.2 Effects on metabolism 7.1.3 Drug interactions
Molecular formula Molar mass Exact mass Appearance Density Melting point

Properties C2H6O 46.07 g mol1 46.041864814 g mol1 Colorless liquid 0.789 g cm3 114 C, 159 K, -173 F

Boiling point

78 C, 351 K, 172 F -0.18 5.95 kPa (at 20 C) 15.9[2] -1.9

log P Vapor pressure Acidity (pKa) Basicity (pKb) Viscosity Dipole moment

Refractive index (nD) 1.36 0.0012 Pa s (at 20 C) 1.69 D Pharmacology Routes of administration Intramuscular Intravenous Oral Topical Hepatic Hazards MSDS EU Index EU classification R-phrases S-phrases R11 (S2), S7, S16 External MSDS 603-002-00-5
F

Metabolism

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7.1.4 Magnitude of effects 7.2 Long-term 7.2.1 Birth defects 7.2.2 Other effects 8 Natural occurrence 9 See also 10 References 11 Further reading 12 External links

NFPA 704

3 2 0

Flash point Autoignition temperature LD50 Structure and properties Thermodynamic data Spectral data

13-14 C 362 C 5628 mg kg-1 (oral, rat) Supplementary data page n, r, etc. Phase behaviour Solid, liquid, gas UV, IR, NMR, MS

History
For more details on this topic, see Distilled beverage. Ethanol has been used by humans since prehistory as the intoxicating ingredient of alcoholic beverages. Dried residue on 9,000year-old pottery found in China imply that Neolithic people consumed alcoholic beverages.[4]

(what is this?) (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 C, 100 kPa) Infobox references

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-Thodore de Saussure determined ethanols chemical formula.[6] Fifty years later, Archibald Scott Couper published ethanol's structural formula. 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. Srullas 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.

Physical properties

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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. Ethanols 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. 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]

Ethanols miscibility with water contrasts with that 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] Thermophysical properties of mixtures of ethanol with water and dodecane

Ethanol burning with its spectrum depicted

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Excess volume of the mixture of ethanol and water (volume contraction)

Heat of mixing of the mixture of ethanol Vapor-liquid equilibrium of and water ethanol and water (includi

Solid-liquid equilibrium of the mixture of Miscibility gap in the mixture of dodecane ethanol and water (including eutecticum) and ethanol 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.

Hydrogen bonding in solid ethanol at 186 C

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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 wines 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 =589.3 nm and 18.35 C).[12]

Production
Ethanol is produced both as a petrochemical, through the hydration of ethylene, and biologically, 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 often made from petrochemical feed stocks, primarily by the acid-catalyzed hydration of ethylene, represented by the chemical equation C2H4(g) + H2O(g) CH3CH2OH(l). The catalyst is most commonly phosphoric acid,[22] adsorbed onto a porous support such as silica gel or earth. This catalyst was first used for 94% denatured ethanol sold [23] large-scale ethanol production by the Shell Oil Company in 1947. The in a bottle for household use 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

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CH3CH2SO4H + H2O CH3CH2OH + H2SO4

Fermentation
Main article: Ethanol fermentation Ethanol for use in alcoholic beverages, and the vast majority of ethanol for use as fuel, 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 --> 4 CH3CH2OH + 4 CO2 The process of culturing yeast under conditions to produce alcohol is called fermentation. This process is carried out at around 3540 C. Ethanol's toxicity to yeast limits the ethanol concentration obtainable by brewing. 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
Main article: 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]

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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 U.S. 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 to 100 million gallons of ethanol a year (200400 ML/a).[33]

Prospective technologies
The anaerobic bacterium Clostridium ljungdahlii, discovered in commercial chicken wastes, can produce ethanol from singlecarbon 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. Another prospective technology is the closed-loop ethanol plant. South Dakota [35] 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%.[36] 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.[37]
Ethanol plant in Turner County,

Testing
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 cm1. 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,

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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.

Infrared reflection spectra of liquid ethanol, showing the -OH band centered at ~3300 cm1 and C-H bands at ~2950 cm1.

Purification
Main article: Ethanol purification Ethylene hydration or brewing produces an ethanolwater 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.[38] There is also an absolute alcohol production process by desiccation using glycerol. Alcohol produced by this method is known as spectroscopic alcoholso called because the absence of benzene makes it suitable as a solvent in spectroscopy.

Grades of ethanol
Denatured alcohol Main article: 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.[39][40] 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. It may contain trace amounts of toxic benzene if azeotropic distillation is used to remove water.[41] Absolute ethanol is used as a solvent for laboratory and industrial applications, where water

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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.
[42]

Pure ethanol is classed as 200 proof in the USA, equivalent to 175 degrees proof in the UK system.[43] 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.[44]

Reactions
For more details on this topic, see 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 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); (Hc = 1371 kJ/mol[45]) specific heat = 2.44 kJ/(kgK)

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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 SN2 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.[46] " 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.

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Uses
As a fuel
Main article: Ethanol fuel The largest single use of ethanol is as a motor fuel and fuel additive. Brazil has the largest national fuel ethanol industry. 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.[51] The U.S. uses Gasohol (max 10% ethanol) and E85 (85% ethanol) ethanol/gasoline mixtures. Ethanol may also be utilized as a rocket fuel, and is currently in lightweight rocket-powered racing aircraft.[52] Energy content of some fuels compared with ethanol:[47] Fuel type Dry wood (20% moisture) Methanol Ethanol E85 (85% ethanol, 15% gasoline) Liquefied natural gas Autogas (LPG) (60% propane + 40% butane) 17.9 MJ/L MJ/kg ~19.5 19.9 123 21.2[48] 26.8[48] 113[49] 25.2 25.3 26.8 33.2 ~55 50. 46.8 47.1
[50]

Research octane number

105

Aviation gasoline 33.5 (high-octane gasoline, not jet fuel) Gasohol (90% gasoline + 10% ethanol) Regular gasoline Premium gasoline Diesel 38.6 50 33.7 34.8

93/94

44.4 min. 91 max. 104 25

45.4 23

Ethanol as a fuel reduces harmful Charcoal, extruded tailpipe emissions of carbon monoxide, particulate matter, oxides of nitrogen, and other ozone-forming pollutants.[53] 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%.[54] 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.[55] This leads to a significantly larger photochemical reactivity that generates much more ground level ozone.[56] These data have been assembled into The Clean Fuels Report comparison of fuel emissions[57] and show that ethanol exhaust generates 2.14 times as much ozone as does gasoline exhaust.[citation needed] When this is added

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into the custom Localised Pollution Index (LPI) of The Clean Fuels USP grade ethanol for Report the local pollution (pollution that contributes to smog) is 1.7 on a laboratory use. 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).[58] 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.[59] More than 20% of Brazilian cars are able to use 100% ethanol as fuel, which includes ethanolonly engines and flex-fuel engines.[60] 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 Ethanol pump station in So Paulo, automobiles with large national infrastructure that produces Brazil where the fuel is available ethanol from domestically grown sugar cane. Sugar cane not commercially. 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] 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 GL) of ethanol per year. An additional 72 construction projects underway (in the U.S.) can add 6.4 billion gallons of new capacity in the next 18 months. Over time, it is believed that a material portion of the 150 billion gallon per year market for gasoline will begin to be replaced with fuel ethanol.[61] 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.[62] Mechanics also have seen increased cases of damage to small engines, in particular, the carburetor, attributable to ethanol's increased water retention in fuel.[63]
A Ford Taurus "fueled by clean burning ethanol" owned by New York City.

Alcoholic beverages
Main article: Alcoholic beverage

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

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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.[64] Similar psychoactives include those that also interact with GABA receptors, such as gamma-hydroxybutyric acid (GHB).[65] 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 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 freezedistilled, 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
Main article: Chemical derivatives of ethanol

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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.[66]

Treatment for poisoning by other alcohols


Ethanol is sometimes used to treat poisoning by other, more toxic alcohols, in particular methanol[67] and ethylene glycol. Ethanol competes with other alcohols for the alcohol dehydrogenase enzyme, lessening metabolism into toxic aldehyde and carboxylic acid derivatives,[68] and reducing one of the more serious toxic effects of the glycols, their tendency 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.[69][70] 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.[71] Alcohols fell into general disuse as more efficient rocket fuels were developed.[70]

Pharmacology
Ethanol binds to acetylcholine, GABA, serotonin, and NMDA receptors.[72] 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.

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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. In this way the oxidation of methanol to the toxic formaldehyde and formic acid in the (human body) can be prevented by giving an appropriate amount of ethanol to a person having ingested methanol. Note that methanol is very toxic and causes blindness and death. A person having ingested ethylene glycol can be treated in the same way.

Drug effects
Pure ethanol will irritate the skin and eyes.[73] Nausea, vomiting and intoxication are symptoms of ingestion. Long-term use by ingestion can result in serious liver damage.[74] Atmospheric concentrations above one in a thousand are above the European Union Occupational exposure limits.[74]

Short-term
Main article: Short-term effects of alcohol Effects on the central nervous system BAC (% v/v)

BAC (g/L)

Symptoms[75]

Ethanol is a central nervous system 0.5 0.05% Euphoria, talkativeness, relaxation depressant and has significant Central nervous system depression, nausea, psychoactive effects in sublethal 1 0.1 % possible vomiting, impaired motor and doses; for specifics, see effects of sensory function, impaired cognition alcohol on the body by dose. Based >1.4 >0.14% Decreased blood flow to brain on its abilities to change the human consciousness, ethanol is considered 3 0.3% Stupefaction, possible unconsciousness a psychoactive drug.[76] Death from 4 0.4% Possible death ethyl alcohol consumption is >5.5 >0.55% Death 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 0.30.4%.[77] 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).[78] Prolonged heavy consumption of alcohol can cause significant permanent damage to the brain and other organs. See Alcohol consumption and health.

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In America, about half of the deaths in car accidents occur in alcohol-related crashes.[79] The risk of a fatal car accident increases exponentially with the level of alcohol in the driver's blood.[80] 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 Main articles: Ethanol metabolism and Alcohol dehydrogenase Ethanol within the human body is converted into acetaldehyde by alcohol dehydrogenase and then into acetic acid by acetaldehyde dehydrogenase. The product of the first step of this breakdown, acetaldehyde,[81] 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,[65] 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.[77] 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.[82]

Long-term
Main article: Longterm effects of alcohol

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Birth defects Ethanol is classified as a teratogen. See fetal alcohol syndrome. Other effects

Most significant of the possible long-term effects of ethanol. In addition, in pregnant women, large consumption causes fetal alcohol syndrome.

Frequent drinking of alcoholic beverages has been shown to be a major contributing factor in cases of elevated blood levels of triglycerides.[83] Ethanol is not a carcinogen.[84][85] However, the first metabolic product of ethanol, acetaldehyde, is toxic, mutagenic, and carcinogenic.

Natural occurrence
Ethanol is produced naturally from the fermentation of overripe fruit by yeasts.[86] Despite many reports to the contrary, there is little scientific evidence that animals seek out overripe fruit for its intoxicating effects; rather, it suggests that they instead actively avoid doing so.[87] Ethanol is also produced during the germination of many plants as a result of natural anerobiosis.[88] Ethanol has been detected in outer space, forming an icy coating around dust grains in interstellar clouds.[89]

See also
2,2,2-Trichloroethanol Biodiesel Breathalyzer Butanol fuel Cellulosic ethanol commercialization Ethanol (data page) Isopropyl alcohol Outline of energy Propan-1-ol Rubbing alcohol Timeline of alcohol fuel

References
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67. ^ "Methanol Poisoning" (http://wwwclinpharm.medschl.cam.ac.uk/pages/teaching/topics/poison/poison9.html) . Cambridge University School of Clinical Medicine. http://www-clinpharm.medschl.cam.ac.uk/pages/teaching/topics/poison/poison9.html. Retrieved 2007-09-04. 68. ^ Barceloux DG, Bond GR, Krenzelok EP, Cooper H, Vale JA (2002). "American Academy of Clinical Toxicology practice guidelines on the treatment of methanol poisoning". J. Toxicol. Clin. Toxicol. 40 (4): 415. doi:10.1081/CLT-120006745 (http://dx.doi.org/10.1081%2FCLT-120006745) . PMID 12216995 (http://www.ncbi.nlm.nih.gov/pubmed/12216995) . 69. ^ David Darling. "The Internet Encyclopedia of Science: V-2" (http://daviddarling.info/encyclopedia/V/V2.html) . http://daviddarling.info/encyclopedia/V/V-2.html. 70. ^ a b Braeunig, Robert A. "Rocket Propellants." (http://braeunig.us/space/propel.htm) (Website). Rocket & Space Technology, 2006. Retrieved on 2007-08-23. 71. ^ "A Brief History of Rocketry." (http://science.ksc.nasa.gov/history/rocket-history.txt) NASA Historical Archive, via science.ksc.nasa.gov. 72. ^ "The Brain from Top to Bottom Alcohol (Intermediate, Molecular)" (http://thebrain.mcgill.ca/flash/i/i_03/i_03_m/i_03_m_par/i_03_m_par_alcool.html) . Canadian Institute of Neurosciences, Mental Health and Addiction. McGill University. http://thebrain.mcgill.ca/flash/i/i_03/i_03_m/i_03_m_par/i_03_m_par_alcool.html. Retrieved 2010-02-13. 73. ^ http://www.nfpa.org/Assets/files/AboutTheCodes/704/CLA-AAA_ROPminutes_01-10.pdf 74. ^ a b "Safety data for ethyl alcohol" (http://msds.chem.ox.ac.uk/ET/ethyl_alcohol.html) . Msds.chem.ox.ac.uk. 2008-05-09. http://msds.chem.ox.ac.uk/ET/ethyl_alcohol.html. Retrieved 2011-01-03. 75. ^ Pohorecky LA, Brick J (1988). "Pharmacology of ethanol". Pharmacol. Ther. 36 (23): 335. doi:10.1016/0163-7258(88)90109-X (http://dx.doi.org/10.1016%2F0163-7258%2888%2990109-X) . PMID 3279433 (http://www.ncbi.nlm.nih.gov/pubmed/3279433) . 76. ^ MedlinePlus Encyclopedia Alcohol Use (http://www.nlm.nih.gov/medlineplus/ency/article/001944.htm) 77. ^ a b David A. Yost, MD (2002). Acute care for alcohol intoxication (http://my.lecom.edu/library/internetresources/journal%20articles/Acute%20Care%20for%20Alcohol% 20Intoxication.pdf) . 112. Postgraduate Medicine Online. http://my.lecom.edu/library/internetresources/journal%20articles/Acute%20Care%20for%20Alcohol% 20Intoxication.pdf. Retrieved 2007-09-29. 78. ^ Santhakumar V, Wallner M, Otis TS (2007). "Ethanol acts directly on extrasynaptic subtypes of GABAA receptors to increase tonic inhibition" (http://www.pubmedcentral.nih.gov/articlerender.fcgi? tool=pmcentrez&artid=2040048) . Alcohol 41 (3): 21121. doi:10.1016/j.alcohol.2007.04.011 (http://dx.doi.org/10.1016%2Fj.alcohol.2007.04.011) . PMC 2040048 (http://www.pubmedcentral.gov/articlerender.fcgi?tool=pmcentrez&artid=2040048) . PMID 17591544 (http://www.ncbi.nlm.nih.gov/pubmed/17591544) . http://www.pubmedcentral.nih.gov/articlerender.fcgi? tool=pmcentrez&artid=2040048. 79. ^ Hingson R, Winter M (2003). "Epidemiology and consequences of drinking and driving". Alcohol research & health : the journal of the National Institute on Alcohol Abuse and Alcoholism 27 (1): 63. PMID 15301401 (http://www.ncbi.nlm.nih.gov/pubmed/15301401) . 80. ^ Naranjo CA, Bremner KE (1993). "Behavioural correlates of alcohol intoxication". Addiction 88 (1): 25. doi:10.1111/j.1360-0443.1993.tb02761.x (http://dx.doi.org/10.1111%2Fj.1360-0443.1993.tb02761.x) . PMID 8448514 (http://www.ncbi.nlm.nih.gov/pubmed/8448514) . 81. ^ Boggan, Bill. "Metabolism of Ethyl Alcohol in the Body" (http://chemcases.com/alcohol/alc-06.htm) . Chemases.com. http://chemcases.com/alcohol/alc-06.htm. Retrieved 2007-09-29. 82. ^ Agarwal DP, Goedde HW (1992). "Pharmacogenetics of alcohol metabolism and alcoholism". Pharmacogenetics 2 (2): 48. doi:10.1097/00008571-199204000-00002 (http://dx.doi.org/10.1097% 2F00008571-199204000-00002) . PMID 1302043 (http://www.ncbi.nlm.nih.gov/pubmed/1302043) . 83. ^ "Triglycerides" (http://americanheart.org/presenter.jhtml?identifier=4778) . American Heart Association. http://americanheart.org/presenter.jhtml?identifier=4778. Retrieved 2007-09-04. 84. ^ "Material Data Safety Sheet" (http://www.cise.columbia.edu/clean/msds/ethanol.pdf) (PDF). Burdick and Jackson. http://www.cise.columbia.edu/clean/msds/ethanol.pdf. Retrieved 2007-10-25. 85. ^ Chavez, Pollyanna R.; Wang, Xiang-Dong; Meyer, Jean. "Animal Models for Carcinogenesis and Chemoprevention, abstract #C42: Effects of Chronic Ethanol Intake on Cyclin D1 Levels and Altered Foci in Diethylnitrosamine-initiated Rats" (http://www.aacr.org/PDF_files/2004Prevention/Program/2004_Prevention_Abstracts.pdf) (PDF).

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Further reading
The National Institute on Alcohol Abuse and Alcoholism maintains a database of alcohol-related health effects. ETOH Archival Database (19722003) (http://etoh.niaaa.nih.gov/Archive.htm) Alcohol and Alcohol Problems Science Database. "Alcohol." (1911). In Hugh Chisholm (Ed.) Encyclopdia Britannica Eleventh Edition. Online reprint (http://91.1911encyclopedia.org/A/AL/ALCOHOL.htm) Boyce, John M., and Pittet Didier. (2003). Hand Hygiene in Healthcare Settings. (http://cdc.gov/handhygiene/) Centers for Disease Control, Atlanta, Georgia, United States. Rene Martinez VitalSensors Technologies LLC. "VS1000A Series In-Line Ethanol Sensors for the Beverage and BioFuel Industry" (http://vitalsensorstech.com/VitalSensors%20VS-1000A% 20Ethanol%20Alcohol%20Sensor%20Data%20Sheet.pdf) (PDF). http://vitalsensorstech.com/VitalSensors%20VS-1000A%20Ethanol%20Alcohol%20Sensor% 20Data%20Sheet.pdf. Martinez describes the theory and practice of measuring brix on-line in beverages. Sci-toys website explanation of US denatured alcohol designations (http://scitoys.com/ingredients/alcohol.html) Smith, M.G., and M. Snyder. (2005). "Ethanol-induced virulence of Acinetobacter baumannii". American Society for Microbiology meeting. June 5 June 9. Atlanta.

External links
International Labour Organization (http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc00/icsc0044.htm) ethanol safety information National Pollutant Inventory Ethanol Fact Sheet (http://www.npi.gov.au/substances/ethanol/index.html) National Institute of Standards and Technology (http://webbook.nist.gov/cgi/cbook.cgi? Name=ethanol&Units=SI) chemical data on ethanol

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ChEBI biology related (http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16236) Chicago Board of Trade (http://cbot.com/) news and market data on ethanol futures Calculation of vapor pressure (http://ddbonline.ddbst.de/AntoineCalculation/AntoineCalculationCGI.exe?component=Ethanol) , liquid density (http://ddbonline.ddbst.de/DIPPR105DensityCalculation/DIPPR105CalculationCGI.exe? component=Ethanol) , dynamic liquid viscosity (http://ddbonline.ddbst.de/VogelCalculation/VogelCalculationCGI.exe?component=Ethanol) , surface tension (http://ddbonline.ddbst.de/DIPPR106SFTCalculation/DIPPR106SFTCalculationCGI.exe? component=Ethanol) of ethanol U.S. National Library of Medicine: Drug Information Portal Ethanol (http://druginfo.nlm.nih.gov/drugportal/dpdirect.jsp?name=Ethanol) Ethanol History (http://www.ethanolhistory.com/) A look into the history of ethanol Retrieved from "http://en.wikipedia.org/wiki/Ethanol" Categories: Alcohol | Alcohols | Alcohol solvents | Anatomical preservation | Anxiolytics | Disinfectants | Drugs | Ethanol | Household chemicals | NMDA receptor antagonists | Oxygenates | Rocket fuels | Teratogens This page was last modified on 6 April 2011 at 05:26. Text is available under the Creative Commons Attribution-ShareAlike License; additional terms may apply. See Terms of Use for details. Wikipedia is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization.

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