ethanol - wikipedia, the free encyclopedia

Ethanol

Ethanol[1]

Absolute alcoholAlcohol

Drinking alcoholEthyl alcoholEthyl hydrate

Ethyl hydroxideEthylic alcohol

EthylolGrain alcoholHydroxyethaneMethylcarbinol

Identifiers

CAS number 64-17-5

PubChem 702

ChemSpider 682

UNII 3K9958V90M

EC number 200-578-6

UN number 1170

DrugBank DB00898

KEGG D00068

MeSH Ethanol

ChEBI CHEBI:16236

ChEMBL CHEMBL545

RTECS number KQ6300000

ATC code D01AE06(http://www.whocc.no/atc_ddd_index/?code=D01AE06),D08AX08, V03AB16,V03AZ01

Beilstein Reference 1718733

Gmelin Reference 787

EthanolFrom Wikipedia, the free encyclopedia

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinkingalcohol, is a volatile, flammable, colorless liquid. A psychoactive drug and one ofthe oldest recreational drugs known, ethanol produces a state known as alcoholintoxication when consumed. Best known as the type of alcohol found in alcoholicbeverages, it is also used in thermometers, as a solvent, and as a fuel. In commonusage, it is often referred to simply as alcohol or spirits.

Contents

1 Chemical formula2 Name3 History4 Physical properties

4.1 Solvent properties4.2 Flammability

5 Production5.1 Ethylene hydration5.2 Fermentation

5.2.1 Cellulosic ethanol5.2.2 Hydrocarbon-based ethanol production

5.3 Prospective technologies5.4 Testing5.5 Purification5.6 Grades of ethanol

5.6.1 Denatured alcohol5.6.2 Absolute alcohol5.6.3 Rectified spirits

6 Reactions6.1 Ester formation6.2 Dehydration6.3 Combustion6.4 Acid-base chemistry6.5 Halogenation6.6 Oxidation

7 Uses7.1 As a fuel7.2 Alcoholic beverages7.3 Feedstock7.4 Antiseptic7.5 Treatment for poisoning by other alcohols7.6 Solvent7.7 Historical uses

8 Pharmacology9 Drug effects

9.1 Short-term9.1.1 Effects on the central nervous system9.1.2 Effects on metabolism9.1.3 Drug interactions9.1.4 Magnitude of effects

9.2 Long-term9.2.1 Birth defects9.2.2 Other effects

10 Natural occurrence11 See also

Systematic name

Other names

Ethanol - Wikipedia, the free encyclopedia http://en.wikipedia.org/wiki/Ethanol

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3DMet B01253

Jmol-3D images Image 1(http://chemapps.stolaf.edu/jmol/jmol.php?model=CCO)

Properties

Molecular formula C2H6O

Molar mass 46.07 g mol−1

Appearance Colorless liquid

Density 0.789 g/cm3

Melting point−114 °C, 159 K, -173 °F

Boiling point78.37 °C, 352 K, 173 °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),0.001074 Pa s (at 25 °C)[3]

Dipole moment 1.69 D[4]

Pharmacology

Routes ofadministration

Intramuscular

IntravenousOralTopical

Metabolism Hepatic

Hazards

MSDS External MSDS

EU Index 603-002-00-5

EU classificationF

R-phrases R11

S-phrases (S2), S7, S16

NFPA 704

Flash point 13–14 °C

Autoignitiontemperature

362 °C

LD50 5628 mg kg−1 (oral, rat)

Supplementary data page

Structure andproperties

n, εr, etc.

12 References13 Further reading14 Appendix15 External links

Chemical formula

Ethanol is a 2-carbon alcohol with the molecular formula CH3CH2OH. Itsempirical formula is C2H6O. An alternative notation is CH3–CH2–OH, whichindicates that the carbon of a methyl group (CH3–) is attached to the carbon of amethylene group (–CH2–), which is attached to the oxygen of a hydroxyl group(–OH). It is a constitutional isomer of dimethyl ether. Ethanol is often abbreviatedas EtOH, using the common organic chemistry notation of representing the ethylgroup (C2H5) with Et.

Name

Ethanol is the systematic name defined by the IUPAC nomenclature of organicchemistry for a molecule with two carbon atoms (prefix "eth-"), having a singlebond between them (suffix "-ane"), and an attached -OH group (suffix "-ol").[5]

History

For more details on this topic, see Distilled beverage.

The fermentation of sugar into ethanol is one of the earliest biotechnologiesemployed by humanity. The intoxicating effects of ethanol consumption have beenknown since ancient times. Ethanol has been used by humans since prehistory asthe intoxicating ingredient of alcoholic beverages. Dried residue on 9,000-year-oldpottery found in China imply that Neolithic people consumed alcoholicbeverages.[6]

Although distillation was well known by the early Greeks and Arabs, the firstrecorded production of alcohol from distilled wine was by the School of Salernoalchemists in the 12th century.[7] The first to mention absolute alcohol, in contrastwith alcohol-water mixtures, was Raymond Lull.[7]

In 1796, Johann Tobias Lowitz obtained pure ethanol by mixing partially purifiedethanol (the alcohol-water azeotrope) with an excess of anhydrous alkali and thendistilling the mixture over low heat.[8] Antoine Lavoisier described ethanol as acompound of carbon, hydrogen, and oxygen, and in 1807 Nicolas-Théodore deSaussure determined ethanol's chemical formula.[9][10] Fifty years later, ArchibaldScott Couper published the structural formula of ethanol. It is one of the firststructural formulas determined.[11]

Ethanol was first prepared synthetically in 1825 by Michael Faraday. He foundthat sulfuric acid could absorb large volumes of coal gas.[12] He gave the resultingsolution to Henry Hennell, a British chemist, who found in 1826 that it contained"sulphovinic acid" (ethyl hydrogen sulfate).[13] In 1828, Hennell and the Frenchchemist Georges-Simon Sérullas independently discovered that sulphovinic acidcould be decomposed into ethanol.[14][15] Thus, in 1825 Faraday had unwittinglydiscovered that ethanol could be produced from ethylene (a component of coalgas) by acid-catalyzed hydration, a process similar to current industrial ethanolsynthesis.[16]

SMILES

InChI


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Thermodynamicdata

Phase behaviourSolid, liquid, gas

Spectral data UV, IR, NMR, MS

(verify) (what is: / ?)Except where noted otherwise, data are given for

materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Ethanol burning with itsspectrum depicted

Ethanol was used as lamp fuel in the United States as early as 1840, but a taxlevied on industrial alcohol during the Civil War made this use uneconomical. Thetax was repealed in 1906.[17] Original Ford Model T automobiles ran on ethanoluntil 1908.[18] With the advent of Prohibition in 1920, ethanol fuel sellers wereaccused of being allied with moonshiners,[17] and ethanol fuel fell into disuse untillate in the 20th century.

In modern times, ethanol intended for industrial use is also produced fromethylene.[19] Ethanol has widespread use as a solvent of substances intended forhuman contact or consumption, including scents, flavorings, colorings, and medicines. In chemistry, it is both an essential solvent anda 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 forinternal combustion engines.

Physical properties

Ethanol is a volatile, colorless liquid that has a slight odor.[20] It burns with a smokeless blue flamethat is not always visible in normal light.

The physical properties of ethanol stem primarily from the presence of its hydroxyl group and theshortness 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 molecularweight, such as propane.

Ethanol is slightly more refractive than water, having a refractive index of 1.36242 (at λ=589.3 nmand 18.35 °C).[21]

The triple point for ethanol is 150 K at a pressure of 4.3 * 10-4 Pa.[22]

Solvent properties

Ethanol is a versatile solvent, miscible with water and with many organic solvents, including aceticacid, acetone, benzene, carbon tetrachloride, chloroform, diethyl ether, ethylene glycol, glycerol,nitromethane, pyridine, and toluene.[21][23] It is also miscible with light aliphatic hydrocarbons, such

as pentane and hexane, and with aliphatic chlorides such as trichloroethane and tetrachloroethylene.[23]

Ethanol's miscibility with water contrasts with the immiscibility of longer-chain alcohols (five or more carbon atoms), whose watermiscibility decreases sharply as the number of carbons increases.[24] The miscibility of ethanol with alkanes is limited to alkanes upto undecane, mixtures with dodecane and higher alkanes show a miscibility gap below a certain temperature (about 13 °C fordodecane[25]). 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 volumesof ethanol and water results in only 1.92 volumes of mixture.[21][26] Mixing ethanol and water is exothermic, with up to777 J/mol[27] being released at 298 K.

Mixtures of ethanol and water form an azeotrope at about 89 mole-% ethanol and 11 mole-% water[28] or a mixture of about 96volume percent ethanol and 4% water at normal pressure and T = 351 K. This azeotropic composition is strongly temperature- andpressure-dependent and vanishes at temperatures below 303 K.[29]

Hydrogen bonding causes pure ethanol to be hygroscopic to the extent that it readily absorbs water from the air. The polar nature ofthe hydroxyl group causes ethanol to dissolve many ionic compounds, notably sodium and potassium hydroxides, magnesiumchloride, calcium chloride, ammonium chloride, ammonium bromide, and sodium bromide.[23] Sodium and potassium chlorides areslightly soluble in ethanol.[23] Because the ethanol molecule also has a nonpolar end, it will also dissolve nonpolar substances,including most essential oils[30] 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 explainsthe "tears of wine" phenomenon. When wine is swirled in a glass, ethanol evaporates quickly from the thin film of wine on the wallof the glass. As the wine's ethanol content decreases, its surface tension increases and the thin film "beads up" and runs down the


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Hydrogen bonding in solid ethanol at −186 °C

94% denatured ethanol soldin a bottle for household use

glass in channels rather than as a smooth sheet.

Flammability

An ethanol-water solution that contains 40% ABV will catch fire if heated toabout 26 °C (79 °F) and if an ignition source is applied to it. This is called itsflash point.[31] The flash point of pure ethanol is 16.60 °C (61.88 °F), less thanaverage room temperature.[32]

The flash points of ethanol concentrations from 10% ABV to 96% ABV areshown below:[33]

10% — 49 °C (120 °F)12.5% — about 52 °C (126 °F)20% — 36 °C (97 °F)30% — 29 °C (84 °F)40% — 26 °C (79 °F)50% — 24 °C (75 °F)60% — 22 °C (72 °F)70% — 21 °C (70 °F)80% — 20 °C (68 °F)90% — 17 °C (63 °F)96% — 17 °C (63 °F)

Alcoholic beverages that have a low concentration of ethanol will burn if sufficiently heated and an ignition source (such as anelectric spark or a match) is applied to them. For example, the flash point of ordinary wine containing 12.5% ethanol is about 52 °C(126 °F).[34]

Production

Ethanol is produced both as a petrochemical, through the hydration of ethylene and, via biologicalprocesses, by fermenting sugars with yeast.[35] Which process is more economical depends onprevailing prices of petroleum and grain feed stocks.

Ethylene hydration

Ethanol for use as an industrial feedstock or solvent (sometimes referred to as synthetic ethanol) ismade 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,[36] adsorbed onto a porous support such as silica gelor diatomaceous earth. This catalyst was first used for large-scale ethanol production by the Shell OilCompany in 1947.[37] The reaction is carried out with an excess of high pressure steam at 300 °C. Inthe U.S., this process was used on an industrial scale by Union Carbide Corporation and others; butnow only LyondellBasell uses it commercially.

In an older process, first practiced on the industrial scale in 1930 by Union Carbide,[38] but now almost entirely obsolete, ethylenewas hydrated indirectly by reacting it with concentrated sulfuric acid to produce ethyl sulfate, which was hydrolysed to yield ethanoland regenerate the sulfuric acid:[39]

C2H4 + H2SO4 → CH3CH2SO4HCH3CH2SO4H + H2O → CH3CH2OH + H2SO4

Fermentation

Main article: Ethanol fermentation


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See also: Yeast in winemaking

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 in reduced-oxygen conditions they produce ethanoland carbon dioxide. The chemical equations below summarize the conversion:

C6H12O6 → 2 CH3CH2OH + 2 CO2C12H22O11 + H2O → 4 CH3CH2OH + 4 CO2

Fermentation is the process of culturing yeast under favorable thermal conditions to produce alcohol. This process is carried out ataround 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 toapproximately 15% ethanol by volume.[40]

To produce ethanol from starchy materials such as cereal grains, the starch must first be converted into sugars. In brewing beer, thishas traditionally been accomplished by allowing the grain to germinate, or malt, which produces the enzyme amylase. When themalted grain is mashed, the amylase converts the remaining starches into sugars. For fuel ethanol, the hydrolysis of starch intoglucose can be accomplished more rapidly by treatment with dilute sulfuric acid, fungally produced amylase, or some combination ofthe two.[41]

Cellulosic ethanol

Main article: Cellulosic ethanol

Sugars for ethanol fermentation can be obtained from cellulose.[42][43] Until recently, however, the cost of the cellulase enzymescapable of hydrolyzing cellulose has been prohibitive. The Canadian firm Iogen brought the first cellulose-based ethanol planton-stream in 2004.[44] Its primary consumer so far has been the Canadian government, which, along with the United StatesDepartment of Energy, has invested heavily in the commercialization of cellulosic ethanol. Deployment of this technology could turna 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, andhemicellulase enzymes. These would convert agricultural residues such as corn stover, wheat straw, and sugar cane bagasse andenergy crops such as switchgrass into fermentable sugars.[45]

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 ethanolproduction, cannot metabolize xylose. Other yeasts and bacteria are under investigation to ferment xylose and other pentoses intoethanol.[46]

On January 14, 2008, General Motors announced a partnership with Coskata, Inc. The goal was to produce cellulosic ethanolcheaply, with an eventual goal of US$1 per US gallon ($0.30/L) for the fuel. The partnership planned to begin producing the fuel inlarge quantity by the end of 2008, and by 2011 to have a full-scale plant 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).[47] In October 2011, an article on theCoskata website stated that a "semi-commercial" pilot plant in Madison, Pennsylvania, had been running successfully for 2 years andthat a full scale facility was planned for Alabama.[48]

Hydrocarbon-based ethanol production

A process developed and marketed by Celanese Corporation under the name TCX Technology uses hydrocarbons such as natural gasor coal for ethanol production rather than using fermented crops such as corn or sugarcane.[49]

Prospective technologies

The anaerobic bacterium Clostridium ljungdahlii, discovered in commercial chicken wastes, can produce ethanol from single-carbonsources including synthesis gas, a mixture of carbon monoxide and hydrogen that can be generated from the partial combustion ofeither fossil fuels or biomass. Use of these bacteria to produce ethanol from synthesis gas has progressed to the pilot plant stage at theBRI Energy facility in Fayetteville, Arkansas.[50] 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 stover.[51]


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Ethanol plant in Turner County, SouthDakota

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

Near infrared spectrum of liquid ethanol.

Another prospective technology is the closed-loop ethanol plant.[52] Ethanol produced fromcorn has a number of critics who suggest that it is primarily just recycled fossil fuels becauseof the energy required to grow the grain and convert it into ethanol. There is also the issue ofcompetition with use of corn for food production. However, the closed-loop ethanol plantattempts to address this criticism. In a closed-loop plant, renewable energy for distillationcomes from fermented manure, produced from cattle that have been fed the DDSGby-products from grain ethanol production. The concentrated compost nutrients from manureare then used to fertilize the soil and grow the next crop of grain to start the cycle again. Sucha process is expected to lower the fossil fuel consumption used during conversion to ethanolby 75%.[53]

An alternative technology allows for the production of biodiesel from distillers grain as anadditional value product.[54] Though in an early stage of research, there is some developmentof 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.[55]

Testing

Breweries and biofuel plants employ two methods for measuring ethanolconcentration. Infrared ethanol sensors measure the vibrational frequency ofdissolved ethanol using the CH band at 2900 cm−1. This method uses a relativelyinexpensive solid state sensor that compares the CH band with a reference bandto calculate the ethanol content. The calculation makes use of the Beer-Lambertlaw. Alternatively, by measuring the density of the starting material and thedensity of the product, using a hydrometer, the change in specific gravity duringfermentation indicates the alcohol content. This inexpensive and indirect methodhas a long history in the beer brewing industry.

Purification

Main article: Ethanol purification

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

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

In another method to obtain absolute alcohol, a small quantity of benzene isadded to rectified spirit and the mixture is then distilled. Absolute alcohol isobtained in the third fraction, which distills over at 78.3 °C (351.4 K).[24]

Because a small amount of the benzene used remains in the solution, absolutealcohol produced by this method is not suitable for consumption, as benzene is carcinogenic.[56]

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

Grades of ethanol

Denatured alcohol

Main article: Denatured alcohol


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Pure ethanol and alcoholic beverages are heavily taxed as a psychoactive drug, but ethanol has many uses that do not involveconsumption by humans. To relieve the tax burden on these uses, most jurisdictions waive the tax when an agent has been added tothe 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.[57][58]

Absolute alcohol

Absolute or anhydrous alcohol refers to ethanol with a low water content. There are various grades with maximum water contentsranging from 1% to ppm levels. Absolute alcohol is not intended for human consumption. If azeotropic distillation is used to removewater, it will contain trace amounts of the material separation agent (e.g. benzene).[59] Absolute ethanol is used as a solvent forlaboratory and industrial applications, where water will react with other chemicals, and as fuel alcohol. Spectroscopic ethanol is anabsolute ethanol with a low absorbance in ultraviolet and visible light, fit for use as a solvent in ultraviolet-visible spectroscopy.[60]

Pure ethanol is classed as 200 proof in the USA, equivalent to 175 degrees proof in the UK system.[61]

Rectified spirits

Rectified spirit, an azeotropic composition containing 4% water, is used instead of anhydrous ethanol for various purposes. Winespirits are about 188 proof. The impurities are different from those in 190 proof laboratory ethanol.[62]

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 atomsattached 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 isformed. Esters react in the presence of an acid or base to give back the alcohol and a salt. This reaction is known as saponificationbecause it is used in the preparation of soap. Ethanol can also form esters with inorganic acids. Diethyl sulfate and triethyl phosphateare prepared by treating ethanol with sulfur trioxide and phosphorus pentoxide respectively. Diethyl sulfate is a useful ethylatingagent in organic synthesis. Ethyl nitrite, prepared from the reaction of ethanol with sodium nitrite and sulfuric acid, was formerly awidely used diuretic.

Dehydration

Strong acid desiccants cause the dehydration of ethanol to form diethyl ether and other byproducts. If the dehydration temperatureexceeds around 160 °C, ethylene will be the main product. Millions of kilograms of diethyl ether are produced annually using sulfuricacid 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); (ΔHc = −1371 kJ/mol[63]) 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


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Energy content of some fuels compared with ethanol:[65]

Fuel type MJ/L MJ/kgResearch

octanenumber

Dry wood (20% moisture) ~19.5

Methanol 17.9 19.9 108.7[66]

Ethanol 21.2[67] 26.8[67] 108.6[66]

E85(85% ethanol, 15% gasoline) 25.2 33.2 105

Liquefied natural gas 25.3 ~55

Autogas (LPG)(60% propane + 40% butane) 26.8 50.

its conjugate base, the ethoxide ion (CH3CH2O−), by reaction with an alkali metal such as sodium:[24]

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 ethoxideand 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 halidesto 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.[39] HBr requires refluxing with a sulfuric acid catalyst.[39] Ethyl halides can,in principle, also be produced by treating ethanol with more specialized halogenating agents, such as thionyl chloride or phosphorustribromide.[24][39]

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). Thisconversion is called the haloform reaction.[64] " 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.[39] Thisoxidation is of no importance industrially, but in the human body, these oxidation reactions are catalyzed by the enzyme liver alcoholdehydrogenase. The oxidation product of ethanol, acetic acid, is a nutrient for humans, being a precursor to acetyl CoA, where theacetyl group can be spent as energy or used for biosynthesis.

Uses

As a fuel

Main article: Ethanol fuel

The largest single use of ethanol is as a motor fuel andfuel additive. More than any other major country, Brazilrelies on ethanol as a motor fuel. Gasoline sold in Brazilcontains at least 25% anhydrous ethanol. Hydrousethanol (about 95% ethanol and 5% water) can be usedas fuel in more than 90% of new cars sold in thecountry. Brazilian ethanol is produced from sugar caneand noted for high carbon sequestration.[69] The USuses Gasohol (max 10% ethanol) and E85 (85%ethanol) ethanol/gasoline mixtures.

Ethanol may also be utilized as a rocket fuel, and iscurrently in lightweight rocket-powered racingaircraft.[70]


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Aviation gasoline(high-octane gasoline, not jet fuel) 33.5 46.8 100/130 (lean/rich)

Gasohol(90% gasoline + 10% ethanol) 33.7 47.1 93/94

Regular gasoline/petrol 34.8 44.4[68] min. 91

Premium gasoline/petrol max. 104

Diesel 38.6 45.4 25Charcoal, extruded 50 23

USP grade ethanol forlaboratory use.

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

A Ford Taurus "fueled by cleanburning ethanol" owned by New YorkCity.

Australian law limits of the use of pure ethanol sourcedfrom sugarcane waste to up to 10% in automobiles. Ithas been recommended that older cars (and vintage carsdesigned to use a slower burning fuel) have their valvesupgraded or replaced.[71]

According to an industry advocacy group for promotingethanol called the American Coalition for Ethanol,ethanol as a fuel reduces harmful tailpipe emissions ofcarbon monoxide, particulate matter, oxides of nitrogen,and other ozone-forming pollutants.[72] ArgonneNational Laboratory analyzed the greenhouse gas emissions of many different engine and fuelcombinations. Comparing ethanol blends with gasoline alone, they showed reductions of 8% with thebiodiesel/petrodiesel blend known as B20, 17% with the conventional E85 ethanol blend, and thatusing cellulosic ethanol lowers emissions 64%.[73]

Ethanol combustion in an internal combustion engine yields many of the products of incompletecombustion produced by gasoline and significantly larger amounts of formaldehyde and relatedspecies such as acetaldehyde.[74] This leads to a significantly larger photochemical reactivity thatgenerates much more ground level ozone.[75] These data have been assembled into The Clean FuelsReport comparison of fuel emissions[76] and show that ethanol exhaust generates 2.14 times as muchozone as does gasoline exhaust.[citation needed] When this is added into the custom LocalisedPollution Index (LPI) of The Clean Fuels Report the local pollution (pollution that contributes tosmog) is 1.7 on a scale where gasoline is 1.0 and higher numbers signify greater pollution.[citation needed] The California Air Resources Board formalized this issue in 2008 by recognizingcontrol standards for formaldehydes as an emissions control group, much like the conventional NOxand Reactive Organic Gases (ROGs).[77]

World production of ethanol in 2006 was 51 gigalitres(1.3 × 1010 US gal), with 69% of the world supply comingfrom Brazil and the United States.[78] More than 20% of Brazilian cars are able to use 100%ethanol as fuel, which includes ethanol-only engines and flex-fuel engines.[79] Flex-fuelengines in Brazil are able to work with all ethanol, all gasoline or any mixture of both. In theUS flex-fuel vehicles can run on 0% to 85% ethanol (15% gasoline) since higher ethanolblends are not yet allowed or efficient. Brazil supports this population of ethanol-burningautomobiles with large national infrastructure that produces ethanol from domestically grownsugar cane. Sugar cane not only has a greater concentration of sucrose than corn (by about30%), but is also much easier to extract. The bagasse generated by the process is not wasted,but is used in power plants to produce electricity.[citation needed]

The United States fuel ethanol industry is based largely on corn. According to the RenewableFuels Association, as of October 30, 2007, 131 grain ethanol bio-refineries in the UnitedStates have the capacity to produce 7.0 billion US gallons (26,000,000 m3) of ethanol peryear. An additional 72 construction projects underway (in the U.S.) can add 6.4 billion USgallons (24,000,000 m3) of new capacity in the next 18 months. Over time, it is believed thata material portion of the ≈150-billion-US-gallon (570,000,000 m3) per year market forgasoline will begin to be replaced with fuel ethanol.[80]

One problem with ethanol is its high miscibility withwater, which means that it cannot be efficientlyshipped through modern pipelines, like liquidhydrocarbons, over long distances.[81] Mechanics alsohave seen increased cases of damage to small engines,

in particular, the carburetor, attributable to the increased water retention by ethanol infuel.[82]

In 2011, the Open Fuel Standard Coalition introduced a bill into Congress that would mandate


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United States Postal Service vehiclerunning on E85, a "flex-fuel" blend inSaint Paul, Minnesota.

most cars sold in the United States to be warranted to run on ethanol, as well as methanol andgasoline. The bill aims to provide enough financial incentive to find better ways to makeethanol fuel so it could compete economically against gasoline.[citation needed]

Alcoholic beverages

Main article: Alcoholic beverage

Ethanol is the principal psychoactive constituent in alcoholic beverages, with depressant effects on the central nervous system. It hasa complex mode of action and affects multiple systems in the brain, the most notable one being its agonistic action on the GABAreceptors.[83] Similar psychoactives include those that also interact with GABA receptors, such as benzodiazepines, barbiturates,gamma-hydroxybutyric acid (GHB).[84] Ethanol is metabolized by the body as an energy-providing nutrient, as it metabolizes intoacetyl CoA, an intermediate common with glucose and fatty acid metabolism that can be used for energy in the citric acid cycle orfor biosynthesis.

Alcoholic beverages vary considerably in ethanol content and in foodstuffs they are produced from. Most alcoholic beverages can bebroadly 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 abeverage is usually measured in terms of the volume fraction of ethanol in the beverage, expressed either as a percentage or inalcoholic proof units.

Fermented beverages can be broadly classified by the foodstuff they are fermented from. Beers are made from cereal grains or otherstarchy materials, wines and ciders from fruit juices, and meads from honey. Cultures around the world have made fermentedbeverages 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, distilledfrom fermented cereal grains; brandies, distilled from fermented fruit juices; and rum, distilled from fermented molasses or sugarcanejuice. Vodka and similar neutral grain spirits can be distilled from any fermented material (grain and potatoes are most common);these spirits are so thoroughly distilled that no tastes from the particular starting material remain. Numerous other spirits and liqueursare prepared by infusing flavors from fruits, herbs, and spices into distilled spirits. A traditional example is gin, which is created byinfusing juniper berries into a neutral grain alcohol.

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

Alcoholic beverages are used in cooking for their flavors and because alcohol dissolves hydrophobic flavor compounds.

Just as industrial ethanol is used as feedstock for the production of industrial acetic acid, alcoholic beverages are made into 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

Ethanol is an important industrial ingredient and has widespread use as a base chemical for other organic compounds. These includeethyl 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 anantiseptic. Ethanol kills organisms by denaturing their proteins and dissolving their lipids and is effective against most bacteria andfungi, and many viruses, but is ineffective against bacterial spores.[85]

Treatment for poisoning by other alcohols

Ethanol is sometimes used to treat poisoning by other, more toxic alcohols, in particular methanol[86] and ethylene glycol. Ethanol


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BAC(g/L)

BAC(% v/v) Symptoms[94]

0.5 0.05% Euphoria, talkativeness, relaxation

1 0.1 %Central nervous system depression, nausea,possible vomiting, impaired motor andsensory function, impaired cognition

>1.4 >0.14% Decreased blood flow to brain3 0.3% Stupefaction, possible unconsciousness

4 0.4% Possible death

>5.5 >0.55% Death

competes with other alcohols for the alcohol dehydrogenase enzyme, lessening metabolism into toxic aldehyde and carboxylic acidderivatives,[87] 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 careproducts such as perfumes and deodorants. It may also be used as a solvent or solute 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 atruth 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 asliquid oxygen. The German V-2 rocket of World War II, credited with beginning the space age, used ethanol, mixed with 25% ofwater to reduce the combustion chamber temperature.[88][89] The V-2's design team helped develop U.S. rockets following WorldWar II, including the ethanol-fueled Redstone rocket, which launched the first U.S. satellite.[90] Alcohols fell into general disuse asmore efficient rocket fuels were developed.[89]

Pharmacology

Ethanol binds to acetylcholine, GABA, serotonin, and NMDA receptors. It also appears to cause an increase in dopamine through apoorly understood process that may involve inhibiting the enzyme that breaks dopamine down.[91]

The removal of ethanol through oxidation by alcohol dehydrogenase in the liver from the human body is limited. Hence, the removalof a large concentration of alcohol from blood may follow zero-order kinetics. This means that alcohol leaves the body at a constantrate, 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 alcoholconcentration can be used to modify the biochemistry of methanol and ethylene glycol. Methanol itself is not highly toxic, but itsmetabolites formaldehyde and formic acid are; therefore, to reduce the concentration of these harmful metabolites, ethanol can beingested to reduce the rate of methanol metabolism due to shared rate-limiting steps. Ethylene glycol poisoning can be treated in thesame way.

Drug effects

Pure ethanol will irritate the skin and eyes.[92] Nausea, vomiting and intoxication are symptoms of ingestion. Long-term use byingestion can result in serious liver damage.[93] Atmospheric concentrations above one in a thousand are above the European UnionOccupational exposure limits.[93]

Short-term

Main article: Short-term effects of alcohol

Effects on the central nervous system

Ethanol is a central nervous system depressant and has significantpsychoactive effects in sublethal doses; for specifics, see "Effects ofalcohol on the body by dose". Based on its abilities to change thehuman consciousness, ethanol is considered a psychoactivedrug.[95] Death from ethanol consumption is possible when bloodalcohol level reaches 0.4%. A blood level of 0.5% or more iscommonly fatal. Levels of even less than 0.1% can causeintoxication, with unconsciousness often occurring at 0.3–0.4%.[96]

The amount of ethanol in the body is typically quantified by blood


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

Ethanol acts in the central nervous system by binding to the GABA-A receptor, increasing the effects of the inhibitoryneurotransmitter GABA (i.e., it is a positive allosteric modulator).[97]

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

According to the US National Highway Traffic Safety Administration, in 2002 about "41% of people fatally injured in traffic crasheswere in alcohol related crashes".[98] The risk of a fatal car accident increases exponentially with the level of alcohol in the driver'sblood.[99] Most drunk driving laws governing the acceptable levels in the blood while driving or operating heavy machinery settypical 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 heavydrinking to undertake an alcohol detoxification regimen.

The reinforcing effects of alcohol consumption are also mediated by acetaldehyde generated by catalase and other oxidizing enzymessuch as cytochrome P-4502E1 in the brain.[100] Although acetaldehyde has been associated with some of the adverse and toxiceffects of ethanol, it appears to play a central role in the activation of the mesolimbic dopamine system.[101]

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 the acetyl in acetyl CoA byacetaldehyde dehydrogenase. Acetyl CoA is the final product of both carbohydrate and fat metabolism, where the acetyl can befurther used to produce energy or for biosynthesis. As such, ethanol is a nutrient. However, the product of the first step of thisbreakdown, acetaldehyde,[102] is more toxic than ethanol. Acetaldehyde is linked to most of the clinical effects of alcohol. It hasbeen shown to increase the risk of developing cirrhosis of the liver[84] and multiple forms of cancer.

Drug interactions

Ethanol can intensify the sedation caused by other central nervous system depressant drugs such as barbiturates, benzodiazepines,opioids, phenothiazines, and anti-depressants.[96]

Magnitude of effects

Some individuals have less effective forms of one or both of the metabolizing enzymes, and can experience more severe symptomsfrom ethanol consumption than others. However, those having acquired alcohol tolerance have a greater quantity of these enzymes,and metabolize ethanol more rapidly.[103]

Long-term

Main article: Long-term effects of alcohol

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


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triglycerides.[104]

Ethanol is not a carcinogen.[105][106] However, the first metabolic product of ethanol, acetaldehyde, is toxic, mutagenic, andcarcinogenic.

Ethanol is also widely used, clinically and over the counter, as an antitussive agent.[107]

Natural occurrence

Ethanol is a byproduct of the metabolic process of yeast. As such, ethanol will be present in any yeast habitat. Ethanol cancommonly be found in overripe fruit.[108] Ethanol produced by symbiotic yeast can be found in Bertam Palm blossoms. Althoughsome species such as the Pentailed Treeshrew exhibit ethanol seeking behaviors, most show no interest or avoidance of food sourcescontaining ethanol.[109] Ethanol is also produced during the germination of many plants as a result of natural anerobiosis.[110]

Ethanol has been detected in outer space, forming an icy coating around dust grains in interstellar clouds.[111]

See also

1-Propanol2,2,2-TrichloroethanolAlcoholic beveragesBreathalyzerButanol fuel

Cellulosic ethanolcommercializationDistilled beveragesEthenolEthynol

Isopropyl alcoholOutline of energyRubbing alcoholTimeline of alcohol fuel

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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(1972–2003) (http://etoh.niaaa.nih.gov/Archive.htm) Alcohol and Alcohol Problems Science Database.Boyce, John M., and Pittet Didier. (2003). "Hand Hygiene in Healthcare Settings." (http://cdc.gov/handhygiene/) Centers for DiseaseControl, Atlanta, Georgia, United States.Sci-toys website explanation of US denatured alcohol designations (http://sci-toys.com/ingredients/alcohol.html)Smith, M.G., and M. Snyder. (2005). "Ethanol-induced virulence of Acinetobacter baumannii". American Society for Microbiologymeeting. Volume 1 June 5 – June 9. Atlanta.

Appendix


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Thermophysical properties of mixtures of ethanol with water and dodecane

Excess volume of the mixture of ethanoland water (volume contraction)

Heat of mixing of the mixture of ethanoland water

Vapor-liquid equilibrium of the mixture ofethanol and water (including azeotrope)

Solid-liquid equilibrium of the mixture ofethanol and water (including eutecticum)

Miscibility gap in the mixture of dodecaneand ethanol

External links

International Labour Organization (http://www.inchem.org/documents/icsc/icsc/eics0044.htm) ethanol safety informationNational 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) chemicaldata on ethanolChEBI – 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 futuresCalculation 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 ethanolU.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 ethanolChemSub Online: Ethyl alcohol (http://chemsub.online.fr/name/ethyl_alcohol.html)

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