Ethanol 10048 225958854 2008-07-16T05:28:06Z Rifleman 82 1255637 Reverted edits by [[Special:Contributions/71.200.255.220|71.200.255.220]] ([[User talk:71.200.255.220|talk]]) to last version by Davumaya {{Redirect|Grain alcohol|the distilled high-proof liquor of similar name|neutral grain spirits}} {{for|the use of ethanol as a substitute for gasoline|Ethanol fuel}} {{otheruses3|Ethanol (disambiguation)}} {{Chembox new | ImageFile = Ethanol-2D-skeletal.svg | ImageFile1 = Ethanol-3D-vdW.png | IUPACName = Ethanol | OtherNames = Ethyl alcohol; grain alcohol; hydroxyethane; drinking alcohol; ethyl hydrate | Section1 = {{Chembox Identifiers | SMILES = CCO | CASNo = 64-17-5 | RTECS = KQ6300000 }} | Section2 = {{Chembox Properties | Formula = CH<sub>3</sub>CH<sub>2</sub>OH | MolarMass = 46.06844(232) g/mol | Appearance = colorless clear liquid | Density = 0.789 g/cm³, liquid | Solubility = Fully [[miscible]] | MeltingPt = −114.3 °C (158.8 K) | BoilingPt = 78.4 °C (351.6 K) | pKa = 15.9 | Viscosity = 1.200 mPa·s ([[Poise|cP]]) at 20.0 °C | Dipole = 5.64 fC·fm (1.69 [[Debye|D]]) (gas) }} | Section7 = {{Chembox Hazards | FlashPt = 286.15 K (13 °C or 55.4 °F) | EUClass = Flammable ('''F''') | NFPA-H = 2 | NFPA-F = 3 | NFPA-R = 1 | RPhrases = {{R11}} | SPhrases = {{S2}}, {{S7}}, {{S16}} }} | Section8 = {{Chembox Related | Function = [[alcohol]]s }} }} '''Ethanol''', also called '''ethyl alcohol''', '''grain alcohol''', or '''drinking alcohol''', is a volatile, [[flammable]], colorless liquid. It is best known as the type of [[alcohol]] found in [[alcoholic beverages]] and in thermometers. In common usage, it is often referred to simply as ''alcohol''. Ethanol is also known as '''EtOH''', using the common organic chemistry notation of representing the ethyl group (C<sub>2</sub>H<sub>5</sub>) with '''Et'''. Ethanol is a straight-chain alcohol, and its [[chemical formula|molecular formula]] is C<sub>2</sub>H<sub>5</sub>OH. An alternative notation is CH<sub>3</sub>-CH<sub>2</sub>-OH, which indicates that the carbon of a methyl group (CH<sub>3</sub>-) is attached to the carbon of a methylene group (-CH<sub>2</sub>-), which is attached to the oxygen of a [[Hydroxyl|hydroxyl group (-OH)]]. Its [[empirical formula]] is [[Carbon|C]]<sub>2</sub>[[Hydrogen|H]]<sub>6</sub>[[Oxygen|O]], a formula that it shares with [[dimethyl ether]]. Except for the use of fire, the fermentation of sugar into ethanol is very likely the earliest [[organic reaction]] known to humanity,{{Fact|date=February 2008}} and the intoxicating effects of ethanol consumption have been known since ancient times. In modern times, ethanol intended for industrial use is also produced from by-products of petroleum refining. 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 also as a fuel for [[internal combustion engine]]s. == History == [[Image:Alcohol flame.jpg|thumb|left|Ethanol being used as fuel for a burner.]] Ethanol has been used by humans since prehistory as the intoxicating ingredient of [[alcoholic beverage]]s. Dried residues on 9000-year-old pottery found in China imply that alcoholic beverages were used even among [[Neolithic]] people.<ref name="Roach">{{cite journal|author=Roach, J.|date=July 18, 2005|url=http://news.nationalgeographic.com/news/2005/07/0718_050718_ancientbeer.html|title= 9,000-Year-Old Beer Re-Created From Chinese Recipe.|journal=National Geographic News|accessdate= 2007-09-03}}</ref> Its isolation as a relatively pure compound was first achieved by [[Alchemy (Islam)|Muslim chemists]] who developed the art of [[distillation]] during the [[Abbasid]] [[caliphate]], the most notable of whom were [[Geber|Jabir ibn Hayyan]] (Geber), [[Al-Kindi]] (Alkindus), and [[al-Razi]] (Rhazes, 865–925). Writings attributed to Jabir ibn Hayyan (721–815) mention the flammable vapors of boiled wine. Al-Kindi (801–873) unambiguously described the distillation of wine.<ref name="al-Hassan">{{cite web |url=http://www.history-science-technology.com/Notes/Notes%207.htm |title=Alcohol and the Distillation of Wine in Arabic Sources |accessdate=2008-03-29 |last=Hassan |first=Ahmad Y |authorlink=Ahmad Y Hassan |work=History of Science and Technology in Islam}}</ref> In 1796, Johann Tobias Lowitz obtained pure ethanol by filtering distilled ethanol through [[Activated carbon|activated charcoal]]. [[Antoine Lavoisier]] described ethanol as a compound of carbon, hydrogen, and oxygen, and in 1808 [[Nicolas-Théodore de Saussure]] determined ethanol's chemical formula.<ref>''[http://www.1911encyclopedia.org/Alcohol Alcohol]'' in the [[Encyclopædia Britannica Eleventh Edition]]</ref> Fifty years later, [[Archibald Scott Couper]] published the structural formula of ethanol, which placed ethanol among the first chemical compounds to have their chemical structure determined.<ref name="Couper">{{cite journal|author=Couper, A.S.|year=1858|title=On a new chemical theory|journal=Philosophical magazine | format = online reprint |volume=16|issue=104&ndash;116|url=http://web.lemoyne.edu/~giunta/couper/couper.html|accessdate=2007-09-03}}</ref> Ethanol was first prepared synthetically in 1826 through the independent efforts of Henry Hennel in Great Britain and S.G. Sérullas in France. In 1828, [[Michael Faraday]] prepared ethanol by [[Acid catalysis|acid-catalyzed]] hydration of [[ethylene]], a process similar to that which is used today for industrial ethanol synthesis.<ref name="Hennell">{{cite journal|author=Hennell, H. |year=1828|title=On the mutual action of sulfuric acid and alcohol, and on the nature of the process by which ether is formed.|journal=Philosophical Transactions|volume=118|issue=365&ndash;371}}</ref> Ethanol was used as lamp fuel in the United States as early as 1840, but a tax levied on industrial alcohol during the [[American Civil War|Civil War]] made this use uneconomical. This tax was repealed in 1906,<ref name="siegel">{{cite news|url=http://www.npr.org/templates/story/story.php?storyId=7426827|title=Ethanol, Once Bypassed, Now Surging Ahead|author=Robert Siegel|publisher=NPR|date=2007-02-15|accessdate=2007-09-22}}</ref> and from 1908 onward [[Ford Model T]] automobiles could be adapted to run on ethanol.<ref name="dipardo">{{cite web|url=http://tonto.eia.doe.gov/FTPROOT/features/biomass.pdf|title=Outlook for Biomass Ethanol Production and Demand|publisher=United States Department of Energy|author=Joseph DiPardo|accessdate=2007-09-22}}</ref> With the advent of [[Prohibition]] in 1920 though, sellers of ethanol fuel were accused of being allied with [[moonshine]]rs,<ref name="siegel"/> and ethanol fuel again fell into disuse until late in the 20th century. ==Physical properties== [[Image:Spiritusflamme mit spektrum.png|thumb|right|Ethanol burning with its spectrum depicted.]] [[Image:Chemistry, Combustion of Ethanol 002.jpg|thumb|right|Ethanol burning in a shallow dish.]] Ethanol is a volatile, [[flammable]], colorless liquid that has a strong characteristic odor. It burns with a smokeless blue flame that is not always visible in normal light. The physical properties of ethanol stem primarily from the presence of its [[hydroxyl]] group and the shortness of its carbon chain. Ethanol’s [[hydroxyl]] group is able to participate in hydrogen bonding, rendering it more viscous and less volatile than less polar organic compounds of similar molecular weight. 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]].<ref name="crc"/><ref name="merck"/> It is also miscible with light aliphatic hydrocarbons, such as [[pentane]] and [[hexane]], and with aliphatic chlorides such as [[1,1,1-Trichloroethane|trichloroethane]] and [[tetrachloroethylene]].<ref name="merck">''Merck Index of Chemicals and Drugs'', 9th ed.</ref> Ethanol’s 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.<ref name="m_and_b"/> 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 hydroxide|sodium]] and [[potassium hydroxide]]s, [[magnesium chloride]], [[calcium chloride]], [[ammonium chloride]], [[ammonium bromide]], and [[sodium bromide]].<ref name="merck"/> [[Sodium chloride|Sodium]] and [[potassium chloride]]s are slightly soluble in ethanol.<ref name="merck"/> Because the ethanol molecule also has a nonpolar end, it will also dissolve nonpolar substances, including most [[essential oil]]s<ref name="merckoils">''Merck Index of Chemicals and Drugs'', 9th ed.; monographs 6575 through 6669</ref> and numerous flavoring, coloring, and medicinal agents. Two unusual phenomena are associated with mixtures of ethanol and water. Ethanol-water mixtures have less volume than the sum of their individual components. Mixing equal volumes of ethanol and water results in only 1.92 volumes of mixture.<ref name = "ChemTech"> Kroschwitz and Howe-Grant, editors, ''Encyclopedia of Chemical Technology'', 4th ed., (New York: John Wiley & Sons), vol. 9, 813.</ref><ref name="crc">''CRC Handbook of Chemistry'', 44th ed.</ref> The addition of even a few percent of ethanol to water sharply reduces the [[surface tension]] of water. This property partially explains the “[[tears of wine]]” phenomenon. When wine is swirled in a glass, ethanol evaporates quickly from the thin film of wine on the wall of the glass. As the wine’s ethanol content decreases, its surface tension increases and the thin film “beads up” and runs down the glass in channels rather than as a smooth sheet. Mixtures of ethanol and water that contain more than about 50% ethanol are [[flammable]] and easily ignited. [[Alcoholic proof]] is a widely used measure of how much ethanol (i.e., alcohol) such a mixture contains. In the 18th century, proof was determined by adding a liquor (such as [[rum]]) to gunpowder. If the gunpowder burned, that was considered to be “100% proof” that it was “good” liquor — hence it was called “100 proof.” Ethanol-water solutions that contain less than 50% ethanol may also be flammable if the solution is first heated. Some cooking methods call for [[wine]] to be added to a hot pan, causing it to flash boil into a vapor, which is then ignited to burn off excess alcohol. Ethanol is slightly more refractive than water, having a [[refractive index]] of 1.36242 (at ''λ''=589.3 nm and 18.35 °C).<ref name="crc"/> ==Chemical properties== [[Image:Ethanol-3d-stick-structure.svg|thumb|left|250px|Chemical structure of ethanol]] {{detail|Alcohol}} Ethanol is classified as a primary alcohol, meaning that the carbon to which its hydroxyl group is attached has at least two hydrogen atoms attached to it as well. The chemistry of ethanol is largely that of its [[hydroxyl]] group. === Acid-base chemistry === Ethanol's hydroxyl causes the molecule to be slightly basic. It is however,so very slightly basic it is almost neutral, like pure water. The [[pH]] of 100% ethanol is 7.33, compared to 7.00 for pure water. Ethanol can be quantitatively converted to its [[conjugate base]], the [[Alkoxide|ethoxide]] ion (CH<sub>3</sub>CH<sub>2</sub>O<sup>−</sup>), by reaction with an [[alkali metal]] such as [[sodium]]:<ref name="m_and_b"/> : 2CH<sub>3</sub>CH<sub>2</sub>OH + 2[[sodium|Na]] → 2CH<sub>3</sub>CH<sub>2</sub>ONa + [[hydrogen|H<sub>2</sub>]] or a very strong base such as sodium hydride: : CH<sub>3</sub>CH<sub>2</sub>OH + NaH → CH<sub>3</sub>CH<sub>2</sub>ONa + [[hydrogen|H<sub>2</sub>]] === Halogenation === Ethanol reacts with [[hydrogen halide]]s to produce [[Haloalkane|ethyl halides]] such as [[ethyl chloride]] and [[ethyl bromide]]: : CH<sub>3</sub>CH<sub>2</sub>OH + [[hydrochloric acid|HCl]] → [[ethyl chloride|CH<sub>3</sub>CH<sub>2</sub>Cl]] + [[water|H<sub>2</sub>O]] HCl reaction requires a catalyst such as [[zinc chloride]].<ref name="s_and_h">{{cite book|author=Streitweiser, Andrew Jr.; Heathcock, Clayton H.|title=Introduction to Organic Chemistry|date=1976|publisher=MacMillan|isbn=0-02-418010-6}}</ref> Hydrogen chloride in the presence of their respective zinc chloride is known as [[Lucas reagent]].<ref name="m_and_b"/><ref name="s_and_h"/> : CH<sub>3</sub>CH<sub>2</sub>OH + [[Hydrobromic acid|HBr]] → [[Ethyl bromide|CH<sub>3</sub>CH<sub>2</sub>Br]] + [[water|H<sub>2</sub>O]] HBr requires [[refluxing]] with a [[sulfuric acid]] catalyst.<ref name="s_and_h"/> Ethyl halides can also be produced by reacting ethanol with more specialized [[Halogenation|halogenating agents]], such as [[thionyl chloride]] for preparing ethyl chloride, or [[phosphorus tribromide]] for preparing ethyl bromide.<ref name="m_and_b"/><ref name="s_and_h"/> : CH<sub>3</sub>CH<sub>2</sub>OH + SOCl<sub>2</sub> → CH<sub>3</sub>CH<sub>2</sub>Cl + SO<sub>2</sub> + HCl === Ester formation === Under acid-catalyzed conditions, ethanol reacts with [[carboxylic acid]]s to produce ethyl [[ester]]s and water: : [[carboxylic acid|RCOOH]] + HOCH<sub>2</sub>CH<sub>3</sub> → [[ester|RCOOCH<sub>2</sub>CH<sub>3</sub>]] + [[water|H<sub>2</sub>O]] For this reaction to produce useful yields it is necessary to remove water from the reaction mixture as it is formed. Ethanol can also form esters with inorganic acids. [[Diethyl sulfate]] and [[triethyl phosphate]], prepared by reacting ethanol with [[sulfuric acid|sulfuric]] and [[phosphoric acid]] respectively, are both useful ethylating agents 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, such as sulfuric acid, cause ethanol's dehydration to form either [[diethyl ether]] or [[ethylene]]: : 2 CH<sub>3</sub>CH<sub>2</sub>OH → [[diethyl ether|CH<sub>3</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>3</sub>]] + [[water|H<sub>2</sub>O]] : CH<sub>3</sub>CH<sub>2</sub>OH → [[ethylene|H<sub>2</sub>C=CH<sub>2</sub>]] + [[water|H<sub>2</sub>O]] Which product, diethyl ether or ethylene, predominates depends on the precise reaction conditions. === Oxidation === Ethanol can be oxidized to [[acetaldehyde]], and further oxidized to [[acetic acid]]. In the human body, these oxidation reactions are catalyzed by [[enzyme]]s. In the laboratory, aqueous solutions of strong oxidizing agents, such as [[chromic acid]] or [[potassium permanganate]], oxidize ethanol to acetic acid, and it is difficult to stop the reaction at acetaldehyde at high yield. Ethanol can be oxidized to acetaldehyde, without over oxidation to acetic acid, by reacting it with [[pyridinium chromic chloride]].<ref name="s_and_h"/> The direct oxidation of ethanol to acetic acid using chromic acid is given below. : C<sub>2</sub>H<sub>5</sub>OH + 2[O] → CH<sub>3</sub>COOH + H<sub>2</sub>O The oxidation product of ethanol, acetic acid, is spent as nutrient by the human body as [[acetyl CoA]], where the acetyl group can be spent as energy or used for biosynthesis. === Chlorination === When exposed to [[chlorine]], ethanol is both oxidized and its [[alpha carbon]] chlorinated to form the compound, [[chloral]]. : 4Cl<sub>2</sub> + C<sub>2</sub>H<sub>5</sub>OH → CCl<sub>3</sub>CHO + 5HCl === Combustion === [[Combustion]] of ethanol forms [[carbon dioxide]] and [[water]]: :C<sub>2</sub>H<sub>5</sub>OH(g) + 3 O<sub>2</sub>(g) → 2 CO<sub>2</sub>(g) + 3 H<sub>2</sub>O(l) (&Delta;H<sub>r</sub> = &minus;1409 kJ/mol<ref>{{cite journal | title = Heats of Formation of Simple Organic Molecules | author = Frederick D. Rossini | journal = [[Ind. Eng. Chem.]] | year = 1937 | volume = 29 | issue = 12 | pages = 1424–1430 | doi = 10.1021/ie50336a024}}</ref>) Combustion of ethanol in an internal combustion engine yields many of the products of incomplete combustion that are produced by gasoline and significantly larger amounts of [[formaldehyde]] and related species such as [[formalin]], [[acetaldehyde]], etc..<ref>California Air Resources Board,Definition of a Low Emission Motor Vehicle in Compliance with the Mandates of Health and Safety Code Section 39037.05,second release, October 1989</ref> This leads to a significantly larger photochemical reactivity that generates much more ground level [[ozone]].<ref>A.Lowi& W.P.L.Carter; A Method for Evaluating the Atmospheric Ozone Impact of Actual Vehicle emissions, S.A.E. Technical Paper, Warrendale,PA; march 1990</ref> This data has been assembled into The Clean Fuels Report comparison of fuel emissions<ref>T.T.M.Jones,The Clean Fuels Report: A Quantitative Comparison Of Motor Fuels, Related Pollution and Technologies: 2008.[http://www.cleanfuelsreport.com]</ref> and shows that ethanol exhaust generates 2.14 times as much ozone as does gasoline exhaust. When this is added into the custom "Localised Pollution Index (LPI)" of The Clean Fuels Report the local pollution, i.e. that which contributes to smog, is 1.7 on a scale where gasoline is 1.0 and higher numbers signify greater pollution. This issue has been formalised by the [[California Air Resouces Board]] in 2008<ref>citation needed</ref> by recognising control standards for formaldehydes et al as an emissions control group much like the conventional [[NOx]] and Reactive Organic Gases (ROGs). == Production == [[Image:Ethanol Flasche.jpg|thumb|left|94% denatured ethanol sold in a bottle for household use.]] Ethanol is produced both as a [[petrochemical]], through the hydration of [[ethylene]], and biologically, by [[fermentation (biochemistry)|fermenting]] sugars with [[yeast]].<ref name="Mills-Ecklund">Mills, G.A.; Ecklund, E.E. "[http://arjournals.annualreviews.org/doi/abs/10.1146/annurev.eg.12.110187.000403?journalCode=energy Alcohols as Components of Transportation Fuels]." ''Annual Review of Energy.'' November 1987. Vol. 12, 47–80. Retrieved on [[September 2]], [[2007]].</ref> Which process is more economical is dependent upon the prevailing prices of petroleum and of grain feed stocks. === Ethylene hydration === Ethanol for use as industrial feedstock is most often made from [[petrochemical]] feed stocks, typically by the [[acid]]-[[catalysis|catalyzed]] hydration of [[ethylene]], represented by the [[chemical equation]] : [[ethylene|C<sub>2</sub>H<sub>4</sub>]]<sub>(g)</sub> + [[water|H<sub>2</sub>O]]<sub>(g)</sub> → CH<sub>3</sub>CH<sub>2</sub>OH<sub>(l)</sub> The catalyst is most commonly [[phosphoric acid]],<ref name="r_and_c">{{cite book|author=Roberts, John D.; Caserio, Marjorie C.|date=1977|publisher=W. A. Benjamin, Inc|title=Basic Principles of Organic Chemistry|isbn=0-8053-8329-8}}</ref> [[adsorption|adsorbed]] onto a porous support such as [[diatomaceous earth]] or [[charcoal]]. This catalyst was first used for large-scale ethanol production by the [[Shell Oil Company]] in 1947.<ref name="ECT4 820">Lodgsdon, J.E. (1994). "Ethanol." In J.I. Kroschwitz (Ed.) ''Encyclopedia of Chemical Technology, 4th ed.'' vol. 9, p. 820. New York: John Wiley & Sons.</ref> The reaction is carried out with an excess of high pressure steam at 300 °C. In an older process, first practiced on the industrial scale in 1930 by [[Union Carbide]],<ref name="ECT4 817">Lodgsdon, J.E. (1994). p. 817</ref> but now almost entirely obsolete, ethylene was hydrated indirectly by reacting it with concentrated [[sulfuric acid]] to produce [[ethyl sulfate]], which was then [[hydrolysis|hydrolyzed]] to yield ethanol and regenerate the sulfuric acid:<ref name="s_and_h"/> : [[ethylene|C<sub>2</sub>H<sub>4</sub>]] + [[sulfuric acid|H<sub>2</sub>SO<sub>4</sub>]] → [[ethyl sulfate|CH<sub>3</sub>CH<sub>2</sub>SO<sub>4</sub>H]] : [[ethyl sulfate|CH<sub>3</sub>CH<sub>2</sub>SO<sub>4</sub>H]] + [[water|H<sub>2</sub>O]] → CH<sub>3</sub>CH<sub>2</sub>OH + [[sulfuric acid|H<sub>2</sub>SO<sub>4</sub>]] === Fermentation === {{details|Ethanol fermentation}} Ethanol for use in [[alcoholic beverage]]s, and the vast majority of ethanol for use as fuel, is produced by fermentation. When certain species of [[yeast]], most importantly, ''[[Saccharomyces cerevisiae]]'', [[metabolism|metabolize]] [[polysaccharide|sugar]] in the absence of [[oxygen]], they produce ethanol and [[carbon dioxide]]. The chemical equation below summarizes the conversion: : [[glucose|C<sub>6</sub>H<sub>12</sub>O<sub>6</sub>]] → 2 CH<sub>3</sub>CH<sub>2</sub>OH + 2 [[carbon dioxide|CO<sub>2</sub>]] The process of culturing yeast under conditions to produce alcohol is called [[fermentation]]. 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.<ref name="mosttolerant">Morais, P.B.; Rosa, C.A.; Linardi, V.R.; Carazza, F.; Nonato, E.A. "[http://www.springerlink.com/content/h32k825756g41318/ Production of fuel alcohol by Saccharomyces strains from tropical habitats]." ''Biotechnology Letters.'' November 1996. Vol. 18, No. 11, 1351–1356. Retrieved on [[September 2]], [[2007]].</ref> The fermentation process must exclude oxygen. If oxygen is present, yeast undergo [[aerobic respiration]] which produces [[carbon dioxide]] and water rather than ethanol. In order to produce ethanol from starchy materials such as [[cereal grain]]s, 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 [[mashing|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, [[fungi|fungally]] produced amylase, or some combination of the two.<ref name="hydrolysis">Badger, P.C. "[http://www.hort.purdue.edu/newcrop/ncnu02/v5-017.html Ethanol From Cellulose: A General Review]." p. 17–21. In: J. Janick and A. Whipkey (eds.), Trends in new crops and new uses. ASHS Press, 2002, Alexandria, VA. Retrieved on [[September 2]], [[2007]].</ref> ===Cellulosic ethanol=== {{main|Cellulosic ethanol}} Sugars for [[ethanol fermentation]] can be obtained from [[cellulose]].<ref>Taherzadeh M.J., Karimi K. (2007): Acid-based hydrolysis processes for ethanol from lignocellulosic materials: A review, BioResources, 2(3): 472-499</ref><ref>Taherzadeh M.J., Karimi K. (2007): Enzymatic-based hydrolysis processes for ethanol from lignocellulosic materials: A review, BioResources, 2(4): 707-738</ref> Until recently, however, the cost of the [[cellulase]] enzymes capable of hydrolyzing cellulose has been prohibitive. The [[Canada|Canadian]] firm [[Iogen Corp.|Iogen]] brought the first cellulose-based ethanol plant on-stream in 2004.<ref name="Ritter">Ritter, S.K. ([[May 31]] [[2004]]). "Biomass or Bust." ''Chemical & Engineering News'' '''82'''(22), 31–34.</ref> 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 [[corncob]]s, [[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.<ref>{{cite web | author = Clines, Tom | title = Brew Better Ethanol | publisher = Popular Science Online | date = July 2006 | url = http://www.popsci.com/popsci/energy/6756226d360ab010vgnvcm1000004eecbccdrcrd.html}}</ref> Cellulose-bearing materials typically also contain other [[polysaccharide]]s, including [[hemicellulose]]. When [[hydrolysis|hydrolyzed]], 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 [[pentose]]s into ethanol.<!--<ref>{{cite web|url=http://www.lub.lu.se/cgi-bin/show_diss.pl?db=global&fname=tec_748.html|title=www.lub.lu.se/cgi-bin/show_diss.pl?db=global&fname=tec_748.html}}</ref> --><ref>{{cite web|url=http://www.metabolicengineering.gov/me2001/2001Kompala.pdf|title=Maximizing Ethanol Production by Engineered Pentose-Fermenting ''Zymononas mobilis''|author=Dhinakar S. Kompala|publisher=Department of Chemical Engineering, University of Colorado at Boulder|accessdaymonth=21 May|accessyear=2007}}</ref> 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. By 2011 a full-scale plant will come on line, capable of producing 50 to 100 million gallons of ethanol a year (200–400 [[megalitre|ML]]/[[year|a]]).<ref>{{cite web |author=Mick, Jason |title=Cellulosic Ethanol Promises $1 per Gallon Fuel From Waste |date=[[2008-01-14]] |work=DailyTech.com |url=http://www.dailytech.com/Cellulosic+Ethanol+Promises+1+per+Gallon+Fuel+From+Waste/article10320.htm |accessdate=2008-01-15 }}</ref> === Prospective technologies === [[Image:SDethnl1.jpg|thumb|left|Ethanol plant in [[Turner County, South Dakota]]]] The [[anaerobic bacteria|anaerobic bacterium]] ''[[Clostridium]] ljungdahlii'', recently discovered in commercial chicken wastes, can produce ethanol from single-carbon sources including [[synthesis gas]], a mixture of [[carbon monoxide]] and [[hydrogen]] that can be generated from the partial [[combustion]] of either [[fossil fuel]]s 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]].<ref>{{cite web|url=http://www.brienergy.com/|title=Providing for a Sustainable Energy Future|publisher=Bioengineering Resources, inc|accessdaymonth=21 May|accessyear=2007}}</ref> Another prospective technology is the closed-loop ethanol plant.<ref name="clAlc">{{cite journal|url=http://www.renewableenergyaccess.com/rea/news/story?id=46414|title= Closed-Loop Ethanol Plant to Start Production|date=November 2, 2006|publisher=www.renewableenergyaccess.com|accessdate=2007-09-03}}</ref> 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, the energy for the distillation comes from fermented manure, produced from cattle that have been fed the by-products from the distillation. The leftover manure is then used to fertilize the soil used to grow the grain. Such a process is expected to have a much lower fossil fuel requirement.<ref name="Rapier-1">Rapier, R. ([[June 26]] [[2006]]) [http://i-r-squared.blogspot.com/2006/06/e3-biofuels-responsible-ethanol.html "E3 Biofuels: Responsible Ethanol"] R-Squared Energy Blog</ref> 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.<ref>{{cite web|url=http://www.truthout.org/issues_06/041607ED.shtml|title=Air Pollution Rules Relaxed for US Ethanol Producers|publisher=Truthout|date=2007-04-12|accessdaymonth=21 May|accessyear=2007}}</ref> ===Testing=== [[Image:Ethanol near IR spectrum.png|thumb|right|240px|[[Near infrared spectrum]] of liquid ethanol.]] Breweries and [[biofuel]] plants employ two methods for measuring ethanol concentration. Infrared ethanol sensors measure the vibrational frequency of dissolved ethanol using the CH band at 2900 cm<sup>−1</sup>. This method uses a relatively inexpensive solid state sensor that compares the CH band with a reference band to calculate the ethanol content. The calculation makes use of the [[Beer-Lambert law]]. Alternatively, by measuring the density of the starting material and the density of the product, using a [[hydrometer]], the change in specific gravity during fermentation indicates the alcohol content. This inexpensive and indirect method has a long history in the beer brewing industry. === Purification === {{main|Ethanol purification}} Ethylene hydration or brewing produces an ethanol–water mixture. For most industrial and fuel uses, the ethanol must be purified. [[Fractional distillation]] can concentrate ethanol to 95.6% by weight (89.5 mole%). This mixture is an [[azeotrope]] with a boiling point of 78.1 °C, and cannot be further purified by distillation. In one common industrial 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).<ref name="m_and_b">{{cite book|author=Morrison, Robert Thornton; Boyd, Robert Neilson|title=Organic Chemistry, 2nd ed.|year=1972|publisher=Allyn and Bacon, inc.}}</ref> 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]].<ref>{{cite journal |author=Snyder R, Kalf GF |title=A perspective on benzene leukemogenesis |journal=Crit. Rev. Toxicol. |volume=24 |issue=3 |pages=177–209 |year=1994 |pmid=7945890 |doi=10.3109/10408449409021605}}</ref> There is also an absolute alcohol production process by [[desiccation]] using [[glycerol]]. Alcohol produced by this method is known as spectroscopic alcohol — so called because the absence of benzene makes it suitable as a solvent in [[spectroscopy]]. Other methods for obtaining absolute ethanol include desiccation using adsorbents such as starch or [[zeolite]]s, which adsorb water preferentially, as well as [[azeotropic distillation]] and [[extractive distillation]].<br clear="all"> ==Grades of ethanol== === Denatured alcohol === {{Main|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.''<ref>{{cite web|url=http://www.procurement.umich.edu/Contracts/Denatured_Alchohol.pdf|title=U-M Program to Reduce the Consumption of Tax-free Alcohol; Denatured Alcohol a Safer, Less Expensive Alternative|publisher=University of Michigan|accessdate=2007-09-29}}</ref><ref>Great Britain (2005). ''[http://www.opsi.gov.uk/si/si2005/20051524.htm The Denatured Alcohol Regulations 2005].'' Statutory Instrument 2005 No. 1524. </ref> ===Absolute ethanol=== Absolute or anhydrous alcohol generally refers to purified ethanol, containing no more than one percent [[water]]. Absolute alcohol not intended for human consumption often contains trace amounts of toxic benzene (used to remove water by azeotropic distillation). Generally this kind of ethanol is used as solvents for lab and industrial settings where water will disrupt a desired reaction. Pure ethanol is classed as 200 [[Proof (alcohol)|proof]] in the USA, equivalent to 175 degrees proof in the UK system. == Use == === As a fuel=== {| class="wikitable" style="float:right; margin-left:1em" !colspan="4"|Volumetric [[energy density]] of some fuels compared with ethanol:<ref name=TEDB>[http://www-cta.ornl.gov/data/Appendix_B.html Appendix B, Transportation Energy Data Book] from the [[Center for Transportation Analysis]] of the [[Oak Ridge National Laboratory]]</ref><br> |- ! align = "left"|Fuel type ! align ="right"|&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;MJ/L ! align ="right"|&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;MJ/kg ! align ="right"|[[octane rating|Research<br>octane<br>number]] |- |[[ethanol fuel|Ethanol]] | align ="right"|23.5 | align ="right"|31.1<ref>Calculated from heats of formation. Does not correspond exactly to the figure for MJ/l divided by density.</ref> | align ="right"|129 |- | [[Methanol]] | align ="right"|17.9 | align ="right"|19.9 | align ="right"|123 |- | Regular Gasoline | align ="right"|34.8 | align ="right"|44.4<ref>[http://www.eere.energy.gov/hydrogenandfuelcells/pdfs/storage.pdf|Thomas, George. Overview of Storage Development DOE Hydrogen Program [pdf]. Livermore, CA. Sandia National Laboratories. 2000.]</ref> | align ="right"|Min 91 |- | Premium Gasoline | align ="right"| | align ="right"| | align ="right"|Min 95 |- | [[Aviation gasoline]]<br>(high octane gasoline, not Jet fuel) | align ="right"|33.5 | align ="right"|46.8 | align ="right"| |- | [[Alcohol fuel|Gasohol]]<br>(90% gasoline + 10% ethanol) | align ="right"|33.7 | align ="right"| | align ="right"|93/94 |- | [[Autogas]] ([[Liquified petroleum gas|LPG]])<br>(60% [[Propane]] + 40% [[Butane]]) | align ="right"|26.8 | align ="right"| | align ="right"| |- | [[Liquefied natural gas]] | align ="right"|25.3 | align ="right"|~55 | align ="right"| |- | [[Diesel]] | align ="right"|38.60 | align ="right"|45.41 | align ="right"|25 |}{{main|Ethanol fuel}} The largest single use of ethanol is as a motor [[fuel]] and [[fuel additive]]. The largest national fuel ethanol industries exist in [[Brazil]] (gasoline sold in Brazil contains at least 25% ethanol and anhydrous ethanol is also used as fuel in more than 90% of new cars sold in the country). The Brazilian production of ethanol is praised for the high [[carbon sequestration]] capabilities of the [[sugar cane]] [[plantations]], thus making it a real option to combat [[climate change]].<ref name="WaPo-Brazil">Reel, M. ([[August 19]] [[2006]]) [http://www.washingtonpost.com/wp-dyn/content/article/2006/08/19/AR2006081900842.html "Brazil's Road to Energy Independence"], ''[[Washington Post]]''.</ref> [[Henry Ford]] designed the first mass-produced automobile, the famed Model T Ford, to run on pure anhydrous (ethanol) alcohol—he said it was "the fuel of the future". Today, however, 100% pure ethanol is not approved as a motor vehicle fuel in the U.S. Added to gasoline, ethanol reduces ground-level ozone formation by lowering volatile organic compound and hydrocarbon emissions, decreasing carcinogenic benzene, and butadiene, emissions, and particulate matter emissions from gasoline combustion.<ref>{{cite web|url=http://journeytoforever.org/ethanol.html#E|title=Etnanol Fuel}}</ref> Prior to the development of [[electronic fuel injection]] (EFI) and computerized engine management, the lower energy content of ethanol required that the engine [[carburetor]] be ''rejetted'' to permit a larger volume of fuel to mix with the intake air. EFI is able to actively compensate for varying fuel energy densities by [[oxygen sensor| monitoring the oxygen content]] of exhaust gases. However, a standard EFI gasoline engine can typically only tolerate up to 10% ethanol and 90% gasoline. Higher ethanol ratios require either larger-volume [[fuel injector]]s or an increase in [[fuel rail]] pressure to deliver the greater liquid volume needed to equal the energy content of pure gasoline. [[Image:Sao Paulo ethanol pump 04 2008 74 zoom.jpg|thumb|left|Ethanol pump station in [[Sao Paulo, Brazil]] where the fuel is available commercially.]] World production of ethanol in 2006 was {{convert|51|GL|usgal}}, with 69% of the world supply coming from Brazil and the United States.<ref>{{cite web|url=http://www.ethanolrfa.org/industry/statistics/#E|title=Renewable Fuels Association Industry Statistics}}</ref> More than 20% of the Brazilian fleet of cars on the streets are able to use 100% ethanol as fuel, which includes ethanol-only engines and [[Flexible-fuel vehicle|flex-fuel]] engines.<ref>{{cite web|url=http://www.estadao.com.br/economia/not_eco178105,0.htm|title=Tecnologia flex atrai estrangeiros|Publisher=Agência Estado}}</ref> 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. Brazil supports this population of ethanol-burning automobiles with large national infrastructure that produces ethanol from domestically grown [[sugar cane]]. [[Sugar cane]] not only has a greater concentration of sucrose than corn (by about 30%), but is also much easier to extract. The [[bagasse]] generated by the process is not wasted, but is utilized in power plants as a surprisingly efficient fuel to produce electricity. [[Image:Ethanol Car.jpg|thumb|right|A [[Ford Taurus]] "fueled by clean burning ethanol" owned by [[New York City]].]] [[Image:USPS-E85 fuel-St Paul-20070127.jpg|thumb|right|[[United States Postal Service]] vehicle running on [[E85]], a "flex-fuel" blend in [[Saint Paul, Minnesota]].]] The United States fuel ethanol industry is based largely on [[Maize|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.<ref name="rfa1">{{cite web|url=http://www.ethanolrfa.org/media/press/rfa/view.php?id=909|title=First Commercial U.S. Cellulosic Ethanol Biorefinery Announced|date=2006-11-20|publisher=Renewable Fuels Association|accessdaymonth=21 May|accessyear=2006}}</ref> The [[Energy Policy Act of 2005]] requires that 4 billion gallons of "renewable fuel" be used in 2006 and this requirement will grow to a yearly production of 7.5 billion gallons by 2012.<ref name="epa1">{{cite web|url=http://www.epa.gov/otaq/renewablefuels/|title= Renewable Fuel Standard Program|publisher=United States Environmental Protection Agency|date=2007-04-10|accessdaymonth=21 May|accessyear=2007}}</ref> In the United States, ethanol is most commonly blended with gasoline as a 10% ethanol blend nicknamed "gasohol". This blend is widely sold throughout the U.S. [[Midwest]], and in cities required by the [[1990 Clean Air Act]] to oxygenate their gasoline during the winter.{{citation}} Ethanol and [[isobutene]] are also the feedstocks for [[ethyl tert-butyl ether]] (ETBE), an oxygenate antiknock additive. The use of ethanol makes ETBE partially a biofuel, but also more expensive than the similar additive [[methyl tert-butyl ether]] (MTBE), made from [[methanol]] and isobutene.{{citation}} ==== Food versus fuel debate ==== {{further|[[Food vs fuel]]}} It is disputed whether [[corn ethanol]] as an automotive fuel results in a net energy gain or loss. As reported in "The Energy Balance of Corn Ethanol: an Update,"<ref>{{cite web|url=http://www.transportation.anl.gov/pdfs/AF/265.pdf|title=The Energy Balance of Corn Ethanol: an Update|publisher=United States Department of Agriculture|accessdaymonth=21 May|accessyear=2007|author=Hosein Shapouri, James A. Duffield, and Michael Wang}}</ref> the energy returned on energy invested ([[EROEI]]) for ethanol made from corn in the U.S. is 1.34 (it yields 34% more energy than it takes to produce it). Input energy includes natural gas based fertilizers, farm equipment, transformation from corn or other materials, and transportation. However, other researchers report that the production of ethanol consumes more energy than it yields.<ref name=Pimentel2005>{{cite journal |author = Pimentel D, Patzek TW |year = 2005 |title = Ethanol Production Using Corn, Switchgrass, and Wood; Biodiesel Production Using Soybean and Sunflower |journal = Natural Resources Research |volume = 14 |issue = 1 |pages = 65–76 |doi = 10.1007/s11053-005-4679-8}}</ref><ref>{{cite web|url=http://www.news.cornell.edu/stories/July05/ethanol.toocostly.ssl.html|title=Cornell ecologist's study finds that producing ethanol and biodiesel from corn and other crops is not worth the energy|publisher=Cornell University|accessdaymonth=5 July|accessyear=2005|author=Lang, Susan S.}}</ref> In comparison, sugar cane ethanol EROEI is at around 8 (it yields 8 joules for each joule used to produce it).{{Fact|date=April 2008}} Recent research suggests that cellulosic crops such as [[switchgrass]] provide a much better net energy production than corn, producing over five times as much energy as the total used to produce the crop and convert it to fuel.<ref>{{cite web|url=http://www.pnas.org/cgi/reprint/0704767105v1 |title=Net energy of cellulosic ethanol from switchgrass|author=M.R. Schmer, K.P. Vogel, R.B. Mitchell, R.K. Perrin|publisher=U.S. Dept. of Agrigulture|date=2007-11-21|accessdate=2008-01-13}}</ref> If this research is confirmed, cellulosic crops will most likely displace corn as the main fuel crop for producing bioethanol. Michael Grunwald reports that one person could be fed 365 days "on the corn needed to fill an ethanol-fueled SUV".<ref>''The Clean Energy Scam'', '''TIME''', April 7, 2008, pages 40–41. </ref> He further reports that though "hyped as an eco-friendly fuel, ethanol increases global warming, destroys forests and inflates food prices." Environmentalists, livestock farmers, and opponents of subsidies say that increased ethanol production won't meet energy goals and may damage the environment, while at the same time causing worldwide food prices to soar. Some of the controversial subsidies in the past have included more than $10 billion to [[Archer-Daniels-Midland]] since 1980.<ref>{{cite web|url=http://www.cato.org/pub_display.php?pub_id=6079|title=Ethanol Keeps ADM Drunk On Tax Dollars.|publisher=CATO Institute|author=Doug Bandow|date=1997-10-02|accessdate=2007-09-03}}</ref>{{POV-statement|date=April 2008}}<!-- Why is this subsidy controversial? Don't a lot of farming-related operations get such subsidies? --> Critics also speculate that as ethanol is more widely used, changing irrigation practices could greatly increase pressure on water resources. In October 2007, 28 environmental groups decried the Renewable Fuels Standard (RFS), a legislative effort intended to increase ethanol production, and said that the measure will "lead to substantial environmental damage and a system of biofuels production that will not benefit family farmers...will not promote sustainable agriculture and will not mitigate global climate change."<ref name=csm>[http://www.csmonitor.com/2007/1115/p02s02-uspo.html The Politics of Ethanol Outshine its Costs]</ref><ref name="bw0307">{{cite journal|journal=Business Week|title=Ethanol's Growing List of Enemies|url=http://www.businessweek.com/bwdaily/dnflash/content/mar2007/db20070316_016207.htm?campaign_id=rss_topStories|date=March 19, 2007|accessdate=2007-09-03|author=Moira Herbst}}</ref> Recent articles have also blamed subsidized ethanol production for the nearly 200% increase in milk prices since 2004,<ref name="cnn0607">{{cite journal|journal=CNNMoney.com|title=Corn and milk: A 1-2 inflation combo|url=http://money.cnn.com/2007/06/19/news/economy/commodity_prices/index.htm|date=June 19, 2007|accessdate=2007-09-03|author=Jeff Cox}}</ref> although that is disputed by some{{Fact|date=March 2008}}. Especially since the price of fuel has driven up the costs to cultivate, grow, harvest, ship, refine, bring to market, etc, all commodities including; but not limited to, milk. Not to mention the presence of speculators, and the recent growing interest in the commodities market by investors who have been scared away from a falling stock market. Ethanol production uses the starch portion of corn, but the leftover protein can be used to create a high-nutrient, low-cost animal feed.<ref>[http://www.npr.org/templates/story/story.php?storyId=89598524 Fuel, Food Demand Raise Corn, Soybean Prices]</ref> In 2007 the United Nations' independent expert on the right to food, called for a five-year moratorium on biofuel production from food crops, to allow time for development of non-food sources. He called recent increases in food costs because of fuel production, such as the quadrupling of world corn price in one year, a growing "catastrophe" for the poor.<ref>{{cite news | url = http://www.livescience.com/environment/071027-ap-biofuel-crime.html | title=UN Expert Calls Biofuel 'Crime Against Humanity' | author = Edith M. Lederer, Associated Press | date = 2007-10-27 }}</ref> In February 2007, [[2007–2008 world food price crisis|riots]] occurred in Mexico because of the skyrocketing price of tortillas. Ethanol has been credited as the reason for this increase in food prices<ref>http://news.bbc.co.uk/2/hi/americas/6319093.stm</ref>. The demand for corn has had a rippling effect on many corn-based products, like tortillas. The effects of ethanol and the increasing cost of food have also been felt in Pakistan, Indonesia, and Egypt.<ref>{{cite web|url=http://www.openmarket.org/2008/04/08/ethanol-subsidies-cause-food-riots-in-mexico-pakistan-indonesia-yemen-and-egypt|title=Ethanol Subsidies Cause Food Riots in Mexico, Pakistan, Indonesia, Yemen, and Egypt|author=Posted by Hans Bader|publisher=Open Market blog|date=2008-04-08}}</ref> Oil has historically had a much higher [[EROEI]] than corn produced ethanol, according to some{{Fact|date=March 2008}}. However, oil must be refined into gasoline before it can be used for automobile fuel. Refining, as well as exploration and drilling, consumes energy. The difference between the energy in the fuel (output energy) and the energy needed to produce it (input energy) is often expressed as a percent of the input energy and called net energy gain (or loss). Several studies released in 2002 estimated that the net energy gain for [[corn ethanol]] is between 21 and 34 percent. The net energy loss for [[MTBE]] is about 33 percent. When added to gasoline, ethanol can replace MTBE as an anti-knock agent without poisoning drinking water as MTBE does. In Brazil, where the broadest and longest ethanol producing experiment took place, improvements in agricultural practices and ethanol production improvements led to an increase in ethanol net energy gain from 300% to over 800% in recent years.{{Fact|date=May 2008}} Consuming known oil reserves is increasing oil exploration and drilling energy consumption which is reducing [[EROEI|oil EROEI]] (and [[energy balance]]) further.<ref>{{cite web|url=http://oregon.gov/ENERGY/RENEW/Biomass/forum.shtml|title=Ethanol Energy Balances|author=David Andress & Associates|date=November, 2002}}</ref> Opponents claim that corn ethanol production does not result in a net energy gain or that the consequences of large scale ethanol production to the food industry and environment offset any potential gains from ethanol. It has been estimated that "if every bushel of U.S. [[corn]], [[wheat]], [[rice]] and [[soybean]] were used to produce ethanol, it would only cover about 4% of [[Energy policy of the United States|U.S. energy needs]] on a net basis."<ref>{{cite news|url=http://www.bloomberg.com/apps/news?pid=20601039&refer=columnist_wasik&sid=aOS8e5kvDESE|title=Forget the Ethanol Myth -- Avoid Biofuel Bubble: John F. Wasik|date=2007-07-23|publisher=Bloomberg.com|accessdate=2007-07-25}}</ref> Many of the issues raised could likely be fixed by techniques now in development that produce ethanol from agricultural waste, such as paper waste, switchgrass, and [[Energy crop|other materials]], but EIA Forecasts Significant Shortfall in Cellulosic Biofuel Production Compared to Target Set by Renewable Fuel Standard.<ref>{{cite web|url=http://www.greencarcongress.com/cellulosic_ethanol/index.html|title=Study Finds Net Energy of Cellulosic Ethanol from Switchgrass Much Higher Than Expected|date=2008-01-07|publisher=Green Car Congress|accessdate=2008-01-13}}</ref> Proponents cite the potential gains to the U.S. economy both from domestic fuel production and increased demand for corn. Optimistic calculations project that the United States is capable of producing enough ethanol to completely replace gasoline consumption.{{Fact|date=April 2008}} In comparison, Brazil's ethanol consumption today covers more than 50% of all energy used by vehicles in that country. In the [[United States]], preferential regulatory and tax treatment of ethanol automotive fuels introduces complexities beyond its energy economics alone. North American automakers have in 2006 and 2007 promoted a blend of 85% ethanol and 15% gasoline, marketed as [[E85]], and their [[Flexible-fuel vehicle|flex-fuel vehicles]], ''e.g.'' [[General Motors|GM's]] "[http://www.livegreengoyellow.com/ Live Green, Go Yellow]" campaign.<ref name="autochannel">{{cite web|title=GM Announces E85 Fuel Card Promotion On FlexFuel Vehicles|url=http://www.theautochannel.com/news/2006/05/02/005502.html|accessdate=2007-09-04|publisher=The Auto Channel}}</ref> The apparent motivation is the nature of U.S. [[CAFE|Corporate Average Fuel Economy (CAFE)]] standards, which give an effective 54% fuel efficiency bonus to vehicles capable of running on 85% alcohol blends over vehicles not adapted to run on 85% alcohol blends.<ref>{{cite web | title = CAFE Credits for Flex Fuel Vehicles Undermine Improvements in Fuel Economy | publisher = Public Citizen | date = [[2006-09-27]] | url =http://www.citizen.org/autosafety/vehicles/enviro/articles.cfm?ID=15763| accessdate = 2007-09-03}}</ref> In addition to this auto manufacturer-driven impetus for 85% alcohol blends, the [[United States Environmental Protection Agency]] had authority to mandate that minimum proportions of oxygenates be added to automotive gasoline on regional and seasonal bases from 1992 until 2006 in an attempt to reduce air pollution, in particular [[ground-level ozone]] and [[smog]].<ref "epars">{{cite web|url=http://www.epa.gov/otaq/rfg_regs.htm|title= Regulations & Standards|publisher=United States Environmental Protection Agency|accessdate=2007-09-04}}</ref> In the [[United States]], incidents of methyl tert(iary)-butyl ether ([[MTBE]]) groundwater contamination have been recorded in the majority of the 50 states,<ref>{{cite web|url=http://www.gao.gov/new.items/d02753t.pdf|title=MTBE Contamination from Underground Storage Tanks|publisher=United States General Accounting Office|date=2002-05-21|accessdate=2007-10-09}}</ref> and the State of [[California]]'s ban on the use of MTBE as a gasoline additive has further driven the more widespread use of ethanol as the most common fuel oxygenate.<ref name="epamtbe">{{cite web|url=http://www.epa.gov/mtbe/faq.htm|title=Methyl Tertiary Butyl Ether (MTBE)|publisher=United State Environmental Protection Agency|accessdate=2007-09-04}}</ref> A [[February 7]], 2008 [[Associated Press]] article stated, "The widespread use of ethanol from corn could result in nearly twice the greenhouse gas emissions as the gasoline it would replace because of expected land-use changes, researchers concluded Thursday. The study challenges the rush to biofuels as a response to global warming."<ref>[http://www.guardian.co.uk/worldlatest/story/0,,-7291645,00.html Study: Ethanol May Add to Global Warming] Associated Press, February 7, 2008</ref> One acre of land can yield about 7,110 pounds (3,225 kg) of corn, which can be processed into 328 gallons (1240.61 liters) of ethanol. That is about 26.1 pounds (11.84 kg) of corn per gallon. Much overlooked in most discussions about ethanol from corn are the by-products from the production of ethanol. Depending on the way it is processed, the processing yields several beneficial products, some of which are used for food production and feedstocks. ===Ethanol Fuel Cells=== {{main|Direct-ethanol fuel cell}} Ethanol may be used as a fuel to power [[Direct-ethanol fuel cell]]s ([[Direct-ethanol fuel cell|DEFC]]) in order to produce electricity and the by-products of [[water]] ([[H20|H<sub>2</sub>O]]) and [[carbon dioxide]] ([[carbon dioxide|CO<sub>2</sub>]]).<ref name="DEFC-chem">[http://www.fctec.com/fctec_types_dmfc.asp Direct Methanol Fuel Cells (DMFC)] FCTec.</ref> [[Platinum]] is commonly used as an [[anode]] in such fuel cells in order to achieve a [[power density]] that is comparable to competing technologies. Until recently the high price of platinum has been cost prohibitive. A company called [http://www.acta-nanotech.com Acta Nanotech] has created platinum free [[nanostructure]]d [[anode]]s using more common and therefore less expensive metals.<ref name="Acta-car">[http://www.acta-nanotech.com/index.php?option=com_content&task=view&id=131&Itemid=66 Offenburg students test world's first ethanol powered fuel cell vehicle] Acta.</ref> A vehicle using a [[Direct-ethanol fuel cell|DEFC]] and non-platinum nanostructured anodes was used in the [[Royal Dutch Shell|Shell]] [[Eco-Marathon]] 2007 by a team from [[Offenburg]] [[Germany]] which achieved an efficiency of 2716 [[kilometers per liter]] (6388 [[miles per gallon]]).<ref name="Offenburg-team">[http://www.schluckspecht.net Willkommen beim Projekt "Schluckspecht" der Hochschule Offenburg] .</ref> ===Rocket fuel=== Ethanol was commonly used as fuel in early [[bipropellant]] [[rocket]] 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 water to reduce the combustion chamber temperature.<ref>{{cite web|url=http://www.daviddarling.info/encyclopedia/V/V-2.html|title=The Internet Encyclopedia of Science: V-2|author=David Darling}}</ref><ref name="braeunig">Braeunig, Robert A. [http://www.braeunig.us/space/propel.htm "Rocket Propellants."] (Website). Rocket & Space Technology, 2006. Retrieved on [[2007]]-[[08-23]].</ref> The V-2's design team helped develop U.S. rockets following World War II, including the ethanol-fueled [[Redstone (rocket)|Redstone rocket]], which launched the first U.S. satellite.<ref>[http://science.ksc.nasa.gov/history/rocket-history.txt "A Brief History of Rocketry."] NASA Historical Archive, via science.ksc.nasa.gov.</ref> Alcohols fell into general disuse as more efficient rocket fuels were developed.<ref name="braeunig" /> === Alcoholic beverages === {{main|Alcoholic beverage}} Ethanol is the principal psychoactive constituent in [[alcoholic beverage]]s, with [[depressant]] effects to the [[central nervous system]]. It has a complex mode of action and affects multiple systems in the brain, most notably ethanol acts as an agonist to the [[GABA receptors]].<ref>{{cite journal |author=Chastain G |title=Alcohol, neurotransmitter systems, and behavior |journal=The Journal of general psychology |volume=133 |issue=4 |pages=329–35 |year=2006 |pmid=17128954 |doi=10.3200/GENP.133.4.329-335}}</ref> Similar psychoactives include those which also interact with [[GABA receptors]], such as [[gamma-hydroxybutyric acid]] (GHB).<ref name="boggan2"/> Ethanol is metabolized by the body as an energy-providing carbohydrate nutrient, as it metabolizes into [[acetyl CoA]], an intermediate common with [[glucose]] metabolism, that can be used for energy in the [[citric acid cycle]] or for biosynthesis. Alcoholic beverages vary considerably in their ethanol content and in the foodstuffs from which they are produced. Most alcoholic beverages can be broadly classified as [[fermented beverage]]s, beverages made by the action of yeast on sugary foodstuffs, or as [[distilled beverage]]s, 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 from which they are fermented. [[Beer]]s are made from [[cereal grain]]s or other [[starch]]y materials, [[wine]]s and [[cider]]s from [[fruit juice]]s, and [[mead]]s 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 [[whiskey]]s, distilled from fermented cereal grains; [[brandy|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 [[fruit]]s, [[herb]]s, and [[spice]]s 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 (beverage)|Applejack]] is traditionally made by [[freeze distillation]], by which water is frozen out of fermented [[apple cider]], leaving a more ethanol-rich liquid behind. [[Eisbier]] (more commonly, ''[[eisbock]]'') is also freeze-distilled, with [[beer]] as the base beverage. [[Fortified wine]]s 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 are not only 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. === Feedstock === {{main|Chemical derivatives of ethanol}} Ethanol is an important industrial ingredient and has widespread use as a base chemical for other organic compounds. These include ethyl [[halide]]s, ethyl [[ester]]s, [[diethyl ether]], [[acetic acid]], [[butadiene]], and ethyl [[amine]]s. === Antiseptic use === Ethanol is used in medical wipes and in most common antibacterial [[hand sanitizer]] gels at a concentration of about 62% ([[percentage]] by weight, not volume) as an [[antiseptic]]. Ethanol kills organisms by denaturing their [[protein]]s and dissolving their [[lipid]]s and is effective against most [[bacterium|bacteria]] and [[fungus|fungi]], and many [[virus]]es, but is ineffective against bacterial [[spore]]s.<ref>{{cite journal |author=McDonnell G, Russell AD |title=Antiseptics and disinfectants: activity, action, and resistance |journal=Clin. Microbiol. Rev. |volume=12 |issue=1 |pages=147–79 |year=1999 |pmid=9880479 |url=http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pubmed&pubmedid=9880479}}</ref> ===Antidote use=== Ethanol can be used as an antidote for poisoning by other toxic alcohols, in particular [[methanol]]<ref name="cambridge">{{cite web|url=http://www-clinpharm.medschl.cam.ac.uk/pages/teaching/topics/poison/poison9.html| title=Methanol Poisoning|publisher=Cambridge University School of Clinical Medicine|accessdate=2007-09-04}}</ref> and [[ethylene glycol]]. Ethanol [[competitive inhibition|competes]] with other alcohols for the [[alcohol dehydrogenase]] enzyme, preventing metabolism into toxic [[aldehyde]] and [[carboxylic acid]] derivatives.<ref>{{cite journal |author=Barceloux DG, Bond GR, Krenzelok EP, Cooper H, Vale JA |title=American Academy of Clinical Toxicology practice guidelines on the treatment of methanol poisoning |journal=J. Toxicol. Clin. Toxicol. |volume=40 |issue=4 |pages=415–46 |year=2002 |pmid=12216995 |doi=10.1081/CLT-120006745}}</ref> === Other uses === *Ethanol is easily [[miscible]] in [[water (molecule)|water]] and is a good [[solvent]]. Ethanol is less polar than water and used in [[perfume]]s, [[paint]]s and [[tincture]]s. *Ethanol is also used in design and sketch art markers, such as [[Copic]], and [[Tria]]. ==Effects on humans== {{Main|Short-term effects of alcohol}} The [[National Institute on Alcohol Abuse and Alcoholism]] maintains a database of alcohol-related health effects. <ref>{{cite web |url= http://etoh.niaaa.nih.gov/Archive.htm |title= ETOH Archival Database (1972–2003) |accessdate= 2008-03-31 |work= Alcohol and Alcohol Problems Science Database |publisher= [[National Institute on Alcohol Abuse and Alcoholism|NIAAA]]}}</ref> {| class="wikitable" style="float:right; width:25em; margin-left: 1em" ! BAC (mg/dL) !! Symptoms<ref name="Pohorecky & Brick">Pohorecky, L.A., and J. Brick. (1988). "Pharmacology of ethanol." ''Pharmacology & Therapeutics'' '''36'''(3), 335–427.</ref> |- | 50 || Euphoria, talkativeness, relaxation |- | 100 || Central nervous system depression, impaired motor and sensory function, impaired cognition |- | &gt; 140 || Decreased blood flow to brain |- | 300 || Stupefaction, possible unconsciousness |- | 400 || Possible death |- | &gt; 550 || Death |} ===Effects on the central nervous system=== Ethanol is a central nervous system depressant and has significant psychoactive effects in sublethal doses; for specifics, see [[Effects of alcohol on the body#Effects by dose|effects of alcohol on the body by dose]]. Based on its abilities to change the [[human consciousness]], ethanol is considered a [[drug]].<ref>[http://www.nlm.nih.gov/medlineplus/ency/article/001944.htm "Alcohol Use"] ''MedlinePlus Medical Encyclopedia'', U.S. National Library of Medicine and National Institutes of Health. Retrieved on [[2007]]-[[09-27]]</ref> Death from ethyl alcohol consumption is possible when blood alcohol level reaches 0.4%. A blood level of 0.5% or more is commonly fatal. Levels of even less than 0.1% can cause [[intoxication]], with unconsciousness often occurring at 0.3–0.4%.<ref name="yost"/> The amount of ethanol in the body is typically quantified by [[blood alcohol content]] (BAC), the [[milligram]]s of ethanol per 100 [[milliliter]]s of blood. The table at right summarizes the symptoms of ethanol consumption. Small doses of ethanol generally produce euphoria and relaxation; people experiencing these symptoms tend to become talkative and less inhibited, and may exhibit poor judgment. At higher dosages (BAC &gt; 100 mg/dl), 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. In America, about half of the deaths in car accidents occur in alcohol-related crashes.<ref>{{cite journal |author=Hingson R, Winter M |title=Epidemiology and consequences of drinking and driving |journal=Alcohol research & health : the journal of the National Institute on Alcohol Abuse and Alcoholism |volume=27 |issue=1 |pages=63–78 |year=2003 |pmid=15301401 |url=http://pubs.niaaa.nih.gov/publications/arh27-1/63-78.pdf}}</ref> There is no completely safe level of alcohol for driving; the risk of a fatal [[car accident]] rises with the level of alcohol in the driver's blood.<ref>{{cite journal |author=Naranjo CA, Bremner KE |title=Behavioural correlates of alcohol intoxication |journal=[[Addiction (journal)|Addiction]] |volume=88 |issue=1 |pages=25–35 |year=1993 |pmid=8448514 |doi=10.1111/j.1360-0443.1993.tb02761.x}}</ref> However, 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% to 0.08%. ===Effects on metabolism=== {{Main|Alcohol metabolism}} 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,<ref name="boggan1">{{cite web|url=http://chemcases.com/alcohol/alc-06.htm|accessdate=2007-09-29|author=Dr. Bill Boggan|title= Metabolism of Ethyl Alcohol in the Body|publisher=Chemases.com}}</ref> 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,<ref name="boggan2">{{cite web|url=http://chemcases.com/alcohol/alc-07.htm|accessdate=2007-09-29|author=Dr. Bill Boggan|title= Effects of Ethyl Alcohol on Organ Function|publisher=Chemases.com}}</ref> multiple forms of cancer, and alcoholism. ===Drug interactions=== Ethanol can interact in harmful ways with a number of other drugs, including [[barbiturate]]s, [[benzodiazepine]]s, [[opioid]]s, and [[phenothiazine]]s<ref name="yost">{{cite journal|url=http://www.postgradmed.com/issues/2002/12_02/yost1.htm|title=Acute care for alcohol intoxication|publisher=Postgraduate Medicine Online|author=David A. Yost, MD|volume=112|number=6|date=December 2002|accessdate=2007-09-29}}</ref> ===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. Conversely, those who have acquired ethanol [[drug tolerance|tolerance]] have a greater quantity of these enzymes, and metabolize ethanol more rapidly.<ref>{{cite journal |author=Agarwal DP, Goedde HW |title=Pharmacogenetics of alcohol metabolism and alcoholism |journal=Pharmacogenetics |volume=2 |issue=2 |pages=48–62 |year=1992 |pmid=1302043 |doi=10.1097/00008571-199204000-00002}}</ref> ===Other effects=== Frequent drinking of alcoholic beverages has been shown to be a major contributing factor in cases of elevated blood levels of [[triglycerides]].<ref>{{cite web|url=http://www.americanheart.org/presenter.jhtml?identifier=4778|title=Triglycerides |accessdate=2007-09-04|publisher=American Heart Association}}</ref> Ethanol is not a [[carcinogen]],<ref name="msdsbj">{{cite web|url=http://www.cise.columbia.edu/clean/msds/ethanol.pdf|title=Material Data Safety Sheet|publisher=Burdick and Jackson|accessdate=2007-10-25}}</ref><ref name=aacr>{{cite web|url=http://www.aacr.org/PDF_files/2004Prevention/Program/2004_Prevention_Abstracts.pdf|title=Animal Models for Carcinogenesis and Chemoprevention, abstract #C42: Effects of Chronic Ethanol Intake on Cyclin D1 Levels and Altered Foci in Diethylnitrosamine-initiated Rats|author=Pollyanna R. Chavez, Xiang-Dong Wang, Jean Meyer|publisher=USDA|accessdate=2007-10-24}}</ref> but its effect on the [[liver]] can contribute to [[immune suppression]]. Consequently, consumption of alcoholic beverages can be an aggravating factor in cancers. == See also == {{EnergyPortal}} {{col-begin}} {{col-break}} * [[1-propanol]] * [[2,2,2-trichloroethanol]] * [[Alcoholic beverage]] * [[Biobutanol]] * [[Biodiesel]] * [[Breathalyzer]] * [[Cellulosic ethanol]] * [[Cellulosic ethanol commercialization]] * [[Corn ethanol]] * [[Corn liquor]] {{col-break}} * [[Denatured alcohol]] * [[Ethanol (data page)]] * [[Ethanol fuel]] * [[Ethanol fuel in Brazil]] * [[Isopropyl alcohol]] * [[List of energy topics]] * [[Rubbing alcohol]] * [[Timeline of alcohol fuel]] {{col-end}} == References == {{reflist|2}} == Further reading == {{refbegin}} * "Alcohol." (1911). In Hugh Chisholm (Ed.) ''[[Encyclopædia Britannica Eleventh Edition]].'' [http://91.1911encyclopedia.org/A/AL/ALCOHOL.htm Online reprint] * Lodgsdon, J.E. (1994). "Ethanol." In J.I. Kroschwitz (Ed.) ''Encyclopedia of Chemical Technology, 4th ed.'' vol. 9, pp. 812–860. New York: John Wiley & Sons. * Smith, M.G., and M. Snyder. (2005). "Ethanol-induced virulence of ''Acinetobacter baumannii''". ''American Society for Microbiology meeting''. [[June 5]] – [[June 9]]. Atlanta. * [http://sci-toys.com/ingredients/alcohol.html Sci-toys website explanation of US denatured alcohol designations] * Boyce, John M., and Pittet Didier. (2003). [http://www.cdc.gov/handhygiene/ “Hand Hygiene in Healthcare Settings.”] [[Centers for Disease Control]], [[Atlanta, Georgia]], [[United States]]. * {{cite web|title= VS1000A Series In-Line Ethanol Sensors for the Beverage and BioFuel Industry|author=Rene Martinez VitalSensors Technologies LLC|url=http://www.vitalsensorstech.com/VitalSensors%20VS-1000A%20Ethanol%20Alcohol%20Sensor%20Data%20Sheet.pdf}} Martinez describes the theory and practice of measuring brix on-line in beverages. {{refend}} ==External links== *[http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc00/icsc0044.htm International Labour Organization] ethanol safety information *[http://www.npi.gov.au/database/substance-info/profiles/35.html National Pollutant Inventory – Ethanol Fact Sheet] *[http://www.ethanol-information.com/ Ethanol Information] *[http://www.theethanolsource.com/ Ethanol Facts] *[http://www.compchemwiki.org/index.php?title=Ethanol Coordinates of the ethanol molecule] on Computational Chemistry Wiki. Accessed on [[8 September]] [[2005]]. *[http://www.bluerhinos.co.uk/molview/indv.php?id=4 Molview from bluerhinos.co.uk] See Ethanol in 3D *[http://webbook.nist.gov/cgi/cbook.cgi?Name=ethanol&Units=SI National Institute of Standards and Technology] chemical data on ethanol *[http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16236 ChEBI – biology related] *[http://www.cbot.com/ Chicago Board of Trade] news and market data on ethanol futures {{Alcohols}} {{Antiseptics and disinfectants}} {{Antidotes}} [[Category:anatomical preservation]] [[Category:Alcohol]] [[Category:Alcohols]] [[Category:Anxiolytics]] [[Category:Drugs]] [[Category:Rocket fuels]] [[Category:Household chemicals]] [[Category:Alcohol solvents]] [[Category:Teratogens]] [[Category:Disinfectants]] [[Category:Oxygenates]] [[Category:straight-chain alcohols]] [[af:Etanol]] [[ar:الإثانول]] [[bn:ইথানল]] [[bs:Etanol]] [[bg:Етанол]] [[ca:Etanol]] [[cs:Ethanol]] [[da:Ætanol]] [[de:Ethanol]] [[et:Etanool]] [[el:Αιθανόλη]] [[es:Etanol]] [[eo:Etanolo]] [[eu:Etanol]] [[fa:اتانول]] [[fr:Éthanol]] [[gl:Etanol]] [[ko:에탄올]] [[hr:Etanol]] [[id:Etanol]] [[is:Etanól]] [[it:Etanolo]] [[he:אתנול]] [[la:Ethanol]] [[lv:Etanols]] [[lb:Ethanol]] [[lt:Etanolis]] [[hu:Etanol]] [[ms:Etanol]] [[nl:Ethanol]] [[ja:エタノール]] [[no:Etanol]] [[nn:Etanol]] [[pl:Alkohol etylowy]] [[pt:Etanol]] [[ro:Etanol]] [[qu:Ethanul]] [[ru:Этанол]] [[simple:Ethanol]] [[sk:Etanol]] [[sl:Etanol]] [[sh:Alkohol]] [[fi:Etanoli]] [[sv:Etanol]] [[ta:எத்தனால்]] [[th:เอทานอล]] [[vi:Êtanol]] [[tg:Итонул]] [[tr:Etanol]] [[uk:Етанол]] [[zh:乙醇]]