Ethanol - Wikipedia

OH (an ethyl group linked to a hydroxyl group), and is often abbreviated as EtOH. Ethanol is a volatile, flammable, colorless liquid with a characteristic wine- ... Ethanol FromWikipedia,thefreeencyclopedia Jumptonavigation Jumptosearch Organicchemicalcompound Forethanolasadrugormedicine,seeAlcohol(drug)andAlcohols(medicine). Nottobeconfusedwithethenol,alsoknownasvinylalcoholorethynol.Thisarticle'sleadsectionmaybetooshorttoadequatelysummarizethekeypoints.Pleaseconsiderexpandingtheleadtoprovideanaccessibleoverviewofallimportantaspectsofthearticle.(January2022) Ethanol Names Pronunciation /ˈɛθənɒl/ PreferredIUPACname Ethanol[1] Othernames absolutealcoholalcoholcolognespiritdrinkingalcoholethylicalcoholEtOHethylalcoholethylhydrateethylhydroxideethylolgrainalcoholhydroxyethanemethylcarbinol Identifiers CASNumber 64-17-5 Y 3Dmodel(JSmol) Interactiveimage 3DMet B01253 BeilsteinReference 1718733 ChEBI CHEBI:16236 Y ChEMBL ChEMBL545 Y ChemSpider 682 Y DrugBank DB00898 Y ECHAInfoCard 100.000.526 GmelinReference 787 IUPHAR/BPS 2299 PubChemCID 702 UNII 3K9958V90M Y UNnumber UN1170 CompToxDashboard(EPA) DTXSID9020584 InChI InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3 YKey: LFQSCWFLJHTTHZ-UHFFFAOYSA-N YInChI=1/C2H6O/c1-2-3/h3H,2H2,1H3Key: LFQSCWFLJHTTHZ-UHFFFAOYAB SMILES OCC Properties Chemicalformula C2H6O Molarmass 46.069 g·mol−1 Appearance Colourlessliquid Odor Methanol-like[2] Density 0.78945g/cm3(at20°C)[3] Meltingpoint −114.14 ± 0.03[3] °C(−173.45 ± 0.05 °F;159.01 ± 0.03 K) Boilingpoint 78.23 ± 0.09[3] °C(172.81 ± 0.16 °F;351.38 ± 0.09 K) Solubilityinwater Miscible logP −0.18 Vaporpressure 5.95kPa(at20 °C) Acidity(pKa) 15.9(H2O),29.8(DMSO)[4][5] Magneticsusceptibility(χ) −33.60·10−6cm3/mol Refractiveindex(nD) 1.3611[3] Viscosity 1.2mPa·s(at20 °C),1.074mPa·s(at25 °C)[6] Dipolemoment 1.69D[7] Hazards GHSlabelling: Pictograms Signalword Danger Hazardstatements H225,H319 Precautionarystatements P210,P280,P305+P351+P338 NFPA704(fire diamond) 2 3 0 Flashpoint 14°C(Absolute)[9] Lethaldoseorconcentration(LD,LC): LD50(mediandose) 7340 mg/kg(oral,rat)7300 mg/kg(mouse) NIOSH(UShealthexposurelimits): PEL(Permissible) TWA1000ppm(1900 mg/m3)[10] REL(Recommended) TWA1000ppm(1900 mg/m3)[10] IDLH(Immediatedanger) N.D.[10] Safetydatasheet(SDS) [8] Relatedcompounds Relatedcompounds EthaneMethanol Supplementarydatapage Ethanol(datapage) Exceptwhereotherwisenoted,dataaregivenformaterialsintheirstandardstate(at25 °C[77 °F],100 kPa). N verify (whatis YN ?) Infobox references Chemicalcompound Ethanol(alsocalledethylalcohol,grainalcohol,drinkingalcohol,orsimplyalcohol)isanorganicchemicalcompound.ItisasimplealcoholwiththechemicalformulaC2H6O.ItsformulacanbealsowrittenasCH3−CH2−OHorC2H5OH(anethylgrouplinkedtoahydroxylgroup),andisoftenabbreviatedasEtOH.Ethanolisavolatile,flammable,colorlessliquidwithacharacteristicwine-likeodorandpungenttaste.[11][12]Itisapsychoactivedrug,recreationaldrug,andtheactiveingredientinalcoholicdrinks. Ethanolisnaturallyproducedbythefermentationofsugarsbyyeastsorviapetrochemicalprocessessuchasethylenehydration.Ithasmedicalapplicationsasanantisepticanddisinfectant.Itisusedasachemicalsolventandinthesynthesisoforganiccompounds.Ethanolisafuelsource. Contents 1Etymology 2Uses 2.1Medical 2.1.1Antiseptic 2.1.2Antidote 2.1.3Medicinalsolvent 2.1.4Pharmacology 2.2Recreational 2.3Fuel 2.3.1Enginefuel 2.3.2Rocketfuel 2.3.3Fuelcells 2.3.4Householdheatingandcooking 2.4Feedstock 2.5Solvent 2.6Low-temperatureliquid 3Chemistry 3.1Chemicalformula 3.2Physicalproperties 3.3Solventproperties 3.4Flammability 4Naturaloccurrence 5Production 5.1Ethylenehydration 5.2FromCO2 5.3Fermentation 5.3.1Cellulose 5.4Testing 6Purification 6.1Distillation 6.2Molecularsievesanddesiccants 6.3Membranesandreverseosmosis 6.4Othertechniques 6.5Gradesofethanol 6.5.1Denaturedalcohol 6.5.2Absolutealcohol 6.5.3Rectifiedspirits 7Reactions 7.1Esterformation 7.2Dehydration 7.3Combustion 7.4Acid-basechemistry 7.5Halogenation 7.6Oxidation 7.7Metabolism 8Safety 9History 10Seealso 11References 12Furtherreading 13Externallinks Etymology[edit] EthanolisthesystematicnamedefinedbytheInternationalUnionofPureandAppliedChemistry(IUPAC)foracompoundconsistingofanalkylgroupwithtwocarbonatoms(prefix"eth-"),havingasinglebondbetweenthem(infix"-an-")andanattachedfunctionalgroup−OHgroup(suffix"-ol").[13] The"eth-"prefixandthequalifier"ethyl"in"ethylalcohol"originallycomefromthename"ethyl"assignedin1834tothegroupC2H5−byJustusLiebig.HecoinedthewordfromtheGermannameAetherofthecompoundC2H5−O−C2H5(commonlycalled"ether"inEnglish,morespecificallycalled"diethylether").[14]AccordingtotheOxfordEnglishDictionary,EthylisacontractionoftheAncientGreekαἰθήρ(aithḗr,"upperair")andtheGreekwordὕλη(hýlē,"substance").[15] ThenameethanolwascoinedasaresultofaresolutionthatwasadoptedattheInternationalConferenceonChemicalNomenclaturethatwasheldinApril1892inGeneva,Switzerland.[16] Theterm"alcohol"nowreferstoawiderclassofsubstancesinchemistrynomenclature,butincommonparlanceitremainsthenameofethanol.ItisamedievalloanfromArabical-kuḥl,apowderedoreofantimonyusedsinceantiquityasacosmetic,andretainedthatmeaninginMiddleLatin.[17]Theuseof"alcohol"forethanol(infull,"alcoholofwine")ismodernandwasfirstrecordedin1753.Beforethelate18thcenturytheterm"alcohol"generallyreferredtoanysublimatedsubstance.[18] Uses[edit] Medical[edit] Mainarticle:Alcohol(medicine) Antiseptic[edit] Ethanolisusedinmedicalwipesandmostcommonlyinantibacterialhandsanitizergelsasanantisepticforitsbactericidalandanti-fungaleffects.[19]Ethanolkillsmicroorganismsbydissolvingtheirmembranelipidbilayeranddenaturingtheirproteins,andiseffectiveagainstmostbacteria,fungiandviruses.However,itisineffectiveagainstbacterialspores,butthatcanbealleviatedbyusinghydrogenperoxide.[20]Asolutionof70%ethanolismoreeffectivethanpureethanolbecauseethanolreliesonwatermoleculesforoptimalantimicrobialactivity.Absoluteethanolmayinactivatemicrobeswithoutdestroyingthembecausethealcoholisunabletofullypermeatethemicrobe'smembrane.[21][22]Ethanolcanalsobeusedasadisinfectantandantisepticbecauseitcausescelldehydrationbydisruptingtheosmoticbalanceacrosscellmembrane,sowaterleavesthecellleadingtocelldeath.[23] Antidote[edit] Ethanolmaybeadministeredasanantidotetoethyleneglycolpoisoning[24]andmethanolpoisoning.[25] Medicinalsolvent[edit] Ethanol,ofteninhighconcentrations,isusedtodissolvemanywater-insolublemedicationsandrelatedcompounds.Liquidpreparationsofpainmedications,coughandcoldmedicines,andmouthwashes,forexample,maycontainupto25%ethanol[26]andmayneedtobeavoidedinindividualswithadversereactionstoethanolsuchasalcohol-inducedrespiratoryreactions.[27]Ethanolispresentmainlyasanantimicrobialpreservativeinover700liquidpreparationsofmedicineincludingacetaminophen,ironsupplements,ranitidine,furosemide,mannitol,phenobarbital,trimethoprim/sulfamethoxazoleandover-the-countercoughmedicine.[28] Pharmacology[edit] Inmammals,ethanolisprimarilymetabolizedintheliverandstomachbyalcoholdehydrogenase(ADH)enzymes.[29]Theseenzymescatalyzetheoxidationofethanolintoacetaldehyde(ethanal):[30] CH3CH2OH+NAD+→CH3CHO+NADH+H+ Whenpresentinsignificantconcentrations,thismetabolismofethanolisadditionallyaidedbythecytochromeP450enzymeCYP2E1inhumans,whiletraceamountsarealsometabolizedbycatalase.[31] Theresultingintermediate,acetaldehyde,isaknowncarcinogen,andposessignificantlygreatertoxicityinhumansthanethanolitself.Manyofthesymptomstypicallyassociatedwithalcoholintoxication—aswellasmanyofthehealthhazardstypicallyassociatedwiththelong-termconsumptionofethanol—canbeattributedtoacetaldehydetoxicityinhumans.[32] Thesubsequentoxidationofacetaldehydeintoacetateisperformedbyaldehydedehydrogenase(ALDH)enzymes.AmutationintheALDH2genethatencodesforaninactiveordysfunctionalformofthisenzymeaffectsroughly50%ofeastAsianpopulations,contributingtothecharacteristicalcoholflushreactionthatcancausetemporaryreddeningoftheskinaswellasanumberofrelated,andoftenunpleasant,symptomsofacetaldehydetoxicity.[33]ThismutationistypicallyaccompaniedbyanothermutationinthealcoholdehydrogenaseenzymeADH1Binroughly80%ofeastAsians,whichimprovesthecatalyticefficiencyofconvertingethanolintoacetaldehyde.[33] Recreational[edit] Mainarticles:Alcohol(drug)andAlcoholicdrink Asacentralnervoussystemdepressant,ethanolisoneofthemostcommonlyconsumedpsychoactivedrugs.[34] Despitealcohol'spsychoactiveandcarcinogenicproperties,itisreadilyavailableandlegalforsaleinmostcountries.However,therearelawsregulatingthesale,exportation/importation,taxation,manufacturing,consumption,andpossessionofalcoholicbeverages.Themostcommonregulationisprohibitionforminors. Fuel[edit] Enginefuel[edit] Mainarticle:Ethanolfuel Energycontent(lowerheatingvalue)ofsomefuelscomparedwithethanol.Higheroctaneequalslowerenergydensityandlesspowerpergivenquantityburned.[35] Fueltype MJ/L MJ/kg Researchoctanenumber Drywood(20%moisture) ~19.5 Methanol 17.9 19.9 108.7[36] Ethanol 21.2[37] 26.8[37] 108.6[36] E85(85%ethanol,15%gasoline) 25.2 33.2 105 Liquefiednaturalgas 25.3 ~55 Autogas(LPG)(60%propane+40%butane) 26.8 50 Aviationgasoline(high-octanegasoline,notjetfuel) 33.5 46.8 100/130(lean/rich) Gasohol(90%gasoline+10%ethanol) 33.7 47.1 93/94 Regulargasoline/petrol 34.8 44.4[38] min.91 Premiumgasoline/petrol max.104 Diesel 38.6 45.4 25 Charcoal,extruded 50 23 Thelargestsingleuseofethanolisasanenginefuelandfueladditive.Brazilinparticularreliesheavilyupontheuseofethanolasanenginefuel,dueinparttoitsroleasoneoftheglobe'sleadingproducersofethanol.[39][40]GasolinesoldinBrazilcontainsatleast25%anhydrousethanol.Hydrousethanol(about95%ethanoland5%water)canbeusedasfuelinmorethan90%ofnewgasolinefueledcarssoldinthecountry.Brazilianethanolisproducedfromsugarcane,whichhasrelativelyhighyields(830%morefuelthanthefossilfuelsusedtoproduceit)comparedtosomeotherenergycrops.[41]TheUSandmanyothercountriesprimarilyuseE10(10%ethanol,sometimesknownasgasohol)andE85(85%ethanol)ethanol/gasolinemixtures. USPgradeethanolforlaboratoryuse. Australianlawlimitstheuseofpureethanolfromsugarcanewasteto10%inautomobiles.Oldercars(andvintagecarsdesignedtouseaslowerburningfuel)shouldhavetheenginevalvesupgradedorreplaced.[42] Accordingtoanindustryadvocacygroup,ethanolasafuelreducesharmfultailpipeemissionsofcarbonmonoxide,particulatematter,oxidesofnitrogen,andotherozone-formingpollutants.[43]ArgonneNationalLaboratoryanalyzedgreenhousegasemissionsofmanydifferentengineandfuelcombinations,andfoundthatbiodiesel/petrodieselblend(B20)showedareductionof8%,conventionalE85ethanolblendareductionof17%andcellulosicethanol64%,comparedwithpuregasoline.[44]Ethanolhasamuchgreaterresearchoctanenumber(RON)thangasoline,meaningitislesspronetopre-ignition,allowingforbetterignitionadvancewhichmeansmoretorque,andefficiencyinadditiontothelowercarbonemissions.[45] Ethanolcombustioninaninternalcombustionengineyieldsmanyoftheproductsofincompletecombustionproducedbygasolineandsignificantlylargeramountsofformaldehydeandrelatedspeciessuchasacetaldehyde.[46]Thisleadstoasignificantlylargerphotochemicalreactivityandmoregroundlevelozone.[47]ThisdatahasbeenassembledintoTheCleanFuelsReportcomparisonoffuelemissions[48]andshowthatethanolexhaustgenerates2.14 timesasmuchozoneasgasolineexhaust.[49]WhenthisisaddedintothecustomLocalizedPollutionIndex(LPI)ofTheCleanFuelsReport,thelocalpollutionofethanol(pollutionthatcontributestosmog)israted1.7,wheregasolineis1.0andhighernumberssignifygreaterpollution.[50]TheCaliforniaAirResourcesBoardformalizedthisissuein2008byrecognizingcontrolstandardsforformaldehydesasanemissionscontrolgroup,muchliketheconventionalNOxandReactiveOrganicGases(ROGs).[51] Worldproductionofethanolin2006was51gigalitres(1.3×1010 US gal),with69%oftheworldsupplycomingfromBrazilandtheUnitedStates.[52]Morethan20%ofBraziliancarsareabletouse100%ethanolasfuel,whichincludesethanol-onlyenginesandflex-fuelengines.[53]Flex-fuelenginesinBrazilareabletoworkwithallethanol,allgasolineoranymixtureofboth.IntheUSflex-fuelvehiclescanrunon0%to85%ethanol(15%gasoline)sincehigherethanolblendsarenotyetallowedorefficient.Brazilsupportsthisfleetofethanol-burningautomobileswithlargenationalinfrastructurethatproducesethanolfromdomesticallygrownsugarcane.Sugarcanenotonlyhasagreaterconcentrationofsucrosethancorn(byabout30%),butisalsomucheasiertoextract.Thebagassegeneratedbytheprocessisnotwasted,butisusedinpowerplantstoproduceelectricity.[citationneeded] IntheUnitedStates,theethanolfuelindustryisbasedlargelyoncorn.AccordingtotheRenewableFuelsAssociation,asof30October2007,131grainethanolbio-refineriesintheUnitedStateshavethecapacitytoproduce7.0 billionUSgallons(26,000,000 m3)ofethanolperyear.Anadditional72constructionprojectsunderway(intheUS)canadd6.4 billionUSgallons(24,000,000 m3)ofnewcapacityinthenext18months.Overtime,itisbelievedthatamaterialportionofthe≈150-billion-US-gallon(570,000,000 m3)peryearmarketforgasolinewillbegintobereplacedwithfuelethanol.[54] Sweetsorghumisanotherpotentialsourceofethanol,andissuitableforgrowingindrylandconditions.TheInternationalCropsResearchInstitutefortheSemi-AridTropics(ICRISAT)isinvestigatingthepossibilityofgrowingsorghumasasourceoffuel,food,andanimalfeedinaridpartsofAsiaandAfrica.[55]Sweetsorghumhasone-thirdthewaterrequirementofsugarcaneoverthesametimeperiod.Italsorequiresabout22%lesswaterthancorn(alsoknownasmaize).Theworld'sfirstsweetsorghumethanoldistillerybegancommercialproductionin2007inAndhraPradesh,India.[56] Ethanol'shighmiscibilitywithwatermakesitunsuitableforshippingthroughmodernpipelineslikeliquidhydrocarbons.[57]Mechanicshaveseenincreasedcasesofdamagetosmallengines(inparticular,thecarburetor)andattributethedamagetotheincreasedwaterretentionbyethanolinfuel.[58] EthanolpumpstationinSãoPaulo,BrazilAFordTaurusfueledbyethanolinNewYorkCityUSPStruckrunningonE85inMinnesota Rocketfuel[edit] Ethanolwascommonlyusedasfuelinearlybipropellantrocket(liquid-propelled)vehicles,inconjunctionwithanoxidizersuchasliquidoxygen.TheGermanA-4ballisticrocketofWorldWarII,betterknownbyitspropagandanameV-2,[59]whichiscreditedashavingbegunthespaceage,usedethanolasthemainconstituentofB-Stoff.Undersuchnomenclature,theethanolwasmixedwith25%watertoreducethecombustionchambertemperature.[60][61]TheV-2'sdesignteamhelpeddevelopUSrocketsfollowingWorldWarII,includingtheethanol-fueledRedstonerocketwhichlaunchedthefirstUSsatellite.[62]Alcoholsfellintogeneraldisuseasmoreenergy-denserocketfuelsweredeveloped,[61]althoughethanoliscurrentlyusedinlightweightrocket-poweredracingaircraft.[63] Fuelcells[edit] Commercialfuelcellsoperateonreformednaturalgas,hydrogenormethanol.Ethanolisanattractivealternativeduetoitswideavailability,lowcost,highpurityandlowtoxicity.Thereisawiderangeoffuelcellconceptsthathaveenteredtrialsincludingdirect-ethanolfuelcells,auto-thermalreformingsystemsandthermallyintegratedsystems.Themajorityofworkisbeingconductedataresearchlevelalthoughthereareanumberoforganizationsatthebeginningofthecommercializationofethanolfuelcells.[64] Householdheatingandcooking[edit] Ethanolfireplacescanbeusedforhomeheatingorfordecoration.Ethanolcanalsobeusedasstovefuelforcooking.[65][66] Feedstock[edit] Furtherinformation:§ Reactions Ethanolisanimportantindustrialingredient.Ithaswidespreaduseasaprecursorforotherorganiccompoundssuchasethylhalides,ethylesters,diethylether,aceticacid,andethylamines. Solvent[edit] Ethanolisconsideredauniversalsolvent,asitsmolecularstructureallowsforthedissolvingofbothpolar,hydrophilicandnonpolar,hydrophobiccompounds.Asethanolalsohasalowboilingpoint,itiseasytoremovefromasolutionthathasbeenusedtodissolveothercompounds,makingitapopularextractingagentforbotanicaloils.Cannabisoilextractionmethodsoftenuseethanolasanextractionsolvent,[67]andalsoasapost-processingsolventtoremoveoils,waxes,andchlorophyllfromsolutioninaprocessknownaswinterization. Ethanolisfoundinpaints,tinctures,markers,andpersonalcareproductssuchasmouthwashes,perfumesanddeodorants.However,polysaccharidesprecipitatefromaqueoussolutioninthepresenceofalcohol,andethanolprecipitationisusedforthisreasoninthepurificationofDNAandRNA. Low-temperatureliquid[edit] Becauseofitslowfreezingpoint-173.20 °F(−114.14 °C)andlowtoxicity,ethanolissometimesusedinlaboratories(withdryiceorothercoolants)asacoolingbathtokeepvesselsattemperaturesbelowthefreezingpointofwater.Forthesamereason,itisalsousedastheactivefluidinalcoholthermometers. Chemistry[edit] Furtherinformation:Ethanol(datapage) Chemicalformula[edit] Ethanolisa2-carbonalcohol.ItsmolecularformulaisCH3CH2OH.AnalternativenotationisCH3−CH2−OH,whichindicatesthatthecarbonofamethylgroup(CH3−)isattachedtothecarbonofamethylenegroup(−CH2–),whichisattachedtotheoxygenofahydroxylgroup(−OH).Itisaconstitutionalisomerofdimethylether.EthanolissometimesabbreviatedasEtOH,usingthecommonorganicchemistrynotationofrepresentingtheethylgroup(C2H5−)withEt. Physicalproperties[edit] Ethanolburningwithitsspectrumdepicted Ethanolisavolatile,colorlessliquidthathasaslightodor.Itburnswithasmokelessblueflamethatisnotalwaysvisibleinnormallight.Thephysicalpropertiesofethanolstemprimarilyfromthepresenceofitshydroxylgroupandtheshortnessofitscarbonchain.Ethanol'shydroxylgroupisabletoparticipateinhydrogenbonding,renderingitmoreviscousandlessvolatilethanlesspolarorganiccompoundsofsimilarmolecularweight,suchaspropane. Ethanolisslightlymorerefractivethanwater,havingarefractiveindexof1.36242(atλ=589.3 nmand18.35 °Cor65.03 °F).[68]Thetriplepointforethanolis150Katapressureof4.3×10−4Pa.[69] Solventproperties[edit] Ethanolisaversatilesolvent,misciblewithwaterandwithmanyorganicsolvents,includingaceticacid,acetone,benzene,carbontetrachloride,chloroform,diethylether,ethyleneglycol,glycerol,nitromethane,pyridine,andtoluene.Itsmainuseasasolventisinmakingtinctureofiodine,coughsyrupsetc.[68][70]Itisalsomisciblewithlightaliphatichydrocarbons,suchaspentaneandhexane,andwithaliphaticchloridessuchastrichloroethaneandtetrachloroethylene.[70] Ethanol'smiscibilitywithwatercontrastswiththeimmiscibilityoflonger-chainalcohols(fiveormorecarbonatoms),whosewatermiscibilitydecreasessharplyasthenumberofcarbonsincreases.[71]Themiscibilityofethanolwithalkanesislimitedtoalkanesuptoundecane:mixtureswithdodecaneandhigheralkanesshowamiscibilitygapbelowacertaintemperature(about13 °Cfordodecane[72]).Themiscibilitygaptendstogetwiderwithhigheralkanes,andthetemperatureforcompletemiscibilityincreases. Ethanol-watermixtureshavelessvolumethanthesumoftheirindividualcomponentsatthegivenfractions.Mixingequalvolumesofethanolandwaterresultsinonly1.92volumesofmixture.[68][73]Mixingethanolandwaterisexothermic,withupto777 J/mol[74]beingreleasedat298 K. Mixturesofethanolandwaterformanazeotropeatabout89mole-%ethanoland11mole-%water[75]oramixtureof95.6percentethanolbymass(orabout97%alcoholbyvolume)atnormalpressure,whichboilsat351K(78 °C).Thisazeotropiccompositionisstronglytemperature-andpressure-dependentandvanishesattemperaturesbelow303 K.[76] Hydrogenbondinginsolidethanolat−186 °C Hydrogenbondingcausespureethanoltobehygroscopictotheextentthatitreadilyabsorbswaterfromtheair.Thepolarnatureofthehydroxylgroupcausesethanoltodissolvemanyioniccompounds,notablysodiumandpotassiumhydroxides,magnesiumchloride,calciumchloride,ammoniumchloride,ammoniumbromide,andsodiumbromide.[70]Sodiumandpotassiumchloridesareslightlysolubleinethanol.[70]Becausetheethanolmoleculealsohasanonpolarend,itwillalsodissolvenonpolarsubstances,includingmostessentialoils[77]andnumerousflavoring,coloring,andmedicinalagents. Theadditionofevenafewpercentofethanoltowatersharplyreducesthesurfacetensionofwater.Thispropertypartiallyexplainsthe"tearsofwine"phenomenon.Whenwineisswirledinaglass,ethanolevaporatesquicklyfromthethinfilmofwineonthewalloftheglass.Asthewine'sethanolcontentdecreases,itssurfacetensionincreasesandthethinfilm"beadsup"andrunsdowntheglassinchannelsratherthanasasmoothsheet. Flammability[edit] Anethanol–watersolutionwillcatchfireifheatedaboveatemperaturecalleditsflashpointandanignitionsourceisthenappliedtoit.[78]For20%alcoholbymass(about25%byvolume),thiswilloccuratabout25 °C(77 °F).Theflashpointofpureethanolis13 °C(55 °F),[79]butmaybeinfluencedveryslightlybyatmosphericcompositionsuchaspressureandhumidity.Ethanolmixturescanignitebelowaverageroomtemperature.Ethanolisconsideredaflammableliquid(Class3HazardousMaterial)inconcentrationsabove2.35%bymass(3.0%byvolume;6proof).[80][81][82] Flashpointsofethanol–watermixtures[83][81][84] Ethanolmassfraction, % Temperature °C °F 1 84.5 184.1[81] 2 64 147[81] 2.35 60 140[81][80] 3 51.5 124.7[81] 5 43 109[83] 6 39.5 103.1[81] 10 31 88[83] 20 25 77[81] 30 24 75[83] 40 21.9 71.4[citationneeded][83] 50 20 68[83][81] 60 17.9 64.2[citationneeded][83] 70 16 61[83] 80 15.8 60.4[81] 90 14 57[83] 100 12.5 54.5[83][81][79] Dishesusingburningalcoholforculinaryeffectsarecalledflambé. Naturaloccurrence[edit] Ethanolisabyproductofthemetabolicprocessofyeast.Assuch,ethanolwillbepresentinanyyeasthabitat.Ethanolcancommonlybefoundinoverripefruit.[85]Ethanolproducedbysymbioticyeastcanbefoundinbertampalmblossoms.Althoughsomeanimalspecies,suchasthepentailedtreeshrew,exhibitethanol-seekingbehaviors,mostshownointerestoravoidanceoffoodsourcescontainingethanol.[86]Ethanolisalsoproducedduringthegerminationofmanyplantsasaresultofnaturalanaerobiosis.[87]Ethanolhasbeendetectedinouterspace,forminganicycoatingarounddustgrainsininterstellarclouds.[88] Minutequantityamounts(average196ppb)ofendogenousethanolandacetaldehydewerefoundintheexhaledbreathofhealthyvolunteers.[89]Auto-brewerysyndrome,alsoknownasgutfermentationsyndrome,isararemedicalconditioninwhichintoxicatingquantitiesofethanolareproducedthroughendogenousfermentationwithinthedigestivesystem.[90] Production[edit] 94%denaturedethanolsoldinabottleforhouseholduse Ethanolisproducedbothasapetrochemical,throughthehydrationofethyleneand,viabiologicalprocesses,byfermentingsugarswithyeast.[91]Whichprocessismoreeconomicaldependsonprevailingpricesofpetroleumandgrainfeedstocks.Inthe1970smostindustrialethanolintheUnitedStateswasmadeasapetrochemical,butinthe1980stheUnitedStatesintroducedsubsidiesforcorn-basedethanolandtodayitisalmostallmadefromthatsource.[92]InIndiaethanolismadefromsugarcane.[93] Ethylenehydration[edit] Ethanolforuseasanindustrialfeedstockorsolvent(sometimesreferredtoassyntheticethanol)ismadefrompetrochemicalfeedstocks,primarilybytheacid-catalyzedhydrationofethylene: C2H4+H2O→CH3CH2OH Thecatalystismostcommonlyphosphoricacid,[94][95]adsorbedontoaporoussupportsuchassilicagelordiatomaceousearth.Thiscatalystwasfirstusedforlarge-scaleethanolproductionbytheShellOilCompanyin1947.[96]Thereactioniscarriedoutinthepresenceofhighpressuresteamat300 °C(572 °F)wherea5:3ethylenetosteamratioismaintained.[97][98]ThisprocesswasusedonanindustrialscalebyUnionCarbideCorporationandothersintheUS,butnowonlyLyondellBasellusesitcommercially. Inanolderprocess,firstpracticedontheindustrialscalein1930byUnionCarbide,[99]butnowalmostentirelyobsolete,ethylenewashydratedindirectlybyreactingitwithconcentratedsulfuricacidtoproduceethylsulfate,whichwashydrolyzedtoyieldethanolandregeneratethesulfuricacid:[100] C2H4+H2SO4→CH3CH2SO4H CH3CH2SO4H+H2O→CH3CH2OH+H2SO4 FromCO2[edit] Ethanolhasbeenproducedinthelaboratorybyconvertingcarbondioxideviabiologicalandelectrochemicalreactions.[101][102] CO2+H2O→CH3CH2OH+sideproducts Fermentation[edit] Mainarticle:Ethanolfermentation Seealso:Yeastinwinemaking Ethanolinalcoholicbeveragesandfuelisproducedbyfermentation.Certainspeciesofyeast(e.g.,Saccharomycescerevisiae)metabolizesugar,producingethanolandcarbondioxide.Thechemicalequationsbelowsummarizetheconversion: C6H12O6→2CH3CH2OH+2CO2 C12H22O11+H2O→4CH3CH2OH+4CO2 Fermentationistheprocessofculturingyeastunderfavorablethermalconditionstoproducealcohol.Thisprocessiscarriedoutataround35–40 °C(95–104 °F).Toxicityofethanoltoyeastlimitstheethanolconcentrationobtainablebybrewing;higherconcentrations,therefore,areobtainedbyfortificationordistillation.Themostethanol-tolerantyeaststrainscansurviveuptoapproximately18%ethanolbyvolume. Toproduceethanolfromstarchymaterialssuchascereals,thestarchmustfirstbeconvertedintosugars.Inbrewingbeer,thishastraditionallybeenaccomplishedbyallowingthegraintogerminate,ormalt,whichproducestheenzymeamylase.Whenthemaltedgrainismashed,theamylaseconvertstheremainingstarchesintosugars. Cellulose[edit] Mainarticle:Cellulosicethanol Sugarsforethanolfermentationcanbeobtainedfromcellulose.Deploymentofthistechnologycouldturnanumberofcellulose-containingagriculturalby-products,suchascorncobs,straw,andsawdust,intorenewableenergyresources.Otheragriculturalresiduessuchassugarcanebagasseandenergycropssuchasswitchgrassmayalsobefermentablesugarsources.[103] Testing[edit] Infraredreflectionspectraofliquidethanol,showingthe−OHbandcenterednear3300 cm−1andC−Hbandsnear2950 cm−1 Near-infraredspectrumofliquidethanol Breweriesandbiofuelplantsemploytwomethodsformeasuringethanolconcentration.InfraredethanolsensorsmeasurethevibrationalfrequencyofdissolvedethanolusingtheC−Hbandat2900 cm−1.Thismethodusesarelativelyinexpensivesolid-statesensorthatcomparestheC−Hbandwithareferencebandtocalculatetheethanolcontent.ThecalculationmakesuseoftheBeer–Lambertlaw.Alternatively,bymeasuringthedensityofthestartingmaterialandthedensityoftheproduct,usingahydrometer,thechangeinspecificgravityduringfermentationindicatesthealcoholcontent.Thisinexpensiveandindirectmethodhasalonghistoryinthebeerbrewingindustry. Purification[edit] Distillation[edit] Ethylenehydrationorbrewingproducesanethanol–watermixture.Formostindustrialandfueluses,theethanolmustbepurified.Fractionaldistillationatatmosphericpressurecanconcentrateethanolto95.6%byweight(89.5mole%).Thismixtureisanazeotropewithaboilingpointof78.1 °C(172.6 °F),andcannotbefurtherpurifiedbydistillation.Additionofanentrainingagent,suchasbenzene,cyclohexane,orheptane,allowsanewternaryazeotropecomprisingtheethanol,water,andtheentrainingagenttobeformed.Thislower-boilingternaryazeotropeisremovedpreferentially,leadingtowater-freeethanol.[95] Molecularsievesanddesiccants[edit] Apartfromdistillation,ethanolmaybedriedbyadditionofadesiccant,suchasmolecularsieves,cellulose,orcornmeal.Thedesiccantscanbedriedandreused.[95]Molecularsievescanbeusedtoselectivelyabsorbthewaterfromthe95.6%ethanolsolution.[104]Molecularsievesofpore-size3 Ångstrom,atypeofzeolite,effectivelysequesterwatermoleculeswhileexcludingethanolmolecules.Heatingthewetsievesdrivesoutthewater,allowingregenerationoftheirdessicantcapability.[105] Membranesandreverseosmosis[edit] Membranescanalsobeusedtoseparateethanolandwater.Membrane-basedseparationsarenotsubjecttothelimitationsofthewater-ethanolazeotropebecausetheseparationsarenotbasedonvapor-liquidequilibria.Membranesareoftenusedintheso-calledhybridmembranedistillationprocess.Thisprocessusesapre-concentrationdistillationcolumnasthefirstseparatingstep.Thefurtherseparationisthenaccomplishedwithamembraneoperatedeitherinvaporpermeationorpervaporationmode.Vaporpermeationusesavapormembranefeedandpervaporationusesaliquidmembranefeed. Othertechniques[edit] Avarietyofothertechniqueshavebeendiscussed,includingthefollowing:[95] Saltingusingpotassiumcarbonatetoexploititsinsolubilitywillcauseaphaseseparationwithethanolandwater.Thisoffersaverysmallpotassiumcarbonateimpuritytothealcoholthatcanberemovedbydistillation.Thismethodisveryusefulinpurificationofethanolbydistillation,asethanolformsanazeotropewithwater. Directelectrochemicalreductionofcarbondioxidetoethanolunderambientconditionsusingcoppernanoparticlesonacarbonnanospikefilmasthecatalyst;[106] Extractionofethanolfromgrainmashbysupercriticalcarbondioxide; Pervaporation; Fractionalfreezingisalsousedtoconcentratefermentedalcoholicsolutions,suchastraditionallymadeApplejack(beverage); Pressureswingadsorption.[107] Gradesofethanol[edit] Denaturedalcohol[edit] Mainarticle:Denaturedalcohol Pureethanolandalcoholicbeveragesareheavilytaxedaspsychoactivedrugs,butethanolhasmanyusesthatdonotinvolveitsconsumption.Torelievethetaxburdenontheseuses,mostjurisdictionswaivethetaxwhenanagenthasbeenaddedtotheethanoltorenderitunfittodrink.Theseincludebitteringagentssuchasdenatoniumbenzoateandtoxinssuchasmethanol,naphtha,andpyridine.Productsofthiskindarecalleddenaturedalcohol.[108][109] Absolutealcohol[edit] Absoluteoranhydrousalcoholreferstoethanolwithalowwatercontent.Therearevariousgradeswithmaximumwatercontentsrangingfrom1%toafewpartspermillion(ppm).Ifazeotropicdistillationisusedtoremovewater,itwillcontaintraceamountsofthematerialseparationagent(e.g.benzene).[110]Absolutealcoholisnotintendedforhumanconsumption.Absoluteethanolisusedasasolventforlaboratoryandindustrialapplications,wherewaterwillreactwithotherchemicals,andasfuelalcohol.Spectroscopicethanolisanabsoluteethanolwithalowabsorbanceinultravioletandvisiblelight,fitforuseasasolventinultraviolet-visiblespectroscopy.[111] Pureethanolisclassedas200proofintheUS,equivalentto175degreesproofintheUKsystem.[112] Rectifiedspirits[edit] Rectifiedspirit,anazeotropiccompositionof96%ethanolcontaining4%water,isusedinsteadofanhydrousethanolforvariouspurposes.Spiritsofwineareabout94%ethanol(188proof).Theimpuritiesaredifferentfromthosein95%(190proof)laboratoryethanol.[113] Reactions[edit] Furtherinformation:Alcohol(chemistry) Ethanolisclassifiedasaprimaryalcohol,meaningthatthecarbonthatitshydroxylgroupattachestohasatleasttwohydrogenatomsattachedtoitaswell.Manyethanolreactionsoccuratitshydroxylgroup. Esterformation[edit] Inthepresenceofacidcatalysts,ethanolreactswithcarboxylicacidstoproduceethylestersandwater: RCOOH+HOCH2CH3→RCOOCH2CH3+H2O Thisreaction,whichisconductedonlargescaleindustrially,requirestheremovalofthewaterfromthereactionmixtureasitisformed.Estersreactinthepresenceofanacidorbasetogivebackthealcoholandasalt.Thisreactionisknownassaponificationbecauseitisusedinthepreparationofsoap.Ethanolcanalsoformesterswithinorganicacids.Diethylsulfateandtriethylphosphatearepreparedbytreatingethanolwithsulfurtrioxideandphosphoruspentoxiderespectively.Diethylsulfateisausefulethylatingagentinorganicsynthesis.Ethylnitrite,preparedfromthereactionofethanolwithsodiumnitriteandsulfuricacid,wasformerlyusedasadiuretic. Dehydration[edit] Inthepresenceofacidcatalysts,ethanolconvertstoethylene.Typicallysolidacidssuchasaluminaareused:[114]   CH3CH2OH→H2C=CH2+H2O Ethyleneproducedfromsugar-derivedethanol(primarilyinBrazil)competeswithethyleneproducedfrompetrochemicalfeedstockssuchasnaphthaandethane. Underalternativeconditions,diethyletherresults: 2CH3CH2OH→CH3CH2OCH2CH3+H2O Combustion[edit] Completecombustionofethanolformscarbondioxideandwater: C2H5OH(l)+3O2(g)→2CO2(g)+3H2O(l);−ΔHc=1371 kJ/mol[115]=29.8 kJ/g=327 kcal/mol=7.1 kcal/g C2H5OH(l)+3O2(g)→2CO2(g)+3H2O(g);−ΔHc=1236 kJ/mol=26.8 kJ/g=295.4 kcal/mol=6.41kcal/g[116] Specificheat=2.44kJ/(kg·K) Acid-basechemistry[edit] EthanolisaneutralmoleculeandthepHofasolutionofethanolinwaterisnearly7.00.Ethanolcanbequantitativelyconvertedtoitsconjugatebase,theethoxideion(CH3CH2O−),byreactionwithanalkalimetalsuchassodium:[71] 2CH3CH2OH+2Na→2CH3CH2ONa+H2 oraverystrongbasesuchassodiumhydride: CH3CH2OH+NaH→CH3CH2ONa+H2 Theaciditiesofwaterandethanolarenearlythesame,asindicatedbytheirpKaof15.7and16respectively.Thus,sodiumethoxideandsodiumhydroxideexistinanequilibriumthatiscloselybalanced: CH3CH2OH+NaOH⇌CH3CH2ONa+H2O Halogenation[edit] Ethanolisnotusedindustriallyasaprecursortoethylhalides,butthereactionsareillustrative.EthanolreactswithhydrogenhalidestoproduceethylhalidessuchasethylchlorideandethylbromideviaanSN2reaction: CH3CH2OH+HCl→CH3CH2Cl+H2O Thesereactionsrequireacatalystsuchaszincchloride.[100] HBrrequiresrefluxingwithasulfuricacidcatalyst.[100]Ethylhalidescan,inprinciple,alsobeproducedbytreatingethanolwithmorespecializedhalogenatingagents,suchasthionylchlorideorphosphorustribromide.[71][100] CH3CH2OH+SOCl2→CH3CH2Cl+SO2+HCl Upontreatmentwithhalogensinthepresenceofbase,ethanolgivesthecorrespondinghaloform(CHX3,whereX=Cl,Br,I).Thisconversioniscalledthehaloformreaction.[117]" Anintermediateinthereactionwithchlorineisthealdehydecalledchloral,whichformschloralhydrateuponreactionwithwater:[118] 4Cl2+CH3CH2OH→CCl3CHO+5HCl CCl3CHO+H2O→CCl3C(OH)2H Oxidation[edit] Ethanolcanbeoxidizedtoacetaldehydeandfurtheroxidizedtoaceticacid,dependingonthereagentsandconditions.[100]Thisoxidationisofnoimportanceindustrially,butinthehumanbody,theseoxidationreactionsarecatalyzedbytheenzymeliveralcoholdehydrogenase.Theoxidationproductofethanol,aceticacid,isanutrientforhumans,beingaprecursortoacetylCoA,wheretheacetylgroupcanbespentasenergyorusedforbiosynthesis. Metabolism[edit] Ethanolissimilartomacronutrientssuchasproteins,fats,andcarbohydratesinthatitprovidescalories.Whenconsumedandmetabolized,itcontributes7caloriespergramviaethanolmetabolism.[119] Safety[edit] Seealso:Alcohol(chemistry)§ Toxicity Pureethanolwillirritatetheskinandeyes.[120]Nausea,vomiting,andintoxicationaresymptomsofingestion.Long-termusebyingestioncanresultinseriousliverdamage.[121]AtmosphericconcentrationsaboveoneinathousandareabovetheEuropeanUnionoccupationalexposurelimits.[121] History[edit] Furtherinformation:Distilledbeverage Thefermentationofsugarintoethanolisoneoftheearliestbiotechnologiesemployedbyhumans.Ethanolhashistoricallybeenidentifiedvariouslyasspiritofwineorardentspirits,[122]andasaquavitaeoraquavita.Theintoxicatingeffectsofitsconsumptionhavebeenknownsinceancienttimes.Ethanolhasbeenusedbyhumanssinceprehistoryastheintoxicatingingredientofalcoholicbeverages.Driedresidueon9,000-year-oldpotteryfoundinChinasuggeststhatNeolithicpeopleconsumedalcoholicbeverages.[123] TheinflammablenatureoftheexhalationsofwinewasalreadyknowntoancientnaturalphilosopherssuchasAristotle(384–322BCE),Theophrastus(c.371–287BCE),andPlinytheElder(23/24–79CE).[124]However,thisdidnotimmediatelyleadtotheisolationofethanol,evendespitethedevelopmentofmoreadvanceddistillationtechniquesinsecond-andthird-centuryRomanEgypt.[125]Animportantrecognition,firstfoundinoneofthewritingsattributedtoJābiribnḤayyān(ninthcenturyCE),wasthatbyaddingsalttoboilingwine,whichincreasesthewine'srelativevolatility,theflammabilityoftheresultingvaporsmaybeenhanced.[126]ThedistillationofwineisattestedinArabicworksattributedtoal-Kindī(c.801–873CE)andtoal-Fārābī(c.872–950),andinthe28thbookofal-Zahrāwī's(Latin:Abulcasis,936–1013)Kitābal-Taṣrīf(latertranslatedintoLatinasLiberservatoris).[127]Inthetwelfthcentury,recipesfortheproductionofaquaardens("burningwater",i.e.,ethanol)bydistillingwinewithsaltstartedtoappearinanumberofLatinworks,andbytheendofthethirteenthcenturyithadbecomeawidelyknownsubstanceamongWesternEuropeanchemists.[128] TheworksofTaddeoAlderotti(1223–1296)describeamethodforconcentratingethanolinvolvingrepeatedfractionaldistillationthroughawater-cooledstill,bywhichanethanolpurityof90%couldbeobtained.[129]ThemedicinalpropertiesofethanolwerestudiedbyArnaldofVillanova(1240–1311CE)andJohnofRupescissa(c.1310–1366),thelatterofwhomregardeditasalife-preservingsubstanceabletopreventalldiseases(theaquavitaeor"wateroflife",alsocalledbyJohnthequintessenceofwine).[130] InChina,archaeologicalevidenceindicatesthatthetruedistillationofalcoholbeganduringtheJin(1115–1234)orSouthernSong(1127–1279)dynasties.[131]AstillhasbeenfoundatanarchaeologicalsiteinQinglong,Hebei,datingtothe12thcentury.[131]InIndia,thetruedistillationofalcoholwasintroducedfromtheMiddleEast,andwasinwideuseintheDelhiSultanatebythe14thcentury.[132] In1796,German-RussianchemistJohannTobiasLowitzobtainedpureethanolbymixingpartiallypurifiedethanol(thealcohol-waterazeotrope)withanexcessofanhydrousalkaliandthendistillingthemixtureoverlowheat.[133]FrenchchemistAntoineLavoisierdescribedethanolasacompoundofcarbon,hydrogen,andoxygen,andin1807Nicolas-ThéodoredeSaussuredeterminedethanol'schemicalformula.[134][135]Fiftyyearslater,ArchibaldScottCouperpublishedthestructuralformulaofethanol.Itwasoneofthefirststructuralformulasdetermined.[136] Ethanolwasfirstpreparedsyntheticallyin1825byMichaelFaraday.Hefoundthatsulfuricacidcouldabsorblargevolumesofcoalgas.[137]HegavetheresultingsolutiontoHenryHennell,aBritishchemist,whofoundin1826thatitcontained"sulphovinicacid"(ethylhydrogensulfate).[138]In1828,HennellandtheFrenchchemistGeorges-SimonSerullasindependentlydiscoveredthatsulphovinicacidcouldbedecomposedintoethanol.[139][140]Thus,in1825Faradayhadunwittinglydiscoveredthatethanolcouldbeproducedfromethylene(acomponentofcoalgas)byacid-catalyzedhydration,aprocesssimilartocurrentindustrialethanolsynthesis.[141] EthanolwasusedaslampfuelintheUnitedStatesasearlyas1840,butataxleviedonindustrialalcoholduringtheCivilWarmadethisuseuneconomical.Thetaxwasrepealedin1906.[142]Useasanautomotivefueldatesbackto1908,withtheFordModelTabletorunonpetrol(gasoline)orethanol.[143]Itfuelssomespiritlamps. Ethanolintendedforindustrialuseisoftenproducedfromethylene.[144]Ethanolhaswidespreaduseasasolventofsubstancesintendedforhumancontactorconsumption,includingscents,flavorings,colorings,andmedicines.Inchemistry,itisbothasolventandafeedstockforthesynthesisofotherproducts.Ithasalonghistoryasafuelforheatandlight,andmorerecentlyasafuelforinternalcombustionengines. 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^HennellH(1828)."Onthemutualactionofsulfuricacidandalcohol,andonthenatureoftheprocessbywhichetherisformed".PhilosophicalTransactionsoftheRoyalSocietyofLondon.118:365–371.doi:10.1098/rstl.1828.0021.S2CID 98483646.Onpage368,Hennellproducesethanolfrom"sulfovinicacid"(ethylhydrogensulfate). ^SérullasG(1828).GuytondeMorveauL,Gay-LussacJL,AragoF,MichelEugèneChevreul,MarcellinBerthelot,ÉleuthèreÉlieNicolasMascart,AlbinHaller(eds.)."Del'actiondel'acidesulfuriquesurl'alcool,etdesproduitsquienrésultent".AnnalesdeChimieetdePhysique.39:152–186.Onpage158,Sérullasmentionstheproductionofalcoholfrom"sulfateacidd'hydrogènecarboné"(hydrocarbonacidsulfate). ^In1855,theFrenchchemistMarcellinBerthelotconfirmedFaraday'sdiscoverybypreparingethanolfrompureethylene.BerthelotM(1855).AragoF,Gay-LussacJL(eds.)."Surlaformationdel'alcoolaumoyendubicarbured'hydrogène(Ontheformationofalcoholbymeansofethylene)".AnnalesdeChimieetdePhysique.43:385–405.(Note:ThechemicalformulasinBerthelot'spaperarewrongbecausechemistsatthattimeusedthewrongatomicmassesfortheelements;e.g.,carbon(6insteadof12),oxygen(8insteadof16),etc.) ^SiegelR(15February2007)."Ethanol,OnceBypassed,NowSurgingAhead".NPR.Retrieved22September2007. ^DiPardoJ."OutlookforBiomassEthanolProductionandDemand"(PDF).UnitedStatesDepartmentofEnergy.Archivedfromtheoriginal(PDF)on24September2015.Retrieved22September2007. ^MyersRL,MyersRL(2007).The100mostimportantchemicalcompounds:areferenceguide.Westport,CN:GreenwoodPress.p. 122.ISBN 978-0-313-33758-1. Furtherreading[edit] BoyceJM,PittetD(2003)."HandHygieneinHealthcareSettings".Atlanta,GA:CentersforDiseaseControl.. OnukiS,KozielJA,vanLeeuwenJ,JenksWS,GrewellD,CaiL(June2008).Ethanolproduction,purification,andanalysistechniques:areview.2008ASABEAnnualInternationalMeeting.Providence,RI.Retrieved16February2013. "ExplanationofUSdenaturedalcoholdesignations".Sci-toys. Lange,NorbertAdolph(1967).JohnAurieDean(ed.).Lange'sHandbookofChemistry(10th ed.).McGraw-Hill. Externallinks[edit] Lookupalcohol orethanolinWiktionary,thefreedictionary. WikimediaCommonshasmediarelatedtoEthanol. Alcohol(Ethanol)atThePeriodicTableofVideos(UniversityofNottingham) InternationalLabourOrganizationethanolsafetyinformation NationalPollutantInventory–EthanolFactSheet CDC–NIOSHPocketGuidetoChemicalHazards–EthylAlcohol NationalInstituteofStandardsandTechnologychemicaldataonethanol ChicagoBoardofTradenewsandmarketdataonethanolfutures Calculationofvaporpressure,liquiddensity,dynamicliquidviscosity,surfacetensionofethanol EthanolHistoryAlookintothehistoryofethanol ChemSubOnline:Ethylalcohol Industrialethanolproductionprocessflowdiagramusingethyleneandsulphuricacid vteAlcoholsByconsumptionAlcoholsfoundinalcoholicdrinks 1-Propanol 2-Methyl-1-butanol Ethanol Isoamylalcohol Isobutanol Phenethylalcohol tert-Amylalcohol tert-Butylalcohol Tryptophol Medicalalcohol Ethchlorvynol Methylpentynol Methanolpoisoning Ethanol Toxicalcohols Isopropylalcohol Methanol Primaryalcohols(1°)Methanol 4-Methylcyclohexanemethanol Aminomethanol Cyclohexylmethanol Methoxymethanol Methylazoxymethanol Trifluoromethanol Ethanol 1-Aminoethanol 2,2,2-Trichloroethanol 2,2,2-Trifluoroethanol 2-(2-Ethoxyethoxy)ethanol 2-(2-Methoxyethoxy)ethanol 2-(2-Methoxyethoxy)ethanol 2-Butoxyethanol 2-Chloroethanol 2-Ethoxyethanol 2-Fluoroethanol 2-Mercaptoethanol 2-Methoxyethanol Aminoethylethanolamine Diethylethanolamine Dimethylethanolamine Ethanol Ethanolamine N,N-Diisopropylaminoethanol N-Methylethanolamine Phenoxyethanol Tribromoethanol Butanol 2-Methyl-1-butanol Isobutanol n-Butanol Straight-chainsaturatedC1—C9 Methanol Ethanol 1-Propanol 1-Butanol 1-Pentanol 1-Hexanol 1-Heptanol 1-Octanol(capryl) 1-Nonanol(pelargonic) Straight-chainsaturatedC10—C19 1-Decanol(capric) 1-Undecanol(hendecyl) 1-Dodecanol(lauryl) 1-Tridecanol 1-Tetradecanol(myristyl) 1-Pentadecanol 1-Hexadecanol(cetyl/palmityl) 1-Heptadecanol 1-Octadecanol(stearyl) 1-Nonadecanol Straight-chainsaturatedC20—C29 1-Icosanol(arachidyl) 1-Heneicosanol 1-Docosanol(behenyl) 1-Tricosanol 1-Tetracosanol(lignoceryl) 1-Pentacosanol 1-Hexacosanol(ceryl) 1-Heptacosanol 1-Octacosanol(cluytyl/montanyl) 1-Nonacosanol Straight-chainsaturatedC30—C39 1-Triacontanol(melissyl/myricyl) 1-Hentriacontanol 1-Dotriacontanol(lacceryl) 1-Tritriacontanol 1-Tetratriacontanol(geddyl) 1-Pentatriacontanol 1-Hexatriacontanol 1-Heptatriacontanol 1-Octatriacontanol 1-Nonatriacontanol Straight-chainsaturatedC40—C49 1-Tetracontanol 1-Hentetracontanol 1-Dotetracontanol 1-Tritetracontanol 1-Tetratetracontanol 1-Pentatetracontanol 1-Hexatetracontanol 1-Heptatetracontanol 1-Octatetracontanol 1-Nonatetracontanol 2-Ethylhexanol Allylalcohol Anisylalcohol Benzylalcohol Cinnamylalcohol Crotylalcohol Furfurylalcohol Isoamylalcohol Neopentylalcohol Nicotinylalcohol Perillylalcohol Phenethylalcohol Prenol Propargylalcohol Salicylalcohol Tryptophol Vanillylalcohol VeratrolealcoholSecondaryalcohols(2°) 1-Phenylethanol 2-Butanol 2-Deoxyerythritol 2-Heptanol 3-Heptanol 2-Hexanol 3-Hexanol 3-Methyl-2-butanol 2-Nonanol 2-Octanol 2-Pentanol 3-Pentanol Cyclohexanol Cyclopentanol Cyclopropanol Diphenylmethanol Isopropanol Pinacolylalcohol Pirkle'salcohol Propyleneglycolmethylether Tertiaryalcohols(3°) 2-Methyl-2-pentanol 2-Methylheptan-2-ol 2-Methylhexan-2-ol 3-Methyl-3-pentanol 3-Methyloctan-3-ol Diacetonealcohol Ethchlorvynol Methylpentynol Nonafluoro-tert-butylalcohol tert-Amylalcohol tert-Butylalcohol Triphenylethanol Triphenylmethanol HydricalcoholsMonohydricalcohols Methanol Ethanol Isopropanol Dihydricalcohols Ethyleneglycol Propyleneglycol Trihydricalcohols Glycerol Polyhydricalcohols Pentaerythritol Amylalcohols 2,2-Dimethylpropan-1-ol 2-Methylbutan-1-ol 2-Methylbutan-2-ol 3-Methylbutan-1-ol 3-Methylbutan-2-ol Pentan-1-ol Pentan-2-ol Pentan-3-ol Aromaticalcohols Benzylalcohol 2,4-Dichlorobenzylalcohol 3-Nitrobenzylalcohol Saturatedfattyalcohols Cetostearylalcohol Decanol Laurylalcohol Myristylalcohol Nonanol Octanol Tridecanol Undecanol Branchedandunsaturatedfattyalcohols 3-Methyl-3-pentanol Erucylalcohol Linolenylalcohol Linoleylalcohol Oleylalcohol Palmitoleylalcohol tert-Amylalcohol tert-Butylalcohol SugaralcoholsC2—C7 Ethyleneglycol(C2) Glycerol(C3) Erythritol(C4) Threitol(C4) Arabitol(C5) Ribitol(C5) Xylitol(C5) Mannitol(C6) Sorbitol(C6) Galactitol(C6) Iditol(C6) Volemitol(C7) Deoxysugaralcohols Fucitol Cyclicsugaralcohols Inositol Glycylglycitols Maltitol Lactitol Isomalt Maltotriitol Maltotetraitol Polyglycitol TerpenealcoholsMonoterpenealcohols Borneol Citronellol Geraniol Linalool Menthol Nerol Rhodinol Terpineol Sesquiterpenealcohols Bisabolol Farnesol Nerolidol Patchoulol Diterpenealcohols Phytol Dialcohols 1,4-Butanediol 1,5-Pentanediol 2-Methyl-2-propyl-1,3-propanediol Diethylpropanediol Ethyleneglycol Trialcohols Glycerol Sterols Cholesterol Ergosterol Lanosterol β-Sitosterol Stigmasterol Fluoroalcohols 1,3-Difluoro-2-propanol 2,2,2-Trifluoroethanol 2-Fluoroethanol Nonafluoro-tert-butylalcohol Trifluoromethanol Preparations Substitutionofhaloalkane Carbonylreduction Ethercleavage Hydrolysisofepoxide Hydrationofalkene Zieglerprocess Reactions Deprotonation Protonation Alcoholoxidation Glycolcleavage Nucleophilicsubstitution Fischer–Speieresterification Williamsonethersynthesis Eliminationreaction Nucleophilicsubstitutionofcarbonylgroup Friedel-Craftsalkylation Nucleophilicconjugateaddition Transesterification Category vteMotorfuelsFueltypes Gasoline/petrol Diesel Biodiesel Biogasoline LeadReplacementPetrol Electricity Kerosene Compressednaturalgas Hydrogen Ethanol Butanolfuel Racingfuel(Tetraethyllead) Fueladditives Butylrubber Butylatedhydroxytoluene 1,2-Dibromoethane 1,2-Dichloroethane Dimethylmethylphosphonate 2,4-Dimethyl-6-tert-butylphenol Dinonylnaphthylsulfonicacid 2,6-Di-tert-butylphenol Ecalene Ethylenediamine Metaldeactivator Methyltert-butylether Nitromethane Tetraethyllead Tetranitromethane Fluids Motoroil Antifreeze Automatictransmissionfluid Brakefluid Gearoil Windshieldwasherfluid Retail Fuelcard Fullservice MTBEcontroversy Payatthepump vteMoleculesdetectedinouterspaceMoleculesDiatomic Aluminiummonochloride Aluminiummonofluoride Aluminium(II)oxide Argonium Carbonmonophosphide Carbonmonosulfide Carbonmonoxide Cyanoradical Diatomiccarbon Fluoromethylidynium Heliumhydrideion Hydrogenchloride Hydrogenfluoride Hydrogen(molecular) Hydroxylradical Iron(II)oxide Magnesiummonohydride Methylidyneradical Nitricoxide Nitrogen(molecular) Imidogen Sulfurmononitride Oxygen(molecular) Phosphorusmonoxide Phosphorusmononitride Potassiumchloride Siliconcarbide Siliconmonoxide Siliconmonosulfide Sodiumchloride Sodiumiodide Sulfurmonohydride Sulfurmonoxide Titanium(II)oxide Triatomic Aluminium(I)hydroxide Aluminiumisocyanide Aminoradical Carbondioxide Carbonylsulfide CCPradical Chloronium Diazenylium Dicarbonmonoxide Disiliconcarbide Ethynylradical Formylradical Hydrogencyanide(HCN) Hydrogenisocyanide(HNC) Hydrogensulfide Hydroperoxyl Ironcyanide Isoformyl Magnesiumcyanide Magnesiumisocyanide Methyleneradical N2H+ Nitrousoxide Nitroxyl Ozone Phosphaethyne Potassiumcyanide Protonatedmolecularhydrogen Sodiumcyanide Sodiumhydroxide Siliconcarbonitride c-Silicondicarbide SiNC Sulfurdioxide Thioformyl Thioxoethenylidene Titaniumdioxide Tricarbon Water Fouratoms Acetylene Ammonia Cyanicacid Cyanoethynyl Formaldehyde Fulminicacid HCCN Hydrogenperoxide Hydromagnesiumisocyanide Isocyanicacid Isothiocyanicacid Ketenyl Methyleneamidogen Methylradical Propynylidyne Protonatedcarbondioxide Protonatedhydrogencyanide Silicontricarbide Thioformaldehyde Tricarbonmonoxide Tricarbonmonosulfide Thiocyanicacid Fiveatoms Ammoniumion Butadiynyl Carbodiimide Cyanamide Cyanoacetylene Cyanoformaldehyde Cyanomethyl Cyclopropenylidene Formicacid Isocyanoacetylene Ketene Methane Methoxyradical Methylenimine Propadienylidene Protonatedformaldehyde Silane Silicon-carbidecluster Sixatoms Acetonitrile Cyanobutadiynylradical E-Cyanomethanimine Cyclopropenone Diacetylene Ethylene Formamide HC4N Ketenimine Methanethiol Methanol Methylisocyanide Pentynylidyne Propynal Protonatedcyanoacetylene Sevenatoms Acetaldehyde Acrylonitrile Vinylcyanide Cyanodiacetylene Ethyleneoxide Glycolonitrile Hexatriynylradical Methylacetylene Methylamine Methylisocyanate Vinylalcohol Eightatoms Aceticacid Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Heptatrienylradical Hexapentaenylidene Methylcyanoacetylene Methylformate Propenal Nineatoms Acetamide Cyanohexatriyne Cyanotriacetylene Dimethylether Ethanol Methyldiacetylene Octatetraynylradical Propene Propionitrile Tenatomsormore Acetone Benzene Benzonitrile Buckminsterfullerene(C60,C60+,fullerene,buckyball) C70fullerene Cyanodecapentayne Cyanopentaacetylene Cyanotetra-acetylene Ethyleneglycol Ethylformate Methylacetate Methyl-cyano-diacetylene Methyltriacetylene Propanal n-Propylcyanide Pyrimidine Deuteratedmolecules Ammonia Ammoniumion Formaldehyde Formylradical Heavywater Hydrogencyanide Hydrogendeuteride Hydrogenisocyanide Methylacetylene N2D+ Trihydrogencation Unconfirmed 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