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Aceticacid
FromWikipedia,thefreeencyclopedia

Aceticacid/sitk/,systematicallynamedethanoicacid Aceticacid
/nok/,isacolourlessliquidorganiccompoundwiththe
chemicalformulaCH3COOH(alsowrittenasCH3CO2Hor
C2H4O2).Whenundiluted,itissometimescalledglacialacetic
acid.Vinegarisroughly39%aceticacidbyvolume,making
aceticacidthemaincomponentofvinegarapartfromwater.
Aceticacidhasadistinctivesourtasteandpungentsmell.In
additiontohouseholdvinegar,itismainlyproducedasa
precursortopolyvinylacetateandcelluloseacetate.Althoughit
isclassifiedasaweakacid,concentratedaceticacidiscorrosive
andcanattacktheskin.

Aceticacidisthesecondsimplestcarboxylicacid(afterformic
acid)andconsistsoftwosmallfunctionalgroups,anacetyl
group(sometimessymbolizedasAc)andahydroxylgroup
(AcOH)itcanalsobeviewedasamethylgroupandacarboxyl
grouplinked.Itisanimportantchemicalreagentandindustrial
chemical,usedprimarilyintheproductionofcelluloseacetate
forphotographicfilm,polyvinylacetateforwoodglue,and
syntheticfibresandfabrics.Inhouseholds,dilutedaceticacidis
oftenusedindescalingagents.Inthefoodindustry,aceticacid
iscontrolledbythefoodadditivecodeE260asanacidity
regulatorandasacondiment.Asafoodadditiveitisapproved
forusageinmanycountries,includingCanada,[6]theEuropean
Union,[7]theUnitedStates,[8]AustraliaandNewZealand.[9]In
biochemistry,theacetylgroup,derivedfromaceticacid,is
fundamentaltoallformsoflife.WhenboundtocoenzymeA,it
iscentraltothemetabolismofcarbohydratesandfats.

Theglobaldemandforaceticacidisabout6.5millionmetric
tonsperyear(Mt/a),ofwhichapproximately1.5Mt/aismetby
recyclingtheremainderismanufacturedfrompetrochemical
feedstock.[10]Asachemicalreagent,biologicalsourcesofacetic Names
acidareofinterest,butgenerallycannotcompeteeconomically. PreferredIUPACname
Vinegarismostlydiluteaceticacid,oftenproducedby Aceticacid
fermentationandsubsequentoxidationofethanol. SystematicIUPACname
Ethanoicacid
Othernames
Contents Vinegar(whendilute)Hydrogenacetate
Methanecarboxylicacid[1][2]
1 Nomenclature
2 Properties Identifiers
2.1 Acidity CASNumber 64197(http://www.commonc
2.2 Structure hemistry.org/ChemicalDetail.as

2.3 Solventproperties
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2.3 Solventproperties px?ref=64197)

2.4 Biochemistry
3 Production 3Dmodel(Jmol) Interactiveimage(http://chema
3.1 Methanolcarbonylation pps.stolaf.edu/jmol/jmol.php?m
3.2 Acetaldehydeoxidation odel=CC%28O%29%3DO)
3.3 Ethyleneoxidation 3DMet B00009(http://www.3dmet.dn
3.4 Oxidativefermentation
a.affrc.go.jp/cgi/show_data.ph
3.5 Anaerobicfermentation
4 Uses p?acc=B00009)
4.1 Vinylacetatemonomer Abbreviations AcOH
4.2 Esterproduction BeilsteinReference 506007
4.3 Aceticanhydride
4.4 Useassolvent ChEBI CHEBI:15366(https://www.eb
4.5 Medicaluse i.ac.uk/chebi/searchId.do?chebi
4.6 Foods Id=15366)
5 Reactions
5.1 Organicchemistry ChEMBL ChEMBL539(https://www.ebi.
5.2 Reactionswithinorganiccompounds ac.uk/chembldb/index.php/com
5.3 Otherderivatives pound/inspect/ChEMBL539)
6 History
ChemSpider 171(http://www.chemspider.co
6.1 Interstellarmedium
7 Healtheffectsandsafety m/ChemicalStructure.171.htm
8 Seealso l)
9 References DrugBank DB03166(https://www.drugba
10 Externallinks
nk.ca/drugs/DB03166)
ECHAInfoCard 100.000.528(https://echa.europ

Nomenclature a.eu/substanceinformation//su
bstanceinfo/100.000.528)
Thetrivialnameaceticacidisthemostcommonlyusedand ECNumber 2005807
preferredIUPACname.Thesystematicnameethanoicacid,a Enumber E260(preservatives)
validIUPACname,isconstructedaccordingtothesubstitutive GmelinReference 1380
nomenclature.[11]Thenameaceticacidderivesfromacetum,the IUPHAR/BPS 1058(http://www.guidetophar
Latinwordforvinegar,andisrelatedtothewordaciditself.
macology.org/GRAC/LigandDi
Glacialaceticacidisanameforwaterfree(anhydrous)acetic splayForward?tab=summary&li
acid.SimilartotheGermannameEisessig(icevinegar),the gandId=1058)
namecomesfromtheicelikecrystalsthatformslightlybelow KEGG D00010(http://www.kegg.jp/en
roomtemperatureat16.6C(61.9F)(thepresenceof0.1%
try/D00010)
waterlowersitsmeltingpointby0.2C).[12]
MeSH Acetic+acid(https://www.nlm.
AcommonabbreviationforaceticacidisAcOH,whereAc nih.gov/cgi/mesh/2014/MB_cg
i?mode=&term=Acetic+acid)
standsfortheacetylgroupCH3C(=O).Acetate(CH3COO )
isabbreviatedAcO.TheAcisnottobeconfusedwiththe PubChem 176(https://pubchem.ncbi.nlm.
nih.gov/compound/176)
abbreviationforthechemicalelementactinium.[13]Tobetter
reflectitsstructure,aceticacidisoftenwrittenasCH3C(O)OH, RTECSnumber AF1225000
CH3C(=O)OH,CH3COOH,andCH3CO2H.Inthecontextof UNII Q40Q9N063P(http://fdasis.nl
acidbasereactions,theabbreviationHAcissometimesused,[14] m.nih.gov/srs/srsdirect.jsp?regn
whereAcinthiscaseisasymbolforacetate(ratherthanacetyl). o=Q40Q9N063P)
UNnumber 2789

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+ InChI
AcetateistheionresultingfromlossofH fromaceticacid.The
nameacetatecanalsorefertoasaltcontainingthisanion,oran SMILES
esterofaceticacid.[15] Properties
Chemicalformula C2H4O2
Properties Molarmass 60.05gmol1

Acidity Appearance Colourlessliquid

Odor Pungent/Vinegarlike
Thehydrogencentreinthecarboxylgroup(COOH)in Density 1.049gcm3
carboxylicacidssuchasaceticacidcanseparatefromthe
moleculebyionization: Meltingpoint 16to17C61to62F289
to290K
CH3CO2HCH3CO2+H+ Boilingpoint 118to119C244to246F
391to392K
Becauseofthisreleaseoftheproton(H+),aceticacidhasacidic Solubilityinwater Miscible
character.Aceticacidisaweakmonoproticacid.Inaqueous logP 0.322
solution,ithasapKavalueof4.76.[16]Itsconjugatebaseis
Acidity(pKa) 4.76[3]
acetate(CH3COO).A1.0Msolution(abouttheconcentration
Basicity(pKb) 9.24(basicityofacetateion)
ofdomesticvinegar)hasapHof2.4,indicatingthatmerely
Magnetic 31.54106cm3/mol
0.4%oftheaceticacidmoleculesaredissociated.[17] susceptibility()
Refractiveindex 1.371
(nD)
Viscosity 1.22mPas
Dipolemoment 1.74D
Thermochemistry
Structure
Specific 123.1JK1mol1
heatcapacity(C)
Insolidaceticacid,themoleculesformpairs(dimers),being
Stdmolar 158.0JK1mol1
connectedbyhydrogenbonds.[18]Thedimerscanalsobe
entropy(So298)
detectedinthevapourat120C(248F).Dimersalsooccurin
theliquidphaseindilutesolutionsinnonhydrogenbonding Stdenthalpyof 483.88483.16kJmol1
solvents,andacertainextentinpureaceticacid,[19]butare formation(fHo298)
disruptedbyhydrogenbondingsolvents.Thedissociation Stdenthalpyof 875.50874.82kJmol1
enthalpyofthedimerisestimatedat65.066.0kJ/mol,andthe combustion
dissociationentropyat154157Jmol1K1.[20]Otherlower (cHo298)
carboxylicacidsdimerizeinasimilarfashion.[21] Pharmacology
ATCcode G01AD02(WHO(http://www.
Solventproperties whocc.no/atc_ddd_index/?code
=G01AD02))S02AA10(WHO
Liquidaceticacidisahydrophilic(polar)proticsolvent,similar
(http://www.whocc.no/atc_ddd
toethanolandwater.Withamoderaterelativestaticpermittivity
_index/?code=S02AA10))
(dielectricconstant)of6.2,itdissolvesnotonlypolar
compoundssuchasinorganicsaltsandsugars,butalsonon Hazards
polarcompoundssuchasoilsandelementssuchassulfurand Safetydatasheet See:datapage
iodine.Itreadilymixeswithotherpolarandnonpolarsolvents GHSpictograms
suchaswater,chloroform,andhexane.Withhigheralkanes
(startingwithoctane),aceticacidisnotcompletelymiscible,
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anditsmiscibilitydeclineswithlongernalkanes.[22]The GHSsignalword Danger

solventandmiscibilitypropertiesofaceticacidmakeitauseful GHShazard H226,H314
industrialchemical,forexample,asasolventintheproduction statements
ofdimethylterephthalate.[10] GHSprecautionary P280,P305+351+338,P310
statements

Biochemistry EUclassification
(DSD) C

AtphysiologicalpHs,aceticacidisusuallyfullyionisedto Rphrases R10,R35

acetate.Theacetylgroup,derivedfromaceticacid,is Sphrases (S1/2),S23,S26,S45
fundamentaltoallformsoflife.WhenboundtocoenzymeA,it
NFPA704
iscentraltothemetabolismofcarbohydratesandfats.Unlike 2
longerchaincarboxylicacids(thefattyacids),aceticaciddoes 3 0
notoccurinnaturaltriglycerides.However,theartificial
triglyceridetriacetin(glycerinetriacetate)isacommonfood
additiveandisfoundincosmeticsandtopicalmedicines.[23] Flashpoint 40C(104F313K)
Autoignition 427C(801F700K)
Aceticacidisproducedandexcretedbyaceticacidbacteria, temperature
notablytheAcetobactergenusandClostridiumacetobutylicum. Explosivelimits 416%
Thesebacteriaarefounduniversallyinfoodstuffs,water,and
Lethaldoseorconcentration(LD,LC):
soil,andaceticacidisproducednaturallyasfruitsandother
foodsspoil.Aceticacidisalsoacomponentofthevaginal LD50(median 3.31gkg1,oral(rat)
lubricationofhumansandotherprimates,whereitappearsto dose)

serveasamildantibacterialagent.[24] LC50(median 5620ppm(mouse,1hr)

concentration) 16000ppm(rat,4hr)[5]
Production UShealthexposurelimits(NIOSH):
PEL(Permissible) TWA10ppm(25mg/m3)[4]
Aceticacidisproducedindustriallybothsyntheticallyandby
REL TWA10ppm(25mg/m3)ST
bacterialfermentation.About75%ofaceticacidmadeforusein (Recommended)
thechemicalindustryismadebythecarbonylationofmethanol, 15ppm(37mg/m3)[4]
explainedbelow.[10]Thebiologicalrouteaccountsforonly IDLH(Immediate 50ppm[4]
about10%ofworldproduction,butitremainsimportantforthe danger)
productionofvinegarbecausemanyfoodpuritylawsrequire Relatedcompounds
vinegarusedinfoodstobeofbiologicalorigin.Asof2003 Relatedcarboxylic Formicacid
2005,totalworldwideproductionofvirginaceticacid[25]was acids Propionicacid
estimatedat5Mt/a(milliontonnesperyear),approximatelyhalf Relatedcompounds Acetaldehyde
ofwhichwasproducedintheUnitedStates.European
productionwasapproximately1Mt/aanddeclining,while Acetamide
Japaneseproductionwas0.7Mt/a.Another1.5Mtwere Aceticanhydride
recycledeachyear,bringingthetotalworldmarketto Acetonitrile
Acetylchloride
6.5Mt/a.[26][27]Sincethentheglobalproductionhasincreased Ethanol
to10.7Mt/a(in2010),andfurtherhowever,aslowinginthis Ethylacetate
increaseinproductionispredicted.[28]Thetwobiggest Potassiumacetate
producersofvirginaceticacidareCelaneseandBPChemicals. Sodiumacetate
Thioaceticacid
OthermajorproducersincludeMillenniumChemicals,Sterling
Chemicals,Samsung,Eastman,andSvenskEtanolkemi.[29] Supplementarydatapage
Structureand Refractiveindex(n),
Methanolcarbonylation properties Dielectricconstant(r),etc.

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Mostaceticacidisproducedbymethanolcarbonylation.Inthis Thermodynamic Phasebehaviour

process,methanolandcarbonmonoxidereacttoproduceacetic data solidliquidgas
acidaccordingtotheequation: Spectraldata UV,IR,NMR,MS
Exceptwhereotherwisenoted,dataaregivenfor
materialsintheirstandardstate(at25C[77F],
100kPa).
verify(whatis ?)
Theprocessinvolvesiodomethaneasanintermediate,and
occursinthreesteps.Acatalyst,metalcarbonyl,isneededfor Infoboxreferences
thecarbonylation(step2).[30]

1.CH3OH+HICH3I+H2O
2.CH3I+COCH3COI
3.CH3COI+H2OCH3COOH+HI

Tworelatedprocessesforthecarbonylationofmethanol:therhodiumcatalyzed
Monsantoprocess,andtheiridiumcatalyzedCativaprocess.Thelatterprocessis
greenerandmoreefficient[31]andhaslargelysupplantedtheformerprocess,often
inthesameproductionplants.Catalyticamountsofwaterareusedinboth
processes,buttheCativaprocessrequiresless,sothewatergasshiftreactionis
suppressed,andfewerbyproductsareformed.

Byalteringtheprocessconditions,aceticanhydridemayalsobeproducedonthe Aceticacidcrystals
sameplantusingtherhodiumcatalysts.[32]

Acetaldehydeoxidation

PriortothecommercializationoftheMonsantoprocess,mostaceticacid
wasproducedbyoxidationofacetaldehyde.Thisremainsthesecondmost
importantmanufacturingmethod,althoughitisusuallynotcompetitive Cyclicdimerofaceticaciddashed
withthecarbonylationofmethanol.Theacetaldehydecanbeproducedby greenlinesrepresenthydrogenbonds
hydrationofacetylene.Thiswasthedominanttechnologyintheearly
1900s.[33]

Lightnaphthacomponentsarereadilyoxidizedbyoxygenorevenairtogiveperoxides,whichdecomposeto
produceaceticacidaccordingtothechemicalequation,illustratedwithbutane:

2C4H10+5O24CH3CO2H+2H2O

Suchoxidationsrequiremetalcatalyst,suchasthenaphthenatelsaltsofmanganese,cobalt,andchromium.

Thetypicalreactionisconductedattemperaturesandpressuresdesignedtobeashotaspossiblewhilestill
keepingthebutanealiquid.Typicalreactionconditionsare150C(302F)and55atm.[34]Sideproductsmay
alsoform,includingbutanone,ethylacetate,formicacid,andpropionicacid.Thesesideproductsarealso
commerciallyvaluable,andthereactionconditionsmaybealteredtoproducemoreofthemwhereneeded.
However,theseparationofaceticacidfromthesebyproductsaddstothecostoftheprocess.[35]

Undersimilarconditionsandusingsimilarcatalystsasareusedforbutaneoxidation,theoxygeninairtoproduce
aceticacidcanoxidizeacetaldehyde.[35]

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2CH3CHO+O22CH3CO2H

Usingmoderncatalysts,thisreactioncanhaveanaceticacidyieldgreater
than95%.Themajorsideproductsareethylacetate,formicacid,and
formaldehyde,allofwhichhavelowerboilingpointsthanaceticacidand
arereadilyseparatedbydistillation.[35]

Ethyleneoxidation

AcetaldehydemaybepreparedfromethyleneviatheWackerprocess,and
thenoxidisedasabove.

Inmorerecenttimes,chemicalcompanyShowaDenko,whichopenedan
ethyleneoxidationplantinita,Japan,in1997,commercialisedacheaper
singlestageconversionofethylenetoaceticacid.[36]Theprocessis
catalyzedbyapalladiummetalcatalystsupportedonaheteropolyacidsuch Purificationandconcentrationplant
assilicotungsticacid.Similarprocessusethesamemetalcatalyston foraceticacidin1884
silicotungsticacidandsilica:[37]

C2H4+O2CH3CO2H

Itisthoughttobecompetitivewithmethanolcarbonylationforsmallerplants(100250kt/a),dependingonthe
localpriceofethylene.Theapproachwillbebasedonutilizinganovelselectivephotocatalyticoxidation
technologyfortheselectiveoxidationofethyleneandethanetoaceticacid.Unliketraditionaloxidationcatalysts,
theselectiveoxidationprocesswilluseUVlighttoproduceaceticacidatambienttemperaturesandpressure.

Oxidativefermentation

Formostofhumanhistory,aceticacidbacteriaofthegenusAcetobacterhavemadeaceticacid,intheformof
vinegar.Givensufficientoxygen,thesebacteriacanproducevinegarfromavarietyofalcoholicfoodstuffs.
Commonlyusedfeedsincludeapplecider,wine,andfermentedgrain,malt,rice,orpotatomashes.Theoverall
chemicalreactionfacilitatedbythesebacteriais:

C2H5OH+O2CH3COOH+H2O

AdilutealcoholsolutioninoculatedwithAcetobacterandkeptinawarm,airyplacewillbecomevinegaroverthe
courseofafewmonths.Industrialvinegarmakingmethodsacceleratethisprocessbyimprovingthesupplyof
oxygentothebacteria.[38]

Thefirstbatchesofvinegarproducedbyfermentationprobablyfollowederrorsinthewinemakingprocess.Ifmust
isfermentedattoohighatemperature,acetobacterwilloverwhelmtheyeastnaturallyoccurringonthegrapes.As
thedemandforvinegarforculinary,medical,andsanitarypurposesincreased,vintnersquicklylearnedtouseother
organicmaterialstoproducevinegarinthehotsummermonthsbeforethegrapeswereripeandreadyfor
processingintowine.Thismethodwasslow,however,andnotalwayssuccessful,asthevintnersdidnot
understandtheprocess.[39]

Oneofthefirstmoderncommercialprocesseswasthe"fastmethod"or"Germanmethod",firstpractisedin
Germanyin1823.Inthisprocess,fermentationtakesplaceinatowerpackedwithwoodshavingsorcharcoal.The
alcoholcontainingfeedistrickledintothetopofthetower,andfreshairsuppliedfromthebottombyeither

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naturalorforcedconvection.Theimprovedairsupplyinthisprocesscutthetimetopreparevinegarfrommonths
toweeks.[40]

Nowadays,mostvinegarismadeinsubmergedtankculture,firstdescribedin1949byOttoHromatkaand
HeinrichEbner.[41]Inthismethod,alcoholisfermentedtovinegarinacontinuouslystirredtank,andoxygenis
suppliedbybubblingairthroughthesolution.Usingmodernapplicationsofthismethod,vinegarof15%acetic
acidcanbepreparedinonly24hoursinbatchprocess,even20%in60hourfedbatchprocess.[39]

Anaerobicfermentation

Speciesofanaerobicbacteria,includingmembersofthegenusClostridiumorAcetobacteriumcanconvertsugars
toaceticaciddirectlywithoutcreatingethanolasanintermediate.Theoverallchemicalreactionconductedby
thesebacteriamayberepresentedas:

C6H12O63CH3COOH

Theseacetogenicbacteriaproduceaceticacidfromonecarboncompounds,includingmethanol,carbonmonoxide,
oramixtureofcarbondioxideandhydrogen:

2CO2+4H2CH3COOH+2H2O

ThisabilityofClostridiumtometabolizesugarsdirectly,ortoproduceaceticacidfromlesscostlyinputs,suggests
thatthesebacteriacouldproduceaceticacidmoreefficientlythanethanoloxidizerslikeAcetobacter.However,
ClostridiumbacteriaarelessacidtolerantthanAcetobacter.EventhemostacidtolerantClostridiumstrainscan
producevinegarinconcentrationsofonlyafewpercent,comparedtoAcetobacterstrainsthatcanproducevinegar
inconcentrationsupto20%.Atpresent,itremainsmorecosteffectivetoproducevinegarusingAcetobacter,
ratherthanusingClostridiumandconcentratingit.Asaresult,althoughacetogenicbacteriahavebeenknown
since1940,theirindustrialuseisconfinedtoafewnicheapplications.[42]

Uses
Aceticacidisachemicalreagentfortheproductionofchemicalcompounds.Thelargestsingleuseofaceticacidis
intheproductionofvinylacetatemonomer,closelyfollowedbyaceticanhydrideandesterproduction.The
volumeofaceticacidusedinvinegariscomparativelysmall.[10][27]

Vinylacetatemonomer

Theprimaryuseofaceticacidistheproductionofvinylacetatemonomer(VAM).In2008,thisapplicationwas
estimatedtoconsumeathirdoftheworld'sproductionofaceticacid.[10]Thereactionconsistsofethyleneand
aceticacidwithoxygenoverapalladiumcatalyst,conductedinthegasphase.[43]

2H3CCOOH+2C2H4+O22H3CCOOCH=CH2+2H2O

Vinylacetatecanbepolymerisedtopolyvinylacetateorotherpolymers,whicharecomponentsinpaintsand
adhesives.[43]

Esterproduction

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Themajorestersofaceticacidarecommonlyusedassolventsforinks,paintsandcoatings.Theestersinclude
ethylacetate,nbutylacetate,isobutylacetate,andpropylacetate.Theyaretypicallyproducedbycatalyzed
reactionfromaceticacidandthecorrespondingalcohol:

H3CCOOH+HORH3CCOOR+H2O,(R=ageneralalkylgroup)

Mostacetateesters,however,areproducedfromacetaldehydeusingtheTishchenkoreaction.Inaddition,ether
acetatesareusedassolventsfornitrocellulose,acryliclacquers,varnishremovers,andwoodstains.First,glycol
monoethersareproducedfromethyleneoxideorpropyleneoxidewithalcohol,whicharethenesterifiedwith
aceticacid.Thethreemajorproductsareethyleneglycolmonoethyletheracetate(EEA),ethyleneglycol
monobutyletheracetate(EBA),andpropyleneglycolmonomethyletheracetate(PMA,morecommonlyknownas
PGMEAinsemiconductormanufacturingprocesses,whereitisusedasaresistsolvent).Thisapplication
consumesabout15%to20%ofworldwideaceticacid.Etheracetates,forexampleEEA,havebeenshowntobe
harmfultohumanreproduction.[27]

Aceticanhydride

Theproductofthecondensationoftwomoleculesofaceticacidisaceticanhydride.Theworldwideproductionof
aceticanhydrideisamajorapplication,andusesapproximately25%to30%oftheglobalproductionofacetic
acid.Themainprocessinvolvesdehydrationofaceticacidtogiveketeneat700750C.Keteneisthereafter
reactedwithaceticacidtoobtaintheanhydride:[44]

CH3CO2HCH2=C=O+H2O
CH3CO2H+CH2=C=O(CH3CO)2O

Aceticanhydrideisanacetylationagent.Assuch,itsmajorapplicationisforcelluloseacetate,asynthetictextile
alsousedforphotographicfilm.Aceticanhydrideisalsoareagentfortheproductionofheroinandother
compounds.[44]

Useassolvent

Glacialaceticacidisanexcellentpolarproticsolvent,asnotedabove.Itisfrequentlyusedasasolventfor
recrystallizationtopurifyorganiccompounds.Aceticacidisusedasasolventintheproductionofterephthalic
acid(TPA),therawmaterialforpolyethyleneterephthalate(PET).In2006,about20%ofaceticacidwasusedfor
TPAproduction.[27]

Aceticacidisoftenusedasasolventforreactionsinvolvingcarbocations,suchasFriedelCraftsalkylation.For
example,onestageinthecommercialmanufactureofsyntheticcamphorinvolvesaWagnerMeerwein
rearrangementofcamphenetoisobornylacetatehereaceticacidactsbothasasolventandasanucleophiletotrap
therearrangedcarbocation.[45]

Glacialaceticacidisusedinanalyticalchemistryfortheestimationofweaklyalkalinesubstancessuchasorganic
amides.Glacialaceticacidisamuchweakerbasethanwater,sotheamidebehavesasastrongbaseinthis
medium.Itthencanbetitratedusingasolutioninglacialaceticacidofaverystrongacid,suchasperchloric
acid.[46]

Medicaluse

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Aceticacidisusedaspartofcervicalcancerscreeninginmanyareasinthedevelopingworld.[47]Aceticacidis
appliedtothecervixandifanareaofwhiteappearsafteraboutaminutethetestispositive.[47]

Itisaneffectiveantisepticwhenusedasa1%solution,withbroadspectrumofactivityagainststreptococci,
staphylococci,pseudomonas,enterococciandothers.[48][49][50]Itmaybeanoptionforskininfectionscauseby
pseudomonasresistanttotypicalantibiotics.[51]

Whiledilutedaceticacidisusediniontophoresis,nohighqualityevidencesupportsthistreatmentinrotatorcuff
disease.[52][53]

Asatreatmentforotitisexterna,itisontheWorldHealthOrganization'sListofEssentialMedicines,themost
importantmedicationsneededinabasichealthsystem.[54]

Foods

Vinegaristypically418%aceticacidbymass.Vinegarisuseddirectlyasacondiment,andinthepicklingof
vegetablesandotherfoods.Tablevinegartendstobemorediluted(4%to8%aceticacid),whilecommercialfood
picklingemployssolutionsthataremoreconcentrated.Theamountofaceticacidusedasvinegaronaworldwide
scaleisnotlarge,butisbyfartheoldestandbestknownapplication.[55]

Reactions
Organicchemistry

Aceticacidundergoesthetypicalchemicalreactionsofacarboxylicacid.Upontreatmentwithastandardbase,it
convertstometalacetateandwater.Withstrongbases(e.g.,organolithiumreagents),itcanbedoublydeprotonated
togiveLiCH2CO2Li.Reductionofaceticacidgivesethanol.TheOHgroupisthemainsiteofreaction,as
illustratedbytheconversionofaceticacidtoacetylchloride.Othersubstitutionderivativesincludeacetic
anhydridethisanhydrideisproducedbylossofwaterfromtwomoleculesofaceticacid.Estersofaceticacidcan
likewisebeformedviaFischeresterification,andamidescanbeformed.Whenheatedabove440C(824F),
aceticaciddecomposestoproducecarbondioxideandmethane,ortoproduceketeneandwater:[56][57][58]

CH3COOHCH4+CO2
CH3COOHCH2CO+H2O

Reactionswithinorganiccompounds

Aceticacidismildlycorrosivetometalsincludingiron,magnesium,andzinc,forminghydrogengasandsalts
calledacetates:

Mg+2CH3COOH(CH3COO)2Mg+H2

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Becausealuminiumformsapassivatingacidresistantfilmofaluminiumoxide,aluminiumtanksareusedto
transportaceticacid.Metalacetatescanalsobepreparedfromaceticacidandanappropriatebase,asinthe
popular"bakingsoda+vinegar"reaction:

NaHCO3+CH3COOHCH3COONa+CO2+H2O

Acolourreactionforsaltsofaceticacidisiron(III)chloridesolution,whichresultsinadeeplyredcolourthat
disappearsafteracidification.[59]Amoresensitivetestuseslanthanumnitratewithiodineandammoniatogivea
bluesolution.[60]Acetateswhenheatedwitharsenictrioxideformcacodyloxide,whichcanbedetectedbyits
malodorousvapours.[61]

Otherderivatives

Organicorinorganicsaltsareproducedfromaceticacid,including:

Sodiumacetate,usedinthetextileindustryandasafoodpreservative(E262).
Copper(II)acetate,usedasapigmentandafungicide.
Aluminiumacetateandiron(II)acetateusedasmordantsfordyes.
Palladium(II)acetate,usedasacatalystfororganiccouplingreactionssuchastheHeckreaction.
Silveracetate,usedasapesticide.

Substitutedaceticacidsproducedinclude:

Chloroaceticacid(monochloroaceticacid,MCA),dichloroaceticacid(consideredabyproduct),and
trichloroaceticacid.MCAisusedinthemanufactureofindigodye.
Bromoaceticacid,whichisesterifiedtoproducethereagentethylbromoacetate.
Trifluoroaceticacid,whichisacommonreagentinorganicsynthesis.

Amountsofaceticacidusedintheseotherapplicationstogether(apartfromTPA)accountforanother510%of
aceticaciduseworldwide.Theseapplicationsare,however,notexpectedtogrowasmuchasTPAproduction.[27]

History
Vinegarwasknownearlyincivilizationasthenaturalresultofexposureofbeerandwinetoair,becauseacetic
acidproducingbacteriaarepresentglobally.Theuseofaceticacidinalchemyextendsintothe3rdcenturyBC,
whentheGreekphilosopherTheophrastusdescribedhowvinegaractedonmetalstoproducepigmentsusefulin
art,includingwhitelead(leadcarbonate)andverdigris,agreenmixtureofcoppersaltsincludingcopper(II)
acetate.AncientRomansboiledsouredwinetoproduceahighlysweetsyrupcalledsapa.Sapathatwasproduced
inleadpotswasrichinleadacetate,asweetsubstancealsocalledsugarofleadorsugarofSaturn,which
contributedtoleadpoisoningamongtheRomanaristocracy.[62]

Inthe16thcenturyGermanalchemistAndreasLibaviusdescribedtheproductionofacetonefromthedry
distillationofleadacetate,ketonicdecarboxylation.Thepresenceofwaterinvinegarhassuchaprofoundeffecton
aceticacid'spropertiesthatforcenturieschemistsbelievedthatglacialaceticacidandtheacidfoundinvinegar
weretwodifferentsubstances.FrenchchemistPierreAdetprovedthemidentical.[62][63]

In1845GermanchemistHermannKolbesynthesisedaceticacidfrominorganiccompoundsforthefirsttime.This
reactionsequenceconsistedofchlorinationofcarbondisulfidetocarbontetrachloride,followedbypyrolysisto
tetrachloroethyleneandaqueouschlorinationtotrichloroaceticacid,andconcludedwithelectrolyticreductionto
aceticacid.[64]

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By1910,mostglacialaceticacidwasobtainedfromthepyroligneousliquor,a
productofthedistillationofwood.Theaceticacidwasisolatedbytreatmentwith
milkoflime,andtheresultingcalciumacetatewasthenacidifiedwithsulfuricacid
torecoveraceticacid.Atthattime,Germanywasproducing10,000tonsofglacial
aceticacid,around30%ofwhichwasusedforthemanufactureofindigo
dye.[62][65]

Becausebothmethanolandcarbonmonoxidearecommodityrawmaterials,
methanolcarbonylationlongappearedtobeattractiveprecursorstoaceticacid.
HenriDreyfusatBritishCelanesedevelopedamethanolcarbonylationpilotplant
asearlyas1925.[66]However,alackofpracticalmaterialsthatcouldcontainthe
corrosivereactionmixtureatthehighpressuresneeded(200atmormore)
Crystallisedaceticacid. discouragedcommercializationoftheseroutes.Thefirstcommercialmethanol
carbonylationprocess,whichusedacobaltcatalyst,wasdevelopedbyGerman
chemicalcompanyBASFin1963.In1968,arhodiumbasedcatalyst(cis
[Rh(CO)2I2])wasdiscoveredthatcouldoperateefficientlyatlowerpressurewithalmostnobyproducts.US
chemicalcompanyMonsantoCompanybuiltthefirstplantusingthiscatalystin1970,andrhodiumcatalyzed
methanolcarbonylationbecamethedominantmethodofaceticacidproduction(seeMonsantoprocess).Inthelate
1990s,thechemicalscompanyBPChemicalscommercialisedtheCativacatalyst([Ir(CO)2I2]),whichis
promotedbyiridium[67]forgreaterefficiency.ThisiridiumcatalyzedCativaprocessisgreenerandmore
efficient[31]andhaslargelysupplantedtheMonsantoprocess,ofteninthesameproductionplants.

Interstellarmedium

Interstellaraceticacidwasdiscoveredin1996byateamledbyDavidMehringer[68]usingtheformerBerkeley
IllinoisMarylandAssociationarrayattheHatCreekRadioObservatoryandtheformerMillimeterArraylocated
attheOwensValleyRadioObservatory.ItwasfirstdetectedintheSagittariusB2Northmolecularcloud(also
knownastheSgrB2LargeMoleculeHeimatsource).Aceticacidhasthedistinctionofbeingthefirstmolecule
discoveredintheinterstellarmediumusingsolelyradiointerferometersinallpreviousISMmoleculardiscoveries
madeinthemillimetreandcentimetrewavelengthregimes,singledishradiotelescopeswereatleastpartly
responsibleforthedetections.[68]

Healtheffectsandsafety
Concentratedaceticacidiscorrosivetoskinandmustthereforebehandledwithappropriatecaretoavoidskin
burns,permanenteyedamage,andirritationtothemucousmembranes.[69][70]Theseburnsorblistersmaynot
appearuntilhoursafterexposure.Latexglovesoffernoprotection,sospeciallyresistantgloves,suchasthose
madeofnitrilerubber,arewornwhenhandlingthecompound.

Prolongedskincontactwithglacialaceticacidmayresultintissuedestruction.Inhalationexposure(eighthours)to
aceticacidvapoursat10ppmcanproducesomeirritationofeyes,nose,andthroatat100ppmmarkedlung
irritationandpossibledamagetolungs,eyes,andskinmayresult.Vapourconcentrationsof1,000ppmcause
markedirritationofeyes,noseandupperrespiratorytractandcannotbetolerated.Thesepredictionswerebasedon
animalexperimentsandindustrialexposure.Skinsensitizationtoaceticacidisrare,buthasoccurred.

Ithasbeenreportedthat,in12workersexposedfortwoormoreyearstoaceticacidairborneaverage
concentrationof51ppm(estimated),producedsymptomsofconjunctiveirritation,upperrespiratorytract
irritation,andhyperkeratoticdermatitis.Exposureto50ppmormoreisintolerabletomostpersonsandresultsin

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intensivelacrimationandirritationoftheeyes,nose,andthroat,withpharyngealoedemaandchronicbronchitis.
Unacclimatisedhumansexperienceextremeeyeandnasalirritationatconcentrationsinexcessof25ppm,and
conjunctivitisfromconcentrationsbelow10ppmhasbeenreported.Inastudyoffiveworkersexposedforseven
to12yearstoconcentrationsof80to200ppmatpeaks,theprincipalfindingswereblackeningandhyperkeratosis
oftheskinofthehands,conjunctivitis(butnocornealdamage),bronchitisandpharyngitis,anderosionofthe
exposedteeth(incisorsandcanines).[71]

Thehazardsofsolutionsofaceticaciddependontheconcentration.ThefollowingtableliststheEUclassification
ofaceticacidsolutions:[72]

Concentration
Molarity Classification RPhrases
byweight
1025% 1.674.16mol/L Irritant(Xi) R36/38
2590% 4.1614.99mol/L Corrosive(C) R34
>90% >14.99mol/L Corrosive(C)Flammable(F) R10,R35

Solutionsatmorethan25%aceticacidarehandledinafumehoodbecauseofthepungent,corrosivevapour.
Diluteaceticacid,intheformofvinegar,ispracticallyharmless.However,ingestionofstrongersolutionsis
dangeroustohumanandanimallife.Itcancauseseveredamagetothedigestivesystem,andapotentiallylethal
changeintheacidityoftheblood.

Duetoincompatibilities,itisrecommendedtokeepaceticacidawayfromchromicacid,ethyleneglycol,nitric
acid,perchloricacid,permanganates,peroxidesandhydroxyls.[73]

Concentratedaceticacidcanbeignitedonlywithdifficultyatstandardtemperatureandpressure,butbecomesa
flammableriskintemperaturesgreaterthan39C(102F),andcanformexplosivemixtureswithairathigher
temperatures(explosivelimits:5.416%).

Seealso
Aceticacid(datapage)
Acetylgroup,theCH3COgroup
Acidsinwine

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Externallinks
InternationalChemicalSafetyCard0363(http://www.inchem.org/do
Lookupaceticin
cuments/icsc/icsc/eics0363.htm)
Wiktionary,thefree
NationalPollutantInventoryAceticacidfactsheet(http://www.npi. dictionary.
gov.au/substances/aceticacid/index.html)
NIOSHPocketGuidetoChemicalHazards(http://www.cdc.gov/nios
WikimediaCommonshas
h/npg/npgd0002.html)
mediarelatedtoAceticacid.
Methodforsamplingandanalysis(http://www.cdc.gov/niosh/docs/20
03154/pdfs/1603.pdf)
29CFR1910.1000,TableZ1(https://www.osha.gov/pls/oshaweb/owadisp.show_document?p_table=STAN
DARDS&p_id=9992)(USPermissibleexposurelimits)
ChemSubOnline:Aceticacid(http://chemsub.online.fr/name/Acetic_acid.html)
Calculationofvaporpressure(http://ddbonline.ddbst.de/AntoineCalculation/AntoineCalculationCGI.exe?co
mponent=Acetic+acid),liquiddensity(http://ddbonline.ddbst.de/DIPPR105DensityCalculation/DIPPR105C
alculationCGI.exe?component=Acetic+acid),dynamicliquidviscosity(http://ddbonline.ddbst.de/VogelCalc
ulation/VogelCalculationCGI.exe?component=Acetic+acid),surfacetension(http://ddbonline.ddbst.de/DIPP
R106SFTCalculation/DIPPR106SFTCalculationCGI.exe?component=Acetic+acid)ofaceticacid
Aceticacidboundtoproteins(http://www.ebi.ac.uk/pdbesrv/PDBeXplore/ligand/?ligand=ACT)inthePDB
SwedishChemicalsAgency.InformationsheetAceticAcid(https://web.archive.org/web/2015020706543
4/http://apps.kemi.se/flodessok/floden/kemamne_eng/attiksyra_eng.htm)
ProcessFlowsheetofAceticacidProductionbytheCarbonylationofMethanol(http://www.inclusivescien
ceengineering.com/processesformanufacturingaceticacid/aceticacid/)

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