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Benzoicacid
FromWikipedia,thefreeencyclopedia

Benzoicacid/bnzo.k/,C7H6O2(or

Benzoicacid

C6H5COOH),isacolorlesscrystalline
solidandasimplearomaticcarboxylic
acid.Thenameisderivedfromgum
benzoin,whichwasforalongtimeits
onlyknownsource.Benzoicacid
occursnaturallyinmanyplants[8]and
itservesasanintermediateinthe
biosynthesisofmanysecondary
metabolites.Saltsofbenzoicacidare
usedasfoodpreservativesandbenzoic
acidisanimportantprecursorforthe
industrialsynthesisofmanyother
organicsubstances.Thesaltsand
estersofbenzoicacidareknownas
benzoates/bnzo.et/.

Benzoicacidcrystals

Contents

IUPACname
Benzoicacid

1History

Othernames

2Production
2.1Industrial
preparations

CarboxybenzeneE210DracylicacidPhenylmethanoicacid
Benzenecarboxylicacid

2.2Laboratorysynthesis

Identifiers

2.2.1By

CASnumber 65850

hydrolysis

PubChem

2.2.2From
benzaldehyde

243

ChemSpider 238
UNII

8SKN0B0MIM

ECnumber

2006182

DrugBank

DB03793

alcohol

KEGG

D00038

2.2.5Frombenzyl

MeSH

benzoic+acid

chloride

ChEBI

CHEBI:30746

ChEMBL

CHEMBL541

RTECS
number

DG0875000

Beilstein
Reference

636131

2.2.3From
bromobenzene
2.2.4Frombenzyl

2.2.6Historical
preparation
3Uses
3.1Precursorto
plasticizers

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plasticizers
3.2Precursortosodium
benzoateandrelated
preservatives
3.3Medicinal

Gmelin
Reference

2946

3DMet

B00053

Jmol3D
images

Image1(http://chemapps.stolaf.edu/jmol/jmol.php?
model=O%3DC%28O%29c1ccccc1)
Image2(http://chemapps.stolaf.edu/jmol/jmol.php?
model=c1ccc%28cc1%29C%28%3DO%29O)

3.4Benzoylchloride
3.5Nicheand

SMILES

laboratoryuses

InChI

4Biologyandhealtheffects

Properties

5Reactions
5.1Aromaticring

Molecular
formula

C7H6O2

5.2Carboxylgroup

Molarmass 122.12gmol1

6References

Appearance Colorlesscrystallinesolid

7Externallinks

Odor

faint,pleasantodor

Density

1.2659g/cm3(15C)
1.0749g/cm3(130C)[1]

History
Benzoicacidwasdiscoveredinthe
sixteenthcentury.Thedrydistillation
ofgumbenzoinwasfirstdescribedby
Nostradamus(1556),andthenby
AlexiusPedemontanus(1560)and
BlaisedeVigenre(1596).[9]
Pioneerworkin1830througha
varietyofexperiencesbasedon
amygdalin,obtainedfrombitter
almonds(thefruitofPrunusdulcis)oil
byPierreRobiquetandAntoine
BoutronCharlard,twoFrench
chemists,hadproducedbenzaldehyde
[10]buttheyfailedinworkingouta
properinterpretationofthestructureof
amygdalinthatwouldaccountforit,
andthusmissedtheidentificationof
thebenzoylradicalC7H5O.Thislast
stepwasachievedsomefewmonths
later(1832)byJustusvonLiebigand
FriedrichWhler,whodeterminedthe
compositionofbenzoicacid.[11]These
latteralsoinvestigatedhowhippuric
acidisrelatedtobenzoicacid.

Melting
point

122.41C(252.34F395.56K)[5]

Boilingpoint 249.2C(480.6F522.3K)[6]
370C(698F643K)
decomposes[1]
Solubilityin 1.7g/L(0C)
water
2.7g/L(18C)
3.44g/L(25C)
5.51g/L(40C)
21.45g/L(75C)
56.31g/L(100C)[1][2]
Solubility

solubleinacetone,benzene,CCl4,CHCl3,alcohol,ethyl
ether,hexane,phenyls,liquidammonia,acetates

Solubilityin 30g/100g(18C)
methanol
32.1g/100g(13C)
71.5g/100g(23C)[1]
Solubilityin 25.4g/100g(18C)
ethanol
47.1g/100g(15C)
52.4g/100g(19.2C)
55.9g/100g(23C)[1]
Solubilityin 54.2g/100g(20C)[1]
acetone
Solubilityin 4.22g/100g(25C)[1]
oliveoil
Solubilityin 55.3g/100g(25C)[1]

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In1875Salkowskidiscoveredthe
antifungalabilitiesofbenzoicacid,
whichwasusedforalongtimeinthe
preservationofbenzoatecontaining
cloudberryfruits.[12]

1,4Dioxane

Itisalsooneofthechemical
compoundsfoundincastoreum.This
compoundisgatheredfromthebeaver
plantfood.[13]

Acidity(pKa) 4.202[4]

logP

1.87

Vapor
pressure

0.16Pa(25C)
0.19kPa(100C)
22.6kPa(200C)[3]

Refractive
index(nD)

1.5397(20C)
1.504(132C)[1]

Viscosity

1.26mPa(130C)

Production
Industrialpreparations
Benzoicacidisproduced
commerciallybypartialoxidationof
toluenewithoxygen.Theprocessis
catalyzedbycobaltormanganese
naphthenates.Theprocessusescheap
rawmaterials,andproceedsinhigh
yield.

Structure
Crystal
structure

Monoclinic

Molecular
shape

planar

Dipole
moment

1.72DinDioxane
Thermochemistry

Specific
146.7J/molK[3]
heatcapacity
C
Stdmolar
entropy
So298

U.S.productioncapacityisestimated
tobe126,000tonnesperyear(139,000
tons),muchofwhichisconsumed
domesticallytoprepareother
industrialchemicals.

Laboratorysynthesis
Benzoicacidischeapandreadily
available,sothelaboratorysynthesis
ofbenzoicacidismainlypracticedfor
itspedagogicalvalue.Itisacommon
undergraduatepreparation.
Benzoicacidcanbepurifiedby
recrystallizationfromwaterbecauseof
itshighsolubilityinhotwaterand
poorsolubilityincoldwater.The
avoidanceoforganicsolventsforthe
recrystallizationmakesthis
experimentparticularlysafe.[14]The
solubilityofbenzoicacidinover40
http://en.wikipedia.org/wiki/Benzoic_acid

167.6J/molK[1]

Stdenthalpy 385.2kJ/mol[1]
of
formation
fHo298
Stdenthalpy 3228kJ/mol[3]
of
combustion
cHo298
Hazards
MSDS

JTBaker
(http://hazard.com/msds/mf/baker/baker/files/b1356.htm)

GHS
pictograms
GHSsignal
word

[7]

Danger

GHShazard H318, H335[7]

statements
GHS
P261, P280, P305+351+338[7]
precautionary
statements
EUIndex

Notlisted
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solventswithreferencestooriginal
sourcescanbefoundaspartofthe
OpenNotebookScienceChallenge.[15]
Byhydrolysis

BenzoicacidWikipedia,thefreeencyclopedia

EU
classification

Xi

Rphrases

R37,R41

Sphrases

S26,S39

Mainhazards Irritant

Likeothernitrilesandamides,
benzonitrileandbenzamidecanbe
hydrolyzedtobenzoicacidorits
conjugatebaseinacidorbasic
conditions.

NFPA704

Frombenzaldehyde

Autoignition 571C(1,060F844K)[6]
temperature

Thebaseinduceddisproportionation
ofbenzaldehyde,theCannizzaro
reaction,affordsequalamountsof
benzoateandbenzylalcoholthelatter
canberemovedbydistillation.

LD50

2
Flashpoint

121.5C(250.7F394.6K)[6]

1700mg/kg(rat,oral)
Relatedcompounds

Related
carboxylic
acids

Hydroxybenzoicacids
Aminobenzoicacids,
Nitrobenzoicacids,
Phenylaceticacid

Related
compounds

Benzaldehyde,
Benzylalcohol,
Benzoylchloride,
Benzylamine,
Benzamide

Exceptwherenotedotherwise,dataaregivenformaterialsintheir
standardstate(at25C(77F),100kPa)

(verify)(whatis: / ?)
Infoboxreferences

Frombromobenzene
Bromobenzenecanbeconvertedtobenzoicacidby"carbonation"oftheintermediatephenylmagnesium
bromide.[16]ThissynthesisoffersaconvenientexerciseforstudentstocarryoutaGrignardreaction,an
importantclassofcarboncarbonbondformingreactioninorganicchemistry.[17][18]
Frombenzylalcohol
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Benzylalcoholisrefluxedwithpotassiumpermanganateorotheroxidizingreagentsinwater.The
mixtureishotfilteredtoremovemanganesedioxideandthenallowedtocooltoaffordbenzoicacid.
Frombenzylchloride
BenzoicacidcanbepreparedbyoxidationofbenzylchlorideinthepresenceofalkalineKMnO4:
C6H5CH2Cl+2KOH+2[O]C6H5COOH+KCl+H2O
Historicalpreparation
Thefirstindustrialprocessinvolvedthereactionofbenzotrichloride(trichloromethylbenzene)with
calciumhydroxideinwater,usingironorironsaltsascatalyst.Theresultingcalciumbenzoateis
convertedtobenzoicacidwithhydrochloricacid.Theproductcontainssignificantamountsof
chlorinatedbenzoicacidderivatives.Forthisreason,benzoicacidforhumanconsumptionwasobtained
bydrydistillationofgumbenzoin.Foodgradebenzoicacidisnowproducedsynthetically.

Uses
Benzoicacidismainlyconsumedintheproductionofphenolbyoxidativedecarboxylationat
300400C:[19]
C6H5CO2H+1/2O2C6H5OH+CO2
Thetemperaturerequiredcanbeloweredto200Cbytheadditionofcatalyticamountsofcopper(II)
salts.Thephenolcanbeconvertedtocyclohexanol,whichisastartingmaterialfornylonsynthesis.

Precursortoplasticizers
Benzoateplasticizers,suchastheglycol,diethylenegylcol,andtriethyleneglycolesters,areobtained
bytransesterificationofmethylbenzoatewiththecorrespondingdiol.Alternativelythesespeciesarise
bytreatmentofbenzoylchloridewiththediol.Theseplasticizersareusedsimilarlytothosederivedfrom
terephthalicacidester.

Precursortosodiumbenzoateandrelatedpreservatives
Benzoicacidanditssaltsareusedasafoodpreservatives,representedbytheEnumbersE210,E211,
E212,andE213.Benzoicacidinhibitsthegrowthofmold,yeast[20]andsomebacteria.Itiseitheradded
directlyorcreatedfromreactionswithitssodium,potassium,orcalciumsalt.Themechanismstartswith
theabsorptionofbenzoicacidintothecell.IftheintracellularpHchangesto5orlower,theanaerobic
fermentationofglucosethroughphosphofructokinaseisdecreasedby95%.Theefficacyofbenzoicacid
andbenzoateisthusdependentonthepHofthefood.[21]Acidicfoodandbeveragelikefruitjuice(citric
acid),sparklingdrinks(carbondioxide),softdrinks(phosphoricacid),pickles(vinegar)orother
acidifiedfoodarepreservedwithbenzoicacidandbenzoates.
Typicallevelsofuseforbenzoicacidasapreservativeinfoodarebetween0.050.1%.Foodsinwhich
benzoicacidmaybeusedandmaximumlevelsforitsapplicationarecontrolledbyinternationalfood
law.[22][23]
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Concernhasbeenexpressedthatbenzoicacidanditssaltsmayreactwithascorbicacid(vitaminC)in
somesoftdrinks,formingsmallquantitiesofbenzene.[24]

Medicinal
BenzoicacidisaconstituentofWhitfield'sointmentwhichisusedforthetreatmentoffungalskin
diseasessuchastinea,ringworm,andathlete'sfoot.[25][26]Astheprincipalcomponentofbenzoinresin,
benzoicacidisalsoamajoringredientinbothtinctureofbenzoinandFriar'sbalsam.Suchproducts
havealonghistoryofuseastopicalantisepticsandinhalantdecongestants.
Benzoicacidwasusedasanexpectorant,analgesic,andantisepticintheearly20thcentury.[27]

Benzoylchloride
Benzoicacidisaprecursortobenzoylchloride,C6H5C(O)Clbytreatmentwiththionylchloride,
phosgeneoroneofthechloridesofphosphorus.isanimportantstartingmaterialforseveralbenzoicacid
derivateslikebenzylbenzoate,whichisusedinartificialflavoursandinsectrepellents.

Nicheandlaboratoryuses
Inteachinglaboratories,benzoicacidisacommonstandardforcalibratingabombcalorimeter.[28]

Biologyandhealtheffects
Benzoicacidisrelativelynontoxic.Itisexcretedashippuricacid.[29]Benzoicacidismetabolizedby
butyrateCoAligaseintoanintermediateproduct,benzoylCoA,[30]whichisthenmetabolizedby
glycineNacyltransferaseintohippuricacid.[31]
Benzoicacidoccursnaturallyasdoitsestersinmanyplantandanimalspecies.Appreciableamounts
havebeenfoundinmostberries(around0.05%).RipefruitsofseveralVacciniumspecies(e.g.,
cranberry,V.vitismacrocarponbilberry,V.myrtillus)containasmuchas0.030.13%freebenzoic
acid.BenzoicacidisalsoformedinapplesafterinfectionwiththefungusNectriagalligena.Among
animals,benzoicacidhasbeenidentifiedprimarilyinomnivorousorphytophageousspecies,e.g.,in
visceraandmusclesoftheRockPtarmigan(Lagopusmuta)aswellasinglandsecretionsofmale
muskoxen(Ovibosmoschatus)orAsianbullelephants(Elephasmaximus).[32]
Gumbenzoincontainsupto20%ofbenzoicacidand40%benzoicacidesters.[33]
Cryptanaerobacterphenolicusisabacteriumspeciesthatproducesbenzoatefromphenolvia4
hydroxybenzoate[34]
Benzoicacidispresentaspartofhippuricacid(Nbenzoylglycine)inurineofmammals,especially
herbivores(Gr.hippos=horseouron=urine).Humansproduceabout0.44g/Lhippuricacidperdayin
theirurine,andifthepersonisexposedtotolueneorbenzoicacid,itcanriseabovethatlevel.[35]
Forhumans,theWorldHealthOrganization'sInternationalProgrammeonChemicalSafety(IPCS)
suggestsaprovisionaltolerableintakewouldbe5mg/kgbodyweightperday.[32]Catshavea
significantlylowertoleranceagainstbenzoicacidanditssaltsthanratsandmice.Lethaldoseforcats
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canbeaslowas300mg/kgbodyweight.[36]TheoralLD50forratsis3040mg/kg,formiceitis1940
2263mg/kg.[32]
InTaipei,Taiwan,acityhealthsurveyin2010foundthat30%ofdriedandpickledfoodproductshad
toomuchbenzoicacid,whichmayaffecttheliverandkidney,[37]alongwithmoreseriousissueslike
excessivecyclamate.

Reactions
Reactionsofbenzoicacidcanoccurateitherthearomaticringoratthecarboxylgroup:

Aromaticring

Electrophilicaromaticsubstitutionreactionwilltakeplacemainlyin3positionduetotheelectron
withdrawingcarboxylicgroupi.e.benzoicacidismetadirecting.
Thesecondsubstitutionreaction(ontheright)isslowerbecausethefirstnitrogroupisdeactivating.[38]
Conversely,ifanactivatinggroup(electrondonating)wasintroduced(e.g.,alkyl),asecondsubstitution
reactionwouldoccurmorereadilythanthefirstandthedisubstitutedproductmightaccumulatetoa
significantextent.

Carboxylgroup
Allthereactionsmentionedforcarboxylicacidsarealsopossibleforbenzoicacid.
Benzoicacidestersaretheproductoftheacidcatalysedreactionwithalcohols.
Benzoicacidamidesaremoreeasilyavailablebyusingactivatedacidderivatives(suchasbenzoyl
chloride)orbycouplingreagentsusedinpeptidesynthesislikeDCCandDMAP.
Themoreactivebenzoicanhydrideisformedbydehydrationusingaceticanhydrideor
phosphoruspentoxide.
Highlyreactiveacidderivativessuchasacidhalidesareeasilyobtainedbymixingwith
halogenationagentslikephosphoruschloridesorthionylchloride.
Orthoesterscanbeobtainedbythereactionofalcoholsunderacidicwaterfreeconditionswith
benzonitrile.
ReductiontobenzaldehydeandbenzylalcoholispossibleusingDIBALH,LiAlH4orsodium
borohydride.
Thecoppercatalyseddecarboxylationofbenzoatetobenzenemaybeeffectedbyheatingin
quinoline.Also,Hunsdieckerdecarboxylationcanbeachievedbyformingthesilversaltand
heating.Benzoicacidcanalsobedecarboxylatedbyheatingwithanalkalihydroxideorcalcium
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hydroxide.

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31. ^"glycineNacyltransferase"(http://www.brendaenzymes.info/php/result_flat.php4?
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JeanGuyBisaillon(January2005)."Cryptanaerobacterphenolicusgen.nov.,sp.nov.,ananaerobethat
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