Styrene

FromWikipedia,thefreeencyclopedia

Styrene,alsoknownasethenylbenzene,vinylbenzene,and
phenylethene,isanorganiccompoundwiththechemical
formulaC6H5CH=CH2.Thisderivativeofbenzeneisacolorless

Styrene

oilyliquidthatevaporateseasilyandhasasweetsmell,although
highconcentrationshavealesspleasantodor.Styreneisthe
precursortopolystyreneandseveralcopolymers.Approximately
25milliontonnes(55billionpounds)ofstyrenewereproduced
in2010.[4]

Contents
1 Occurrence,history,anduse
1.1 Naturaloccurrence
1.2 History
1.3 Industrialproductionfromethylbenzene
1.4 Otherindustrialroutes
1.4.1 Fromethylbenzenehydroperoxide
1.4.2 Fromtolueneandmethanol
1.4.3 Frombenzeneandethane
1.5 Laboratorysynthesis
2 Polymerization
3 Healtheffects
4 References
5 Externallinks

Occurrence,history,anduse
Naturaloccurrence
Styreneisnamedforstyraxbalsam,theresinofLiquidambar
treesoftheHamamelidaceaeplantfamily.Styreneoccurs
naturallyinsmallquantitiesinsomeplantsandfoods
(cinnamon,coffeebeans,andpeanuts),andisalsofoundincoal
tar.

History
In1839,theGermanapothecaryEduardSimonisolateda
volatileoilfromtheresin(called"storax")oftheAmerican
sweetgumtree(Liquidambarstyraciflua).Hecalledtheoil
"Styrol"(now:"styrene").[5][6]Healsonoticedthatwhenstyrol
wasexposedtoair,light,orheat,itgraduallytransformedintoa
hard,rubberlikesubstance,whichhecalled"Styroloxyd"(styrol

Names
PreferredIUPACname
Ethenylbenzene[1]
Othernames
Styrene[1]
Vinylbenzene
Phenylethene
Phenylethylene
Cinnamene
Styrol
DiarexHF77
Styrolene
Styropol
Identifiers
CASNumber

100425(http://www.common
chemistry.org/ChemicalDetail.a
spx?ref=100425)

ChEBI

CHEBI:27452(https://www.eb
i.ac.uk/chebi/searchId.do?chebi
Id=27452)

ChEMBL

ChEMBL285235(https://www.
ebi.ac.uk/chembldb/index.php/c
ompound/inspect/ChEMBL285
235)

ChemSpider

7220(http://www.chemspider.c
om/ChemicalStructure.7220.ht
ml)

oxide,now:"polystyrene").[7]By1845,theGermanchemist
AugustHofmannandhisstudentJohnBlythhaddetermined
Styrol'sempiricalformula:C8H8.[8]Theyhadalsodetermined

Jmol3Dmodel

thatSimon's"Styroloxyd"whichtheyrenamed"Metastyrol"
hadthesameempiricalformulaasStyrol.[9]Furthermore,
theycouldobtainStyrolbydrydistillingMetastyrol.[10]In1865,
theGermanchemistEmilErlenmeyerfoundthatStyrolcould
formadimer,[11]andin1866theFrenchchemistMarcelin
BerthelotstatedthatMetastyrolwasapolymerofStyrol.[12]
Meanwhile,otherchemistshadbeeninvestigatinganother
componentofstorax,namely,cinnamicacid.Theyhadfound
thatcinnamicacidcouldbedecarboxylatedtoformcinnamne
(orcinnamol),whichappearedtobeStyrol.In1845,French
chemistEmilKoppsuggestedthatthetwocompoundswere
identical,[13]andin1866,Erlenmeyersuggestedthatboth
cinnamolandStyrolmightbevinylbenzene.[14]However,the
Styrolthatwasobtainedfromcinnamicacidseemeddifferent
fromtheStyrolthatwasobtainedbydistillingstoraxresin:the
latterwasopticallyactive.[15]Eventually,in1876,theDutch
chemistvan'tHoffresolvedtheambiguity:theopticalactivity
oftheStyrolthatwasobtainedbydistillingstoraxresinwasdue
toacontaminant.[16]

KEGG

Industrialproductionfromethylbenzene
Themodernmethodforproductionofstyreneby
dehydrogenationofethylbenzenewasfirstachievedinthe
1930s.[17]Theproductionofstyreneincreaseddramatically
duringthe1940s,whenitwaspopularizedasafeedstockfor
syntheticrubber.Becauseitisproducedonsuchalargescale,
ethylbenzeneinturnpreparedonaprodigiousscale(by
alkylationofbenzenewithethylene).[17]Ethylbenzeneismixed
inthegasphasewith1015timesitsvolumeinhigh
temperaturesteam,andpassedoverasolidcatalystbed.Most
ethylbenzenedehydrogenationcatalystsarebasedoniron(III)
oxide,promotedbyseveralpercentpotassiumoxideor
potassiumcarbonate.

Interactiveimage(http://chema
pps.stolaf.edu/jmol/jmol.php?m
odel=c1ccccc1C%3DC)
C07083(http://www.kegg.jp/en
try/C07083)

PubChem

7501(https://pubchem.ncbi.nl
m.nih.gov/compound/7501)

RTECSnumber

WL3675000

UNII

44LJ2U959V(http://fdasis.nlm.
nih.gov/srs/srsdirect.jsp?regno=
44LJ2U959V)

InChI
SMILES

Properties
Chemicalformula

C8H8

Molarmass

104.15g/mol

Appearance

colorlessoilyliquid

Odor

sweet,floral[2]

Density

0.909g/cm3

Meltingpoint

30C(22F243K)

Boilingpoint

145C(293F418K)

Solubilityinwater

0.03%(20C)[2]

Vaporpressure

5mmHg(20C)[2]

Refractiveindex
(nD)

1.5469

Viscosity

0.762cPat20C
Structure

Dipolemoment

0.13D
Hazards

Mainhazards

flammable,toxic

Safetydatasheet

MSDS(http://www.sciencelab.
com/msds.php?msdsId=992511
2)

Rphrases

R10R36

Sphrases

S38S20S23

NFPA704

Flashpoint

31C(88F304K)

Explosivelimits

0.9%6.8%[2]

Lethaldoseorconcentration(LD,LC):
LC50(median
concentration)

2194ppm(mouse,4hr)

LCLo(lowest
published)

10,000ppm(human,30min)

5543ppm(rat,4hr)[3]
2771ppm(rat,4hr)[3]

UShealthexposurelimits(NIOSH):
PEL(Permissible) TWA100ppmC200ppm600
ppm(5minutemaximumpeak
inany3hours)[2]
REL
(Recommended)

TWA50ppm(215mg/m3)ST
100ppm(425mg/m3)[2]

IDLH(Immediate 700ppm[2]
danger)
Relatedcompounds
Relatedstyrenes
relatedaromatic
compounds

Polystyrene,Stilbene
Ethylbenzene

Exceptwhereotherwisenoted,dataaregivenfor
materialsintheirstandardstate(at25C[77F],
100kPa).
verify(whatis

?)

Infoboxreferences

Steamservesseveralrolesinthisreaction.Itisthesourceofheatforpoweringtheendothermicreaction,andit
removescokethattendstoformontheironoxidecatalystthroughthewatergasshiftreaction.Thepotassium
promoterenhancesthisdecokingreaction.Thesteamalsodilutesthereactantandproducts,shiftingthepositionof
chemicalequilibriumtowardsproducts.Atypicalstyreneplantconsistsoftwoorthreereactorsinseries,which
operateundervacuumtoenhancetheconversionandselectivity.Typicalperpassconversionsareca.65%fortwo
reactorsand7075%forthreereactors.Selectivitytostyreneis9397%.Themainbyproductsarebenzeneand
toluene.Becausestyreneandethylbenzenehavesimilarboilingpoints(145and136C,respectively),their
separationrequirestalldistillationtowersandhighreturn/refluxratios.Atitsdistillationtemperatures,styrene
tendstopolymerize.Tominimizethisproblem,earlystyreneplantsaddedelementalsulfurtoinhibitthe
polymerization.Duringthe1970s,newfreeradicalinhibitorsconsistingofnitratedphenolbasedretarderswere
developed.Morerecently,anumberofadditiveshavebeendevelopedthatexhibitsuperiorinhibitionagainst
polymerization.However,thenitratedphenolsarestillwidelyusedbecauseoftheirrelativelylowcost.These
reagentsareaddedpriortothedistillation.
Improvingconversionandsoreducingtheamountofethylbenzenethatmustbeseparatedisthechiefimpetusfor
researchingalternativeroutestostyrene.OtherthanthePOSMprocess,noneoftheserouteslikeobtainingstyrene
frombutadienehavebeencommerciallydemonstrated.

Otherindustrialroutes

Fromethylbenzenehydroperoxide
StyreneisalsocoproducedcommerciallyinaprocessknownasPOSM(LyondellChemicalCompany)orSM/PO
(Shell)forstyrenemonomer/propyleneoxide.Inthisprocessethylbenzeneistreatedwithoxygentoformthe
ethylbenzenehydroperoxide.Thishydroperoxideisthenusedtooxidizepropylenetopropyleneoxide.The
resulting1phenylethanolisdehydratedtogivestyrene:

Fromtolueneandmethanol
Styrenecanbeproducedfromtolueneandmethanol,whicharecheaperrawmaterialsthanthoseinthe
conventionalprocess.Thisprocesshassufferedfromlowselectivityassociatedwiththecompetingdecomposition
ofmethanol.[18]ExelusInc.claimstohavedevelopedthisprocesswithcommerciallyviableselectivities,at400
425Candatmosphericpressure,byforcingthesecomponentsthroughaproprietaryzeoliticcatalyst.Itis
reported[19]thatanapproximately9:1mixtureofstyreneandethylbenzeneisobtained,withatotalstyreneyieldof
over60%.[20]
Frombenzeneandethane
Anotherroutetostyreneinvolvesthereactionofbenzeneandethane.Thisprocessisbeingdevelopedby
SnamprogettiS.p.A.andDow.Ethane,alongwithethylbenzene,isfedtoadehydrogenationreactorwithacatalyst
capableofsimultaneouslyproducingstyreneandethylene.Thedehydrogenationeffluentiscooledandseparated
andtheethylenestreamisrecycledtothealkylationunit.Theprocessattemptstoovercomepreviousshortcomings
inearlierattemptstodevelopproductionofstyrenefromethaneandbenzene,suchasinefficientrecoveryof
aromatics,productionofhighlevelsofheaviesandtars,andinefficientseparationofhydrogenandethane.
Developmentoftheprocessisongoing.[21]

Laboratorysynthesis
Alaboratorysynthesisofstyreneentailsthedecarboxylationofcinnamicacid:[22]

C6H5CH=CHCO2H:C6H5CH=CH2+CO2
Styrenewasfirstpreparedbythismethod.[23]

Polymerization
Thepresenceofthevinylgroupallowsstyrenetopolymerize.Commerciallysignificantproductsinclude
polystyrene,ABS,styrenebutadiene(SBR)rubber,styrenebutadienelatex,SIS(styreneisoprenestyrene),SEB
S(styreneethylene/butylenestyrene),styrenedivinylbenzene(SDVB),styreneacrylonitrileresin(SAN),and
unsaturatedpolyestersusedinresinsandthermosettingcompounds.Thesematerialsareusedinrubber,plastic,
insulation,fiberglass,pipes,automobileandboatparts,foodcontainers,andcarpetbacking.

Healtheffects
Styreneisregardedasa"hazardouschemical",especiallyincaseofeyecontact,butalsoincaseofskincontact,of
ingestionandofinhalation,accordingtoseveralsources.[17][24][25][26]Styreneislargelymetabolizedintostyrene
oxideinhumans,resultingfromoxidationbycytochromeP450.Styreneoxideisconsideredtoxic,mutagenic,and
possiblycarcinogenic.Styreneoxideissubsequentlyhydrolyzedinvivotostyreneglycolbytheenzymeepoxide
hydrolase.[27]TheU.S.EnvironmentalProtectionAgency(EPA)hasdescribedstyrenetobe"asuspectedtoxinto
thegastrointestinaltract,kidney,andrespiratorysystem,amongothers".[28][29]On10June2011,theU.S.National
ToxicologyProgramhasdescribedstyreneas"reasonablyanticipatedtobeahumancarcinogen".[30][31]However,
aSTATSauthordescribes[32]areviewthatwasdoneonscientificliteratureandconcludedthat"Theavailable
epidemiologicevidencedoesnotsupportacausalrelationshipbetweenstyreneexposureandanytypeofhuman
cancer".[33]Despitethisclaim,workhasbeendonebyDanishresearcherstoinvestigatetherelationshipbetween
occupationalexposuretostyreneandcancer.Theyconcluded,"Thefindingshavetobeinterpretedwithcaution,
duetothecompanybasedexposureassessment,butthepossibleassociationbetweenexposuresinthereinforced
plasticsindustry,mainlystyrene,anddegenerativedisordersofthenervoussystemandpancreaticcancer,deserves
attention".[34]TheDanishEPArecentlyconcludedthatthestyrenedatadonotsupportacancerconcernfor
styrene.[35]
Variousregulatorybodiesrefertostyrene,invariouscontexts,asapossibleorpotentialhumancarcinogen.The
InternationalAgencyforResearchonCancerconsidersstyrenetobe"possiblycarcinogenictohumans".[36]
Chronicexposuretostyreneleadstotiredness/lethargy,memorydeficits,headachesandvertigo.[37]
TheU.S.EPAdoesnothaveacancerclassificationforstyrene,[38]butishasbeenthesubjectoftheirIntegrated
RiskInformationSystem(IRIS)program.[39]TheU.S.NationalToxicologyProgramoftheU.S.Departmentof
HealthandHumanServiceshasdeterminedthatstyreneis"reasonablyanticipatedtobeahumancarcinogen".[40]

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Externallinks
CDCStyreneNIOSHWorkplaceSafetyandHealthTopic(http://www.cdc.gov/niosh/topics/styrene/)
SafetyandHealthTopics|Styrene(OSHA)(http://www.osha.gov/SLTC/styrene/index.html)
Retrievedfrom"https://en.wikipedia.org/w/index.php?title=Styrene&oldid=739856253"
Categories: Hazardousairpollutants Monomers IARCGroup2Bcarcinogens Alkenes
Aromaticcompounds Commoditychemicals
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