Liquid-liquid equilibria for ternary systems acetic acid + n-butyl acetate + hydrocarbons at 293.15 K

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Liquid-liquid equilibria for ternary systems acetic acid +

n-butyl acetate + hydrocarbons at 293.15 K

Romain Richard, Nicolas Ferrando, Marc Jacquin

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Identification number: DOI : 10.1016/j.fluid.2013.07.032

Official URL:

http://dx.doi.org/10.1016/j.fluid.2013.07.032

This is an author-deposited version published in:

http://oatao.univ-toulouse.fr/

Eprints ID: 12000

To cite this version:

Richard, Romain and Ferrando, Nicolas and Jacquin, Marc Liquid-liquid

equilibria for ternary systems acetic acid + n-butyl acetate + hydrocarbons at

293.15 K. (2013) Fluid Phase Equilibria, vol. 356 . pp. 264-270. ISSN

0378-3812

O

pen

A

rchive

T

oulouse

A

rchive

O

uverte (

OATAO

)

Liquid–liquid

equilibria

for

ternary

systems

acetic

acid

+

n-butyl

acetate

+

hydrocarbons

at

293.15

K

Romain

Richard

a

_,

_Nicolas

_Ferrando

b

_,

_Marc

_Jacquin

a,∗

a_{IFPEnergiesnouvelles,RondPointdel’échangeurdeSolaize,BP3,69360Solaize,France} b_{IFPEnergiesnouvelles,1-4AvenuedeBois-Préau,92852Rueil-Malmaison,France}

Keywords:

Liquid–liquidequilibriumdata Ternarymixture

Hydrocarbons UNIQUACmodel

a

b

s

t

r

a

c

t

Liquid–liquid equilibrium data for acetic acid+n-butyl acetate+hydrocarbons ternary systems at T=293.15Karereportedinthiswork.Theeffectofhydrocarbonchainlengthonliquid–liquidequilibrium isdeterminedanddiscussed.Aliphatichydrocarbonssuchashexadecane,dodecaneanddecanewere particularlyinvestigated.Theorganicchemicals(estersandhydrocarbons)werequantifiedbygas chro-matographyusingaflameionizationdetectorwhileaceticacidwasquantifiedbytitrationwithsodium hydroxide.Experimentaltie-linedatafortheternarymixtureswerecorrelatedusingOthmer–Tobias, BachmanandHandcorrelationsinordertoshowthereliabilityoftheexperimentalresults.Finally,these experimentaldatawerecorrelatedwiththeUNIQUACmodel.Itappearedthatthismodelprovidesagood correlationofthesolubilitycurvewiththesethreehydrocarbons.

1. Introduction

Lowmolecularweightestersaremostcommonlysynthesized bydirectesterificationofcarboxylicacidswithalcoholsin pres-enceofacidcatalystsbyeithera batchor acontinuousprocess

[1–4].Estersareessentialforthefragranceandflavouringindustry. n-butylacetate(BA)isawidelyknownesterusedasasolventin theproductionoflacquersforexample,butmorecommonlyasa syntheticappleflavouringusedinfoodindustry[5].Productionof BAincreasedinthelastdecadebecauseitslowtoxicityandlow environmentalimpactcomparedwithotheresters[6].

Industrially,themostcommonlyusedseparationprocessesfor suchequilibrium-limitedreversiblereactionsis reactive distilla-tion[7,8].Nevertheless,inthecaseofbutylacetate,distillationis high-energyconsumingduetolowrelativevolatilitiesbetweenthe carboxylicacidandtheester.Indeed,theboilingpointsofacetic acid(118◦_{C)andbutylacetate(126}◦_{C)arerelativelyclose,and}

thusseparationbydistillationrequireahighernumberofstageand refluxratioincomparisontootheresters.Withtheincreasingprice ofenergy,alternativeseparationtechniqueshavetobeconsidered, inordertoreducetheenergyconsumptionassociatedwiththe sep-arationofthecomponents.Inthisstudy,wefocusonliquid–liquid extractionoftheprincipalproduct,n-butylacetate(BA)fromthe remainingreactant,aceticacid(AA),thesemixturebeingasingle homogeneousphase.Thistechniqueisofconsiderableeconomic

importanceinthechemicalindustryandmaybeconsideredeither attheendofthereactionorduringthereactioninordertoshiftthe equilibrium.Thenatureofsolventnaturallyinfluencesthe equilib-riumcharacteristicsofBAextractionfromAAsolutions.Previous worksgivesomedataonphaseequilibriumforsystemssuchas aceticacidandbutan-1-ol[9]orternarysystemswithaceticacid, waterandesters[10]oralcohols[11–13].Inthisstudy,aliphatic hydrocarbons(HCs),fromhexane(C6)tohexadecane(C16),were usedasorganicsolvent.Someliquid–liquidequilibrium(LLE)data forsuchternarysystemsAA–BA–HCwereobtainedatT=293.15K, underatmosphericpressure.

Firstofall,mutualsolubilityofAAandHCswerestudiedinorder todeterminesuitablesolventsforliquid–liquidextractionofBA inexcessofAA.LLEresultsfortheternarysystemsAA+BA+HC presentinga biphasicareaaregivenin this work.Moreover,to showtheconsistencyofourexperimentalresults,tie-linedatawere correlatedusingOthmer–Tobias,BachmanandHandcorrelations. Finally,experimentalternarydiagramswerecomparedwithdata calculatedwiththeUNIQUACmodel.Thismodelmayprovidea goodcorrelationofthesolubilitycurvewiththehydrocarbonsof interest.

2. Experimental

2.1. Materials

Allchemicals(n-butylacetate,glacialaceticacid, hexaneC6, octaneC8,decaneC10,dodecaneC12andhexadecaneC16)were purchasedfromSigma–Aldrich.Theywereofguaranteedreagent

Table1

Compositionsofinitialmixtures,experimentaltie-lines,solutedistributionratios,Dandselectivity,Sforternarysystems[AA+BA+HC]atT=293.15K.

Initialcomposition AA-richphase HC-richphase D S

wAA wBA wHC wAA wBA wHC wAA wBA wHC Octane 0.500 0.000 0.500 0.747 0.000 0.253 0.266 0.000 0.734 – – 0.495 0.010 0.495 – – – – – – – – Decane 0.500 0.000 0.500 0.846 0.000 0.154 0.217 0.000 0.783 – – 0.490 0.020 0.490 0.811 0.030 0.159 0.252 0.017 0.731 0.577 1.714 0.480 0.040 0.480 0.748 0.058 0.194 0.288 0.038 0.674 0.656 1.626 0.475 0.050 0.475 0.713 0.069 0.218 0.316 0.047 0.637 0.688 1.768 0.470 0.060 0.470 0.655 0.081 0.264 0.359 0.064 0.577 0.800 1.462 0.462 0.075 0.463 – – – – – – – – Dodecane 0.500 0.000 0.500 0.881 0.000 0.119 0.153 0.000 0.847 – – 0.487 0.025 0.488 0.855 0.044 0.101 0.175 0.020 0.805 0.451 2.206 0.474 0.050 0.476 0.806 0.079 0.115 0.192 0.039 0.769 0.490 2.055 0.462 0.075 0.463 0.761 0.105 0.134 0.219 0.061 0.720 0.581 2.018 0.450 0.100 0.450 0.699 0.131 0.170 0.258 0.091 0.651 0.696 1.889 0.437 0.125 0.438 0.594 0.155 0.251 0.333 0.120 0.547 0.775 1.383 0.425 0.150 0.425 – – – – – – – – Hexadecane 0.500 0.000 0.500 0.948 0.000 0.052 0.098 0.000 0.902 – – 0.475 0.050 0.475 0.872 0.083 0.045 0.110 0.030 0.860 0.357 2.821 0.450 0.100 0.450 0.765 0.167 0.068 0.128 0.065 0.807 0.391 2.328 0.425 0.150 0.425 0.705 0.219 0.076 0.129 0.100 0.771 0.460 2.520 0.400 0.200 0.400 0.583 0.272 0.145 0.187 0.167 0.646 0.614 1.913 0.387 0.225 0.388 0.521 0.290 0.189 0.222 0.208 0.570 0.716 1.683 0.375 0.250 0.375 0.433 0.289 0.278 0.292 0.239 0.469 0.826 1.222 0.362 0.275 0.363 – – – – – – – –

gradeandtheirpuritiesarereportedbythesuppliertobehigher than99%.Theywereusedwithoutanyfurtherpurificationasno impuritiesweredetectedusinggaschromatographywithaflame ionizationdetector(GC-FID).Theamountofwaterinaceticacid wasdeterminedusingaKarl–Fisherapparatus(831KFCoulometer, Metrohm),thisvaluebeingof396+/−54ppm.

2.2. Procedure

Ternary mixtures ofknown composition(AA+BA+HC)were preciselypreparedinclosedvialsandmixedduringatleast3hat 293.15K.Theaccuracyofthetemperatureis1K.Thetotalweight of each sample was approximately 40g. Whenthe thermody-namicequilibriumwasachieved,thesystemseparatedintotwo liquidphasesthatbecametransparentwithawell-defined inter-face.Afterthisdecantation,thelowerphasecontainingmainlyAA andtheremainingHC-richupperphaseweresuccessivelycollected andweighted.Afterseparation,samplesofbothphaseswerestill transparentandwerecarefullyanalyzedtodeterminetheir com-positionsinordertobuildtheLLEtie-lines.

2.3. Analysismethods

Ternarymixtureswereanalyzedbygaschromatography(GC) usinganAgilentTechnologiesapparatus(6890NNetworkGC Sys-tem) coupled to a flame ionization detector (FID) in order to determineBAandHCamounts.Separationwascarriedoutwitha capillarycolumn(HP-FFAPcolumn,50m,0.32mm,0.50mm)from AgilentJ&WGCColumns.Thechromatographwasequippedwith anautomaticsplitinjectorandtheinjections(0.5mL)were per-formedwithasplitratioof100.Thecarriergaswasheliumandthe columnheadpressurewasadjustedto15psi.Injectortemperature was220◦_{C.Temperatureintheovenwasheld14minat90}◦_C,then

rampedto200◦_Cat10◦_Cmin−1_{andfinallyheld5minat200}◦_C.

Thetotalrunningtimewas30min.Thetemperatureofthe detec-tor(FID)was250◦_{C.Eachsamplewasanalyzedthreetimesand}

thevaluesofmassfractionsgiveninthispaperaretheaverageof

thethreeinjections.Theuncertaintyisu(w)=0.001,which corre-spondstothemaximumstandarddeviationcalculated.AAcould alsobequantifiedbyGC-FIDbutresultsarelessreliable.

Thatiswhyanautomatictitrator(751GPDTitrino,Metrohm) wasusedtodeterminethequantityofAAineachsample.We veri-fiedthatnohydrolysisofBAoccursduringthetitrationwithsodium hydroxide(0.1M),withstandardmixturesofAAandBAoverthe wholerangeofcomposition.ThepHofthesolutionwasmeasured throughout thetitration thankstoanelectrode, accuracybeing moreimportantwithanelectrodethananindicator.Theendpoint correspondstoasuddenchangeinthemeasuredpH,andthenthe

Fig.2.TernarydiagramforLLEof[AA+BA+decane]atT=293.15K;(··· ···)UNIQUACtie-linedata,(—)UNIQUACsolubilitycurve,(-d-)experimentaltie-linedata.

equivalencepointallowsthedeterminationofAAamountinthe sample.

3. Resultsanddiscussion

3.1. LLEexperimentalresults

First ofall, miscibilityof acetic acidwithhydrocarbonswas determined.ItwasnoticedthatAAandhexaneweremiscibleinall proportionswhereasAAandalltheotherhydrocarbonspresentan incompletemutualsolubility.TheresultsarereportedinTable1

(lineswitha butylacetatemassfractionwBAequaltozero) and

representedinFig.1.Itisexperimentallyshownthatthebiphasic areaislargerwhenthehydrocarbonchainlengthincreases. Con-cerningthesystemAA+BA+C8,asit canbenoticedinTable1, withonly1%ofBA(wBA=0.01),themixtureismonophasic,which

meansthatthebiphasicareaofthissystemisverysmall.Thatis

whywedidnotrepresentaphasediagramofthissystem.TheLLE diagramsfortheotherternarysystemswitheachhydrocarbonare plottedinFigs.2–4.Because(HC+AA)isaliquidpairthatispartially miscibleandthetwootherliquidpairs(BA+AA)and(BA+HC)are completelymiscible,theternarysystemsbehaveastype-ILLE[14]. Inordertoevaluatetheextractingcapabilityofthehydrocarbon solventfortheseparationoftheesterfromacidicsolutions,the selectivity(S) and solute distributionratio (D) were calculated fromexperimentaldataaccordingtofollowingEqs.(1)–(2):

S=w HC BA×wAAAA wAA BA×wHCAA (1) D=w HC BA wAA BA (2) wherewisthemassfraction,subscriptsBAandAArefer respec-tively to n-butyl acetate and acetic acid, and superscripts HC

Fig.4.TernarydiagramforLLEof[AA+BA+hexadecane]atT=293.15K;(···△···)experimentalsolubilitycurve,(—)UNIQUACsolubilitycurve,(-N-)experimentaltie-line data.

and AA represent thehydrocarbon-rich phase and theAA-rich phase, respectively. Values of S and Dare reportedin Table 1. Theseparametersarewidelyusedforevaluatingthesolvent(HC) efficiencyinunitoperationssuchasliquid–liquidextraction.The distribution coefficient is related to the extracting capacity of BAintheHCanddeterminestheamountofHCneededforthe extractionprocess,whiletheselectivityisrelatedtothenumber ofstagesneededintheseparationprocess.Theoretically,higher selectivitycorrespondstofewerstagesrequiredforagiven sep-arationprocessandahigherdistributioncoefficientcorresponds toaloweramountofsolventneededforagivenseparation,and consequentlyasmallerapparatusandloweroperatingcosts.The selectivityasafunctionofsolutedistributionratiosforthethree studied ternary systems is plotted for all initial compositions andparticularlyforaninitialcompositionofwBA=0.05inFig.5.

Fig.5.(a)SelectivitySasafunctionofsolutedistributionratioDforthethree sys-tems[AA+BA+HC]withHC:(d)decane,()dodecane,(N)hexadecane;(b)example forinitialcompositionwBA=0.05.

As it was expected, the selectivity decreases with the solute distributionratio, whichinvolvesa compromise betweenthese two parameters,i.e. betweenthesizeof theapparatusandthe amountofsolventneeded.Nosignificantdifferencesareobserved between thethree hydrocarbons.Nevertheless, as the biphasic areabecomeslargerwhenthelengthofhydrocarbonincreases, hexadecanemaybeanappropriatesolventforthisliquid–liquid extractioninordertocollectanextractwithhigherpurity.

3.2. Consistencyoftie-linedata

Inthiswork,theOthmer–Tobiascorrelation[15](Eq.(3)),the Bachmancorrelation[16](Eq.(4))andtheHandcorrelation[17]

(Eq.(5))wereusedtoensurethequalityoftheobtained experi-mentaltie-linedata:

ln



₁ −wHC_HC wHC HC



=A+Bln



₁ −wAA_AA wAA AA



(3) wHC BA=A′+B′ wHC BA w_AAAA (4) ln



_wAA BA wAA AA



=A′′+B′′_ln



_wHC BA wHC HC



(5)

where w is the mass fraction, subscripts BA, HC and AA refer respectivelyton-butylacetate,hydrocarbonandaceticacid,and superscriptsHCandAArepresentthehydrocarbon-richphaseand theAA-richphase,respectively;A,B,A’,B’,A′′_andB′′_,the

param-etersoftheOthmer–Tobiascorrelation,theBachmancorrelation andtheHandcorrelation,respectively.Thecorrelationparameters and thecorrelationfactor R2 _{values weredeterminedby a}

par-tialleast-squaresregression. Thecorrelatedresultsarereported inTable2.TheOthmer–Tobias,BachmanandHandplotsarealso showninFigs.6–8,respectively,forthethreeinvestigatedsystems withdecane,dodecaneandhexadecane.AsseenfromTable2and

Figs.6–8,theclosenessofthecorrelationfactorR2_tounityand

Table2

ConstantsofOthmer–Tobias,BachmanandHandequationssystem.

Hydrocarbon Othmer–Tobiascorrelation Bachmancorrelation Handcorrelation

A B R2 _A′ _B′ _R2 _A′ ′ _B′ ′ _R2

Decane 0.258 0.892 0.995 0.002 0.656 0.992 −0.332 0.785 0.994 Dodecane 0.145 0.919 0.995 0.007 0.594 0.981 −0.220 0.727 0.994 Hexadecane −0.246 0.907 0.966 0.023 0.435 0.961 0.159 0.707 0.982

3.3. Correlationmodel

Experimentaldataarethuscorrelated withtheexcess Gibbs freeenergymodelUNIQUAC[18].Theexpressionoftheactivity coefficientofthecompoundiisgiveninthefollowingEq.(6):

ln i=ln i xi +1−i xi −z 2



ln i i +1−i i



+qi

"

1−ln



X

N j=1jji



−

X

N j=1 jji

P

N k=1kkj

#

(6)

Fig.6.Othmer–Tobiasplotforthe[AA+BA+HC]ternarysystemsatT=293.15K withHC:(d)decane,()dodecane,(N)hexadecane.

Fig.7.Bachmanplotforthe[AA+BA+HC]ternarysystemsatT=293.15KwithHC: (d)decane,()dodecane,(N)hexadecane.

Table3

StructuralparametersoftheUNIQUACmodel.

Compound r(m2_{/kmol) q(m}3_/kmol)

Aceticacid 5.180×108 _0.0333 n-Butylacetate 1.049×109 _0.0732 Decane 1.504×109 _0.1092 Dodecane 1.774×109 _0.1296 Hexadecane 2.314×109 _0.1706 Table4

OptimizedUNIQUACbinaryparameters.

Pair Bij(K) Bji(K) AA+BA 29.006 80.708 AA+C10 −18.535 −270.071 AA+C12 −26.558 −270.500 AA+C16 −14.638 −333.271 BA+C10 50.602 42.413 BA+C12 16.526 54.114 BA+C16 8.937 35.641 with: i= xiri

P

N j=1xjrj (7) i=

_P

x_Niqi j=1xjqj (8) z=10(coordinationnumber) (9) ij=exp



Bij T



(10) wherexstandsforthemolarfraction,Nthenumberofcomponents,

Tthetemperature(K)andBijanempiricalasymmetricbinary

inter-actionparameter.Thepurecompoundstructuralparametersrand

Table5

Calculatedtie-lineswiththeUNIQUACmodel(massfractions).

Initialcomposition AA-richphase HC-richphase rmsd(%)

wAA wBA wHC wAA wBA wHC wAA wBA wHC Decane 0.500 0.000 0.500 0.846 0.000 0.154 0.217 0.000 0.783 2.45 0.490 0.020 0.490 0.796 0.025 0.180 0.236 0.016 0.748 0.480 0.040 0.480 0.743 0.047 0.210 0.261 0.034 0.705 0.475 0.050 0.475 0.715 0.058 0.227 0.277 0.043 0.680 0.470 0.060 0.470 0.684 0.068 0.248 0.295 0.053 0.652 Dodecane 0.500 0.000 0.500 0.915 0.000 0.085 0.168 0.000 0.832 2.14 0.487 0.025 0.488 0.861 0.036 0.103 0.179 0.016 0.805 0.474 0.050 0.476 0.808 0.068 0.124 0.193 0.035 0.772 0.462 0.075 0.462 0.754 0.097 0.149 0.213 0.056 0.731 0.450 0.100 0.450 0.697 0.123 0.180 0.238 0.080 0.682 0.437 0.125 0.438 0.632 0.146 0.222 0.273 0.107 0.619 Hexadecane 0.500 0.000 0.500 0.967 0.000 0.033 0.088 0.000 0.912 2.65 0.475 0.050 0.475 0.870 0.080 0.050 0.095 0.022 0.883 0.450 0.100 0.450 0.780 0.146 0.074 0.109 0.053 0.838 0.425 0.150 0.425 0.692 0.201 0.107 0.131 0.094 0.775 0.400 0.200 0.400 0.597 0.246 0.157 0.167 0.146 0.687 0.387 0.225 0.388 0.542 0.264 0.194 0.194 0.176 0.630 0.375 0.250 0.375 0.474 0.277 0.249 0.234 0.212 0.554

q(vanderWaalsareaandvanderWaalsvolume,respectively)are extractedfromtheDIPPRdatabase[19]andarereportedinTable3. TheinteractionbinaryparametersBijaresimultaneouslyadjusted

toreproducetheexperimentalmutualsolubilitiesoftheternary systems investigated.The objective function(OF) minimized in ordertodetermineoptimalparametersisgivenbyEq.(11):

OF=

X

M i=1

X

N j=1 1− K_ijexp Kcalc ij

!

2 (11) whereMisthenumberofexperimentaldataandNthenumberof components.Kijisthemolardistributionratioofthecompoundj

fortheithexperiment,definedbyEq.(12):

Kij= xAA ij xHC ij (12) wherexdenotesthemolarfraction,andthesuperscriptsAAand HC stand for the acetic acid-rich phase and hydrocarbon-rich phase,respectively.OptimizedbinaryparametersBijarereported

inTable4.

Toevaluatethemodelperformanceforeachsystemstudied,a root-meansquaredeviation(rmsd)betweentheexperimentaland calculatedcompositionsinbothphasesiscalculatedusingEq.(13):

rmsd=100·

r

P

M i=1

P

N j=1

$

xAA,exp ij −x AA,calc ij

2 +

$

xHC,exp ij −x HC,calc ij

2 2MN (13)

CalculatedvaluesaswellasrmsdarereportedinTable5.The modelresultsarefoundinwellagreementwithexperimental val-ues,withamaximalrmsdof2.65%fortheAA+BA+C16mixture. Our values of rmsdare similarto values ofprevious works on ternarysystems[20,21].

4. Conclusion

Liquid–liquid equilibrium (LLE) data for the systems acetic acid+n-butylacetate+hydrocarbonsweredeterminedat293.15K andatmosphericpressure.Asitwasshownthathexaneandacetic acidweremiscibleinallproportions,ternarymixtureswerenot feasible. Nevertheless, all the other investigated systems from octanetohexadecaneformedatype-IphasediagramofLLE.The two-phaseregionincreasedwithincreasingthehydrocarbonchain lengthfortheternarysystemsstudied.Moreover,consistencyof

experimentaldatahasbeenshownusingOthmer–Tobias,Bachman andHandcorrelations.Ingeneral,experimentaldatacouldbe prop-erlycorrelatedusinganUNIQUACmodel.Thephasediagramsofthe systemsaceticacid+n-butylacetate+hydrocarbonscanbeusedin liquid–liquidextractionpracticeandasreferencedata.

Listofsymbols

A,B Othmer–Tobiascorrelationconstants

A′_,B′ _{Bachmancorrelationconstants}

A′′_,B′′ _{Handcorrelationconstants}

Bij UNIQUACbinaryinteractionparameter

C6 hexane C8 octane C10 decane C12 dodecane C16 hexadecane

D solutedistributionratio(inmass)

M numberofexperimentaldata

N numberofcomponents

K molardistributionratio OF objectivefunction

q molecularpurecompoundstructuralparameter,vander Waalsvolume(m3_/kmol)

r molecularpurecompoundstructuralparameters,vander Waalsarea,(m2_/kmol)

R2 _{Othmer–Tobias,Bachman,Handcorrelationcoefficients}

rmsd rootmeansquaredeviation

S selectivity

T temperature(K)

w concentrationinmassfraction

x concentrationinmolefraction

Superscripts

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