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60650 700 707007070 550 600 650 700 750 )uer(eK()K) erearaat(utKurere)e(K(K)) TemTpemraptuereat(uKre) (K) TeTemeTmpTepemrmeaprptpaeueetruareaarteu(tuKr(ereK)e()K(K)) Cadtaealycstitvsa2ti0o1n6i,s6attributedtotheformationofoxygenatedcompoundswhichmayleadtotheformationof 9 CaCtaCalaCtyastsaltystslasy2tlssy0ts12t6260s,0,1261606,1,66, 6 coke on catalysts. The variation of the alkanes, o-xylene, and polyalkylated benzene’s selectivities is 4 4 insignificant. Benzene, phenol, methylanisole, and other products are in minor amounts and their deactivation is attributed to the formation of oExyEcgEexepxcEntecxapeacatptlelektkpdatlanckleaokaslnamk,neapsean,sore,ousam,nraordaomtstrimiocacwmstsai,htcaiiscatac,isnch,dsam,napndpahdhnyepdnphleohepalnehidnocesosltni,olcoiscolt,ishtc,hesoe,otfrhotoherptremhroepadrdprtuoirpococdrtntduosucdotcsusftucsctsshusucsahacushcahisansda selectivities change slightly with increasing the time on stream. npdahnedpnhopelnhicoesnlci,iocolsoik,ctehsoe,totrhonetprhcreoaprdtrauoplcdyrtousdctstus.ucTtcshuhcesahusvchaisrsniadaisatnindoienan,ndeaon,nfaepnt,hatpepnhhaptlhlehkantalhenad,dneleasrd,ni,idevedaorea,adnin-rtvetidixdahvarnyieteaevditlistsvherai,ventaisieihevlrl,ses,e,aoiosrala,senloasxdoliesoxpetxioiesnilxtsytisisasnmitlnksaiamnsyllmllsamlamtmllealaodolmalumbanonmetoutsnun.o.zntusetn.sn.tse.’s selectivities is , and phenolliics,, ottherr prroductts such as iindane,, naphtthallene,, and ttheiirr maomunotusn.ts. 5 mallmllaomuonoutusn.nttsisn..signif1i0c0ant. Benzene, phenol, methylanisole, and o2t0her products are in minor amounts and their 100101000100 selectivities5ch5an5geslightlywithincreasingthetime(oa)n)(as()at)r(bae)am. 80 (b) (b)((b)) 5 55 5 (b) (b()b)(b) (a) 100 4 4 (b) 80 808080 60 40 20 1 0 0 60 60 (b) 60 60 10 15 40 404040 40 3 0 750 7570570750 100 200 300 400 500 3 3 (a)3 3 4 4 4 4 4 3 333 434 15 20 80 60 40 20 alsank,neaesn,s,e,s, : b:e:nb:zbeenbnzeezen,enznee,n,e, : to:l:tuto:otelolnutuloeuel,nenunee,n,e, : p::-p:/pmp-:/p--/-mpxm/-my-/-xlmx-eyxyn-lyxlelynenleneene : o-:xo:oyo-:lxlx-eoyxyn-ylxel,y,nelne,e,n,e, : p:op:lpyopo:alolyplyklkoayaylakylklayakytlelylekadlytaeltadertdoeamdraoraomtrimiocacamstsati,i,tcaiscst,i,sc,s, : o:th:oeot:rhtsohe,trehsre,sr,s, : p allkanes,, ::beFenizgzeunre,,4.:Epf-f/e:m:ct-toxoollyufletninme,,eonst:r:e:oap-m--x//myol--nexny(yelale,e)ntehem-c::r:epsoolylacloknyvlaetresdionaraonmdadtiecos,xygenat:edopthreordsu,ct alylyklakaytleylklkadlyaytleltlaedartdteoeadmdaroraoamtrrimocoamsamti,itacaiactstti,s,ic,s,, : o:th:oe:ot:rhotsohoe,thetrhsre,s,er,rs,, : p:h:ep:n:p:h:ohpeplenh,hnoeonln,lo,ol,, : o:-c:or:o-e-:c-socro-er-clcecs;rosoreols;slo;oll;; : x:y:lx:e:xyxnylyxoellylneslno,n,eolnoslo,lss,l,s, : p::o:plpy:opoalolplyklkoyaylaylklakytleylelkadlytateltadepdtdheepdnphoheplneshsno.eolns(l(o.sR.lse(.Ra(Rce(taeRiocaentcnaitocionctinon distributi:onphaendol,(b) oxy:geon-acrtedsol;product :dixstyrliebnuotliso,n from :copnovleyratliknyglatmed-crpehsoenlolws,ith 2 2 2 2 2 222 1 111 0 000 550 555050550 2 15 1 1 1 20 2020120 0 000 000 550 55505505050 600 610600600 T T e e m m Tp p e e e T r mr a a e t p t mTu u e r e r p r e e ma e t ( r ( p u Ka K e r t ) u e ) r a r ( e t Ku ( r ) Ke ) ( K ) 600 606000600 T T 550550 50 600600 650650 60 650 700 700700 70 750 750750 750 600Timeonstre6a5m0 (min) 550 00 0 100 200 300 400 500 0 100 200 300 400 500 menta-iacoctrtnentieiimosotnonenplmetterepcameoturpnparevetetruerarortesetunuirorore(enenao)o(nanptnh)(r(de(aoatah)dc)edotutthehnhcoeveotoxencycdrovosoginenisneorvtnvsnreiaeirorbtrasensunidiodotaninodpdanearnondaxdeunyodcgdxeteoyonxg(gxdxbayeyiyt)ngsgegtaederoetninexbpadayurtteoetgepidoedruononpcdartrouotaodedcdndidtususdudtctcrcrdiptistibdtrsruotirstbditibourouiuntnbcitoutiaontndinodainsa(tndbardi)n)(bdo(oub)x(t)ybyoiogogx)nexeyonygxfageyrtneoegenadmdetaneptpaderctdoeopdpnruorvpcocdertduorducdtdticiunstdtctgrditisibdtsrutirstbitibouroiutnbitouifonrtrionofmrnforofmrmo-mcmrmr-ecm-srcoe-rlcse distribution and (b) oxygenated product distribution from converting m-cresol with Time on stream (min) Time on stream (min) ngdgaeiestnetraditbepudrtoipodrnuocfdrtuodcmitsdcdtroiisnbtvrurietbmirout-intnciorogfenrmsoofm-rlcowrmesi-tocmhmlr-e-mwcsiroetehtlshHomalnDeHotOhlDa.nOo.l. :m:-cm:rrem-e-scs-orcoelrlsecosolnclvoceoencrnvosveinioroevsnrneis,oriosnin,o,n,:al:lk:ala:nkleaekaslsnak,neasen,se,s,:b:e:nbzb:eenebnzezn,nezne,en,e,:to:l:tuot:eolnutloeuel,neune,en,e xgxyeyngaetneadattepdropdrrouodcdtucdctitsdmtdriisisesbtruhriibtbabiunuoutotntiiolo.fnrnofmfrrom-m:mcmr-m-e-cs-rorcelrseoHoslloDHlODcD.oOn..versi:omn:,:-mcmr-e-csrcroreoelsnso:ovllearlskiaone,s, ::albkeanzeesn,e, :be:ntzoelnue,ne, :toluene, : p:ol:pyoaplykoaylyllkaytlekladytleadpdtehdepnhopeplnhso.elns(o.o.Rllses(,RaR, cetaiocntioncn:o:ncmcdomientetidhotihntytiyisolola:nanspi:isop=ple.=2(R2M2eaPMcat,PWPioan/n,W,FW/c=FW/oF7n=/F5d=7ig=75tci5ao7gt·n5gchacst/ga·m:thc·amh/otm·/lh-mccor/ermolsecolrolsce,rsoleoHcslro,/e2ls,H/omclH,2re/eH2ct/srch2oe/ralcsenro=seolos5l=lo,=lmc5=a5,ot,c5alacal,ytarcatsalatytl=aysltsy1t=s.=0t1=1w.0.1t0.w.0w%t.wt.%Pt%t./P%ZPt-/t5ZP/7Zt- : p::oplpyoallykayllklkaytlelladattedpdhpepnhoenlnso.olls(.R. (e((RaRcetaiacoctntiioncnoncodonintdidoiitntiioso:nsp:: p=p =2 2M2 WPMa/P,PFPa=,, 75 gcat·h/molcresol, H2/cresol = 5, catalyst = 1.0 wt. % Pt/Z-57 methanol:. methy:lamni-scorles.ol(Rceoancvtieornsiocno,nditions:: amlk-acnreso,l/metha:nboelnzmeonlea,r ratio :=tolu1e/4n,e, 2e/Htch,r2aHe/cnsro/eclsr=oemls5o=,lac5=ra,t5cara,lytciasaolttya=slrty1a=s.1t0i/1o=1w.,0=1tp.w01%=t/w. 4P%t2,.t/%cPZPMat-/t5PZa7tal-/)y5Z,.s7W-t5)./7=F).1=.0 7w5t.gca%t·hP/mt/oZlc-re5s7ol, W/F = 75 g ̈ h/mol , T = 673 K, essooll,,2H22//crresoll = 5,, cattallystt = 1..0 wtt.. % Ptt//Z--57)).. cat m-cresol = 1.0 wt. % Pt/Z-57).P = 2 MPa). H2 GeGnGerGneanelellrelnyare,la,lrlytatlhy,lle,ytht,cheatehtcaeaclytyacatailaicyctlaytiHlHtcyicDtHicOHDHDOoDOf oOofxfoyofgogxexeyonygx-geycnegon-enc-ntoca-onicntoaitininantiganinicncngoignmcgocpomcomoupumnpnododupsusnondudsnsdu catalyst = 1.0 wt. % Pt/Z-57, W/F = 75 gcat·h/molm-cresol, T = 673 K, PH2 = 2 MPa). : p-/m-xylene : o-xylene, : polyalkylated aromatics, : others, : phenol, : o-cresol; : xylenols, : polyalkylated phenols, ODOof ofxyogxeyng-ecno-nctoanintainingincgomcopmoupnodusndusnduenrdedrifdfdeifrffefenrtenctoncdoindtidiofidntftiedisofrifndnefuefsinsrefteifrunenecsgrntieiantntcagtaclytacatsalatytslaysltsiyststiksinsiokskwnnoknownwotnowntnpotorotpocpreorpeocrdecoectdeehdertodhtuhrgotrhohurugogthuwhgothwtwrotewoarocertaeirocaetcnaitociopntinaotpnhpawtaphtahw DHODOoOfoffxoyoxgxyeyng-ecno--ncotoanitnttaiiningiincgomcopmopuponoudunsndusnudunenrdedrrifdfdeiifrfefenrrtenctotncdcodoiofninftdeidoiriitentiinosotnuscsaiunutsagsilinyngsgts is known to proceed through two reaction pathwa The TGA measurement was carried out to investigate the deposition of the spent catalyst. The weight : methylanisole. (Reaction conditions: m-cresol/methanol molar ratio = 1/4, wcntntpnoivrtotitopotocyreopeopcrdfreo7ectd8ehe.ere2dtotdh%hurtgtothdhurogotuhupwugsgohth1hw1rtot.tew3wa%orocoetaicrorceoentamiacocptptntiaiaotrnpnhneawdtphawawytithsthahwyw[stsa3ahy4ya[s,s3t34w4[5[[3,3]3i34.t45h,,3T]o3.5u5h5]t]TeT].m.hoTehTehnhtyheoedheanrhrynpoeoydoahngndrntlypeohre(dnanog8rtpopgeiph8hosalanea.gyt2tnothieshsh%sosliniyslioiysisolisysrisdodioirsirdeoedcicrrtitedrdceieretceotdcxdetyoedgogxeexeyonygxageytneigionoaentanitoa(i(onDtinoD(Dn(OD()DOoDO)fO)opofh)feponphfoheplnehsnoetolonoslosptplortrsoptdopruorpcocdreduoucadecruoeacmr change during oxidation with DTG profiles are shown in Figure 5. The weight loss below 200 °C may The TGA measurement was carried out to investigate the deposition of the oyornxgxexayeaytngsgigoeaesntniaoat(aotDtntiioDo(3nDn.O6(D(%D)DOoDf)a)OtcOpoa)h)f7)teo2opaonf3fhlfoypepKlsnhshtoe.et=nlnonTsop1htlolsrsi.so0tpttdororwueopcsdtdr.uerouol%dcacdtdereuiocPmcacmertepo/oaZlamtrirrieo-ocoa5smth7itacay,hatdtahWhiicrtyco/hdhthFchyryayoeodr=dcbrarao7ocrcnct5baisaovor.grbnbinbTtcosesoeoyaoh.ntnon·niTeTosnheso.hfheo/.ntTitmTethTshteihoheseohoetleiehteulrstchmhoeoeoetet-nthutcrhcherepoceslorlurocereuplod,pluTelrpdein=lndergdi6rnis7ngrai3gtntsugaKsrtaus,tauiriPoatruHtnanir2t/oairon=atainp/por2/ianrdpa/MrpidadiePpdhdiadyde)d.dhedrhryeaydhtdiriyoardntanirt/oaihontyin/odh/nrhryo/ydhgdryeordnogrageotneigonaoetnanitoai(ontHinoY(YnH(D be attributed to the removal of water and residual organics absorbed on the catalyst. The weight loss spent catalyst. The weight change during oxidation with DTG profiles are shown in uruntrerir/aoasratnsnantieipo/ordinand/p/rbrridiayadpephidmidydeedhdtryehaehdhathiyrynyoadodntrlir/a.oahatntyCiio/odohonrnym/o//hdhgpyryeoaodndrgrearoeodtngigoaewentniiaoat(tnhnHtiioY(cnHnoD(Y-Y(H)fHeDYtYeYo)dDitptno)o)r)gotptodormuopcdedrertouohdcdcdaeuynucoceTlTeylyo,hchcpcTlelyteyayohTchcrcpsesalhleTeloeaofoecbrhfrpspaiaoeaeansafnrcerfsfrsadadzoici.aenfeonfcfspspfnidio.inanaedntstspsh.d.pa. taiphntahvitonhilnlvivoneolsvsvlovetlhshevesethstihentetheienerirnmtmeitnremtrdemieramdetedeieaidtpapeitraeoptdepruorpcocdrtduoucdtycyutclyctoychchlcyeolxcxohlaheonxehoxaelnaxnoaolrnlosorlurbos above 200 °C may be attributed to the combusti ̋on of coke deposited on catalyst surface [43]. Obviously, The TGA measurement was carried out to investigate the deposition of the spent catalyst. The weight t.e0inr7mt%erermdtioeadt0ei.a0pte%eropdaruotocd5tu7c3ytcKclyocahlneodxhaefnxroalmnolr13os.ur8b%ssutbitsouttie1tud1t.e5cdy%clyaocthle7ox2ha3esnxtoKauaslnd).tso,oyutIlus,dwn.tdytuhIhty,dnhie,ltyierhst,ehetitirehishsesreriuseinsduisuentnduedenctetdeatecebtcleatecbatblaelmbealoemaumanomotuunontuftnomotffeomtfmheymtelhtcehytylhclylycolychlcyeolcxohlaheonxehoxaelnaxnoianolnloitnhilneitnhtphertehopedpr thienetieinrtmterermdieadtieiiatpteropdrrouodcdtuctytclyochlloeoxhaenxoanlnolrlosorurbsusutbibtsuttititetudttecdyclyochlloeosxhthuaednxyoan,ln.otoIhlln.e.IrItInenhniitstshiiusndetectable amount of methylcyclohexanol in the prod Figure 5. The weight loss below 200 C may be attributed to the removal of water the weight loss (0.8 wt. %) below 200 °C is just 14.5% of the total weight loss (5.5 wt. ̋%), indicating change during oxidation with DTG profiles are shown in Figure 5. The weight loss below 200 °C may o(mufrnotumnotf9o.om8f%emthteyotlhc1y5lc.c1lyo%chleoaxhtae5nx7oa3lnoiKnl aitnhnedthfperropmdruo3cd9tus.c,c9t%ism, tpiomly4pi2nly.g9in%tghatrthteata7rhtce2retaet3tihrocaDeKetcnaiDto)ciDrDo.nOotiDnDTuortohnOreouisrumtoetueamtiemnalmiaynianloyilcnycoluyocrcosuccudrcsrusrdridusnurgdirnuitnghrigenthgtmhet-ehmcemr-ecm-srcoe-rlcseroHseolDslHoOHlDHDpODOropOcpreorpsocsrecoseucsnesdusuensrndudetnhrederteh emaomuonoutunontft omffemtheytthlhcyllclyochlloeoxhaenxoanlnoionll itinhnetthperopdrrouodcdtusc,cttsism,, ipimlypilnlygiinrtghgeattcthtatiahtottentthrDeoeDuDtOeDmOainly occurs during the m-cresol HDO process under the and residual organics absorbed on the catalyst. The weight loss above 200 C may be that coke deposition might be one reason for the catalyst deactivation under the experimental conditions. ersunusmdrgrdiunuetrhgtrihientyghghmgleat-ththcmhmiebeore-e-enmcsmroa-e-clctfcstrHorbeilsesDbsoHoHnouOlzlDtHeHeHpnOdDreDoOptOtcororeopsptcrshroreoeluscucsneredsueunsemnesru.duotneTnhvrdhdeaetehlrtrremtotsththtfetsdswhteyecasdldsotattentcecrdidodoiancnctcniodonidintfdidsoritiiteotn(tiWpsilosouind/(=(/neWFspsunsW2(e/(a=(pFWp/lpMcF27=7=o/=o=FP5=MurM2ag72lg=g,d7P5PaMcM5na7bgtP·,·Pi5ePcghchaca/st/g,a·,m,thc·aho/otbm·/lhmscor/oemolsrcolbrolce,resleoHcdslro,e2ls,/Ho/oclHn,2r/eH2cts/shrc2oe/relcsero=sceolas5l=to)a=l.l5T=yT)5.sh)h5t.Te.)Trh.eTeheTfhreohererefeorfw,eorafereol,eikr,gaealahn,nklteaekaslsnlakoneiansnsensitetnhisnetihnptpherteohpdepruorpcocd ̋ indicating that coke deposition might be one reason for the catalyst deactivation attributed to the combustion of coke deposited on catalyst surface [43]. Obviously, the weightloss(0.8wt.%10)5below200 Cisjust14.5%ofthetotalweightloss(5.5wt.%), roe/eclxsr=oyels5eo=n)l.e5=Ts).hs5eaTeT)lb.rheoTcefvtrorhierevferio2,etyr0faeo,l0,ikr.ea°e,lCn.k,aeatlmshnkeieansnpye-tih/nsnbmeit-nhpaxertyohtplprdeirbnuopecudrtotusedcdmltuesctacomtmytsivtabmhiyeteaybgyc(eoabngmerbnangnaxueterirnshmadteytitredueoedhfadrdrmhryntoeydhfmogdodryefeofrfdntomgmc2rhragoeo4oetnemtkti.gih0honoae%entantnihdtoaoioeontfipnotonofslftuoiotefeolnutdloeue.lo.neune.enc.ea.talyst surface [43]. Obviously, 22//crresoll = 5)).. Therrefforre,, allkanes iin tthe prroductts may be generratted ffrrom tthe as that withthouetwmeeitghhatnolols(sa (m0a.8xiwmtu.m%o)fb1e6l.o7w%2a0t069°8CKis).jMusotr1eo4v.5e%r, thoef the total weight loss (5.5 wt. %), indicating oyoxlxeynlloenlnsoallsnsdanmndemtheytthlhaynlliasnoniliseso[lle3e1[[3]3;1(]2];;)((2m2))emtheytthlhaytlillaoatntiionfnobo1feff9nb9bzeCenzentwnoeiwgtwhiivitmtthehetmtohleauttnheh 100 2.22.2.C2.2.a.Ct2taC.alaCtyataiailcytlatyHiltcyiyctHdicHryoHdydryeordodrxdeoyoedgoxeyxongyxageytneginoaoeantnitoaiaontninodananMndadenMtdMheyMtelhataehyttilyihoaolyatniltoaoiontfinomomnof-fCmComfr-eCem-sCsr-oerClserosevolvselorovlePvPoretv/r/PeZ s also another reaction to produce p-/m-xylene. Similarly, the further that coke deposition might be one reason for the catalyst deactivation under the experimental conditions. under the experimental conditions. oantioandanMdeMtheytlhaytiloantionf mof-Cmr-eCsroelsovleorvPert/PZt-t/5Z7-57 gaentniaoatntiioanadanMdeMtheyttlhaytlilaoatntiionf omoff-mCm-r--CeCsroelsolvlleorvePert/PZPt-t/5/Z7--57 5.5% takes place which can be demonstrated by the increa ding methanol (i.e., from 2.8% without meth4a6nCol to 5.3% with methanol ngioaentniaoatniodanMdaneMdtheMytlhaeytihloayntliaoatntiomant-Cmamtr-emCs-roCels/rMoels/eoMtlh/eMatnheoatlnhMoanloMllaoMrlRaoralaRtRiroaRtoiaofti1o/f1o1f/1/1 ygenattiion and Metthyllattiion att m--Crresoll//Metthanoll Mollarr Rattiio off 1//1 95 105 2.2.1. Catalytic hydrodeoxygenation and Methylation at m-Cresol/Methan o -0.01 100 0.00 se of polyalkylated isaormu-uicsoserumtehseyomtlhaeysttielhloalynetilicoaortetniavorcienetaiairoecenstaisocoaotnrniefsosrnoesfbfarorsceftarcncveteasdcnottafrsrniontsmrteioinr0mtie.en1ertm%deireamadtenieasadtmeie0asa.t9emys%oamyctcaouycr0(co1a.uc0)s)r(rc%m1mf(auao1)sre(la)mlaf1ftonohomhs)ewdlyfmlteololhs0tal:wewhy.lt4toiyilshoa%wl:yntanisltoa:oiontfinococrnrofefcosrcoferlcseirosneoltsiolonilxntoiytnolxteoxynylxoelylneslnoeaolnsnlodsdalnasmndaednmthdmheymtelhtaehyntylhiaslsynaolnilaseinos[oil3selo1e[l]3[e;31([1]23;])1;(m2]m(;2)e()m2thmh)eymtelhtaehy varriiousmetthyllattiionrreacttiionsoffrreacttanttsorriintterrmediiattesmayoccurrasffolllows:: 5.5% ey3nl.oe3eln%soaltnsoda1nm.d1e%mtheyatlnhadynli1as.no6il%seo[la3et1[7]3;21(3]2;)K(m2.)Temtheyrtlhehaytailroaentisoenfvboeoerfanblzerenen 95 o 85 onanleno[ol3ll6]; (3) methylation of toluene producing xylenes (o-, m- a o 4 4 750 757050750 FigFuigreur4e. E4.ffEefcfteocft otifmteimoen ostnresatmreaomn (oan) t(hae) Ftmhig-geFcuFirmrgreiFegeu-sciuorg1rlereu.ecsr1Eoe1.fnlf.fE1vceE.foecfrtEnefsocveofifotcfetnrorcrseoeftaiafonorcendrftaeidroacoaetncnaiotodcitxonetediynmotgenptpoemenxtmrepayampetgteureupeadrnetaeuprtauroteotrenuedor(u(eonacn)ot(nat(tha)(e)athtc)cheotehncevoceoencrnvosveiniorevsnrneisoriaosninoda cat cresol 2 62500656050650 300700 707000740 Timeonstream(min) 0.00 o 199 C 22.2.2.1.21. .C1C.ataCatalaytlaytiltcyicthichyydhdryordodrdeooedoxexyoygxgeynegnaetanitoaiontinoanandadnMdMeMtehtehytylhalytailtoaiontinoantatmamt-Cm-Cr-erCseroseols/lMo/Ml/eMteh 90 ByBcByoyB-cfocyeo-ecf-deofie-nfdegedienmidngeigmnthmgeamtenhtoehaltna,hnovaolan,lrvo,ivaol,rauvirsoaioumriusoesmuthmseymtelhtaehyttiylhoalytnailtoraieontainrocerntaeiorcaetnciatsocionotinsfosroneofsafrcoertfaearcanetctastncaotntasrtnsiontorstrieonri By co-feeding methanol, various methylation reactions of reactants or inter -0.02 zaesnonweneistwthofiomtgthrotieovtmgthtehogievastitgtovnehrileoeavatuolsnteoulonutlloleute:lne[un3ee6n[]3[e;36([6]3;]6);(]3m(;3)e()m3tmh)eymtelhtaehyttylihaolytaniltoaioontfinotonoflftuotefolnutloeuelnepunereeonpdperuorpocdriduonucdgicunixcngyignlxegxynylxelsynelne(eosen-s(e,o(smo-(,-om,a 573 C o -0.01 ieloarntsioinfntoflcutoreelnuseoenplseroapdnrudocdxiunycglienxngyolxlesynlvleisna(eoasn-(,oam-l,k-myaln-adati4npo6d-nCxpry-elxaeycnltei)onn[e3,)0r[,e3s(074p,–)3e3(3c47p7(t94)–o–i(])v3lp34;yep9o9)alo]l]ynply;lk;doyaylalanylknldadakydtlylekadlytaebltadetdnbezdbeenebnzeznsnezneaesensdaenaspndoadnlpydpoaolplylkoyaylaylklakytlyelkadlytaepltadehtdependphoheplnehsnoefolnrslosfmlrfsortofmhrmoetmhmthetemhtmheeymtelhtaehyttylihaolytan thlhaytlillaoatntiionf otoffltutoellnuenpnereopdrrouodcdiuncgiinxgyxlxeynllesne(eos-(,(om--,-,ma-n--danpd-xpy--xlxeynlle)ne[e3))(0[4[[3,3)30p7,,o3–3l737y–9–a3]3l3;k9ay]]n;l;adatnend benzenes and polyalkylated phenols from the methylation 80 -0.03 daornlpgpydoaplyHkoaylDlylkaOytleklaidyntlepatdhthepednhpoperlnhseoesfnlersonfmlcrseoftmrhooeftmthmetehmteheyamtnlhaeoytlihl.oayntAt9li0aotnsnf0imoxonyaflox1le0fyn0axlemeysn2olae0u0nsnndeatsnx3o0day0fmnlxedpeyeynmo4txloh0mhely0eylananmstleanohoetwloeonhlal5ks0tlnoaiy0h,twnolhlarsaolein,twtls6seoh,r0pdie0lrte,esehcrpset7peis0vce0petceiltlvcyiy8vet.0ile0vyley. l.9y0.0 andpollyallkyllattedphenollsffrromtthemetthyllattiionoffxyllenesandxyllenollswiitth Weight (%) Weight (%) dW/dT (%/oC) dW/dT (%/oC) Selectivity (%) Selectivity (%) Selectivity (%) Selectivity(%) Selectivity (%) Selectivity (%) Selectivity (%) Sellecttiiviitty(%) Selectivity (%SS)eellectivity((%)) Selectivity (%) Selectivity (%) Sellecttiiviitty(%) Selectivity (%) Selectivity (%) Selectivity (%) attioioiof o1of/f1)//1i1s))piisrsepsrerenstendtteaeadsds asfauauanffucutnicoctntiionf otoeffmttepmerpaetrurartetur(r(resese(e(seFeigFuiigrgeur2r2re)e).2)).. Temperature (oC) observed compared with negligible amount in the absence of methanol, CaCtaCalytyaCatailaicyctlaythiltcyiyctdhirchryoydhdryeordodrxdeoyoedgogxeexeyonygxageytneigionaoetnanitoaiaontnindodanamndaedenmtdhmheymtelhtaehyttiylihoaolytnaniltoaiontfinomnof-fcmcormrf-ecm-srcoe-rlcsewrowseoleslwrorewelecwrecearaercraeciera caondamryetmhyeltahtyiolantiofnmo-fcxryesleonlowlse.re carrie8d5 out to examine the possible iaotnioandanmdemtheythlaytliaotnioonfomf-mcr-ecsroelsowlewrercearcraierrdieoduotutot teoxaemxaimneifnftehfeceftftehefpcefeoftcepfsftcsoitimsmofbsfloeiembtfthmhleamtenhtoeohatlnahnoaolnlolonthnoetnhthestehlseescletesilvevcelteceitvcivectioeovncevoceoencrnvosveinorevsnrneisoriosnininotiononintopiptno-t/pomp--/-xmpx/my-y-/lxm-exyn-ylxel.y.nelneT. nattiion and metthyllattiion off m--crresoll werre carrriied outt tto examiine tthe possiiblle Figure 5. TGA profiles of the spent 1.0 wt. % Pt/Z-57 catalysts. 573 oC heseseoecfltseismevceletetleietcvchctctetaioivnvnecoevolencicrnovosonentinhorvseneieroHrrsnisiDiniotOnoinotiopinfn-tmt/topmpo--c-/pxrmpe-y-/-/s/lmxomeyln--xlxbexey.rynilnleTe.gnheseTeT.e.hvTpeThrhoaepeldrnuopepcdrwtrouodcdrdtueuicascdtcttritmisibdotd-rurincmicsistsbsrmtrtit-re,reourcim-sisinbtbrcnboioieu-uoroculcset/t/n(ltirmoimsuaioeoltdnes/ne(lnmiota/atnhmhlteg(/(a(amtaenanhttoeohatlnahmnomaolnolmolmalormolrarlaoratlririaoartaoiortoafifoto1iof/1f1o)1/f1i/s1)/p)pi1sri)espsisprsernpsetresenedsnteatndestdeadsafsuauanasnfcuaftunifoncountcnitocoiontfinotenofmftoeptpfmetmrep 80 -0.03 u1e/n1e),isasprweseellnatesdxaysleanfeusnacntidonotohfetrecmopmepraotunreds(,sewehFicighuorebv2i)o.usly improve 0 100 200 300 400 500 600 700 800 900 ne by 44%, possibly through direct methylation of toluene ando HDO Temperature ( C) Figure 5. TGAprofifillessoffttheesspentt1.0.0wtt..%PPt/t/Z-57caattallysstts.. 214 -0.02PDF Image | Zeolite Catalysis
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