Zeolite Catalysis

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Zeolite Catalysis ( zeolite-catalysis )

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omuonutsn.ts. 100 (a) 5 5 5 5 100100100 100 100 100 5 (b) ( a ) ( a ) ( a ) ( a ) ( a ) ( (a a) ) 5 5 5 5 5 5 ( b )( b ) ( b ) ( b ) ( b ) ( (b b) ) 444 44 4 333 3 3 3 222 2 2 2 111 1 1 1 44 33 22 11 00 600 550 60 40 20 44 33 22 11 60 60 60 2020 20 20 650 600 750770500700 550 750750 600550550 Temperature (K) TemTpeemrTapteumrraeptue(rKrea)t(uKre) (KT)emperaTteumrep(eKra)turTeTe(emKmp)peTerreatmturpre((rKa)t)ure (K) 750700700 750750 TempeTraetmurpee(rKat)ure (TKe)mperature (K) Temperature (K) Temperatu dominates, and H2 availability on the catalyst surface decreases with the increasing temperature leading to the rapid decrease of alkanes selectivity [33]. As a result, the aromatic compounds selectivity increases. At the same time, the increase of isomerization, transmethylation, and demethylation activities of m-cresol over acid sites causes more o-cresol, xylenols (2,5-xylenol, 2,3-xylenol, and 3,4-xylenol) and phenol (0.9%, 0.0%, and 0.1% at 573 K to 3.3%, 2.1%, and 4.0% at 723 K). The amount Catalysts 2016, 6 CaCtaCltyasltytaslty2ss02t1sC0621a,06t6a1,Cl6y,as6tasl2y0sCt1asa6t2,a06ly1ys6t,s62016,6 4 of polyalkylated phenols is tiny in the temperature range of 573 K–723 K. Except 000 550 600 700 650 650600600 0 0 0 650550550550 0 000000 0 0 0 550 600 6550550550 6700650500600 550 6570560650505650500 600 70076050607000 650 44444 alkanes, aromatics, and phenolics, other products such as indane, naphthalene, and Except alkanes, aromatics, and phenolics, other products such as indane, naphthalene, and their derivatives, also exist in small amounts. ExEcxeEcpxetpcetaplkatalknaEaelknxsae,cnsea,Eeprsxtoa,crmaoealpamrktotaEiEamcntxaxsielac,ckstese,ia,pcpntastaed,rnsoa,adlmlpknkahadaprentnohinecepmeoshn,l,aeiotcanliasicronrc,osolds,mimo,ctasapaho,nthtetidhcecrosnest,phr,ophelraiporecnrdnsdodpuo,drclopuioptcsdhcthshute,sesncnurtosctlulphicscresouhsra,dcshupaocsritonhtahsdiesenruarsdnicunaptpecsdnr,rhoaeosdn,duauaeuncsp,chathtsnpistnhahadspatsuhaulhencacitnhleheda,n,laensan,aenep,iaid,n their derivatives, also exist in small amounts. c,tsothsuerchpraosduincdtsanseu,chnaapshthinadleane, annadpehrtihvdeaeiltreiivnveas,t,ivadelnsesdo,riaevtlhxaseitosivtreeixnsi,sdstaemelirsrniaiovlslaemtatximavivslelotsuai,nmnatlslosm.ouonaeltxlsx.iaismtioinusnsmtsa.allamounts. dtphheperhneopnlriocdlsi,uccso,tsthoesthruecprhropadrsoudciutnscdtasnuecs,uhcnhaspahistnhdiadnaledenrnaeivne,a,ent,iavnpedahspt,htahatlhlseeoiadnrlexrn,ievsa,atntiadinvnesdthsm,etahirlelsioarmexoiusnttisn.smallamounts. (b) (b)(b)80(b)(b) 808080 8080 804 3 40 40 40 2 1 Selectivity (%) Selectivity (%) Selectivity (%) Selectivity (%) Selectivity (%) Selectivity (%) Selectivity (%) Selectivity (%) Selectivity (%) Selectivity (%) Selectivity (%) Selectivity (%) Selectivity (%) Selectivity (%) Selectivity (%) Selectivity (%) Selectivity (%) Selectivity (%) 750 700 700650650 750 60 60 60 40 40 40 20 2020 700600650500600 550756050665050505650500 600 70076050607000 650 7507750605750500 700 75700 750 750 K) Temperature (K)TempTermatpuerera(tKur)e (KT)emTpeemrapteuraetu(Kre)(K) FigFuigreur1e. 1E.fEfefcfetcotforferaFeciatFgicouitgFniruoiegtrneu1emt.r1epEm.ef1EfFrp.eafiecEftgeutrfucrafoFretetfecuiogotrf1ueneo.arfe(coEeaFtFrnfice)1ifoitgae.g(nitcuacohuEt)nrterifeoeotfemtchenfe1oc1epmr.tn.ecEpvoEarmoaefcfnftprtfureaiseveocrticruaeoentatcrnrtoeotusiefnfiaromoenrnrn(enedpaoatae()neacadrmtntat)ei(hitodaopeutn)hnxerdcereytatohegectoneomumeonvxrncnpeyao(vereatgnorsere)aivarendotstenunuih(ropraresenareti)oencoaotdndodhnuneadcv(neacteado)r)exsndtoityhvohexgeneoyerxgcsncayioeonaogntndneavdntdeaearenrdpstsodeirioxpoddnyrdnoepguadoarecnouxn ucoroenno(vane)r(staiho)enthcaoendcvoednrevsoieoxrnsypigoarenondautndedcedtodpxderyiosgxdteryunigcbaetutentdaiotepndrioasdpdtnirusdoditcbirdtsui(ubtbtrciui)otbtniouoxtnaiydonaigndsnetad(rnbindba()diubtsoet)(ridxboioby)nxpugdoyrateixigosnsoytedtdanrgnituibe(eababcduntnuet)tadtdpidtoer(inpxondbsrydt)aoapgrundnoirecbdoudxntudcya(d(utbgtbiecsde)o)dtnirnosodaiptxbxtirfresyuiryobtdogtgrdiuiemoeupbtnicruoaotmtnftidedreo-uodfidcnsrcmrotptpefrmrirsdmoboidumds-mlcuturiHr-cocimecbtnDsr-udeodcftOsilrirsosoeoHt.tlsnrmrioDiHbflurOmDuHot.-iOmiDoco.rnOemsf.f-rorcolrmeH: smDmo:ml-Om-c:cHcr.-rmrecDesrs-seOoco otnemtepmepraetruarteuroeno(na)(dati)hsettrhiceboucntovionenvrseiaronsnidoan(nbad)ndodexdoyexgoyexgnyeagnteadnteadpterpdordopudrcoutdcduticsttributionfromm-cresolHDO. :m-cresol udcfitsrotdrmisbturmitbi-ocunrteiofsrnolmfHromDm-Ocm.re-scorelsHolD:HmOmD-.-cOcrer.esosoll:cmo:c-ncomrcvneo-evscnreorovserlnisesoivrosnelnir,o,snio,cno,nvceo:rsnai:avollkeank:arl,ckascnaioanoleoknsenave,vs,nse,e,ers:i,ioanl,k:,:ab:naeeblnb:ksez,eabnenezn:eznesanzea,,lenlkn,ea:e,n,bees,n,:zbet:oneltne:uo:,zelteut:on:onelebuenl,ue,enen,znee:e,ent,eoe,l,:u:ep:tno-ep/l:mu,-/ep-m:nx-:/-eymtx,oloey-lxnulueye:nlnepen-,/em:-p eanteadtepdropdroudcutcdtisdtirsibtruicbtoiuontnivoefnrosfimronm,-mcr-ecsroels:oHlaDHlkODa.nOe.s, :m:-:mcrb-ecesrnoezlseonle, :toluene, :p-/m-xylene : bze:ntzeoe,lnue,ne, : to:lutoe:nlupee,-n/me,-xyle::nep-:-//mpm-/xm-yx:-lyxelnyeelneone-eox-yxoley-:xnleyen,l:en,oe-o,x-yxyl:eloenp:-noxepely,:yo,lpaleyolnokale-yl,xkxlayaylltkle:e:aeyndtnplepaeoda,t,oler:yoaldyarpmolaokamrlytokyialmcayat:slitlakc,eaptysdotio,clelalasydyt,raeaoldlakmkry:yaoalrlota:maoitctmhoeas:detd,athoritseacita,chrsrsoseo,,mrmsa,a:ticoc:sts,hp,::ehpre:oshnt,pehohnele,or:sn:l,olt,h:hepr:hs,eo,:n-opco:r-hlec,oesr-neoco:sl:r ,es, :b:ebneznenzen,e, :t:oltuoelunen,e, :p:-/pm-/-mxy-xleynlene :: o-xylene, : polyalkylated aromatics, : others, : phenol, : o-cresol; oathicesr,s, ::opthernso,l,other:s:p,hoe-cnroels,o:l;phe:no-lc,res:olx;y:l:exnoyo-lcesr,neos:losl,x;ylen:olpso,:l:yxpxaxyolykleyenlanalotk:lelysd,pl,aotpleyhdaelnkpoyhlls:e:a:.ntpoep(dloRosl.leypa(hclRlektkineyoyaolnalcalastei.etcodedond(nRpdcehioateicnontdonioilsltsns:i.o.npc(sRoR:=nedapaictt2it=ioionMns2:Pc caystle,adteadroamro:amotiatchtsie,crs,, :o:thpoehthresen,rosl,, :p::hpeohn-eocnrle,oslo,l;::ox:-ycolre-encsroells;o,l;:xy:lepnolys,alkylated:phoelnyoalsk.yl(aRtedactpihoennoclosn.d(iRtioeancst:iopn=con2ditMio : xylenols, : polyalkylated phenols. (Reaction conditions: p = 2 MPa, dap:t(oeRpldyheoaelpylcnkhatoiyelolklnsnay.otlelas(cdtR.oenedp(adRhcipetihnaoceontnlpsiso:.hclnsoep(.nRcdo(eo=Rilantsiced.otai2ni(tcoRiston:iMeonanspcPc:otaicn=,podni=td2icWoiotniW/nMo2Fsd:n/WPF=isMtap:/i=7,FoP5pn=7a=sg,5=:7cagp25tW·cah=gt2/·M/cFmha2t/PM·W=omMhal/P/co,7mFPrale5csao,or=ge,l,scWo7WraHlet,5s·/o2hHFl/g,/c2cm=H=r=/aect·o27sr7h/leo5c5c/srmlregoegs=oclscalao,la=5ttc·tlH,rh ̈he5=cs/h2/o,mam/l/5c,toar,oamHeltclcyasc2oarr/oseletcylstslaorsl=l=le,t,ysH=s15ot.2,l201,=/c=c.cHwa0r1r5etet.aws,0.s/locy%twc.lalsr%=t=ePa.=slt5%5yP/o,Z1,stlc/.tcP-0Z=a5a=tt-/7twa5Za51)l,lt7.y-.y.05)s%.7tw)=.Pt.1t1%/.Z0-Pw5wt7t/t.Z). .%-57P)t./Z-5 W/F = 75 gcat·h/molcresol, H2/cresol = 5, catalyst = 1.0 wt. % Pt/Z-57)c.resol 2 0, wcatt.a%lysPtt=/Z1-5.07)w. t. % Pt/Z-57). Hact2ra/elcysrosetlso=l15=.,05c,awtcata.lty%asltyP=st/1Z=c.-0a15t.7wa0)lt.yw.s%tt.=%Pt1/PZ.0t-/Z5w7-5t).7%). Pt/Z-57). GeGneGnreaenlrlaeylr,laylt,lhyGet,heectnhaecGetraeltclyanlatyletiya,rctaliGtyGlcHhlteyeiDHnc,necOeDtHrahraOateDalollfyOycyo,a,tofitotxctahohfylexyeHgoyteDicxcgcnayeO-tgnHacaelo-loDycynftot-OtiacncoiotxnaoHnHyiftnDgaDgioienOnOxngciy-nocogocgmofefonpcmot-oaxcxpmuiyoyongnpguidnetoenasngnudi-n-nsucidnonousdnmgnetudaparcnieiondrumienfdrpgfdgiefosdrfcuceieofunonrfmendmetndsrpceteonurcunutnodndndcnididefotdsfrisnioetdudrniueoinisntf Generally, the catalytic HDO of oxygen-containing compounds under different conditions using cno-mcopnotuainndisnguncdoemr pdoiuffnedrsenutncdoenrdditiifofenrdseinfuftsedircneiofgnfnetdriectnaiotadnlcisyfafsutetasrlieynisgtskcnaidstoiaifwflkfyenesrotestwnotntispctrakoaotnacaoplelywersosdtnctsettehioisdrsopkutkhrngnorohocweutengwndhototothrwerpoarucotgrcicehoeaenecdtdtwipotoathnhtrhropweuagtgcyhthsiwotan[w3yo4sop,a3[rtr35ehea4]wa.c,c3atTi5yioh]sn.e[Tp3poah4ante,the3hw5wop] Oonftoaofixnoyinxggyegnce-ocnmo-cnpotoaniutnaniidnsginucgnodcmeoprmodpuionfufdensrdeusnntudcndeodrifnefdreirftdefiienofrtnfesncretauntscatiolnycngdsodtinsiftfdieoisrtnieosnkntnusoscwiuanstngainlygtostsprioscekendowthnrotuoghprotwceoedretahcrtoiounghpatwthowaryeasct[i3o4n,3p5a].thTwhaeyson[3e different catalysts is known to proceed through two reaction pathways [34,35]. The one path is Generally, the catalytic HDO of oxygen-containing compounds under different eharoctuigohn tpwatohwreaaycstio[3n4,p3a5t]h.wTahyes [o3n4e,3hp5ya]d.thrhToygihsdernoglneyenshioyspldyaortsrhoidsgieorsnercodtlihyhdreysyeicdodstrxrodoyrgegoedenxinroyoealgcltyietosndinisaest(oioDoxrnyDdgi(OireDren)cDcaottOfdidope)enohoxe(xfDnypogDhlesOnta)otioliposofrntopo(dh(DpDuerncDoeodOlaus)r)ctoemfapaprhtohoiemcednuhaoctylielsdcsarthoroyocpdmaroaobodtdociuacuncrcshbe.eyoTadnrhrso opurgophcroetecwdeoedthrertohaucrotgiuhognhtwptoawthorwearaceytasicotn[io3n4p,a3pt5ha]wt.hawTyhahsyyed[sr3o4[ng3,e34n5,po3].al5yt]Ths.ihsTieshohyreodnrioeornegepcetanptdohaeltoyhixsiysigsoerndaitrioecnt(dDeDoxOy)goefnapthioeno(lDs DtoOp)rodfupchenaroolsmtaotipcrohdyudcroecarrobmonasti.cT hydrogenolysis or direct deoxygenation (DDO) of phenols to produce aromatic hydrocarbons. The other conditions using different catalysts is known to proceed through two reaction DtOof)porhfoedpnuhocelensoatolrsoptmrooapdtriucocdheuyacdrerooamcroartmibcaohtniycs.dhTryohdoceranoroebcntoahoiesrnenbirestsoh.inetTshshce.teohTcoueohonptecuheloepoeiudlortsehpndretleihernrdeigisncrgostoiohanustegeuaprtclsiuaesoastrdtuiatutohphtrnielieaoen/trndcgicao/oprnsuauia/pndprtlgaiuledeprdsdeaidadhtrietryiouidhndnreygagr/hdartisaytrsoiapadontitrunidu/aor/rtahnadiapoty/teihindohody/rnynhdod/d/yrgreroadaeahpgprntyoieiadodgntnrieadoad/ntehtnieaiohyhotn(ydiynHodrd/(nohrYHragya(DtYetdHionr)oDYonant)gt/oD/iheoty)onypndadrtporot(rioHrodogpgunYderecounDne(dcaHa)cuetYiyctocoecDnylpoc)(ryplHtoacopYdYrl eantiaotnio(nD(DOD)Oo)fopfhpehneonlsotlos tporopdroudcuecaeroamroamtiactihcyhdyrodcroarcbaorbnos.nTs.hTehoethoethrer one is the coupled ring saturation/rapid dehydration/hydrogenation (HYD) to produce cycloparaffins. pathways [34,35]. The one path is hydrogenolysis or direct deoxygenation (DDO) horyagdteironanati/tohionyn/dhr(yoHdgYreonDgae)tinotaontipo(rHnoYd(HuDcY)eDtco)ypctolropdrauTorcadheTfuefhciTnesyeehscsc.eleoyocspcnoeladocnrpoadpTfanafhrpdtiahneafptsfhTsi.ainenhtvichseno.vinlsnvoedvelTcTvsopohehlanetvsehtdehetshepeieictncanhotvtihenenodrtdlimevnrpeptvemeasaodrtetlimhthvadhteieieiansdntivivepntaohortpolelvrdroempieunsdsrcetoutetdtdhchricutmeaeyctcecietiyndlnoctpiteahyelrortrocememhlxdoeaupehxdncdreaoiotiaxnadlctaotueyeonlcroptpollrosrcouohoysdbdercusuxlbstcocaiusthntbuiecoctstxyleuytiacdtcotenlulrodocotheyhslceduceoyxlbxorcasahylntnsoiecoutohxlulbloeatsohxeontdreairotxnulsca.outuyne o/rna/praidpidedheyhdyradtriaotnio/hny/hdyrodgroegneantiaotnio(nH(YHDY)Dt)o tporopdroudcuecceycylocploaprafrfaifnfsi.ns. The second path involves the intermediate product cyclohexanol or substituted cyclohexanol. In this hperxoadnuoclt ocyrcsluobhsetxitauntoedl ocrycsluobhsetixtaunteodl.scItyuncdltysoht,hiusetdhxyea,rnetohlise.struIeudnnyistd,heutithsneecdrteastbtetiulcsedtayuyab,n,mldtethoehetuaeermrnecettoaiousbsfnlueutmnoadedfmetehtmtoeyeucelctntahytbycoleofcyhamacemlxeoatohnueyonxltcayiononcfofllotmhienetxhphtahyrynoelcodcyplyucrciolnltodsh,huthecimxextsap,pnlrioyomlildnpiuignlncytitshnh,ageitmptpthrhpraoel oenrdtmeurcemtdeicadyticealtopehroepdxrouadncutoclctyocryloscuhlobehsxteaixtnuaotnleodolrcoysrucblsoushtbiuestduxtiytateun,dtotehlcd.eyrIcenylocithshloeiushxtneaudxndeaoytnl,e.octIlth.naebIrtnleheitsihasimsuonudneteocftamblethaymlcoyucnltohoefxmaneothlyinlcythcelohperoxdauncotls,inimthpelypinrogdtuhcatts,t of phenols to produce aromatic hydrocarbons. The other one is the coupled ring study, there is undetectable amount of methylcyclohexanol in the products, implying that the DDO nthoyllcinyctlhoehepxraondoulscatisnt,utihmraeptlpiyoriondg/ucrthtasap,titmdhrepedlaDyeciDnthriegoOyancdthtriraoatuntiehroemanucDta/etiiDnhomlnOyadrionorcluorcyrteuegaoarcemcsctcntidaiuoauirnrtslirynrdoguonurctiehecn(eugmHmrmstaYhi-idnecnDulrlmyery)is-noctgclrocecHtushuporDerslrOmdHodu-udpDcriuiOonencsgpoetrslthosHcecuyeDmnscOds-lcecourprpenertsdsohaoecerlreatHsHtefhsfiDetuenOntdesdsp.pcetrorerondtchdeceisostsistnoeudunsnitnstedid(doepnrcs=oth(n2ep muloncuytncoltfoohmfexemtahneytohllcyyilncylotchleoehxpearxnoaodnluocilntsi,tnhiemthpelryopidrnourgdecauttschc,tatisitom,ntihpmreloypuiDlntyeDginmOtgrhaeaiatnhtclatyithoeotnhcDercouDursOtDedOmuraiinnglythoecmcu-rcsredsuorlinHgDthOepmro-cressoulnHdDerOthperotecsetsesducnodnedrithioentses(pte=d reaction route mainly occurs during the m-cresol HDO process under the tested conditions (p = 2 MPa, orceessosl HunDdOer pthroecteTsshteuedncsdoenrcdothinteiodtnespt(eapdt=hcoW2inn/MdFvitWPio=oa/ln,F7vs5e=(sgp7ca=t5Wth·h2ge//FcmMati·=onPhl/tac7mer,e5rsomgl,WcWraHet/s·/Fod2hFl/,/cim=aHreto27s7e/l5oc5crlrpegegs=ocrscalao,t5t·lHdh)h.=/2umT/c5chor)tel.lcsrcTreoeyshfslolecl,=,rleHeHo5,f2h)2oa/./crleckTerxe,aehasnaseonelrklseloa=f=inolner5oest)h,.r.ieanTslphkhtuhreaeobrenredespfufstorciorirtnesdu,utmtahaceletakdksyapamnrboeaesdsyguibencnnettstehgrmeatnapeyrdrroabdfdterueuo norgilntHghDethOme-mpcr-oecscroelssoHluDHnOdDeOprrtophceroetscesesstuesndudnceodrnethrdeitthitWoens/ttFesesd(=tpecd7=o5cn2odgniMctadito·Pithnai/oWs,mn(/sopFl(c=p=res2=o7l,5M2HgPM2ca/Ptc,·rhae,/smooll=cre5so)l.,THh2e/crreefsoorel,=al5k)a.nTehseirneftohre,parolkdauncetsimnatyhebeprgoednuecrtastemda W/F = 75 gcat·h/molcresol, H2/cresol = 5). Therefore, alkanes in the products may be generated from the esreifnotrhee, aplrkoadnuecstsicnymtchalyeohpbreoxgdaeuncetosralm.teIadnyfbrthoheymidgsrehtosnhygteduerrnadotaegytdie,onhtfnarhyotodiemofrnoteotgohlieufesnetauontelinhuo.ydyendndeorerotof.egtceoetnlnauaebtiniloen. aomf toluenenteo. f methylcyclohexanol in flso=rle5=, )a.5lTk).ahTneehresefrioenrfeoth,rea,lpkaralokndaeunsceitsns itmnheathyperbopedrogudecnhutseycrtmdsartaomeygdaebyfneraobgtmeieogntehonrehafeytrtedaodtrleoufdgeronefmnero.amtihoetnheof toluene. hydrogenation of toluene. the products, implying that the DDO reaction route mainly occurs during the m-cresol 2.2.2C..a2Ct.aCltyatltiyact2liHy.c2tyiH.cdC2yrH.dao2yrtd.aodeCldroyoaetx2idotyc.a.ex2g2lHoy.ey.gxntCyCiyeadcagnatrtHieatoaoantdlynilayoydetatnoriconocxandyHngeaMdyoeyndndxMedryartohgetMdidyteohelnenayotathlxaxtiayiyoyntolgnigdanoetonMinaofanoenmtdfitioho-omMCnyfn-lrmeCaetn-rnhsiCedodysnlrlMoaMeoltsveieofoetlhmvnhroey-PolrvClafteP/trtrmZieito/-Ps-Zn5nCot-7/lor5oZoef7f-svm5moe7-lr-CoPrvrte/sZsro-Pl5l to7o/vZve-r5r7Pt HDO process under the tested conditions (p = 2 MPa, W/F = 75 g ̈ h/mol , 2.2. Catalytic Hydrodeoxygenation and Methylation of m-Cresol over Pt/Z-57 cat cresol Chyrleastoiol novoefrmP-tC/Zr-e5s7ol over Pt/Z-57 naiotainonnadnoMdf eMmth-eCythlrayetlsiaotnlionvfeomrf-PmCt-/rCZe-sr5oe7lsolvoervePrt/PZt-/5Z7-57 H /cresol = 5). Therefore, alkanes in the products may be generated from the 2 2.2.12..2C.a1t.aClyat2tiac.2lyh.1tyi.dcCrhoaydtdaelro2y2ox.t.d2i2yce.g1o1he.x.ynCyCdagatarietotoandnlayeytaotinoxcdnyhgMayendnedratohtMdidyoelenoaotthxaiyonylgndgaetaMnintoaemntitioh-aoCtnynlrmaeant-sniCododlrnM/eMsaeoetetltmht/hMy-alClnaeartotiehilosaMnonloa/aoMltlaMmer-t-oRhClarnetreiosoRoloaolMl/tfMiMo1ele/oa1thrfhaR1a 2.2.1.Catalytic2h.y2d.1ro.dCeaotxalyygteicnahtyiodnroadnedoxMyegtehnyaltaitoinonanadtmM-Cetrheysloalt/iMonetahtamno-ClrMesoolla/rMReatthiaonofl1M/1 2.2h.1y.dCraotagleynticathioydnrodfetoxlyugeneat.ion and Methylation at m-Cresol/Methanol Molar Ratio of 1/1 yeao-tlCnhiaotyrainelonasnadotniloaM/dtMneMmaetht-teChymthalra-neyCtsoliaorletlnMi/soMoanolte/lamMathtr-aemCRnth-raoCeatlisnroMoeolsol/oMfMla/1eMro/t1lRheaatrahntRiaonal toMilof oM1ol/af1or1laR/r1aRtiaotiof o1f/1/1 ByBcyBoc-yofe-cefoed-eifndegieBndmgyinemcgtohBem-atyfhneacoetnhodl,oa-ivfnlBe,agoevyryldmia,cocirvoneuioao-tgs-rhfufimemeaosenuemedostihihlenmn,ytagvghlneaymtotrhliliaeoey,otvnliuhaoasaratnreinmnioaroneceula,t,rsihcvevomytanilcroresaitinotiohiosuoufynosnsrlsfeamraorteiecfeoatrcnhahcetnytyiaraotelclsananattoatcsisionrtoiontionfsnrnrtoiesenraratoimcecnftrtitearmioeoednrnaenitmsascdstieoeadfrsnftieritrmanesetataeaomecsyrtatmamiaoynceattoetcdsyscruiomacorrturcaeircisndnuaftimtsreaoe orenacrcettiaocntsisoonfrsrioenaftecrretmanBcetsydainocatrotsei-onsftremeirnadmtyienerogdmcimcaeutderistahtmseafsna(o1yoml()lo1ao,mcyv)w(c1aemousr)t:crhiemocaytuhuselraystfahtolmiasylo(ltef1lonioaot)whtolnmilysfo(o:lwecn1aftr)tsoheci:mofysreonlceaslrtr(ote(ihei1nlsoya)o)tinclonmlamttoitxoeniefyotntxchlonhseyryenxollesaoyfaontlctrilseoieronileansnoscntoaoltodsanlfnxmadicntynrsermteldeoteoshsenmroxoytohilylelnlayilitsntenhnleatantyirosnomloaidxlxslenyeomdials[eineo3andtt[l1hoeoe3m]ylsl1;[sl3em](a;2t1nhan()]i2dy;dsm)lo(moam2emlcne)techiet[mstuhyt3hohryel1ylayatel]lhtalsa;ia[nyon(f3ti2loni1saos)lo]tolnmi;olfoe(eowebn2f[tes)3oh3b:nm1fy1ez]l]bne;a;eztn(t(hnei2e2oynz)wnlemamnoiwtteiefhoitwbthnhmheyionteml umsemtheythlaytliaotniornearcetaicotniosnosf orefarcetacnttasnotsr oinrtienrtmeremdieadtieastemsamyaoyccoucrcuasr afoslflolwlosw: s: 3e1t]h;y(l2a)nmiseotlhey[l3(a1t)i]o;mn(2eo)tfhmbyelatnhtziyoelnaetoiwofnictrohefmsbotelontihzgnaeittnvonoexgltwyoivlieuethnetonomtlelosue[tgea3hnin6avedn]e;[om3t(lo36el)]ut;hmet(oyno3eleg)taghi[nmivy3viels6eaot]tht;oloieyo(lu3lun[ae)3etonmi1foe]ent;[o[t3(3hol26u6yf)]e]lt;a;mon(t(le3ieu3op)te)nhrmnmoyoeedlefaptuththrociyoyoilldnulnaugetocinixofieynbplgeoeornxnofeyzdtosloeuelnlc(unuoeiene-nws,ngeme(ixotp-hy-r,alomoenmdndeu-eutcpsachi-ni(anxodngy-op,lxel-mynxl-leye)alnen[en3dse0(p)(,o3o-[-x37-,y0–ml,3e3-9 nlyeolnlasonalisnsoadlnemd[em3t1he]yt;hl(ay2nl)aismnoileseoth[ley3l1[a3]t;1io(]2;n)(o2mf)ebmtehenytzhleayntlioeaotnwgioioivntfheobtmfeobnleuezthenenanzneon[wtl3eoi6wtgh];itvm(he3em)tohmelatuehnetaohnnlyeol[al3ti6o]n; (o3f)tmoleutehnyelaptriodnuocfintogluxeynlenperso(dou-c, imng- axnydlepn-exsy(loen-,em) [-3a0n,d37p–- 208 phdyoetphanlylheokaemlylnskloeafyrtlthlsoeaydmftrlepaodtthmhip(eoe4hntnmh)eooenplesfotmhxflrsyeyotlaflhmaerlotyknimtlyoehasnlteatiahotmnefndexmotxybhfeyleyxetlnhlneyazyneltelisomaonlatneseiemnostwodhneamfiatxntohxnehydfaytolhnxleplea,oynyonrloll,eoylnsrsnslmaep,eoawlserseknlpescitaydtehstwhnilmpcaxvadteinyteietcevoxhltteydhelyi,nv.lalpyreonemeh.mnlosyeolepe.n,wlteshrohcieawltatshsninpivoftoehrlco,l,ytmri.evesetphplyec.cmtiveethly.lation of xylenes and xylenols with methanol, respectively. CaCtaCltyatltiyactliyhctyihdcyCrhdoayrdtodaedlCroyoexatdoiytcexagolyheyxgyntCyCeidacgnatariteaohtoantdylnilayoedytaotnrtionoxcadnynhegmadyoyendxdnemdryrtaohoegtmdiytdeohelenayotoahtlxiatayoiynytolnigdgaoneteonminanofanoaenmtdftiho-omcyfnr-lemecatsrtn-hnieocodydslrnloemwamlsotoeiwefotrlthmenhwyryc-oelelcafarcrtetemiraioisorce-onrnacdilrerorewodfifsueomdtrule-t-otowcurtreoaeterxrsteroaoixlmecleadawixmrnoeareirmurnetedihcntcetoaeahurpertrtohx elsaotilowneorfemca-crrieesdolowutetroe ecxaarrmieidneouthtetopeoefxsfesaicmebtflifeneoecftthmoefeptfhofmeascnseitobhllaoenfoonlmefteofhftenehecatntshoeoelfecsomtmenilveetcthtaiacevnoeonslvecleoeorcnsntiviovetnthrehseiiocnnsosteoenlvienecpctrt-tois/ivmvioep-nx-/cycmoiolnen-ntxnvoveye.lrepsniT-io/oehmn.ne-xTinypnhtlrteoeondepup.rc-o/t/mTdmuhd-xcexistytlrlpedeirbniosuedt.t.riui ainonnadnomdfemth-eycthrlaeytslioaoltniwooCnefarometfa-clmcyar-rteicrcsireoehdlsyowodluerwtroetedorceaeorxcxrayiremgredieifenfnodeuacotihutooetnotpfeoaxoneamsdsxmeiabmtimhnleaeitfnhtfeoheylcetlhtapoetoionopsfnsotisbhmoslefiebmtlhsee-aclneroceltsiovolenwcetohrnevceasrersrlieioecndtivoienutoctopne-vx/emarms-xioiynlenitenh.teoTpophs-e/smibp-lrxeoydluencte. dTishtreibup nrvspie-o/rmnsi-oxinytloeintepo.-/mpT-h/xmey-lxpenyroeled.nueTc.theTdhipsetrroipbdruotcmidtou-mncdtr-imecs(sartd-reotcislsrb/oetumrlsit/obeimoltu/mhnemtati-honec(antorahnemltaos(m-onlaclotomr/lemlaosmrelomatolrhr-/-almcacatrrinrareoetortsishaolotafmlilo/no/1mfo/ol1leaft)/mtrh1h1iar)osa/an1nliptaso)iorolpilesrmsromaepftosnoir1eoletlaena/s1ordrete)frnradai1tstet/aid1oapos)rafoaoeiusfsfneau1p1cn/fr/t1t1uieceo)s)ntdnieiciosnsatonitspofeorarndtefesfosamtuesfnpmtatcteptfrmdiduaeoptrnanauaecsrtortueaiafort(fetfunsueure(nmonesecfecp(tFetstieieoieorFgmenanuitgpFouroueifrfgre2teatue()trm2s.ume)rp.e2e eclteicvteivecocnovnevrseifrofsneiocntintoionftopm-/pemt-h/-mxayn-xloeylnleon.neT.htTheehepsreopldreoucdctutivcedtisdctirosinbtrvuibetiurostnion(at(ianto p-/m-xylene. The product distribution (at xnyelepnreosdu(oc-i,nmg t-xoayngledinvpe-sxt(oyollu-e,enmnee-) a[3n30d6,]3p;7-(x–3y3)(l94em])n;epat()ohn4[lyd)y3lpa0alo,tk3iloy7lna–a(l34tkoe9)yfd]plt;aoboatlelenuyndeazbnlekenyn(e(pl4z4sar)e)toanepndeoduslblycypaeiaonldkzgkyeypaxnloayakeltltsyeladadnalnetkbedsyednpl(napozozteh-ley,nednameneplsosk-hlayasenlnfadrdotoeplpsmdo-flplxrytyohyameleknkmnyotyhelelasea)tthtfme[ery3doel0amptp,ht3hiytoe7ehln–naeo3otomil9fos]enxf;tyrohaolfyenmlxndayethsihloeanmeodsefxtatxhynyldeleaxnantyoieo optnirondfuotocfiltnuogelunxeynplernopedrosudc(ouin-c,ginmxg-yxlaeynnldenspe-(xsoy-(,loem-n,-em)a(-n[43ad)n0pd,o3-xpl7y-–axl3elyk9nly]e;ln)ae[tn3)ed(0d[43,b3)0e7p,n3–oz73ley–9na3]e;l9ksa]y;naladnandtedpdobleynalzkeynleasteadndphpeonlyoalslkfryolamtetdhephmeentohlyslfartoiomn tohfexmyleetnheyslatniodnxoyflexn

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