碳酸二甲酯甲基化反应催化剂和反应机理研究进展-朱茂电

3472012347櫅櫅櫅櫅櫅櫅櫅櫅櫅櫅櫅櫅櫅櫅殯殯殯殯615～619134122*121．6100412．2131643．2131644．100049DMC、。DMC、。DMC。O643．3O621．3A0258-3283201207-0615-052011-11-151972-。[e-mail]。DMC1992。DMCCH3—、CH3O—、CH3O—CO—、—CO—、、、1。1983Enichem-RavennaDMCDMC23。DMCDMCC-、N-、O-4。DMC。1DMCDMC5-9。DMCBAC2、BAL2NucleophilicsubstitutiononDMCbyBAC2andBAL2mechanismsDMCBAC2T＜90℃DMCBAL2T＞120℃7-10。Tundo811PearsonHSAB-DMC1-DMC2。。22.12.1.1DMCK2CO3、Cs2CO3。Bomben12K2CO3DMC。180℃DMC＞99%。51620127Lee13Cs2CO3120℃1-DMC4h100%O--1-。DMCO-13。O-CatalyticcycleforO-methylationofArOH2.1.2、14。DMC。Selva15-18YNaY、KYDMC。/-N-90%～97%15。-N-15。XC6H4NH2+ROCO2MeNaY→130～160℃XC6H4NHMe+ROH+CO2R=MeMeOCH22OCH22X=Hp-NCp-O2Np-Clo-MeO2C26-di-Me-N-Mono-N-methylationoffunctionalizedanilinesDMCSelvaDMCPictorialviewofthereactionofbenzylalcoholandDMCoverfaujasite18DMCNaY、NaX。O-＞＞。NaYDMCBonino19NaYDMCDMCNaYO—CH3C—OCH3O—CH3DMCNaYDMCDMCNa+NaYDMC。Juarez20Zn2+、Pb2+、Sc3+LewisZn2+SnⅣ、TiⅣ、ZrⅣMCM-4124-DMCN-。NaYLewis。Kirumakki2122Hβ、HY、HZSM5SA、2-DMCDMCZHPlausiblemechanismfortheesterificationofsalicylicacidwithdimethylcarbonateoverzeolitesZH6163472-DMCPossiblereactionmechanismforthealkylationof2-naphtholwithDMCoverzeolites。2-O-C-O-。Su23SADMCMS。。SA99%MS77%。Lewis。DMCPlausiblemechanismfortheesterificationofsalicylicacidwithDMCoveramesoporousaluminosilicate2.2、。DMC。Chang24DMC-C-DMC、DMC。ⅣB。ⅣBⅥ。Sreekumar2526Zn1－xCoxFe2O4x=00.20.50.81.0DMCN-。200～250℃。xFe3+Co2+0≤x≤0.5xx＞0.5。Jyothi2728Mg-AlDMCO-。573K84%。Wu29-DMCO-。F/Mg2.93AlO、DMC/2473K8h99.3%100%。2.3MOFs、。MOFs、、30。Dhakshinamoor-thy31、、MOFsAl2-BDC3135Al2BDC3。170℃50mg、250mgDMC、100mgAl2BDC38h93%73%。716201273。DMC、、。100℃DMC。DMC、、、。DMCDMC。1ARICOFTUNDOP．DimethylcarbonateasamoderngreenreagentandsolventJ．Russ．Chem．Rev．2010796479-489．2MEMOLISSELVAMTUNDOP．Dimethylcarbonateforeco-friendlymethylationreactionsJ．Chemosphere2001431115-121．3SHIVARKARABGUPTESPCHAUDHARIRV．Se-lectivesynthesisofNN-dimetylanilinederivativesusingdimethylcarbonateasamethylatingagentandoniumsaltasacatalystJ．J．Mol．Catal．AChem．2005226149-56．4．J．2008120-23．5SELVAMPEROSAA．Greenchemistrymetricsacom-parativeevaluationofdimethylcarbonatemethyliodidedimethylsulfateandmethanolasmethylatingagentsJ．GreenChem．2008104457-464．6LAMOUREUXGAGEROC．AcomparisonofseveralmodernalkylatingagentsJ．ARKIVOC20091251-264．7TUNDOPSELVAM．Thechemistryofdimethylcarbon-ateJ．Acc．Chem．Res．2002359706-716．8TUNDOPROSSILLORISA．DimethylcarbonateasanambidentelectrophileJ．J．Org．Chem．20057062219-2224．9SELVAM．Greenapproachestohighlyselectiveproces-sesreactionsofdimethylcarbonateoverbothzeolitesandbasecatalystsJ．PureAppl．Chem．200779111855-1867．10TUNDOP．NewdevelopmentsindimethylcarbonatechemistryJ．PureAppl．Chem．20017371117-1124．11ROSAMILIAAEARICOFTUNDOP．Insightintothehard-softacid-basepropertiesofdifferentlysubstitu-tedphenylhydrazinesinreactionswithdimethylcarbon-ateJ．J．Phys．Chem．B20081124614525-14529．12BOMBENAMARQUESBASELVAMetal．Anewsynthesisof2-aryloxypropionicacidsderivativesviase-lectivemono-C-methylationofmethylaryloxyacetatesandaryloxyacetonitrileswithdimethylcarbonateJ．Tetrahedron1995514211573-11580．13LEEYSHIMIZUI．ConvenientO-methylationofphe-nolswithdimethylcarbonateJ．Synlett199810101063-1064．14CUNDYCSCOXPA．ThehydrothermalsynthesisofzeoliteshistoryanddevelopmentfromtheearliestdaystothepresenttimeJ．Chem．Rev．20031033663-701．15SELVAMTUNDOPPEROSAA．Reactionoffunction-alizedanilineswithdimethylcarbonateoverNaYFauja-site．3．chemoselectivitytowardmono-N-methylationJ．J．Org．Chem．200368197374-7378．16SELVAMTUNDOP．SelectiveNN-dimethylationofprimaryaromaticamineswithmethylalkylcarbonatesinthepresenceofphosphoniumsaltsJ．J．Org．Chem．20067141464-1470．17SELVAMTUNDOPBRUNELLIDetal．Chemoselec-tivereactionsofdimethylcarbonatecatalysedbyalkalimetalexchangedfaujasitesthecaseofindolylcarboxylicacidsandindolylsubstitutedalkylcarboxylicacidsJ．GreenChem．200795463-468．18SELVAMMILITELLOEFABRISM．Themethylationofbenzyl-typealcoholswithdimethylcarbonateinthepresenceofY-andX-faujasitesselectivesynthesisofmethylethersJ．GreenChem．200810173-79．19BONINOFDAMINABORDIGASetal．DimethylcarbonateinthesupercagesofNaYzeolitestheroleoflocalfieldsinpromotingmethylationandcarboxymethyl-ationactivityJ．Angew．Chem．Int．Ed200544304774-4777．20JUAREZRPADILLAACORMAAetal．TransitionmetalcontainingzeolitesandmesoporousMCM-41asheterogeneouscatalystsfortheN-alkylationof24-dia-minotoluenewithdimethylcarbonateJ．Catal．Com-mun．2009105472-476．81634721KIRUMAKKISRNAGARAJUNMURTHYKVVSBSRetal．EsterificationofsalicylicacidoverzeolitesusingdimethylcarbonateJ．Appl．Catal．AGen．20022261175-182．22KIRUMAKKISRNAGARAJUNCHARYKVRetal．AfacileO-alkylationof2-naphtholoverzeolitesHβHYandHZSM5usingdimethylcarbonateandmethanolJ．J．Catal．2004221549-559．23SUXiao-weiLIJun-pinXIAOFu-kuietal．Esterifica-tionofsalicylicacidwithdimethylcarbonateovermeso-porousaluminosilicateJ．Ind．Eng．Chem．Res．20094873685-3691．24CHANGCDHUANGTJ．SelectivemonomethylationofaromaticswithdimethylcarbonateUS5804690P．1998-09-08．25SREEKUMARKJYOTHITMMATHEWTetal．Se-lectiveN-methylationofanilinewithdimethylcarbonateoverZn1－xCoxFe2O4x=00．20．50．8and1．0typesyste