3-(2-Hydroxyl-Ethyl)-1-Propylimidazolium Bromide Immobilized on SBA-15 as Efficient Catalyst for the Synthesis of Cyclic Carbonates via the Coupling of Carbon Dioxide with Epoxides

3-(2-hydroxyl-ethyl)-1-propylimidazolium bromide (HEPIMBr) was immobilized onto SBA-15, Al-SBA-15 mesoporous molecular sieves and SiO₂ by chemical grafting method. The materials were characterized and used as catalysts for solvent-free synthesis of cyclic carbonates from CO₂ and epoxides under relat...

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Published inCatalysis letters Vol. 135; no. 3-4; pp. 295 - 304
Main Authors Dai, Wei-Li, Chen, Lang, Yin, Shuang-Feng, Luo, Sheng-Lian, Au, Chak-Tong
Format Journal Article
LanguageEnglish
Published Boston Boston : Springer US 01.04.2010
Springer US
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Springer Nature B.V
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Abstract 3-(2-hydroxyl-ethyl)-1-propylimidazolium bromide (HEPIMBr) was immobilized onto SBA-15, Al-SBA-15 mesoporous molecular sieves and SiO₂ by chemical grafting method. The materials were characterized and used as catalysts for solvent-free synthesis of cyclic carbonates from CO₂ and epoxides under relatively mild conditions. Among them, the HEPIMBr immobilized on SBA-15 performs the best, showing carbonate selectivity and yield of ca. 100% (120 °C, 2.0 MPa, 2 h). The catalyst is thermally stable and shows good reusability. Based on the experimental results, a plausible reaction mechanism has been proposed for the catalytic reaction. Graphical Abstract 3-(2-hydroxyl-ethyl)-1-propylimidazolium bromide (HEPIMBr) was immobilized on SBA-15 mesoporous molecular sieve by chemical grafting method. It was found the material shows high catalytic efficiency and good stability towards the cyclic carbonates synthesis via. Cycloaddition of CO₂ to epoxides. Moreover, the catalyst can be easily separated from the product. A plausible reaction mechanism has been proposed for the catalytic action. [graphic removed]
AbstractList 3-(2-hydroxyl-ethyl)-1-propylimidazolium bromide (HEPIMBr) was immobilized onto SBA-15, Al-SBA-15 mesoporous molecular sieves and SiO(2) by chemical grafting method. The materials were characterized and used as catalysts for solvent-free synthesis of cyclic carbonates from CO(2) and epoxides under relatively mild conditions. Among them, the HEPIMBr immobilized on SBA-15 performs the best, showing carbonate selectivity and yield of ca. 100% (120 °C, 2.0 MPa, 2 h). The catalyst is thermally stable and shows good reusability. Based on the experimental results, a plausible reaction mechanism has been proposed for the catalytic reaction. Graphical Abstract 3-(2-hydroxyl-ethyl)-1-propylimidazolium bromide (HEPIMBr) was immobilized on SBA-15 mesoporous molecular sieve by chemical grafting method. It was found the material shows high catalytic efficiency and good stability towards the cyclic carbonates synthesis via. Cycloaddition of CO(2) to epoxides. Moreover, the catalyst can be easily separated from the product. A plausible reaction mechanism has been proposed for the catalytic action. [graphic removed]
3-(2-hydroxyl-ethyl)-1-propylimidazolium bromide (HEPIMBr) was immobilized onto SBA-15, Al-SBA-15 mesoporous molecular sieves and Si[O.sub.2] by chemical grafting method. The materials were characterized and used as catalysts for solvent-free synthesis of cyclic carbonates from C[O.sub.2] and epoxides under relatively mild conditions. Among them, the HEPIMBr immobilized on SBA-15 performs the best, showing carbonate selectivity and yield of ca. 100% (120°C, 2.0 MPa, 2 h). The catalyst is thermally stable and shows good reusability. Based on the experimental results, a plausible reaction mechanism has been proposed for the catalytic reaction.
3-(2-hydroxyl-ethyl)-1-propylimidazolium bromide (HEPIMBr) was immobilized onto SBA-15, Al-SBA-15 mesoporous molecular sieves and SiO2 by chemical grafting method. The materials were characterized and used as catalysts for solvent-free synthesis of cyclic carbonates from CO2 and epoxides under relatively mild conditions. Among them, the HEPIMBr immobilized on SBA-15 performs the best, showing carbonate selectivity and yield of ca. 100% (120 °C, 2.0 MPa, 2 h). The catalyst is thermally stable and shows good reusability. Based on the experimental results, a plausible reaction mechanism has been proposed for the catalytic reaction.Graphical Abstract3-(2-hydroxyl-ethyl)-1-propylimidazolium bromide (HEPIMBr) was immobilized on SBA-15 mesoporous molecular sieve by chemical grafting method. It was found the material shows high catalytic efficiency and good stability towards the cyclic carbonates synthesis via. Cycloaddition of CO2 to epoxides. Moreover, the catalyst can be easily separated from the product. A plausible reaction mechanism has been proposed for the catalytic action.
3-(2-hydroxyl-ethyl)-1-propylimidazolium bromide (HEPIMBr) was immobilized onto SBA-15, Al-SBA-15 mesoporous molecular sieves and Si[O.sub.2] by chemical grafting method. The materials were characterized and used as catalysts for solvent-free synthesis of cyclic carbonates from C[O.sub.2] and epoxides under relatively mild conditions. Among them, the HEPIMBr immobilized on SBA-15 performs the best, showing carbonate selectivity and yield of ca. 100% (120°C, 2.0 MPa, 2 h). The catalyst is thermally stable and shows good reusability. Based on the experimental results, a plausible reaction mechanism has been proposed for the catalytic reaction. Keywords SBA-15 * Hydroxyl ionic liquids * Carbon dioxide * Epoxide * Cyclic carbonate
3-(2-hydroxyl-ethyl)-1-propylimidazolium bromide (HEPIMBr) was immobilized onto SBA-15, Al-SBA-15 mesoporous molecular sieves and SiO 2 by chemical grafting method. The materials were characterized and used as catalysts for solvent-free synthesis of cyclic carbonates from CO 2 and epoxides under relatively mild conditions. Among them, the HEPIMBr immobilized on SBA-15 performs the best, showing carbonate selectivity and yield of ca. 100% (120 °C, 2.0 MPa, 2 h). The catalyst is thermally stable and shows good reusability. Based on the experimental results, a plausible reaction mechanism has been proposed for the catalytic reaction. Graphical Abstract 3-(2-hydroxyl-ethyl)-1-propylimidazolium bromide (HEPIMBr) was immobilized on SBA-15 mesoporous molecular sieve by chemical grafting method. It was found the material shows high catalytic efficiency and good stability towards the cyclic carbonates synthesis via. Cycloaddition of CO 2 to epoxides. Moreover, the catalyst can be easily separated from the product. A plausible reaction mechanism has been proposed for the catalytic action.
3-(2-hydroxyl-ethyl)-1-propylimidazolium bromide (HEPIMBr) was immobilized onto SBA-15, Al-SBA-15 mesoporous molecular sieves and SiO₂ by chemical grafting method. The materials were characterized and used as catalysts for solvent-free synthesis of cyclic carbonates from CO₂ and epoxides under relatively mild conditions. Among them, the HEPIMBr immobilized on SBA-15 performs the best, showing carbonate selectivity and yield of ca. 100% (120 °C, 2.0 MPa, 2 h). The catalyst is thermally stable and shows good reusability. Based on the experimental results, a plausible reaction mechanism has been proposed for the catalytic reaction. Graphical Abstract 3-(2-hydroxyl-ethyl)-1-propylimidazolium bromide (HEPIMBr) was immobilized on SBA-15 mesoporous molecular sieve by chemical grafting method. It was found the material shows high catalytic efficiency and good stability towards the cyclic carbonates synthesis via. Cycloaddition of CO₂ to epoxides. Moreover, the catalyst can be easily separated from the product. A plausible reaction mechanism has been proposed for the catalytic action. [graphic removed]
Audience Academic
Author Au, Chak-Tong
Luo, Sheng-Lian
Yin, Shuang-Feng
Dai, Wei-Li
Chen, Lang
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  fullname: Au, Chak-Tong
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Issue 3-4
Keywords Hydroxyl ionic liquids
Cyclic carbonate
SBA-15
Carbon dioxide
Epoxide
Binary compound
Catalytic reaction
Selectivity
Porous material
Grafting
Silica
Mesoporosity
Molecular sieve
Ionic liquid
Heterogeneous catalysis
Synthesis
Silicon oxides
Solvent free reaction
Bromides
Reaction mechanism
Carbonates
Catalyst
Hydroxyl
Language English
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CC BY 4.0
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PublicationDate 2010-04-01
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  day: 01
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PublicationTitle Catalysis letters
PublicationTitleAbbrev Catal Lett
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References YasudaHHeLNTakahashiTSakakuraTAppl Catal A: Gen200629817710.1016/j.apcata.2005.09.0341:CAS:528:DC%2BD2MXht12lsL3L
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UdayakumarSSonYSLeeMKParkSWParkDWAppl Catal A: Gen200834719210.1016/j.apcata.2008.06.0091:CAS:528:DC%2BD1cXps1eqsLY%3D
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SakaiTTsutsumiYEmaTGreen Chem20081033710.1039/b718321f1:CAS:528:DC%2BD1cXislSmsLY%3D
RatzenhoferMKischHAngew Chem Int Ed Engl19801931710.1002/anie.198003171
BhanageBMFujitaSIkushimaYAraiMGreen Chem200357110.1039/b207750g1:CAS:528:DC%2BD3sXhtFSgtrw%3D
SunJMFujitaSIZhaoFYAraiMAppl Catal A: Gen200528722110.1016/j.apcata.2005.03.0351:CAS:528:DC%2BD2MXltVOiu7o%3D
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LuXBHeRBaiCXJ Mol Catal A: Chem2002186110.1016/S1381-1169(01)00442-31:CAS:528:DC%2BD38XkvFKntrw%3D
RaminMGrunwaldtJDBaikerAJ Catal200523425610.1016/j.jcat.2005.06.0201:CAS:528:DC%2BD2MXpt1ehsLk%3D
JingSHChangTJinLWuMQiuWCatal Commun20078163010.1016/j.catcom.2006.12.0271:CAS:528:DC%2BD2sXhtVOlsr7E
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UdayakumarSParkSWParkDWChoiBSCatal Commun20089156310.1016/j.catcom.2008.01.0011:CAS:528:DC%2BD1cXjsVShs78%3D
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YasudaHHeLNSakakuraTHuCJ Catal200523311910.1016/j.jcat.2005.04.0301:CAS:528:DC%2BD2MXltlersb4%3D
WangJQKongDLChenJYCaiFHeLNJ Mol Catal A: Chem200624914310.1016/j.molcata.2006.01.0081:CAS:528:DC%2BD28XjslCksLg%3D
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References_xml – reference: LuXBHeRBaiCXJ Mol Catal A: Chem2002186110.1016/S1381-1169(01)00442-31:CAS:528:DC%2BD38XkvFKntrw%3D
– reference: ZhangXLWangDFZhaoNAl-ArifiASNAouakTAl-OthmanZAWeiWSunYHCatal Commun2009114310.1016/j.catcom.2009.08.0071:CAS:528:DC%2BD1MXht1amtLbF
– reference: DeCYLuBLvHYuYYBaiYCaiQHCatal Lett200912845910.1007/s10562-008-9773-11:CAS:528:DC%2BD1cXhsVCgtLrP
– reference: YamaguchiKEbitaniKYoshidaTYoshidaHKanedaKJ Am Chem Soc1999121452610.1021/ja99021651:CAS:528:DyaK1MXisFGlt74%3D
– reference: BhanageBMFujitaSIkushimaYAraiMGreen Chem200357110.1039/b207750g1:CAS:528:DC%2BD3sXhtFSgtrw%3D
– reference: SibaouihARyanPLeskelaMRiegerBRepoTAppl Catal A: Gen200936519410.1016/j.apcata.2009.06.0111:CAS:528:DC%2BD1MXptlSlsL0%3D
– reference: DoskocilEJMicropor Mesopor Mater20047617710.1016/j.micromeso.2004.08.0091:CAS:528:DC%2BD2cXpsFajtbo%3D
– reference: WangJQKongDLChenJYCaiFHeLNJ Mol Catal A: Chem200624914310.1016/j.molcata.2006.01.0081:CAS:528:DC%2BD28XjslCksLg%3D
– reference: XiaoLFLiFWPengJJXiaCGJ Mol Catal A: Chem200625326510.1016/j.molcata.2006.03.0471:CAS:528:DC%2BD28Xlt12kt74%3D
– reference: KimHSBaeJYLeeJSKwonOJelliarkoPLeeSDLeeSHJ Catal20052328010.1016/j.jcat.2005.01.0331:CAS:528:DC%2BD2MXjslOnsbo%3D
– reference: UdayakumarSRamanVShimHLParkDWAppl Catal A: Gen20093689710.1016/j.apcata.2009.08.0151:CAS:528:DC%2BD1MXhtFOqu7bP
– reference: JutzFGrunwaldtJDBaikerAJ Mol Catal A: Chem20082799410.1016/j.molcata.2007.10.0101:CAS:528:DC%2BD2sXhsVWjurnE
– reference: FujitaSBhanageBMIkushimaYShiraiMToriiKAraiMCatal Lett2002799510.1023/A:10153963182541:CAS:528:DC%2BD38Xksl2hsb8%3D
– reference: WangJQYueXDCaiFHeLNCatal Commun2007816710.1016/j.catcom.2006.05.0491:CAS:528:DC%2BD2sXivFentg%3D%3D
– reference: UdayakumarSLeeMKShimHLParkSWParkDWCatal Commun20091065910.1016/j.catcom.2008.11.0171:CAS:528:DC%2BD1MXpsVSisg%3D%3D
– reference: YasudaHHeLNSakakuraTHuCJ Catal200523311910.1016/j.jcat.2005.04.0301:CAS:528:DC%2BD2MXltlersb4%3D
– reference: TuMDavisRJJ Catal20011998510.1006/jcat.2000.31451:CAS:528:DC%2BD3MXit1aiurc%3D
– reference: NomuraRKimuraMTeshimaSNinagawaAMatsudaHBull Chem Soc Jpn198255320010.1246/bcsj.55.32001:CAS:528:DyaL3sXhs1WjtA%3D%3D
– reference: KimHSKimJJKwonHNChungMJLeeBGJangHGJ Catal200220522610.1006/jcat.2001.34441:CAS:528:DC%2BD3MXpt1aquro%3D
– reference: UdayakumarSLeeMKShimHLParkDWAppl Catal A: Gen20093658810.1016/j.apcata.2009.05.0571:CAS:528:DC%2BD1MXos12qt7Y%3D
– reference: LuXBXiuJHHeRJinKLuoLMFengXJAppl Catal A: Gen20042757310.1016/j.apcata.2004.07.0221:CAS:528:DC%2BD2cXnvFajtLs%3D
– reference: SankarMTarteNHManikandanPAppl Catal A: Gen200427621710.1016/j.apcata.2004.08.0081:CAS:528:DC%2BD2cXovVyqtbg%3D
– reference: ZhaoDYHuoQSFengJLChmelkaBFStuckyGDAmJChem Soc1998120602410.1021/ja974025i1:CAS:528:DyaK1cXjslKnsbY%3D
– reference: RaminMGrunwaldtJDBaikerAJ Catal200523425610.1016/j.jcat.2005.06.0201:CAS:528:DC%2BD2MXpt1ehsLk%3D
– reference: KawanamiHSasakiAMatsuiKIkushimaYChem Commun20033989610.1039/b212823c1:CAS:528:DC%2BD3sXitlyktb4%3D
– reference: OnoFQiaoKTomidaDYokoyamaCJ Mol Catal A: Chem200726322310.1016/j.molcata.2006.08.0371:CAS:528:DC%2BD2sXhtlWhtLg%3D
– reference: SunJZhangSJChengWGRenJYTetrahedron Lett200849358810.1016/j.tetlet.2008.04.0221:CAS:528:DC%2BD1cXlvVSrur8%3D
– reference: LiFWXiaoLFXiaCGHuBTetrahedron Lett200445830710.1016/j.tetlet.2004.09.0741:CAS:528:DC%2BD2cXotlSntbY%3D
– reference: YinSFDaiWLLiWSZhouXPShimadaSJ Mol Catal (China)200621264
– reference: JingSHChangTJinLWuMQiuWCatal Commun20078163010.1016/j.catcom.2006.12.0271:CAS:528:DC%2BD2sXhtVOlsr7E
– reference: SakoTFukaiTSahashiRInd Eng Chem Res200241535310.1021/ie020164j
– reference: SunJRenJYZhangSJChengWGTetrahedron Lett20095042310.1016/j.tetlet.2008.11.0341:CAS:528:DC%2BD1cXhsFWjurfM
– reference: JiangJLGaoFXHaoRMQiuXQJ Org Chem20057038110.1021/jo04857851:CAS:528:DC%2BD2cXhtVSmtLvI
– reference: SrivastavaRSrinivasDRatnasamyPMicroporous Mesoporous Mater20069031410.1016/j.micromeso.2005.10.0431:CAS:528:DC%2BD28XhvVSmtrc%3D
– reference: SunJMFujitaSIZhaoFYAraiMAppl Catal A: Gen200528722110.1016/j.apcata.2005.03.0351:CAS:528:DC%2BD2MXltVOiu7o%3D
– reference: SakaiTTsutsumiYEmaTGreen Chem20081033710.1039/b718321f1:CAS:528:DC%2BD1cXislSmsLY%3D
– reference: SunJWangLZhangSJLiZXZhangXPDaiWBMoriRJ Mol Catal A: Chem200625629510.1016/j.molcata.2006.05.0041:CAS:528:DC%2BD28XoslGmt7c%3D
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– reference: KimHSKimJJLeeSDLahMSMoonDJangHGChem Eur J2003967810.1002/chem.2003900761:CAS:528:DC%2BD3sXhtlSjs7w%3D
– reference: XieYZhangZFJiangTHeJLHanBXWuTBDingKLAngew Chem Int Ed200746725510.1002/anie.2007014671:CAS:528:DC%2BD2sXhtFCqsLfE
– reference: YasudaHHeLNTakahashiTSakakuraTAppl Catal A: Gen200629817710.1016/j.apcata.2005.09.0341:CAS:528:DC%2BD2MXht12lsL3L
– reference: DarensbourgDJHoltcampMWCoord Chem Rev199615315510.1016/0010-8545(95)01232-X1:CAS:528:DyaK28Xjs1WgsLk%3D
– reference: KimYJVarmaRSJ Org Chem200570788210.1021/jo050699x1:CAS:528:DC%2BD2MXpslWrsbk%3D
– reference: RaminMvan VegtenNGrunwaldtJBaikerAJ Mol Catal A: Chem200625816510.1016/j.molcata.2006.05.0411:CAS:528:DC%2BD28Xps1Wqtrs%3D
– reference: UdayakumarSParkSWParkDWChoiBSCatal Commun20089156310.1016/j.catcom.2008.01.0011:CAS:528:DC%2BD1cXjsVShs78%3D
– reference: UdayakumarSSonYSLeeMKParkSWParkDWAppl Catal A: Gen200834719210.1016/j.apcata.2008.06.0091:CAS:528:DC%2BD1cXps1eqsLY%3D
– reference: SunJMFujitaSZhaoFYAraiMGreen Chem2004661310.1039/b413229g1:CAS:528:DC%2BD2cXhtVSitLbF
– reference: MelendezJNorthMPasqualeREur J Inorg Chem20072007332310.1002/ejic.2007005211:CAS:528:DC%2BD2sXptV2itbs%3D
– reference: ValkenbergMHdeCastroCHölderichWFGreen Chem200248810.1039/b107946h1:CAS:528:DC%2BD2cXksVCgtro%3D
– reference: TakahashiTWatahikiTKitazumeSYasudaHSakakuraTChem Commun200642166410.1039/b517140g1:CAS:528:DC%2BD28XjtVCrsro%3D
– reference: HiyoshiNYogoKYashimaTMicroporous Mesoporous Mater20058435710.1016/j.micromeso.2005.06.0101:CAS:528:DC%2BD2MXpsF2nt70%3D
– reference: DaiWLLuoSLYinSFAuCTAppl Catal A: Gen2009366210.1016/j.apcata.2009.06.0451:CAS:528:DC%2BD1MXpvF2nt70%3Dand review references therein
– reference: RatzenhoferMKischHAngew Chem Int Ed Engl19801931710.1002/anie.198003171
– reference: ZhaoYTianJSQiXHHanZNZhuangYYHeLNJ Mol Catal A: Chem200727128410.1016/j.molcata.2007.03.0471:CAS:528:DC%2BD2sXlt1Kgu78%3D
– reference: SibaouihARyanPAxenovKVSundergMRLeskelaMRepoTJ Mol Catal A: Chem20093128710.1016/j.molcata.2009.07.0091:CAS:528:DC%2BD1MXhtFaktL7E
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Snippet 3-(2-hydroxyl-ethyl)-1-propylimidazolium bromide (HEPIMBr) was immobilized onto SBA-15, Al-SBA-15 mesoporous molecular sieves and SiO₂ by chemical grafting...
3-(2-hydroxyl-ethyl)-1-propylimidazolium bromide (HEPIMBr) was immobilized onto SBA-15, Al-SBA-15 mesoporous molecular sieves and SiO 2 by chemical grafting...
3-(2-hydroxyl-ethyl)-1-propylimidazolium bromide (HEPIMBr) was immobilized onto SBA-15, Al-SBA-15 mesoporous molecular sieves and Si[O.sub.2] by chemical...
3-(2-hydroxyl-ethyl)-1-propylimidazolium bromide (HEPIMBr) was immobilized onto SBA-15, Al-SBA-15 mesoporous molecular sieves and SiO2 by chemical grafting...
3-(2-hydroxyl-ethyl)-1-propylimidazolium bromide (HEPIMBr) was immobilized onto SBA-15, Al-SBA-15 mesoporous molecular sieves and SiO(2) by chemical grafting...
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StartPage 295
SubjectTerms Carbon dioxide
Carbonates
Catalysis
Catalysts
Chemical synthesis
Chemistry
Chemistry and Materials Science
Colloidal state and disperse state
Coupling (molecular)
Cycloaddition
Exact sciences and technology
General and physical chemistry
Grafting
Hydroxides
Industrial Chemistry/Chemical Engineering
Molecular sieves
Organic chemistry
Organometallic Chemistry
Physical Chemistry
Porous materials
Reaction mechanisms
Selectivity
Silicon dioxide
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Thermal stability
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Title 3-(2-Hydroxyl-Ethyl)-1-Propylimidazolium Bromide Immobilized on SBA-15 as Efficient Catalyst for the Synthesis of Cyclic Carbonates via the Coupling of Carbon Dioxide with Epoxides
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