环氧乙烷和二氧化碳合成碳酸乙烯酯催化剂研究进展

doi:10.16085/j.issn.1000-6613.2017.2017-1633

摘要/Abstract

摘要： 二氧化碳（CO₂）通过环加成工艺合成环状碳酸酯的反应不仅符合“绿色化学”和“原子经济性”的理念，还能减少工业尾气中CO₂的排放所引起的温室效应影响，是一种利用工业催化技术实现碳捕集、利用和封存（CCS）的新技术，其经济效益和减排效率是传统CCS技术无法比拟的。本文综述了CO₂和环氧乙烷（EO）酯化反应催化剂的研究现状，总结了酯化催化剂的种类，分析了影响酯化催化剂性能的因素，如制备、助剂和载体等，最后对该催化剂的发展前景进行了展望。

关键词: 工业催化, 环氧乙烷, 二氧化碳, 催化剂

Abstract: The production of cyclic carbonate from CO₂ through a cycloaddition reaction represents a green and atom economic process which captures,utilize and stores CO₂ using an industrial catalytic technology.Its economic benefits and emission reduction are unmatched by traditional carbon capture and storage technologies.This work aimed to review the current development of catalyst for the esterification reaction of CO₂ and ethylene oxide(EO),categorize types of catalyst,analyzed the effect of factors such as preparation,auxiliary reagents,carriers etc on the activity of esterification catalysts as well as a discussion over the outlook of such catalysts.

Key words: industrial catalysis, ethylene oxide, carbon dioxide, catalyst

中图分类号:

TQ032

谭亚南, 何霖, 王凯, 程牧曦, 王科, 傅送保. 环氧乙烷和二氧化碳合成碳酸乙烯酯催化剂研究进展[J]. 化工进展, 2017, 36(S1): 241-246.

TAN Yanan, HE Lin, WANG Kai, CHENG Muxi, WANG Ke, FU Songbao. Research progress of catalyst for ethylene carbonate synthesis from ethylene oxide and carbon dioxide[J]. Chemical Industry and Engineering Progress, 2017, 36(S1): 241-246.

参考文献

[1] SU W Y,SPERANZA G P.Process for preparing alkylene carbonate,US 5003084[P].1991-03-26.
[2] YOSHIHISA K I,YUUICHI M K,MASSO I O.Preparation of cyclic carbonates:US 4880942[P].1989-11-14.
[3] 胡斌,卓仁禧,范昌烈.一种合成环状碳酸酯的新方法[J].化学试剂,1998,20(6):355-356.
[4] 赵艳敏,刘绍英,王公应.碳酸丙烯酯/碳酸乙烯酯的制备技术研究进展[J].现代化工,2005,25(s1):19-22.
[5] TIAN J S,MIAO C X,WANG J Q,et al.Efficient synthesis of dimethyl carbonate from methanol,propylene oxide and CO₂ catalyzed by recyclable inorganic base/phosphonium halide functionalized polyethylene glycol[J].Green Chem.,2007(9):566-571.
[6] Scientific Design Company.Preparation of alkylene carbonates:US5138073[P].1992-08-11.
[7] HE L N,YASUDA H,SAKAKURA T.New procedure for recycling homogeneous catalyst:propylene carbonate synthesis under supercritical CO₂ conditions[J].Green Chem.,2003,5(1):92-94.
[8] CALO V,NACCI A,MONOPOLI A,et al.Cyclic carbonate formation from carbon dioxide and oxiranes in tetrabutyl ammonium halides as solvents and catalysts[J].Org.Let.,2002,4(15):2561-2563.
[9] ZALOMAEVA O V,MAKSIMCHUK N V,CHIBIRYAEV A M,et al.Synthesis of cyclic carbonates from epoxides or olefins and CO₂ catalyzed by metal-organic frameworks and quaternary ammonium salts[J].Journal of Energy Chemistry,2013,22(1):130-135.
[10] 唐占忠,陈彦,瞿志坚,等.碳酸乙烯酯的合成研究[J].石油化工,1996,25(6):409-413.
[11] GOMES C R,FERREIRA D M,VOMSTANTION C J L,et al.Selectivity of the cyclic carbonate formation by fixation of carbon dioxide into epoxides catalyzed by Lewis bases[J].Tetrahedron Lett.,2008,49(48):6879-6881.
[12] ION A,PARVULESCU V,JACOBS P,et al.Sc and Zn catalyzed synthesis of cyclic carbonates from CO₂ and epoxides[J].Appl.Catal.A,2009,263:40-44.
[13] Shell Oil Company.Process for the preparation of alkylene carbonate:US7488835[P].2009-02-10.
[14] KIM H S,BAE J Y,LEE J S,et al.Phosphine-bound zinc halide complexes for the coupling reaction of ethylene oxide and carbon dioxide[J].Journal of Catalysis,2005,232(1):80-84.
[15] SUN J,WANG L,ZHANG S J,et al.ZnCl₂/phosphonium halide:an efficient Lewis acid/base catalyst for the synthesis of cyclic carbonate[J].Journal of Molecular Catalysis A Chemical,2006,256(1):295-300.
[16] KAWABE K,NAGATA K.Process for producing an alkylene glycol:US6187972[P].2001-02-03.
[17] VINCENZO C,ANGELO N,ANTONIO M,et al.Cyclic carbonate formation from carbon dioxide and oxiranes in tetrabutyl-ammonium halides as solvents and catalysts[J].Org.Lett.,2002,4(15):2561-2563.
[18] 李扬,朱培玉,王延儒.溴化四乙铵催化合成碳酸乙烯酯反应研究[J].南京师范大学学报,2007,7(1):59-62.
[19] SUN J,ZHANG S J,CHENG W G,et al.Hydroxyl-based ionic liquid:a novel efficient catalyst for chemical fixation of CO₂ to cyclic carbonate[J].Tetrahedron Lett.,2008,49:3588-3591.
[20] YANG Z Z,HE L N,MIAO C X,et al.Lewis basic ionic liquids-catalyzed conversion of carbon dioxide to cyclic carbonates[J].Adv.Synth.Catal.,2010,352:2233-2240.
[21] 石大川,鲁荆林,张成业,等.二氧化碳和环氧乙或丙烷合成碳酸乙或丙烯酯的方法:200910079169.X[P].,2009-03-04.
[22] 范文英.离子液体催化合成碳酸乙烯酯过鉴定[N].中国化工报,2008-01-02.
[23] 靳丽丽.金属卟啉/多手性席夫碱钴配合物的合成及其催化二氧化碳与环氧化合物的偶联反应研究[D].兰州大学,2008.
[24] 石明理,杜新耀,鲁绍芬.络合催化合成碳酸乙烯酯工艺:85100162[P].1985-04-01.
[25] 孟庆祥.有机锌、钴催化体系催化二氧化碳/环氧化合物共聚合研究[D].上海:华东理工大学,2016.
[26] TAKAHASHI T,WATAHIKI T,KITAZUME S,et al.Syner-gistic hy-brid catalyst for cyclic carbonate synthesis:remarkable acceleration caused by immobilization of homogeneous catalyst on silica[J].Chem.Commun.,2006,42(15):1664-1666.
[27] 陶毅,曾国蓉.聚苯乙烯负载季磷盐型树脂的制备及催化效应[J].应用化学,1990,7(3):69-71.
[28] 陈梁锋,肖含,何文军,等.高效负载型季磷盐催化合成碳酸乙烯酯[J].石油化工,2013,42(6):671-675.
[29] ZHAO Y,TIAN JS,QI X H,HAN Z N,et al.Quaternary ammonium salt-functionalized chitosan:An easily recyclable catalyst for efficient synthesis of cyclic carbonates from epoxides and carbon dioxide[J].Journal of Molecular Catalysis A,2007,271:284-289.
[30] DOU X Y,WANG J Q,DU Y,et al.Guanidinium salt functionalized PEG:an effective and recyclable homogen-eous catalyst for the synthesis of cyclic carbonates from CO₂ and epoxides under solvent-free conditions[J].Synlett.,2007,19:3058-3062.
[31] LU X B,FENG X J,HE R.Catalytic formation of ethylene carbonate from supercritical carbon dioxide/ethylene oxide mixture with tetradentate Schiff-base complexes as catalyst[J].Applied Catalysis A:Genral,2002,234:25-33.
[32] ZHANG Y Y,CHEN L,YIN S F,et al.Low-cost polymer-supported quaternary ammonium salts as high-efficiency catalysts for cycloaddition of CO₂ to epoxides[J].Cata.Lett.,2012,142:1376-1381.
[33] 张媛媛.固载型离子液体催化CO₂与环氧化物合成环状碳酸酯的研究[D].长沙:湖南大学,2012.
[34] 吴青海,任天瑞.固载化离子液体催化环氧乙烷和二氧化碳合成碳酸乙烯酯[J].过程工程学报,2012,12(2):302-309.
[35] DAI W L,CHEN L,YIN S F,et al.High-efficiency synthesis of cyclic carbonates from epoxides and CO₂ over hydroxyl ionic liquid catalyst grafted onto cross-linked polymer[J].Catal.Lett.,2010,137(1/2):74-80.
[36] DAI W L,CHEN L,YIN S F,et al.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[J].Catal. Lett.,2010,135(3/4):295-304.
[37] DOSKOCIL E J,BORDAWEKAR S V,KAYE B,et al.UV-vis spectros-copyofIodine adsorbed on alkali-metal-modified zeolite catalysts for addition of carbon dioxide to ethylene oxide[J].Phys.Chem.B,1999,103(30):277-282.
[38] KIM H S,KIM J J,KWON H N,et al.Well-defined highly active heterogeneous catalyst system for the coupling reactions of carbon dioxide and epoxides[J].Journal of Catalysis,2002,205(1):226-229.
[39] YASADU H,HE L N,SAKAKURA T,et al.Efficient synthesis of cyclic carbonate from carbon dioxide catalyzed by polyoxometalate:the remarkable effects of metal substitution[J].Journal of Catalysis,2005,233(1):119-122.
[40] 王春刚.Dawson杂多酸盐催化合成碳酸丙烯酯和碳酸乙烯酯[D].吉林:东北师范大学,2004.
[41] DAVIS R J,DOSKOCIL E J,BORDAWEKAR S.Structure/function relationships for basic zeolite catalysts containing occluded alkaliSpecies[J].Catal.Today,2000,62(2/3):241-247.