Acid-base synergistic effect promoted cycloaddition reaction from CO2 with epoxide in homogenous catalysis systems

doi:10.11949/j.issn.0438-1157.20150749

Abstract

Abstract:

In terms of the so-called “sustainable society” and “green chemistry” concepts, carbon dioxide capture, storage and utilization have been attracted much attention from both industrial and academic viewpoints in recent years. The synthesis of five-membered cyclic carbonates via the 100% atom-economical cycloaddition of epoxides with CO₂ under mild condition is one of the most promising ways. Herein, based on the design idea of homogenous catalysts, the research advance of the acid-base synergistic effect promoted the cycloaddition reaction from CO₂ and epoxide is reviewed from the perspective of catalyst structure, including simple binary catalytic systems, functionalized one-component catalytic systems and metal complexes catalytic systems etc.

Key words: carbon dioxide, catalysis, complexes, cyclic carbonate, cycloaddition reaction, acid-base synergistic effect

摘要：

基于“可持续发展”和“绿色化学”的概念,近年来CO₂的捕获、储存及资源化利用在工业上和学术上一直备受关注。通过具有100%原子经济性特点的CO₂与环氧化物环加成反应合成五元环状碳酸酯是最有前景的方法之一。基于均相催化剂的设计思想与方法,以CO₂和环氧化物的活化本质出发,从催化剂结构的角度综述了均相体系中酸碱协同催化CO₂与环氧化物环加成反应合成环状碳酸酯的研究进展,包括简单二元催化体系、功能型一元催化体系和金属配合物催化体系等。

关键词: 二氧化碳, 催化作用, 配合物, 环状碳酸酯, 环加成反应, 酸碱协同催化

CLC Number:

TQ028.8

LUO Rongchang, ZHOU Xiantai, YANG Zhi, ZHANG Wuying, JI Hongbing. Acid-base synergistic effect promoted cycloaddition reaction from CO₂ with epoxide in homogenous catalysis systems[J]. CIESC Journal, 2016, 67(1): 258-276.

罗荣昌, 周贤太, 杨智, 张武英, 纪红兵. 均相体系中酸碱协同催化二氧化碳与环氧化物的环加成反应[J]. 化工学报, 2016, 67(1): 258-276.

References 149

[1]	OMAE I. Recent developments in carbon dioxide utilization for the production of organic chemicals [J]. Coordin. Chem. Rev., 2012, 256 (13/14): 1384-1405. DOI: 10.1016/j.ccr.2012.03.017.
[2]	MAEDA C, MIYAZAKI Y, EMA T. Recent progress in catalytic conversions of carbon dioxide [J]. Catal. Sci. Technol., 2014, 4 (6): 1482-1497. DOI: 10.1039/C3CY00993A.
[3]	LIU Q, WU L, JACKSTELL R, et al. Using carbon dioxide as a building block in organic synthesis [J]. Nat. Commun., 2015, 6: 1-15. DOI: 10.1038/ncomms6933.
[4]	OMAE I. Aspects of carbon dioxide utilization [J]. Catal. Today, 2006, 115 (1/2/3/4): 33-52. DOI: 10.1016/j.cattod.2006.02.024.
[5]	ARESTA M, DIBENEDETTO A. Utilisation of CO2 as a chemical feedstock: opportunities and challenges [J]. Dalton Trans., 2007, 28 (28): 2975-2992. DOI: 10.1039/B700658F.
[6]	SAKAKURA T, CHOI J C, YASUDA H. Transformation of carbon dioxide [J]. Chem. Rev., 2007, 107 (6): 2365-2387. DOI: 10.1021/cr068357u.
[7]	YU K M K, CURCIC I, GABRIEL J, et al. Recent advances in CO2 capture and utilization [J]. ChemSusChem, 2008, 1 (11): 893-899. DOI: 10.1002/cssc.200800169.
[8]	RIDUAN S N, ZHANG Y. Recent developments in carbon dioxide utilization under mild conditions [J]. Dalton Trans., 2010, 39 (14): 3347-3357. DOI: 10.1039/B920163G.
[9]	SCHÄFFNER B, SCHÄFFNER F, VEREVKIN S P, et al. Organic carbonates as solvents in synthesis and catalysis [J]. Chem. Rev., 2010, 110 (8): 4554-4581. DOI: 10.1021/cr900393d.
[10]	CLEMENTS J H. Reactive applications of cyclic alkylene carbonates [J]. Ind. Eng. Chem. Res., 2003, 42 (4): 663-674.
[11]	NORTH M, PASQUALE R, YOUNG C. Synthesis of cyclic carbonates from epoxides and CO2 [J]. Green Chem., 2010, 12 (9): 1514-1539. DOI: 10.1039/c0gc00065e.
[12]	HE Q, O'BRIEN J W, KITSELMAN K A, et al. Synthesis of cyclic carbonates from CO2 and epoxides using ionic liquids and related catalysts including choline chloride-metal halide mixtures [J]. Catal. Sci. Technol., 2014, 4 (6): 1513-1528. DOI: 10.1039/C3CY00998J.
[13]	COMERFORD J W, INGRAM L D V, NORTH M, et al. Sustainable metal-based catalysts for the synthesis of cyclic carbonates containing five-membered rings [J]. Green Chem., 2015, 17 (4): 1966-1987. DOI: 10.1039/C4GC01719F.
[14]	SUN J, FUJITA S I, ARAI M. Development in the green synthesis of cyclic carbonate from carbon dioxide using ionic liquids [J]. J. Organomet. Chem., 2005, 690 (44): 3490-3497. DOI: 10.1016/j.jorganchem.2005.02.011.
[15]	ZHANG S, CHEN Y, LI F, et al. Fixation and conversion of CO2 using ionic liquids [J]. Catal. Today, 2006, 115 (1/2/3/4): 61-69. DOI: 10.1016/j.cattod.2006.02.021.
[16]	ZHANG J, SUN J, ZHANG X, et al. The recent development of CO2 fixation and conversion by ionic liquid [J]. Greenh. Gases, 2011, 1 (2): 142-159. DOI: 10.1002/ghg.13.
[17]	XU B, WANG J, SUN J, et al. Fixation of CO2 into cyclic carbonates catalyzed by ionic liquids: a multi-scale approach [J]. Green Chem., 2015, 17 (1): 108-122. DOI: 10.1039/C4GC01754D.
[18]	YIN X, MOSS J R. Recent developments in the activation of carbon dioxide by metal complexes [J]. Coordin. Chem. Rev., 1999, 181 (1): 27-59. DOI: 10.1016/S0010-8545 (98)00171-4.
[19]	DECORTES A, CASTILLA A M, KLEIJ A W. Salen-complex-mediated formation of cyclic carbonates by cycloaddition of CO2 to epoxides [J]. Angew. Chem. Int. Ed., 2010, 49 (51): 9822-9837. DOI: 10.1002/anie.201002087.
[20]	FIORANI G, GUO W, KLEIJ A W. Sustainable conversion of carbon dioxide: the advent of organocatalysis [J]. Green Chem., 2015, 17 (3): 1375-1389. DOI: 10.1039/C4GC01959H.
[21]	ZHU M Q, CARREON M A. Porous crystals as active catalysts for the synthesis of cyclic carbonates [J]. J. Appl. Polym. Sci., 2014, 131 (5): 13. DOI: 10.1002/app.39738.
[22]	BEYZAVI M H, STEPHENSON C J, LIU Y, et al. Metal-organic framework-based catalysts: chemical fixation of CO2 with epoxides leading to cyclic organic carbonates [J]. Frontiers in Energy Research, 2015, 2: 1-10. DOI: 10.3389/fenrg.2014.00063.
[23]	DAI W, LUO S, YIN S, et al. The direct transformation of carbon dioxide to organic carbonates over heterogeneous catalysts [J]. Appl. Catal. A: Gen., 2009, 366 (1): 2-12. DOI: 10.1016/j.apcata.2009.06.045.
[24]	SAKAKURA T, KOHNO K. The synthesis of organic carbonates from carbon dioxide [J]. Chem. Commun., 2009, 47 (11): 1312-1330. DOI: 10.1039/B819997C.
[25]	MARTÍN C, FIORANI G, KLEIJ A W. Recent advances in the catalytic preparation of cyclic organic carbonates [J]. ACS Catal., 2015, 5 (2): 1353-1370. DOI: 10.1021/cs5018997.
[26]	KASUGA K, KABATA N. The fixation of carbon dioxide with 1,2-epoxypropane catalyzed by alkali-metal halide in the presence of a crown ether [J]. Inorg. Chim. Acta, 1997, 257 (2): 277-278. DOI: 10.1016/S0020-1693 (96)05481-3.
[27]	唐占忠, 彦陈, 瞿志坚, 等. 碳酸乙烯酯的合成研究 [J]. 石油化工, 1996, 25 (6): 409-413.TANG Z Z,CHEN Y, QU Z F, et al. Study on synthesis of ethylene carbonate [J]. Petrochemical Technology, 1996, 25 (6): 409-413.
[28]	KUMAR S, JAIN S L. Polyethylene glycol wrapped potassium bromide assisted chemical fixation of carbon dioxide [J]. Ind. Eng. Chem. Res., 2013, 53 (2): 541-546. DOI: 10.1021/ie4033439.
[29]	SONG J, ZHANG Z, HAN B, et al. Synthesis of cyclic carbonates from epoxides and CO2 catalyzed by potassium halide in the presence of b-cyclodextrin [J]. Green Chem., 2008, 10 (12): 1337-1341. DOI: 10.1039/B815105A.
[30]	MA J, LIU J, ZHANG Z, et al. The catalytic mechanism of KI and the co-catalytic mechanism of hydroxyl substances for cycloaddition of CO2 with propylene oxide [J]. Green Chem., 2012, 14 (9): 2410-2420. DOI: 10.1039/C2GC35711A.
[31]	LIANG S, LIU H, JIANG T, et al. Highly efficient synthesis of cyclic carbonates from CO2 and epoxides over cellulose/KI [J]. Chem. Commun., 2011, 47 (7): 2131-2133. DOI: 10.1039/C0CC04829A.
[32]	WU Z, XIE H, YU X, et al. Lignin-based green catalyst for the chemical fixation of carbon dioxide with epoxides to form cyclic carbonates under solvent-free conditions [J]. ChemCatChem, 2013, 5 (6): 1328-1333. DOI: 10.1002/cctc.201200894.
[33]	ZHOU L, LIU Y, HE Z, et al. Pentaerythritol and KI: an efficient catalytic system for the conversion from CO2 and epoxides to cyclic carbonates [J]. J. Chem. Res., 2013, (2): 102-104. DOI: 10.3184/174751913x13571500195988.
[34]	RAMIDI P, MUNSHI P, GARTIA Y, et al. Synergistic effect of alkali halide and Lewis base on the catalytic synthesis of cyclic carbonate from CO2 and epoxide [J]. Chem. Phys. Lett., 2011, 512 (4/5/6): 273-277. DOI: 10.1016/j.cplett.2011.07.035.
[35]	WERNER T, TENHUMBERG N. Synthesis of cyclic carbonates from epoxides and CO2 catalyzed by potassium iodide and amino alcohols [J]. J. CO2 Utili., 2014, 7 (7): 39-45. DOI: 10.1016/j.jcou.2014.04.002.
[36]	XIAO B, SUN J, WANG J, et al. Triethanolamine/KI: a multifunctional catalyst for CO2 activation and conversion with epoxides into cyclic carbonates [J]. Synthetic. Commun., 2013, 43 (22): 2985-2997. DOI: 10.1080/00397911.2012.754471.
[37]	YANG Z, SUN J, LIU X, et al. Nano-sized polydopamine-based biomimetic catalyst for the efficient synthesis of cyclic carbonates [J]. Tetrahedron Lett., 2014, 55 (21): 3239-3243. DOI: 10.1016/j.tetlet.2014.04.033.
[38]	ROSHAN K R, KATHALIKKATTIL A C, THARUN J, et al. Amino acid/KI as multi-functional synergistic catalysts for cyclic carbonate synthesis from CO2 under mild reaction conditions: a DFT corroborated study [J]. Dalton Trans., 2014, 43 (5): 2023-2031. DOI: 10.1039/C3DT52830H.
[39]	YANG Z, SUN J, CHENG W, et al. Biocompatible and recyclable amino acid binary catalyst for efficient chemical fixation of CO2 [J]. Catal. Commun., 2014, 44: 6-9. DOI: 10.1016/j.catcom.2013.07.025.
[40]	WERNER T, TENHUMBERG N, BÜTTNER H. Hydroxyl-functionalized imidazoles: highly active additives for the potassium iodide-catalyzed synthesis of 1,3-Dioxolan-2-one derivatives from epoxides and carbon dioxide [J]. ChemCatChem, 2014, 6 (12): 3493-3500. DOI: 10.1002/cctc.201402572.
[41]	SONG J, ZHANG B, ZHANG P, et al. Highly efficient synthesis of cyclic carbonates from CO2 and epoxides catalyzed by KI/lecithin [J]. Catal. Today, 2012, 183 (1): 130-135. DOI: 10.1016/j.cattod.2011.08.042.
[42]	LU X, ZHANG Y, JIN K, et al. Highly active electrophile-nucleophile catalyst system for the cycloaddition of CO2 to epoxides at ambient temperature [J]. J. Catal., 2004, 227 (2): 537-541. DOI: 10.1016/j.jcat.2004.07.018.
[43]	BAI D, NIAN G, WANG G, et al. Titanocene dichloride/KI: an efficient catalytic system for synthesis of cyclic carbonates from epoxides and CO2 [J]. Appl. Organomet. Chem., 2013, 27 (3): 184-187. DOI: 10.1002/aoc.2967.
[44]	CALO V, NACCI A, MONOPOLI A, et al. Cyclic carbonate formation from carbon dioxide and oxiranes in tetrabutylammonium halides as solvents and catalysts [J]. Org. Lett., 2002, 4 (15): 2561-2563. DOI: 10.1021/ol026189w.
[45]	SUN J, FUJITA S I, ZHAO F, et al. A highly efficient catalyst system of ZnBr2/n-Bu4NI for the synthesis of styrene carbonate from styrene oxide and supercritical carbon dioxide [J]. Appl. Catal. A: Gen., 2005, 287 (2): 221-226. DOI: 10.1016/j.apcata.2005.03.035.
[46]	SUN J, WANG L, ZHANG S, et al. ZnCl2/phosphonium halide: an efficient Lewis acid/base catalyst for the synthesis of cyclic carbonate [J]. J. Mol. Catal. A: Chem., 2006, 256 (1/2): 295-300. DOI: 10.1016/j.molcata.2006.05.004.
[47]	WU S, ZHANG X, DAI W, et al. ZnBr2-Ph4PI as highly efficient catalyst for cyclic carbonates synthesis from terminal epoxides and carbon dioxide [J]. Appl. Catal. A: Gen., 2008, 341 (1/2): 106-111. DOI: 10.1016/j.apcata.2008.02.021.
[48]	DELIA V, DUTTA B, SOFACK-KREUTZER J, et al. Nucleophile-directed selectivity towards linear carbonates in the niobium pentaethoxide-catalysed cycloaddition of CO2 and propylene oxide [J]. Catal. Sci. Technol., 2014, 4 (6): 1534-1538. DOI: 10.1039/C4CY00003J.
[49]	WHITEOAK C J, NOVA A, MASERAS F, et al. Merging sustainability with organocatalysis in the formation of organic carbonates by using CO2 as a feedstock [J]. ChemSusChem, 2012, 5 (10): 2032-2038. DOI: 10.1002/cssc.201200255.
[50]	WILHELM M E, ANTHOFER M H, COKOJA M, et al. Cycloaddition of carbon dioxide and epoxides using pentaerythritol and halides as dual catalyst system [J]. ChemSusChem, 2014, 7 (5): 1357-1360. DOI: 10.1021/cr300430e.
[51]	HARDMAN-BALDWIN A M, MATTSON A E. Silanediol-catalyzed carbon dioxide fixation [J]. ChemSusChem, 2014, 7 (12): 3275-3278. DOI: 10.1002/cssc.201402783.
[52]	WANG J, SUN J, CHENG W, et al. Experimental and theoretical studies on hydrogen bond-promoted fixation of carbon dioxide and epoxides in cyclic carbonates [J]. Phys. Chem. Chem. Phys., 2012, 14 (31): 11021-11026. DOI: 10.1039/C2CP41698K.
[53]	SUN J, REN J, ZHANG S, et al. Water as an efficient medium for the synthesis of cyclic carbonate [J]. Tetrahedron Lett., 2009, 50: 423-426. DOI: 10.1016/j.tetlet.2008.11.034.
[54]	FOLTRAN S, MEREAU R, TASSAING T. Theoretical study on the chemical fixation of carbon dioxide with propylene oxide catalyzed by ammonium and guanidinium salts [J]. Catal. Sci. Technol., 2014, 4 (6): 1585-1597. DOI: 10.1039/C3CY00955F.
[55]	WANG J, DONG K, CHENG W, et al. Insights into quaternary ammonium salts-catalyzed fixation carbon dioxide with epoxides [J]. Catal. Sci. Technol., 2012, 2 (7): 1480-1484. DOI: 10.1039/C2CY20103H.
[56]	PENG J, DENG Y. Cycloaddition of carbon dioxide to propylene oxide catalyzed by ionic liquids [J]. New J. Chem., 2001, 25 (4): 639-641. DOI: 10.1039/b008923k.
[57]	KIM Y J, CHEONG M. Chemical fixation of carbon dioxide to propylene carbonate in ionic liquids [J]. B. Kor. Chem. Soc., 2002, 27 (7): 1027-1028.
[58]	LI F, XIAO L, XIA C, et al. Chemical fixation of CO2 with highly efficient ZnCl2/[BMIm]Br catalyst system [J]. Tetrahedron Lett., 2004, 45 (45): 8307-8310. DOI: 10.1016/j.tetlet.2004.09.074.
[59]	SUN J, FUJITA S I, ZHAO F, et al. Synthesis of styrene carbonate from styrene oxide and carbon dioxide in the presence of zinc bromide and ionic liquid under mild conditions [J]. Green Chem., 2004, 6 (12): 613-616. DOI: 10.1039/B413229G.
[60]	WILHELM M E, ANTHOFER M H, REICH R M, et al. Niobium (Ⅴ) chloride and imidazolium bromides as efficient dual catalyst system for the cycloaddition of carbon dioxide and propylene oxide [J]. Catal. Sci. Technol., 2014, 4 (6): 1638-1643. DOI: 10.1039/C3CY01057K.
[61]	SHIELS R A, JONES C W. Homogeneous and heterogeneous 4-(N,N-dialkylamino)pyridines as effective single component catalysts in the synthesis of propylene carbonate [J]. J. Mol. Catal. A: Chem., 2007, 261 (2): 160-166. DOI: 10.1016/j.molcata.2006.08.002.
[62]	JING H, NGUYEN S T. SnCl4-organic base: highly efficient catalyst system for coupling reaction of CO2 and epoxides [J]. J. Mol. Catal. A: Chem., 2007, 261: 12-15. DOI: 10.1016/j.molcata.2006.07.057.
[63]	SEO U R, CHUNG Y K. Poly(4-vinylimidazolium)s/diazabicyclo [5.4.0]undec-7-ene/Zinc(II) bromide-catalyzed cycloaddition of carbon dioxide to epoxides [J]. Adv. Synth. Catal., 2014, 356 (9): 1955-1961. DOI: 10.1002/adsc.201400047.
[64]	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]. J. Catal., 2005, 232 (1): 80-84. DOI: 10.1016/j.jcat.2005.01.033.
[65]	LIU X, CAO C, LI Y, et al. Cycloaddition of CO2 to epoxides catalyzed by N-Heterocyclic carbene NHC-ZnBr2 system under mild conditions [J]. Synlett, 2012, (9): 1343-1348. DOI: 10.1055/s-0031-1290957.
[66]	ZHONG S, LIANG L, LIU B, et al. ZnBr2/DMF as simple and highly active Lewis acid-base catalysts for the cycloaddition of CO2 to propylene oxide [J]. J. CO2 Utili., 2014, 6: 75-79. DOI: 10.1016/j.jcou.2014.02.004.
[67]	LIU M, LIU B, SHI L, et al. Melamine-ZnI2 as heterogeneous catalysts for efficient chemical fixation of carbon dioxide to cyclic carbonates [J]. RSC Adv., 2015, 5 (2): 960-966. DOI: 10.1039/c4ra11460d.
[68]	LIU M, LIU B, ZHONG S, et al. Kinetics and mechanistic insight into efficient fixation of CO2 to epoxides over N-heterocyclic compound/ZnBr2 catalysts [J]. Ind. Eng. Chem. Res., 2015, 54: 633-640. DOI: 10.1021/ie5042879.
[69]	HOU Z, CHEN A, CHEN C, et al. Niobate salts of organic base catalyzed chemical fixation of carbon dioxide with epoxides to form cyclic carbonates [J]. Green Chem., 2015, 17 (3): 1842-1852. DOI: 10.1039/C4GC02244K.
[70]	D'ELIA V, GHANI A A, MONASSIER A, et al. Dynamics of the NbCl5-catalyzed cycloaddition of propylene oxide and CO2: assessing the dual role of the nucleophilic Co-catalysts [J]. Chem. Eur. J., 2014, 20 (37): 11870-11882. DOI: 10.1002/chem.201400324.
[71]	MONASSIER A, D'ELIA V, COKOJA M, et al. Synthesis of cyclic carbonates from epoxides and CO2 under mild conditions using a simple, highly efficient niobium-based catalyst [J]. ChemCatChem, 2013, 5 (6): 1321-1324. DOI: 10.1002/cctc.201200916.
[72]	SHEN Y, DUAN W, SHI M. Phenol and organic bases Co-catalyzed chemical fixation of carbon dioxide with terminal epoxides to form cyclic carbonates [J]. Adv. Synth. Catal., 2003, 345 (3): 337-340. DOI: 10.1002/adsc.200390035.
[73]	SHEN Y, DUAN W, SHI M. Chemical fixation of carbon dioxide Co-catalyzed by a combination of Schiff bases or phenols and organic bases [J]. Eur. J. Org. Chem., 2004, 2004 (14): 3080-3089. DOI: 10.1002/ejoc.200400083.
[74]	SUN J, CHENG W, YANG Z, et al. Superbase/cellulose: an environmental benign catalyst for chemical fixation of carbon dioxide into cyclic carbonates [J]. Green Chem., 2014, 16 (6): 3071-3078. DOI: 10.1039/C3GC41850B.
[75]	KAWANAMI H, IKUSHIMA Y. Chemical fixation of carbon dioxide to styrene carbonateunder supercritical conditions with DMF in the absence of any additional catalysts [J]. Chem. Commun., 2000, (21): 2089-2090. DOI: 10.1039/B006682F.
[76]	KOZAK J A, WU J, SU X, et al. Bromine-catalyzed conversion of CO2 and epoxides to cyclic carbonates under continuous flow conditions [J]. J. Am. Chem. Soc., 2013, 135 (49): 18497-18501. DOI: 10.1021/ja4079094.
[77]	WANG L, LIN L, ZHANG G, et al. Synthesis of cyclic carbonates from CO2 and epoxides catalyzed by low loadings of benzyl bromide/DMF at ambient pressure [J]. Chem. Commun., 2014, 50 (94): 14813-14816. DOI: 10.1039/C4CC06791F.
[78]	ZHOU H, WANG Y, ZHANG W, et al. N-Heterocyclic carbene functionalized MCM-41 as an efficient catalyst for chemical fixation of carbon dioxide [J]. Green Chem., 2011, 13 (3): 644-650. DOI: 10.1039/C0GC00541J.
[79]	ZHOU Y, HU S, MA X, et al. Synthesis of cyclic carbonates from carbon dioxide and epoxides over betaine-based catalysts [J]. J. Mol. Catal. A: Chem., 2008, 284 (1/2): 52-57. DOI: 10.1016/j.molcata.2008.01.010.
[80]	DAI W, JIN B, LUO S, et al. Functionalized phosphonium-based ionic liquids as efficient catalysts for the synthesis of cyclic carbonate from expoxides and carbon dioxide [J]. Appl. Catal. A: Gen., 2014, 470 (470): 183-188. DOI: 10.1016/j.apcata.2013.10.060.
[81]	WERNER T, BÜTTNER H. Phosphorus-based bifunctional organocatalysts for the addition of carbon dioxide and epoxides [J]. ChemSusChem, 2014, 7 (12): 3268-3271. DOI: 10.1002/cssc.201402477.
[82]	CHENG W, XIAO B, SUN J, et al. Effect of hydrogen bond of hydroxyl-functionalized ammonium ionic liquids on cycloaddition of CO2 [J]. Tetrahedron Lett., 2015, 56 (11):1416-1419. DOI: 10.1016/j.tetlet.2015.01.174.
[83]	WANG L, LI P, JIN X, et al. Mechanism of fixation of CO2 in the presence of hydroxyl-functionalized quaternary ammonium salts [J]. J. CO2 Utili., 2015, 10: 113-119. DOI: 10.1016/j.jcou.2015.02.006.
[84]	SUN J, ZHANG S, CHENG W, et al. Hydroxyl-functionalized ionic liquid: a novel efficient catalyst for chemical fixation of CO2 to cyclic carbonate [J]. Tetrahedron Lett., 2008, 49 (22): 3588-3591. DOI: 10.1016/j.tetlet.2008.04.022.
[85]	WANG J, CHENG W, SUN J, et al. Efficient fixation of CO2 into organic carbonates catalyzed by 2-hydroxymethyl-functionalized ionic liquids [J]. RSC Adv., 2014, 4 (5): 2360-2367. DOI: 10.1039/C3RA45918G.
[86]	WANG L, JIN X, LI P, et al. Hydroxyl-functionalized ionic liquid promoted CO2 fixation according to electrostatic attraction and hydrogen bonding interaction [J]. Ind. Eng. Chem. Res., 2014, 53 (20): 8426-8435. DOI: 10.1021/ie501063f.
[87]	SUN J, HAN L, CHENG W, et al. Efficient acid-base bifunctional catalysts for the fixation of CO2 with epoxides under metal-and solvent-free conditions [J]. ChemSusChem, 2011, 4 (4): 502-507. DOI: 10.1002/cssc.201000305.
[88]	XIAO L, LV D, WU W. Brønsted acidic ionic liquids mediated metallic salts catalytic system for the chemical fixation of carbon dioxide to form cyclic carbonates [J]. Catal. Lett., 2011, 141 (12): 1838-1844. DOI: 10.1007/s10562-011-0682-3.
[89]	HAN L, CHOI S J, PARK M S, et al. Carboxylic acid functionalized imidazolium-based ionic liquids: efficient catalysts for cycloaddition of CO2 and epoxides [J]. React. Kinet. Mech. Cat., 2012, 106 (1): 25-35. DOI: 10.1007/s11144-011-0399-8.
[90]	YUE C, SU D, ZHANG X, et al. Amino-functional imidazolium ionic liquids for CO2 activation and conversion to form cyclic carbonate [J]. Catal. Lett., 2014, 144 (7): 1313-1321. DOI: 10.1007/s10562-014-1241-5.
[91]	XIAO L, LV D, SU D, et al. Influence of acidic strength on the catalytic activity of Brønsted acidic ionic liquids on synthesizing cyclic carbonate from carbon dioxide and epoxide [J]. J. Clean. Prod., 2014, 67 (67): 285-290. DOI: 10.1016/j.jclepro.2013.12.031.
[92]	XIAO L, SU D, YUE C, et al. Protic ionic liquids: a highly efficient catalyst for synthesis of cyclic carbonate from carbon dioxide and epoxides [J]. J. CO2 Utili., 2014, 6 (6): 1-6. DOI: 10.1016/j.jcou.2014.01.004.
[93]	ANTHOFER M H, WILHELM M E, COKOJA M, et al. Hydroxy-functionalized imidazolium bromides as catalysts for the cycloaddition of CO2 and epoxides to cyclic carbonates [J]. ChemCatChem, 2015, 7 (1): 94-98. DOI: 10.1002/cctc.201402754.
[94]	INOUE S, TAKEDA N. Reaction of carbon dioxide with tetraphenylporphinatoaluminium ethyl in visible light [J]. B. Chem. Soc. Jpn., 1977, 50 (4): 984-986. DOI: 10.1246/bcsj.50.984.
[95]	TAKEDA N, INOUE S. Activation of carbon dioxide by tetraphenylporphinatoaluminium methoxide. reaction with epoxide [J]. B. Chem. Soc. Jpn., 1978, 51 (12): 3564-3567. DOI: 10.1246/bcsj.51.3564.
[96]	AIDA T, INOUE S. Activation of carbon dioxide with aluminum porphyrin and reaction with epoxide. Studies on (tetraphenylporphinato)aluminum alkoxide having a long oxyalkylene chain as the alkoxide group [J]. J. Am. Chem. Soc., 1983, 105 (5): 1304-1309. DOI: 10.1021/ja00343a038.
[97]	QIN Y, GUO H, SHENG X, et al. Aluminum porphyrin complex with high activity and selectivity for cyclic carbonate synthesis [J]. Green Chem., 2015, 17 (5): 2853-2858. DOI: 10.1039/C4GC02310B.
[98]	KRUPER W J, DELLAR D D. Catalytic formation of cyclic carbonates from epoxides and CO2 with chromium metalloporphyrinates [J]. J. Org. Chem., 1995, 60 (3): 725-727. DOI: 10.1021/jo00108a042.
[99]	PADDOCK R L, HIYAMA Y, MCKAY J M, et al. Co(III) porphyrin/DMAP: an efficient catalyst system for the synthesis of cyclic carbonates from CO2 and epoxides [J]. Tetrahedron Lett., 2004, 45 (9): 2023-2026. DOI: 10.1016/j.tetlet.2003.10.101.
[100]	JIN L, JING H, CHANG T, et al. Metal porphyrin/phenyltrimethylammonium tribromide: high efficient catalysts for coupling reaction of CO2 and epoxides [J]. J. Mol. Catal. A: Chem., 2007, 261 (2): 262-266. DOI: 10.1016/j.molcata.2006.06.011.
[101]	BAI D, DUAN S, HAI L, et al. Carbon dioxide fixation by cycloaddition with epoxides, catalyzed by biomimetic metalloporphyrins [J]. ChemCatChem, 2012, 4 (11): 1752-1758. DOI: 10.1002/cctc.201200204.
[102]	柏东升, 王晓旋, 宋莹莹, 等, 双功能金属卟啉催化环氧化合物与CO2偶联反应合成环碳酸酯 [J]. 催化学报, 2010, 31 (2): 176-180. DOI: 10.3724/SP.J.1088.2010.90838.
	BAI D S, WANG X X, SONG Y Y, et al. Bifunctional metalloporphyrins-catalyzed coupling reaction of epoxides and CO2 to cyclic carbonates [J]. Chin. J. Catal., 2010, 31: 176-180. DOI: 10.1016/S1872-2067 (09)60044-9.
[103]	REN T G, LI W J, BU Z W, et al. CoCl(TPPyP), a novel bifunctional catalyst for the coupling reaction of carbon dioxide and propylene oxide [J]. J. Chem. Res., 2010, 34 (7): 361-364. DOI: 10.3184/030823410x12762744367622.
[104]	EMA T, MIYAZAKI Y, KOYAMA S, et al. A bifunctional catalyst for carbon dioxide fixation: cooperative double activation of epoxides for the synthesis of cyclic carbonates [J]. Chem. Commun., 2012, 48 (37): 4489-4491. DOI: 10.1039/C2CC30591G.
[105]	MAEDA C, TANIGUCHI T, OGAWA K, et al. Bifunctional catalysts based on m-phenylene-bridged porphyrin dimer and trimer platforms: synthesis of cyclic carbonates from carbon dioxide and epoxides [J]. Angew. Chem. Int. Ed., 2015, 54: 134-138. DOI: 10.1002/anie.201409729.
[106]	EMA T, MIYAZAKI Y, SHIMONISHI J, et al. Bifunctional porphyrin catalysts for the synthesis of cyclic carbonates from epoxides and CO2: structural optimization and mechanistic study [J]. J. Am. Chem. Soc., 2014, 136 (43): 15270-15279. DOI: 10.1021/ja507665a.
[107]	JI D, LU X, HE R. Syntheses of cyclic carbonates from carbon dioxide and epoxides with metal phthalocyanines as catalyst [J]. Appl. Catal. A: Gen., 2000, 203 (2): 329-333. DOI: 10.1016/S0926-860X (00)00500-7.
[108]	PADDOCK R L, NGUYEN S T. Chemical CO2 fixation: Cr(III) salen complexes as highly efficient catalysts for the coupling of CO2 and epoxides [J]. J. Am. Chem. Soc., 2001, 123 (46): 11498-11499.
[109]	ZHANG X, JIA Y, LU X, et al. Intramolecularly two-centered cooperation catalysis for the synthesis of cyclic carbonates from CO2 and epoxides [J]. Tetrahedron Lett., 2008, 49 (46): 6589-6592. DOI: 10.1016/j.tetlet.2008.09.035.
[110]	PADDOCK R L, NGUYEN S T. Chiral (salen)CoⅢ catalyst for the synthesis of cyclic carbonates [J]. Chem. Commun., 2004, 14 (14): 1622-1623. DOI: 10.1039/b401543f.
[111]	CHANG T, JING H, JIN L, et al. Quaternary onium tribromide catalyzed cyclic carbonate synthesis from carbon dioxide and epoxides [J]. J. Mol. Catal. A: Chem., 2007, 264 (1/2): 241-247. DOI: 10.1016/j.molcata.2006.08.089.
[112]	YAN P, JING H. Catalytic asymmetric cycloaddition of carbon dioxide and propylene oxide using novel chiral polymers of BINOL-salen-cobalt(Ⅲ) salts [J]. Adv. Synth. Catal., 2009, 351 (9): 1325-1332. DOI: 10.1002/adsc.200900137.
[113]	MIAO C, WANG J, WU Y, et al. Bifunctional metal-salen complexes as efficient catalysts for the fixation of CO2 with epoxides under solvent-free conditions [J]. ChemSusChem, 2008, 1 (3): 236-241. DOI: 10.1002/cssc.200700133.
[114]	CHANG T, JIN L, JING H. Bifunctional chiral catalyst for the synthesis of chiral cyclic carbonates from carbon dioxide and epoxides [J]. ChemCatChem, 2009, 1 (3): 379-383. DOI: 10.1002/cctc.200900135.
[115]	ROY T, KURESHY R I, KHAN N H, et al. Asymmetric cycloaddition of CO2 and an epoxide using recyclable bifunctional polymeric Co(Ⅲ) salen complexes under mild conditions [J]. Catal. Sci. Technol., 2013, 3 (10): 2661-2667. DOI: 10.1039/c3cy00325f.
[116]	LU X, FENG X, HE R. Catalytic formation of ethylene carbonate from supercritical carbon dioxide/ethylene oxide mixture with tetradentate Schiff-base complexes as catalyst [J]. Appl. Catal. A: Gen., 2002, 234 (1/2): 25-33. DOI: 10.1016/s0926-860x (02)00223-5.
[117]	LU X, HE R, BAI C. Synthesis of ethylene carbonate from supercritical carbon dioxide/ethylene oxide mixture in the presence of bifunctional catalyst [J]. J. Mol. Catal. A: Chem., 2002, 186 (1/2): 1-11. DOI: 10.1016/s1381-1169(01)00442-3.
[118]	LU X, ZHANG Y, LIANG B, et al. Chemical fixation of carbon dioxide to cyclic carbonates under extremely mild conditions with highly active bifunctional catalysts [J]. J. Mol. Catal. A: Chem., 2004, 210 (1/2): 31-34. DOI: 10.1016/j.molcata.2003.09.010.
[119]	TIAN D, LIU B, GAN Q, et al. Formation of cyclic carbonates from carbon dioxide and epoxides coupling reactions efficiently catalyzed by robust, recyclable one-component aluminum-salen complexes [J]. ACS Catal., 2012, 2 (9): 2029-2035. DOI: 10.1021/cs300462r.
[120]	TIAN D, LIU B, ZHANG L, et al. Coupling reaction of carbon dioxide and epoxides efficiently catalyzed by one-component aluminum-salen complex under solvent-free conditions [J]. J. Ind. Eng. Chem., 2012, 18 (4): 1332-1338. DOI: 10.1016/j.jiec.2012.01.034.
[121]	REN W, LIU Y, LU X. Bifunctional aluminum catalyst for CO2 fixation: regioselective ring opening of three-membered heterocyclic compounds [J]. J. Org. Chem., 2014, 79 (20): 9771-9777. DOI: 10.1021/jo501926p.
[122]	LUO R, ZHOU X, CHEN S, et al. Highly efficient synthesis of cyclic carbonates from epoxides catalyzed by salen aluminum complexes with built-in “CO2 capture” capability under mild conditions [J]. Green Chem., 2014, 16 (3): 1496-1506. DOI: 10.1039/C3GC42388C.
[123]	MELÉNDEZ J, NORTH M, PASQUALE R. Synthesis of cyclic carbonates from atmospheric pressure carbon dioxide using exceptionally active aluminium(salen) complexes as catalysts [J]. Eur. J. Inorg. Chem., 2007, 2007 (21): 3323-3326. DOI: 10.1002/ejic.200700521.
[124]	NORTH M, PASQUALE R. Mechanism of cyclic carbonate synthesis from epoxides and CO2 [J]. Angew. Chem. Int. Ed., 2009, 48 (16): 2946-2948. DOI: 10.1002/anie.200805451.
[125]	CLEGG W, HARRINGTON R, NORTH M, et al. Cyclic carbonate synthesis catalysed by bimetallic aluminium-salen complexes [J]. Chem. Eur. J., 2010, 16 (23): 6828-6843. DOI: 10.1002/chem.201000030.
[126]	MELENDEZ J, NORTH M, VILLUENDAS P. One-component catalysts for cyclic carbonate synthesis [J]. Chem. Commun., 2009, 18 (18): 2577-2579. DOI: 10.1039/B900180H.
[127]	MELENDEZ J, NORTH M, VILLUENDAS P, et al. One-component bimetallic aluminium(salen)-based catalysts for cyclic carbonate synthesis and their immobilization [J]. Dalton Trans., 2011, 40 (15): 3885-3902. DOI: 10.1039/C0DT01196G.
[128]	NORTH M, VILLUENDAS P, YOUNG C. Inter-and intramolecular phosphonium salt cocatalysis in cyclic carbonate synthesis catalysed by a bimetallic aluminium(salen) complex [J]. Tetrahedron Lett., 2012, 53 (22): 2736-2740. DOI: 10.1016/j.tetlet.2012.03.090.
[129]	JING H, EDULJI S K, GIBBS J M, et al. (Salen)Tin complexes: syntheses, characterization, crystal structures, and catalytic activity in the formation of propylene carbonate from CO2 and oropylene oxide [J]. Inorg. Chem., 2004, 43 (14): 4315-4327. DOI: 10.1021/ic034855z.
[130]	SHEN Y, DUAN W, SHI M. Chemical fixation of carbon dioxide catalyzed by binaphthyldiamino Zn, Cu, and Co salen-type complexes [J]. J. Org. Chem., 2003, 68 (4): 1559-1562. DOI: 10.1021/jo020191j.
[131]	JUTZ F, GRUNWALDT J D, BAIKER A. Mn(Ⅲ)(salen)-catalyzed synthesis of cyclic organic carbonates from propylene and styrene oxide in “supercritical” CO2 [J]. J. Mol. Catal. A: Chem., 2008, 279 (1): 94-103. DOI: 10.1016/j.molcata.2007.10.010.
[132]	JUTZ F, GRUNWALDT J D, BAIKER A. In situ XAS study of the Mn(III)(salen)Br catalyzed synthesis of cyclic organic carbonates from epoxides and CO2 [J]. J. Mol. Catal. A: Chem., 2009, 297 (2): 63-72. DOI: 10.1016/j.molcata.2008.10.009.
[133]	COLETTI A, WHITEOAK C J, CONTE V, et al. Vanadium catalyzed synthesis of cyclic organic carbonates [J]. ChemCatChem, 2012, 4 (8): 1190-1196. DOI: 10.1002/cctc.201100398.
[134]	DECORTES A, MARTINEZ B M, BENET-BUCHHOLZ J, et al. Efficient carbonate synthesis under mild conditions through cycloaddition of carbon dioxide to oxiranes using a Zn(salphen) catalyst [J]. Chem. Commun., 2010, 46 (25): 4580-4582. DOI: 10.1039/C000493F.
[135]	DECORTES A, KLEIJ A W. Ambient fixation of carbon dioxide using a ZnIIsalphen catalyst [J]. ChemCatChem, 2011, 3 (5): 831-834. DOI: 10.1002/cctc.201100031.
[136]	TAHERIMEHR M, DECORTES A, AL-AMSYAR S M, et al. A highly active Zn(salphen) catalyst for production of organic carbonates in a green CO2 medium [J]. Catal. Sci. Technol., 2012, 2 (11): 2231-2237.
[137]	ESCÁRCEGA B M V, MARTÍNEZ B M, MARTIN E, et al. A recyclable trinuclear bifunctional catalyst derived from a tetraoxo bis-Zn(salphen) metalloligand [J]. Chem. Eur. J., 2013, 19 (8): 2641-2648. DOI: 10.1002/chem.201204132.
[138]	CASTRO G F, SALASSA G, KLEIJ A W, et al. A DFT study on the mechanism of the cycloaddition reaction of CO2 to epoxides catalyzed by Zn(salphen) complexes [J]. Chem. Eur. J., 2013, 19 (20): 6289-6298. DOI: 10.1002/chem.201203985.
[139]	MARTIN C, WHITEOAK C J, MARTIN E, et al. Easily accessible bifunctional Zn(salpyr) catalysts for the formation of organic carbonates [J]. Catal. Sci. Technol., 2014, 4 (6): 1615-1621. 10.1039/C3CY01043K.
[140]	REN Y, CHEN J, QI C, et al. A new type of Lewis acid-base bifunctional M(salphen) (M Zn, Cu and Ni) Catalysts for CO2 Fixation [J]. ChemCatChem, 2015, 7 (10): 1535-1538. DOI: 10.1002/cctc.201500113.
[141]	KIM H S, KIM J J, LEE B G, et al. Isolation of a pyridinium alkoxy ion bridged dimeric zinc complex for the coupling reactions of CO2 and epoxides [J]. Angew. Chem. Int. Ed., 2000, 39 (22): 4096-4098. DOI: 10.1002/1521-3773(20001117).
[142]	KIM H S, KIM J J, LEE S D, et al. New mechanistic insight into the coupling reactions of CO2 and epoxides in the presence of zinc complexes [J]. Chem. Eur. J., 2003, 9 (3): 678-686. DOI: 10.1002/chem.200390076.
[143]	LUO R, ZHOU X, ZHANG W, et al. New bi-functional zinc catalysts based on robust and easy-to-handle N-chelating ligands for the synthesis of cyclic carbonates from epoxides and CO2 under mild conditions [J]. Green Chem., 2014, 16 (9): 4179-4189. DOI: 10.1039/C4GC00671B.
[144]	WHITEOAK C J, KIELLAND N, LASERNA V, et al. Highly active aluminium catalysts for the formation of organic carbonates from CO2 and oxiranes [J]. Chem. Eur. J., 2014, 20 (8): 2264-2275. DOI: 10.1002/chem.201302536.
[145]	STYRING P, SUPASITMONGKOL S. A single centre aluminium(III) catalyst and TBAB as an ionic organo-catalyst for the homogeneous catalytic synthesis of styrene carbonate [J]. Catal. Sci. Technol., 2014, 4 (6): 1622-1630. DOI: 10.1039/C3CY01015E.
[146]	CASTRO-OSMA J A, ALONSO-MORENO C, LARA-SANCHEZ A, et al. Synthesis of cyclic carbonates catalysed by aluminium heteroscorpionate complexes [J]. Catal. Sci. Technol., 2014, 4 (6): 1674-1684. DOI: 10.1039/C3CY00810J.
[147]	CASTRO-OSMA J A, LARA-SANCHEZ A, NORTH M, et al. Synthesis of cyclic carbonates using monometallic, and helical bimetallic, aluminium complexes [J]. Catal. Sci. Technol., 2012, 2 (5): 1021-1026. DOI: 10.1039/C2CY00517D.
[148]	QIN J, WANG P, LI Q, et al. Catalytic production of cyclic carbonates mediated by lanthanide phenolates under mild conditions [J]. Chem. Commun., 2014, 50 (75): 10952-10955. DOI: 10.1039/C4CC02065K.
[149]	BUONERBA A, DE NISI A, GRASSI A, et al. Novel iron(Ⅲ) catalyst for the efficient and selective coupling of carbon dioxide and epoxides to cyclic carbonates [J]. Catal. Sci. Technol., 2015, 5 (1): 118-123. DOI: 10.1039/C4CY01187B.

Acid-base synergistic effect promoted cycloaddition reaction from CO₂ with epoxide in homogenous catalysis systems

均相体系中酸碱协同催化二氧化碳与环氧化物的环加成反应

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