中文
Earlier issues
Announcement
More
Progress in Chemistry 2012, Vol. 24 Issue (05): 674-685 Previous Articles   Next Articles

• Review •

Synthesis of Cyclic Carbonates from CO2 and Epoxides Catalyzed by Ionic Liquids

Zhang Yuanyuan, Luo Shenglian, Yin Shuangfeng   

  1. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China
  • Received: Revised: Online: Published:
PDF ( 1589 ) Cited
Export

EndNote

Ris

BibTeX

This review summarizes the research progress on the use of ionic liquids(ILs) as catalysts for the cycloaddition of CO2 with epoxides to prepare cyclic carbonates. The reported ILs for this reaction include imidazole salt, quaternary ammonium salt, quaternary phosphonium salt, and so on. Systematical comparison has been made between the conventional ILs and functional ILs in the terms of their catalytic performances and reaction mechanisms. Generally, the conventional ILs show poor catalytic efficiency towards this coupling reaction, thus co-catalysts are usually needed to improve their catalytic activity. Compared with conventional ILs, functionalized ILs show much better catalytic performance due to the synergistic effect between hydroxyl or carboxylic acid group and Lewis base such as halide anions. As to the supported ILs catalysts, inorganic material SiO2 is the most common support for immobilizing or supporting ILs catalysts.In the recent years, mesoporous materials such as SBA-15 and MCM-41 whose surfaces are of hydroxyl groups can also be used to immobilize ILs. Besides inorganic materials, polymers are another type of important supports, and the polymers-supported ILs are more stable than ILs on inorganic supports. Moreover, there is synergistic effect between the active components and supports of the immobilized functional ILs, resulting in better catalytic performance. It is emphasized that supported ILs catalysts have good potential applications in industry since they show good catalytic activity, selectivity and recyclability. What's more, ILs can also be used as catalysts for the preparation of chiral cyclic carbonates with good yield and enantioselectivity.

Contents
1 Introduction
2 Homogeneous ionic liquid catalysts
2.1 Traditional ionic liquid catalysts
2.2 Functional ionic liquid catalysts
3 Heterogeneous ionic liquid catalysts
3.1 Ionic liquid catalysts immobilized on inorganic materials
3.2 Ionic liquid catalysts immobilized on polymers
4 Ionic liquids used in preparation of chiral cyclic carbonates
5 Conclusions and outlook

Key words: carbon dioxide, epoxide, cyclic carbonate, ionic liquids

CLC Number: 

[1] Du Y, Cai F, Kong D L, He L N. Green Chem., 2005, 7: 518—523
[2] Sakakura T, Choi J C, Yasuda H. Chem. Rev., 2007, 107: 2365—2387
[3] Clements J H. Ind. Eng. Chem. Res., 2003, 42: 663—674
[4] Shaikh A A G, Sivaram S. Chem. Rev., 1996, 96: 951—976
[5] Sun J M, Fujita S I, Arai M. J. Organomet. Chem., 2005, 690: 3490—3497
[6] 赵正康(Zhao Z K), 李娟(Li J), 吕志果(Lv Z G). 精细石油化工进展(Advances in Fine Petrochemicals), 2009, 10(6): 36—41
[7] Olivier H. J. Mol. Catal. A: Chem., 1999, 146(1/2): 285—289
[8] 彭家建(Peng J J), 邓友全(Deng Y Q). 催化学报(Chinese Journal of Catalysis), 2001, 22(6): 598—600
[9] Kawanami H, Sasaki A, Matsui K, Ikushima Y. Chem. Commun., 2003, 39: 896—897
[10] Lee E H, Ahn J Y, Dharman M M, Park D W, Park S W, Kim I. Catal. Today, 2008, 131: 130—134
[11] Li F W, Xiao L F, Xia C G, Hu B. Tetrahedron Lett., 2004, 45: 8307—8310
[12] Sun J M, Fujita S I, Zhao F Y, Arai M. Green Chem., 2004, 6: 613—616
[13] Zhou Y X, Hu S Q, Ma X M, Liang S G, Jiang T, Han B X. J. Mol. Catal. A: Chem., 2008, 284: 52—57
[14] Ju H Y, Ahn J Y, Manju M D, Kim K H, Park D W. Korean J. Chem. Eng., 2008, 25(3): 471—473
[15] Kim H S, Kim J J, Kim H, Jang H G. J. Catal., 2003, 220: 44—46
[16] Fujita S I, Nishiura M, Arai M. Catal. Lett., 2010, 135: 263—268
[17] Nguyen L V, Lee B, Nguyen D Q, Kang M J, Lee H, Ryu S, Kim H S, Lee J S. Bull. Korean Chem. Soc., 2008, 29(1): 148—152
[18] Calo V, Nacci A, Monopoli A, Fanizzi A. Org. Lett., 2002, 4(15): 2561—2563
[19] Sun J, Ren J Y, Zhang S J, Cheng W G. Tetrahedron Lett., 2009, 50: 423—426
[20] 李扬(Li Y), 朱培玉(Zhu P Y), 王延儒(Wang Y R). 南京师范大学学报(工程技术版)(Journal of Nanjing Normal University(Engineering and Technology Edition)), 2007, 7(1): 59—62
[21] Sun J M, Fujita S I, Zhao F Y, Hasegawa M, Arai M. J. Catal., 2005, 230: 398—405
[22] Ono F, Qiao K, Tomida D, Yokoyama C. J. Mol. Catal. A: Chem., 2007, 263: 223—226
[23] Gomes C R, Ferreira D M, Constantino C J L, Gonzalez E R P. Tetrahedron Lett., 2008, 49: 6879—6881
[24] Ion A, Parvulescu V, Jacobs P, Vos D. Appl. Catal. A, 2009, 363: 40—44
[25] Du Y, Wang J Q, Chen J Y, Cai F, Tian J S, Kong D L, He L N. Tetrahedron Lett., 2006, 47: 1271—1275
[26] Dou X Y, Wang J Q, Du Y, Wang E, He L N. Synlett, 2007, 19: 3058—3062
[27] Sun D W, Zhai H J. Catal. Commun., 2007, 8: 1027—1030
[28] 赵彬(Zhao B), 陈殿军(Chen D J), 李永路(Li Y L), 蒋景阳(Jiang J Y). 分子催化(Journal of Molecular Catalysis), 2008, 22(6): 487—490
[29] Yang Z Z, He L N, Miao C X, Chanfreau S. Adv. Synth. Catal., 2010, 352: 2233 — 2240
[30] He L N, Yasuda H, Sakakura T. Green Chem., 2003, 5: 92—94
[31] Sun J, Wang L, Zhang S J, Li Z X, Zhang X P, Dai W B, Mori R. J. Mol. Catal. A: Chem., 2006, 256: 295—300
[32] Sun J, Han L J, Cheng W G, Wang J Q, Zhang X P, Zhang S J. ChemSusChem, 2011, 4(4): 502—507
[33] Wu S S, Zhang X W, Dai W L, Yin S F, Li W S, Ren Y Q, Au C T. Appl. Catal. A, 2008, 341: 106—111
[34] He J L, Wu T B, Zhang Z F, Ding K L, Han B X, Xie Y, Jiang T, Liu Z M. Chem. Eur. J., 2007, 13: 6992—6997
[35] Sun J, Cheng W G, Fan W, Wang Y H, Meng Z Y, Zhang S J. Catal. Today, 2009, 148: 361—367
[36] Tian J S, Miao C X, Wang J Q, Cai F, Du Y, Zhao Y, He L N. Green Chem., 2007, 9: 566—571
[37] Patil Y P, Tambade P J, Jagtap S R, Bhanage B M. J. Mol. Catal. A: Chem., 2008, 289: 14—21
[38] Sun J, Zhang S J, Cheng W G, Ren J Y. Tetrahedron Lett., 2008, 49: 3588—3591
[39] Zhang X H, Zhao N, Wei W, Sun Y H. Catal. Today, 2006, 115: 102—106
[40] Zhu A L, Jiang T, Han B X, Zhang J C, Xie Y, Ma X M. Green Chem., 2007, 9: 169—172
[41] Dai W L, Chen L, Yin S F, Luo S L, Au C T. Catal. Lett., 2010, 135: 295—304
[42] Dai W L, Chen L, Yin S F, Li W H, Zhang Y Y, Luo S L, Au C T. Catal. Lett., 2010, 137: 74—80
[43] Wu F, Dou X Y, He L N, Miao C X. Lett. Org. Chem., 2010, 7: 73—78
[44] Xiao L F, Li F W, Peng J J, Xia C G. J. Mol. Catal. A: Chem., 2006, 253: 265—269
[45] Sakai T, Tsutsumi Y, Ema T. Green Chem., 2008, 10: 337—341
[46] Udayakumar S, Raman V, Shim H L, Park D W. Appl. Catal. A, 2009, 368: 97—104
[47] Motokura K, Itagaki S, Iwasawa Y, Miyaji A, Baba T. Green Chem., 2009, 11: 1876—1880
[48] 张学兰(Zhang X L), 王登峰(Wang D F), 李军平(Li J P), 赵宁(Zhao N), 肖福魁(Xiao F K), 魏伟(Wei W), 孙予罕(Sun Y H). 石油学报(石油加工)(Acta Petrolei Sinica(Petroleum Processing Section)), 2008, 24: 68—78
[49] Zhang X L, Wang D F, Zhao N, Al-Arifi A S N, Aouak T, Al-Othman Z A, Wei W, Sun Y H. Catal. Commun., 2009, 11: 43—46
[50] 张学兰(Zhang X L), Al-Arifi A S N, Aouak T, Al-Othman Z A, 魏伟(Wei W), 孙予罕(Sun Y H). 石油化工(Petrochemical Technology), 2009, 38(12): 1264—1269
[51] Xie Y, Ding K L, Liu Z M, Li J J, An G M, Tao R T, Sun Z Y, Yang Z Z. Chem. Eur. J., 2010, 16: 6687 — 6692
[52] Yu J I, Choi H J, Selvaraj M, Park D W. Reac. Kinet. Mech. Cat., 2011, 102: 353—365
[53] Wang J Q, Kong D L, Chen J Y, Cai F, He L N. J. Mol. Catal. A: Chem., 2006, 249: 143—148
[54] Wang J Q, Yue X D, Cai F, He L N. Catal. Commun., 2007, 8: 167—172
[55] Zhao Y, Tian J S, Qi X H, Han Z N, Zhuang Y Y, He L N. J. Mol. Catal. A: Chem., 2007, 271: 284—289
[56] Takahashi T, Watahiki T, Kitazume S, Yasuda H, Sakakura T. Chem. Commun., 2006, 42: 1664—1666
[57] 任占冬(Ren Z D), 朱玉婵(Zhu Y C). 现代化工(Modern Chemical Industry), 2009, 29(9): 43—45
[58] Xu L W, Yang M S, Jiang J X, Qiu H Y, Lai G Q. Cent. Eur. J. Chem., 2007, 5(4): 1073—1083
[59] Udayakumar S, Son Y S, Lee M K, Park S W, Park D W. Appl. Catal. A, 2008, 347: 192—199
[60] Udayakumar S, Park S W, Park D W, Choi B S. Catal. Commun., 2008, 9: 1563—1570
[61] Udayakumar S, Lee M K, Shim H L, Park S W, Park D W. Catal. Commun., 2009, 10: 659—664
[62] Udayakumar S, Lee M K, Shim H L, Park D W. Appl. Catal. A, 2009, 365: 88—95
[63] Dharman M M, Choi H J, Kim D W, Park D W. Catal. Today, 2011, 164(1): 544—547
[64] Zheng X X, Luo S Z, Zhang L, Cheng J P. Green Chem., 2009, 11: 455—458
[65] Han L N, Park S W, Park D W. Energy Environ. Sci., 2009, 2: 1286—1292
[66] Han L N, Choi H J, Kim D K, Park S W, Liu B Y, Park D W. J. Mol. Catal. A: Chem., 2011, 338: 58—64
[67] Bai D S, Wang Q, Song Y Y, Li B, Jing H W. Catal. Commun., 2011, 12: 684—688
[68] Lu X B, Liang B, Zhang Y J, Tian Y Z, Wang Y M, Bai C X, Wang H, Zhang R. J. Am. Chem. Soc., 2004, 126: 3732—3733
[69] Cho H C, Lee H S, Chun J, Lee S M, Kim H J, Son S U. Chem. Commun., 2011, 47: 917—919
[70] 任俊毅(Ren J Y), 王少君(Wang S J), 成卫国(Cheng W G), 孙剑(Sun J), 张锁江(Zhang S J), 王荣刚(Wang R G). 化工学报(Journal of Chemical Industry and Engineering), 2009, 60(6): 1471—1476
[71] Han L N, Choi H J, Choi S J, Liu B Y, Park D W. Green Chem., 2011, 13: 1023—1028
[72] Molinari H, Montanari F, Quici S, Tundo P. J. Am. Chem. Soc., 1979, 101: 3920—3927
[73] Nishikubo T, Kameyama A, Yamashita J, Tomoi M, Fukuda W. J. Polym. Sci. Part A: Polym. Chem., 1993, 31: 939—947
[74] Nishikubo T, Kameyama A, Yamashita J, Fukumitsu T, Maejima C, Tomoi M. J. Polym. Sci. Part A: Polym. Chem., 1995, 33: 1011—1017
[75] Kim J J, Shin D H, Lee H S, Park D W. Polym. Adv. Technol., 2003, 14: 521—528
[76] Park D W, Moon J Y, Jang H J, Kim K H. React. Kinet. Catal. Lett., 2001, 72(1): 83—92
[77] Park J Y, Kim J J, Kim K H, Moon J Y, Park D W. React. Kinet. Catal. Lett., 2001, 74(1): 29—40
[78] 熊玉兵(Xiong Y B), 崔紫鹏(Cui Z P), 王鸿(Wang H), 王玉娇(Wang Y J), 王荣民(Wang R M). 催化学报(Chinese Journal of Catalysis), 2010, 31(12): 1473—1477
[79] Xie Y, Zhang Z F, Jiang T, He J L, Han B X, Wu T B, Ding K L. Angew. Chem., 2007, 119: 7393—7396
[80] Ochiai B, Endo T. J. Polym. Sci. Part A: Polym. Chem., 2007, 45: 5673—5678
[81] Xiong Y B, Wang H, Wang R M, Yan Y F, Zheng B, Wang Y P. Chem. Commun., 2010, 46: 3399—3401
[82] Chen S W, Kawthekar R B, Kim G J. Tetrahedron Lett., 2007, 48: 297—300
[83] Berkessel A, Brandenburg M. Org. Lett., 2006, 8(20): 4401—4404
[84] Chang T, Jing H W, Jin L L, Qiu W Y. J. Mol. Catal. A: Chem., 2007, 264: 241—247
[85] Zhang S L, Huang Y Z, Jing H W, Yao W X, Yan P. Green Chem., 2009, 11: 935—938
[86] 张素玲(Zhang S L), 宋莹莹(Song Y Y), 景欢旺(Jing H W), 闫鹏(Yan P), 蔡强(Cai Q). 催化学报(Chinese Journal of Catalysis), 2009, 30(12): 1255—1260
[87] Jang D Y, Jang H G, Kim G R, Kim G J. Catal. Today, 2011, doi: 10. 1016/j. cattod. 2011. 08. 013
[1] Deshan Zhang, Chenho Tung, Lizhu Wu. Artificial Photosynthesis [J]. Progress in Chemistry, 2022, 34(7): 1590-1599.
[2] Fengshou Yu, Jiayu Zhan, Lu-Hua Zhang. The progress on Electrochemical CO2-to-Formate Conversion by p-Block Metal Based Catalysts [J]. Progress in Chemistry, 2022, 34(4): 983-991.
[3] Shujin Shen, Cheng Han, Bing Wang, Yingde Wang. Transition Metal Single-Atom Electrocatalysts for CO2 Reduction to CO [J]. Progress in Chemistry, 2022, 34(3): 533-546.
[4] Changfan Xu, Xin Fang, Jing Zhan, Jiaxi Chen, Feng Liang. Progress for Metal-CO2 Batteries: Mechanism and Advanced Materials [J]. Progress in Chemistry, 2020, 32(6): 836-850.
[5] Jing Wen, Yuhong Li, Li Wang, Xiunan Chen, Qi Cao, Naipu He. Carbon Dioxide Smart Materials Based on Chitosan [J]. Progress in Chemistry, 2020, 32(4): 417-422.
[6] Fengguo Liu, Bo Wang, Lianyu Zhang, Aimin Liu, Zhaowen Wang, Zhongning Shi. Application of Ionic Liquids in Aluminum and Alloy Electrodeposition [J]. Progress in Chemistry, 2020, 32(12): 2004-2012.
[7] Xingwang Lan, Guoyi Bai. Covalent Organic Framework Catalytic Materials: CO2 Conversion and Utilization [J]. Progress in Chemistry, 2020, 32(10): 1482-1493.
[8] Guobin Tong, Lei E, Zhou Xu, Chunhui Ma, Wei Li, Shouxin Liu. Preparation, Modification and Application of Carbon Materials Based on Ionic Liquids [J]. Progress in Chemistry, 2019, 31(8): 1136-1147.
[9] Mengru Yang, Huajing Li, Ningdan Luo, Jin Li, Anning Zhou, Yuangang Li. Electro-Chemical Reduction of Carbon Dioxide into Ethylene: Catalyst, Conditions and Mechanism [J]. Progress in Chemistry, 2019, 31(2/3): 245-257.
[10] Zhiyong Li, Ying Feng, Huiyong Wang, Xiaoqing Yuan, Yuling Zhao, Jianji Wang. Structure and Performance Modulation of Photo-Responsive Ionic Liquids [J]. Progress in Chemistry, 2019, 31(11): 1550-1559.
[11] Wenqiao Liu, Zhen Li, Chungu Xia. Preparation and Application of Acidic Ionic Liquid Hybrid Solid Catalytic Materials [J]. Progress in Chemistry, 2018, 30(8): 1143-1160.
[12] Yu Zhang, Jinghe Cen, Wenfang Xiong, Chaorong Qi, Huanfeng Jiang*. CO2: C1 Synthon in Carboxylation Reactions [J]. Progress in Chemistry, 2018, 30(5): 547-563.
[13] Mengyan Liu, Yuanshuang Wang, Wen Deng, Zhenhai Wen. Electrocatalytic Reduction of CO2 on Copper-Based Catalysts [J]. Progress in Chemistry, 2018, 30(4): 398-409.
[14] Haidong Cheng, Shuangjun Chen*. Degradation and Synthesis of Poly (Ethylene Terephthalate) by Functionalized Ionic Liquids [J]. Progress in Chemistry, 2017, 29(4): 443-449.
[15] Song Heyuan, Kang Meirong, Jin Ronghua, Jin Fuxiang, Chen Jing. Application of Ionic Liquids to the Carbonylation Reactions [J]. Progress in Chemistry, 2016, 28(9): 1313-1327.