Recent advances in porous organic polymers for the synthesis of cyclic carbonates from carbon dioxide

doi:10.16085/j.issn.1000-6613.2020-1502

Abstract

Abstract:

Recently, carbon dioxide (CO₂) capture utilization and storage (CCUS) has been generally identified as a potential strategy in the global energy transition, enabling the provision of energy and the production of essential materials, while limiting climate change. Due to their large capacity and excellent selectivity for the adsorption of CO₂, outstanding structural properties, as well as their chemical tunability, porous organic polymers (POPs) have been widely employed as efficient catalysts in numerous CO₂-involved reactions. In particular, the insertion of CO₂ into epoxides for affording cyclic carbonates has been proposed as a promising strategy due to its 100% atom economy and the great industrial potential of products. Based on the reaction mechanism together with the synthetic methods, structural properties and component characteristics of catalysts, the progress in POPs for the CO₂/epoxides cycloaddition reaction was reviewed, including metal complexes-, hydrogen-bond donor-, ionic liquids (ILs)-, metal complexes/ILs- and hydrogen-bond donor/ILs-based POPs. The research status and development trend of POPs in the transformation of CO₂ into value-added cyclic carbonate were described, which provided constructive guidance for the development and application of POPs and the industrial exploration of comprehensive utilization of CO₂.

Key words: carbon dioxide, cyclic carbonate, porous organic polymers, heterogeneous catalysis, ionic liquids, metal complex

摘要：

二氧化碳（CO₂）捕集、利用和储存（CCUS）在全球能源结构转型中是一种极具潜力的策略，能够实现能源供给、基础原料产出以及限制气候变化。多孔有机聚合物（POPs）具有高CO₂吸附容量和吸附选择性、突出的结构特性以及优异的化学可调控性，其作为极具潜力的材料广泛应用于催化CO₂参与的有机反应中。其中，CO₂与环氧化物环加成生成环状碳酸酯的反应具有100%的原子经济性，且其产物也极具工业价值。本文基于CO₂环加成反应催化机制，从催化剂的合成方法、结构性质与组成特性角度出发，综述了POPs在CO₂/环氧化物环加成反应的研究进展，包括金属配合物类、氢键供体类、离子液体类、金属配合物/离子液体和氢键供体/离子液体等有机多孔聚合物体系。通过阐述POPs在催化CO₂制备高附加值环状碳酸酯反应中的研究现状和发展趋势，为POPs的开发与应用以及CO₂综合利用的工业化探索提供具有建设性的指导意见。

关键词: 二氧化碳, 环状碳酸酯, 多孔有机聚合物, 多相催化, 离子液体, 金属配合物

CLC Number:

O643.3

CHEN Yaju, REN Qinggang, ZHOU Xiantai, JI Hongbing. Recent advances in porous organic polymers for the synthesis of cyclic carbonates from carbon dioxide[J]. Chemical Industry and Engineering Progress, 2021, 40(7): 3564-3583.

陈亚举, 任清刚, 周贤太, 纪红兵. 多孔有机聚合物催化二氧化碳合成环状碳酸酯研究进展[J]. 化工进展, 2021, 40(7): 3564-3583.

Figures/Tables 20

References 92

1	Agency International Energy. Global energy and CO₂ status report 2018[R]. Paris, 2019.
2	SAKAKURA Toshiyasu, CHOI Jun Chul, YASUDA Hiroyuki. Transformation of carbon dioxide[J]. Chemical Reviews, 2007, 107(6): 2365-2387.
3	LIU Qiang, WU Lipeng, JACKSTELL Ralf, et al. Using carbon dioxide as a building block in organic synthesis[J]. Nature Communications, 2015, 6: 5933-5947.
4	ARESTA Michele, DIBENEDETTO Angela, ANGELINI Antonella. Catalysis for the valorization of exhaust carbon: from CO₂to chemicals, materials, and fuels. technological use of CO₂[J]. Chemical Reviews, 2014, 114(3): 1709-1742.
5	NEVES GOMES Christophe DAS, JACQUET Olivier, VILLIERS Claude, et al. A diagonal approach to chemical recycling of carbon dioxide: organocatalytic transformation for the reductive functionalization of CO₂[J]. Angewandte Chemie International Edition, 2012, 51(1): 187-190.
6	Jürgen KLANKERMAYER, WESSELBAUM Sebastian, BEYDOUN Kassem, et al. Selective catalytic synthesis using the combination of carbon dioxide and hydrogen: catalytic chess at the interface of energy and chemistry[J]. Angewandte Chemie International Edition, 2016, 55(26): 7296-7343.
7	张文珍, 张宁, 郭春晓, 等. 二氧化碳参与的环化反应最新研究进展[J]. 有机化学, 2017, 37(6): 1309-1321.
	ZHANG Wenzhen, ZHANG Ning, GUO Chunxiao, et al. Recent progress in the cyclization reactions using carbon dioxide[J]. Chinese Journal of Organic Chemistry, 2017, 37(6): 1309-1321.
8	罗荣昌, 周贤太, 杨智, 等. 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.
	LUO Rongchang, ZHOU Xiantai, YANG Zhi, et al. Acid-base synergistic effect promoted cycloaddition reaction from CO₂ with epoxide in homogenous catalysis systems[J]. CIESC Journal, 2016, 67(1): 258-276.
9	BOOT-HANDFORD M E, ABANADES J C, ANTHONY E J, et al. Carbon capture and storage update[J]. Energy & Environmental Science, 2014, 7(1): 130-189.
10	Benjamin SCHÄFFNER, Friederike SCHÄFFNER, VEREVKIN Sergey P, et al. Organic carbonates as solvents in synthesis and catalysis[J]. Chemical Reviews, 2010, 110(8): 4554–4581.
11	SHAIKH Rafik Rajjak, PORNPRAPROM Suriyaporn, Valerio D'ELIA. Catalytic strategies for the cycloaddition of pure, diluted and waste CO₂ to epoxides under ambient conditions[J]. ACS Catalysis, 2018, 8(1): 419-450.
12	BARTHEL Alexander, SAIH Youssef, GIMENEZ Michel, et al. Highly integrated CO₂ capture and conversion: direct synthesis of cyclic carbonates from industrial flue gas[J]. Green Chemistry, 2016, 18(10): 3116-3123.
13	ROY Susmita, BANERJEE Biplab, BHAUMIL Asim, et al. CO₂ fixation at atmospheric pressure: porous ZnSnO₃ nanocrystals as a highly efficient catalyst for the synthesis of cyclic carbonates[J]. RSC Advances, 2016, 6(37): 31153-31160.
14	SUN Jian, HAN Lijun, CHENG Weiguo, et al. Efficient acid-base bifunctional catalysts for the fxation of CO₂ with epoxides under metal- and solvent-free conditions[J]. ChemSuschem, 2011, 4(4): 502-507.
15	杨美, 钟向宏, 陈群. 离子液体催化二氧化碳合成环状碳酸酯的研究进展[J]. 化工进展, 2017, 36(9): 3300-3308.
	YANG Mei, ZHONG Xianghong, CHEN Qun. Recent progress of the synthesis of cyclic carbonates from CO₂ and epoxides catalyzed by ionic liquids[J]. Chemical Industry and Engineering Progress, 2017, 36(9): 3300-3308.
16	FIORANI Giulia, GUO Wusheng, KLEIJ Arjan W. Sustainable conversion of carbon dioxide: the advent of organocatalysis[J]. Green Chemistry, 2015, 17(3): 1375-1389.
17	REN Weimin, LIU Ye, LU Xiaobing. Bifunctional aluminum catalyst for CO₂ fixation: regioselective ring opening of three-membered heterocyclic compounds[J]. The Journal of Organic Chemistry, 2014, 79(20): 9771-9777.
18	QIN Yusheng, GUO Hongchen, SHENG Xingheng, et al. An aluminum porphyrin complex with high activity and selectivity for cyclic carbonate synthesis[J]. Green Chemistry, 2015, 17(5): 2853-2858.
19	LUO Rongchang, ZHOU Xiantai, ZHANG Wuying, 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 Chemistry, 2014, 16(9): 4179-4189.
20	CHEN Yaju, LUO Rongchang, YANG Zhi, et al. Imidazolium-based ionic liquid decorated zinc porphyrin catalyst for converting CO₂ into five-membered heterocyclic molecules[J]. Sustainable Energy & Fuels, 2018, 2(1): 125-132.
21	JIANG Xu, GOU Faliang, CHEN Fengjuan, et al. Cycloaddition of epoxides and CO₂ catalyzed by bisimidazole-functionalized porphyrin cobalt(Ⅲ) complexes[J]. Green Chemistry, 2016, 18(12): 3567-3576.
22	Tadashi EMA, MIYAZAKI Yuki, SHIMONISHI Junta, et al. Bifunctional porphyrin catalysts for the synthesis of cyclic carbonates from epoxides and CO₂: structural optimization and mechanistic study[J]. Journal of the American Chemical Society, 2014, 136(43): 15270-15279.
23	CHEN Aibing, ZHANG Yunzhao, CHEN Jinzhu, et al. Metalloporphyrin-based organic polymers for carbon dioxide fixation to cyclic carbonate[J]. Journal of Materials Chemistry A, 2015, 3(18): 9807-9816.
24	GAO Wenyang, CHEN Yao, NIU Youhong, et al. Crystal engineering of an nbo topology metal-organic framework for chemical fixation of CO₂ under ambient conditions[J]. Angewandte Chemie International Edition, 2014, 53(10): 2615-2619.
25	WANG Jinquan, ZHANG Yugen. Facile synthesis of N-rich porous azo-linked frameworks for selective CO₂ capture and conversion[J]. Green Chemistry, 2016, 18(19): 5248-5253.
26	CHEN Jian, LI He, ZHONG Mingmei, et al. Hierarchical mesoporous organic polymer with intercalated metal complex for efficient synthesis of cyclic carbonates from flue gas[J]. Green Chemistry, 2016, 18(24): 6493-6500.
27	HUANG Kuan, ZHANG Jiayin, LIU Fujian, et al. Synthesis of porous polymeric catalysts for the conversion of carbon dioxide[J]. ACS Catalysis, 2018, 8(10): 9079-9102.
28	LIANG Jun, HUANG Yuanbiao, CAO Rong. Metal-organic frameworks and porous organic polymers for sustainable fixation of carbon dioxide into cyclic carbonates[J]. Coordination Chemistry Reviews, 2019, 378: 32-65.
29	WANG Wenjing, ZHOU Mi, YUAN Daqiang. Carbon dioxide capture in amorphous porous organic polymers[J]. Journal of Materials Chemistry A, 2017, 5(4): 1334-1347.
30	SHENG Xingfeng, GUO Hongchen, QIN Yusheng, et al. A novel metalloporphyrin-based conjugated microporous polymer for capture and conversion of CO₂[J]. RSC Advances, 2015, 5(40): 31664-31669.
31	CHEN Aibing, JU Pengpeng, ZHANG Yunzhao, et al. Highly recyclable and magnetic catalyst of a metalloporphyrin-based polymeric composite for cycloaddition of CO₂ to epoxide[J]. RSC Advances, 2016, 6(99): 96455-96466.
32	DAI Zhifeng, SUN Qi, LIU Xiaolong, et al. Metalated porous porphyrin polymers as efficient heterogeneous catalysts for cycloaddition of epoxides with CO₂ under ambient conditions[J]. Journal of Catalysis, 2016, 338: 202-209.
33	WANG Wenlong, LI Cunyao, JIN Jutao, et al. Mg-porphyrin complex doped divinylbenzene based porous organic polymers (POPs) as highly efficient heterogeneous catalysts for the conversion of CO₂ to cyclic carbonates[J]. Dalton Transactions, 2018, 47(37): 13135-13141.
34	WANG Shaolei, SONG Kun peng, ZHANG Chengxin, et al. A novel metalporphyrin-based microporous organic polymer with high CO₂ uptake and efficient chemical conversion of CO₂ under ambient conditions[J]. Journal of Materials Chemistry A, 2017, 5(4): 1509-1515.
35	CHEN Yaju, LUO Rongchang, XU Qihang, et al. State-of-the-art aluminum porphyrin-based heterogeneous catalyst for the chemical fixation of CO₂ into cyclic carbonates at ambient conditions[J]. ChemCatChem, 2017, 9(5): 767-773.
36	KIM Myung Hyun, SONG Taemoon, Ue Ryung SEO, et al. Hollow and microporous catalysts bearing Cr(Ⅲ)-F porphyrins for room temperature CO₂ fixation to cyclic carbonates[J]. Journal of Materials Chemistry A, 2017, 5(45): 23612-23619.
37	XIE Yong, WANG Tingting, LIU Xiaohuan, et al. Capture and conversion of CO₂ at ambient conditions by a conjugated microporous polymer[J]. Nature Communications, 2013, 4: 1960-1966.
38	XIE Yong, YANG Ruixia, HUANG Nianyu, et al. Efficient fixation of CO₂ at mild conditions by a Cr-conjugated microporous polymer[J]. Journal of Energy Chemistry, 2014, 23(1): 22-28.
39	XIE Yong, WANG Tingting, YANG Ruixia, et al. Efficient fixation of CO₂ by a zinc-coordinated conjugated microporous polymer[J]. ChemSusChem, 2014, 7(8): 2110-2114.
40	CHUN Jiseul, KANG Sungah, KANG Narae, et al. Microporous organic networks bearing metal-salen species for mild CO₂ fixation to cyclic carbonates[J]. Journal of Materials Chemistry A, 2013, 1(18): 5517-5523.
41	ALKORDI Mohamed H, WESELINSKI Łukasz J, Valerio D'ELIA, et al. CO₂ conversion: the potential of porous-organic polymers (POPs) for catalytic CO₂-epoxide insertion[J]. Journal of Materials Chemistry A, 2016, 4(19): 7453-7460.
42	BHUNIA Subhajit, MOLLA Rostam Ali, KUMARI Vandana, et al. Zn(Ⅱ) assisted synthesis of porous salen as an efficient heterogeneous scaffold for capture and conversion of CO₂[J]. Chemical Communications, 2015, 51(86): 15732-15735.
43	LI He, LI Chun Zhi, CHEN Jian, et al. Synthesis of pyridine-zinc-based porous organic polymer for cocatalyst-free cycloaddition of epoxides[J]. Chemistry： an Asian Journal, 2017, 12(10): 1095-1103.
44	DAI Zhifeng, SUN Qi, LIU Xiaolong, et al. A hierarchical bipyridine-constructed framework for highly efficient CO₂ capture and catalytic conversion[J]. ChemSusChem, 2017, 10(6): 1186–1192.
45	Hyun Chul CHO, LEE Han Sol, CHUN Jiseul, et al. Tubular microporous organic networks bearing imidazolium salts and their catalytic CO₂ conversion to cyclic carbonates[J]. Chemical Communications, 2011, 47(3): 917-919.
46	WANG Jinquan, Waihong SNG, YI Guangshun, et al. Imidazolium salt-modified porous hypercrosslinked polymers for synergistic CO₂ capture and conversion[J]. Chemical Communications, 2015, 51(60): 12076-12079.
47	LI Jing, JIA Degong, GUO Zengjing, et al. Imidazolinium based porous hypercrosslinked ionic polymers for efficient CO₂ capture and fixation with epoxides[J]. Green Chemistry, 2017, 19(11): 2675-2686.
48	SANG Yafei, HUANG Jianhan. Benzimidazole-based hyper-cross-linked poly(ionic liquid)s for efficient CO₂ capture and conversion[J]. Chemical Engineering Journal, 2020, 385: 123973.
49	DANI Alessandro, GROPPO Elena, BAROLO Claudia, et al. Design of high surface area poly(ionic liquid)s to convert carbon dioxide into ethylene carbonate[J]. Journal of Materials Chemistry A, 2015, 3(16): 8508-8518.
50	WANG Xiaochen, ZHOU Yu, GUO Zengjing, et al. Heterogeneous conversion of CO₂ into cyclic carbonates at ambient pressure catalyzed by ionothermal-derived meso-macroporous hierarchical poly(ionic liquid)s[J]. Chemical Science, 2015, 6(12): 6916-6924.
51	CUI Caiyan, Rongjian SA, HONG Zixiao, et al. Ionic-liquid-modified click-based porous organic polymers for controlling capture and catalytic conversion of CO₂[J]. ChemSusChem, 2020, 13(1): 180-187.
52	SONG Hongbing, WANG Yongjie, XIAO Meng, et al. Design of novel poly(ionic liquids) for the conversion of CO₂ to cyclic carbonates under mild conditions without solvent[J]. ACS Sustainable Chemistry & Engineering, 2019, 7(10): 9489-9497.
53	ZHANG Qiang, ZHANG Suobo, LI Shenghai. Novel functional organic network containing quaternary phosphonium and tertiary phosphorus[J]. Macromolecules, 2012, 45(7): 2981-2988.
54	WANG Jinquan, YANG Jason Gan Wei, YI Guangshun, et al. Phosphonium salt incorporated hypercrosslinked porous polymer for CO₂ capture and conversion[J]. Chemical Communications, 2015, 51(86): 15708-15711.
55	SUN Qi, JIN Yingyin, AGUILA Briana, et al. Porous ionic polymers as a robust and efficient platform for capture and chemical fixation of atmospheric CO₂[J]. ChemSusChem, 2016, 10(6): 1160-1165.
56	CAI Sheng, ZHU Dongliang, ZOU Yan, et al. Porous polymers bearing functional quaternary ammonium salts as efficient solid catalysts for the fixation of CO₂ into cyclic carbonates[J]. Nanoscale Research Letters, 2016, 11(1): 1-9.
57	XIE Yaqiang, SUN Qing, FU Yawen, et al. Sponge-like quaternary ammonium-based poly(ionic liquid)s for high CO₂ capture and efficient cycloaddition under mild conditions[J]. Journal of Materials Chemistry A, 2017, 5(48): 25594-25600.
58	BUYUKCAKIR Onur, Sang Hyun JE, CHOI Dong Shin, et al. Porous cationic polymers: the impact of counteranions and charges on CO₂ capture and conversion[J]. Chemical Communications, 2016, 52(5): 934-937.
59	LENG Yan, LU Dan, JIANG Pingping, et al. Highly cross-linked cationic polymer microspheres as an efficient catalyst for facile CO₂ fixation[J]. Catalysis Communications, 2016, 74: 99-103.
60	BUYUKCAKIR Onur, Sang Hyun JE, TALAPANENI Siddulu Naidu, et al. Charged covalent triazine frameworks for CO₂ capture and conversion[J]. ACS Applied Materials & Interfaces, 2017, 9(8): 7209-7216.
61	ROESER Jérôme, KAILASAM Kamalakannan, THOMAS Arne. Covalent triazine frameworks as heterogeneous catalysts for the synthesis of cyclic and linear carbonates from carbon dioxide and epoxides[J]. ChemSusChem, 2012, 5(9): 1793-1799.
62	TALAPANENI Siddulu Naidu, BUYUKCAKIR Onur, Sang Hyun JE, et al. Nanoporous polymers incorporating sterically confined N-heterocyclic carbenes for simultaneous CO₂ capture and xconversion at ambient pressure[J]. Chemistry of Materials, 2015, 27(19): 6818-6826.
63	ZHANG Xiao, Yanzong LYU, LIU Xiaoliang, et al. A hydroxyl-functionalized microporous organic polymer for capture and catalytic conversion of CO₂[J]. RSC Advances, 2016, 6(80): 76957-76963.
64	DING Meili, JIANG Hailong. One-step assembly of a hierarchically porous phenolic resin-type polymer with high stability for CO₂ capture and conversion[J]. Chemical Communications, 2016, 52(83): 12294-12297.
65	ZHANG Nan, ZOU Bo, YANG Guoping, et al. Melamine-based mesoporous organic polymers as metal-free heterogeneous catalyst: effect of hydroxyl on CO₂ capture and conversion[J]. Journal of CO₂ Utilization, 2017, 22: 9-14.
66	MENG Xianyu, LIU Yuchuan, WANG Shun, et al. Silsesquioxane-carbazole-corbelled hybrid porous polymers with flexible nanopores for efficient CO₂ conversion and luminescence sensing[J]. ACS Applied Polymer Materials, 2020, 2(2): 189-197.
67	HUI Wei, HE Xuemei, XU Xinyi, et al. Highly efficient cycloaddition of diluted and waste CO₂ into cyclic carbonates catalyzed by porous ionic copolymers[J]. Journal of CO₂ Utilization, 2020, 36: 169-176.
68	CHEN Yaju, LUO Rongchang, XU Qihang, et al. Charged metalloporphyrin polymers for cooperative synthesis of cyclic carbonates from CO₂ under ambient conditions[J]. ChemSusChem, 2017, 10(11): 2534-2541.
69	CHEN Yaju, LUO Rongchang, XU Qihang, et al. Metalloporphyrin polymers with intercalated ionic liquids for synergistic CO₂ fixation via cyclic carbonate production[J]. ACS Sustainable Chemistry & Engineering, 2018, 6(1): 1074-1082.
70	WANG Wenlong, WANG Yuqing, LI Cunyao, et al. State-of-the-art multifunctional heterogeneous POP catalyst for cooperative transformation of CO₂ to cyclic carbonates[J]. ACS Sustainable Chemistry & Engineering, 2017, 5(6): 4523-4528.
71	JAYAKUMAR Sanjeevi, LI He, CHEN Jian, et al. Cationic Zn-porphyrin polymer coated onto CNTs as a cooperative catalyst for the synthesis of cyclic carbonates[J]. ACS Applied Materials & Interfaces, 2018, 10(3): 2546-2555.
72	LENG Yan, LU Dan, ZHANG Chenjun, et al. Ionic polymer microspheres bearing a Co^Ⅲ-salen moiety as a bifunctional heterogeneous catalyst for the efficient cycloaddition of CO₂ and epoxides[J]. Chemistry: a European Journal, 2016, 22(24): 8368-8375.
73	LIU Taotao, LIANG Jun, HUANG Yuanbiao, et al. A bifunctional cationic porous organic polymer based on a Salen-(Al) metalloligand for the cycloaddition of carbon dioxide to produce cyclic carbonates[J]. Chemical Communications, 2016, 52(90): 13288-13291.
74	LUO Rongchang, CHEN Yaju, HE Qian, et al. Metallosalen-based ionic porous polymers as bifunctional catalysts for the conversion of CO₂ into valuable chemicals[J]. ChemSusChem, 2017, 10(7): 1526-1533.
75	LI Jing, HAN Yulan, JI Tuo, et al. Porous metallosalen hypercrosslinked ionic polymers for cooperative CO₂ cycloaddition conversion[J]. Industrial & Engineering Chemistry Research, 2019, 59(2): 676-684.
76	WANG Wenlong, LI Cunyao, YAN Li, et al. Ionic liquid/Zn-PPh₃ integrated porous organic polymers featuring multifunctional sites: highly active heterogeneous catalyst for cooperative conversion of CO₂ to cyclic carbonates[J]. ACS Catalysis, 2016, 6(9): 6091-6100.
77	LI Cunyao, WANG Wenlong, YAN Li, et al. Phosphonium salt and ZnX₂-PPh₃integrated hierarchical POPs: tailorable synthesis and highly efficient cooperative catalysis in CO₂utilization[J]. Journal of Materials Chemistry A, 2016, 4(41): 16017-16027.
78	BOBBINK Felix D, VAN MUYDEN Antoine P, Aswin Gopakumar, et al. Synthesis of cross-linked Iionic poly(styrenes) and their application as catalysts for the synthesis of carbonates from CO₂ and epoxides[J]. ChemPlusChem, 2017, 82(1): 144-151.
79	JAYAKUMAR Sanjeevi, LI He, ZHAO Yaopeng, et al. Cocatalyst-free hybrid ionic liquid (IL)-based porous materials for efficient synthesis of cyclic carbonates through a cooperative activation pathway[J]. Chemistry: an Asian Journal, 2017, 12(5): 577-585.
80	LIU Ying, CHENG Weiguo, ZHANG Yanqiang, et al. Controllable preparation of phosphonium-based polymeric ionic liquids as highly selective nanocatalysts for the chemical conversion of CO₂ with epoxides[J]. Green Chemistry, 2017, 19(9): 2184-2193.
81	GUO Zengjing, JIANG Qiuwei, SHI Yuming, et al. Tethering dual hydroxyls into mesoporous poly(ionic liquid)s for chemical fixation of CO₂ at ambient conditions: a combined experimental and theoretical study[J]. ACS Catalysis, 2017, 7(10): 6770-6780.
82	CHEN Yaju, LUO Rongchang, BAO Junhui, et al. Function-oriented ionic polymers having high-density active sites for sustainable carbon dioxide conversion[J]. Journal of Materials Chemistry A, 2018, 6(19): 9172-9182.
83	DONG Bin, WANG Liangying, ZHAO Shang, et al. Immobilization of ionic liquids to covalent organic frameworks for catalyzing the formylation of amines with CO₂ and phenylsilane[J]. Chemical Communications, 2016, 52(44): 7082-7085.
84	XIE Chao, SONG Jinliang, WU Haoran, et al. Natural product glycine betaine as an efficient catalyst for transformation of CO₂ with amines to synthesize N-substituted compounds[J]. ACS Sustainable Chemistry & Engneering, 2017, 5(8): 7086-7092.
85	LIU Xiaofang, LI Xiaoya, QIAO Chang, et al. Betaine catalysis for hierarchical reduction of CO₂ with amines and hydrosilane to form formamides, aminals, and methylamines[J]. Angewandte Chemie International Edition, 2017, 56(26): 7425-7429.
86	HU Kewei, TANG Yongquan, CUI Jia, et al. Location matters: cooperativity of catalytic partners in porous organic polymers for enhanced CO₂ transformation[J]. Chemical Communications, 2019, 55(62): 9180-9183.
87	GUO Zengjing, CAI Xiaochun, XIE Jingyan, et al. Hydroxyl-exchanged nanoporous ionic copolymer toward low-temperature cycloaddition of atmospheric carbon dioxide into carbonates[J]. ACS Applied Materials & Interfaces, 2016, 8(20): 12812-12821.
88	JI Guipeng, YANG Zhenzhen, ZHANG Hongye, et al. Hierarchically mesoporous o-hydroxyazobenzene polymers: synthesis and their applications in CO₂ capture and conversion[J]. Angewandte Chemie International Edition, 2016, 55(33): 9685-9689.
89	LIU Fujian, HUANG Kuan, WU Qin, et al. Solvent-free self-assembly to the synthesis of nitrogen-doped ordered mesoporous polymers for highly selective capture and conversion of CO₂[J]. Advanced Materials, 2017, 29(27): 1700445.
90	CHEN Jian, ZHONG Mingmei, TAO Lin, et al. The cooperation of porphyrin-based porous polymer and thermal-responsive ionic liquid for efficient CO₂ cycloaddition reaction[J]. Green Chemistry, 2018, 20(4): 903-911.
91	ZHANG Wei, MEI Yu, WU Peng, et al. Highly tunable periodic imidazole-based mesoporous polymers as cooperative catalysts for efficient carbon dioxide fixation[J]. Catalysis Science & Technology, 2019, 9(4): 1030-1038.
92	PUTHIARAJ Pillaiyar, RAVI Seenu, YU Kwangsun, et al. CO₂ adsorption and conversion into cyclic carbonates over a porous ZnBr₂-grafted N-heterocyclic carbene-based aromatic polymer[J]. Applied Catalysis B: Environmental, 2019, 251: 195-205.

[1]	ZHENG Qian, GUAN Xiushuai, JIN Shanbiao, ZHANG Changming, ZHANG Xiaochao. Photothermal catalysis synthesis of DMC from CO₂ and methanol over Ce_0.25Zr_0.75O₂ solid solution [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 319-327.
[2]	SUN Yuyu, CAI Xinlei, TANG Jihai, HUANG Jingjing, HUANG Yiping, LIU Jie. Optimization and energy-saving of a reactive distillation process for the synthesis of methyl methacrylate [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 56-63.
[3]	YANG Hanyue, KONG Lingzhen, CHEN Jiaqing, SUN Huan, SONG Jiakai, WANG Sicheng, KONG Biao. Decarbonization performance of downflow tubular gas-liquid contactor of microbubble-type [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 197-204.
[4]	WANG Yaogang, HAN Zishan, GAO Jiachen, WANG Xinyu, LI Siqi, YANG Quanhong, WENG Zhe. Strategies for regulating product selectivity of copper-based catalysts in electrochemical CO₂ reduction [J]. Chemical Industry and Engineering Progress, 2023, 42(8): 4043-4057.
[5]	LIU Yi, FANG Qiang, ZHONG Dazhong, ZHAO Qiang, LI Jinping. Cu facets regulation of Ag/Cu coupled catalysts for electrocatalytic reduction of carbon dioxide [J]. Chemical Industry and Engineering Progress, 2023, 42(8): 4136-4142.
[6]	HUANG Yufei, LI Ziyi, HUANG Yangqiang, JIN Bo, LUO Xiao, LIANG Zhiwu. Research progress on catalysts for photocatalytic CO₂ and CH₄ reforming [J]. Chemical Industry and Engineering Progress, 2023, 42(8): 4247-4263.
[7]	LOU Baohui, WU Xianhao, ZHANG Chi, CHEN Zhen, FENG Xiangdong. Advances in nanofluid for CO₂ absorption and separation [J]. Chemical Industry and Engineering Progress, 2023, 42(7): 3802-3815.
[8]	LYU Chao, ZHANG Xiwen, JIN Lijian, YANG Linjun. Efficient capture of CO₂ by a new biphasic solvent-ionic liquid system [J]. Chemical Industry and Engineering Progress, 2023, 42(6): 3226-3232.
[9]	YUE Xin, LI Chunying, SUN Dao’an, LI Jiangwei, DU Yongmei, MA Hui, LYU Jian. Progress on heterogeneous catalysts for cyclopropanation of diazo compounds [J]. Chemical Industry and Engineering Progress, 2023, 42(5): 2390-2401.
[10]	WANG Keju, ZHAO Cheng, HU Xiaomei, YUN Junge, WEI Ninghan, JIANG Xueying, ZOU Yun, CHEN Zhihang. Research progress of low temperature catalytic oxidation of VOCs by metal oxides [J]. Chemical Industry and Engineering Progress, 2023, 42(5): 2402-2412.
[11]	MA Yuan, XIAO Qingyue, YUE Junrong, CUI Yanbin, LIU Jiao, XU Guangwen. CO _xco-methanation over a Ni-based catalyst supported on CeO₂-Al₂O₃ composite [J]. Chemical Industry and Engineering Progress, 2023, 42(5): 2421-2428.
[12]	HE Zhiyong, GUO Tianfo, WANG Jinli, LYU Feng. Progress of CO₂/epoxide copolymerization catalyst [J]. Chemical Industry and Engineering Progress, 2023, 42(4): 1847-1859.
[13]	FU Le, YANG Yang, XU Wenqing, GENG Zanbu, ZHU Tingyu, HAO Runlong. Research progress in CO₂ capture technology using novel biphasic organic amine absorbent [J]. Chemical Industry and Engineering Progress, 2023, 42(4): 2068-2080.
[14]	CHEN Chongming, ZENG Siming, LUO Xiaona, SONG Guosheng, HAN Zhongge, YU Jinxing, SUN Nannan. Preparation and performance of carbon supported potassium-based CO₂ adsorbent derived from hyper-cross linked polymers [J]. Chemical Industry and Engineering Progress, 2023, 42(3): 1540-1550.
[15]	WANG Qiuhua, WU Jiashuai, ZHANG Weifeng. Research progress of alkaline industrial solid wastes mineralization for carbon dioxide sequestration [J]. Chemical Industry and Engineering Progress, 2023, 42(3): 1572-1582.