Research advance of heterogeneous catalytic system for the coupling between CO2 and epoxide into propylene carbonate

doi:10.16085/j.issn.1000-6613.2023-0351

Abstract

Abstract:

As the most important greenhouse gas, carbon dioxide (CO₂) has caused serious environmental problems by excessive emission. On the other hand, CO₂ is an abundant, cheap, safe and renewable C₁ resource, and thus is considered as an ideal carbon material in organic synthesis. Efficient and green chemical fixing CO₂ to prepare cyclic carbonate with high boiling, high polarity, low volatility and biological degradability is an effective way of CO₂ resource utilization, which has attracted wide attention. In this paper, the existing reaction pathways for the synthesis of cyclic carbonate are briefly described. Then, staring with the coupling reaction of CO₂ with epoxides, we emphatically analyze the reaction mechanism, and the design ideas and current research advance of the heterogeneous catalytic system. Meanwhile, the advantages and disadvantages of the catalytic parameters such as catalytic conditions, catalytic activity and recyclability, of different heterogeneous catalytic systems are comprehensively compared. Finally, the application and development prospects of different heterogeneous catalytic systems are summarized and suggested. In the future, heterogeneous catalytic systems should be combined with homogeneous ones, which could efficiently activate CO₂ and epoxides under mild conditions by utilizing their advantages.

Key words: carbon dioxide, catalyst, epoxides, catalysis, coupling reaction, cyclic carbonate

摘要：

作为最主要的温室气体，二氧化碳（CO₂）的过度排放已导致了严重的环境问题。同时，CO₂也属于储量丰富、廉价、安全和可再生利用的C₁资源，被认为是有机合成的理想碳材料。高效且绿色的化学固定CO₂耦合制备具有高沸点、高极性、低挥发性和可生物降解性等优点的环状碳酸酯是CO₂资源化利用的有效方式，已引起社会各界的广泛关注。本文首先简述了目前合成环状碳酸酯的现有反应路径。然后，以CO₂和环氧化物的耦合反应为出发点，着重分析了该反应发生所涉及的反应机理以及催化该反应时多相催化体系的设计思路和当前研究进展。同时，综合比较了不同多相催化体系的催化条件、催化活性及循环使用性等催化参数的优缺点。最后，基于上述分析，本文总结了不同多相催化体系的应用前景并建议其后续发展应与均相催化体系相结合，利用两者的优势高效活化CO₂与环氧化物，以实现温和条件下催化耦合反应。

关键词: 二氧化碳, 催化剂, 环氧化物, 催化作用, 耦合反应, 环状碳酸酯

CLC Number:

TQ203.2

LIU Fangwang, HAN Yi, ZHANG Jiajia, BU Honghong, WANG Xingpeng, YU Chuanfeng, LIU Mengshuai. Research advance of heterogeneous catalytic system for the coupling between CO₂ and epoxide into propylene carbonate[J]. Chemical Industry and Engineering Progress, 2024, 43(3): 1252-1265.

刘方旺, 韩艺, 张佳佳, 步红红, 王兴鹏, 于传峰, 刘猛帅. CO₂与环氧化物耦合制备环状碳酸酯的多相催化体系研究进展[J]. 化工进展, 2024, 43(3): 1252-1265.

Figures/Tables 16

References 108

1	WEBSTER Dean C. Cyclic carbonate functional polymers and their applications[J]. Progress in Organic Coatings, 2003, 47(1): 77-86.
2	BOBBINK Felix D, DYSON Paul J. Synthesis of carbonates and related compounds incorporating CO₂ using ionic liquid-type catalysts: State-of-the-art and beyond[J]. Journal of Catalysis, 2016, 343: 52-61.
3	SUN Jianmin, FUJITA Shin-ichiro, ARAI Masahiko. Development in the green synthesis of cyclic carbonate from carbon dioxide using ionic liquids[J]. Journal of Organometallic Chemistry, 2005, 690(15): 3490-3497.
4	YU Wei, EDWARD Maynard, VIVIANE Chiaradia, et al. Aliphatic polycarbonates from cyclic carbonate monomers and their application as biomaterials[J]. Chemical Reviews, 2021, 121(18): 10865-10907.
5	MARCINIAK Aryane A, LAMB Katie J, OZORIO Leonardo P, et al. Heterogeneous catalysts for cyclic carbonate synthesis from carbon dioxide and epoxides[J]. Current Opinion in Green and Sustainable Chemistry, 2020, 26: 100365.
6	SHI Feng, DENG Youquan, SIMA Tianlong, et al. Alternatives to phosgene and carbon monoxide: Synthesis of symmetric urea derivatives with carbon dioxide in ionic liquids[J]. Angewandte Chemie International Edition, 2003, 42(28): 3257-3260.
7	GREGORY Georgina L, ULMANN Marion, BUCHARD Antoine. Synthesis of 6-membered cyclic carbonates from 1, 3-diols and low CO₂ pressure: A novel mild strategy to replace phosgene reagents[J]. RSC Advances, 2015, 5(49): 39404-39408.
8	LIU Anhua, LI Yunong, HE Liangnian. Organic synthesis using carbon dioxide as phosgene-free carbonyl reagent[J]. Pure and Applied Chemistry, 2011, 84(3): 581-602.
9	DU Ya, HE Liangnian, KONG Delin. Magnesium-catalyzed synthesis of organic carbonate from 1,2-diol/alcohol and carbon dioxide[J]. Catalysis Communications, 2008, 9(8): 1754-1758.
10	LI Mingli, ABDOLMOHAMMADI Shahrzad, HOSEININEZHAD-NAMIN Mir S, et al. Carboxylative cyclization of propargylic alcohols with carbon dioxide: A facile and Green route to α-methylene cyclic carbonates[J]. Journal of CO₂ Utilization, 2020, 38: 220-231.
11	WANG Liang, QUE Sisi, DING Ziwei, et al. Correction: Oxidative carboxylation of olefins with CO₂: Environmentally benign access to five-membered cyclic carbonates[J]. RSC Advances, 2020, 10(18): 10806.
12	TRUONG Cong Chien, MISHRA Dinesh Kumar. Recent advances in the catalytic fixation of carbon dioxide to value-added chemicals over alkali metal salts[J]. Journal of CO₂ Utilization, 2020, 41: 101252.
13	LIU Fusheng, GU Yongqiang, XIN Hao, et al. Multifunctional phosphonium-based deep eutectic ionic liquids: Insights into simultaneous activation of CO₂ and epoxide and their subsequent cycloaddition[J]. ACS Sustainable Chemistry & Engineering, 2019, 7(19): 16674-16681.
14	MA Jun, LIU Jinli, ZHANG Zhaofu, et al. The catalytic mechanism of KI and the co-catalytic mechanism of hydroxyl substances for cycloaddition of CO₂ with propylene oxide[J]. Green Chemistry, 2012, 14(9): 2410-2420.
15	SONG Jinliang, ZHANG Zhaofu, HAN Buxing, et al. Synthesis of cyclic carbonates from epoxides and CO₂ catalyzed by potassium halide in the presence of β-cyclodextrin[J]. Green Chemistry, 2008, 10(12): 1337.
16	ZHANG Yuanyuan, YIN Shuangfeng, LUO Shenglian, et al. Cycloaddition of CO₂ to epoxides catalyzed by carboxyl-functionalized imidazolium-based ionic liquid grafted onto cross-linked polymer[J]. Industrial & Engineering Chemistry Research, 2012, 51(10): 3951-3957.
17	SUN Jian, WANG Jinquan, CHENG Weiguo, et al. Chitosan functionalized ionic liquid as a recyclable biopolymer-supported catalyst for cycloaddition of CO₂ [J]. Green Chemistry, 2012, 14(3): 654-660.
18	SUN Jian, CHENG Weiguo, FAN Wei, et al. Reusable and efficient polymer-supported task-specific ionic liquid catalyst for cycloaddition of epoxide with CO₂ [J]. Catalysis Today, 2009, 148(3/4): 361-367.
19	ZHAO Yuqing, LIU Yingying, MA Jianfang. Polyoxometalate-based organic-inorganic hybrids as heterogeneous catalysts for cycloaddition of CO₂ with epoxides and oxidative desulfurization reactions[J]. Crystal Growth & Design, 2021, 21(2): 1019-1027.
20	GE Weilin, WANG Xiaochen, ZHANG Lingyu, et al. Fully-occupied Keggin type polyoxometalate as solid base for catalyzing CO₂ cycloaddition and Knoevenagel condensation[J]. Catalysis Science & Technology, 2016, 6(2): 460-467.
21	FERNANDES Diana M, PEIXOTO Andreia F, FREIRE Cristina. Nitrogen-doped metal-free carbon catalysts for (electro)chemical CO₂ conversion and valorisation[J]. Dalton Transactions, 2019, 48(36): 13508-13528.
22	MA Xiaoyu, ZOU Bo, CAO Minhua, et al. Nitrogen-doped porous carbon monolith as a highly efficient catalyst for CO₂ conversion[J]. Journal of Materials Chemistry A, 2014, 2(43): 18360-18366.
23	WANG X, HUI W, HU A, et al. A synthesis of porous activated carbon materials derived from vitamin B9 base for CO₂ capture and conversion[J]. Materials Today Chemistry, 2021, 20: 100468.
24	AN Qiao, LI Zifeng, GRAFF Robert, et al. Core-double-shell Fe₃O₄@Carbon@Poly(InⅢ-carboxylate) microspheres: Cycloaddition of CO₂ and epoxides on coordination polymer shells constituted by imidazolium-derived AlⅢ-salen bifunctional catalysts[J]. ACS Applied Materials & Interfaces, 2015, 7(8): 4969-4978.
25	MIN Jie, SONG Wei, HU Tianding, et al. Fe₃O₄@SiO₂ nanoparticle-supported Co(Ⅲ)-Salen composites as recyclable heterogeneous catalyst for the fixation of CO₂ [J]. Ceramics International, 2021, 47(24): 35320-35332.
26	Fernando CASTRO-GÓMEZ, SALASSA Giovanni, KLEIJ Arjan W, et al. A DFT study on the mechanism of the cycloaddition reaction of CO₂ to epoxides catalyzed by Zn(salphen) complexes[J]. Chemistry-A European Journal, 2013, 19(20): 6289-6298.
27	ZHANG Chenjun, LU Dan, LENG Yan, et al. Metal-salen-bridged ionic networks as efficient bifunctional solid catalysts for chemical fixation of CO₂ into cyclic carbonates[J]. Molecular Catalysis, 2017, 439: 193-199.
28	梁均. 阳离子型金属-有机框架的设计、制备及对CO₂的催化转化性能研究[D]. 厦门: 厦门大学, 2018.
	LIANG Jun. Design and preparation of cationic metal-organic framework and its catalytic conversion performance for CO₂ [D]. Xiamen: Xiamen University, 2018.
29	Jinmi NOH, KIM Youngik, PARK Hyojin, et al. Functional group effects on a metal-organic framework catalyst for CO₂ cycloaddition[J]. Journal of Industrial and Engineering Chemistry, 2018, 64: 478-483.
30	DING Luogang, YAO Bingjian, JIANG Weiling, et al. Bifunctional imidazolium-based ionic liquid decorated UiO-67 type MOF for selective CO₂ adsorption and catalytic property for CO₂ cycloaddition with epoxides[J]. Inorganic Chemistry, 2017, 56(4): 2337-2344.
31	MOUSAVI Bibimaryam, CHAEMCHUEN Somboon, MOOSAVI Behrooz, et al. CO₂ cycloaddition to epoxides by using M-DABCO metal-organic frameworks and the influence of the synthetic method on catalytic reactivity[J]. ChemistryOpen, 2017, 6(5): 674-680.
32	SENGUPTA Manideepa, Arijit BAG, GHOSH Swarbhanu, et al. Cu _x O _y @COF: An efficient heterogeneous catalyst system for CO₂ cycloadditions under ambient conditions[J]. Journal of CO₂ Utilization, 2019, 34: 533-542.
33	ZHAO Yuling, ZHAO Yue, QIU Jikuan, et al. Facile grafting of imidazolium salt in covalent organic frameworks with enhanced catalytic activity for CO₂ fixation and the Knoevenagel reaction[J]. ACS Sustainable Chemistry & Engineering, 2020, 8(50): 18413-18419.
34	GUGLIELMERO Luca, MEZZETTA Andrea, POMELLI Christian Silvio, et al. Evaluation of the effect of the dicationic ionic liquid structure on the cycloaddition of CO₂ to epoxides[J]. Journal of CO₂ Utilization, 2019, 34: 437-445.
35	LIU Fang, HU Yuhang, ZHOU Jingsheng, et al. “Responsive” ionic liquids to catalyze the transformation of carbon dioxide under atmospheric pressure[J]. Applied Catalysis A: General, 2021, 623: 118241.
36	SHANG Yuhan, GONG Qing, ZHENG Mai, et al. An efficient morpholinium ionic liquid based catalyst system for cycloaddition of CO₂ and epoxides under mild conditions[J]. Journal of Molecular Liquids, 2019, 283: 235-241.
37	MENG Xianglei, JU Zhaoyang, ZHANG Suojiang, et al. Efficient transformation of CO₂ to cyclic carbonates using bifunctional protic ionic liquids under mild conditions[J]. Green Chemistry, 2019, 21(12): 3456-3463.
38	SHI Guiling, ZHAI Ran, LI Haoran, et al. Highly efficient synthesis of alkylidene cyclic carbonates from low concentration CO₂ using hydroxyl and azolate dual functionalized ionic liquids[J]. Green Chemistry, 2021, 23(1): 592-596.
39	HUI Wei, WANG Xiang, LI Xiaoning, et al. Protic ionic liquids tailored by different cationic structures for efficient chemical fixation of diluted and waste CO₂ into cyclic carbonates[J]. New Journal of Chemistry, 2021, 45(24): 10741-10748.
40	LIU Ying, CAO Zhi, ZHOU Zheng, et al. Imidazolium-based deep eutectic solvents as multifunctional catalysts for multisite synergistic activation of epoxides and ambient synthesis of cyclic carbonates[J]. Journal of CO₂ Utilization, 2021, 53: 101717.
41	LIU Fusheng, GU Yongqiang, ZHAO Penghui, et al. N-hydroxysuccinimide based deep eutectic catalysts as a promising platform for conversion of CO₂ into cyclic carbonates at ambient temperature[J]. Journal of CO₂ Utilization, 2019, 33: 419-426.
42	HE Liang, ZHANG Wenwen, YANG Yufan, et al. Novel biomass-derived deep eutectic solvents promoted cycloaddition of CO₂ with epoxides under mild and additive-free conditions[J]. Journal of CO₂ Utilization, 2021, 54: 101750.
43	TAN Liangxiao, TAN Bien. Hypercrosslinked porous polymer materials: Design, synthesis, and applications[J]. Chemical Society Reviews, 2017, 46(11): 3322-3356.
44	WANG Jinyuan, LIANG Yatao, ZHOU Dagang, et al. New crown ether complex cation ionic liquids with N-heterocycle anions: Preparation and application in CO₂ fixation[J]. Organic Chemistry Frontiers, 2018, 5(5): 741-748.
45	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.
46	HU Tianding, SUN Yuwang, DING Yihong. A quantum-chemical insight on chemical fixation carbon dioxide with epoxides co-catalyzed by MIL-101 and tetrabutylammonium bromide[J]. Journal of CO₂ Utilization, 2018, 28: 200-206.
47	GAO Xiangxiang, LIU Mengshuai, LAN Jianwen, et al. Lewis acid-base bifunctional crystals with a three-dimensional framework for selective coupling of CO₂ and epoxides under mild and solvent-free conditions[J]. Crystal Growth & Design, 2017, 17(1): 51-57.
48	WANG Tingting, XIE Yong, DENG Weiqiao. Reaction mechanism of epoxide cycloaddition to CO₂ catalyzed by salen-M (M=Co, Al, Zn)[J]. The Journal of Physical Chemistry A, 2014, 118(39): 9239-9243.
49	SONG Chengling, LING Yajing, JIN Liting, et al. CO₂ adsorption of three isostructural metal-organic frameworks depending on the incorporated highly polarized heterocyclic moieties[J]. Dalton Transactions, 2016, 45(1): 190-197.
50	HE Jinling, WU Tianbin, ZHANG Zhaofu, et al. Cycloaddition of CO₂ to epoxides catalyzed by polyaniline salts[J]. Chemistry-A European Journal, 2007, 13(24): 6992-6997.
51	Chee Koon NG, Ren Wei TOH, LIN Ting ting, et al. Metal-salen molecular cages as efficient and recyclable heterogeneous catalysts for cycloaddition of CO₂ with epoxides under ambient conditions[J]. Chemical Science, 2019, 10(5): 1549-1554.
52	Saeideh GHAZALI-ESFAHANI, SONG Hongbing, Emilia PÄƒUNESCU, et al. Cycloaddition of CO₂ to epoxides catalyzed by imidazolium-based polymeric ionic liquids[J]. Green Chemistry, 2013, 15(6): 1584-1589.
53	UDAYAKUMAR Seshachalam, LEE Mi-Kyung, SHIM Hye-Lim, et al. Imidazolium derivatives functionalized MCM-41 for catalytic conversion of carbon dioxide to cyclic carbonate[J]. Catalysis Communications, 2009, 10(5): 659-664.
54	CHENG Weiguo, CHEN Xi, SUN Jian, et al. SBA-15 supported triazolium-based ionic liquids as highly efficient and recyclable catalysts for fixation of CO₂ with epoxides[J]. Catalysis Today, 2013, 200: 117-124.
55	ZUCCA Paolo, SANJUST Enrico. Inorganic materials as supports for covalent enzyme immobilization: Methods and mechanisms[J]. Molecules, 2014, 19(9): 14139-14194.
56	HAN Lina, CHOI Hye-Ji, KIM Dong-Kyu, et al. Porous polymer bead-supported ionic liquids for the synthesis of cyclic carbonate from CO₂ and epoxide[J]. Journal of Molecular Catalysis A: Chemical, 2011, 338(1/2): 58-64.
57	MOTOKURA Ken, ITAGAKI Shintaro, IWASAWA Yasuhiro, et al. Silica-supported aminopyridinium halides for catalytic transformations of epoxides to cyclic carbonates under atmospheric pressure of carbon dioxide[J]. Green Chemistry, 2009, 11(11): 1876-1880.
58	XIE Haibo, DUAN Haifeng, LI Shenghai, et al. The effective synthesis of propylene carbonate catalyzed by silica-supported hexaalkylguanidinium chloride[J]. New Journal of Chemistry, 2005, 29(9): 1199-1203.
59	WANG Jinquan, KONG Delin, CHEN Jianyu, et al. Synthesis of cyclic carbonates from epoxides and carbon dioxide over silica-supported quaternary ammonium salts under supercritical conditions[J]. Journal of Molecular Catalysis A: Chemical, 2006, 249(1/2): 143-148.
60	DU Ya, WANG Jinquan, CHEN Jianyu, et al. A poly(ethylene glycol)-supported quaternary ammonium salt for highly efficient and environmentally friendly chemical fixation of CO₂ with epoxides under supercritical conditions[J]. Tetrahedron Letters, 2006, 47(8): 1271-1275.
61	ZHAO Yuan, TIAN Jiesheng, QI Xinhua, 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: Chemical, 2007, 271(1/2): 284-289.
62	CHEN Xi, SUN Jian, WANG Jinquan, et al. Polystyrene-bound diethanolamine based ionic liquids for chemical fixation of CO₂ [J]. Tetrahedron Letters, 2012, 53(22): 2684-2688.
63	THARUN Jose, KIM Dong Woo, ROSHAN Roshith, et al. Microwave assisted preparation of quaternized chitosan catalyst for the cycloaddition of CO₂ and epoxides[J]. Catalysis Communications, 2013, 31: 62-65.
64	KIM Doyun, SUBRAMANIAN Saravanan, THIRION Damien, et al. Quaternary ammonium salt grafted nanoporous covalent organic polymer for atmospheric CO₂ fixation and cyclic carbonate formation[J]. Catalysis Today, 2020, 356: 527-534.
65	LIU Mengshuai, WANG Xin, JIANG Yichen, et al. Hydrogen bond activation strategy for cyclic carbonates synthesis from epoxides and CO₂: Current state-of-the art of catalyst development and reaction analysis[J]. Catalysis Reviews, 2019, 61(2): 214-269.
66	GOU Haibin, MA Xifei, SU Qian, et al. Hydrogen bond donor functionalized poly(ionic liquid)s for efficient synergistic conversion of CO₂ to cyclic carbonates[J]. Physical Chemistry Chemical Physics, 2021, 23(3): 2005-2014.
67	WAN Yali, ZHANG Zemin, DING Chao, et al. Facile construction of bifunctional porous ionic polymers for efficient and metal-free catalytic conversion of CO₂ into cyclic carbonates[J]. Journal of CO₂ Utilization, 2021, 52: 101673.
68	ZHANG Feng, WANG Yanyan, ZHANG Xiaochun, et al. Recent advances in the coupling of CO₂ and epoxides into cyclic carbonates under halogen-free condition[J]. Green Chemical Engineering, 2020, 1(2): 82-93.
69	Tapan K PAL, DE Dinesh, BHARADWAJ Parimal K. Metal-organic frameworks for the chemical fixation of CO₂ into cyclic carbonates[J]. Coordination Chemistry Reviews, 2020, 408: 213173.
70	SONG Jinliang, ZHANG Zhaofu, HU Suqin, et al. MOF-5/n-Bu₄NBr: An efficient catalyst system for the synthesis of cyclic carbonates from epoxides and CO₂ under mild conditions[J]. Green Chemistry, 2009, 11(7): 1031-1036.
71	ZALOMAEVA Olga V, MAKSIMCHUK Nataliya V, CHIBIRYAEV Andrey 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.
72	MIRALDA Carmen M, MACIAS Eugenia E, ZHU Minqi, et al. Zeolitic imidazole framework-8 catalysts in the conversion of CO₂ to chloropropene carbonate[J]. ACS Catalysis, 2012, 2(1): 180-183.
73	XU Wei, CHEN Hao, Kecheng JIE, et al. Entropy-driven mechanochemical synthesis of polymetallic zeolitic imidazolate frameworks for CO₂ fixation[J]. Angewandte Chemie International Edition, 2019, 58(15): 5018-5022.
74	ZHU Minqi, SRINIVAS Darbha, BHOGESWARARAO Seemala, et al. Catalytic activity of ZIF-8 in the synthesis of styrene carbonate from CO₂ and styrene oxide[J]. Catalysis Communications, 2013, 32: 36-40.
75	YANG Lili, YU Lin, DIAO Guiqiang, et al. Zeolitic imidazolate framework-68 as an efficient heterogeneous catalyst for chemical fixation of carbon dioxide[J]. Journal of Molecular Catalysis A: Chemical, 2014, 392: 278-283.
76	JOSE Tharun, HWANG Yeseul, KIM Dong-Woo, et al. Functionalized zeolitic imidazolate framework F-ZIF-90 as efficient catalyst for the cycloaddition of carbon dioxide to allyl glycidyl ether[J]. Catalysis Today, 2015, 245: 61-67.
77	THARUN Jose, MATHAI George, KATHALIKKATTIL Amal Cherian, et al. Exploring the catalytic potential of ZIF-90: Solventless and co-catalyst-free synthesis of propylene carbonate from propylene oxide and CO₂ [J]. ChemPlusChem, 2015, 80(4): 715-721.
78	KATHALIKKATTIL Amal Cherian, ROSHAN Roshith, THARUN Jose, et al. Pillared cobalt-amino acid framework catalysis for styrene carbonate synthesis from CO₂ and epoxide by metal-sulfonate-halide synergism[J]. ChemCatChem, 2014, 6(1): 284-292.
79	FENG Dawei, CHUNG Wan-Chun, WEI Zhangwen, et al. Construction of ultrastable porphyrin Zr metal-organic frameworks through linker elimination[J]. Journal of the American Chemical Society, 2013, 135(45): 17105-17110.
80	CHO Hye-Young, YANG Da-Ae, KIM Jun, et al. CO₂ adsorption and catalytic application of Co-MOF-74 synthesized by microwave heating[J]. Catalysis Today, 2012, 185(1): 35-40.
81	KIM Yu-Jin, PARK Dae-Won. Functionalized IRMOF-3: An efficient heterogeneous catalyst for the cycloaddition of allyl glycidyl ether and CO₂ [J]. Journal of Nanoscience and Nanotechnology, 2013, 13(3): 2307-2312.
82	ZALOMAEVA Olga V, CHIBIRYAEV Andrey M, KOVALENKO Konstantin A, et al. Cyclic carbonates synthesis from epoxides and CO₂ over metal-organic framework Cr-MIL-101[J]. Journal of Catalysis, 2013, 298: 179-185.
83	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.
84	KIM Hyunuk, MOON Hyun-Sik, SOHAIL Muhammad, et al. Synthesis of cyclic carbonate by CO₂ fixation to epoxides using interpenetrated MOF-5/n-Bu₄NBr[J]. Journal of Materials Science, 2019, 54(18): 11796-11803.
85	Patel Parth, Parmar Bhavesh, KURESHY Rukhsana I, et al. Amine-functionalized Zn(Ⅱ) MOF as an efficient multifunctional catalyst for CO₂ utilization and sulfoxidation reaction[J]. Dalton Transactions, 2018, 47(24): 8041-8051.
86	GUPTA Mayank, DE Dinesh, TOMAR Kapil, et al. From Zn(Ⅱ)-carboxylate to double-walled Zn(Ⅱ)-carboxylato phosphate MOF: Change in the framework topology, capture and conversion of CO₂, and catalysis of strecker reaction[J]. Inorganic Chemistry, 2017, 56(23): 14605-14611.
87	VERMA Ashish, DE Dinesh, TOMAR Kapil, et al. An amine functionalized metal-organic framework as an effective catalyst for conversion of CO₂ and biginelli reactions[J]. Inorganic Chemistry, 2017, 56(16): 9765-9771.
88	HE Hongming, SUN Qi, GAO Wenyang, et al. A stable metal–organic framework featuring a local buffer environment for carbon dioxide fixation[J]. Angewandte Chemie International Edition, 2018, 57(17): 4657-4662.
89	KIM Jun, KIM Se-Na, JANG Hoi-Gu, et al. CO₂ cycloaddition of styrene oxide over MOF catalysts[J]. Applied Catalysis A: General, 2013, 453: 175-180.
90	LESCOUET Tristan, CHIZALLET Céline, FARRUSSENG David. The origin of the activity of amine-functionalized metal-organic frameworks in the catalytic synthesis of cyclic carbonates from epoxide and CO₂ [J]. ChemCatChem, 2012, 4(11): 1725-1728.
91	BAHADORI Mehrnaz, TANGESTANINEJAD Shahram, BERTMER Marko, et al. Task-specific ionic liquid functionalized-MIL-101(Cr) as a heterogeneous and efficient catalyst for the cycloaddition of CO₂ with epoxides under solvent free conditions[J]. ACS Sustainable Chemistry & Engineering, 2019, 7(4): 3962-3973.
92	MARANDI Afsaneh, BAHADORI Mehrnaz, TANGESTANINEJAD Shahram, et al. Cycloaddition of CO₂ with epoxides and esterification reactions using the porous redox catalyst Co-POM@MIL-101(Cr)[J]. New Journal of Chemistry, 2019, 43(39): 15585-15595.
93	AKIMANA Emmanuelia, WANG Jichao, LIKHANOVA Natalya V, et al. MIL-101(Cr) for CO₂ conversion into cyclic carbonates, under solvent and co-catalyst free mild reaction conditions[J]. Catalysts, 2020, 10(4): 453.
94	TAHERIMEHR Masoumeh, Ben VAN DE VOORDE, Lik H WEE, et al. Strategies for enhancing the catalytic performance of metal-organic frameworks in the fixation of CO₂ into cyclic carbonates[J]. ChemSusChem, 2017, 10(6): 1283-1291.
95	ZHOU Zhen, HE Cheng, XIU Jinghai, et al. Metal-organic polymers containing discrete single-walled nanotube as a heterogeneous catalyst for the cycloaddition of carbon dioxide to epoxides[J]. Journal of the American Chemical Society, 2015, 137(48): 15066-15069.
96	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.
97	SUN Qi, DAI Zhifeng, MENG Xiangju, et al. Porous polymer catalysts with hierarchical structures[J]. Chemical Society Reviews, 2015, 44(17): 6018-6034.
98	Søren KRAMER, BENNEDSEN Niklas R, Søren KEGNÆS. Porous organic polymers containing active metal centers as catalysts for synthetic organic chemistry[J]. ACS Catalysis, 2018, 8(8): 6961-6982.
99	LU Weigang, YUAN Daqiang, SCULLEY Julian, et al. Sulfonate-grafted porous polymer networks for preferential CO₂ adsorption at low pressure[J]. Journal of the American Chemical Society, 2011, 133(45): 18126-18129.
100	KIM Kahee, KIM Sungyoon, TALAPANENI Siddulu N, et al. Transition metal complex directed synthesis of porous cationic polymers for efficient CO₂ capture and conversion[J]. Polymer, 2017, 126: 296-302.
101	LU Weigang, SCULLEY Julian P, YUAN Daqiang, et al. Polyamine-tethered porous polymer networks for carbon dioxide capture from flue gas[J]. Angewandte Chemie International Edition, 2012, 51(30): 7480-7484.
102	LI He, FENG Xiao, SHAO Pengpeng, et al. Synthesis of covalent organic frameworks via in situ salen skeleton formation for catalytic applications[J]. Journal of Materials Chemistry A, 2019, 7(10): 5482-5492.
103	LIU Manying, GUO Liping, JIN Shangbin, et al. Covalent triazine frameworks: Synthesis and applications[J]. Journal of Materials Chemistry A, 2019, 7(10): 5153-5172.
104	GENG Tongmou, CHEN Guofeng, ZHANG Can, et al. A superacid-catalyzed synthesis of fluorescent covalent triazine based framework containing perylene tetraanhydride bisimide for sensing to O-nitrophenol with ultrahigh sensitivity[J]. Journal of Macromolecular Science A, 2019, 56(11): 1004-1011.
105	YU Soo-Young, MAHMOOD Javeed, Hyuk-Jun NOH, et al. Direct synthesis of a covalent triazine-based framework from aromatic amides[J]. Angewandte Chemie International Edition, 2018, 57(28): 8438-8442.
106	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.
107	LI Yimeng, YANG Li, SUN Lei, et al. Chemical fixation of carbon dioxide catalyzed via covalent triazine frameworks as metal free heterogeneous catalysts without a cocatalyst[J]. Journal of Materials Chemistry A, 2019, 7(45): 26071-26076.
108	YU Wenguang, GU Shuai, FU Yu, et al. Carbazole-decorated covalent triazine frameworks: Novel nonmetal catalysts for carbon dioxide fixation and oxygen reduction reaction[J]. Journal of Catalysis, 2018, 362: 1-9.

底物	催化剂名称	反应条件	收率/%	选择性/%	循环性	参考文献
AGE^①	固载化的离子液体PVIm2-BuBr	90℃；0.86MPa；6h	48.0	49	循环五次，仅第四次后略有降低	[56]
		100℃；0.86MPa；6h	58.8	60
		110℃；0.86MPa；6h	64.4	65
		110℃；1.34MPa；6h	84.2	85
		110℃；1.62MPa；6h	93.1	94
		110℃；1.82MPa；6h	97.0	98

底物	催化剂名称	反应条件	收率/%	选择性/%	循环性	参考文献
AGE^①	固载化的离子液体PVIm2-BuBr	90℃；0.86MPa；6h	48.0	49	循环五次，仅第四次后略有降低	[56]
		100℃；0.86MPa；6h	58.8	60
		110℃；0.86MPa；6h	64.4	65
		110℃；1.34MPa；6h	84.2	85
		110℃；1.62MPa；6h	93.1	94
		110℃；1.82MPa；6h	97.0	98

序号	催化剂名称	载体	反应条件	收率/%	循环性/次	参考文献
1	六烷基氯化胍（摩尔分数1%）	SiO₂	120℃，4.5MPa，4h	99	5	[58]
2	季铵盐（摩尔分数1%）	SiO₂	150℃，8.0MPa，6h	97	8	[59]
3	PEG固载的季铵盐^①（摩尔分数1%）	聚苯乙烯	100℃，8.0MPa，12h	95	5	[60]
4	3-氯-2-(羟丙基)三甲基氯化铵（摩尔分数1.7%）	壳聚糖	160℃，4.0MPa，6h	88	5	[61]
5	4-吡咯烷并吡啶碘化铵	SiO₂	100℃，0.1MPa，20.5h	89	3	[57]
6	二乙醇胺基卤化铵（摩尔分数2%）	聚苯乙烯	110℃，0.1MPa，6h	96	6	[62]
7	羟丙基三甲基碘化铵（摩尔分数0.4%）	纤维素	120℃，1.2MPa，6h	88	6	[63]
8	季铵盐	Nano-POF^② （COP-114）	100℃，0.1MPa，24h	96	3	[64]

序号	催化剂名称	载体	反应条件	收率/%	循环性/次	参考文献
1	六烷基氯化胍（摩尔分数1%）	SiO₂	120℃，4.5MPa，4h	99	5	[58]
2	季铵盐（摩尔分数1%）	SiO₂	150℃，8.0MPa，6h	97	8	[59]
3	PEG固载的季铵盐^①（摩尔分数1%）	聚苯乙烯	100℃，8.0MPa，12h	95	5	[60]
4	3-氯-2-(羟丙基)三甲基氯化铵（摩尔分数1.7%）	壳聚糖	160℃，4.0MPa，6h	88	5	[61]
5	4-吡咯烷并吡啶碘化铵	SiO₂	100℃，0.1MPa，20.5h	89	3	[57]
6	二乙醇胺基卤化铵（摩尔分数2%）	聚苯乙烯	110℃，0.1MPa，6h	96	6	[62]
7	羟丙基三甲基碘化铵（摩尔分数0.4%）	纤维素	120℃，1.2MPa，6h	88	6	[63]
8	季铵盐	Nano-POF^② （COP-114）	100℃，0.1MPa，24h	96	3	[64]

催化剂名称	底物	反应条件	收率 /%	参考文献
MOF-5/TBAB	环氧丙烷（PO）	50℃，6.0MPa，4h	98	[70]
Co-MOF-74	SO	100℃，2.0MPa，4h	96	[80]
Mg-MOF-74	SO	100℃，2.0MPa，4h	94	[81]
Cr-MIL-101	SO	25℃，0.8MPa，48h	95	[82]
Fe-MIL-101	SO	25℃，0.8MPa，48h	93	[71]
MOF-505	PO	25℃，0.1MPa，48h	48	[83]
MOF-5/TBAB	PO	50℃，0.4MPa，4h	45	[84]
ZnMOF-1-NH₂	SO	80℃，0.8MPa，8h	88	[85]
Zn(Ⅱ)-MOF	SO	70℃，0.1MPa，12h	99	[86]
Zn(Ⅱ)-MOF	SO	100℃，2.0MPa，6h	99	[87]
JUC-1000	PO	25℃，0.1MPa，48h	96	[88]
HKUST-1	SO	100℃，2.0MPa，4h	48	[89]
MIL-68(In)	SO	150℃，0.8MPa，8h	39	[90]
MIL-101(Cr)-TSIL	SO	110℃，2.0MPa，6h	95	[91]
Co-POM@MIL-101(Cr)	SO	110℃，2.0MPa，6h	88	[92]
MIL-101(Cr)	PO	35℃，0.15MPa，24h	99	[93]
MIL-101(Cr)/TBAB	SO	60℃，8.0MPa，3h	99	[94]
gea-MOF-1	SO	120℃，2.0MPa，6h	85	[73]
ZIF-8	SO	100℃，0.7MPa，5h	54	[74]
ZIF-68	SO	120℃，1.0MPa，12h	93	[75]
IRMOF-3	SO	100℃，2.0MPa，4h	33	[89]
Ni-TCPE1	SO	100℃，1.0MPa，12h	99	[95]

Research advance of heterogeneous catalytic system for the coupling between CO₂ and epoxide into propylene carbonate

CO₂与环氧化物耦合制备环状碳酸酯的多相催化体系研究进展

RichHTML

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 16

References 108

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	WANG Kai, YE Dingding, ZHU Xun, YANG Yang, CHEN Rong, LIAO Qiang. Performance of electrochemical reduction of CO₂ by superaerophilic copper foam electrode with nanowires [J]. Chemical Industry and Engineering Progress, 2024, 43(3): 1232-1240.
[2]	DING Kang, HE Junqiao, CHEN Yuanjie, YANG Xiazhen, LIU Huazhang, HUO Chao. Effect of hydrochloric acid treatment on catalytic performance of Ru/Ba-MgO catalyst template cotton fiber [J]. Chemical Industry and Engineering Progress, 2024, 43(2): 962-970.
[3]	CHEN Xiaozhen, LIU Li, YANG Chengmin, ZHENG Bumei, YIN Xiaoying, SUN Jin, YAO Yunhai, DUAN Weiyu. Research progress of alumina-supported hydrodesulfurization catalyst [J]. Chemical Industry and Engineering Progress, 2024, 43(2): 948-961.
[4]	HUANG Sheng, YANG Zhenli, LI Zhenyu. Analysis of optimization path of developing China's hydrogen industry [J]. Chemical Industry and Engineering Progress, 2024, 43(2): 882-893.
[5]	WANG Darui, SUN Hongmin, WANG Yiyan, TANG Zhimou, LI Rui, FAN Xueyan, YANG Weimin. Recent progress in zeolite for efficient catalytic reaction process [J]. Chemical Industry and Engineering Progress, 2024, 43(1): 1-18.
[6]	LUO Fen, YANG Xiaoqi, DUAN Fanglin, LI Xiaojiang, WU Liang, XU Tongwen. Recent advances in the bipolar membrane and its applications [J]. Chemical Industry and Engineering Progress, 2024, 43(1): 145-163.
[7]	GAI Hongwei, ZHANG Chenjun, QU Jingying, SUN Huailu, TUO Yongxiao, WANG Bin, JIN Xu, ZHANG Xi, FENG Xiang, CHEN De. Research progress on catalytic dehydrogenation process intensification for liquid organic hydride carrier hydrogen storage [J]. Chemical Industry and Engineering Progress, 2024, 43(1): 164-185.
[8]	ZHANG Jiahao, LI Yingying, XU Yanlin, YIN Jiabin, ZHANG Jisong. Research advancement of continuous reductive amination in microreactors [J]. Chemical Industry and Engineering Progress, 2024, 43(1): 186-197.
[9]	WANG Yujie, ZHANG Yanmei, LUAN Jinyi, ZHAO Zhiping. Enzyme-catalyzed carbon sequestration processes and enhancement technologies [J]. Chemical Industry and Engineering Progress, 2024, 43(1): 232-245.
[10]	HENG Linyu, DENG Zhuoran, CHENG Daojian, WEI Bin, ZHAO Liqiang. Progress of high-throughput synthesis device for process reinforcement of metal catalyst preparation [J]. Chemical Industry and Engineering Progress, 2024, 43(1): 246-259.
[11]	WANG Yiyan, WANG Darui, SHEN Zhenhao, HE Junlin, SUN Hongmin, YANG Weimin. Preparation and catalytic performance of fully crystalline MCM-22 zeolite catalyst [J]. Chemical Industry and Engineering Progress, 2024, 43(1): 285-291.
[12]	YU Xiaoxiao, CHAO Yanhong, LIU Haiyan, ZHU Wenshuai, LIU Zhichang. Enhanced photoelectric properties and photocatalytic CO₂ conversion by D-A conjugated polymerization [J]. Chemical Industry and Engineering Progress, 2024, 43(1): 292-301.
[13]	SUN Jin, CHEN Xiaozhen, LIU Mingrui, LIU Li, NIU Shikun, GUO Rong. Deactivation mechanism of sodium poisoning hydrodesulfurization catalyst [J]. Chemical Industry and Engineering Progress, 2024, 43(1): 407-413.
[14]	ZHANG Haipeng, WANG Shuzhen, MA Mengxi, ZHANG Wei, XIANG Jiangnan, WANG Yuting, WANG Yan, FAN Binbin, ZHENG Jiajun, LI Ruifeng. Synthesis of ZSM-22 molecular sieve and its n-dodecane hydroisomerization performance: Effect of template agent and dynamic crystallization [J]. Chemical Industry and Engineering Progress, 2024, 43(1): 414-421.
[15]	YANG Xue, LIU Ke, ZHANG Chengxiang, LI Donglin, WANG Jiangqin, YANG Wanliang. Research progress of 2D layered materials for fuel oil oxidation desulfurization [J]. Chemical Industry and Engineering Progress, 2024, 43(1): 422-436.