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

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

摘要/Abstract

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

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

中图分类号:

TQ203.2

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.

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.

图/表 16

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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]

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

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

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