多孔超交联聚合物固载离子液体催化二氧化碳环加成反应的研究进展

doi:10.16085/j.issn.1000-6613.2020-0915

摘要/Abstract

摘要：

CO₂是一种主要的温室气体，以CO₂为原料与环氧化物发生环加成反应可以制备各种环状碳酸酯，是一种绿色可行的CO₂捕集及利用途径。多孔超交联聚合物固载离子液体（hypercrosslinked polymers immobilized ionic liquids，HCP-ILs）催化CO₂环加成反应具有无需溶剂、金属和助催化剂等优点。本文对其近年来的最新研究进展进行了综述，总结了离子单体自聚/共聚或交联法、离子与交联一步法以及交联后修饰法三种制备超交联聚合物固载离子液体方法的特点，分析了目前还存在离子密度偏低、催化效率不够高以及制备成本偏高等不利于“CO₂化工”应用的问题，并指出为实现在常压下快速催化CO₂与环氧化物的环加成反应，应从提高离子密度、调控表面活化功能基团和离子微环境以及降低制备成本等方向加强理论研究和技术攻关。

关键词: 固载离子液体, 超交联聚合物, 二氧化碳, 环加成反应, 催化

Abstract:

CO₂ is one of the main greenhouse gases, and the cycloaddition of CO₂ with epoxides can produce various cyclic carbonates, which is a relative green, economical and feasible way for CO₂ capture and utilization. Using porous hypercrosslinked polymers immobilized ionic liquids (HCPs-ILs) to catalyze the CO₂ cycloaddition reaction does not require solvents, metals and co-catalysts. In this review, we summarized the recent research progress on CO₂ cycloaddition catalyzed by HCPs-ILs, as well as the characteristics of three methods for preparing hypercrosslinked polymer immobilized ionic liquids, namely ionic monomer self-polymerization/copolymerization or crosslinking method, one-step method of simultaneous formation of ions and crosslinking, and post modification method. The problems that are not conducive to the application of “CO₂ chemical industry” such as low ionic density, insufficient catalytic efficiency, and high preparation cost were also analyzed. Finally, we pointed out that in order to realize the rapid catalysis of the cycloaddition reaction of CO₂ with epoxides under normal pressure, theoretical and technical researches should be strengthened from the aspects of increasing ionic density, regulating the surface activation functional groups and ionic microenvironment, and reducing the preparation costs.

Key words: immobilized ionic liquids, hypercrosslinked polymers, carbon dioxide, cycloaddition reaction, catalysis

中图分类号:

O631.5

赵朝阳, 罗小燕, 裴宝有, 项小燕, 李佳然, 马瑞勋, 张子姮, 林金清. 多孔超交联聚合物固载离子液体催化二氧化碳环加成反应的研究进展[J]. 化工进展, 2021, 40(3): 1438-1448.

ZHAO Zhaoyang, LUO Xiaoyan, PEI Baoyou, XIANG Xiaoyan, LI Jiaran, MA Ruixun, ZHANG Ziheng, LIN Jinqing. Research progress on CO₂ cycloaddition catalyzed by porous hyper-crosslinked polymers immobilized ionic liquids[J]. Chemical Industry and Engineering Progress, 2021, 40(3): 1438-1448.

图/表 8

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催化剂	单体	底物	压力 /MPa	温度 /℃	时间 /h	产率 /%	参考文献
AIMDFP	双氰胺	环氧丙烷	2	130	3.5	99	[30]
P(DMAEMA-EtOH)Br	甲基丙烯酸二甲氨基乙酯	环氧丙烷	2	110	3	96.2	[32]
PDMBr	1-乙烯基咪唑	环氧丙基苯基醚	0.1	70	48	90	[33]
PIP-Bn-Cl	乙烯基功能化的三苯基膦	环氧丙烷	0.1	50	24	93.2	[34]
Polymer 1	三苯基膦	氧化苯乙烯	1	130	12	96	[35]
PVIm-6-SCD	1-乙烯基咪唑1,2,3,4,5,6-六苄溴苯	环氧丙烷	0.1	50	24	99.5	[36]
DVB@ISA	1-乙烯基咪唑二乙烯基苯1,2-环己二胺	1,2-环氧己烷	1	60	24	99	[37]
AE-PIL-Cl	1-乙烯基咪唑乙烯基苯	环氧丙烷	1	140	60	99	[38]
1P⁺Br^-&1PPh₃@POPs	乙烯基功能化的三苯基膦	环氧丙烷	3	120	5	90	[39]
IHCP-OH(1)	二乙烯基苯 1-乙烯基咪唑等	环氧丙基苯基醚	1	120	2	90	[40]
[AlTMG]Br	乙烯基苯功能化的季铵离子液体	环氧苯乙烯	0.1	100	6	99	[41]
[PAD][IDA]	二乙烯基苯 1-乙烯基咪唑	环氧苯乙烯	0.1	65	12	99	[42]
Py-Im-6	1-乙烯基咪唑1,2,3,4,5,6-六苄溴	环氧丙烷	0.1	120	1	94.5	[43]
PIL-4	1-乙烯基咪唑二(2-氯乙基)醚	环氧氯丙烷	1	100	12	99	[44]
NHC-CAP-1（Zn²⁺）	苯基咪唑等	环氧氯丙烷	2	100	3	97	[45]
I_C2HCP-5b	1-苄基咪唑等	环氧氯丙烷	3	120	20	99	[47]
IM-iPHP-2	1-苄基咪唑VPSOSS	环氧氯丙烷	0.1	80	48	99	[48]
V-iPHP-1	4,4-联吡啶等	环氧氯丙烷	0.1	60	72	99	[49]
T-IM	含咪唑的交联单体等	环氧氯丙烷	1	140	10	87(¹H NMR)	[50]
PP-Br	三（4-氯苯基）膦	环氧丙基苯基醚	0.1	140	20	98.5	[51]
CPP-IL	1,2-二甲基-3-(丙-2-炔基)-1H-咪唑-3-溴化铵等	环氧氯丙烷	0.1	100	24	99	[52]
PAM-PyMe(Cl)	2,6-二氨基吡啶	环氧氯丙烷	0.1	100	20	77	[53]
UIIP	含有咪唑的交联单体	环氧丙烷	1	110	2	97	[54]
HIP-Br-2	苯基咪唑等	环氧丙烷	0.1	55	96	99	[55]
HPILs-Cl	苯基咪唑等	环氧丙烷	0.1	70	9	99(¹H NMR)	[56]
IMIN-Br-OH	咪唑修饰的四苯甲烷	环氧氯丙烷	0.1	40	72	99(¹H NMR)	[57]
HMIB	1,4-对二氯苄咪唑	环氧丙烷	1	110	1.5	90	[58]
COP-222	对苯二甲醛氯化铵	环氧氯丙烷	0.1	100	24	99(¹H NMR)	[3]
POM3-IM	1-甲基咪唑等	环氧丙烷	1	120	4	78	[59]
PS-[CETBD]Br	氯球（PS-Cl）	环氧丙烷	2	140	2	96.3	[50]
PQA-NH₂Py-Br	2-氨基吡啶	1-丁基-2-苯基氮丙啶	2	70	4	99(¹H NMR)	[61]
催化剂 7	4-乙烯基吡啶	环氧丙基苯醚	0.1	80	12	66(¹H NMR)	[62]

催化剂	单体	底物	压力 /MPa	温度 /℃	时间 /h	产率 /%	参考文献
AIMDFP	双氰胺	环氧丙烷	2	130	3.5	99	[30]
P(DMAEMA-EtOH)Br	甲基丙烯酸二甲氨基乙酯	环氧丙烷	2	110	3	96.2	[32]
PDMBr	1-乙烯基咪唑	环氧丙基苯基醚	0.1	70	48	90	[33]
PIP-Bn-Cl	乙烯基功能化的三苯基膦	环氧丙烷	0.1	50	24	93.2	[34]
Polymer 1	三苯基膦	氧化苯乙烯	1	130	12	96	[35]
PVIm-6-SCD	1-乙烯基咪唑1,2,3,4,5,6-六苄溴苯	环氧丙烷	0.1	50	24	99.5	[36]
DVB@ISA	1-乙烯基咪唑二乙烯基苯1,2-环己二胺	1,2-环氧己烷	1	60	24	99	[37]
AE-PIL-Cl	1-乙烯基咪唑乙烯基苯	环氧丙烷	1	140	60	99	[38]
1P⁺Br^-&1PPh₃@POPs	乙烯基功能化的三苯基膦	环氧丙烷	3	120	5	90	[39]
IHCP-OH(1)	二乙烯基苯 1-乙烯基咪唑等	环氧丙基苯基醚	1	120	2	90	[40]
[AlTMG]Br	乙烯基苯功能化的季铵离子液体	环氧苯乙烯	0.1	100	6	99	[41]
[PAD][IDA]	二乙烯基苯 1-乙烯基咪唑	环氧苯乙烯	0.1	65	12	99	[42]
Py-Im-6	1-乙烯基咪唑1,2,3,4,5,6-六苄溴	环氧丙烷	0.1	120	1	94.5	[43]
PIL-4	1-乙烯基咪唑二(2-氯乙基)醚	环氧氯丙烷	1	100	12	99	[44]
NHC-CAP-1（Zn²⁺）	苯基咪唑等	环氧氯丙烷	2	100	3	97	[45]
I_C2HCP-5b	1-苄基咪唑等	环氧氯丙烷	3	120	20	99	[47]
IM-iPHP-2	1-苄基咪唑VPSOSS	环氧氯丙烷	0.1	80	48	99	[48]
V-iPHP-1	4,4-联吡啶等	环氧氯丙烷	0.1	60	72	99	[49]
T-IM	含咪唑的交联单体等	环氧氯丙烷	1	140	10	87(¹H NMR)	[50]
PP-Br	三（4-氯苯基）膦	环氧丙基苯基醚	0.1	140	20	98.5	[51]
CPP-IL	1,2-二甲基-3-(丙-2-炔基)-1H-咪唑-3-溴化铵等	环氧氯丙烷	0.1	100	24	99	[52]
PAM-PyMe(Cl)	2,6-二氨基吡啶	环氧氯丙烷	0.1	100	20	77	[53]
UIIP	含有咪唑的交联单体	环氧丙烷	1	110	2	97	[54]
HIP-Br-2	苯基咪唑等	环氧丙烷	0.1	55	96	99	[55]
HPILs-Cl	苯基咪唑等	环氧丙烷	0.1	70	9	99(¹H NMR)	[56]
IMIN-Br-OH	咪唑修饰的四苯甲烷	环氧氯丙烷	0.1	40	72	99(¹H NMR)	[57]
HMIB	1,4-对二氯苄咪唑	环氧丙烷	1	110	1.5	90	[58]
COP-222	对苯二甲醛氯化铵	环氧氯丙烷	0.1	100	24	99(¹H NMR)	[3]
POM3-IM	1-甲基咪唑等	环氧丙烷	1	120	4	78	[59]
PS-[CETBD]Br	氯球（PS-Cl）	环氧丙烷	2	140	2	96.3	[50]
PQA-NH₂Py-Br	2-氨基吡啶	1-丁基-2-苯基氮丙啶	2	70	4	99(¹H NMR)	[61]
催化剂 7	4-乙烯基吡啶	环氧丙基苯醚	0.1	80	12	66(¹H NMR)	[62]

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