烯烃和CO2直接合成环状碳酸酯的催化剂研究进展

doi:10.12034/j.issn.1009-606X.220195

过程工程学报 ›› 2021, Vol. 21 ›› Issue (7): 762-773.DOI: 10.12034/j.issn.1009-606X.220195

烯烃和CO₂直接合成环状碳酸酯的催化剂研究进展

胡启鲁¹^,²(), 赵国英²(), 于彩虹¹()

^1.中国矿业大学(北京)化学与环境工程学院，北京 100083
^2.中国科学院过程工程研究所离子液体清洁过程北京市重点实验室，北京 100190

收稿日期:2020-06-19 修回日期:2020-08-28 出版日期:2021-07-28 发布日期:2021-07-27
通讯作者: 赵国英 2251125219@qq.com;gyzhao@ipe.ac.cn;caihongyu2013@126.com
作者简介:胡启鲁(1995-)，女，山东省茌平县人，硕士研究生，研究方向为离子材料与CO2催化转化，E-mail: 2251125219@qq.com；通讯联系人
赵国英，E-mail: gyzhao@ipe.ac.cn
于彩虹，E-mail: caihongyu2013@126.com.
基金资助:
国家自然科学基金资助项目(21878303);国家重点基础研究发展基金资助项目(2016YFB0601303)

Recent advances in catalysts for direct synthesis of cyclic carbonates from olefins and CO₂

Qilu HU¹^,²(), Guoying ZHAO²(), Caihong YU¹()

^1.College of Chemistry and Environment Engineering, China University of Mining and Technology, Beijing 100083, China
^2.Beijing Key Laboratory of Ionic Liquid Cleaning Process, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China

Received:2020-06-19 Revised:2020-08-28 Online:2021-07-28 Published:2021-07-27
Contact: Guoying ZHAO 2251125219@qq.com;gyzhao@ipe.ac.cn;caihongyu2013@126.com

摘要/Abstract

摘要：

利用丰富且价廉易得的烯烃和CO2直接反应可提供一种经济安全环保的高附加值环状碳酸酯生产工艺，具有减少CO2排放、缓解温室效应等优点。本工作以一步氧化羧化、顺序氧化羧化以及羟溴化羧化三种方法为主线，综述了近年来烯烃和CO2直接制备环状碳酸酯相关催化剂的研究进展，包括用于氧化羧化反应的催化剂，主要是同时具有烯烃环氧化催化功能和CO2羧化功能的多组分组合催化剂和多活性位点的单一催化剂，如金属氧化物、金属配合物、离子液体、改性分子筛、金属有机骨架化合物等；以及作用于羟溴化羧化反应的含Br-, I-阴离子的卤代试剂-无机/有机碱脱质子试剂组合催化剂。同时对未来烯烃和CO2制备环状碳酸酯反应的催化剂的设计及工艺开发进行了展望。

关键词: 烯烃, 环氧化, 羟溴化, 二氧化碳, 羧化, 环状碳酸酯

Abstract: The valorization of CO2 into value-added chemical compounds via economically viable process could be one of effective strategies to reduce CO2 emission and therefore the climate change impact. The cyclic carbonates are industrially produced by cycloadditions between CO2 and epoxides. However, there are safety risks in this technology due to the need to handle the flammable and explosive epoxides. Direct synthesis of cyclic carbonates from olefins and CO2 could provide a safer, more economic and environment-friendly alternative technology. Herein, the latest research progress in catalysts for synthesis of cyclic carbonates via one-step oxidative carboxylation, sequential oxidative carboxylation and hydroxyl bromide carboxylation of olefins is summarized. The reported catalysts for oxidative carboxylation approach are mainly multi-component composite catalysts, of which include at least both catalytic components for epoxidation of olefins and carboxylation with CO2. Single component catalysts with catalytic active function or site for both epoxidation of olefins and carboxylation with CO2, have been rarely reported in the literature and are also described here. The catalysts for hydroxyl bromide carboxylation of olefins typically consist of a halogenating reagent and an inorganic/organic base deprotonating reagent. The effects of reaction approach, catalyst structure/components, catalytic mechanism and reaction conditions on the yields and selectivity of CC are also systematically summarized and explored. In the view of green chemistry, oxidation carboxylation of olefin is of higher atom-economy and environmental benefits while hydroxyl bromide carboxylation is always accompanied by the formation of a large number of side-products. An efficient heterogeneous single component catalyst with integrated cooperative catalytic active sites for epoxidation, carboxylation, CO2 adsorption concentration, etc., which simplity the separation and recovery of catalysts and products, will be the future research trend of catalyst development for oxidative carboxylation of olefin with CO2 to produce cyclic carbonates.

Key words: olefin, epoxidation, hydroxy bromide, carbon dioxide, carboxylation, cyclic carbonate

中图分类号:

TQ426.6

胡启鲁, 赵国英, 于彩虹. 烯烃和CO₂直接合成环状碳酸酯的催化剂研究进展[J]. 过程工程学报, 2021, 21(7): 762-773.

Qilu HU, Guoying ZHAO, Caihong YU. Recent advances in catalysts for direct synthesis of cyclic carbonates from olefins and CO₂[J]. The Chinese Journal of Process Engineering, 2021, 21(7): 762-773.

图/表 17

图1 烯烃直接制备环状碳酸酯的三种方法

Fig.1 Three ways for the direct preparation of cyclic carbonate from olefins

图2 [Ru(TPP)(O)2]/季铵盐催化烯烃和CO2制备CC[22]

Fig.2 Synthesis of CC from olefin and CO2 catalyzed by [Ru(TPP)(O)2]/quaternary ammonium salt[22]

图3 新型锰(Ⅲ)配合物1和锰氧化合物中间体2的结构和反应条件[23]

Fig.3 Structure of a new manganese (Ⅲ) complex 1 and intermediate of manganese oxide compounds 2 and reaction conditions[23]

图4 从苯乙烯一步合成SC的反应过程[27]

Fig.4 One step synthesis of SC from styrene[27]

图5 金属氧中间体[36]

Fig.5 Metal oxygen intermediate[36]

图6 苯甲醛作为一氧转移促进剂[37]

Fig.6 Benzaldehyde as an oxy transfer promoter[37]

图7 卤化物离子稳定金属氧中间体并催化环氧化物羧化[37]

Fig.7 Halide ion stabilizes metal oxygen intermediate and catalyzes the carboxylation of epoxide[37]

图8 催化剂[C n C m Im][HCO3]的结构和由此衍生的卡宾-CO2 (C n C m -CO2)之间的平衡[38]

Fig.8 The equilibrium between the structure of catalyst [C n C m Im][HCO3] and its derived carbene-CO2 (C n C m -CO2)[38]

图9 催化剂结构[39]

Fig.9 Structure of catalyst[39]

图10 催化机理图[41]

Fig.10 Catalytic mechanism diagram[41]

图11 乙酰丙酮钼[MoO2(acac)2]和TBAB催化过程[43]

Fig.11 Catalytic process of molybdenum acetylacetonate [MoO2(acac)2] and TBAB[43]

图12 MNP@SiO2-8Mn (1)和MNP@SiO2-4Cr (2)[45]

Fig.12 MNP@SiO2-8Mn (1) and MNP@SiO2-4Cr (2)[45]

图13 钛硅分子筛和助催化剂协同作用[48]

Fig.13 Synergistic effect of titanium silicalite and cocatalyst[48]

图14 季铵杂多磷钨酸盐和TBAB催化机理示意图[51]

Fig.14 Schematic diagram of catalytic mechanism of quaternary ammonium heteropolyphosphate tungstate and TBAB[51]

图15 苯乙烯和CO2直接合成环状碳酸酯[58]

Fig.15 Direct synthesis of cyclic carbonate from styrene and CO2[58]

图16 烯烃和CO2一步制备CC的可能机理[61]

Fig.16 Possible mechanism of one step synthesis of CC from olefin and CO2[61]

图17 m-CPBA/Br3CCOOH/DBU系统催化作用示意图[64]

Fig.17 Catalytic action diagram of m-CPBA/Br3CCOOH/DBU system[64]

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烯烃和CO₂直接合成环状碳酸酯的催化剂研究进展

Recent advances in catalysts for direct synthesis of cyclic carbonates from olefins and CO₂

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