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

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

Abstract

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

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

CLC Number:

TQ426.6

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.

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.

Figures/Tables 17

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

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

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

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

Fig.5 Metal oxygen intermediate[36]

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

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

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]

Fig.9 Structure of catalyst[39]

Fig.10 Catalytic mechanism diagram[41]

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

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

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

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

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

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

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

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

烯烃和CO₂直接合成环状碳酸酯的催化剂研究进展

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