欢迎访问过程工程学报, 今天是
综述

烯烃和CO2直接合成环状碳酸酯的催化剂研究进展

  • 胡启鲁 ,
  • 赵国英 ,
  • 于彩虹
展开
  • 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
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.

收稿日期: 2020-06-19

  修回日期: 2020-08-28

  网络出版日期: 2021-07-27

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 HU ,
  • Guoying ZHAO ,
  • Caihong YU
Expand
  • 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 date: 2020-06-19

  Revised date: 2020-08-28

  Online published: 2021-07-27

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。

本文引用格式

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

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.

参考文献

1 Lu X B, Darensbourg D J. Cobalt catalysts for the coupling of CO2 and epoxides to provide polycarbonates and cyclic carbonates [J]. Chemical Society Reviews, 2012, 41(4): 1462-1484.
2 Liang J, Huang Y B, Cao R, et al. Metal-organic frameworks and porous organic polymers for sustainable fixation of carbon dioxide into cyclic carbonates [J]. Coordination Chemistry Reviews, 2017, 378(SI): 32-65.
3 Sun J, Fujita S I, Zhao F, et al. A direct synthesis of styrene carbonate from styrene with the Au/SiO2-ZnBr2/Bu4NBr catalyst system [J]. Journal of Catalysis, 2005, 230(2): 398-405.
4 North M, Pasquale R, Young C, et al. Synthesis of cyclic carbonates from epoxides and CO2 [J]. Green Chemistry, 2010, 12(9): 1514-1539.
5 Cheng W G, Su Q, Wang J Q, et al. Ionic liquids: the synergistic catalytic effect in the synthesis of cyclic carbonates [J]. Catalyst, 2013, 3(4): 878-901.
6 Liu J H, Zhao G Y, Cheung O, et al. Highly porous metalloporphyrin covalent ionic frameworks with well-defined cooperative functional groups as excellent catalysts for CO2 cycloaddition [J]. Chemistry-A European Journal, 2019, 25(38): 9052-9059.
7 Sun J, Liang L, Sun J, et al. Direct synthetic processes for cyclic carbonates from olefins and CO2 [J]. Catalysis Surveys from Asia, 2011, 15(1): 49-54.
8 Xia Q, Ge H, Ye C, et al. Advances in homogeneous and heterogeneous catalytic asymmetric epoxidation [J]. Chemical Reviews, 2005, 105(5): 1603-1662.
9 Amarajothi D, Hermenegildo G. Cascade reactions catalyzed by metal organic frameworks [J]. Chemsuschem, 2014, 7(9): 2392-2410.
10 李享. 以CO2与烯烃为原料合成丁二酸和环状碳酸酯的研究[D]. 广州: 华南理工大学, 2019: 10.
10 Li H. Study on the synthesis of succinic acid and cyclic carbonate from CO2 and olefins [D]. Guangzhou: South China University of Technology, 2019: 10.
11 刘宝航, 王伟建. 二氧化碳加氢合成低碳烯烃催化剂的研究进展 [J]. 安徽化工, 2019, 45(5): 11-14, 17.
11 Liu B H, Wang W J. Research progress of catalysts for hydrogenation of carbon dioxide to low olefins [J]. Anhui Chemical Industry, 2019, 45(5): 11-14, 17.
12 Bajracharya S, Srikanth S, Mohanakrishna G, et al. Biotransformation of carbon dioxide in bioelectrochemical systems: state of the art and future prospects [J]. Journal of Power Sources, 2017, 356(15): 256-273.
13 Wang J, Petit C, Zhang X, et al. Simultaneous measurement of CO2 sorption and swelling of phosphate-based ionic liquid [J]. Green Energy & Environment, 2016, 1(3): 258-265.
14 刘佳慧, 刘会婷, 赵国英, 等. 离子液体自模板合成多孔碳氮材料及其对二氧化碳的吸附 [J]. 过程工程学报, 2020, 20(1): 108-115.
14 Liu J H, Liu H T, Zhao G Y, et al. Ionic liquids self-templating to synthesize nitrogen-doped porous carbon materials for CO2 adsorption [J]. The Chinese Journal of Process Engineering, 2020, 20(1): 108-115.
15 Tebandeke E, Coman C, Guillois K, et al. Epoxidation of olefins with molecular oxygen as the oxidant using gold catalysts supported on polyoxometalates [J]. Green Chemistry, 2014, 16(3): 1586-1593.
16 Suttikul T, Paosombat B, Santikunaporn M, et al. Improvement of ethylene epoxidation in a parallel plate dielectric barrier discharge system by ethylene/oxygen separate feed and Ag catalyst [J]. Industrial and Engineering Chemistry Research, 2014, 53(10): 3778-3786.
17 邹波. 从烯烃出发合成环状碳酸酯研究 [D]. 北京: 北京理工大学, 2016: 15.
17 Zou B. Study on the synthesis of cyclic carbonate from olefin [D]. Beijing: Beijing University of Technology, 2016: 15.
18 Kohno K, Sakakura T. Catalytic transformation of carbon dioxide to organic carbonates [J]. ChemInform, 2009, 67(9): 921-933.
19 Song Q W, Zhou Z H, He L N. Efficient, selective and sustainable catalysis of carbon dioxide [J]. Green Chemistry, 2017, 19(16): 3707-3728.
20 Liu Q, Wu L, Jackstell R, et al. Using carbon dioxide as a building block in organic synthesis [J]. Nature Communications, 2015, 47(13): 5933.
21 Sankar M, Tarte N H, Manikandan P. Effective catalytic system of zinc-substituted polyoxometalate for cycloaddition of CO2 to epoxides [J]. Applied Catalysis A: General, 2004, 276(1/2): 217-222.
22 Bai D S, Jing H Q. Aerobic oxidative carboxylation of olefins with metalloporphyrin catalysts [J]. Green Chemistry, 2009, 12(1): 39-41.
23 Ramidi P, Felton C M, Subedi B P, et al. Synthesis and characterization of manganese(III) and high-valent manganese-oxo complexes and their roles in conversion of alkenes to cyclic carbonates [J]. Journal of CO2 Utilization, 2015, 9: 48-57.
24 Abassian M, Zhiani R, Motavalizadehkakhky A, et al. A new class of organoplatinum-based DFNS for the production of cyclic carbonates from olefins and CO2 [J]. RSC Advances, 2020, 10, 15044-15051.
25 Zhang S, Xia Z M, Zou Y, et al. Interfacial frustrated lewis pairs of CeO2 activate CO2 for selective tandem transformation of olefins and CO2 into cyclic carbonates [J]. Journal of the American Chemical Society, 2019, 141(29): 11353-11357.
26 Dumbre D K, Choudhary V R, Patil N S, et al. Calcium oxide supported gold nanoparticles as catalysts for the selective epoxidation of styrene by t-butyl hydroperoxide [J]. Journal of Colloid and Interface Science, 2014, 415: 111-116.
27 Sun J M, Fujita S I, Zhao F Y, et al. A direct synthesis of styrene carbonate from styrene with the Au/SiO2-ZnBr2/Bu4NBr catalyst system [J]. Journal of Catalysis, 2005, 230(2): 398-405.
28 Wang Y L, Sun J H, Xiang D, et al. A facile, direct synthesis of styrene carbonate from styrene and CO2 catalyzed by Au/Fe(OH)3-ZnBr2/Bu4NBr system [J]. Catalysis Letters, 2009, 129(3/4): 437-443.
29 Maksimchuk N V, Ivanchikova I D, Ayupov A B, et al. One-step solvent-free synthesis of cyclic carbonates by oxidative carboxylation of styrenes over a recyclable Ti-containing catalyst [J]. Applied Catalysis B Environmental, 2016, 181: 363-370.
30 Gu B B, Xu T, Xu G R, et al. Synthesis of styrene carbonate from styrene and CO2 catalyzed by walnut-like zeolite LZ-276 [J]. Microporous and Mesoporous Materials, 2020, 293: 109779.
31 Zalomaeva O V, Maksimchuk N V, Chibiryaev A 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.
32 Nguyen P T K, Nguyen H T D, Nguyen H N, et al. New metal-organic frameworks for chemical fixation of CO2 [J]. ACS Applied Materials & Interfaces, 2018, 10(1): 733-744.
33 Nguyen H T D, Tran Y B N, Nguyen H N, et al. A series of metal-organic frameworks for selective CO2 capture and catalytic oxidative carboxylation of olefins [J]. Inorganic Chemistry, 2018, 57(21): 13772-13782.
34 Sharma N, Dhankhar S S, Kumar S, et al. Rational design of 3D Mn(II)-metal organic framework based on non-metallated porphyrin linker for selective capture of CO2 and one-pot synthesis of styrene carbonates [J]. Chemistry-A European Journal, 2018, 24(62): 16662-16669.
35 Aresta M, Quaranta E, Ciccarese A, et al. Direct synthesis of 1,3-benzodioxol-2-one from styrene, dioxygen and carbon-dioxide promoted by Rh(I) [J]. Journal of Molecular Catalysis, 1987, 41(3): 355-359.
36 Aresta M, Dibenedetto A, Tommasi I, et al. Direct synthesis of organic carbonates by oxidative carboxylation of olefins catalyzed by metal oxides: developing green chemistry based on carbon dioxide [J]. Applied Organometallic Chemistry, 2000, 14(12): 799-802.
37 Aresta M, Dibenedetto A. Carbon dioxide as building block for the synthesis of organic carbonates [J]. Molecular Catalysis, 2002, 182(1): 399-409.
38 Liu J, Yang G Q, Liu Y, et al. Metal-free imidazolium hydrogen carbonate ionic liquids as bifunctional catalysts for the one-pot synthesis of cyclic carbonates from olefins and CO2 [J]. Green Chemistry, 2019, 21(14): 3834-3838.
39 Kumar S, Singhal N, Singh R K, et al. Dual catalysis with magnetic chitosan: direct synthesis of cyclic carbonates from olefins with carbon dioxide using isobutyraldehyde as the sacrificial reductant [J]. Dalton Transactions, 2015, 44(26): 11860-11866.
40 Huang Z J, Li F B, Chen B F, et al. Well-dispersed g-C3N4 nanophases in mesoporous silica channels and their catalytic activity for carbon dioxide activation and conversion [J]. Applied Catalysis B Environmental, 2013, 136: 269-277.
41 Han Q X, Qi B, Ren W M, et al. Polyoxometalate-based homochiral metal-organic frameworks for tandem asymmetric transformation of cyclic carbonates from olefins [J]. Nature Communications, 2015, 6: 10007.
42 Yu K, Puthiaraj P, Ahn W S. One-pot catalytic transformation of olefins into cyclic carbonates over an imidazolium bromide-functionalized Mn(III)-porphyrin metal-organic framework [J]. Applied Catalysis B: Environmental, 2020, 273: 119059.
43 Chen F W, Dong T, Xu T G, et al. Direct synthesis of cyclic carbonates from olefins and CO2 catalyzed by a MoO2(acac)2-quaternary ammonium salt system [J]. Green Chemistry, 2011, 13(9): 2518-2524.
44 Siewniak A, Jasiak-Jaron K, Kotyrba L, et al. Efficient catalytic system involving molybdenyl acetylacetonate and immobilized tributylammonium chloride for the direct synthesis of cyclic carbonates from carbon dioxide and olefins [J]. Catalysis Letters, 2017, 147(6): 1567-1573.
45 Dias L D, Carrilho R M B, Henriques C A, et al. Hybrid-metalloporphyrin magnetic nanoparticles as catalysts for sequential transformation of alkenes and CO2 into cyclic carbonates [J]. ChemCatChem, 2018, 10(13): 2792-2803.
46 Engel R V, Alsaiari R, Nowicka E, et al. Oxidative carboxylation of 1-decene to 1,2-decylene carbonate [J]. Topics in Catalysis, 2018, 61(5/6): 509-518.
47 Xiang D, Liu X F, Sun J S, et al. A novel route for synthesis of styrene carbonate using styrene and CO2 as substrates over basic resin R201 supported Au catalyst [J]. Catalysis Today, 2009, 148(3/4): 383-388.
48 Srivastava R, Srinivas D, Ratnasamy P. Synthesis of polycarbonate precursors over titanosilicate molecular sieves [J]. Catalysis Letters, 2003, 91(1/2): 133-139.
49 Shi Z L, Niu G Q, Han Q X, et al. A molybdate-incorporated cooperative catalyst: high efficiency in the assisted tandem catalytic synthesis of cyclic carbonates from CO2 and olefins [J]. Molecular Catalysis, 2018, 461: 10-18.
50 Ke S C, Luo T T, Chang G G, et al. Spatially ordered arrangement of multifunctional sites at molecule level in a single catalyst for tandem synthesis of cyclic carbonates [J]. Inorganic Chemistry, 2020, 59(3): 1736-1745.
51 Zhao G D, Zhang Y, Zhang H Y, et al. Direct synthesis of propylene carbonate from propylene and carbon dioxide catalyzed by quaternary ammonium heteropolyphosphatotungstate-TBAB system [J]. Journal of Energy Chemistry, 2015, 24(3): 353-358.
52 刘伟, 钱静怡, 曹新宇, 等. 用于烯烃环氧化反应的甲基三氧化铼催化体系的研究进展 [J]. 吉林师范大学学报(自然科学版), 2018, 39(4): 30-35.
52 Liu W, Qian J Y, Cao X Y, et al. The research progress in catalytic system of methyltrioxorhenium for olefin epoxidation [J]. Journal of Jilin Normal University (Natural Science Edition), 2018, 39(4): 30-35.
53 Ono F, Qiao K, Tomida D, et al. Direct preparation of styrene carbonates from styrene using an ionic liquid-based one-pot multistep synthetic process [J]. Applied Catalysis A: General, 2007, 333(1): 107-113.
54 Sathe A A, Nambiar A M K, Rioux R M, et al. Synthesis of cyclic organic carbonates via catalytic oxidative carboxylation of olefins in flow reactors [J]. Catalysis Science & Technology, 2016, 7(1): 84-89.
55 Zhang J, Liu Y M, Li N N, et al. Synthesis of propylene carbonate on a bifunctional titanosilicate modified with quaternary ammonium halides [J]. Chinese Journal of Catalysis, 2008, 29(7): 589-591.
56 Sun J M, Fujita S I, Bhanage B M, et al. One-pot synthesis of styrene carbonate from styrene in tetrabutylammonium bromide [J]. Catalysis Today, 2004, 93/94/95: 383-388.
57 孙建敏, 王亚丽, 屈学俭, 等.溴化四丁铵催化苯乙烯一步合成苯乙烯环状碳酸酯 [J]. 高等学校化学学报, 2006, 4(8): 1522-1525.
57 Sun J M, Wang Y L, Qu X J, et al. New route to direct synthesis styrene carbonate from styrene catalyzed by quaternary ammonium bromide [J]. Chemical Journal of Chinese Universities, 2006, 4(8): 1522-1525.
58 Wang J L, Wang J Q, He L N, et al. A CO2/H2O2-tunable reaction: direct conversion of styrene into styrene carbonate catalyzed by sodium phosphotungstate/n-Bu4NBr [J]. Green Chemistry, 2008, 10(11): 1218-1223.
59 Girard A L, Simon N, Zanatta M, et al. Insights on recyclable catalytic system composed of task-specific ionic liquids for the chemical fixation of carbon dioxide [J]. Green Chemistry, 2014, 16(5): 2815-2825.
60 Yang X Q, Wu J, Mao X W, et al. Microwave assisted synthesis of cyclic carbonates from olefins with sodium bicarbonates as the C1 source [J]. Chemical Communications, 2014, 50(24): 3245-3248.
61 Xie J N, Diao Z F, Qiao C, et al. One-pot stepwise synthesis of cyclic carbonates directly from olefins with CO2 promoted by K2S2O8/NaBr [J]. Journal of CO2 Utilization, 2016, 16: 313-317.
62 Gao X F, Yuan G Q, Chen H J, et al. Efficient conversion of CO2 with olefins into cyclic carbonates via a synergistic action of I2 and base electrochemically generated in situ [J]. Electrochemistry Communications, 2013, 34: 242-245.
63 Eghbali N, Li C J. Conversion of carbon dioxide and olefins into cyclic carbonates in water [J]. Green Chemistry, 2007, 9(3): 213-215.
64 Davies S G, Fletcher A M, Kurosawa W, et al. One-pot conversions of olefins to cyclic carbonates and secondary allylic and homoallylic amines to cyclic carbamates [J]. Journal of Organic Chemistry, 2010, 75(22): 7745-7756.
65 Wu J, Kozak J A, Simeon F, et al. Mechanism-guided design of flow systems for multicomponent reactions: conversion of CO2 and olefins to cyclic carbonates [J]. Chemical Science, 2014, 5(3): 1227-1231.
文章导航

/