均相与多相催化剂在CO<sub>2</sub>环加成反应中的研究进展

李宁宁; 刘轩博; 张宇航; 王雨佳; 常涛; 朱正

doi:10.19906/j.cnki.JFCT.2023052

均相与多相催化剂在CO₂环加成反应中的研究进展

doi: 10.19906/j.cnki.JFCT.2023052

李宁宁^1,,
刘轩博^1,,
张宇航^1,,
王雨佳^1,,
常涛^{1, 2, ,},
朱正^1, ,

1.
河北工程大学材料科学与工程学院邯郸市CO₂催化转化重点实验室, 河北邯郸056038
2.
河北省杂环化合物重点实验室, 河北邯郸056005

基金项目: 中央引导地方科技发展资金项目(226Z4304G)和河北省自然科学基金(B2020402002，E2021402017)资助

详细信息

通讯作者:
E-mail: changt03@sina.com

zhuzheng@hebeu.edu.cn

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出版历程
- 收稿日期: 2023-04-13
- 修回日期: 2023-05-27
- 录用日期: 2023-05-29
- 网络出版日期: 2023-09-01

Research progress of homogeneous and heterogeneous catalysts in CO₂ cycloaddition reactions

LI Ningning^1
,,
LIU Xuanbo^1
,,
ZHANG Yuhang^1
,,
WANG Yujia^1
,,
CHANG Tao^{1, 2
, ,},
ZHU Zheng^{1
, ,}

1.
Key Laboratory of CO₂ Utilization of Handan City, College of Material Science and Engineering, Hebei University of Engineering, Handan 056038 Hebei, China
2.
Key Laboratory of Heterocyclic Compounds of Hebei Province, Handan College, Handan 056005 Hebei, China

Funds: Project supported by the Central Guidance on Local Science and Technology Development Fund of Hebei Province (226Z4304G), the Hebei Natural Science Foundation (B2020402002, E2021402017).

摘要

摘要: 二氧化碳（CO₂）是一种主要的人为温室气体，主要由化学、热电和钢铁工业以及运输等部门产生。大气层中CO₂浓度的增加是导致诸多环境问题的主要原因，如全球变暖、海平面上升和全球气温升高。然而，CO₂作为一种可再生的、廉价的和无毒的化学原料，可用来生产具有高附加值的化学品，进而降低碳浓度是一个非常理想的策略。五元环碳酸酯由于其优越的物理化学特性，如高沸点、高偶极矩和生物降解等性能而被广泛应用。由环氧化合物和CO₂合成环碳酸酯是迄今为止研究较多的方法。然而，由于CO₂的高热稳定性和动力学惰性，使其作为反应原料需要大量的能量投入，可能导致的结果是CO₂浓度是一个净增长过程。因此，利用CO₂作为C1构筑单元是一个长期的挑战。本工作基于CO₂固定反应机制，概述了各种类型的均相和多相催化剂在CO₂固定反应合成精细化学品环状碳酸酯中的研究进展，包括有机催化剂、离子液体、金属有机框架化合物、多孔有机聚合物等。目前，几乎所有类别催化剂均可以在室温和低压力下，以实验室规模成功地使用纯CO₂将其固定到末端环氧化合物上，对于非末端环氧化合物通过更高的温度和压力以实现相应转化。同时，分析了催化剂在多取代环氧化合物或生物衍生环氧化合物转化、低浓度CO₂转化和实现工业化三个方面所面临的挑战，并提出了未来相关研究努力的方向。
- CO₂ /
- 环氧化合物 /
- 催化剂 /
- 环加成反应 /
- 环碳酸酯
Abstract: Carbon dioxide (CO₂) is a major anthropogenic greenhouse gas produced by chemical, thermoelectric and steel industries as well as transport sector. The increasing concentration of CO₂ in atmosphere is responsible for plenty of environmental problems such as global warming, rising sea levels and increasing global temperatures. However, CO₂ could consider as renewable, cheap and non-toxic chemical raw material, using CO₂ to produce high value-added chemicals to reduce carbon concentrations is a highly desirable strategy. Five-membered cyclic carbonates have a wide range of applications due to their superior physicochemical properties such as high boiling point, high dipole moment and biodegradability. The synthesis of cyclic carbonates from epoxides and CO₂ is by far the most approved method. Nevertheless, due to high thermal stability and kinetic inertness, it is necessary to activate CO₂ as feedstock for organic synthesis with large energy, which may result in the release of more CO₂ than is actually. Therefore, the use of CO₂ as C1 building block is long-term challenged. This paper outlines the progress of research on various types of homogeneous and heterogeneous catalysts for CO₂ fixation to generate cyclic carbonates, including organocatalysts, ionic liquids, metal-organic frameworks, and porous organic polymers. Almost all of these catalysts are currently available for the successful fixation of CO₂ to terminal epoxides on laboratory scale using pure CO₂ at ambient temperatures. For internal epoxides higher reaction conditions are usually required to achieve the desired conversion. It was analyzed three areas of present major challenges in catalyzing multi-substituted epoxides or bio-derived epoxides, diluted CO₂ conversion and industrialization, and the directions for future research efforts on the subject were suggested.
- carbon dioxide /
- epoxide /
- catalyst /
- cycloaddition reaction /
- cyclic carbonates

HTML全文

图 1 CO₂与环氧化合物环加成反应中催化剂分类

Figure 1 Classification of catalysts for cycloaddition of epoxides with CO₂

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图 2 CO₂与环氧化合物环加成的反应机理

Figure 2 Reaction mechanistic pathways of cycloaddition of epoxide with CO₂

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图 3 双功能咪唑ILs的合成路线

Figure 3 Synthetic route of bifunctional imidazolium ionic liquids

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图 4 [VIMEtOH][Br]-72 的合成路线

Figure 4 Synthetic route of [VIMEtOH][Br]-72

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图 5 咪唑基ILs的合成路线

Figure 5 Synthetic route of imidazole ionic liquid (ILs)

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图 6 质子双苯并咪唑盐的合成

Figure 6 Synthesis of protic bis-benzimidazolium salts

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图 7 (a) NEt(HE)₃Br分子结构; (b)双功能多羟基ILs的合成

Figure 7 (a) Structure of NEt(HE)₃Br; (b) Synthesis of bifunctional multi-hydroxyl ILs

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图 8 磷盐基催化剂

Figure 8 Phosphonium-based catalysts

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图 9 吡啶基催化剂

Figure 9 Pyridinium-based catalysts

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图 10 DBU基催化剂

Figure 10 DBU-based catalysts

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图 11 DES催化剂

Figure 11 DES catalysts

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图 12 （a）Sc-Salen 1a、（b）Salen-Ti，V、（c）（inden）Cr^III 、（d）Al-Salen 3·(sol)₂和（e）双核铬配合物的结构

Figure 12 Structure of (a) Sc-Salen 1a, (b) Salen-Ti, V, (c) inden-Cr^III (d) Al-Salen 3·(sol)₂ and (e) dichroic chromium complexes

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图 13 （a）双核镍催化剂及（b）大环配合物的结构

Figure 13 Structure of (a) dual-core nickel catalyst and (b) Macrocyclic complex

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图 14 锌配合物的结构及配合物/TBAB体系催化CO₂/PO环加成反应的机理

Figure 14 Structure of zinc complex and mechanism of CO₂/PO coupling catalyzed by the complex /TBAB system

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图 15 （a）[Mn^III（T2,3-DCPP）X]、（b）(CoCl)₂-1^[60]和（c） M^IIPzs的结构

Figure 15 Structure of (a) [Mn^III（T2,3-DCPP）X], (b) (CoCl)₂-1^[60] and (c) M^IIPzs. With permission from Wiley Publications

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图 16 （a）双功能Al配合物、（b）高铁酸盐配合物和（c） Fe（II）亚氨基吡啶配合物的结构

Figure 16 Structure of (a)bifunctional Al, (b) Fe(II) iminopyridine and (c) ferrate complexes

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图 17 将金属salophen配合物固定在丙胺官能化SBA-15二氧化硅上的共价接枝策略

Figure 17 Covalent grafting strategy for fixation of metallic salophen complex onto propyl functionalized SBA-15 silica

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图 18 KIT-6@ILCH₃CH (OH) COO (0.6）催化CO₂与环氧化合物环加成反应机理

Figure 18 Possible reaction mechanism for the cycloaddition of CO₂ with epoxides catalyzed by KIT-6@ILCH₃CH(OH)COO(0.6)

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图 19 ZrO₂/g-C₃N₄催化环加成反应的可能机理

Figure 19 A possible mechanism of cycloaddition reaction catalyzed by ZrO₂/g-C₃N₄

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图 20 化合物Cu MOF单晶结构：（a）两种Cu配位模式和CPTPTA⁵⁻配体的多面体简化；（b）球棒视图和（c）沿[001]框架的多面体视图^[85]

Figure 20 Single-crystal structure of compound Cu MOF: (a) polyhedral simplifications of two kinds of Cu coordination modes and CPTPTA5− ligand; (b) ball-and-stick view and (c) polyhedral view of the framework along [001]^[85] (with permission from RSC Publications)

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图 21 Co(II)-MOF NRs/TBAB催化过程中环氧化合物活化和环加成的可能机制示意图

Figure 21 Schematic for the possible mechanisms of epoxide activation and cycloaddition during Co(II)-MOF NRs/TBAB-based catalysis

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图 22 COF-SO₃H的合成方案

Figure 22 The synthesis scheme of COF-SO₃H

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图 23 由Zn@TpTta/TBAB二进制系统催化的环氧乙烷和CO₂偶联的反应机理^[90]

Figure 23 Coupling mechanism of ethylene oxide and CO₂ catalyzed by Zn@TpTta/TBAB binary system ^[90] (with permission from RSC Publications)

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图 24 （a）2,5-DCP-CTF理想化建筑单元图解；（b）2,5-DCP-CTF的结构示意图^[93]

Figure 24 (a) 2,5-DCP-CTF idealized building unit diagram; (b) Structural diagram of 2, 5-DCCP-CTF^[93] (with permission from RSC Publications)

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图 25 CTF TPM的合成路线

Figure 25 Synthetic route of CTF-TPMs

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图 26 CTF和CTF-IM的合成工艺

Figure 26 Synthesis process of CTF and CTF-IM

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图 27 用1-氨基乙基-3-甲基咪唑溴化铵对ZIF-8 (x)进行合成后修饰

Figure 27 Postsynthetic modification of ZIF-8 (x) with 1-aminoethyl-3-methylimidazolium bromide

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图 28 ZIF-67或ZIF-67@CeO₂催化CO₂与SO环加成反应可能的协同催化过程

Figure 28 A possible synergistic catalytic process of CO₂ cycloaddition reaction with SO over ZIF-67 or over ZIF-67@CeO₂

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图 29 ML-ZIF的De novo 合成

Figure 29 De novo syntheses of ML-ZIFs

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图 30 胺官能化Co/Zn-ZIF-A材料的合成过程示意图

Figure 30 Schematic illustration of the synthesis procedure of amine-functionalized Co/Zn-ZIF-A materials

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图 31 双功能离子超交联聚合物的过程示意图

Figure 31 Schematic procedure of bifunctional ionic hyper-cross-linked polymers

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图 32 Py-HCP-X的制备方法

Figure 32 Preparation procedure for Py-HCP-X

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图 33 IHCPs的结构

Figure 33 The structure of IHCPs

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图 34 含单个钴位点的超薄CMP纳米片的制造示意图

Figure 34 Fabrication diagram of ultra-thin CMP nanosheets containing a single cobalt site

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图 35 （a）Zn-Salen-CMP和（b）CMP-Salen-Zn的结构

Figure 35 Structure of (a) Zn-Salen-CMP and (b) CMP-Salen-Zn

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图 36 PPh₂PStR-PMtVPP的合成路线^[123]

Figure 36 Schematic diagram of several porous organic polymers^[123] (with permission from RSC Publications)

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图 37 几种多孔有机聚合物的结构示意图

Figure 37 Schematic diagram of several porous organic polymers

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图 38 PIM2的合成路线

Figure 38 Synthetic route of PIM2

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图 39 IL-m、PIL-m和PIL-DVB-x的合成工艺

Figure 39 The synthesis process of IL-m, PIL-m and PIL-DVB-x

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图 40 制备PLMs的简单机理

Figure 40 The brief scheme for the preparation of PILMs

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图 41 功能阳离子PAMAM树枝状聚合物的合成路线^[136]

Figure 41 Synthetic route of functional cationic PAMAM dendrimer^[136] (with permission from Elesiver Publications)

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表 1 不同多相催化剂催化活性的比较

Table 1 Comparison of catalytic activity of different heterogeneous catalysts

Catalysts	Co-catalysts	Reaction conditions catalyst amount/epoxide amount （mmol）/temperature（℃）/CO₂ pressure（bar）/time（h）	Yield /%	References
Support Salophen-MnCl	TBAB	0.05 mmol/6.1 mmol/120/15/4	100	[77]
KIT-6@ILCH₃CH（OH）COO（0.6）	−	0.15 g/0.01/90/7/2	99	[78]
ZrO₂/g-C₃N₄−400	−	200 mg/16.6/140/20/6	69	[79]
Cu MOF	TBAB	0.5%/20/60/20/6	97	[85]
PMo12@Zr-FcMOF	TBAB	10.26%/12.5/80/1/8	86.77	[86]
Co(II)MOF	TBAB	15 mg/31/80/10/3	97	[87]
COF-SO₃H	TBAB	0.01 mmol/20/80/1/24	99	[89]
Zn@TpTta	TBAB	10 mmol/10/60/1/4	100	[90]
PIL-HPCOF	−	15 mg/5/90/10/24	99	[91]
2,5-DCP-CTF	−	100 mg/18/130/6.9/4	99.1	[93]
CTF-TPM-400	−	3%/10/100/7/24	99	[94]
CTF-IM	−	100 mg/35.7/120/20/2.5	94.6	[95]
IL-ZIF-8（0.3）	−	30 mg/25/110/10/4	97	[99]
ZIF-67@CeO₂	−	4.6%/-/120/7.5/8	100	[100]
ML-ZIF 5_Co	−	0.2%/-/120/14/0.5	94	[101]
Co/Zn-ZIF-A-24 h	−	50 mg/25/80/1/24	99	[102]
DHI-CSU-3-Br	TBAB	30 mg/3/70/1/4	99	[110]
Py-HCP-Br	−	0.4 g/34.5/120/20/4	97	[111]
IHCP-1	−	100 mg/10/140/10/24	99	[112]
DTBBQ-CMP	TBAB	5 mg/2/25/1/48	99	[115]
Zn-Salen-CMP	TBAB	0.1 mmol/50/120/30/1	90	[116]
CMP-Salen-Zn	TBAB	0.025 mmol/5/120/1/12	99	[117]
Co-PPOPs	−	20 mg/25/25/1/48	98	[122]
PPh₂PStR-PMtVPP	−	0.0424 mmol/20/80/48/1	98.9	[123]
COCP-OH	KI	71 mg/10/70/1/24	94.8	[124]
1D-UCP	KI	0.1 mmol/10/80/1/24	90.1	[125]
PMP-TDNs	−	61.3 mg/50/110/10/8	98.6	[126]
PIMBr-COOH	−	1%/43/100/1/6	94	[128]
PIP-urea		0.3%/10/100/10/5	93	[129]
H-MOP-BA	TBAI	1.25 mmol/4/50/10/24	96	[130]
PIM2	−	0.2%/10/130/10/4	92	[133]
PIL-DVB-IV	−	0.5 g/34.5/110/20/6	93	[134]
PILMs	−	0.319 mmol/28.6/110/25/3	87.3	[135]
[G₃−PAMAM-HADMAB-C₁₈]Br	−	0.3125%/50/110/10/3	94.9	[136]

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参考文献(137)

[1]	YANG Z Q, HE C Q, SUI H, He L, Li X A. Recent advances of CO₂-responsive materials in separations[J]. J CO₂ Util,2019,30:79−99. doi: 10.1016/j.jcou.2019.01.004
[2]	PARKINSON B, BALCOMBE P, SPEIRS J F, Hawkes A D, Hellgardt K. Levelized cost of CO₂ mitigation from hydrogen production routes[J]. Energy Environ Sci,2019,12(1):19−40. doi: 10.1039/C8EE02079E
[3]	FAJARDY M, MAC DOWELL N. The energy return on investment of BECCS: is BECCS a threat to energy security?[J]. Energy Environ Sci,2018,11(6):1581−1594. doi: 10.1039/C7EE03610H
[4]	SZIMA S, NAZIR S M, CLOETE S, Amini S, Fogarasi S, Cormos A M, Cormos C C. Gas switching reforming for flexible power and hydrogen production to balance variable renewables[J]. Renew Sustain Energy Rev,2019,110:207−219. doi: 10.1016/j.rser.2019.03.061
[5]	CHATTERJEE R, BHATTACHARJEE S, BHAUMIK A. Bifunctional metal-free heterogeneous catalyst for the synthesis of methanol and diols from CO₂ and Epoxide[J]. Asian J Org Chem,2022,11(9):e202200317.
[6]	LIU R, XU S, HAO G P, Lu A H. Recent advances of porous solids for ultradilute CO₂ capture[J]. Chem Res Chin Univ,2022,38(1):18−30. doi: 10.1007/s40242-021-1394-x
[7]	KHOO H H, BU J, WONG R L, Kuan S Y, Sharratt P N. Carbon capture and utilization: Preliminary life cycle CO₂, energy, and cost results of potential mineral carbonation[J]. Energy Procedia,2011,4:2494−2501. doi: 10.1016/j.egypro.2011.02.145
[8]	ALLURI S, CLAREMBOUX, V, KAWATRA S. Opportunities and challenges in CO₂ utilization[J]. J Environ Sci,2022,113:322−344. doi: 10.1016/j.jes.2021.05.043
[9]	CUÉLLAR-FRANCA R M, AZAPAGIC A. Carbon capture, storage and utilisation technologies: A critical analysis and comparison of their life cycle environmental impacts[J]. J CO₂ Util,2015,9:82−102. doi: 10.1016/j.jcou.2014.12.001
[10]	姜秀云, 杨文兵, 宋昊, 马清祥, 高新华, 李鹏, 赵天生. 甲酸辅助Cu-ZnO-Al₂O₃催化剂制备及其CO₂加氢制甲醇性能研究[J]. 燃料化学学报(中英文),2023,51(1):120−128. doi: 10.1016/S1872-5813(22)60041-0 JIANG Xiu-yun, YANG Wen-bing, SONG Hao, MA Qing-xiang, GAO Xin-hua, LI Peng, ZHAO Tian-sheng. Formic acid assisted synthesis of Cu-ZnO-Al₂O₃ catalyst and its performance in CO₂ hydrogenation to methanol[J]. J Fuel Chem Technol,2023,51(1):120−128. doi: 10.1016/S1872-5813(22)60041-0
[11]	周程, 南永永, 查飞, 田海锋, 唐小华, 常玥. 金属有机骨架材料在二氧化碳加氢中的应用[J]. 燃料化学学报(中英文),2021,49(10):1444−1457. doi: 10.1016/S1872-5813(21)60097-X ZHOU Cheng, NAN Yong-yong, ZHA Fei, TIAN Hai-feng, TANG Xiao-hua, CHANG Yue. Application of metal-organic frameworks in CO₂ hydrogenation[J]. J Fuel Chem Technol,2021,49(10):1444−1457. doi: 10.1016/S1872-5813(21)60097-X
[12]	毛瑀中, 查飞, 田海锋, 唐小华, 常玥, 郭效军. 热催化CO₂加氢制乙醇的研究进展[J]. 燃料化学学报(中英文),2023,51(5):1−15. MAO Yu-zhong, ZHA Fei, TIAN Hai-feng, TANG Xiao-hua, CHANG Yue, GUO Xiao-jun. Progress in thermal catalysis hydrogenation of CO₂ to ethanol[J]. J Fuel Chem Technol,2023,51(5):1−15.
[13]	LI G Q, DONG S, FU P, Yue Q H, Zhou Y, Wang J. Synthesis of porous poly(ionic liquid)s for chemical CO₂ fixation with epoxides[J]. Green Chem,2022,24(9):3433−3460. doi: 10.1039/D2GC00324D
[14]	LI N N, QIN S J, HAO Y J, Wang X L, CHANG T, LIU X H, ZHANG Y H, PANCHAL B, ZHU Z. Nanoarchitectonics of polymeric crown-ether analog of Tröger base combined with potassium iodide and acids synergy in fixation of CO₂ and epoxides[J]. Mol Catal,2023,545:113241. doi: 10.1016/j.mcat.2023.113241
[15]	KULAL N, VASISTA V, SHANBHAG G V. Identification and tuning of active sites in selected mixed metal oxide catalysts for cyclic carbonate synthesis from epoxides and CO₂[J]. J CO₂ Util,2019,33:434−444. doi: 10.1016/j.jcou.2019.07.018
[16]	GAO L Y, ZHOU Y, LI Z J, HE J, QU Y Y, ZOU X, LIU B, GUO K, MA C L, SUN J. Nicotinamide onium halide bidentate hybrid H-bond donor organocatalyst for CO₂ fixation[J]. J CO₂ Util,2022,65:102196. doi: 10.1016/j.jcou.2022.102196
[17]	SONG X H, WU Y F, PAN D H, WEI R, GAO L, ZHANG J, XIAO G. Melem based multifunctional catalyst for chemical fixation of carbon dioxide into cyclic carbonate[J]. J CO₂ Util,2018,24:287−297. doi: 10.1016/j.jcou.2018.01.017
[18]	KAMPHUIS A J, PICCHIONI F, PESCARMONA P P. CO₂-fixation into cyclic and polymeric carbonates: principles and applications[J]. Green Chem,2019,21(3):406−448. doi: 10.1039/C8GC03086C
[19]	LEU M K, VICENTE I, FERNANDES J A, De PEDRO I, DUPONT J, SANS V, LICENCE P, GUAL A, CANO I. On the real catalytically active species for CO₂ fixation into cyclic carbonates under near ambient conditions: Dissociation equilibrium of [BMIm][Fe(NO)₂Cl₂] dependant on reaction temperature[J]. Appl Catal B Environ,2019,245:240−250. doi: 10.1016/j.apcatb.2018.12.062
[20]	LIU J, YANG G Q, LIU Y, Zhang D, HU X, ZHANG Z. Efficient conversion of CO₂ into cyclic carbonates at room temperature catalyzed by Al-salen and imidazolium hydrogen carbonate ionic liquids[J]. Green Chem,2020,22(14):4509−4515. doi: 10.1039/D0GC00458H
[21]	REHMAN A, SALEEM F, JAVED F, IKHLAQ A, AHMAD S W, HARVEY A. Recent advances in the synthesis of cyclic carbonates via CO₂ cycloaddition to epoxides[J]. J Environ Chem Eng,2021,9(2):105113. doi: 10.1016/j.jece.2021.105113
[22]	LU Z, HE J, GUO B G, ZHAO Y, CAI J, XIAO L, HOU L. Efficient homogenous catalysis of CO₂ to generate cyclic carbonates by heterogeneous and recyclable polypyrazoles[J]. Chin J Chem Eng,2022,43:110−115. doi: 10.1016/j.cjche.2022.01.009
[23]	李东娜, 邱明月, 张奇日, 易群, 范海明, 李向远, 李剑川, 史利娟, 张鼎. 一步法构筑离子液体功能化MOF材料用于常压催化CO₂环加成反应[J]. 燃料化学学报(中英文),2022,50(7):824−831. doi: 10.1016/S1872-5813(21)60195-0 LI Dong-na, QIU Ming-yue, ZHANG Qi-ri, YI Qun, FAN Hai-ming, LI Xiang-yuan, LI Jian-chuan, SHI Li-juan, ZHANG Ding. One-pot construction of ionic liquid-functionalized MOF material as the catalyst for CO₂ cycloaddition under atmospheric pressure[J]. J Fuel Chem Technol,2022,50(7):824−831. doi: 10.1016/S1872-5813(21)60195-0
[24]	胡凤群, 邱明月, 易群, 张鼎, 李向远, 李剑川, 史利娟, 段小川. 核壳型MOFs@离子液体复合材料的制备及其常压下催化CO₂环加成反应性能探究[J]. 燃料化学学报(中英文)DOI: 10.19906/j.cnki.JFCT.2023028. HU Feng-qun, QIU Ming-yue, YI Qun, ZHANG Ding, LI Xiang-yuan, LI Jian-chuan, SHI Li-juan, DUAN Xiao-chuan. Construction of core-shell MOFs@ionic liquid materials and their performance for CO₂ cycloaddition reaction under atmospheric pressure[J]. J Fuel Chem Technol,DOI: 10.19906/j.cnki.JFCT.2023028
[25]	KEMBER M R, BUCHARD A, WILLIAMS C K. Catalysts for CO₂/epoxide copolymerisation[J]. Chem Commun,2011,47(1):141−163. doi: 10.1039/C0CC02207A
[26]	王献红, 王佛松. CO₂的固定和利用[M]. 北京: 化学工业出版社, 2011: 64. WANG Xian-hong, WANG Fo-song. CO₂ fixation and utilization[M]. Beijing: Chemical Industry Press, 2011: 64.
[27]	GUO L P, LAMB K J, NORTH M. Recent developments in organocatalysed transformations of epoxides and carbon dioxide into cyclic carbonates[J]. Green Chem,2021,23(1):77−118. doi: 10.1039/D0GC03465G
[28]	YUE S, WANG P, HAO X. Synthesis of cyclic carbonate from CO₂ and epoxide using bifunctional imidazolium ionic liquid under mild conditions[J]. Fuel,2019,251:233−241. doi: 10.1016/j.fuel.2019.04.039
[29]	MUJMULE R B, KIM H. Efficient imidazolium ionic liquid as a tri-functional robust catalyst for chemical fixation of CO₂ into cyclic carbonates[J]. J Environ Manage,2022,314:115045. doi: 10.1016/j.jenvman.2022.115045
[30]	ZHANG A, CHEN C J, ZUO C S, XU X, CAI T, Li X, YUAN Y, YANG H H, MENG G. Imidazolium-based ionic liquids containing multipoint hydrogen bond donors as bifunctional organocatalysts for efficient cooperative conversion of CO₂ to cyclic carbonates[J]. Green Chem,2022,24(18):7194−7207. doi: 10.1039/D2GC02517E
[31]	de ALMEIDA BEZERRA W, MILANI J L S, de JESUS FRANCO C H, MARTINS F T, de FÁCTIMA Â, da MATA Á F A, das CHAGAS R P. Bis-benzimidazolium salts as bifunctional organocatalysts for the cycloaddition of CO₂ with epoxides[J]. Mol Catal,2022,530:112632. doi: 10.1016/j.mcat.2022.112632
[32]	CHENG W G, XIAO B N, SUN J, DONG K, ZHANG P, ZHANG S J, NG F T T. Effect of hydrogen bond of hydroxyl-functionalized ammonium ionic liquids on cycloaddition of CO₂[J]. Tetrahedron Lett,2015,56(11):1416−1419. doi: 10.1016/j.tetlet.2015.01.174
[33]	PENG J, WANG S, YANG H J, BAN B, WEI Z D, WANG L H, LEI B. Highly efficient fixation of carbon dioxide to cyclic carbonates with new multi-hydroxyl bis-(quaternary ammonium) ionic liquids as metal-free catalysts under mild conditions[J]. Fuel,2018,224:481−488. doi: 10.1016/j.fuel.2018.03.119
[34]	BÜTTNER H, STEINBAUER J, WULF C, Dindaroglu M, SCHMALZ H G, WERNER T. Organocatalyzed synthesis of oleochemical carbonates from CO₂ and renewables[J]. ChemSusChem,2017,10(6):1076−1079. doi: 10.1002/cssc.201601163
[35]	LIU Y, CHENG W G, ZHANG Y Q, SUN J, ZHANG S. Controllable preparation of phosphonium-based polymeric ionic liquids as highly selective nanocatalysts for the chemical conversion of CO₂ with epoxides[J]. Green Chem,2017,19(9):2184−2193. doi: 10.1039/C7GC00444C
[36]	SHAIKH A C, VELETA J M, BLOCH J, GOODMAN H J, GIANETTI T L. Syntheses of phosphonium salts from phosphines and carbenium: efficient CO₂ fixation and phase-transfer catalysts[J]. Eur J Org Chem,2020,2020(17):2553−2559. doi: 10.1002/ejoc.202000221
[37]	ZHANG Z G, FAN F J, XING H B, YANG Q, BAO Z, REN Q. Efficient synthesis of cyclic carbonates from atmospheric CO₂ using a positive charge delocalized ionic liquid catalyst[J]. ACS Sustainable Chem Eng,2017,5(4):2841−2846. doi: 10.1021/acssuschemeng.7b00513
[38]	ROSTAMI A, MAHMOODABADI M, HOSSEIN E A, KHOSRAVI H, Al-HARRASI A. An electrostatically enhanced phenol as a simple and efficient bifunctional organocatalyst for carbon dioxide fixation[J]. ChemSusChem,2018,11(24):4262−4268. doi: 10.1002/cssc.201802028
[39]	NOROUZI F, ABDOLMALEKI A. CO₂ conversion into carbonate using pyridinium-based ionic liquids under mild conditions[J]. Fuel,2023,334:126641. doi: 10.1016/j.fuel.2022.126641
[40]	LI W, CHENG W G, YANG X, Su Q, DONG L, ZHANG P, YI Y N, LI B, ZHANG S J. Synthesis of cyclic carbonate catalyzed by DBU derived basic ionic liquids[J]. Chin J Chem,2018,36(4):293−298. doi: 10.1002/cjoc.201700747
[41]	FANJUL-MOSTEIRÍN N, JEHANNO C, RUIPÉREZ F, SARDON H, DOVE A P. Rational study of DBU salts for the CO₂ insertion into epoxides for the synthesis of cyclic carbonates[J]. ACS Sustainable Chem Eng,2019,7(12):10633−10640. doi: 10.1021/acssuschemeng.9b01300
[42]	CHOWDHURY B, ZVINCHUK A A, AYSIN R R, KHAKINA E A, CHERKASOVA P V, LYUBIMOV S E. Amine-Iodine Adducts as Simple but Effective Catalysts for the Synthesis of Organic Carbonates from Epoxides and CO₂[J]. Catal Surv Asia,2021,25(4):419−423. doi: 10.1007/s10563-021-09341-9
[43]	HE L, ZHANG W W, YANG Y F, MA J, LIU F, Liu M. Novel biomass-derived deep eutectic solvents promoted cycloaddition of CO₂ with epoxides under mild and additive-free conditions[J]. J CO₂ Util,2021,54:101750. doi: 10.1016/j.jcou.2021.101750
[44]	YANG X Q, ZOU Q Z, ZHAO T X, CHEN P, LIU Z, LIU F, LIN Q. Deep eutectic solvents as efficient catalysts for fixation of CO₂ to cyclic carbonates at ambient temperature and pressure through synergetic catalysis[J]. ACS Sustainable Chem Eng,2021,9(31):10437−10443. doi: 10.1021/acssuschemeng.1c03187
[45]	SHENG T, OU J L, ZHAO T X, YANG X Q, PENG Y X. Efficient fixation of CO₂ into cyclic carbonate catalyzed by choline bromide/imidazole derivatives-based deep eutectic solvents[J]. Mol Catal,2023,536:112907. doi: 10.1016/j.mcat.2022.112907
[46]	NG C K, TOH R W, LIN T T, LUO H K, HOR T A, WU J. Metal-salen molecular cages as efficient and recyclable heterogeneous catalysts for cycloaddition of CO₂ with epoxides under ambient conditions[J]. Chem Sci,2019,10(5):1549−1554. doi: 10.1039/C8SC05019H
[47]	CASTRO-OSMA J A, LAMB K J, NORTH M. Cr (salophen) complex catalyzed cyclic carbonate synthesis at ambient temperature and pressure[J]. ACS Catal,2016,6(8):5012−5025. doi: 10.1021/acscatal.6b01386
[48]	DELLA MONICA F, CAPACCHIONE C. Recent advancements in metal-catalysts design for CO₂/epoxide reactions[J]. Asian J Org Chem,2022,11(8):e202200300.
[49]	AOMCHAD V, Del GOBBO S, YINGCHAROEN P, POATER A, D’Elia V. Exploring the potential of group III salen complexes for the conversion of CO₂ under ambient conditions[J]. Catal Today,2021,375:324−334. doi: 10.1016/j.cattod.2020.01.021
[50]	KUZNETSOVA S A, GORODISHCH I V, GAK A S. Chiral titanium(IV) and vanadium(V) salen complexes as catalysts for carbon dioxide and epoxide coupling reactions[J]. Tetrahedron,2021,82:131929. doi: 10.1016/j.tet.2021.131929
[51]	KIRIRATNIKOM J, LAIWATTANAPAISARN N, VONGNAM K, THAVORNSIN N, SAE-UNG P, KAEOTHIP S, EUAPERMKIATI A, NAMUANGRUK S, PHOMPHRAI K. Highly active chromium complexes supported by constrained schiff-base ligands for cycloaddition of carbon dioxide to epoxides[J]. Inorg Chem,2021,60(9):6147−6151. doi: 10.1021/acs.inorgchem.0c03732
[52]	KANG Y R, WANG B N, NAN R X, Li Y, Zhu Z, Xiao X Q. Cyclic carbonate synthesis from epoxides and CO₂ catalyzed by aluminum-salen complexes bearing a nido-C₂B₉ carborane ligand[J]. Inorg Chem,2022,61(23):8806−8814. doi: 10.1021/acs.inorgchem.2c00797
[53]	CONTENTO I, LAMPARELLI D H, BUONERBA A, GRASSI A, CAPACCHIONE C. New dinuclear chromium complexes supported by thioether-triphenolate ligands as active catalysts for the cycloaddition of CO₂ to epoxides[J]. J CO₂ Util,2022,66:102276. doi: 10.1016/j.jcou.2022.102276
[54]	NORTH M, QUEK S C Z, PRIDMORE N E, WHITWOOD A C, WU X. Aluminum (salen) complexes as catalysts for the kinetic resolution of terminal epoxides via CO₂ coupling[J]. ACS Catal,2015,5(6):3398−3402. doi: 10.1021/acscatal.5b00235
[55]	SU Y C, TSUI C H, TSAI C Y, KO B T. Highly active bimetallic nickel catalysts for alternating copolymerization of carbon dioxide with epoxides[J]. Polym Chem,2020,11(18):3225−3236. doi: 10.1039/D0PY00174K
[56]	DEACY A C, MOREBY E, PHANOPOULOS A, WILLIAMS C K. Co(III)/alkali-metal(I) heterodinuclear catalysts for the ring-opening copolymerization of CO₂ and propylene oxide[J]. J Am Chem Soc,2020,142(45):19150−19160. doi: 10.1021/jacs.0c07980
[57]	CHEN J, WU X M, DING H N, LIU N, LIU B, HE L. Tolerant bimetallic macrocyclic -type zinc complexes for efficient CO₂ fixation into cyclic carbonates[J]. ACS Sustainable Chem. Eng,2021,9(48):16210−16219. doi: 10.1021/acssuschemeng.1c05469
[58]	MAEDA C, SHIMONISHI J, MIYAZAKI R, HASEGAWA J Y, EMA T. Highly active and robust metalloporphyrin catalysts for the synthesis of cyclic carbonates from a broad range of epoxides and carbon dioxide[J]. Chem-Eur J,2016,22(19):6556−6563. doi: 10.1002/chem.201600164
[59]	MILANI J L S, MEIRELES A M, CABRAL B N, de ALMEIDA BEZERRA W, MARTINS F T, da SILVA MARTINS D C, das CHAGAS R P. Highly active Mn(III) meso-tetrakis(2, 3-dichlorophenyl) porphyrin catalysts for the cycloaddition of CO₂ with epoxides[J]. J CO₂ Util,2019,30:100−106. doi: 10.1016/j.jcou.2018.12.017
[60]	SCHOEPFF L, MONNEREAU L, DUROT S, JENNI S, GOURLAOUEN C, HEITZ V. A flexible bis-Co(III) porphyrin cage as a bimetallic catalyst for the conversion of CO₂ and epoxides into cyclic carbonates[J]. ChemCatChem,2020,12(22):101635.
[61]	LEAL J P S C, BEZERRA W A, CHAGAS R P, FRANCO C H, MARTINS F T, MEIRELES A M, ANTONIO F C T, HOMEM-de-MELLO P, TASSO T T, MILANI J L S. Metal–cocatalyst interaction governs the catalytic activity of MII-Porphyrazines for chemical fixation of CO₂[J]. Inorg Chem,2021,60(16):12263−12273. doi: 10.1021/acs.inorgchem.1c01462
[62]	MARTÍNEZ J, de la CRUZ-MARTÍNEZ F, GAONA M A, PINILLA-PENALVER E, FERNANDEZ-BAEZA J, RODRÍGUEZ A M, CASTRO-OSMA J A, OTERO A, LARA-SANCHEZ A. Influence of the counterion on the synthesis of cyclic carbonates catalyzed by bifunctional aluminum complexes[J]. Inorg Chem,2019,58(5):3396−3408. doi: 10.1021/acs.inorgchem.8b03475
[63]	PANZA N, BIASE A, GALLO E, PANZA N, di BIASE A, GALLO E, CASELLI A. Unexpected “ferrate” species as single-component catalyst for the cycloaddition of CO₂ to epoxides[J]. J CO₂ Util,2021,51:101635. doi: 10.1016/j.jcou.2021.101635
[64]	KIM J H, LEE S H, KIM N H, KANG E J. Sustainable synthesis of five-membered heterocycles using carbon dioxide and Fe-iminopyridine catalysts[J]. J CO₂ Util,2021,50:101595. doi: 10.1016/j.jcou.2021.101595
[65]	MILOCCO F, CHIARIONI G, PESCARMONA P P. Heterogeneous catalysts for the conversion of CO₂ into cyclic and polymeric carbonates[M]. Catalysis for Enabling Carbon Dioxide Utilization. ACADEMIC PRESS INC ELSEVIER SCIENCE, 2022: 151–187.
[66]	DU Y, CAI F, KONG D L, HE L N. Organic solvent-free process for the synthesis of propylene carbonate from supercritical carbon dioxide and propylene oxide catalyzed by insoluble ion exchange resins[J]. Green Chem,2005,7(7):518−523. doi: 10.1039/b500074b
[67]	ZHANG Q, ZHANG S B, LI S H. Novel functional organic network containing quaternary phosphonium and tertiary phosphorus[J]. Macromol,2012,45(7):2981−2988. doi: 10.1021/ma300278d
[68]	GHAZALI-ESFAHANI S, SONG H B, PĂUNESCU E, BOBBINK F D, LIU H Z, FEI Z F, LAURENCZY G, BAGHERZADEH M, YAN N, DYSO P J. Cycloaddition of CO₂ to epoxides catalyzed by imidazolium-based polymeric ionic liquids[J]. Green Chem,2013,15(6):1584−1589. doi: 10.1039/c3gc37085b
[69]	HAN L, PARK S W, PARK D W. Silica grafted imidazolium-based ionic liquids: efficient heterogeneous catalysts for chemical fixation of CO₂ to a cyclic carbonate[J]. Energy Environ Sci,2009,2(12):1286−1292. doi: 10.1039/b910763k
[70]	XIE Y, ZHANG Z F, JIANG T, HE J, HAN B, WU T, DING K. CO₂ cycloaddition reactions catalyzed by an ionic liquid grafted onto a highly crosslinked polymer matrix[J]. Angew Chem Int Ed,2007,46(38):7255−7258. doi: 10.1002/anie.200701467
[71]	APRILE C, GIACALONE F, AGRIGENTO P, LIOTTA L F, MARTENS J A, PESCARMONA P P, GRUTTADAURIA, M. Multilayered supported ionic liquids as catalysts for chemical fixation of carbon dioxide: a high-throughput study in supercritical conditions[J]. ChemSusChem,2011,4(12):1830−1837. doi: 10.1002/cssc.201100446
[72]	CHANG T, LI X P, HAO Y J, KANG L W, TIAN T, FU X Y, ZHU Z, PANCHAL B, QIN S J. Pyrene-based ammonium bromides combined with g-C₃N₄ for the synergistically enhanced fixation reaction of CO₂ and epoxides[J]. RSC Adv,2021,11(48):30222−30228. doi: 10.1039/D1RA05328K
[73]	ZANDA N, SOBOLEWSKA A, ALZA E, KLEIJ A W, PERICAS M A. Organocatalytic and halide-free synthesis of glycerol carbonate under continuous flow[J]. ACS Sustainable Chem Eng,2021,9(12):4391−4397. doi: 10.1021/acssuschemeng.1c01060
[74]	BARBARINI A, MAGGI R, MAZZACANI A, MORI G, SARTORI G, SARTORIO R. Cycloaddition of CO₂ to epoxides over both homogeneous and silica-supported guanidine catalysts[J]. Tetrahedron Lett,2003,44(14):2931−2934. doi: 10.1016/S0040-4039(03)00424-6
[75]	UDAYAKUMAR S, LEE M K, SHIM H L, PARK S W, PARK D W. Imidazolium derivatives functionalized MCM-41 for catalytic conversion of carbon dioxide to cyclic carbonate[J]. Catal Commun,2009,10(5):659−664. doi: 10.1016/j.catcom.2008.11.017
[76]	CHENG W G, CHEN X, SUN J, WANG J, ZHANG S. SBA-15 supported triazolium-based ionic liquids as highly efficient and recyclable catalysts for fixation of CO₂ with epoxides[J]. Catal Today,2013,200:117−124. doi: 10.1016/j.cattod.2012.10.001
[77]	BALAS M, BEAUDOIN S, PROUST A, LAUNAY F, VILLANNEAU R. Advantages of covalent immobilization of metal‐salophen on amino-functionalized mesoporous silica in terms of recycling and catalytic activity for CO₂ cycloaddition onto epoxides[J]. Eur J Inorg Chem,2021,2021(16):1581−1591. doi: 10.1002/ejic.202100150
[78]	LIU Y, HU Y L. Novel and high efficient cycloaddition of CO₂ with epoxides to cyclic carbonates over reusable mesoporous KIT-6 supported imidazolium lactate catalyst[J]. Bull Chem Soc Ethiop,2022,36(2):433−450. doi: 10.4314/bcse.v36i2.16
[79]	LIU N, WU F, XU J, XUE B, LUO J. ZrO₂ supported on graphitic carbon nitride based on metal–nitrogen interaction for enhanced catalytic cycloaddition of CO₂ to cyclic carbonates[J]. Catal Lett,2023,153(5):1483−1494. doi: 10.1007/s10562-022-04083-3
[80]	HE H M, PERMAN J A, ZHU G S, MA S. Metal-organic frameworks for CO₂ chemical transformations[J]. Small,2016,12(46):6309−6324. doi: 10.1002/smll.201602711
[81]	LIANG J, HUANG Y B, CAO R. Metal–organic frameworks and porous organic polymers for sustainable fixation of carbon dioxide into cyclic carbonates[J]. Coord Chem Rev,2019,378:32−65. doi: 10.1016/j.ccr.2017.11.013
[82]	PAL T K, DE D, BHARADWAJ P K C. Metal–organic frameworks for the chemical fixation of CO₂ into cyclic carbonates[J]. Coord Chem Rev,2020,408:213173. doi: 10.1016/j.ccr.2019.213173
[83]	SONG X J, WANG J, YANG L B, Pan H Y, Zheng B. The transformation strategies between homogeneous and heterogeneous catalysts for the coupling reactions of CO₂ and epoxides/olefins[J]. Inorg Chem Commun,2020,121:108197. doi: 10.1016/j.inoche.2020.108197
[84]	QI X P, CHANG T, ZHU Z, HAO Y J, LIU Y F, HOU J. Post-synthetic modification of Isomorphic coordination polymers with metal ion exchange and catalytic cycloaddition of CO₂[J]. J Solid State Chem,2021,304:122604. doi: 10.1016/j.jssc.2021.122604
[85]	ZHU Y Y, GU J M, YU X Y, ZHANG B R, LI G H, LI J T, LIU Y L. The multifunctional design of metal–organic framework by applying linker desymmetrization strategy: synergistic catalysis for high CO₂-epoxide conversion[J]. Inorg Chem Front,2021,8(23):4990−4997. doi: 10.1039/D1QI00960E
[86]	FANG Z, DENG Z, WAN X Y, LI Z Y, MA X, HUSSAIN S, YE Z Z, PENG X S. Keggin-type polyoxometalates molecularly loaded in Zr-ferrocene metal organic framework nanosheets for solar-driven CO₂ cycloaddition[J]. Appl Catal B:Environ,2021,296:120329. doi: 10.1016/j.apcatb.2021.120329
[87]	ULLAH N, RAMIERE A, RAZA W, YE P F, LIU W, CAI X K, PENG Z C, KIM K H. Cobalt-based MOF nanoribbons with abundant O/N species for cycloaddition of carbon dioxide to epoxides[J]. J Colloid Interf Sci,2022,623:752−761. doi: 10.1016/j.jcis.2022.05.082
[88]	DALIRAN S, OVEISI A R, PENG Y, LOPEZ-MAGANO A, KHAJEH M, MAS-BALLESTE R, ALEMAN J, LUQUE R, GARCIA H. Metal-organic-framework (MOF), covalent-organic-framework (COF), and porous-organic-polymers (POP) catalyzed selective C–H bond activation and functionalization reactions[J]. Chem Soc Rev,2022,51(18):7810−7882. doi: 10.1039/D1CS00976A
[89]	SINGH G, NAGARAJA C M. Highly efficient metal/solvent-free chemical fixation of CO₂ at atmospheric pressure conditions using functionalized porous covalent organic frameworks[J]. J CO₂ Util,2021,53:101716. doi: 10.1016/j.jcou.2021.101716
[90]	SARKAR S, GHOSH S, ISLAM S M. A Zn (ii)-functionalized COF as a recyclable catalyst for the sustainable synthesis of cyclic carbonates and cyclic carbamates from atmospheric CO₂[J]. Org Biomol Chem,2022,20(8):1707−1722. doi: 10.1039/D1OB01938D
[91]	DU Y R, YANG X, WANG Y F, GUAN P X, WANG R, XU B H. Immobilization poly(ionic liquid)s into hierarchical porous covalent organic frameworks as heterogeneous catalyst for cycloaddition of CO₂ with epoxides[J]. Mol Catal,2022,520:112164. doi: 10.1016/j.mcat.2022.112164
[92]	LUO R C, XU W, CHEN M, LIU X Y, FANG Y X, JI H B. Covalent triazine frameworks obtained from nitrile monomers for sustainable CO₂ catalysis[J]. ChemSusChem,2020,13(24):6509−6522. doi: 10.1002/cssc.202002422
[93]	LI Y M, YANG L, SUN L, MA L, DENG W Q, LI Z. Chemical fixation of carbon dioxide catalyzed via covalent triazine frameworks as metal free heterogeneous catalysts without a cocatalyst[J]. J Mater Chem A,2019,7(45):26071−26076. doi: 10.1039/C9TA07266G
[94]	ZHAO Y L, HUANG H L, ZHU H, ZHONG C L. Design and synthesis of novel pyridine-rich cationic covalent triazine framework for CO₂ capture and conversion[J]. Micropor Mesopor Mater,2022,329:111526. doi: 10.1016/j.micromeso.2021.111526
[95]	DAI W L, LI Q, LONG J F, MAO P, XU Y, YANG L X, ZHOU J P, LUO X B. Hierarchically mesoporous imidazole-functionalized covalent triazine framework: An efficient metal-and halogen-free heterogeneous catalyst towards the cycloaddition of CO₂ with epoxides[J]. J CO₂ Util,2022,62:102101. doi: 10.1016/j.jcou.2022.102101
[96]	HWANG G Y, ROSHAN R, RYU H S, JEONG H M, RAVI S, KIM M I, PARK D W. A highly efficient zeolitic imidazolate framework catalyst for the co-catalyst and solvent free synthesis of cyclic carbonates from CO₂[J]. J CO₂ Util,2016,15:123−130. doi: 10.1016/j.jcou.2016.02.005
[97]	KURUPPATHPARAMBIL R R, BABU R, JEONG H M, HWANG G Y, JEONG G S, KIM M I, KIM D W, PARK D W. A solid solution zeolitic imidazolate framework as a room temperature efficient catalyst for the chemical fixation of CO₂[J]. Green Chem,2016,18(23):6349−6356. doi: 10.1039/C6GC01614F
[98]	MARCINIAK A A, LAMB K J, OZORIO L P, MOTA C J. A, NORTH M. Heterogeneous catalysts for cyclic carbonate synthesis from carbon dioxide and epoxides[J]. Curr Opin Green Sustain Chem,2020,26:100365. doi: 10.1016/j.cogsc.2020.100365
[99]	XIANG W L, SHEN C Y, LU Z, CHEN S, LI X, ZOU R, ZHANG Y P, Liu C J. CO₂ cycloaddition over ionic liquid immobilized hybrid zeolitic imidazolate frameworks: Effect of Lewis acid/base sites[J]. Chem Eng Sci,2021,233:116429. doi: 10.1016/j.ces.2020.116429
[100]	HU L H, MO X H, CHEN L, WU Y H, LIU F, YIN K L, FAN T T, YAN Z C. Core-Shell ZIF-67@ CeO₂ Nanosphere as efficient acid‐base catalyst for the cycloaddition of CO₂ and epoxides[J]. ChemistrySelect,2022,7(20):e202200823.
[101]	ABRAHA Y W, TSAI C W, LANGNER E H G. De novo syntheses of multi-linker Zn-and Co-based ZIFs with application in CO₂ fixation[J]. Micropor Mesopor Mater,2022,346:112319. doi: 10.1016/j.micromeso.2022.112319
[102]	NGUYEN Q T, DO X H, CHO K Y, LEE Y R, BAEK K Y. Amine-functionalized bimetallic Co/Zn-zeolitic imidazolate frameworks as an efficient catalyst for the CO₂ cycloaddition to epoxides under mild conditions[J]. J CO₂ Util,2022,61:102061. doi: 10.1016/j.jcou.2022.102061
[103]	DU J, OUYANG H, TAN B. Porous Organic Polymers for Catalytic Conversion of Carbon Dioxide[J]. Chem Asian J,2021,16(23):3833−3850. doi: 10.1002/asia.202100991
[104]	ZHANG J S, QIAO Z A, MAHURIN S M, JIANG X, CHAI S H, LU H F, NELSON K, DAI S. Hypercrosslinked phenolic polymers with well‐developed mesoporous frameworks[J]. Angew Chem Int Ed,2015,54(15):4582−4586. doi: 10.1002/anie.201500305
[105]	XU S J, LUO Y L, TAN B. Recent development of hypercrosslinked microporous organic polymers[J]. Macromol Rap Commun,2013,34(6):471−484. doi: 10.1002/marc.201200788
[106]	LIANG J, CHEN R P, WANG X Y, LIU T T, WANG X S, HUANG Y B, CAO R. Postsynthetic ionization of an imidazole-containing metal-organic framework for the cycloaddition of carbon dioxide and epoxides[J]. Chem Sci,2017,8(2):1570−1575. doi: 10.1039/C6SC04357G
[107]	HOU S S, RAZZAQUE S, TAN B. Effects of synthesis methodology on microporous organic hyper-cross-linked polymers with respect to structural porosity, gas uptake performance and fluorescence properties[J]. Poly Chem,2019,10(11):1299−1311. doi: 10.1039/C8PY01730A
[108]	FU Z Y, JIA J Z, LI J, LIU C K. Transforming waste expanded polystyrene foam into hyper-crosslinked polymers for carbon dioxide capture and separation[J]. Chem Eng J,2017,323:557−564. doi: 10.1016/j.cej.2017.04.090
[109]	PENG R X, CHEN G, ZHOU F, MAN R L, HUANG J H. Catalyst-free synthesis of triazine-based porous organic polymers for Hg^{2 +} adsorptive removal from aqueous solution[J]. Chem Eng J,2019,371:260−266. doi: 10.1016/j.cej.2019.04.063
[110]	SANG Y F, SHU Z, WANG Y, WANG L Z, ZHANG D, XIAO Q, ZHOU F, HUANG J H. Bifunctional ionic hyper-cross-linked polymers for CO₂ capture and catalytic conversion[J]. Appl Surf Sci,2022,585:152663. doi: 10.1016/j.apsusc.2022.152663
[111]	LIU C, SHI L, ZHANG J X, SUN J M. One-pot synthesis of pyridine-based ionic hyper-cross-linked polymers with hierarchical pores for efficient CO₂ capture and catalytic conversion[J]. Chem Eng J,2022,427:131633. doi: 10.1016/j.cej.2021.131633
[112]	GU J R, YUAN Y X, ZHAO T X, LIU F, XU Y, TAO D J. Ionic-containing hyper-crosslinked polymer: A promising bifunctional material for CO₂ capture and conversion[J]. Sep Purif Technol,2022,301:121971. doi: 10.1016/j.seppur.2022.121971
[113]	GAO R D, ZHANG G, LU F L, CHEN L, LI Y. Pyrrole-based conjugated microporous polymers as efficient heterogeneous catalysts for knoevenagel condensation[J]. Front Chem,2021,9:687183. doi: 10.3389/fchem.2021.687183
[114]	DONG X Z, HUI Y H, XIE S L, ZHANG P, ZHOU G P, XIE Z F. Schiff base supported MCM-41 catalyzed the Knoevenagel condensation in water[J]. RSC Adv,2013,3(10):3222−3226. doi: 10.1039/c3ra00138e
[115]	ZHANG X F, LIU H, AN P F, SHI Y A, HAN J Y, YANG Z J, LONG C, GUO J, ZHAO S L, TANG Z Y. Delocalized electron effect on single metal sites in ultrathin conjugated microporous polymer nanosheets for boosting CO₂ cycloaddition[J]. Sci Adv,2020,6(17):eaaz4824. doi: 10.1126/sciadv.aaz4824
[116]	BHUNIA S, MOLLA R A, KUMARI V, ISLAM S M, BHAUMIK A. Zn (ii) assisted synthesis of porous salen as an efficient heterogeneous scaffold for capture and conversion of CO₂[J]. Chem Commun,2015,51(86):15732−15735. doi: 10.1039/C5CC06868A
[117]	ZHOU F Y, DENG Q W, HUANG N Y, ZHOU W, DENG W Q. CO₂ fixation into cyclic carbonates by a Zn-salen based conjugated microporous polymer[J]. ChemistrySelect,2020,5(34):10516−10520. doi: 10.1002/slct.202001538
[118]	JU P Y, QI W, GUO B X, LIU W T, WU Q L, SU Q. Highly stable and versatile conjugated microporous polymer for heterogeneous catalytic applications[J]. Catal Lett, 2023,https://doi.org/10.1007/s10562-022-04131-y.
[119]	LI H, LI C Z, CHEN J, LIU L N, YANG Q H. Synthesis of a pyridine–zinc‐based porous organic polymer for the Co-catalyst-free cycloaddition of epoxides[J]. Chem Asian J,2017,12(10):1095−1103. doi: 10.1002/asia.201700258
[120]	WANG W L, WANG Y Q, LI C Y, YAN L, JIANG M, DING Y J. State-of-the-art multifunctional heterogeneous POP catalyst for cooperative transformation of CO₂ to cyclic carbonates[J]. ACS Sustainable Chem Eng,2017,5(6):4523−4528. doi: 10.1021/acssuschemeng.7b00947
[121]	CHEN Y J, LUO R C, XU Q H, JIANG J, ZHOU X T, JI H B. Charged metalloporphyrin polymers for cooperative synthesis of cyclic carbonates from CO₂ under ambient conditions[J]. ChemSusChem,2017,10(11):2534−2541. doi: 10.1002/cssc.201700536
[122]	GUO D, LI C, ZHANG J, LIU G Y, LUO X G. Metalloporphyrin-based porous organic polymer as an efficient catalyst for cycloaddition of epoxides and CO₂[J]. J Solid State Chem,2021,293:121770. doi: 10.1016/j.jssc.2020.121770
[123]	DAI Z F, WANG S T, ZHOU N, LIU Y X, XIONG Y B. Novel porous organic polymers functionalized by metalloporphyrin and phosphonium salt for efficient synergistic catalysis of CO₂ conversion under mild conditions[J]. New J Chem,2022,46(46):22151−22161. doi: 10.1039/D2NJ04210J
[124]	HAO Y J, YAN X L, CHANG T, LIU X H, KANG L W, ZHU Z, PANCHAL B, QIN S J. Hydroxyl-anchored covalent organic crown-based polymers for CO₂ fixation into cyclic carbonates under mild conditions[J]. Sustain Energy Fuels,2022,6(1):121−127. doi: 10.1039/D1SE01120K
[125]	HAO Y J, YAN X L, LIU X H, QIN S J, ZHU Z, PANCHAL B, CHANG T. Urea-based covalent organic crown polymers and KI electrostatic synergy in CO₂ fixation reaction: A combined experimental and theoretical study[J]. J CO₂ Util,2022,56:101867. doi: 10.1016/j.jcou.2021.101867
[126]	YUE Z X, HU T D, ZHAO W B, SU H Y, LI W L, CHEN Z W, CHEN Y, LI S J, WANG L H, LIU Y, ZHANG H, SHAN S Y, ZHI Y F. Triazinyl-imidazole polyamide network as an efficient multi-hydrogen bond donor catalyst for additive-free CO₂ cycloaddition[J]. Appl Catal A:Gen,2022,643:118748. doi: 10.1016/j.apcata.2022.118748
[127]	QIU Y J, CHEN Y J, LEI L, WANG X L, ZENG X J, FENG Z F, DENG C Y, LIN D Y, JI H B. Bottom-up oriented synthesis of metalloporphyrin-based porous ionic polymers for the cycloaddition of CO₂ to epoxides[J]. Mol Catal,2022,521:112171. doi: 10.1016/j.mcat.2022.112171
[128]	CHEN Y, LI Y J, WANG H, CHEN Z F, LEI Y Z. Facile construction of carboxyl-functionalized ionic polymer towards synergistic catalytic cycloaddition of carbon dioxide into cyclic carbonates[J]. Int J Mol Sci,2022,23(18):10879. doi: 10.3390/ijms231810879
[129]	WANG Y P, DUAN J X. Urea and thiourea-functionalized, pyridinium-based ionic polymers convert CO₂ to cyclic carbonate under mild conditions[J]. ACS Appl Polym Mater,2022,4(8):5851−5860. doi: 10.1021/acsapm.2c00734
[130]	BANG S, JANG J Y, KO Y J K, LEE S M, KIM H J, SON S U. Hydroboration of hollow microporous organic polymers: a promising postsynthetic modification method for functional materials[J]. ACS Macro Lett,2022,11(8):1034−1040. doi: 10.1021/acsmacrolett.2c00385
[131]	ZHANG J W, LI X P, ZHU Z, CHANG T, FU X Y, HAO Y J, MENG X C, PANCHAL B, QIN S J. Hydroxylamino-anchored poly(ionic liquid)s for CO₂ fixation into cyclic ccarbonates at mild conditions[J]. Adv Sustain Syst,2021,5(1):202000133.
[132]	WANG P, Lv Q, TAO Y J, CHENG L Y, LI R P, JIAO Y W, FANG C, LI H P, GENG C H, SUN C Y, DING J, WAN H, GUAN G F. One-pot efficient fixation of low-concentration CO₂ into cyclic carbonate by mesoporous pyridine-functionalized binuclear poly (ionic liquid)s[J]. Mol Catal,2023,544:113157. doi: 10.1016/j.mcat.2023.113157
[133]	WANG Y P, NIE J Q, LU C F, WANG F Y, MA C, CHEN Z X, YANG G C. Imidazolium-based polymeric ionic liquids for heterogeneous catalytic conversion of CO₂ into cyclic carbonates[J]. Micropor Mesopor Mater,2020,292:109751. doi: 10.1016/j.micromeso.2019.109751
[134]	DU H L, YE Y F, XU P, SUN J M. Experimental and theoretical study on dicationic imidazolium derived poly(ionic liquid)s for catalytic cycloaddition of CO₂-epoxide[J]. J CO₂ Util,2023,67:102325. doi: 10.1016/j.jcou.2022.102325
[135]	LIU Y F, DONG L, WANG Y C, SU Q, MENG Q H, CHENG W G. Polymeric ionic liquid membranes for the absorption-conversion of CO₂ and epoxides into cyclic carbonates[J]. Mol Catal,2022,530:112597. doi: 10.1016/j.mcat.2022.112597
[136]	CHANG T, YAN X L, LI Y, HAO Y J, FU X Y, LIU X H, PANCHAL B, QIN S J, ZHU Z. Quaternary ammonium immobilized PAMAM as efficient catalysts for conversion of carbon dioxide[J]. J CO₂ Util,2022,58:101913. doi: 10.1016/j.jcou.2022.101913
[137]	YAN T, LIU H, ZENG Z X, PAN W G. Recent progress of catalysts for synthesis of cyclic carbonates from CO₂ and epoxides[J]. J CO₂ Util,2023,68:102355. doi: 10.1016/j.jcou.2022.102355