Poly(ionic liquid) materials tailored by carboxyl groups for the gas phase-conversion of epoxide and CO2 into cyclic carbonates

Journal of CO2 Utilization - Tập 60 - Trang 101976 - 2022
Yichao Wang1,2, Yifan Liu2,3, Qian Su2,3, Yunong Li2,3, Lili Deng2, Li Dong2,3, Mengqian Fu2, Shuaifei Liu2, Weiguo Cheng2,3
1School of Chemical Engineering, Zhengzhou University, Zhengzhou, 450001, China
2CAS Key Laboratory of Green Process and Engineering, State Key Laboratory of Multiphase Complex Systems, Beijing Key Laboratory of Ionic Liquids Clean Process, Institute of Process Engineering, Chinese Academy of Sciences, Beijing, 100190, China
3Advanced Energy Science and Technology Guangdong Laboratory, Huizhou, Guangdong, 516003, China

Tài liệu tham khảo

Kho, 2017, A review on photo-thermal catalytic conversion of carbon dioxide, Green Energy Environ., 2, 204, 10.1016/j.gee.2017.06.003 Liu, 2020, Squaramide functionalized ionic liquids with well-designed structures: Highly-active and recyclable catalyst platform for promoting cycloaddition of CO2 to epoxides, J. CO2 Util., 37, 39, 10.1016/j.jcou.2019.11.028 Du, 2021, Construction of a PPIL@COF core–shell composite with enhanced catalytic activity for CO2 conversion, Green Chem., 23, 2411, 10.1039/D1GC00267H Mao, 2018, Polymer nanoparticles grafted zinc-containing ionic liquids: a highly efficient and recyclable catalyst for cooperative cycloaddition of CO2 with epoxides, J. CO2 Util., 28, 96, 10.1016/j.jcou.2018.09.017 Zhang, 2020, Recent advances in the coupling of CO2 and epoxides into cyclic carbonates under halogen-free condition, Green Chem. Eng., 1, 82, 10.1016/j.gce.2020.09.008 Gou, 2021, Hydrogen bond donor functionalized poly(ionic liquid)s for efficient synergistic conversion of CO2 to cyclic carbonates, Phys. Chem. Chem. Phys., 23, 2005, 10.1039/D0CP06041K Ying, 2019, Polymeric ionic liquids tailored by different chain groups for the efficient conversion of CO2 into cyclic carbonates, Green Chem., 21, 2352, 10.1039/C9GC00010K Wu, 2021, Efficient fixation of CO2 into propylene carbonate with [BMIM]Br in a continuous-flow microreaction system, Green Energy Environ., 6, 291, 10.1016/j.gee.2020.04.016 Yu, 2021, Aliphatic polycarbonates from cyclic carbonate monomers and their application as biomaterials, Chem. Rev., 121, 10865, 10.1021/acs.chemrev.0c00883 Dai, 2009, The direct transformation of carbon dioxide to organic carbonates over heterogeneous catalysts, Appl. Catal. A Gen., 366, 2, 10.1016/j.apcata.2009.06.045 Yasuda, 2006, Non-halogen catalysts for propylene carbonate synthesis from CO2 under supercritical conditions, Appl. Catal. A Gen., 298, 177, 10.1016/j.apcata.2005.09.034 Takashi Yano, 1997, Magnesium oxide-catalysed reaction of carbon dioxide with an epoxide with retention of stereochemistry, Chem. Commun., 12, 1129, 10.1039/a608102i Sibaouih, 2009, Efficient coupling of CO2 and epoxides with bis(phenoxyiminato) cobalt(III)/Lewis base catalysts, J. Mol. Catal. A Chem., 312, 87, 10.1016/j.molcata.2009.07.009 Shaikh, 2017, Catalytic strategies for the cycloaddition of pure, diluted, and waste CO2 to epoxides under ambient conditions, ACS Catal., 8, 419, 10.1021/acscatal.7b03580 Li, 2019, Synthesis of covalent organic frameworks via in situ salen skeleton formation for catalytic applications, J. Mater. Chem. A, 7, 5482, 10.1039/C8TA11058A Zhu, 2018, A new class of metal-cyclam-based zirconium metal-organic frameworks for CO2 adsorption and chemical fixation, J. Am. Chem. Soc., 140, 993, 10.1021/jacs.7b10643 Srivastava, 2003, Synthesis of polycarbonate precursors over titanosilicate molecular sieves, Catal. Lett., 91, 133, 10.1023/B:CATL.0000006329.37210.fd Sun, 2009, Water as an efficient medium for the synthesis of cyclic carbonate, Tetrahedron Lett., 50, 423, 10.1016/j.tetlet.2008.11.034 Rogers, 2003, Chemistry. Ionic liquids--solvents of the future?, Science, 302, 792, 10.1126/science.1090313 Kim, 2003, Imidazolium zinc tetrahalide-catalyzed coupling reaction of CO2 and ethylene oxide or propylene oxide, J. Catal., 220, 44, 10.1016/S0021-9517(03)00238-0 Cheng, 2013, Ionic liquids: the synergistic catalytic effect in the synthesis of cyclic carbonates, Catalysts, 3, 878, 10.3390/catal3040878 Peng, 2001, Cycloaddition of carbon dioxide to propylene oxide catalyzed by ionic liquids, New J. Chem., 25, 639, 10.1039/b008923k Zhao, 2007, Quaternary ammonium salt-functionalized chitosan: an easily recyclable catalyst for efficient synthesis of cyclic carbonates from epoxides and carbon dioxide, J. Mol. Catal. A Chem., 271, 284, 10.1016/j.molcata.2007.03.047 Sun, 2014, Superbase/cellulose: an environmentally benign catalyst for chemical fixation of carbon dioxide into cyclic carbonates, Green Chem., 16, 6, 10.1039/c3gc41850b Sun, 2012, Chitosan functionalized ionic liquid as a recyclable biopolymer-supported catalyst for cycloaddition of CO2, Green Chem., 14, 10.1039/c2gc16335g Sun, 2009, Reusable and efficient polymer-supported task-specific ionic liquid catalyst for cycloaddition of epoxide with CO2, Catal. Today, 148, 361, 10.1016/j.cattod.2009.07.070 Chen, 2012, Polystyrene-bound diethanolamine based ionic liquids for chemical fixation of CO2, Tetrahedron Lett., 53, 2684, 10.1016/j.tetlet.2012.03.058 Su, 2018, Ionic liquids tailored and confined by one-step assembly with mesoporous silica for boosting the catalytic conversion of CO2 into cyclic carbonates, Green Chem., 20, 3232, 10.1039/C8GC01038B Sun, 2018, Facile approach to graft ionic liquid into MOF for improving the efficiency of CO2 chemical fixation, ACS Appl. Mater. Interfaces, 10, 27124, 10.1021/acsami.8b08914 Shi, 2013, Efficient fixation of CO2 into cyclic carbonates catalyzed by hydroxyl-functionalized poly(ionic liquids), RSC Adv., 3, 3726, 10.1039/c3ra21872d Meng, 2014, Functionalized dicyandiamide–formaldehyde polymers as efficient heterogeneous catalysts for conversion of CO2 into organic carbonates, Green Chem., 16, 2771, 10.1039/C3GC42331J Xie, 2007, CO2 cycloaddition reactions catalyzed by an ionic liquid grafted onto a highly cross-linked polymer matrix, Angew. Chem. Int. Ed., 46, 7255, 10.1002/anie.200701467 Puthiaraj, 2019, CO2 adsorption and conversion into cyclic carbonates over a porous ZnBr2-grafted N-heterocyclic carbene-based aromatic polymer, Appl. Catal. B Environ., 251, 195, 10.1016/j.apcatb.2019.03.076 Vara, 2015, Enantioselective small molecule synthesis by carbon dioxide fixation using a dual Bronsted acid/base organocatalyst, J. Chem. Soc., 137, 7302, 10.1021/jacs.5b04425 Jiang, 2018, Amino acid-paired dipyridine polymer as efficient metal- and halogen-free heterogeneous catalysts for cycloaddition of CO2 and epoxides into cyclic carbonates, Catal. Commun., 111, 1, 10.1016/j.catcom.2018.03.030 Sun, 2011, Efficient acid-base bifunctional catalysts for the fixation of CO(2) with epoxides under metal- and solvent-free conditions, ChemSusChem, 4, 502, 10.1002/cssc.201000305 Zhang, 2020, Poly(ionic liquid) composites, Chem. Soc. Rev., 49, 1726, 10.1039/C8CS00938D Cui, 2022, Environmentally friendly bark-derived Co-Doped porous carbon composites for microwave absorption, Carbon, 187, 115, 10.1016/j.carbon.2021.10.077 Ma, 2022, Facile fabrication of metal-organic framework derived Fe/Fe3O4/FeN/N-doped carbon composites coated with PPy for superior microwave absorption, J. Colloid Interface Sci., 608, 525, 10.1016/j.jcis.2021.09.169 Shi, 2022, Self-assembled lightweight three-dimensional hierarchically porous Ti3C2Tx MXene@polyaniline hybrids for superior microwave absorption, J. Alloy. Compd., 892, 10.1016/j.jallcom.2021.162194 Li, 2021, Novel anion exchange membrane with poly ionic liquid-confined hypercrosslinked polymer for enhanced anion conduction and stability, Int. J. Hydrog. Energy, 46, 21590, 10.1016/j.ijhydene.2021.03.223 Bernardo, 2011, Integrated membrane operations in the ethylene oxide production, Clean Technol. Environ. Policy, 14, 475, 10.1007/s10098-011-0434-5 Li, 2019, The counterion effect of imidazolium-type poly(ionic liquid) brushes on carbon dioxide adsorption, ChemPlusChem, 84, 281, 10.1002/cplu.201800636 Li, 2016, Microporous polyimides with functional groups for the adsorption of carbon dioxide and organic vapors, J. Mater. Chem. A, 4, 11453, 10.1039/C6TA04337B Zuo, 2016, Hydrogen bonding induced UCST phase transition of poly(ionic liquid)-based nanogels, Polymer, 98, 287, 10.1016/j.polymer.2016.06.048 Atkin, 2008, The smallest amphiphiles: Nanostructure in protic room-temperature ionic liquids with short alkyl groups, J. Phys. Chem. B, 112, 4164, 10.1021/jp801190u Chang, 2021, Regulation of novel multi-center ionic liquids for synergetically catalyzing CO2 conversion into cyclic carbonates, ChemistrySelect, 6, 6380, 10.1002/slct.202101172 Fei, 2004, Bronsted acidic ionic liquids and their zwitterions: synthesis, characterization and pKa determination, Chem. Eur. J., 10, 4886, 10.1002/chem.200400145 Han, 2011, Ionic liquids containing carboxyl acid moieties grafted onto silica: synthesis and application as heterogeneous catalysts for cycloaddition reactions of epoxide and carbon dioxide, Green Chem., 13, 4, 10.1039/c0gc00612b Wang, 2016, An efficient metal- and solvent-free organocatalytic system for chemical fixation of CO2 into cyclic carbonates under mild conditions, Green Chem., 18, 1229, 10.1039/C5GC02697K Shi, 2020, Ionic liquids with multiple active sites supported by SBA-15 for catalyzing conversion of CO2 into cyclic carbonates, J. CO2 Util., 39