离子液体催化二氧化碳合成环状碳酸酯的研究进展

doi:10.16085/j.issn.1000-6613.2017-0282

摘要/Abstract

摘要： 离子液体作为一种新型绿色环保介质，由于其结构可设计、稳定性高以及催化活性高等优点，使其在CO₂环加成反应的催化方面应用前景广阔。本文综述了近年来离子液体催化CO₂与环氧化物的环加成反应制备环状碳酸酯的研究进展。传统离子液体包括咪唑类、吡啶类、季铵盐季盐等离子液体，而功能化离子液体包括羟基功能化、羧基功能化等离子液体。与传统离子液体相比，功能化离子液体具有更好的催化活性。无机或有机材料负载的非均相离子液体催化剂报道较多，载体包括SiO₂、氧化石墨烯、聚合物等。非均相催化剂具备易分离、可在固定反应器中连续反应等优点，更适应工业化生产。指出了CO₂与环氧化合物反应制备环状碳酸酯过程中出现的催化剂活性低、反应条件苛刻等关键问题，因此寻求高选择性合成环状碳酸酯的环境友好的新型高效催化剂具有重要的学术意义和实用价值。

关键词: 二氧化碳, 环氧化合物, 环状碳酸酯, 离子液体

Abstract: As a novel environment friendly media,ionic liquids(ILs) have shown advantages in the catalysis of this cycloaddition reaction due to their structure designability,high stability,and high catalytic activity,etc.This review was mainly focus on the latest progress on the use of ILs as catalysts for the cycloaddition of CO₂ with epoxides. The conventional ILs contained imidazolium,pyridine,quaternary ammonium salt,quaternary phosphonium salts and other ILs. The functionalized ILs included hydroxyl-functionalized,carboxyl-functionalized and other ILs. Compared with conventional ILs,functionalized ILs had much better catalytic performance. A series of inorganic or organic support immobilizing ILs catalysts had been developed. Their supports included mesoporous silica,graphene oxide,polymers,etc. The chemical industry has always preferred to use a heterogeneous catalyst due to the ease of separation and the ability to use in a fixed-bed reactor. How to overcome the disadvantages of low activities,difficulties in separation and tough reaction conditions is a key issue. It is of great academic significance and practical value to pursue the new and efficient catalyst for high selectivity synthesis of cyclic carbonates.

Key words: carbon dioxide, epoxides, cyclic carbonates, ionic liquids

中图分类号:

O643.3

杨美, 钟向宏, 陈群. 离子液体催化二氧化碳合成环状碳酸酯的研究进展[J]. 化工进展, 2017, 36(09): 3300-3308.

YANG Mei, ZHONG Xianghong, CHEN Qun. Recent progress of the synthesis of cyclic carbonates from CO₂ and epoxides catalyzed by ionic liquids[J]. Chemical Industry and Engineering Progress, 2017, 36(09): 3300-3308.

参考文献

[1] 高志文,肖林飞,陈静,等. 二氧化碳与环氧化合物合成环状碳酸酯的研究进展[J]. 催化学报,2008,29(9):831-838. GAO Z F,XIAO L F,CHEN J,et al. Recent advances in the synthesis of cyclic carbonates from carbon dioxide and epoxides[J]. Chinese Journal of Catalysis,2008,29(9):831-838.
[2] HAIKAL R R,SOLIMAN A B,AMIN M,et al. Synergism of carbon nanotubes and porous-organic polymers (POPs) in CO₂ fixation:one-pot approach for bottom-up assembly of tunable heterogeneous catalyst[J]. Applied Catalysis B:Environmental,2017,207:347-357.
[3] FU X Y,ZHOU D G,WANG K,et al. Pd/C as a high efficient and reusable catalyst for cycloaddition of CO₂ to epoxides[J]. J. CO₂ Util.,2016,14:31-36.
[4] DAI W L,YANG W Y,ZHANG Y,et al. Novel isothiouronium ionic liquid as efficient catalysts for the synthesis of cyclic carbonates from CO₂ and epoxides[J]. J. CO₂ Util.,2017,17:256-262.
[5] SAKO T,FUKAI T,SAHASHI R. Cycloaddition of oxirane group with carbon dioxide in the supercritical homogeneous state[J]. Ind. Eng. Chem. Res.,2002,41(22):5353-5358.
[6] KAWANAMI H,IKUSHIMA Y. Chemical fixation of carbon dioxide to styrene carbonate under supercritical conditions with DMF in the absence of any additional catalysts[J]. Chem. Commun,2000,21:2089-2090.
[7] LAN D H,FAN N,WANG Y,et al. Recent advances in metal-free catalysts for the synthesis of cyclic carbonates from CO₂ and epoxides[J]. Chinese Journal of Catalysis,2016,37:826-845.
[8] DAI W L,YIN S F,GUO R,et al. Synthesis of propylene carbonate from carbon dioxide and propylene oxide using Zn-Mg-Al composite oxide as high-efficiency catalyst[J]. Catalysis Letters,2010,136(1/2):35-44.
[9] DOSKOCIL E J. Effect of water and alkali modifications on ETS-10 for the cycloaddition of CO₂ to propylene oxide[J]. J. Phys. Chem. B,2005,109(6):2315-2320.
[10] EFTEKHARI A,SAITO T. Synthesis and properties of polymerized ionic liquids[J]. European Polymer Journal,2017,90:245-272.
[11] SAPTAL V B,BHANAGE B M. Current advances in heterogeneous catalysts for the synthesis of cyclic carbonates from carbon dioxide[J]. Current Opinion in Green and Sustainable Chemistry,2017,3:1-10.
[12] XUE B,WU J,LIU N,et al. Facile immobilization of base ionic liquids onto grapheme oxidein water at room temperature as heterogeneous catalysts for transesterification[J]. Journal of Molecular Catalysis A:Chemical,2017,428:1-8.
[13] 毛信表,蔡萍萍,张寅旭,等. 离子液体中电活化CO₂合成有机碳酸酯的研究进展[J]. 化工进展,2015,34(3):825-830. MAO X B,CAI P P,ZHANG Y X,et al. Research progress in the electrochemical activation of CO₂ for the synthesis of organic carbonate in ionic liquid[J]. Chemical Industry and Engineering Progress,2015,34(3):825-830.
[14] 郭立颖,邓莉莉,马秀云,等. 离子液体多相催化二氧化碳与环氧化合物的研究进展[J]. 应用化工,2017,46(2):360-363. GUO L Y,DENG L L,MA X Y,et al. Research progress of heterogeneous catalytic the reaction of carbon dioxide with epoxides by ionic liquids[J]. Applied Chemical Industry,2017,46(2):360-363.
[15] BLANCHARD L A,HANCU D,BRENNEKE J F,et al. Green processing using ionic liquids and CO₂[J]. Nature,1999,399(6731):28-29.
[16] XIAO L F,SU D,YUE C T,et al. Protic ionic liquids:a highly efficient catalyst for synthesis of cyclic carbonate from carbon dioxide and epoxides[J]. J. CO₂ Util.,2014,6:1-6.
[17] 高歌,靳海波. 咪唑类离子液体催化合成碳酸丙烯酯[J]. 化学工业与工程,2014,31(1):14-18. GAO G,JIN H B. Synthesis of propylene carbonate in the presence of N-N'-dialkylimidazolium-based ionic liquids[J]. Chemical Industry and Engineering,2014,31(1):14-18.
[18] SHANNON M S,BARA J E. Properties of alkylimidazoles as solvents for CO₂ capture and comparisons to imidazolium-based ionic liquids[J]. Ind. Eng. Chem. Res.,2011,50(14):8665-8677.
[19] MANIC M S,QUEIMADA A J,MACEDO E A,et al. High-pressure solubilities of carbon dioxide in ionic liquids based on bis(trifluoromethylsulfonyl)imide and chloride[J]. Journal of Supercritical Fluids,2012,65(5):1-10.
[20] ANTHOFER M H,WILHELM M E,COLOJA M,et al. Cycloaddition of CO₂ and epoxides catalyzed by imidazolium bromides under mild conditions:influence of the cation on catalyst activity[J]. Catal. Sci. Technol.,2014,4(6):1749-1758.
[21] MAMONE M,MILCENT T,CROUSSE B. Reactivity of carbon dioxide in hydrofluoroethers:a facile access to cyclic carbonates[J]. Chem. Commum.,2015,51(64):12736-12739.
[22] 孟祥磊. 离子液体催化CO₂合成环状碳酸酯的研究[D].曲阜:曲阜师范大学,2014. MENG X L. The research of cyclic carbonate synthesis from CO₂ using ionic liquids[D]. Qufu:Qufu Normal University,2014.
[23] 梁栋,朱娜,陈小平,等. 烟碱离子液体的制备及在催化合成苯基环碳酸酯中的应用[J]. 烟草科技,2017,50(2):42-47. LIANG D,ZHU N,CHEN X P,et al. Preparation of nicotine ionic liquids and their application to catalytic synthesis of phenyl-substituted cyclic carbonate[J]. Tobacco Science & Technology,2017,50(2):42-47.
[24] WANG J Q,DONG K,CHENG W G,et al. Insights into quaternary ammonium salts-catalyzed fixation carbon dioxide with epoxides[J]. Catal. Sci. Technol.,2012,2(7):1480-1484.
[25] TODA Y,KOMIYAMA Y,KIKUCHI A,et al. Tetraarylphosphonium salt-catalyzed carbon dioxide fixation at atmospheric pressure for the synthesis of cyclic carbonates[J]. ACS Catal.,2016,6:6906-6910.
[26] DAI W L,JIN B,LUO S L,et al. Novel functionalized guanidinium ionic liquids:effcient acid-base bifunctional catalysts for CO₂ fixation with epoxides[J]. J. Mol. Catal. A:Chem.,2013,378(11):326-332.
[27] 郭立颖,马季云,王立岩,等. 氯化1-氨基聚醚-3-甲基咪唑离子液体的制备与催化性能[J]. 化工进展,2017,36(2):581-587. GUO L Y,MA J Y,WANG L Y,et al. Preparation and catalytic properties of chloride 1-amino polyether-3-methyl imidazole ionic liquid[J]. Chemical Industry and Engineering Progress,2017,36(2):581-587.
[28] LIU M S,LIU B,ZHONG S F,et al. Kinetics and mechanistic insight into efficient fixation of CO₂ to epoxides over N-heterocyclic compound/ZnBr₂ catalysts[J]. Ind. Eng. Chem. Res.,2015,54(2):633-640.
[29] LIU M S,WANG F X,SHI L,et al. Zn-based ionic liquids as highly efficient catalysts for chemical fixation of carbon dioxide to epoxides[J]. RSC Adv.,2015,46(27):14277-14284.
[30] DESENS W,KOHRT C,SPANNENBERG A,et al. A novel zinc based binary catalytic system for CO₂ utilization under mild conditions[J]. Org. Chem. Front,2016,3(2):156-164.
[31] WANG L,HUANG T F,CHEN C,et al. Mechanism of hexaalkylguanidinium salt/zinc bromide binary catalysts for the fixation of CO₂ with epoxide:a DFT investigation[J]. J. CO₂ Util.,2016,14:61-66.
[32] HUANG K,CHEN F F,TAO D J,et al. Ionic liquid-formulated hybrid solvents for CO₂ capture[J]. Current Opinion in Green and Sustainable Chemistry,2017,5:67-73.
[33] 张文林,张佳莉,靳斐,等. 离子液体及负载型钯催化剂在加氢反应中的研究进展[J]. 化工进展,2017,36(2):548-551. ZHANG W L,ZHANG J L,JIN F,et al. Progress of ionic liquids and supported palladium catalysts in the hydrogenation reactions[J]. Chemical Industry and Engineering Progress,2017,36(2):548-551.
[34] 杨刚胜,曾淦宁,赵强,等. 负载型氨基酸离子液体的制备及其对二氧化碳的吸附性能[J]. 燃料化学学报,2016,44(1):106-112. YANG G S,ZENG G N,ZHAO Q,et al. Preparation of silica gel supported amino acid ionic liquids and their performance capacity towards carbon dioxide[J]. Journal of Fuel Chemistry and Technology,2016,44(1):106-112.
[35] WANG L,LI P,JIN X F,et al. Mechanism of fixation of CO₂ in the presence of hydroxyl-functionalized quaternary ammonium salts[J]. J. CO₂ Util.,2015,10:113-119.
[36] 杨春辉.[HEDUB]Br催化的环氧化合物与二氧化碳制备环状碳酸酯反应的研究[J]. 精细石油化工,2016,33(5):69-72. YANG C H.[HEDUB]Br catalyzed conversion of epoxides and CO₂ to cyclic carbonates[J]. Speciality Petrochemicals,2016,33(5):69-72.
[37] XIAO L F,LV D W,SU D,et al. Influence of acidic strength on the catalytic activity of Brønsted acidic ionic liquids on synthesizing cyclic carbonate from carbon dioxide and epoxide[J]. Journal of Cleaner Production,2014,67:285-290.
[38] YUE C T,SU D,ZHANG X,et al. Amino-functional imidazolium ionic liquids for CO₂ activation and conversion to form cyclic carbonate[J]. Catal. Lett.,2014,144:1313-1321.
[39] YUE S,HAO X J,WANG P P,et al. Amino acid-based ionic liquids for CO₂ conversion to form cycliccarbonate under solvent-free conditions[J]. Molecular Catalysis,2017,433:420-429.
[40] JIANG X,GOU F L,FU X Y,et al. Ionic liquids-functionalized porphyrins as bifunctional catalysts for cycloaddition of carbon ioxide to epoxides[J]. J. CO₂ Util.,2016,16:264-271.
[41] CHAUGULE A A,TAMBOLI A H,KIM H. Ionic liquid as a catalyst for utilization of carbon dioxide to production of linear and cyclic carbonate[J]. Fuel,2017,200:316-332.
[42] VEKARIYA R L. A review of ionic liquids:Applications towards catalytic organic transformations[J]. Journal of Molecular Liquids,2017,227:44-60.
[43] AGRIGENTO P,SYED M A,SORÉE B,et al. Synthesis and high-throughput testing of multilayered supported ionic liquid catalysts for the conversion of CO₂ and epoxides into cyclic carbonates[J]. Catal. Sci. Technol.,2014,4:1598-1607.
[44] KIM M-I,CHOI S-J,KIM D-W,et al. Catalytic performance of zinc containing ionic liquids immobilized on silica for the synthesis of cyclic carbonates[J]. Journal of Industrial and Engineering Chemistry,2014,20:3102-3107.
[45] SANKAR M,AJITHKUMAR T G,SANKAR G,et al. Supported imidazole as heterogeneous catalyst for the synthesis of cyclic carbonates from epoxides and CO₂[J]. Catalysis Communications,2015,59:201-205.
[46] DHARMAN M M,CHOI H J,KIN D W. Synthesis of cyclic carbonate through microwave irradiation using silica-supported ionic liquids:effect of variation in the silica support[J]. Catalysis Today,2011,164:544-547.
[47] CHENG W,CHEN X,SUN J,et al. SBA-15 supported triazolium-based ionic liquids as highly efficient and recyclable catalysts for fixation of CO₂ with epoxides[J]. Catalysis Today,2013,200:117-124.
[48] HANL L,LI H Q,CHOI S J,et al. Ionic liquids grafted on carbon nanotubes as lighly efficient heterogeneneous catalysts for the synthesis of cyclic carbonates[J]. Appl. Catal. A,2012;429/430:67-72.
[49] ZHANG Wei,WANG Qixiang,WU Haihong,et al. A highly ordered mesoporous polymer supported imidazolium-based ionic liquid:an efficient catalyst for cycloaddition of CO₂ with epoxides to produce cyclic carbonates[J]. Green Chemistry,2014,16:4767-4774.
[50] ZHANG W H,HE P P,WU S,et al. Graphene oxide grafted hydroxyl-functionalized ionic liquid:a highly efficient catalyst for cycloaddition of CO₂ with epoxides[J]. Applied Catalysis A:General,2016,509:111-117.
[51] MA D X,LI B Y,LIU K,et al. Bifunctional MOF heterogeneous catalysts based on the synergy of dual functional sites for efficient conversion of CO₂ under mild and co-catalyst free conditions[J]. J. Mater. Chem. A,2015,3:23136-23142.
[52] THARUN J,BHIN K-M,ROSHAN R,et al. Ionic liquid tethered post functionalized ZIF-90 framework for the cycloaddition of propylene oxide and CO₂[J]. Green Chem.,2016,18:2479-2487.
[53] 谭颖. 二氧化碳与环氧化合物合成环状碳酸酯的新型催化剂制备与研究[D]. 南昌:南昌航空大学,2016. TAN Y. Preparation and study on novel catalysts for the synthesis of cyclic carbonate through expoxides and carbon dioxide[D]. Nanchang:Nanchang Hangkong University,2016.
[54] SUN J,WANG J Q,CHENG W G,et al. Chitosan functionalized ionic liquid as a recyclable biopolymer-supported catalyst for cycloaddition of CO₂[J]. Green Chem.,2012,14:654-660.
[55] CHOI H J,SELVARAJ M,PARK D W. Catalytic performance of immobilized ionic liquid onto PEG for the cycloaddition of carbon dioxide to allyl glycidyl ether[J]. Chemical Engineering Science, 2013,100:242-248
[56] DAI W L,ZHANG Y,TAN Y,et al. Reusable and efficient polymer nanoparticles grafted with hydroxyl-functionalized phosphonium-based ionic liquid catalyst for cycloaddition of CO₂ with epoxides[J]. Applied Catalysis A:General,2016,514:43-50.
[57] WU X H,WANG M P,XIE Y Z,et al. Carboxymethyl cellulose supported ionic liquid as a heterogeneouscatalyst for the cycloaddition of CO₂ to cyclic carbonate[J]. Applied Catalysis A:General,2016,519:146-154.
[58] ZHANG X,SU D,XIAO L F,et al. Immobilized protic ionic liquids:efficient catalysts for CO₂ fixation with epoxides[J]. J. CO₂ Util.,2017,17:37-42.
[59] WANG J Q,SUN J,CHENG W G,et al. Experimental and theoretical studies on hydrogen bond-promoted fixation of carbon dioxide and epoxides in cyclic carbonates[J]. Phys. Chem. Chem. Phys.,2012,14:11021-11026.
[60] SHI T Y,WANG J Q,SUN J,et al. Efficient fixation of CO₂ into cyclic carbonates catalyzed by hydroxyl-functionalized poly(ionic liquids)[J]. RSC Advances,2013,3:3726-3732.