Insights into hydrogen bond donor promoted fixation of carbon dioxide with epoxides catalyzed by ionic liquids

被引:118
作者
Liu, Mengshuai [1 ]
Gao, Kunqi [1 ]
Liang, Lin [2 ]
Wang, Fangxiao [1 ]
Shi, Lei [1 ]
Sheng, Li [1 ]
Sun, Jianmin [1 ,3 ]
机构
[1] Harbin Inst Technol, Acad Fundamental & Interdisciplinary Sci, Harbin 150080, Peoples R China
[2] Harbin Inst Technol, Sch Life Sci & Technol, Harbin 150080, Peoples R China
[3] Harbin Inst Technol, State Key Lab Urban Water Resource & Environm, Harbin 150080, Peoples R China
基金
中国国家自然科学基金;
关键词
CHEMICAL FIXATION; CYCLIC CARBONATES; EFFICIENT CATALYSTS; ALUMINUM COMPLEXES; STYRENE CARBONATE; CO2; CYCLOADDITION; OXIDE; REACTIVITY; CONVERSION;
D O I
10.1039/c4cp05464d
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Catalytic coupling of carbon dioxide with epoxides to obtain cyclic carbonates is an important reaction that has been receiving renewed interest. In this contribution, the cycloaddition reaction in the presence of various hydrogen bond donors (HBDs) catalyzed by hydroxyl/carboxyl task-specific ionic liquids (ILs) is studied in detail. It was found that the activity of ILs could be significantly enhanced in the presence of ethylene glycol (EG), and EG/HEBimBr were the most efficient catalysts for the CO2 cycloaddition to propylene oxide. Moreover, the binary catalysts were also efficiently versatile for the CO2 cycloaddition to less active epoxides such as styrene oxide and cyclohexene oxide. Besides, the minimum energy paths for this hydrogen bond-promoted catalytic reaction were calculated using the density functional theory (DFT) method. The DFT results suggested that the ring-closing reaction was the rate-determining step in the HEBimBr-catalyzed cycloaddition reaction but the EG addition could remarkably reduce its energy barrier as the formation of a hydrogen bond between EG and the oxygen atom of epoxides led this process along the standard S(N)2 mechanism. As a result, the ring-opening reaction became the rate-determining step in the EG/HEBimBr-catalyzed cycloaddition reaction. The work reported herein helped the understanding and design of catalysts for efficient fixation of CO2 to epoxides via hydrogen bond activation.
引用
收藏
页码:5959 / 5965
页数:7
相关论文
共 47 条
[1]   Synthesis and high-throughput testing of multilayered supported ionic liquid catalysts for the conversion of CO2 and epoxides into cyclic carbonates [J].
Agrigento, Paola ;
Al-Amsyar, Syed M. ;
Soree, Benjamin ;
Taherimehr, Masoumeh ;
Gruttadauria, Michelangelo ;
Aprile, Carmela ;
Pescarmona, Paolo P. .
CATALYSIS SCIENCE & TECHNOLOGY, 2014, 4 (06) :1598-1607
[2]   Cycloaddition of CO2 and epoxides catalyzed by imidazolium bromides under mild conditions: influence of the cation on catalyst activity [J].
Anthofer, Michael H. ;
Wilhelm, Michael E. ;
Cokoja, Mirza ;
Markovits, Iulius I. E. ;
Poethig, Alexander ;
Mink, Janos ;
Herrmann, Wolfgang A. ;
Kuehn, Fritz E. .
CATALYSIS SCIENCE & TECHNOLOGY, 2014, 4 (06) :1749-1758
[3]   A facile and efficient synthesis of styrene carbonate via cycloaddition of CO2 to styrene oxide over ordered mesoporous MCM-41-Imi/Br catalyst [J].
Appaturi, Jimmy Nelson ;
Adam, Farook .
APPLIED CATALYSIS B-ENVIRONMENTAL, 2013, 136 :150-159
[4]   Influence of Temperature and Pressure on Cyclic Carbonate Synthesis Catalyzed by Bimetallic Aluminum Complexes and Application to Overall syn-Bis-hydroxylation of Alkenes [J].
Beattie, Christopher ;
North, Michael ;
Villuendas, Pedro ;
Young, Carl .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (02) :419-426
[5]   Reactivity of ionic liquids [J].
Chowdhury, Shahana ;
Mohan, Ram S. ;
Scott, Janet L. .
TETRAHEDRON, 2007, 63 (11) :2363-2389
[6]   Polymers anchored with carboxyl-functionalized di-cation ionic liquids as efficient catalysts for the fixation of CO2 into cyclic carbonates [J].
Dai Wei-Li ;
Jin Bi ;
Luo Sheng-Lian ;
Luo Xu-Biao ;
Tu Xin-Man ;
Au Chak-Tong .
CATALYSIS SCIENCE & TECHNOLOGY, 2014, 4 (02) :556-562
[7]   A concise review of computational studies of the carbon dioxide-epoxide copolymerization reactions [J].
Darensbourg, Donald J. ;
Yeung, Andrew D. .
POLYMER CHEMISTRY, 2014, 5 (13) :3949-3962
[8]   Theoretical study on the chemical fixation of carbon dioxide with propylene oxide catalyzed by ammonium and guanidinium salts [J].
Foltran, Stephanie ;
Mereau, Raphael ;
Tassaing, Thierry .
CATALYSIS SCIENCE & TECHNOLOGY, 2014, 4 (06) :1585-1597
[9]   On the chemical fixation of supercritical carbon dioxide with epoxides catalyzed by ionic salts: an in situ FTIR and Raman study [J].
Foltran, Stephanie ;
Alsarraf, Jerome ;
Robert, Frederic ;
Landais, Yannick ;
Cloutet, Eric ;
Cramail, Henri ;
Tassaing, Thierry .
CATALYSIS SCIENCE & TECHNOLOGY, 2013, 3 (04) :1046-1055
[10]   Crystal Engineering of an nbo Topology Metal-Organic Framework for Chemical Fixation of CO2 under Ambient Conditions [J].
Gao, Wen-Yang ;
Chen, Yao ;
Niu, Youhong ;
Williams, Kia ;
Cash, Lindsay ;
Perez, Pastor J. ;
Wojtas, Lukasz ;
Cai, Jianfeng ;
Chen, Yu-Sheng ;
Ma, Shengqian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (10) :2615-2619