On the chemical fixation of supercritical carbon dioxide with epoxides catalyzed by ionic salts: an in situ FTIR and Raman study

被引:65
作者
Foltran, Stephanie [1 ,2 ]
Alsarraf, Jerome [1 ,2 ]
Robert, Frederic [1 ,2 ]
Landais, Yannick [1 ,2 ]
Cloutet, Eric [3 ,4 ]
Cramail, Henri [3 ,4 ]
Tassaing, Thierry [1 ,2 ]
机构
[1] Univ Bordeaux, ISM, UMR 5255, F-33400 Talence, France
[2] CNRS, ISM, UMR 5255, F-33400 Talence, France
[3] Univ Bordeaux, LCPO, UMR 5629, F-33600 Pessac, France
[4] CNRS, LCPO, UMR 5629, F-33600 Pessac, France
关键词
CYCLIC ORGANIC CARBONATES; BUTYL GLYCIDYL ETHER; COUPLING REACTION; DIMETHYL CARBONATE; STYRENE OXIDE; CO2; PROPYLENE; CYCLOADDITION; LIQUID; COPOLYMERIZATION;
D O I
10.1039/c2cy20784b
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
A series of ionic salts have been investigated to catalyze the coupling reaction between epoxide and carbon dioxide at T = 80 degrees C and P = 8 MPa. Among them, we focused particularly on tetrabutylammonium, imidazolium and guanidinium salts. The kinetics of the synthesis was monitored in situ using both FTIR and Raman spectroscopy. For a given reaction time, the best yields were obtained with 1,5,7-triaza-bicyclo[4.4.0] dec-5-enium bromide (TBD.HBr) and 1-methyl-3-methylimidazolium iodide (MMImI) and both have not been investigated in detail in the literature before. Thanks to this catalyst screening, we have verified how some functional groups of the catalyst can activate the epoxide and the CO2 molecule enabling us to go further in the mechanism comprehension of this reaction. Due to its easier and less expensive synthesis than other ionic liquids, we focused more particularly on TBD.HBr that also offers a good conversion rate even at low pressure (80 degrees C and 1 MPa).
引用
收藏
页码:1046 / 1055
页数:10
相关论文
共 70 条
[61]   Synthesis, characterization of a new bicobalt complex [Co2L2(C2H5OH)2Cl2] and application in cyclic carbonate synthesis [J].
Wang, Juangang ;
Wu, Jincai ;
Tang, Ning .
INORGANIC CHEMISTRY COMMUNICATIONS, 2007, 10 (12) :1493-1495
[62]   Merging Sustainability with Organocatalysis in the Formation of Organic Carbonates by Using CO2 as a Feedstock [J].
Whiteoak, Christopher J. ;
Nova, Ainara ;
Maseras, Feliu ;
Kleij, Arjan W. .
CHEMSUSCHEM, 2012, 5 (10) :2032-2038
[63]   Greenhouse gases in the Earth system: a palaeoclimate perspective [J].
Wolff, Eric W. .
PHILOSOPHICAL TRANSACTIONS OF THE ROYAL SOCIETY A-MATHEMATICAL PHYSICAL AND ENGINEERING SCIENCES, 2011, 369 (1943) :2133-2147
[64]   Mg-Al mixed oxides as highly active acid-base catalysts for cycloaddition of carbon dioxide to epoxides [J].
Yamaguchi, K ;
Ebitani, K ;
Yoshida, T ;
Yoshida, H ;
Kaneda, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (18) :4526-4527
[65]   Lewis Basic Ionic Liquids-Catalyzed Conversion of Carbon Dioxide to Cyclic Carbonates [J].
Yang, Zhen-Zhen ;
He, Liang-Nian ;
Miao, Cheng-Xia ;
Chanfreau, Sebastien .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (13) :2233-2240
[66]   Magnesium oxide-catalysed reaction of carbon dioxide with an epoxide with retention of stereochemistry [J].
Yano, T ;
Matsui, H ;
Koike, T ;
Ishiguro, H ;
Fujihara, H ;
Yoshihara, M ;
Maeshima, T .
CHEMICAL COMMUNICATIONS, 1997, (12) :1129-1130
[67]   Non-halogen catalysts for propylene carbonate synthesis from CO2 under supercritical conditions [J].
Yasuda, H ;
He, LN ;
Takahashi, T ;
Sakakura, T .
APPLIED CATALYSIS A-GENERAL, 2006, 298 :177-180
[68]   Cyclic carbonate synthesis from supercritical carbon dioxide and epoxide over lanthanide oxychloride [J].
Yasuda, H ;
He, LN ;
Sakakura, T .
JOURNAL OF CATALYSIS, 2002, 209 (02) :547-550
[69]   Novel methodologies for the synthesis of cyclic carbonates [J].
Yoshida, M ;
Ihara, M .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (12) :2886-2893
[70]   Cycloaddition of carbon dioxide to butyl glycidyl ether using imidazolium salt ionic liquid as a catalyst [J].
Yu, Jeong-In ;
Ju, Hye-Young ;
Kim, Kyung-Hoon ;
Park, Dae-Won .
KOREAN JOURNAL OF CHEMICAL ENGINEERING, 2010, 27 (02) :446-451