Imidazolium hydrogen carbonate ionic liquids: Versatile organocatalysts for chemical conversion of CO2 into valuable chemicals

被引:31
作者
Long, Guangcai [1 ]
Wu, Dongsheng [2 ]
Pan, Hongyan [1 ]
Zhao, Tianxiang [1 ]
Hu, Xingbang [2 ]
机构
[1] Guizhou Univ, Sch Chem & Chem Engn, Key Lab Green Chem & Clean Energy Technol, Guiyang 550025, Guizhou, Peoples R China
[2] Nanjing Univ, Sch Chem & Chem Engn, Nanjing 210093, Jiangsu, Peoples R China
关键词
CO2; conversion; Cyclic carbonate; Ionic liquids; N-methylation; Halogen-free; N-HETEROCYCLIC CARBENES; EFFICIENT ORGANOCATALYSTS; CATALYTIC METHYLATION; DIMETHYL CARBONATE; CYCLIC CARBONATES; AMINES; DIOXIDE; FIXATION; METHANOL; CARBOXYLATES;
D O I
10.1016/j.jcou.2020.101155
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
N-heterocyclic carbenes (NHCs) are found to be efficient halogen-free organocatalysts for chemical conversion of CO2, however, their inherent nature is sensitive to water and air, which leads to limitations in practical applications. In this work, we demonstrate the halogen- and metal-free methods for chemical fixation of CO2 into valuable chemicals of cyclic carbonates and methylamines using air and water-stable organocatalysts of imidazolium hydrogen carbonate ionic liquids (C(n)C(m)ImHCO(3)). Good to excellent yields of cyclic carbonates and methylamines are obtained for varied substrates under mild conditions. Mechanism insight shows that the C(n)C(m)ImHCO(3), as an organic pre-catalysts for N-heterocyclic carbene, can balance to carbene CO2 adduct (C(n)C(m)ImHCO(2)) serving as the active species for conversion of CO2. As a result, the halogen- and metal-free organocatalysts of C(n)C(m)ImHCO(3) again emphasize that are possible to replace traditional carbenes and offer an environment-friendly methodology for chemical fixation of CO2.
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页数:6
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共 43 条
[1]   Ruthenium-Catalyzed Direct Methylation of Primary and Secondary Aromatic Amines Using Carbon Dioxide and Molecular Hydrogen [J].
Beydoun, Kassem ;
vom Stein, Thorsten ;
Klankermayer, Juergen ;
Leitner, Walter .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (36) :9554-9557
[2]   N-formylation and N-methylation of amines using metal-free N-heterocyclic carbene catalysts and CO2 as carbon source [J].
Bobbink, Felix D. ;
Das, Shoubhik ;
Dyson, Paul J. .
NATURE PROTOCOLS, 2017, 12 (02) :417-428
[3]   Synthesis of carbonates and related compounds incorporating CO2 using ionic liquid-type catalysts: State-of-the-art and beyond [J].
Bobbink, Felix D. ;
Dyson, Paul J. .
JOURNAL OF CATALYSIS, 2016, 343 :52-61
[4]   Mono-N-methylation of anilines with methanol catalyzed by a manganese pincer-complex [J].
Bruneau-Voisine, Antoine ;
Wang, Ding ;
Dorcet, Vincent ;
Roisnel, Thierry ;
Darcel, Christophe ;
Sortais, Jean-Baptiste .
JOURNAL OF CATALYSIS, 2017, 347 :57-62
[5]   A general protocol for the reductive N-methylation of amines using dimethyl carbonate and molecular hydrogen: mechanistic insights and kinetic studies [J].
Cabrero-Antonino, Jose R. ;
Adam, Rosa ;
Junge, Kathrin ;
Beller, Matthias .
CATALYSIS SCIENCE & TECHNOLOGY, 2016, 6 (22) :7956-7966
[6]   Cr(salophen) Complex Catalyzed Cyclic Carbonate Synthesis at Ambient Temperature And Pressure [J].
Castro-Osma, Jose A. ;
Lamb, Katie J. ;
North, Michael .
ACS CATALYSIS, 2016, 6 (08) :5012-5025
[7]   Expanding the Ligand Framework Diversity of Carbodicarbenes and Direct Detection of Boron Activation in the Methylation of Amines with CO2 [J].
Chen, Wen-Ching ;
Shen, Jiun-Shian ;
Jurca, Titel ;
Peng, Chun-Jung ;
Lin, Yen-Hsu ;
Wang, Yi-Ping ;
Shih, Wei-Chih ;
Yap, Glenn P. A. ;
Ong, Tiow-Gan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (50) :15207-15212
[8]   Synthesis of Cyclic Carbonates from Epoxides and Carbon Dioxide by Using Organocatalysts [J].
Cokoja, Mirza ;
Wilhelm, Michael E. ;
Anthofer, Michael H. ;
Herrmann, Wolfgang A. ;
Kuehn, Fritz E. .
CHEMSUSCHEM, 2015, 8 (15) :2436-2454
[9]   Phosphazenes: efficient organocatalysts for the catalytic hydrosilylation of carbon dioxide [J].
Courtemanche, Marc-Andre ;
Legare, Marc-Andre ;
Rochette, Etienne ;
Fontaine, Frederic-Georges .
CHEMICAL COMMUNICATIONS, 2015, 51 (31) :6858-6861
[10]   Thiazolium carbene catalysts for the fixation of CO2 onto amines [J].
Das, Shoubhik ;
Bobbink, Felix D. ;
Bulut, Safak ;
Soudani, Mylene ;
Dyson, Paul J. .
CHEMICAL COMMUNICATIONS, 2016, 52 (12) :2497-2500