Electroreduction of 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide ionic liquid: Oriented product selectivity through the electrode material

被引:12
作者
Michez, Roman [1 ]
Vander Steen, Julien [1 ]
Doneux, Thomas [1 ]
Luhmer, Michel [2 ]
Buess-Herman, Claudine [1 ]
机构
[1] Univ Libre Bruxelles, Serv Chim Analyt & Chim Interfaces, Blvd Triomphe 2,CP 255, B-1050 Brussels, Belgium
[2] Univ Libre Bruxelles, Lab Resonance Magnet Nucl Haute Resolut, Ave F-D Roosevelt 50,CP 160-08, B-1050 Brussels, Belgium
关键词
1-butyl-3-methylimidazolium; bis(trifluoromethanesulfonyl)imide; Ionic liquid; Carbene; NMR spectroscopy; Gold; Platinum; N-HETEROCYCLIC CARBENES; ELECTROCHEMICAL REDUCTION; PLATINUM-ELECTRODES; CARBON-DIOXIDE; STABILITY; REACTIVITY; MECHANISMS; WINDOWS; CATION; SALTS;
D O I
10.1016/j.electacta.2018.03.057
中图分类号
O646 [电化学、电解、磁化学];
学科分类号
081704 ;
摘要
A new insight into the electrochemical reduction mechanism of imidazolium cations is given by examining the cathodic stability of the 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl) imide [BMIm][NTf2] ionic liquid at platinum, gold, copper and mercury electrodes. Potentiostatic electrolyses were performed under nitrogen-saturated conditions and the major reduction products of the BMIm(+) cation were quantified by H-1 NMR spectroscopy. The product selectivity is influenced by the electrode material and by the presence of an additional proton source in the medium, evidencing the key role of adsorbed hydrogen in the mechanism of BMIm(+) electroreduction. (c) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:434 / 439
页数:6
相关论文
共 25 条
[1]   Ionic liquids in the electrochemical valorisation of CO2 [J].
Alvarez-Guerra, Manuel ;
Albo, Jonathan ;
Alvarez-Guerra, Enrique ;
Irabien, Angel .
ENERGY & ENVIRONMENTAL SCIENCE, 2015, 8 (09) :2574-2599
[2]  
Armand M, 2009, NAT MATER, V8, P621, DOI [10.1038/nmat2448, 10.1038/NMAT2448]
[3]   Hydrophobic, highly conductive ambient-temperature molten salts [J].
Bonhote, P ;
Dias, AP ;
Papageorgiou, N ;
Kalyanasundaram, K ;
Gratzel, M .
INORGANIC CHEMISTRY, 1996, 35 (05) :1168-1178
[4]   Extended electrochemical windows made accessible by room temperature ionic liquid/organic solvent electrolyte systems [J].
Buzzeo, MC ;
Hardacre, C ;
Compton, RG .
CHEMPHYSCHEM, 2006, 7 (01) :176-180
[5]   From the reactivity of N-heterocyclic carbenes to new chemistry in ionic liquids [J].
Canal, JP ;
Ramnial, T ;
Dickie, DA ;
Clyburne, JAC .
CHEMICAL COMMUNICATIONS, 2006, (17) :1809-1818
[6]   Electrogenerated N-Heterocyclic Carbenes in the Room Temperature Parent Ionic Liquid as an Efficient Medium for Transesterification/Acylation Reactions [J].
Chiarotto, Isabella ;
Feroci, Marta ;
Sotgiu, Giovanni ;
Inesi, Achille .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (02) :326-331
[7]   Electrochemical Stability of Ionic Liquids: General Influences and Degradation Mechanisms [J].
De Vos, Nils ;
Maton, Cedric ;
Stevens, Christian V. .
CHEMELECTROCHEM, 2014, 1 (08) :1258-1270
[8]  
Endres F., 2008, ELECTRODEPOSITION IO, DOI [10.1002/9783527622917, DOI 10.1002/9783527622917]
[9]   Stability and organocatalytic efficiency of N-heterocyclic carbenes electrogenerated in organic solvents from imidazolium ionic liquids [J].
Feroci, Marta ;
Chiarotto, Isabella ;
D'Anna, Francesca ;
Forte, Gianpiero ;
Noto, Renato ;
Inesi, Achille .
ELECTROCHIMICA ACTA, 2015, 153 :122-129
[10]   On the reactivity and stability of electrogenerated N-heterocyclic carbene in parent 1-butyl-3-methyl-1H-imidazolium tetrafluoroborate: Formation and use of N-heterocyclic carbene-CO2 adduct as latent catalyst [J].
Feroci, Marta ;
Chiarotto, Isabella ;
Ciprioti, Stefano Vecchio ;
Inesi, Achille .
ELECTROCHIMICA ACTA, 2013, 109 :95-101