Issue 1, 2015

Peralkylated imidazolium carbonate ionic liquids: synthesis using dimethyl carbonate, reactivity and structure

Abstract

Tri- and tetra-alkylimidazoles are quaternised into their corresponding ionic liquids with dimethyl carbonate. Upon metathesis of the obtained methyl carbonate salts, only gaseous by-products are generated. These methyl carbonate salts can be transformed into hydrogen carbonate salts by reaction with water. The salts containing a carbonate anion are very alkaline, which results in a hydrogen/deuterium exchange on the anion and some of the cation protons, depending on the substitution. Moreover, the crystalline 1-ethyl-3,4,5-trimethylimidazolium hydrogen carbonate formed carboxylate species upon dissolution. In particular, the carboxylate was able to regenerate the carbene and in the presence of chloroform, this led to the formation of the chloride salt.

Graphical abstract: Peralkylated imidazolium carbonate ionic liquids: synthesis using dimethyl carbonate, reactivity and structure

Supplementary files

Article information

Article type
Paper
Submitted
05 Aug 2014
Accepted
15 Oct 2014
First published
16 Oct 2014

New J. Chem., 2015,39, 461-468

Author version available

Peralkylated imidazolium carbonate ionic liquids: synthesis using dimethyl carbonate, reactivity and structure

C. Maton, K. Van Hecke and C. V. Stevens, New J. Chem., 2015, 39, 461 DOI: 10.1039/C4NJ01301H

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