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

Cédric Maton (UGent) , Kristof Van Hecke (UGent) and Christian Stevens (UGent)
(2015) NEW JOURNAL OF CHEMISTRY. 39(1). p.461-468
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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 carbovlate 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.
Keywords
SALTS, CARBOXYLATION, CARBENES, CO2, 1_3-DIALKYLIMIDAZOLIUM-2-CARBOXYLATES, 1_3-DIMETHYLIMIDAZOLIUM-2-CARBOXYLATE, DIOXIDE, ACETATE

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Citation

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MLA
Maton, Cédric, Kristof Van Hecke, and Christian Stevens. “Peralkylated Imidazolium Carbonate Ionic Liquids: Synthesis Using Dimethyl Carbonate, Reactivity and Structure.” NEW JOURNAL OF CHEMISTRY 39.1 (2015): 461–468. Print.
APA
Maton, C., Van Hecke, K., & Stevens, C. (2015). Peralkylated imidazolium carbonate ionic liquids: synthesis using dimethyl carbonate, reactivity and structure. NEW JOURNAL OF CHEMISTRY, 39(1), 461–468.
Chicago author-date
Maton, Cédric, Kristof Van Hecke, and Christian Stevens. 2015. “Peralkylated Imidazolium Carbonate Ionic Liquids: Synthesis Using Dimethyl Carbonate, Reactivity and Structure.” New Journal of Chemistry 39 (1): 461–468.
Chicago author-date (all authors)
Maton, Cédric, Kristof Van Hecke, and Christian Stevens. 2015. “Peralkylated Imidazolium Carbonate Ionic Liquids: Synthesis Using Dimethyl Carbonate, Reactivity and Structure.” New Journal of Chemistry 39 (1): 461–468.
Vancouver
1.
Maton C, Van Hecke K, Stevens C. Peralkylated imidazolium carbonate ionic liquids: synthesis using dimethyl carbonate, reactivity and structure. NEW JOURNAL OF CHEMISTRY. 2015;39(1):461–8.
IEEE
[1]
C. Maton, K. Van Hecke, and C. Stevens, “Peralkylated imidazolium carbonate ionic liquids: synthesis using dimethyl carbonate, reactivity and structure,” NEW JOURNAL OF CHEMISTRY, vol. 39, no. 1, pp. 461–468, 2015.
@article{5731492,
  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 carbovlate 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.},
  author       = {Maton, Cédric and Van Hecke, Kristof and Stevens, Christian},
  issn         = {1144-0546},
  journal      = {NEW JOURNAL OF CHEMISTRY},
  keywords     = {SALTS,CARBOXYLATION,CARBENES,CO2,1_3-DIALKYLIMIDAZOLIUM-2-CARBOXYLATES,1_3-DIMETHYLIMIDAZOLIUM-2-CARBOXYLATE,DIOXIDE,ACETATE},
  language     = {eng},
  number       = {1},
  pages        = {461--468},
  title        = {Peralkylated imidazolium carbonate ionic liquids: synthesis using dimethyl carbonate, reactivity and structure},
  url          = {http://dx.doi.org/10.1039/C4NJ01301H},
  volume       = {39},
  year         = {2015},
}

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