Analytical Sciences

Thermal Decomposition Behaviors of Imidazolium-type Ionic Liquids Studied by Pyrolysis-Gas Chromatography

Hajime OHTANI, Shinji ISHIMURA, and Miyuki KUMAI

Department of Materials Science and Engineering, Graduate School of Engineering, Nagoya Institute of Technology, Nagoya 466-8555, Japan

Thermal decomposition behaviors of a series of imidazolium-type ionic liquid samples were studied by pyrolysis-gas chromatography at 550°C using various detectors. As for the imidazolium halides, haloalkanes and 1-alkylimidazoles corresponding to the alkyl substituents were mainly formed through the nucleophilic attacks of halide ions to the alkyl groups followed by C-N bond cleavage, along with a minor amount of alkenes. Meanwhile, in the case of the ionic liquids with BF₄, PF₆ and CF₃SO₃ anions, corresponding alkenes were predominantly produced along with 1-alkylimidazoles rather than haloalkanes. No boron-containing products were found even from the samples with BF₄ anion, whereas minor but clear peaks of phosphorous-containing products were observed in the pyrograms of the samples with PF₆ anions. As for the samples with longer alkyl group, the pyrolyzates reflecting the C-C bond scissions in the alkyl groups were also formed to some extent. Meanwhile, imidazole rings did not decompose under the experimental conditions at around 550°C.

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