An unexpected reaction between 5-hydroxymethylfurfural and imidazolium-based ionic liquids at high temperatures

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Abstract

A new compound was detected during the production of 5- hydroxymethylfurfural (HMF) from glucose and cellulose in the ionic liquid 1-butyl-3-methylimidazolium chloride ([Bmim]Cl) at high temperatures. Further experiments found that it was derived from the reaction of HMF with [Bmim]Cl. The structure of new compound was established as 1-butyl-2-(5'-methyl-2'-furoyl) imidazole (BMI) based on nuclear magnetic resonance and mass spectrometry analysis, and a possible mechanism for its formation was proposed. Reactions of HMF with other imidazolium-based ionic liquids were performed to check the formation of BMI. Our results provided new insights in terms of side reactions between HMF and imidazolium-based ionic liquids, which should be valuable for designing better processes for the production of furans using biomass and related materials.

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Zhang, Z., Liu, W., Xie, H., & Zhao, Z. K. (2011). An unexpected reaction between 5-hydroxymethylfurfural and imidazolium-based ionic liquids at high temperatures. Molecules, 16(10), 8463–8474. https://doi.org/10.3390/molecules16108463

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