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Molecules 2011, 16(10), 8463-8474; doi:10.3390/molecules16108463

An Unexpected Reaction between 5-Hydroxymethylfurfural and Imidazolium-Based Ionic Liquids at High Temperatures

1
Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China
2
Dalian National Laboratory for Clean Energy, Dalian 116023, China
3
Key Laboratory of Catalysis and Materials Sciences of the State Ethnic Affairs Commission & Ministry of Education, College of Chemistry and Material Science, South-Central University for Nationalities, Wuhan 430074, China
*
Authors to whom correspondence should be addressed.
Received: 22 August 2011 / Revised: 14 September 2011 / Accepted: 26 September 2011 / Published: 11 October 2011
(This article belongs to the Section Molecular Diversity)
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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.
Keywords: side reaction; HMF; ionic liquids; 1-butyl-2-(5’-methyl-2’-furoyl)imidazole side reaction; HMF; ionic liquids; 1-butyl-2-(5’-methyl-2’-furoyl)imidazole
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Zhang, Z.; Liu, W.; Xie, H.; Zhao, Z.K. An Unexpected Reaction between 5-Hydroxymethylfurfural and Imidazolium-Based Ionic Liquids at High Temperatures. Molecules 2011, 16, 8463-8474.

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