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

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

1,3, 1, 1,2,* email and 1,2,* email
Received: 22 August 2011; in revised form: 14 September 2011 / Accepted: 26 September 2011 / Published: 11 October 2011
(This article belongs to the Section Organic Synthesis)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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
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MDPI and ACS Style

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.

AMA Style

Zhang Z, Liu W, Xie H, Zhao ZK. An Unexpected Reaction between 5-Hydroxymethylfurfural and Imidazolium-Based Ionic Liquids at High Temperatures. Molecules. 2011; 16(10):8463-8474.

Chicago/Turabian Style

Zhang, Zehui; Liu, Wujun; Xie, Haibo; Zhao, Zongbao K. 2011. "An Unexpected Reaction between 5-Hydroxymethylfurfural and Imidazolium-Based Ionic Liquids at High Temperatures." Molecules 16, no. 10: 8463-8474.

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