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

Springer Science and Business Media LLC - Tập 16 Số 10 - Trang 8463-8474
Zehui Zhang1,2, Wujun Liu1, Haibo Xie1,3, Zongbao K. Zhao1,3
1Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China
2Key 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
3Dalian National Laboratory for Clean Energy, Dalian, 116023, China

Tóm tắt

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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