title: An unexpected reaction between 5-hydroxymethylfurfural and imidazolium-based ionic liquids at high temperatures.
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.
authors: Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China.
authors: Zehui
authors: Z
authors: Zhang
authors: Wujun
authors: W
authors: Liu
authors: Haibo
authors: H
authors: Xie
authors: Zongbao K
authors: ZK
authors: Zhao
mesh_terms: D002384:Catalysis; D002482:Cellulose / Q000737:chemistry; D005662:Furaldehyde / Q000031:analogs & derivatives* / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D006358:Hot Temperature; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D052578:Ionic Liquids / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure
chemical_list: C570677:1-butyl-2-(5'-methyl-2'-furoyl)imidazole; D007093:Imidazoles; D052578:Ionic Liquids; C502841:1-butyl-3-methylimidazolium chloride; C008046:5-hydroxymethylfurfural; C029899:imidazole; D002482:Cellulose; D005662:Furaldehyde; D005947:Glucose