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Issue 8, 2015
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An ionic liquid–organics–water ternary biphasic system enhances the 5-hydroxymethylfurfural yield in catalytic conversion of glucose at high concentrations

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Abstract

Increasing the glucose loading in the 1-butyl-3-methylimidazolium chloride ([BMIM]Cl) ionic liquid containing a dissolved CrCl3 catalyst system led to excessive formation of humins and a serious decrease in the 5-hydroxymethylfurfural (5-HMF) yield. A biphasic system containing glycol dimethyl ether (GDE) as the extraction phase, and [BMIM]Cl/CrCl3/glucose in combination with a partitioned amount of GDE and an appropriate amount of water as the reaction phase was found to be highly efficient for the reaction; CrCl3 catalyzed the formation of 5-HMF in 64.5 mol% yield from a very high glucose concentration (80 wt% with respect to the ionic liquid) at 108 °C. This 5-HMF yield in the [BMIM]Cl–GDE–H2O ternary biphasic system nearly doubled that obtained in the single [BMIM]Cl/CrCl3/glucose reaction phase. Importantly, the GDE phase contained about 56% of the generated 5-HMF without detectable contamination by the ionic liquid or carbohydrates. GDE served multiple functions: as a hydrogen-bond acceptor, it exhibited excellent extraction performance for 5-HMF; due to its low boiling point and suitable solubility saturation point in the ionic liquid, a sustained GDE bubbling phenomenon in the ionic liquid phase was observed that promoted the rate of inter-phase mass-transfer of 5-HMF in reactions; and GDE mediated the [BMIM]Cl phase to a reduced viscosity. In addition, an appropriate amount of water in the ternary system promoted the extraction efficiency of 5-HMF and also lowered the viscosity of [BMIM]Cl/glucose. The ionic liquid–organics–water ternary biphasic system has been demonstrated for high 5-HMF productivity and separation efficiency.

Graphical abstract: An ionic liquid–organics–water ternary biphasic system enhances the 5-hydroxymethylfurfural yield in catalytic conversion of glucose at high concentrations

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Publication details

The article was received on 15 May 2015, accepted on 02 Jun 2015 and first published on 02 Jun 2015


Article type: Paper
DOI: 10.1039/C5GC01039J
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Citation: Green Chem., 2015,17, 4206-4216
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    An ionic liquid–organics–water ternary biphasic system enhances the 5-hydroxymethylfurfural yield in catalytic conversion of glucose at high concentrations

    J. Zhou, Z. Xia, T. Huang, P. Yan, W. Xu, Z. Xu, J. Wang and Z. C. Zhang, Green Chem., 2015, 17, 4206
    DOI: 10.1039/C5GC01039J

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