Efficient conversion of fructose into 5-ethoxymethylfurfural with hydrogen sulfate ionic liquids as co-solvent and catalyst

Haixin Guo, Xinhua Qi, Yuya Hiraga, Taku M. Aida, Richard Lee Smith

Research output: Contribution to journalArticlepeer-review

48 Citations (Scopus)

Abstract

Hydrogen sulfate ionic liquid as co-solvent and as homogeneous catalyst in ethanol solvent allows efficient conversion of fructose into 5-ethoxymethylfurfural (5-EMF) directly at mild conditions. Ionic liquids [A][B] ([A]+ = 1-methylimidazolium, [C1im]+; 1-ethyl-3-methylimidazolium, [C2mim]+; or 1-butyl-3-methylimidazolium, [C4mim]+, [B] = hydrogen sulfate, [HSO4]; acetate, [AC]; diethylphosphate, [DEP]); dimethylphosphate, [DMP]) or chloride, [Cl]were studied. In the [C4mim][HSO4]-ethanol system, 83% 5-EMF yields were obtained from fructose at 130 °C in 20 min reaction time that can be attributed to the anion acidity and to a stabilizing hydrogen bond that forms between the ionic liquid and 5-HMF. The ionic liquid was demonstrated to be reusable for five times with minimal loss in catalytic activity (ca. 3% loss in 5-EMF yield). Hydrogen sulfate ionic liquids as co-solvent and catalyst in ethanol allow efficient conversion of biomass-related mixtures that contain fructose or a 5-HMF intermediate into biofuels.

Original languageEnglish
Pages (from-to)508-514
Number of pages7
JournalChemical Engineering Journal
Volume314
DOIs
Publication statusPublished - 2017

Keywords

  • 5-EMF
  • Biofuel
  • Biomass conversion
  • Etherification
  • Hydrogen bond

ASJC Scopus subject areas

  • Chemistry(all)
  • Environmental Chemistry
  • Chemical Engineering(all)
  • Industrial and Manufacturing Engineering

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