Metal Chlorides in Ionic Liquid Solvents Convert Sugars to 5-Hydroxymethylfurfural

Replacing petroleum feedstocks by biomass requires efficient methods to convert carbohydrates to a variety of chemical compounds. We report the catalytic conversion of sugars giving high yield to 5-hydroxymethylfurfural (HMF), a versatile intermediate. Metal halides in 1-alkyl-3-methylimidazolium chloride are catalysts, among which chromium (II) chloride is found to be uniquely effective, leading to the conversion of glucose to HMF with a yield near 70%. A wide range of metal halides is found to catalyze the conversion of fructose to HMF. Only a negligible amount of levulinic acid is formed in these reactions.

[1]  J. Wilkes,et al.  Ionic structure and interactions in 1-methyl-3-ethylimidazolium chloride-aluminum chloride molten salts , 1988 .

[2]  C. Moreau,et al.  Dehydration of fructose and sucrose into 5-hydroxymethylfurfural in the presence of 1-H-3-methyl imidazolium chloride acting both as solvent and catalyst , 2006 .

[3]  Thomas Maschmeyer,et al.  Hydrothermal upgrading of biomass to biofuel; studies on some monosaccharide model compounds. , 2004, Carbohydrate research.

[4]  Kunio Arai,et al.  Glucose and fructose decomposition in subcritical and supercritical water: Detailed reaction pathway, mechanisms, and kinetics , 1999 .

[5]  Kunio Arai,et al.  Kinetics of glucose epimerization and decomposition in subcritical and supercritical water , 1997 .

[6]  Yuriy Román-Leshkov,et al.  Phase Modifiers Promote Efficient Production of Hydroxymethylfurfural from Fructose , 2006, Science.

[7]  Catalysis in Ionic Liquids , 2006 .

[8]  B. Kuster,et al.  5‐Hydroxymethylfurfural (HMF). A Review Focussing on its Manufacture , 1990 .

[9]  M. Olejnik,et al.  Selective dehydration of glucose to hydroxymethylfurfural and a one-pot synthesis of a 4-acetylbutyrolactone from glucose and trioxane in solutions of aluminium salts , 1999 .

[10]  G. N. Richards,et al.  Mechanism of formation of 5-(hydroxymethyl)-2-furaldehyde from D-fructose an sucrose. , 1990, Carbohydrate research.

[11]  H. Vogel,et al.  Dehydration of fructose to 5-hydroxymethylfurfural in sub- and supercritical acetone , 2003 .

[12]  G. Huber,et al.  Production of Liquid Alkanes by Aqueous-Phase Processing of Biomass-Derived Carbohydrates , 2005, Science.

[13]  J. Ashby.  References and Notes , 1999 .

[14]  David K. Johnson,et al.  Top Value-Added Chemicals from Biomass - Volume II—Results of Screening for Potential Candidates from Biorefinery Lignin , 2007 .

[15]  C. Moreau,et al.  Dehydration of fructose into 5-hydroxymethylfurfural in the presence of ionic liquids , 2003 .

[16]  Hiroyuki Yoshida,et al.  ACID-CATALYZED PRODUCTION OF 5-HYDROXYMETHYL FURFURAL FROM D-FRUCTOSE IN SUBCRITICAL WATER , 2006 .

[17]  Masaru Watanabe,et al.  Glucose reactions with acid and base catalysts in hot compressed water at 473 K. , 2005, Carbohydrate research.