An efficient catalytic dehydration of fructose and sucrose to 5-hydroxymethylfurfural with protic ionic liquids

Carbohydr Res. 2010 Aug 16;345(12):1698-701. doi: 10.1016/j.carres.2010.05.019. Epub 2010 May 27.


The renewable furan-based platform chemical, 5-hydroxymethylfurfural (HMF), has been efficiently synthesized from d-fructose and sucrose in the presence of a catalytic amount of protic ionic liquids. The 1-methylimidazolium-based and N-methylmorpholinium-based ionic liquids are employed. As a result, 74.8% and 47.5% yields of HMF are obtained from d-fructose and sucrose, respectively, at 90 degrees C for 2h under nitrogen atmosphere when N-methylmorpholinium methyl sulfonate ([NMM](+)[CH(3)SO(3)](-)) is used as the catalyst in an N,N-dimethylformamide-lithium bromide (DMF-LiBr) system. The acidities of ionic liquids are determined by the Hammett method, and the correlation between acidity and catalytic activity is discussed. Moreover, the effects of reaction temperature and time are investigated, and a plausible reaction mechanism for the dehydration of d-fructose is proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Dehydration
  • Fructose / chemistry*
  • Furaldehyde / analogs & derivatives*
  • Furaldehyde / chemical synthesis
  • Furaldehyde / chemistry
  • Ionic Liquids / chemistry*
  • Molecular Structure
  • Protons*
  • Sucrose / chemistry*
  • Temperature


  • Ionic Liquids
  • Protons
  • Fructose
  • Sucrose
  • 5-hydroxymethylfurfural
  • Furaldehyde