The acid-catalyzed dehydration of fructose is important in the effective utilization of biomass. This reaction can lead to production of 5-hydroxymethyl furfural (HMF) that can be readily converted into other useful molecules, including; dimethylfuran, furan dicarboxylic acid, and levulinic acid.  Levulinic acid is a desirable product since it can be converted to liquid transportation fuels and chemical feedstocks. The design of an efficient catalyst for the production of HMF requires knowledge of the details of the reaction mechanism for the formation of HMF from fructose in order to pin-point the steps that limit selectivity and rate. In the current study, the mechanism of the acid-catalyzed dehydration of fructose to from HMF was probed by studying the kinetics of this reaction in DMSO with Amberlyst 70, niobic acid/phosphate, or sulfuric acid catalysts.  Kinetic data for the different tautomers of fructose were obtained at different temperatures, acidites, and catalyst to reactant ratios. The implications of the kinetic data with regard to the magnitudes of the rates that are observed, and their dependence on reaction conditions, for different reaction steps, as well as the rate limiting step in the reaction, will be discussed. Such data are needed as inputs to develop a complete molecular level model of the kinetics of the reaction of fructose to form HMF.  This material is based upon work supported as part of the Institute for Atom-efficient Chemical Transformations (IACT), an Energy Frontier Research Center funded by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences.

Kinetics of reaction of fructose to form 5-(hydroxymethyl) furfural

246th National Meeting (2013)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.