Preparation of 1-Hydroxy-2,5-hexanedione from HMF by the Combination of Commercial Pd/C and Acetic Acid

Molecules. 2020 May 27;25(11):2475. doi: 10.3390/molecules25112475.

Abstract

The development of a simple and durable catalytic system for the production of chemicals from a high concentration of a substrate is important for biomass conversion. In this manuscript, 5-hydroxymethylfurfural (HMF) was converted to 1-hydroxy-2,5-hexanedione (HHD) using the combination of commercial Pd/C and acetic acid (AcOH) in water. The influence of temperature, H2 pressure, reaction time, catalyst amount and the concentration of AcOH and HMF on this transformation was investigated. A 68% yield of HHD was able to be obtained from HMF at a 13.6 wt% aqueous solution with a 98% conversion of HMF. The resinification of intermediates on the catalyst was characterized to be the main reason for the deactivation of Pd/C. The reusability of the used Pd/C was studied to find that most of the activity could be recovered by being washed in hot tetrahydrofuran.

Keywords: 1-hydroxy-2,5-hexanedione; HMF; Pd/C; acetic acid; high concentration.

MeSH terms

  • Acetic Acid / chemistry*
  • Furaldehyde / analogs & derivatives
  • Furaldehyde / chemistry
  • Hexanones / chemistry*
  • Pressure
  • Reaction Time
  • Temperature
  • Water / chemistry

Substances

  • Hexanones
  • Water
  • 5-hydroxymethylfurfural
  • 2,5-hexanedione
  • Furaldehyde
  • Acetic Acid