Reactions of d-fructose in water at temperatures up to 400 °C and pressures up to 100 MPa

Taku Michael Aida, Kiyohiko Tajima, Masaru Watanabe, Yuki Saito, Kiyoshi Kuroda, Toshiyuki Nonaka, Hideo Hattori, Richard Lee Smith, Kunio Arai

Research output: Contribution to journalArticlepeer-review

141 Citations (Scopus)

Abstract

Reactions of d-fructose in water at high temperatures (350 and 400 °C) and pressures (up to 100 MPa) were studied using a flow reactor. High temperature (400 °C) and moderate pressure (40 MPa) conditions enhanced the yields of retro-aldol related products such as glyceraldehyde, dihydroxyacetone and pyruvaldehyde. High temperature, high pressure conditions enhanced retro-aldol reactions and water related reactions such as hydrolysis and dehydration. Comparison between d-fructose and d-glucose experiments showed that higher yields for 5-HMF were obtained starting from d-fructose than d-glucose. Surprisingly, higher yields of furfural were obtained starting from d-glucose than from d-fructose which is contrary to reaction pathways in the hydrothermal literature. Based on the experimental results, a possible reaction scheme is proposed for water catalyzed (i) benzilic acid rearrangement reactions from pyruvaldehyde to lactic acid and (ii) retro-aldol reaction from d-glucose to furfural.

Original languageEnglish
Pages (from-to)110-119
Number of pages10
JournalJournal of Supercritical Fluids
Volume42
Issue number1
DOIs
Publication statusPublished - 2007 Aug 1

Keywords

  • 5-HMF
  • Biomass
  • Furfural
  • High temperature water
  • Lactic acid
  • d-Fructose

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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