Biobased Furanics: Kinetic Studies on the Acid Catalyzed Decomposition of 2-Hydroxyacetyl Furan in Water Using Bronsted Acid Catalysts

J. N. M. Soetedjo, H. H. van de Bovenkamp, P. J. Deuss, H. J. Heeres*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

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Abstract

Biobased furanics like 5-hydroxymethylfurfural (5-1-IMF) are interesting platform chemicals for the synthesis of biofuel additives and polymer precursors. 5-HMF is typically prepared from C6 ketoses like fructose, psicose, sorbose and tagatose. A known byproduct is 2-hydroxyacetylfuran (2-HAF), particularly when using sorbose and psicose as the reactants. We here report an experimental and kinetic modeling study on the rate of decomposition of 2-HAF in a typical reaction medium for 5-HMF synthesis (water, Bronsted acid), with the incentive to gain insights in the stability of 2-HAF. A total of 12 experiments were performed (batch setup) in water with sulfuric acid as the catalyst (100-170 degrees C, C-H2SO4 ranging between 0.033 and 1.37 M and an initial 2-HAF concentration between 0.04 and 0.26 M). Analysis of the reaction mixtures showed a multitude of products, of which levulinic acid (LA) and formic acid (FA) were the most prominent (Y-max,Y-FA = 24 mol %, Y-max,Y-LA = 10 mol %) when using HCI. In contrast, both LA and FA were formed in minor amounts when using H2SO4 as the catalyst. The decomposition reaction of 2-HAF using sulfuric acid was successfully modeled (R-2 = 0.9957) using a first-order approach in 2-1-IAF and acid. The activation energy was found to be 98.7 ( 2.2) kJ mol(-1).

Original languageEnglish
Pages (from-to)3993-4001
Number of pages9
JournalACS Sustainable Chemistry & Engineering
Volume5
Issue number5
DOIs
Publication statusPublished - May-2017

Keywords

  • Platform chemicals
  • Hydroxyacetylfuran
  • Kinetic modeling
  • Acid catalysis
  • Levulinic acid
  • Formic acid
  • LEVULINIC ACID
  • D-FRUCTOSE
  • D-GLUCOSE
  • SUBCRITICAL WATER
  • HYDROGEN-TRANSFER
  • HIGH-TEMPERATURE
  • CONVERSION
  • ALDOSES
  • 2-FURALDEHYDE
  • DEHYDRATION

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