Effective Oxidation of (5-Hydroxymethyl)furfural to 2,5-Diformylfuran by an Acetal Protection Strategy

T. Boonyakarn, Jan J. Wiesfeld, M. Asakawa, Lulu Chen, A. (Atsushi) Fukuoka, Emiel J.M. Hensen, Kiyotaka Nakajima (Corresponding author)

Research output: Contribution to journalArticleAcademicpeer-review

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Abstract

An acetal protection strategy for (5-hydroxymethyl)furfural (HMF) was used to obtain 2,5-diformyfuran (DFF) using concentrated HMF solutions and a γ-Al 2 O 3 -supported Ru catalyst (Ru/γ-Al 2 O 3 ). The HMF-acetal with 1,3-propanediol can be oxidized to DFF-acetal with a yield of 84.0% at an HMF conversion of 94.2% from a 50 wt% solution. In contrast, aerobic oxidation of nonprotected HMF using a 10 wt% solution afforded DFF only in a moderate yield (52.3%). Kinetic studies indicate that the six-membered ring acetal group not only prevents side reactions but also accelerates aerobic oxidation of the -CH 2 OH moiety to -CHO under retention of the acetal functionality. Organic deposits formed during the reaction explained the significant decrease in the activity of the Ru/γ-Al 2 O 3 catalyst, which could be recovered neither by washing in water or organic solvents, nor by a calcination-reduction treatment. Sonication of the used Ru/γ-Al 2 O 3 catalyst in an aqueous NaOH solution successfully removed the deposits and allowed reuse of the catalyst for at least four times without activity loss.
Original languageEnglish
Article numbere202200059
Number of pages7
JournalChemSusChem
Volume15
Issue number7
Early online date11 Feb 2022
DOIs
Publication statusPublished - 7 Apr 2022

Keywords

  • 5-hydroxymethylfurfural
  • biomass
  • diformylfuran
  • heterogeneous catalysis
  • oxidation
  • Water
  • Furaldehyde/analogs & derivatives
  • Furans
  • Kinetics
  • Acetals

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