Furfural to Cyclopentanone – a Search for Putative Oligomeric By-products

Rick Baldenhofer, Jean Paul Lange, Sascha R.A. Kersten, M. Pilar Ruiz*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

4 Citations (Scopus)
105 Downloads (Pure)

Abstract

We report here on the reductive rearrangement of biomass-derived furfural to cyclopentanone, a promising non-fossil feedstock for fuels and chemicals. An underreported aspect of this reaction is the inevitable formation of heavy byproducts. To mitigate its formation, process condition such as, solvent, catalyst, temperature, acidity, and feed concentration were varied to unravel the chemistry and improve the reaction performance. Water medium was confirmed to play a crucial role, as organic solvents were unable to deliver cyclopentanone or heavy by products. Copper-based catalyst showed the highest selectivity for ring-rearrangement, reaching 50 mol % under the conditions investigated. The main factor influencing the yields of cyclopentanone (CPO), and promote oligomer formation, are the feed concentration and the pH, as high feed concentrations and high acidity facilitate the self-polymerization of furfuryl alcohol (FALC). This was confirmed by dedicated experiments using FALC and the hydroxypentenone intermediate as feed. The concentration challenge could be mitigated by slowly dosing the feed, which increased the desired product yields by 4–12 mol %. Nevertheless, most oligomers appeared to fall in the range of common liquid fuels and could be converted to diesel by hydrodeoxygenation.

Original languageEnglish
Article numbere202400108
JournalChemSusChem
Volume17
Issue number12
Early online date8 Feb 2024
DOIs
Publication statusPublished - 24 Jun 2024

Keywords

  • UT-Hybrid-D
  • Biomass
  • Cyclopentanone
  • Furfural
  • Humins
  • Oligomers
  • Bio jet fuel

Fingerprint

Dive into the research topics of 'Furfural to Cyclopentanone – a Search for Putative Oligomeric By-products'. Together they form a unique fingerprint.

Cite this