A Comparative Study of Structurally Related Homogeneous Ruthenium and Iron Catalysts for the Hydrogenation of Levulinic Acid to -Valerolactone

Christian A. M. R. van Slagmaat, Stefaan M. A. De Wildeman*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

The conversion of levulinic acid (LA) to -valerolactone (GVL) was investigated by employing the homogeneous Shvo catalyst (Ru-1) and iron Knolker-type catalysts, in order to evaluate the possibility to replace ruthenium with cheap, earth-abundant iron for this catalytic reaction. While the ruthenium-catalyzed reactions readily proceed, the activating agent required for the iron complex was found to interfere with the LA. This problem could be circumvented by pre-activating the original Knolker complex (Fe-1) into the corresponding dicarbonyl mono-acetonitrile iron species (Fe-3). The pre-activated iron catalyst deactivated after a few turn-overs in transfer hydrogenation reactions with isopropyl alcohol; however, highly improved GVL yields were achieved under H-2 pressure to a notable maximum of 570 turn-overs for Fe-3. Nevertheless, comparative screening experiments with various solvents and kinetic studies showed that Ru-1 is still superior over Fe-3 in terms of catalytic activity.
Original languageEnglish
Pages (from-to)694-702
Number of pages9
JournalEuropean Journal of Inorganic Chemistry
Issue number6
DOIs
Publication statusPublished - 14 Feb 2018

Keywords

  • Ruthenium
  • Iron
  • Homogeneous catalysis
  • Hydrogenation
  • Levulinic acid
  • COOPERATIVE TRANSITION-METAL
  • LIGAND-EXCHANGE REACTION
  • SITU GENERATED CATALYST
  • GAMMA-VALEROLACTONE
  • ENANTIOSELECTIVE HYDROGENATION
  • FORMIC-ACID
  • ASYMMETRIC HYDROGENATION
  • HETEROGENEOUS CATALYSTS
  • FRUCTOSE DEHYDRATION
  • TRANSPORTATION FUELS

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