Reductive amination of 5-acetoxymethylfurfural over Pt/Al2O3 catalyst in a flow reactor

Alexey L. Nuzhdin, Pavel A. Simonov, Galina A. Bukhtiyarova, Ilia V. Eltsov, Valerii I. Bukhtiyarov

Research output: Contribution to journalArticlepeer-review

Abstract

Aminomethylhydroxymethylfuran derivatives are well known for their pharmaceutical activities. In this work, the two-step one-pot procedure for the synthesis of N-substituted 5-(acetoxymethyl)-2-furfuryl amines was proposed, which includes two successive reactions: the condensation of 5-acetoxymethylfurfural (AMF) with primary amines and the reduction of obtained imines with hydrogen over supported metal catalysts in a flow reactor. The comparison of the properties of Au, Pd and Pt catalysts in the hydrogenation of imine obtained by reaction of AMF with aniline showed that Pt-based catalysts (both Pt/Al2O3 and Pt/C) are highly active and provide high selectivity and stability, while Pd and Au nanoparticles supported on γ-alumina and carbon show low selectivity. A wide range of N-substituted 5-(acetoxymethyl)-2-furfuryl amines was synthesized in good to excellent yields using Pt/Al2O3 catalyst and methanol as a solvent.

Original languageEnglish
Article number111297
Number of pages5
JournalMolecular Catalysis
Volume499
Early online date19 Nov 2020
DOIs
Publication statusPublished - Jan 2021

Keywords

  • 5-Acetoxymethylfurfural
  • Flow hydrogenation
  • Primary amines
  • Pt/AlOcatalyst
  • Reductive amination
  • Pt/Al(2)O(3)catalyst
  • HYDROGENATION
  • AMINES
  • BIOMASS
  • ALDEHYDES
  • UTILITY

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