Recent Catalytic Advances on the Sustainable Production of Primary Furanic Amines from the One-Pot Reductive Amination of 5-Hydroxymethylfurfural

ChemSusChem. 2023 Jan 9;16(1):e202201846. doi: 10.1002/cssc.202201846. Epub 2022 Nov 27.

Abstract

5-Hydroxymethylfurfural (5-HMF) represents a well-known class of lignocellulosic biomass-derived platform molecules. With the presence of many reactive functional groups in the structure, this versatile building block could be valorized into many value-added products. Among well-established catalytic transformations in biorefinery, the reductive amination is of particular interest to provide valuable N-containing compounds. Specifically, the reductive amination of 5-HMF with ammonia (NH3 ) and molecular hydrogen (H2 ) offers a straightforward and sustainable access to primary furanic amines [i. e., 5-hydroxymethyl-2-furfuryl amine (HMFA) and 2,5-bis(aminomethyl)furan (BAMF)], which display far-reaching utilities in pharmaceutical, chemical, and polymer industries. In the presence of heterogeneous catalysts contanining monometals (Ni, Co, Ru, Pd, Pt, and Rh) or bimetals (Ni-Cu and Ni-Mn), this elegant pathway enables a high-yielding and chemoselective production of HMFA/BAMF compared to other synthetic routes. This Review aims to present an up-to-date highlight on the supported metal-catalyzed reductive amination of 5-HMF with elaborate studies on the role of metal, solid support, and reaction parameters. Besides, the recyclability/adaptability of catalysts as well as the reaction mechanism are also provided to give valuable insights into this potential 5-HMF valorization strategy.

Keywords: 5-hydroxymethylfurfural; biomass; heterogeneous catalysis; reductive amination; sustainable chemistry.

Publication types

  • Review

MeSH terms

  • Amination
  • Amines* / chemistry
  • Catalysis
  • Furaldehyde* / chemistry

Substances

  • Amines
  • 5-hydroxymethylfurfural
  • Furaldehyde