Tandem catalytic depolymerization of lignin by water-tolerant Lewis acids and rhodium complexes

Robin Jastrzebski, Sandra E. Constant, Christopher S. Lancefield, Nicholas James Westwood, Bert M. Weckhuysen, Pieter C. A. Bruijnincx

Research output: Contribution to journalArticlepeer-review

68 Citations (Scopus)

Abstract

Lignin is an attractive renewable feedstock for aromatic bulk and fine chemicals production, provided that suitable depolymerization procedures are developed. Here, we describe a tandem catalysis strategy for ether linkage cleavage within lignin, involving ether hydrolysis by water-tolerant Lewis acids followed by aldehyde decarbonylation by a rhodium complex. In situ decarbonylation of the reactive aldehydes limits loss of monomers by recondensation, a major issue in acid-catalyzed lignin depolymerization. Rate of hydrolysis and decarbonylation were matched using lignin model compounds, allowing the method to be successfully applied to softwood, hardwood and herbaceous dioxasolv lignins as well as poplar sawdust to give the anticipated decarbonylation products, and, rather surprisingly, 4-(1-propenyl)phenols. Promisingly, product selectivity can be tuned by variation of Lewis acid strength and lignin source.
Original languageEnglish
Pages (from-to)2074–2079
JournalCHEMSUSCHEM
Volume9
Issue number16
Early online date21 Jul 2016
DOIs
Publication statusPublished - 23 Aug 2016

Keywords

  • Biomass
  • Decarbonylation
  • Lewis acid
  • Lignin
  • Tandem catalysis

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