Isolation of functionalized phenolic monomers through selective oxidation and C—O bond cleavage of the β-O-4 linkages in lignin

Christopher S Lancefield, O Stephen Ojo, Fanny Tran, Nicholas J Westwood

Research output: Contribution to journalArticlepeer-review

304 Citations (Scopus)

Abstract

Functionalized phenolic monomers have been generated and isolated from an organosolv lignin through a two-step depolymerization process. Chemoselective catalytic oxidation of β-O-4 linkages promoted by the DDQ/tBuONO/O2 system was achieved in model compounds, including polymeric models and in real lignin. The oxidized β-O-4 linkages were then cleaved on reaction with zinc. Compared to many existing methods, this protocol, which can be achieved in one pot, is highly selective, giving rise to a simple mixture of products that can be readily purified to give pure compounds. The functionality present in these products makes them potentially valuable building blocks.
Original languageEnglish
Pages (from-to)258-262
Number of pages5
JournalAngewandte Chemie
Volume54
Issue number1
Early online date5 Nov 2014
DOIs
Publication statusPublished - 2 Jan 2015

Keywords

  • Biomass
  • Depolymerization
  • Lignin
  • Oxidation
  • Renewable chemicals

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