Use of bisulfite processing to generate high-β-O-4 content water-soluble lignosulfonates

Daniel M. Miles-Barrett, James R. D. Montgomery, Christopher S. Lancefield, David B. Cordes, Alexandra M. Z. Slawin, Tomas Lebl, Reuben Carr, Nicholas J. Westwood*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)
2 Downloads (Pure)

Abstract

With lignin-first biorefineries likely to become a reality, controlled depolymerization of high-quality lignin streams to high value products has become a priority. Using bisulfite chemistry, access to a high-β-O-4 content water-soluble lignosulfonate has been achieved, allowing follow-on procedures in water to be conducted. We show that phenolic β-O-4 units preferential-ly react under acidic bisulfite conditions, whilst non-phenolic β-O-4 units react much more slowly. Exploiting this improved chemical understanding and inherent selectivity, a softwood lignosulfonate has been prepared in which phenolic β-O-4 α-sulfonation has occurred leaving significant native β-O-4 content. Use of an O-benzoylation protocol with lignin coupled with advanced 2D NMR methods has allowed detailed analysis of this and other commercial and industrial lignosulfonates. Conversion of the native β-O-4 to benzylic- oxidized β-O-4 units was followed by a selective reductive cleavage to give a premium aromatic monomer in pure form.
Original languageEnglish
Pages (from-to)1831-1839
Number of pages9
JournalACS Sustainable Chemistry & Engineering
Volume5
Issue number2
Early online date18 Jan 2017
DOIs
Publication statusPublished - 6 Feb 2017

Keywords

  • Biorefineries
  • Controlled depolymerization
  • Bisulfite chemistry
  • O-Benzoylation
  • Chemical feedstocks

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