Skip to content

Research at St Andrews

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

Research output: Contribution to journalArticle

Author(s)

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

School/Research organisations

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.
Close

Details

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

    Research areas

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

Discover related content
Find related publications, people, projects and more using interactive charts.

View graph of relations

Related by author

  1. The synthesis and analysis of lignin-bound Hibbert ketone structures in technical lignins

    Miles-Barrett, D., Neal, A., Hand, C., Montgomery, J., Panovic, I., Ojo, O. S., Lancefield, C. S., Cordes, D. B., Slawin, A. M. Z., Lebl, T. & Westwood, N. J., 14 Nov 2016, In : Organic & Biomolecular Chemistry. 14, 42, p. 10023-10030 8 p.

    Research output: Contribution to journalArticle

  2. Synthesis of the natural product descurainolide and cyclic peptides from lignin-derived aromatics

    Ojo, O. S., Nardone, B., Musolino, S. F., Neal, A., Wilson, L., Lebl, T., Slawin, A. M. Z., Cordes, D. B., Taylor, J. E., Naismith, J. H., Smith, A. D. & Westwood, N. J., 14 Jan 2018, In : Organic & Biomolecular Chemistry. 16, 2, p. 266-273

    Research output: Contribution to journalArticle

  3. Total synthesis of dehaloperophoramidine using a highly diastereoselective Hosomi-Sakurai reaction

    Wilkie, R. P., Neal, A., Johnston, C. A., Voûte, N., Lancefield, C. S., Stell, M., Medda, F., Makiyi, E. F., Turner, E., Ojo, O. S., Slawin, A. M. Z., Lebl, T., Mullen, P., Harrison, D. J., Ireland, C. M. & Westwood, N. J., 14 Sep 2016, In : Chemical Communications. 52, 71, p. 10747-10750

    Research output: Contribution to journalArticle

  4. Advanced model compounds for understanding acid-catalyzed lignin depolymerization: identification of renewable aromatics and a lignin-derived solvent

    Lahive, C., Deuss, P. J., Lancefield, C. S., Sun, Z., Cordes, D. B., Young, C. M., Tran, F., Slawin, A. M. Z., de Vries, J. G., Kamer, P. C. J., Westwood, N. J. & Barta, K., 20 Jul 2016, In : Journal of the American Chemical Society. 138, 28, p. 8900-8911 12 p.

    Research output: Contribution to journalArticle

Related by journal

  1. Mild organosolv lignin extraction with alcohols: the importance of benzylic alkoxylation

    Zijlstra, D. S., Lahive, C., Analbers, C. A., Figueiredo, M. B., Wang, Z., Lancefield, C. & Deuss, P. J., 6 Apr 2020, In : ACS Sustainable Chemistry & Engineering . 8, 13, p. 5119-5131 13 p.

    Research output: Contribution to journalArticle

  2. Preparation and reaction of β-O-4 γ-aldehyde-containing butanosolv lignins

    Panovic, I., Miles-Barrett, D. M., Lancefield, C. S. & Westwood, N. J., 15 Jul 2019, In : ACS Sustainable Chemistry and Engineering. 7, 14, p. 12098-12104 7 p.

    Research output: Contribution to journalArticle

  3. Artificial metalloenzymes as catalysts for oxidative lignin degradation

    Doble, M., Jarvis, A., Ward, A., Colburn, J. D., Goetze, J. P., Buehl, M. & Kamer, P. C. J., 5 Nov 2018, In : ACS Sustainable Chemistry & Engineering . 6, 11, p. 15100-15107 8 p.

    Research output: Contribution to journalArticle

  4. Grafting of technical lignins through regioselective triazole formation on β-O-4 linkages

    Panovic, I., Montgomery, J. R. D., Lancefield, C. S., Puri, D., Lebl, T. & Westwood, N. J., 13 Sep 2017, In : ACS Sustainable Chemistry & Engineering . 5, 11, p. 16040-10648

    Research output: Contribution to journalArticle

  5. Quantification and classification of carbonyls in industrial humins and lignins by 19F NMR

    Constant, S., Lancefield, C. S., Weckhuysen, B. M. & Bruijnincx, P. C. A., 3 Jan 2017, In : ACS Sustainable Chemistry and Engineering. 5, 1, p. 965-972 8 p.

    Research output: Contribution to journalArticle

ID: 248657266

Top