Use of Bisulfite Processing To Generate High-β-O-4 Content Water-Soluble Lignosulfonates
| Autor: | Christopher S. Lancefield, James R. D. Montgomery, Tomas Lebl, David B. Cordes, Reuben Carr, Daniel M. Miles-Barrett, Alexandra M. Z. Slawin, Nicholas J. Westwood |
|---|---|
| Přispěvatelé: | University of St Andrews. School of Chemistry, University of St Andrews. Biomedical Sciences Research Complex, University of St Andrews. EaSTCHEM |
| Rok vydání: | 2017 |
| Předmět: |
Softwood
General Chemical Engineering 010402 general chemistry 01 natural sciences chemistry.chemical_compound Environmental Chemistry Lignin Organic chemistry QD Lignosulfonates Biorefining Controlled depolymerization O-Benzoylation 010405 organic chemistry Renewable Energy Sustainability and the Environment Chemistry Depolymerization Bisulfite chemistry Chemical feedstocks DAS General Chemistry Nuclear magnetic resonance spectroscopy QD Chemistry 0104 chemical sciences Bisulfite Biorefineries BDC Selectivity |
| Zdroj: | Miles-Barrett, D M, Montgomery, J R D, Lancefield, C S, Cordes, D B, Slawin, A M Z, Lebl, T, Carr, R & Westwood, N J 2017, ' Use of Bisulfite Processing To Generate High-β-O-4 Content Water-Soluble Lignosulfonates ', ACS Sustainable Chemistry & Engineering . https://doi.org/10.1021/acssuschemeng.6b02566 |
| ISSN: | 2168-0485 |
| DOI: | 10.1021/acssuschemeng.6b02566 |
| Popis: | This work was supported by EPSRC grants (EP/1518175), the Industrial Biotechnology Innovation Centre (IBioIC) (DMB Ph.D. studentship) and an EPSRC Doctoral Prize Fellowship (CSL). 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. Publisher PDF |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|