Use of bisulfite processing to generate high-β-O-4 content water-soluble lignosulfonates
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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.
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 , vol. 5 , no. 2 , pp. 1831-1839 . DOI: 10.1021/acssuschemeng.6b02566
ACS Sustainable Chemistry & Engineering
Copyright © 2016 American Chemical Society. This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
DescriptionThis 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).
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