Journal
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
Volume 5, Issue 2, Pages 1831-1839Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acssuschemeng.6b02566
Keywords
Biorefineries; Controlled depolymerization; Bisulfite chemistry; O-Benzoylation; Chemical feedstocks
Categories
Funding
- EPSRC [EP/1518175]
- Industrial Biotechnology Innovation Centre (IBioIC)
- EPSRC Doctoral Prize Fellowship
- Engineering and Physical Sciences Research Council [1654168, 1518175] Funding Source: researchfish
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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-beta-O-4 content watersoluble lignosulfonate has been achieved, allowing follow-up procedures in water to be conducted. We show that phenolic beta-O-4 units preferentially react under acidic bisulfite conditions, while nonphenolic beta-O-4 units react much more slowly. Exploiting this improved chemical understanding and inherent selectivity, we have prepared a softwood lignosulfonate in which phenolic beta-O-4 a-sulfonation has occurred, leaving significant native beta-O-4 content. Use of an O-benzoylation protocol with lignin coupled with advanced two-dimensional nuclear magnetic resonance methods has allowed detailed analysis of this and other commercial and industrial lignosulfonates. Conversion of the native beta-O-4 to benzylic, oxidized beta-O-4 units was followed by a selective reductive cleavage to give a premium aromatic monomer in pure form.
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