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dc.contributor.authorMiles-Barrett, Daniel M.
dc.contributor.authorMontgomery, James R. D.
dc.contributor.authorLancefield, Christopher S.
dc.contributor.authorCordes, David B.
dc.contributor.authorSlawin, Alexandra M. Z.
dc.contributor.authorLebl, Tomas
dc.contributor.authorCarr, Reuben
dc.contributor.authorWestwood, Nicholas J.
dc.date.accessioned2017-03-13T11:30:08Z
dc.date.available2017-03-13T11:30:08Z
dc.date.issued2017-02-06
dc.identifier.citationMiles-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 . https://doi.org/10.1021/acssuschemeng.6b02566en
dc.identifier.issn2168-0485
dc.identifier.otherPURE: 248657266
dc.identifier.otherPURE UUID: 4de4076a-54f8-4d93-9e68-6a544d76a1f9
dc.identifier.otherScopus: 85011655549
dc.identifier.otherORCID: /0000-0002-0269-3221/work/48131703
dc.identifier.otherORCID: /0000-0002-5366-9168/work/29246559
dc.identifier.otherORCID: /0000-0003-0630-0138/work/56424141
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861506
dc.identifier.urihttp://hdl.handle.net/10023/10458
dc.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).en
dc.description.abstractWith 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.
dc.format.extent9
dc.language.isoeng
dc.relation.ispartofACS Sustainable Chemistry & Engineeringen
dc.rightsCopyright © 2016 American Chemical Society. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at: https://doi.org/10.1021/acssuschemeng.6b02566en
dc.rightsCopyright © 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.en
dc.subjectBiorefineriesen
dc.subjectControlled depolymerizationen
dc.subjectBisulfite chemistryen
dc.subjectO-Benzoylationen
dc.subjectChemical feedstocksen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleUse of bisulfite processing to generate high-β-O-4 content water-soluble lignosulfonatesen
dc.typeJournal articleen
dc.description.versionPostprinten
dc.description.versionPostprinten
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.contributor.institutionUniversity of St Andrews.Biomedical Sciences Research Complexen
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.identifier.doihttps://doi.org/10.1021/acssuschemeng.6b02566
dc.description.statusPeer revieweden


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