Insights into the borohydride reduction of dialdehyde cellulose: the dilemma of competing reduction and β-elimination reactions

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dc.contributorAalto-yliopistofi
dc.contributorAalto Universityen
dc.contributor.authorSimon, Jonasen_US
dc.contributor.authorFliri, Lukasen_US
dc.contributor.authorFröhlich, Flaviaen_US
dc.contributor.authorSapkota, Janaken_US
dc.contributor.authorRistolainen, Mattien_US
dc.contributor.authorHummel, Michaelen_US
dc.contributor.authorRosenau, Thomasen_US
dc.contributor.authorPotthast, Antjeen_US
dc.contributor.departmentDepartment of Bioproducts and Biosystemsen
dc.contributor.groupauthorBiopolymer Chemistry and Engineeringen
dc.contributor.organizationUniversity of Natural Resources and Life Sciences, Viennaen_US
dc.contributor.organizationUPM Research Centeren_US
dc.date.accessioned2023-10-25T07:36:47Z
dc.date.available2023-10-25T07:36:47Z
dc.date.issued2023-09en_US
dc.descriptionFunding Information: Open access funding provided by University of Natural Resources and Life Sciences Vienna (BOKU). The financial support by Business Finland, UPMKymmene Oyj (Finland), the Austrian Biorefinery Center Tulln (ABCT), and the doctoral school “Advanced Biorefineries: Chemistry & Materials” (ABC&M) is gratefully acknowledged. Publisher Copyright: © 2023, The Author(s).
dc.description.abstractBorohydride reduction of dialdehyde cellulose (DAC) is a promising strategy to generate dialcohol cellulose as bio-based alternative to petroleum-based materials. However, the degradation of the polymer backbone according to β-elimination mechanisms limits the practical applications of the reaction. Therefore, we aimed at optimizing the process to suppress degradation reactions by varying reaction time, pH, and reagent stoichiometry. The degree of oxidation (DO) of the DAC intermediates significantly impacts the yields and molecular weights of the isolated dialcohol celluloses, with a “leveling-off” effect at higher DO values. Increasing the amount of sodium borohydride can minimize—but not entirely prevent—chain scissions. Lowering the pH value during reduction slows down the degradation but results in incomplete conversion of the aldehyde functionalities. Our study provides valuable insights into the consequences of side reactions during borohydride reduction of DAC as well as into chemistry and analysis of the dialdehyde cellulose/dialcohol cellulose system. Graphical abstract: About a dilemma in cellulose chemistry: Dialcohol cellulose derived by periodate oxidation and subsequent borohydride reduction of cellulose has received increasing attention in the development of sustainable thermoplastic materials. The present study highlights the challenge of suppressing β-elimination and favoring the reduction pathway to optimize reaction conditions and minimize chain degradation.en
dc.description.versionPeer revieweden
dc.format.extent16
dc.format.extent8205-8220
dc.format.mimetypeapplication/pdfen_US
dc.identifier.citationSimon, J, Fliri, L, Fröhlich, F, Sapkota, J, Ristolainen, M, Hummel, M, Rosenau, T & Potthast, A 2023, ' Insights into the borohydride reduction of dialdehyde cellulose: the dilemma of competing reduction and β-elimination reactions ', Cellulose, vol. 30, no. 13, pp. 8205-8220 . https://doi.org/10.1007/s10570-023-05350-1en
dc.identifier.doi10.1007/s10570-023-05350-1en_US
dc.identifier.issn0969-0239
dc.identifier.issn1572-882X
dc.identifier.otherPURE UUID: c8352c7a-ee97-471e-81e3-5e3ea0f59b51en_US
dc.identifier.otherPURE ITEMURL: https://research.aalto.fi/en/publications/c8352c7a-ee97-471e-81e3-5e3ea0f59b51en_US
dc.identifier.otherPURE LINK: http://www.scopus.com/inward/record.url?scp=85164191297&partnerID=8YFLogxKen_US
dc.identifier.otherPURE FILEURL: https://research.aalto.fi/files/125302630/CHEM_Simon_et_al_Insights_into_the_borohydride_2023_Cellulose.pdfen_US
dc.identifier.urihttps://aaltodoc.aalto.fi/handle/123456789/124281
dc.identifier.urnURN:NBN:fi:aalto-202310256654
dc.language.isoenen
dc.publisherSpringer
dc.relation.ispartofseriesCelluloseen
dc.relation.ispartofseriesVolume 30, issue 13en
dc.rightsopenAccessen
dc.subject.keywordCelluloseen_US
dc.subject.keywordDialdehyde celluloseen_US
dc.subject.keywordGel permeation chromatographyen_US
dc.subject.keywordPeriodate oxidationen_US
dc.subject.keywordReductionen_US
dc.subject.keywordRenewable resourcesen_US
dc.subject.keyword“Level-off” DPen_US
dc.titleInsights into the borohydride reduction of dialdehyde cellulose: the dilemma of competing reduction and β-elimination reactionsen
dc.typeA1 Alkuperäisartikkeli tieteellisessä aikakauslehdessäfi
dc.type.versionpublishedVersion
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