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

Jonas Simon, Lukas Fliri, Flavia Fröhlich, Janak Sapkota, Matti Ristolainen, Michael Hummel, Thomas Rosenau*, Antje Potthast*

*Tämän työn vastaava kirjoittaja

Tutkimustuotos: LehtiartikkeliArticleScientificvertaisarvioitu

2 Sitaatiot (Scopus)
17 Lataukset (Pure)

Abstrakti

Borohydride 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.

AlkuperäiskieliEnglanti
Sivut8205-8220
Sivumäärä16
JulkaisuCellulose
Vuosikerta30
Numero13
Varhainen verkossa julkaisun päivämäärä7 heinäk. 2023
DOI - pysyväislinkit
TilaJulkaistu - syysk. 2023
OKM-julkaisutyyppiA1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä

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