Insight into the hydrophobic functionalization of cellulose microfibrils using the Passerini three-component reaction.

Autor: Hamzah O; Univ. Grenoble Alpes, CNRS, CERMAV, F-38000 Grenoble, France., Vandenbrouck T; Univ. Grenoble Alpes, CNRS, CERMAV, F-38000 Grenoble, France., Heux L; Univ. Grenoble Alpes, CNRS, CERMAV, F-38000 Grenoble, France., Jean B; Univ. Grenoble Alpes, CNRS, CERMAV, F-38000 Grenoble, France. Electronic address: bruno.jean@cermav.cnrs.fr.
Jazyk: angličtina
Zdroj: Carbohydrate polymers [Carbohydr Polym] 2024 Oct 01; Vol. 341, pp. 122323. Date of Electronic Publication: 2024 May 26.
DOI: 10.1016/j.carbpol.2024.122323
Abstrakt: The aqueous catalyst-free one-pot Passerini 3-component reaction (P-3CR) was employed for the functionalization of dialdehyde cellulose (DAC) derived from the periodate oxidation of microfibrillated cellulose (MFC) with insights provided by 13 C and 15 N CP-MAS NMR and FTIR analyses. The kinetics of the P-3CR revealed rapid progress within the initial 2 h, reaching a plateau between 6 and 18 h. The reaction achieved a maximum degree of substitution (DS) with only 1 equivalent of carboxylic acid and isocyanide with respect to the number of aldehydes, therefore demonstrating the atom economy character of the P-3CR performed on MFC. Variable DS values (0.08 to 0.37) were achieved by altering the degree of oxidation of DAC (ranging from 0.48 to 1.1) when reacted with heptanoic acid and tert-butyl isocyanide. Additionally, aliphatic chain lengths of carboxylic acids from C4 to C11 were successfully used for the functionalization of DAC with distinct hydrophobic chains. Furthermore, while cosolvents negatively affected the DS when using heptanoic acid, a significant increase was observed in the case of undecanoic acid due to an improved solubility of the reagent. The aqueous medium P-3CR can thus be considered a versatile tool to tailor the functionalization of MFC and provide it with hydrophobicity.
Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
(Copyright © 2024 The Authors. Published by Elsevier Ltd.. All rights reserved.)
Databáze: MEDLINE
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