Solvent-Free Acetylation of Cellulose by 1‑Ethyl-3-methylimidazolium Acetate-Catalyzed Transesterification

Cellulose acetate is one of the oldest synthetic thermoplastic polymers and has various applications including usage as films, fibers, and membrane products. Traditionally, cellulose acetate is prepared by reacting cellulose with acetic anhydride in acetic acid using sulfuric acid as a catalyst. Thi...

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Bibliographic Details
Published in:ACS sustainable chemistry & engineering 2019-10, Vol.7 (20), p.16971-16978
Main Authors: Chen, Mingjie, Li, Rui-Min, Runge, Troy, Feng, Jin, Feng, Jing, Hu, Songnan, Shi, Qing-Shan
Format: Article
Language:English
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Summary:Cellulose acetate is one of the oldest synthetic thermoplastic polymers and has various applications including usage as films, fibers, and membrane products. Traditionally, cellulose acetate is prepared by reacting cellulose with acetic anhydride in acetic acid using sulfuric acid as a catalyst. This process suffers from extensive depolymerization of the cellulose molecules and corrosion of the equipment from the use of the acidic solvent and catalyst. Herein we present an acid-free cellulose acetylation process using vinyl acetate as both the reactant and reaction medium and 1-ethyl-3-methylimidazolium acetate as the catalyst. The obtained cellulose acetate was confirmed by FTIR, NMR, and XRD studies. Additionally, the reaction kinetics, mechanism of the process, and properties of the obtained cellulose acetate were studied. Cellulose triacetate was obtained by our process within 2 h at 90 °C. The reaction kinetics was described with the classical pseudo-first-order rate expression of heterogeneous cellulose acetylation. The reaction mechanism was shown to be a peel-off mechanism similar to that of cellulose acetylation by the traditional acetic acid process. The molecular weight of the cellulose acetate produced by this new process was significantly higher than that from the traditional acetic acid process because of the absence of strong acids, which can depolymerize cellulose. In summary, we describe a new acid-free process to produce cellulose acetate that limits cellulose depolymerization and avoids the use of corrosive chemicals.
ISSN:2168-0485
2168-0485
DOI:10.1021/acssuschemeng.8b06333