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Efficient and catalyst-free synthesis of cellulose acetoacetates

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Abstract

An efficient path to prepare cellulose acetoacetates is reviewed in detail. The biopolymer dissolved in N,N-dimethylacetamide-LiCl is allowed to react with 2,2,6-trimethyl-4H-1,3-dioxin-4-one at elevated temperatures without any catalyst. The procedure, which is briefly described in the literature (Marson and El Seoud in J Appl Polym Sci 74:1355–1360, 1999), utilizes simple to handle, commercially available compounds and requires only a short reaction time to obtain pure products that are promising starting materials for the design of advanced cellulose-based materials. Cellulose acetoacetates with degree of substitution of up to 1.84 can be obtained. A side reaction forming comb-like polymer structures was realized applying high molar ratio of cellulose to reagent (above 2 mol per mol) that was not known up to now. The hydrophobic cellulose acetoacetates can be transferred easily into nanoparticles with particle sizes ranging from 120 to 300 nm.

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Acknowledgments

The authors would like to thank Steffi Stumpf from the group of Prof. U.S. Schubert (Center for Soft Matter, Jena Germany) for the SEM images. The SEM/TEM facilities of the Jena Center for Soft Matter (JCSM) were established with a Grant from the German Research Council (DFG) and the European Funds for Regional Development (EFRE). The studies were financially supported by the DFG-funded Collaborative Research Centre PolyTarget (SFB 1278, Project A02).

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Authors and Affiliations

  1. Institute for Organic Chemistry and Macromolecular Chemistry, Center of Excellence for Polysaccharide Research, Friedrich Schiller University of Jena, Humboldtstraße 10, 07743, Jena, Germany

    Hendryk Würfel, Marvin Kayser & Thomas Heinze

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  1. Hendryk Würfel
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  2. Marvin Kayser
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  3. Thomas Heinze
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Correspondence to Thomas Heinze.

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Member of European Polysaccharide Network of Excellence (EPNOE, http://www.epnoe.eu).

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Würfel, H., Kayser, M. & Heinze, T. Efficient and catalyst-free synthesis of cellulose acetoacetates. Cellulose 25, 4919–4928 (2018). https://doi.org/10.1007/s10570-018-1908-y

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  • DOI: https://doi.org/10.1007/s10570-018-1908-y

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