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Efficient allylation of cellulose in dimethyl sulfoxide/tetrabutylammonium fluoride trihydrate

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Abstract

The cellulose solvent dimethyl sulfoxide (DMSO)/tetrabutylammonium fluoride trihydrate (TBAF) was successfully applied as reaction medium for the synthesis of allyl cellulose by conversion of the polymer with allyl chloride in the presence of solid NaOH. Samples with degree of substitution from 0.50 to 2.98 were accessible by varying the molar ratio anhydroglucose unit:allyl chloride:NaOH and reaction time. DMSO/TBAF was found to be an efficient reaction medium for the preparation of highly functionalized samples from spruce sulfite pulp with degree of polymerization of about 500 even in a scale of 50 g. The allyl cellulose samples were characterized by means of FTIR- and NMR spectroscopy. Size exclusion chromatography revealed negligible polymer degradation during synthesis and purification of the samples.

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Authors and Affiliations

  1. Center of Excellence for Polysaccharide Research, Friedrich Schiller University of Jena, Humboldtstrasse 10, 07743, Jena, Germany

    Thomas Heinze, Thorger Lincke, Dominik Fenn & Andreas Koschella

Authors
  1. Thomas Heinze
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  2. Thorger Lincke
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  3. Dominik Fenn
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  4. Andreas Koschella
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Correspondence to Thomas Heinze.

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Heinze, T., Lincke, T., Fenn, D. et al. Efficient allylation of cellulose in dimethyl sulfoxide/tetrabutylammonium fluoride trihydrate . Polym. Bull. 61, 1–9 (2008). https://doi.org/10.1007/s00289-008-0919-5

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  • DOI: https://doi.org/10.1007/s00289-008-0919-5

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