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Application of the solvent dimethyl sulfoxide/tetrabutyl-ammonium fluoride trihydrate as reaction medium for the homogeneous acylation of Sisal cellulose

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Abstract

Two types of Sisal cellulose were studied as starting material for homogeneous acylation in the solvent dimethyl sulfoxide (DMSO)/tetrabutylammonium fluoride trihydrate (TBAF). The native Sisal cellulose investigated contains 14% hemicellulose (mainly composed of xylose) as confirmed by 13C-NMR spectroscopy in DMSO-d6/TBAF and HPLC analysis after complete polymer degradation. Alkali treatment of Sisal cellulose decreases the amount of hemicellulose, the degree of polymerization and the crystallinity. Both Sisal cellulose samples can be dissolved in DMSO/TBAF after treatment at elevated temperature. GPC measurements showed high aggregation in the solution. Different homogeneous acylation reactions using carboxylic acid anhydrides and vinyl esters were carried out, showing a pronounced tendency of the anhydride towards hydrolysis in the solvent. This disadvantage can be diminished by decreasing the amount of the salt hydrate (TBAF trihydrate) or by a distillative removal of the majority of water. A strong interaction of the polymer with the water in the solvent was observed.

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Authors and Affiliations

  1. Institut für Organische Chemie und Makromolekulare Chemie, Friedrich-Schiller-Universität Jena, Humboldtstrasse 10, D-07743, Jena, Germany

    Gabriela T. Ciacco, Tim F. Liebert & Thomas J. Heinze

  2. Instituto de Química de São Carlos, Universidade de São Paulo, Cx. P. 780, São Carlos, CEP 13560-970, Brazil

    Gabriela T. Ciacco & Elisabete Frollini

  3. FB 9 (Chemie), Bergische Universität Wuppertal, Gauß Strasse 20, D-42097, Wuppertal, Germany

    Thomas J. Heinze

Authors
  1. Gabriela T. Ciacco
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  2. Tim F. Liebert
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  3. Elisabete Frollini
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  4. Thomas J. Heinze
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Correspondence to Thomas J. Heinze.

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Ciacco, G.T., Liebert, T.F., Frollini, E. et al. Application of the solvent dimethyl sulfoxide/tetrabutyl-ammonium fluoride trihydrate as reaction medium for the homogeneous acylation of Sisal cellulose. Cellulose 10, 125–132 (2003). https://doi.org/10.1023/A:1024064018664

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  • DOI: https://doi.org/10.1023/A:1024064018664

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