Synthesis of soluble cellulose tosylates in an eco-friendly medium

S. Schmidt; T. Liebert; T. Heinze

doi:10.1039/C3GC41994K

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Synthesis of soluble cellulose tosylates in an eco-friendly medium†

S. Schmidt,^a T. Liebert^a and T. Heinze*^a

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* Corresponding authors

^a Center of Excellence for Polysaccharide Research, Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University of Jena, Humboldtstraße 10, D-07743 Jena, Germany
E-mail: thomas.heinze@uni-jena.de
Fax: +49 3641 94 8272

Abstract

The tosylation of cellulose in the eco-friendly solvent NaOH–urea in the presence of the nonionic surfactant polyethylene glycol alkyl-(C₁₁–C₁₅) ether (Imbentin) yields well soluble p-toluenesulfonic acid esters of cellulose (tosyl cellulose). The influence of reaction time, temperature, and molar ratio on the degree of substitution (DS) was studied. The products were characterized by means of NMR- and FTIR-spectroscopy, elemental analysis and size exclusion chromatography. Moreover, 6-deoxy-6-azido-, 6-deoxy-6-(ω-aminoethyl)amino-, and 6-deoxy-6-thiosulfate cellulose could be prepared by nucleophilic displacement (S_N) of the tosyl groups.

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Article information

DOI: https://doi.org/10.1039/C3GC41994K
Article type: Paper
Submitted: 24 Sep 2013
Accepted: 02 Dec 2013
First published: 02 Dec 2013

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Green Chem., 2014,16, 1941-1946

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Synthesis of soluble cellulose tosylates in an eco-friendly medium

S. Schmidt, T. Liebert and T. Heinze, Green Chem., 2014, 16, 1941 DOI: 10.1039/C3GC41994K

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Green Chemistry

Synthesis of soluble cellulose tosylates in an eco-friendly medium†

Abstract

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Synthesis of soluble cellulose tosylates in an eco-friendly medium

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