Synthesis of soluble cellulose tosylates in an eco-friendly medium

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.