Unconventional cellulose products by fluorination of tosyl cellulose

The synthesis of novel deoxy-fluoro cellulose derivatives obtained by nucleophilic displacement reactions (SN) of p-toluenesulfonyl (tosyl) cellulose with tetrabutylammonium fluoride (TBAF) is described. Detailed studies concerning the influence of the reaction time and temperature as well as the water content of the TBAF on the composition of the products were carried out. The SN reaction occurs even at room temperature. The degree of substitution of deoxy-fluoro moieties (DSF) is in the range from 0.22 to 0.47. The polymers contain remaining tosyl groups. Preliminary 19F NMR measurements reveal the presence of the CH2F group. The degradation temperature of the deoxy-fluoro cellulose derivatives is increased compared to the starting tosyl cellulose, however, a distinct influence of the remaining tosyl groups appears.