Synthesis, control of substitution pattern and phase transitions of 2,3-di- O-methylcellulose

Abstract

An improved heterogeneous procedure has been found for the regioselective introduction of trityl and 4-methoxytrityl groups at the primary positions of cellulose. The 6- O-tritylcelluloses produced were completely methylated by MeI–NaOH in Me 2SO solution. The trityl groups were then completely removed to afford 2,3-di- O-methylcellulose without significant degradation of the polymer. 1H and 13C NMR spectroscopy and degradation analysis showed less than 5% deviation from the regular substitution pattern. Under optimum reaction conditions, almost perfectly regular cellulose derivatives could be obtained. Small changes in the substitution pattern had a strong effect on the phase transitions of the O-methylcelluloses in water. It was shown by DSC for the first time that perfect 2,3-di- O-methylcellulose does not undergo phase separation at elevated temperatures.