A facile method for the homogeneous synthesis of cyanoethyl cellulose in NaOH/urea aqueous solutions

A series of cyanoethyl cellulose (CEC) samples were synthesized from cellulose in NaOH/urea aqueous solutions by a homogeneous method. Structure and properties of CECs were characterized with FT-IR, 1H and 13C NMR, DSC, SEC-LLS, polarized light microscopy and solubility measurements. The total DS values of the obtained CECs were in the range of 0.26 to 1.93, and the relative reactivity of hydroxyl groups is in the order C-6 > C-2 > C-3. As the molar ratio of acrylonitrile to anhydroglucose unit (AGU) of cellulose increased to 5 : 1, the C-6 hydroxyl groups of AGU were fully substituted. The total DS value for water-soluble CEC is as low as 0.54. CEC could be dissolved in many organic solvents when its total DS value reached 1.37. Organic-soluble CEC samples displayed thermotropic liquid crystalline behavior in the temperature range of 180 to 280 °C. Moreover, NaOH/urea aqueous solution was proved to be a stable medium for cyanoethylation of cellulose, the reaction products could be easy isolated and purified, and the solvents could be recycled by a simple filtration. Therefore, this work provides a facile method for the homogeneous synthesis of CEC in an aqueous system.