The reaction of cellulose nitrate with several nucleophiles

Replacement of the nitrate groups in cellulose nitrate (CN) to varying degrees by azide, bromide, iodide, thiocyanate, or nitro groups was accomplished by heating with the corresponding alkali-metal salt in organic solvents. Extensive chain degradation also occurred, increasing with the nitrogen content of the CN used, and with the alkalinity of the reagent; this was the sole reaction with sodium cyanide. A simplified procedure for preparing CN containing less than 10% nitrogen is described.