Synthesis of Chlorodeoxycellulose and its Conversion to 5,6-Cefluloseen

Abstract

Reaction of cellulose acetate with methylsulfonyl chloride in N,N-dimethylformamide has been studied under different conditions of time, temperature and concentration of the reagent. Using this method, chlorodeoxycellulose of a D.S. as high as 0.58 has been prepared. The reaction has also been applied to purified cotton linters to yield chlorodeoxycellulose. Attempts to prepare this cellulose derivative by reaction of cellulose acetate with acetyl chloride, anhydrous aluminum chloride and magnesium chloride in N,N-dimethylformamide were unsuccessful. 5, 6-celluloseen is obtained by dehydrohalogenation of the chlorodeoxycelluloses either with dry methanolic potassium hydroxide or with potassium tert. butoxide in dimethyl sulfoxide. With the latter reagent the conversion of chloro deoxycellulose to celluloseen is almost quantitative.