ATTEMPTED LOCATION OF THE SUBSTITUENT IN CELLULOSE XANTHATE BY NEW METHODS

Abstract

Cellulose sodium xanthate of degree of substitution (D.S.) about 0.4 was methylated in 91% to 96% yield by methyl iodide in ether or benzene to the corresponding white S-methyl xanthate. This S-methyl xanthate was partly hydrolyzed, less than 40% of the substituent being incidentally lost, and the hydrolyzate was chromatographed on paper. About 20% of glucose was recovered together with two substances recognized as characteristic hydrolytic products of glucose 6-S-methyl xanthate. The procedure was not quantitative for xanthate groups in the primary alcohol positions of cellulose, and was too drastic to yield information about the less stable groups in the secondary positions.The acetylation of the above cellulose S-methyl xanthate with acetic anhydride and pyridine led to a near-white, fibrous, fully acetylated product with unaltered xanthate substitution. Repeated attempts to remove the S-methyl xanthate groups by reaction with heavy metals or their salts, or with sodium chlorite, resulted in the simultaneous removal of about the same number of acetyl groups.