Synthesis of some new esters and ethers of cellulose and examination of their properties

A new method has been devised for the synthesis of normal esters of cellulose and carbonic acid by reaction of cellulose alcoholate and methyl chlorocarbonate: A normal ester of cellulose with monothiocarbonic acid has been prepared analogously as follows: A disulfide has been prepared by oxidation of the sodium salt of the thioester with iodine: A comparison was made of the stabilities toward various reagents of cellulose esters of carbonic, normal thiocarbonic, and dithiocarbonic acid and also of the acid and neutral esters of cellulose and monothiocarbonic acid. It was found that the stabilities of the esters toward acids and bases as well as to light and heat very considerably with the nature of the acid grouping introduced. A method has been worked out for the synthesis of phenyl esters of cellulose by the reaction of sodium phenoxide with p‐toluenesulfonylesters of cellulose: \documentclass{article}\pagestyle{empty}\begin{document}$$ {\rm Cell - OSO}_{\rm 2} {\rm C}_{\rm 6} {\rm H}_{\rm 4} {\rm CH}_{\rm 3} + {\rm C}_{\rm 6} {\rm H}_{\rm 5} {\rm ONa} \to {\rm cell - OC}_6 {\rm H}_{\rm 5} + {\rm CH}_3 {\rm C}_6 {\rm H}_4 {\rm SO}_2 {\rm ONa} $$\end{document} A phenyl ester of cellulose (γ = 70–80) has been prepared and its properties investigated. It was shown that by this procedure the phenyl group is introduced into position 6.