Synthesis of 3,6-anhydro derivatives of cellulose by saponification of the tosyl ester of cellulose with aqueous alkali solutions

Abstract

IN PREVIOUS work [1, 2], a description has been given of the synthesis of bicyclic derivatives of cellulose containing the 3,6-anhydro ring in the elementary unit of the macromolecule, the derivatives being obtained by saponification of cellulose tosylate and tosylacetate with alcoholic alkali solutions. In the arrhydro derivatives of cellulose obtained by this method, the a-oxide rings formed as a result of the saponification of the secondary sulphonyloxyl groups were opened up by the C:H30-ion with the formation of methyl esters of a mixed polysaccharide. As distinct from these compounds, the product of the saponification of cellulose tosylate with aqueous alkali should take the form of a mixed polysaccharide containing only the following elementary units: 3,6-anhydro glucose, glucose and altrose (from the opening of a-oxide rings with rotation of the configuration). In this article, experimental data: are presented about the synthesis of 3,6-anhydro cellulose by saponification of cellulose tosylate with aqueous alkali solutions according to the mechanism