Distribution of substituent groups in O-(2-aminoethyl)cellulose

Abstract
O-(2-Aminoethyl)cellulose (degree of substitution 0.14), prepared by reaction of sodium 2-aminoethyl sulfate with cotton fabric, was hydrolyzed to glucose and mono-O-(2-aminoethyl)-D-glucopyranoses which were identified by gas–liquid chromatography (g.l.c.). Complications arise from reactions between the functional group at C-1 of the glucose unit and the amine function of a substituent. The distribution of 2-aminoethyl substituents in the 3-O- and 6-O-positions of the D-glucopyranosyl units of cotton cellulose was estimated to be 0.20:1.00 from direct analysis of the hydrolyzate of O-(2-aminoethyl)cellulose, but the total substitution in the 2-O-position could not be estimated in this manner. The ratio of substituents in the 2-O-, 3-O-, and 6-O-positions was found to be 0.64:0.14:1.00 when the amino groups were converted to hydroxyl groups by diazotization, and the distribution was estimated in terms of the 2-hydroxyethyl substituents. It has been observed that a substantial fraction (57.5%) of the 2-O-(2-hydroxyethyl)-D-glucose from the chemically modified cellulose exists in the form of the inner glucosides. Several new monosubstituted glucoses have been prepared and characterized by g.l.c. for this purpose.