THE LOCATION AND DISTRIBUTION OF SUBSTITUENTS IN A PURIFIED HYDROXYETHYL CELLULOSE

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Abstract
A purified hydroxyethylcellulose of molar substitution 1.33 was completely hydrolyzed in acid, and paper chromatography of the neutral hydrolyzate separated glucose, the three possible hydroxyethyl glucoses, the three di(hydroxyethyl) derivatives, and 2,3,6-tri-O-hydroxyethyl glucose. These substances were isolated as sirups possibly contaminated with the corresponding hydroxyethoxyethyl and higher homologues, which had nearly the same Rf values in the system used. The chromatographic behavior of each of the seven hydroxyethyl glucoses was established by synthetical methods from methyl 4,6-O-benzylidene glucoside, 1,2;5,6-di-O-isopropylidene, and 1,2;3,5-di-O-methylene glucofuranose. Methyl 2,3-di-O-hydroxyethyl-4,6-O-benzylidene-β-glucopyranoside, m.p. 98°–100° and 119–121°, and 1,2-mono-O-methylene glucofuranose, m.p. 147°, were new substances.A quantitative examination of the hydrolyzates showed that the condensation between alkali cellulose and ethylene oxide was nearly homogeneous, that the primary hydroxyl groups in the anhydroglucose units reacted fastest, and those in the third positions slowest. The average substituent had a polyoxyethylene chain length of 1.6 units. Three commercial hydroxyethylcelluloses of apparent M.S. about 1.4 contained non-carbohydrate polyethylene glycols.

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