The Reaction of Cotton with β-Propiolactone in the Presence of Alkali

Abstract

The reaction of cotton cellulose with β-propiolactone may be effected in the presence of strong alkalies such as sodium hydroxide and potassium hydroxide. Monoethanol amine and trimethylbenzyl ammonium hydroxide will also catalyze the reaction, but to a lesser degree. Di- and triethanolamine are ineffective. Byproducts of the reaction are water soluble and may be removed with a hot-water wash. Conditions of the reaction such as time, temperature, concentration of reagents, and effect of diluents were investigated and are reported. The products are mixed ethers and esters of cellulose and polyesters thereof, in fibrous form. The ether linkages are stable to saponification, while the ester linkages are broken. Therefore, saponification removes all but the carboxyethyl groups attached directly to the cellulose molecule.