The preparation of O-(formylmethyl)cellulose

Abstract

A new aldehyde derivative of cellulose, O-(formylmethyl)cellulose was prepared by three methods. The first one is based on the base-catalysed elimination of nitromethane from O-(3-nitro-2-hydroxypropyl)cellulose obtained by the reaction of sodium nitrite in dimethylformamide with O-(3-iodo-2-hydroxypropyl)cellulose. The second process is a mild acid hydrolysis of O-(2,2-diethoxylethyl)cellulose formed through the alkylation of dry alkali cellulose by bromoacetaldehyde diethyl acetal. The principle of the third procedure is a periodate oxidation of O-(2,3-dihydroxypropyl)cellulose, prepared from an O-(3-chloro-2-hydroxypropyl) derivative in an aqueous alkali solution. The procedure yields a mixed aldehydic derivative - O-(formylmethyl)-2,3-dialdehydocellulose. The application of these reactions to bead cellulose preserves its porosity as well as the spheric particle-shape even at the degree of substitution by formylmethyl groups up to 0.2.