Nonconjugated linseed vinyl ether by vinyl transetherification. Preparation procedure

Abstract

AbstractAn improved procedure is described for preparing nonconjugated linseed vinyl ether monomer by transetherification of linseed alcohol with ethyl vinyl ether. By use of a mercuric acetate‐oxalic acid catalyst mixture, an excess of ethyl vinyl ether, a reaction temperature of 45°C., and an evaporation, water‐extraction procedure for continuous removal of by‐product ethanol as the reaction proceeds, 91% of the linseed alcohol was converted to the fatty vinyl ether in 6 1/2 hrs. When mercuric acetate was used alone, more catalyst was required; at 90°C, and above, the over‐all rate and yield were reduced by partial deactivation of the catalyst. This reduction was attributed to a side reaction wherein the mercuric salt was added to the fatty acid radical at points of unsaturation. All the various methods that were compared for purifying the linseed monomer produced a product of polymerization quality. While vacuum distillation, followed by an alumina adsorption treatment, gave a monomer of the highest purity, a monomer, vacuum‐distilled only, should be of suitable polymerization quality for many purposes.