Gas phase pyrolysis of alkyl acetates

Abstract

Abstract An investigation was made into the thermal decomposition of twenty‐seven aliphatic acetates, using a micro‐scale flow reactor connected to a gas chromatograph. The rate of elimination increases markedly as the degree of alkylation of the α‐carbon atom becomes higher. The accelerating effect of β‐alkyl substituents on the rate of elimination is small, as compared with that of α‐alkyl substituents. The reactivity of the aliphatic acetates approaches a limiting value as the carbon chain is extended. The reactivity decreases on the introduction at the β‐carbon atom of an electron‐attracting group and increases on the introduction of an electron‐releasing group. A tentative mechanism is proposed which is based on the reversible formation of an ion‐pair.