Transvinylation as a First Stage of Coupling Production of Vinyl Esters and Acetic Acid or Propionic Acid Reaction Products

摘要

Process for coproduction of a vinyl ester of the formula R—C(O)O—CH═CH by transvinylation reaction of a carboxylic acid of the formula R—C(O)OH with a transvinylating reagent of the formula R1—C(O)O CH═CH2, characterized in that (a) the transvinylation reaction is conducted continuously at a temperature of 90 to 160° C. and at a pressure of 0.5 to 15 MPa without withdrawal of a reactant in the presence of a transition meta/catalyst containing at least one transition metal selected from the group of ruthenium, osmium, rhodium, iridium, palladium and platinum; (b) the resulting reaction mixture is separated into its constituents and the vinyl ester of the formula R—C(O)O—CH═CH2 and the carboxylic acid of the formula R1—C(O)—OH are removed; and (c) the carboxylic acid obtained after step (b) is converted to a derivative of the formula R1—C(O)—X, R1—CH2—OH or R6—C(O)—OH in which X is vinyloxy, O—CH—CH2, halogen, alkoxy of the formula OR2 in which R2 is a substituted or unsubstituted hydrocarbyl radical having 1 to 10 carbon atoms, amino of the formula NR3R4 in which R3 and R4 are each independently hydrogen or a substituted or unsubstituted hydrocarbyl radical having 1 to 10 carbon atoms, or carboxyl of the formula O—C(O)—R5 in which R5 is hydrogen or a substituted or unsubstituted hydrocarbyl radical having 1 to 10 carbon atoms, and R6 is the partly or fully halogen-substituted R1 radical.

主权项

1. Process for coproduction of a vinyl ester of the formula R—C(O)O—CH═CH2 by transvinylation reaction of a carboxylic acid of the formula R—C(O)OH with a transvinylating reagent of the formula R1—C(O)O—CH═CH2:
R—C(O)OH+R1—C(O)O—CH═CH2—R1—C(O)OH+R—C(O)O—CH═CH2 where R is an aliphatic, cycloaliphatic or aromatic radical and R1 is methyl or ethyl, and of a derivative of the formula R1—C(O)—X which is derived from the carboxylic acid R1—C(O)—OH formed and in which X is vinyloxy, O—CH═CH2, halogen, alkoxy of the formula OR2 in which R2 is a substituted or unsubstituted hydrocarbyl radical having 1 to 10 carbon atoms, amino of the formula NR3R4 in which R3 and R4 are each independently hydrogen or a substituted or unsubstituted hydrocarbyl radical having 1 to 10 carbon atoms, or carboxyl of the formula O—C(O)—R5 in which R5 is hydrogen or a substituted or unsubstituted hydrocarbyl radical having 1 to 10 carbon atoms, or of a derivative of the formula R1—CH2—OH or of a derivative of the formula R6—C(O)—OH in which R6 is the partly or fully halogen-substituted R1 radical, characterized in that
(a) the transvinylation reaction is conducted continuously without withdrawal of a reactant in the presence of a transition metal catalyst containing at least one transition metal selected from the group of ruthenium, osmium, rhodium, iridium, palladium and platinum; (b) the resulting reaction mixture is separated into its constituents and the vinyl ester of the formula R—C(O)O—CH═CH2 and the carboxylic acid of the formula R1—C(O)—OH are removed; and (c) the carboxylic acid obtained after step (b) is converted to a derivative of the formula R1—C(O)—X, R1—CH2—OH or R6—C(O)—OH.