Patent ID: 9174955
Filing Date: 2015-11-03
Classification: C07D

Abstract:
1. A process for the epoxidation of a vinyl carboxylate or an allyl carboxylate, comprising: reacting a vinyl carboxylate or an allyl carboxylate using an oxidant and a water-soluble manganese complex in an aqueous reaction medium, wherein the aqueous reaction medium comprises a 100% water phase excluding any of the vinyl carboxylate or the allyl carboxylate and/or the corresponding oxides dissolved therein, wherein the molar ratio of a vinyl carboxylate or an allyl carboxylate to oxidant is from greater than 1:1 to 12:1 and wherein the water-soluble manganese complex comprises: a mononuclear species of the general formula (I): or a binuclear species of the general formula (II): wherein Mn is a manganese; each L is independently a polydentate ligand of triazacyclononane or a substituted triazacyclononane, each X is independently a coordinating species selected from the group consisting of: RO − , Cl − , Br − , I − , F − , NCS − , N 3 − , I 3 − , NH 3 , NR 3 , RCOO − , RSO 3 − , RSO 4 − , OH − , O 2− , O 2 2− , HOO − , H 2 O, SH − , CN − , OCN − , and S 4 2− and combinations thereof, and R is a C 1 -C 20 radical selected from the group consisting of alkyl, cycloalkyl, aryl, benzyl and combinations thereof, and each μ-X is independently a bridging coordinating species selected from the group consisting of: RO − , Cl − , Br − , I − , F − , NCS − , N 3 − , I 3 − , NH 3 , NR 3 , RCOO − , RSO 3 − , RSO 4 − , OH − , O 2− , O 2 2− , HOO − , H 2 O, SH − , CN − , OCN − , and S 4 2− and combinations thereof, and R is a C 1 -C 10 radical selected from the group consisting of alkyl, cycloalkyl, aryl, benzyl and combinations thereof, wherein Y is a non-coordinating counter ion selected from the group consisting of RO wherein the vinyl carboxylate or the allyl carboxylate is represented by an ester of the following formulae: wherein R 1 is a mono or polyvalent radical of 6 or more carbon atoms and R 1 ′ is a mono or polyvalent radical of 5 or more carbon atoms, wherein n corresponds to the number of ester groups and comprises an integer of 1 or greater, and wherein the total number of carbon atoms in the ester comprises 9 or more carbon atoms, wherein R 1 optionally contains 1 or more heteroatoms, and wherein R 1 ′ optionally contains 1 or more heteroatoms.