Manufacture of an epoxyethyl carboxylate or glycidyl carboxylate

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):
• [LMnX3]Y (I),
• or a binuclear species of the general formula (II):
• [LMn(μ-X)3MnL]Yn (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−, N3−, I3−, NH3, NR3, RCOO−, RSO3−, RSO4−, OH−, O2−, O22−, HOO−, H2O, SH−, CN−, OCN−, and S42− and combinations thereof, and R is a C1-C20 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−, N3−, I3−, NH3, NR3, RCOO−, RSO3−, RSO4−, OH−, O2−, O22−, HOO−, H2O, SH−, CN−, OCN−, and S42− and combinations thereof, and R is a C1-C10 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−, Cl−, Br−, I−, F−, SO42−, RCOO−, PF6−, acetate, tosylate, triflate, and a combination thereof, and R is a C1-C20 radical selected from the group consisting of alkyl, cycloalkyl, aryl, benzyl and combinations thereof, n is 1 or 2, and wherein the aqueous reaction medium further comprises a buffer system to stabilize the pH and the epoxidation is carried out at a pH in the range of from 2 to 5, and
• wherein the vinyl carboxylate or the allyl carboxylate is represented by an ester of the following formulae:
• R1(C(O)OCH═CH2)n;
• or
• R1′(C(O)OCH2CH═CH2)n,
• wherein R1 is a mono or polyvalent radical of 6 or more carbon atoms and R1′ 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 R1 optionally contains 1 or more heteroatoms, and wherein R1′ optionally contains 1 or more heteroatoms.