Oxidation process including recovery and recycle of catalyst

Claim 1

A process for the production of diacycloxy olefins which comprises: (a) oxidizing at least one acyclic conjugated diolefin with molecular oxygen under oxidation reaction conditions in carboxylic acid reactant media employing a catalyst system comprising (A) at least one copper or antimony compound, (B) at least one alkali metal compound, (C) a halide ion-source wherein said halide is bromide or chloride, thereby preparing a product reaction mixture comprising at least one diacycloxy olefin, catalyst residues, unreacted diolefin, residual oxygen, and residual carboxylic acid media, wherein said acyclic conjugated diolefin is selected from unsubstituted and substituted diolefins of 4 to 16 carbon atoms wherein the substituents are selected from the group consisting of halogen, cyano, --COOR', and hydrocarbyl radicals, wherein R' is hydrogen or an alkyl or aryl radical; and said carboxylic acid media is selected from the group consisting of mono- and dicarboxylic aliphatic, cycloaliphatic, and aromatic acids, corresponding anhydrides, and mixtures, having 2 to 18 carbon atoms per molecule; wherein said (A) where copper is selected from the group consisting of copper chlorides, bromides, oxides, carbonates, carboxylates, nitrates, orthophosphates, sulfates, and mixtures; and where antimony is selected from the group consisting of the chlorides, bromides, oxides, carboxylates, nitrates, sulfates, and mixtures; said (B) is selected from the group consisting of the halides, nitrates, carboxylates, oxides, hydroxides, carbonates, orthophosphates, and sulfates, of lithium, sodium, potassium, rubidium, and cesium, and mixtures; and said (C) halide-source is a said (A) or (B) where said (A) or (B) is the halide, alkaline earth metal halides, or diolefin; (b) venting said product reaction mixture of any light unreacted components including residual oxygen, leaving a stripped reaction mixture, (c) fractionating said stripped reaction mixture, thereby distilling off streams comprising said residual carboxylic acid media, and unreacted diolefin not vented, leaving a remaining reaction mixture comprising diacyloxy olefin product and catalyst residues, (d) extracting said remaining reaction mixture with an effective amount of a solvent in which said diacyloxy olefin product exhibits a high degree of solubility, and said catalyst residues exhibit a low solubility, thereby forming an extract containing said diacyloxy olefin product, and a extraction residue containing said catalyst residues, wherein said solvent is normally liquid and consists of aliphatic halohydrocarbons or unsubstituted or alkyl-substituted aromatic solvents, or mixtures thereof, (e) recycling said separated carboxylic acid media from said step (c) to said step (a), (f) recycling extraction residue containing said catalyst residues to said step (a), (g) separating said diacyloxy olefin product from said extract, leaving a recovered solvent, and (h) recycling said recovered solvent to said step (d).