Produits Chimiques Ugine Kuhlmann

P C U K Produits Chimiques Ugine Kuhlmann

Michele Pralus

Jean-Pierre Schirmann

Jean-Claude Lecoq

Serge-Yvon Delavarenne

Process for manufacturing .SIGMA.- caprolactone by oxidation of cyclohexanone by means of a crude C.sub.2 -C.sub.4 percarboxylic acid solution, resulting from the reaction of hydrogen peroxide on the corresponding carboxylic acid in the presence of a weak acid catalyst, with continuous elimination of water by azeotropic entrainment, characterized in that the molar ratio of cyclohexanone used to the percarboxylic acid is between about 0.50 to 0.99.

Process for the preparation of epsilon-caprolactone

This invention relates to a process for the preparation of stable solutions of .epsilon.-caprolactone by means of the oxidation of cyclohexanone by a percarboxylic acid containing 2 to 4 carbon atoms. According to the invention, the percarboxylic acid is in the form of a crude solution, such as that resulting from the reaction of hydrogen peroxide with the corresponding carboxylic acid in the presence of a boric acid catalyst with the continuous elimination of water by azeotropic entrainment.

Process for the preparation of .epsilon.-caprolactone

Process of preparing substantially anhydrous solutions of percarboxylic acids which comprises reacting hydrogen peroxide contained in an aqueous solution with a water miscible carboxylic acid in the presence of a catalyst and an azeotropic organic solvent, continuously removing the water added with the hydrogen peroxide and formed during the reaction by azeotropic distillation by way of a distillation column, and continuously injecting water into the top of the distillation column during at least the major portion of the reaction time, the quantity of the injected water being less than the quantity of the water removed by azeotrope distillation.

Process for the preparation of percarboxylic acids

The present invention relates to a new process for the catalytic epoxidation of olefins which comprises reacting an olefin of the formula ##STR1## in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which can be the same or different, represent either a hydrogen atom, a straight alkyl radical having 1 to 30 carbon atoms, a branched alkyl radical or cycloalkyl radical having 3 to 12 carbon atoms, a hydrocarbon radical having 6 to 12 carbon atoms and containing a phenyl group; or R.sub.1 and R.sub.2, or R.sub.3 or R.sub.4 together represent a straight or branched alkylene radical with 3 to 11 carbon atoms, (the radicals R.sub.1, R.sub.2, R.sub.3 and R.sub.4 can be unsaturated and/or substituted with functional groups which are stable in the reaction medium, such as hydroxy, chloro, fluoro, bromo, iodo, nitro (--NO.sub.2), nitroso (--NO), alkoxy, (--OR') amino (--NH.sub.2), carbonyl (=CO), alkylcarbonyl ##STR2## carboxylic acid (--COOH), carboxylic acid ester (--COOR'), amide or carbamyl (--CONH.sub.2), nitrile or cyano (--CN) groups, etc.), with hydrogen peroxide at a pH of between about 6 and 9 in the presence of a catalytic system containing at least one derivative of mercury and at least one derivative of the elements IVA, VA, VIA of the Mendeleev Periodic Table. The two fundamental constituents of the catalyst may either belong to distinct molecules or may form part of the same molecule, for example within a complex.

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Saint Cyr au Mont d'or, France

Michele Pralus