# US 5,344,946 A · Process for the preparation of vicinal diols and/or epoxides > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,344,946 A - Document ID: US5344946A - Status: Granted - Kind: A - Application number: 08/065,461 - Filed: 1993-05-20 - Granted: 1994-09-06 - Earliest claimed: 1991-04-09 - Assignees: Solvay Interox Limited - Inventors: Siegfried Warwel; Mark R. Klaas; Michael Sojka - Web page: https://patentgrep.com/patent/US5344946A ## CPC - C07C 29/03: by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 (by simultaneous introduction of -OH groups and halogens C07C29/64) - C07C 2601/14: The ring being saturated - C07C 2601/18: with a ring being at least seven-membered - C07C 2601/20: the ring being twelve-membered - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract The present invention provides a process for the preparation of vicinal diols and/or epoxides by the oxidation of olefinically-unsaturated compounds with the use of an inorganic heptavalent rhenium compound as catalyst and of hydrogen peroxide as oxidation agent, wherein the reaction is carried out in a solvent selected from the group consisting of organic phosphoric acid esters and ethers with a boiling point above 50.degree. C. under atmospheric conditions. ## Claims ### Claim 1 Process for the preparation of vicinal diols and/or epoxides by the oxidation of olefinically-unsaturated compounds with the use of an inorganic heptavalent rhenium compound as catalyst and of hydrogen peroxide as oxidation agent, wherein the reaction is carried out under atmospheric conditions and a pH of legs than 3 in a solvent selected from the group consisting of phosphoric acid esters and saturated ethers with a boiling point above 50.degree. C., wherein said group does not include epoxides. ### Claim 2 (depends on 1) Process according to claim 1, wherein the catalyst is used in a concentration of from 0.2 to 5 mol %, referred to an oxidisable carbon-carbon double bond of the olefinically-unsaturated compound. ### Claim 3 (depends on 2) Process according to claim 2, wherein the catalyst is used in a concentration of from 0.8 to 1.2 mol %, referred to an oxidisable carbon-carbon double bond of the olefinically-unsaturated compound. ### Claim 4 (depends on 1) Process according to claim 1, wherein the reaction is carried out at a pH value of from 0 to 2. ### Claim 5 (depends on 1) Process according to claim 1, wherein rhenium heptoxide is used as catalyst. ### Claim 6 (depends on 1) Process according to claim 1, wherein a perrhenate of the general formula M or M'.sub.2, in which M is an alkali metal or ammonium and M' is an alkaline earth metal, is used as catalyst. ### Claim 7 (depends on 6) Process according to claim 6, wherein the pH value of the reaction mixture is adjusted to a value of less than 3 by the addition of an inorganic or organic acid which is not oxidisable under the reaction conditions. ### Claim 8 (depends on 7) Process according to claim 7, wherein perchloric acid, phosphoric acid or sulphuric acid is used as inorganic acid and an alkyl or aryl sulphonic acid is used as organic acid. ### Claim 9 (depends on 1) Process according to claim 1, wherein rhenium or a rhenium compound with lower oxidation stage is added to the reaction mixture, the rhenium or rhenium compound thereby being oxidised by hydrogen peroxide to a catalytically-active heptavalent rhenium compound. ### Claim 10 (depends on 9) Process according to claim 9, wherein metallic rhenium or dirhenium decacarbonyl is added. ### Claim 11 (depends on 1) Process according to claim 1, wherein, as solvent, there is used a phosphoric acid trialkyl ester in which each alkyl radical can contain up to 10 carbon atoms. ### Claim 12 (depends on 11) Process according to claim 11, wherein, as solvent, there is used a phosphoric acid trialkyl ester in which each alkyl radical contains 2 to 8 carbon atoms. ### Claim 13 (depends on 12) Process according to claim 12, wherein, as solvent, there is used triethyl phosphate or tri-n-butyl phosphate. ### Claim 14 (depends on 1) Process according to claim 1, wherein, as solvent, there is used a cyclic or acyclic ether with several ether groups. ### Claim 15 (depends on 14) Process according to claim 14, wherein, as solvent, there is used a cyclic or acyclic ether with 2 to 4 ether groups. ### Claim 16 (depends on 15) Process according to claim 15, wherein 1,4-dioxane is used as solvent. ### Claim 17 (depends on 14) Process according to claim 14, wherein glyme or diglyme is used as solvent. ### Claim 18 (depends on 1) Process according to claim 1, wherein the reaction products are separated off from the reaction mixture and the residue is again used as catalyst solution in the reaction. ### Claim 19 (depends on 18) Process according to claim 18, wherein the separation of the reaction products takes place by filtration. ### Claim 20 (depends on 1) Process according to claim 1, wherein, as olefinically-unsaturated compound, there is used a cyclic or acyclic monoolefine, a diolefin or a polyene which can be optionally substituted by one or more functional groups selected from hydroxyl, carboxylic acid, carboxylic acid ester and aryl groups. ### Claim 21 (depends on 1) A process according to claim 1, wherein the hydrogen peroxide is used in a molar ratio of 1:1 to 4:1 to an oxidisable carbon-carbon double bond of the olefinically-unsaturated compound. ### Claim 22 (depends on 21) Process according to claim 21, wherein the hydrogen peroxide is used in a molar ratio of about 1.2:1 to an oxidisable carbon-carbon double bond of the olefinically-unsaturated compound. ### Claim 23 (depends on 1) Process according to claim 1, wherein the reaction is carried out at a temperature of from ambient temperature to 100.degree. C. ### Claim 24 (depends on 23) Process according to claim 23, wherein the reaction is carried out at a temperature of from 70.degree. to 90.degree. C.