# US 4,399,007 A · Hydrogenation > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,399,007 A - Document ID: US4399007A - Status: Granted - Kind: A - Application number: 06/274,578 - Filed: 1981-06-17 - Granted: 1983-08-16 - Earliest claimed: 1976-12-31 - Assignees: Lever Brothers Company - Inventors: Albert Froling; Rudolph O. de Jongh; Josephus M. A. Kemps - Web page: https://patentgrep.com/patent/US4399007A ## CPC - C25B 3/25: Reduction - C11C 3/12: by hydrogenation - C25B 3/07: Oxygen containing compounds - C25B: ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR (anodic or cathodic protection C23F13/00; single-crystal growth C30B) - C11C: FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM ## Abstract Process for the selective hydrogenation of polyunsaturated compounds with a metallic catalyst. The selectivity is increased and trans-isomerization is decreased by carrying out the hydrogenation in the presence of a catalyst to which, before the hydrogenation is started, an external potential, differing from the naturally occuring equilibrium potential, is applied while in contact with an electrolyte, such as a quaternary ammonium salt, dissolved in a liquid, such as an alcohol or a ketone. ## Claims ### Claim 1 Process for the selective hydrogenation of a poly-unsaturated organic compound containing more than one double bond in a carbon chain or ring comprising hydrogenating said compound with molecular hydrogen in the presence of a metallic hydrogenation catalyst and applying an external electric potential differing from the equilibrium potential and having a value of between 0 V and -3 V as measured against a saturated calomel electrode to the catalyst while it is in contact with a liquid, which liquid contains an electrolyte. ### Claim 2 (depends on 1) Process according to claim 1, in which the external electric potential is applied during the whole of the hydrogenation. ### Claim 3 (depends on 1) Process according to claim 1, in which the external electric potential is switched off after the hydrogenation reaction is started. ### Claim 4 (depends on 1) Process according to claim 1, in which the external potential is applied to the catalyst in a vessel separated from the hydrogenation reactor. ### Claim 5 (depends on 1) Process according to claim 1, in which the liquid containing an electrolyte and catalyst are brought into a reaction vessel under a hydrogen atmosphere, an external potential is applied to the catalyst and thereafter the compound to be hydrogenated is brought into the reaction vessel. ### Claim 6 (depends on 1) Process according to claim 1, in which the liquid containing an electrolyte, catalyst and the compound to be hydrogenated are brought into a reaction vessel under an inert atmosphere, an external potential is applied to the catalyst, and thereafter the inert atmosphere is replaced by hydrogen. ### Claim 7 (depends on 4) Process according to claim 4, in which liquid containing an electrolyte and the catalyst are brought into the separate vessel under an inert atmosphere, an external electric potential is applied to the catalyst, and the contents of said vessel are brought into the hydrogenation reactor already containing the compound to be hydrogenated. ### Claim 8 (depends on 1) Process according to claim 1 in which as the catalyst a metal supported on a carrier is used. ### Claim 9 (depends on 8) Process according to claim 8, in which as the metal palladium platinum, rhodium, ruthenium and/or nickel is used. ### Claim 10 (depends on 8) Process according to claim 8, in which the carrier consists of a metal, carbon black, silica or an ion-exchange resin. ### Claim 11 (depends on 1) Process according to claim 1, in which the external potential is applied to the catalyst by stirring a suspension of the catalyst to contact the catalyst particles with an electrode to which an electric potential is applied. ### Claim 12 (depends on 1) Process according to claim 1, in which an external potential of between 0 V to -3 V as measured against a saturated calomel electrode, is applied. ### Claim 13 (depends on 1) Process according to claim 1, in which as the liquid an alcohol or a ketone is used. ### Claim 14 (depends on 1) Process according to claim 1, in which as the liquid water, methanol, ethanol, propanol, glycerol, acetone, methyl cellosolve, acetonitrile, hexane, benzene or a mixture thereof is used. ### Claim 15 (depends on 1) Process according to claim 1, in which the ratio by weight of the liquid to the compound to be hydrogenated is between 1:1 to 20:1. ### Claim 16 (depends on 1) Process according to claim 1, in which as the electrolyte a quaternary ammonium salt is used. ### Claim 17 (depends on 1) Process according to claim 1, in which the electrolyte is used in a concentration of between 0.001 to 0.1 mol per liter. ### Claim 18 (depends on 1) Process according to claim 1, in which the hydrogenation is carried out at a temperature of between -20.degree. C. to 200.degree. C. ### Claim 19 (depends on 1) Process according to claim 1, in which the hydrogenation is carried out under a pressure of between 1 to 25 atm. ### Claim 20 (depends on 1) Process according to claim 1, in which an edible triglyceride oil is hydrogenated. ### Claim 21 (depends on 1) The process of claim 1 wherein the catalyst is selected from the group consisting of palladium, platinum, rhodium, ruthenium and nickel. ### Claim 22 (depends on 1) The process of claim 1 wherein the electrolyte is selected from the group consisting of quaternary ammonium salts, sodium dodecyl-6-sulfonate, sodium acetate, sodium hydroxide and sodium methanolate. ### Claim 23 (depends on 1) The process of claim 1 wherein the electrolyte is selected from the group consisting tetraethylammonium perchlorate, tetrabutylammonium perchlorate, tetraethylammonium phosphate, tetraethylammonium bromide, tetraethylammonium paratoluenesulfonate, and tetramethylammonium acetate.