# US 5,705,708 A · Inhibition of discoloration of cumene hydroperoxide > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,705,708 A - Document ID: US5705708A - Status: Granted - Kind: A - Application number: 08/717,624 - Filed: 1996-09-23 - Granted: 1998-01-06 - Earliest claimed: 1996-09-23 - Assignees: Witco Corporation - Inventors: Peter Frenkel - Web page: https://patentgrep.com/patent/US5705708A ## CPC - C07C 407/006: {Stabilisation; Use of additives} - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract Discoloration of cumene hydroperoxide is reduced or inhibited by adding to the cumene hydroperoxide an effective amount on the order of 30 to 1000 ppm of a stabilizer of the formula R'C(O)OM wherein R' is alkyl, alkenyl, cycloalkyl or aryl containing 1-40 carbon atoms, or the formula R.sub.4 NOH wherein each R is independently alkyl or cycloalkyl containing 1-40 carbon atoms. ## Claims ### Claim 1 A composition comprising cumene hydroperoxide and a color stabilizer selected from the group consisting of (a) alkali metal salts of organic acids, having the formula (I) R'C(O)OM (I) and mixtures thereof, wherein R' is an alkyl, alkenyl, cycloalkyl or aryl group containing 1 to 40 carbon atoms, and M is sodium, potassium, rubidium or cesium; and (b) quaternary ammonium hydroxides having the formula (II) R.sub.4 NOH (II) and mixtures thereof, wherein each R is independently an alkyl or cycloalkyl group containing 1 to 40 carbon atoms; wherein said stabilizer is present in an amount effective to inhibit discoloration of said cumene hydroperoxide. ### Claim 2 (depends on 1) A composition according to claim 1 wherein R' contains 1 to 20 carbon atoms. ### Claim 3 (depends on 1) A composition according to claim 1 wherein each R contains 1 to 4 carbon atoms. ### Claim 4 (depends on 1) A composition according to claim 1 wherein the stabilizer is selected from the group consisting of sodium acetate, potassium acetate, rubidium acetate, cesium acetate, sodium methacrylate, sodium butyrate, potassium benzoate, potassium stearate, sodium stearate, and sodium propionate. ### Claim 5 (depends on 1) A composition according to claim 1 wherein the stabilizer is potassium acetate. ### Claim 6 (depends on 1) A composition according to claim 1 wherein the stabilizer is selected from the group consisting of tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, and tetrabutylammonium hydroxide. ### Claim 7 (depends on 6) A composition according to claim 6 wherein the stabilizer is tetraethylammonium hydroxide. ### Claim 8 (depends on 1) A composition according to claim 1 wherein the amount of said stabilizer present is at least 30 ppm by weight of the cumene hydroperoxide. ### Claim 9 (depends on 8) A composition according to claim 8 wherein the amount of said stabilizer present is up to 1000 ppm by weight of the cumene hydroperoxide. ### Claim 10 (depends on 8) A composition according to claim 8 wherein the amount of said stabilizer present is up to 100 ppm by weight of the cumene hydroperoxide. ### Claim 11 A method of treating discolored cumene hydroperoxide so as to reduce said discoloration, comprising adding to said cumene hydroperoxide a color stabilizer selected from the group consisting of (a) alkali metal salts of organic acids, having the formula (I) R'C(O)OM (I) and mixtures thereof, wherein R' is an alkyl, alkenyl, cycloalkyl or aryl group containing 1 to 40 carbon atoms, and M is sodium, potassium, rubidium or cesium; and (b) quaternary ammonium hydroxides having the formula (II) R.sub.4 NOH (II) and mixtures thereof, wherein each R is independently an alkyl or cycloalkyl group containing 1 to 40 carbon atoms; in an amount of said stabilizer effective to reduce discoloration of said cumene hydroperoxide. ### Claim 12 (depends on 11) A method according to claim 11 wherein R' contains 1 to 20 carbon atoms. ### Claim 13 (depends on 11) A method according to claim 11 wherein each R contains 1 to 4 carbon atoms. ### Claim 14 (depends on 11) A method according to claim 11 wherein the stabilizer is selected from the group consisting of sodium acetate, potassium acetate, rubidium acetate, cesium acetate, sodium methacrylate, sodium butyrate, potassium benzoate, potassium stearate, sodium stearate, and sodium propionate. ### Claim 15 (depends on 14) A method according to claim 14 wherein the stabilizer is potassium acetate. ### Claim 16 (depends on 11) A method according to claim 11 wherein the stabilizer is selected from the group consisting of tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, and tetrabutylammonium hydroxide. ### Claim 17 (depends on 16) A method according to claim 16 wherein the stabilizer is tetraethylammonium hydroxide. ### Claim 18 (depends on 11) A method according to claim 11 wherein the amount of said stabilizer added is at least 30 ppm by weight of the cumene hydroperoxide. ### Claim 19 (depends on 18) A method according to claim 18 wherein the amount of said stabilizer added is up to 1000 ppm by weight of said cumene hydroperoxide. ### Claim 20 (depends on 18) A method according to claim 18 wherein the amount of said stabilizer added is up to 500 ppm by weight of said cumene hydroperoxide. ### Claim 21 (depends on 11) A method according to claim 11 further comprising heating the composition formed by adding said stabilizer to said cumene hydroperoxide to a temperature of 50.degree. C. to 70.degree. C. for 0.5 to 2.0 hours. ### Claim 22 A method of treating cumene hydroperoxide so as to inhibit its discoloration, comprising adding to said cumene hydroperoxide a color stabilizer selected from the group consisting of (a) alkali metal salts of organic acids, having the formula (I) R'C(O)OM (I) and mixtures thereof, wherein R' is an alkyl, alkenyl, cycloalkyl or aryl group containing 1 to 40 carbon atoms, and M is sodium, potassium, rubidium or cesium; and (b) quaternary ammonium hydroxides having the formula (II) R.sub.4 NOH (II) and mixtures thereof, wherein each R is independently an alkyl or cycloalkyl group containing 1 to 40 carbon atoms; in an amount of said stabilizer effective to inhibit discoloration of said cumene hydroperoxide. ### Claim 23 (depends on 22) A method according to claim 22 wherein R' contains 1 to 20 carbon atoms. ### Claim 24 (depends on 22) A method according to claim 22 wherein each R contains 1 to 4 carbon atoms. ### Claim 25 (depends on 22) A method according to claim 22 wherein the stabilizer is selected from the group consisting of sodium acetate, potassium acetate, rubidium acetate, cesium acetate, sodium methacrylate, sodium butyrate, potassium benzoate, potassium stearate, sodium stearate, and sodium propionate. ### Claim 26 (depends on 25) A method according to claim 25 wherein the stabilizer is potassium acetate. ### Claim 27 (depends on 22) A method according to claim 22 wherein the stabilizer is selected from the group consisting of tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, and tetrabutylammonium hydroxide. ### Claim 28 (depends on 27) A method according to claim 27 wherein the stabilizer is tetraethylammonium hydroxide. ### Claim 29 (depends on 22) A method according to claim 22 wherein the amount of said stabilizer added is at least 30 ppm by weight of the cumene hydroperoxide. ### Claim 30 (depends on 29) A method according to claim 29 wherein the amount of said stabilizer added is up to 1000 ppm by weight of said cumene hydroperoxide. ### Claim 31 (depends on 29) A method according to claim 29 wherein the amount of said stabilizer added is up to 500 ppm by weight of said cumene hydroperoxide. ### Claim 32 (depends on 22) A method according to claim 22 further comprising heating the composition formed by adding said stabilizer to said cumene hydroperoxide to a temperature of 50.degree. C. to 70.degree. C. for 0.5 to 2.0 hours.