Epoxide and fluorinated epoxide stabilizers for fluoroolefins

A composition consisting of at least one fluoroolefin, an effective amount of a stabilizer comprising:

• a. at least one compound selected from the group consisting of epoxides and fluorinated epoxides represented by Formula A, wherein each of R2 through R5 is H, alkyl of 1 to 6 carbon atoms, or fluoroalkyl of 1 to 6 carbon atoms with the proviso that at least one of R2 through R5 is a fluoroalkyl group;
• and
• b. at least one compound selected from the group consisting of thiophosphates, thiols, thioethers, and aryl sulfides;
• wherein:
• the thiophosphates are selected from the group consisting of monothiophosphates, dithiophosphates, trithiophosphates, dialkylthiophosphate esters, and mixtures thereof;
• the thiols are selected from the group consisting of methanethiol, ethanethiol, Coenzyme A, dimercaptosuccinic acid, (R)-2-(4-methylcyclohex-3-enyl)propane-2-thiol, cysteine, lipoamide and mixtures thereof;
• the thioethers are selected from the group consisting of benzyl phenyl sulfide, diphenyl sulfide, dioctadecyl 3,3′-thiodipropionate, didodecyl 3,3′-thiopropionate and mixtures thereof;
• and
• the aryl sulfides are selected from the group consisting of benzyl phenyl sulfide, diphenyl sulfide, and dibenzyl sulfide;
• and
• a lubricant selected from the groups consisting of mineral oils, alkylbenzenes, polyalphaolefins, silicone oils, polyoxyalkylene glycol ethers, polyol esters, polyvinylethers and mixtures thereof.

A composition consisting of at least one fluoroolefin, an effective amount of a stabilizer comprising:

• a. at least one compound selected from the group consisting of epoxides and fluorinated epoxides represented by Formula A, wherein each of R2 through R5 is H, alkyl of 1 to 6 carbon atoms, or fluoroalkyl of 1 to 6 carbon atoms with the proviso that at least one of R2 through R5 is a fluoroalkyl group;
• and
• b. at least one compound selected from the group consisting of thiophosphates, thiols, thioethers, and aryl sulfides;
• wherein:
• the thiophosphates are selected from the group consisting of monothiophosphates, dithiophosphates, trithiophosphates, dialkylthiophosphate esters, and mixtures thereof;
• the thiols are selected from the group consisting of methanethiol, ethanethiol, Coenzyme A, dimercaptosuccinic acid, (R)-2-(4-methylcyclohex-3-enyl)propane-2-thiol, cysteine, lipoamide and mixtures thereof;
• the thioethers are selected from the group consisting of benzyl phenyl sulfide, diphenyl sulfide, dioctadecyl 3,3′-thiodipropionate, didodecyl 3,3′-thiopropionate and mixtures thereof;
• and
• the aryl sulfides are selected from the group consisting of benzyl phenyl sulfide, diphenyl sulfide, and dibenzyl sulfide;
• and
• at least one additional stabilizer compound selected from the group consisting of phenols, phosphites, terpenes, terpenoids, and mixtures thereof.

A composition consisting of at least one fluoroolefin, an effective amount of a stabilizer comprising:

• a. at least one compound selected from the group consisting of epoxides and fluorinated epoxides represented by Formula A, wherein each of R2 through R5 is H, alkyl of 1 to 6 carbon atoms, or fluoroalkyl of 1 to 6 carbon atoms with the proviso that at least one of R2 through R5 is a fluoroalkyl group;
• and
• and
• b. at least one compound selected from the group consisting of thiophosphates, thiols, thioethers, and aryl sulfides;
• wherein:
• the thiophosphates are selected from the group consisting of monothiophosphates, dithiophosphates, trithiophosphates, dialkylthiophosphate esters, and mixtures thereof;
• the thiols are selected from the group consisting of methanethiol, ethanethiol, Coenzyme A, dimercaptosuccinic acid, (R)-2-(4-methylcyclohex-3-enyl)propane-2-thiol, cysteine, lipoamide and mixtures thereof;
• the thioethers are selected from the group consisting of benzyl phenyl sulfide, diphenyl sulfide, dioctadecyl 3,3′-thiodipropionate, didodecyl 3,3′-thiopropionate and mixtures thereof;
• and
• the aryl sulfides are selected from the group consisting of benzyl phenyl sulfide, diphenyl sulfide, and dibenzyl sulfide;
• and
• at least one metal deactivator selected from the group consisting of areoxalyl bis(benzylidene)hydrazide;
• N,N′-bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamoylhydrazine);
• 2,2′-oxamidobis-ethyl-(3,5-d-tert-butyl-4-hydroxyhydorcinnamate);
• N,N′-(disalicyclidene)-1,2-propanediamine;
• ethyenediaminetetraacetic acid and salts thereof;
• triazoles;
• benzotriazole, 2-mercaptobenzothiazole, tolutriazole derivatives, N,N-disalicylidene-1,2-diaminopropane, and mixtures thereof.

A composition consisting of:

• a. at least one fluoroolefin selected from the group consisting of HFC-1225ye, HFC-1234yf, HFC-1234ze, and HFC-1243zf;
• b. an effective amount of a stabilizer comprising:
• i. at least one compound selected from the group consisting of epoxides and fluorinated epoxides represented by Formula A, wherein each of R2 through R5 is H, alkyl of 1 to 6 carbon atoms, or fluoroalkyl of 1 to 6 carbon atoms with the proviso that at least one of R2 through R5 is a fluoroalkyl group;
• and
• ii. at least one compound selected from the group consisting of thiophosphates, thiols, thioethers, and aryl sulfides;
• wherein:
• the thiophosphates are selected from the group consisting of monothiophosphates, dithiophosphates, trithiophosphates, dialkylthiophosphate esters, and mixtures thereof;
• the thiols are selected from the group consisting of methanethiol, ethanethiol, Coenzyme A, dimercaptosuccinic acid, (R)-2-(4-methylcyclohex-3-enyl)propane-2-thiol, cysteine, lipoamide and mixtures thereof;
• the thioethers are selected from the group consisting of benzyl phenyl sulfide, diphenyl sulfide, dioctadecyl 3,3′-thiodipropionate, didodecyl 3,3′-thiopropionate and mixtures thereof;
• and
• the aryl sulfides are selected from the group consisting of benzyl phenyl sulfide, diphenyl sulfide, and dibenzyl sulfide;
• and, optionally:
• c. at least one additional compound selected from a hydrofluorocarbon or hydrocarbon.