Phenol stabilizers for fluoroolefins

1. A composition comprising:

a. at least one fluoroolefin;

b. and an effective amount of stabilizer comprising at least one phenol and at least one compound selected from the group consisting of functionalized perfluoropolyethers.

2. The composition of claim 1 further comprising at least one additional compound selected from the group consisting of fluoroolefins, hydrofluorocarbons, hydrocarbons, dimethyl ether, CF 3 I, carbon dioxide, ammonia, and mixtures thereof.

3. The composition of claim 1 further comprising a lubricant selected from the groups consisting of mineral oils, alkylbenzenes, poly-alpha-olefins, silicone oils, polyoxyalkylene glycol ethers, polyol esters, and polyvinylethers and mixtures thereof.

4. The composition of claim 1 further comprising at least one additional stabilizer compound selected from the group consisting of phosphites, terpenes, terpenoids, epoxides, fluorinated epoxides, and mixtures thereof.

5. The composition of claim 4 wherein:

a. the phosphites are selected from the group consisting of tris-(di-tert-butylphenyl) phosphite, di-n-octyl phosphite, iso-decyl diphenyl phosphite, and mixtures thereof;

b. the terpenes and/or terpenoids are selected from the group consisting of isoprene, myrcene, allo-cimene, beta-ocimene, terebene, d-limonene, retinal, pinene, menthol, geraniol, farnesol, phytol, Vitamin A, terpinene, delta-3-carene, terpinolene, phellandrene, fenchene, dipentene, lycopene, betacarotene, zeaxanthin, hepaxanthin, and isotretinoin, abietane, ambrosane, aristolane, atisane, beyerane, bisabolane, bornane, caryophyllane, cedrane, dammarane, drimane, eremophilane, eudesmane, fenchane, gammacerane, germacrane, gibbane, grayanotoxane, guaiane, himachalane, hopane, humulane, kaurane, labdane, lanostane, lupane, p-menthane, oleanane, ophiobolane, picrasane, pimarane, pinane, podocarpane, protostane, rosane, taxane, thujane, trichothecane, ursane, and mixtures thereof;

c. the epoxide stabilizers are selected from the group consisting of 1,2-propylene oxide, 1,2-butylene oxide, butylphenylglycidy ether, pentylphenylglycidyl ether, hexylphenylglycidyl ether, heptylphenylglycidyl ether, octylphenylglycidyl ether, nonylphenylglycidyl ether, decylphenylglycidyl ether, glycidyl methylphenyl ether, 1,4-glycidyl phenyl diether, 4-methoxyphenylglycidyl ether, naphthyl glycidyl ether, 1,4-diglycidyl naphthyl diether, butylphenyl glycidyl ether, n-butyl glycidyl ether, isobutyl glycidyl ether, hexanediol diglycidyl ether, allyl glycidyl ether, polypropylene glycol diglycidyl ether.and mixtures thereof; and

d. the fluorinated epoxides are represented by formula D

 wherein each of R 2 through R 5 is H, alkyl of 1-6 carbon atoms or fluoroalkyl of 1-6 carbon atoms with the proviso that at least one of R 2 through R 5 is a fluoroalkyl group.

6. The composition of claim 1 wherein the phenol comprises at least one phenol selected from the group consisting of 2,6-di-tert-butyl-4-methylphenol; 2,6-di-tert-butyl-4-ethylphenol; 2,4-dimethyl-6-tertbutylphenol; tocopherol; hydroquinone; t-butyl hydroquinone; 4,4′-thio-bis(2-methyl-6-tert-butylphenol); 4,4′-thiobis(3-methyl-6-tertbutylphenol); 2,2′-thiobis(4-methyl-6-tert-butylphenol); 4,4′-methylenebis(2,6-di-tert-butylphenol); 4,4′-bis(2,6-di-tert-butylphenol); 2,2′-methylenebis(4-ethyl-6-tertbutylphenol); 2,2′-methylenebis(4-methyl-6-tert-butylphenol); 4,4-butylidenebis(3-methyl-6-tert-butylphenol); 4,4-isopropylidenebis(2,6-di-tert-butylphenol); 2,2′-methyleenbis(4-methyl-6-nonylphenol); 2,2′-isobutylidenebis(4,6-dimethylphenol; 2,2′-methylenebis(4-methyl-6-cyclohexylphenol, 2,2′-methylenebis(4-ethyl-6-tert-butylphenol); butylated hydroxyl toluene (BHT); 2,6-di-tert-alpha-dimethylamino-p-cresol; 4,4-thiobis(6-tert-butyl-m-cresol; acylaminophenols; 2,6-di-tert-butyl-4(N,N′-dimethylaminomethylphenol); bis(3-methyl-4-hydroxy-5-tert-butylbenzyl)sulfide; bis(3,5-di-tert-butyl-4-hydroxybenzyl)sulfide and mixtures thereof.

7. The composition of claim 1 wherein said fluoroolefin is at least one compound selected from the group consisting of:

(i) fluoroolefins of the formula E- or Z—R 1 CH═CHR 2 , wherein R 1 and R 2 are, independently, C 1 to C 6 perfluoroalkyl groups;

(ii) cyclic fluoroolefins of the formula cyclo-[CX═CY(CZW) n —], wherein X, Y, Z, and W, independently, are H or F, and n is an integer from 2 to 5; and

(iii) fluoroolefins selected from the group consisting of:

1,2,3,3,3-pentafluoro-1-propene (CHF═CFCF 3 ), 1,1,3,3,3-pentafluoro-1-propene (CF 2 ═CHCF 3 ), 1,1,2,3,3-pentafluoro-1-propene (CF 2 ═CFCHF 2 ), 1,2,3,3-tetrafluoro-1-propene (CHF═CFCHF 2 ), 2,3,3,3-tetrafluoro-1-propene (CH 2 ═CFCF 3 ), 1,3,3,3-tetrafluoro-1-propeneCHF═CHCF 3 ), 1,1,2,3-tetrafluoro-1-propene (CF 2 ═CFCH 2 F), 1,1,3,3-tetrafluoro-1-propene (CF 2 ═CHCHF 2 ), 1,2,3,3-tetrafluoro-1-propene (CHF═CFCHF 2 ), 3,3,3-trifluoro-1-propene (CH 2 ═CHCF 3 ), 2,3,3-trifluoro-1-propene (CHF 2 CF═CH 2 ); 1,1,2-trifluoro-1-propene (CH 3 CF═CF 2 ); 1,2,3-trifluoro-1-propene (CH 2 FCF═CF 2 ); 1,1,3-trifluoro-1-propene (CH 2 FCH═CF 2 ); 1,3,3-trifluoro-1-propene (CHF 2 CH═CHF); 1,1,1,2,3,4,4,4-octafluoro-2-butene (CF 3 CF═CFCF 3 ); 1,1,2,3,3,4,4,4-octafluoro-1-butene (CF 3 CF 2 CF═CF 2 ); 1,1,1,2,4,4,4-heptafluoro-2-butene (CF 3 CF═CHCF 3 ); 1,2,3,3,4,4,4-heptafluoro-1-butene (OHF═CFCF 2 CF 3 ); 1,1,1,2,3,4,4-heptafluoro-2-butene (CHF 2 CF═CFCF 3 ); 1,3,3,3-tetrafluoro-2-(trifluoromethyl)-1-propene ((CF 3 ) 2 C═CHF); 1,1,3,3,4,4,4-heptafluoro-1-butene (CF 2 ═CHCF 2 CF 3 ); 1,1,2,3,4,4,4-heptafluoro-1-butene (CF 2 ═CFCHFCF 3 ); 1,1,2,3,3,4,4-heptafluoro-1-butene (CF 2 ═CFCF 2 CHF 2 ); 2,3,3,4,4,4-hexafluoro-1-butene (CF 3 CF 2 CF═CH 2 ); 1,3,3,4,4,4-hexafluoro-1-butene (CHF═CHCF 2 CF 3 ); 1,2,3,4,4,4-hexafluoro-1-butene (CHF═CFCHFCF 3 ); 1,2,3,3,4,4-hexafluoro-1-butene (CHF═CFCF 2 CHF 2 ); 1,1,2,3,4,4-hexafluoro-2-butene (CHF 2 CF═CFCHF 2 ); 1,1,1,2,3,4-hexafluoro-2-butene (CH 2 FCF═CFCF 3 ); 1,1,1,2,4,4-hexafluoro-2-butene (CHF 2 CH═CFCF 3 ); 1,1,1,3,4,4-hexafluoro-2-butene (CF 3 CH═CFCHF 2 ); 1,1,2,3,3,4-hexafluoro-1-butene (CF 2 ═CFCF 2 CH 2 F); 1,1,2,3,4,4-hexafluoro-1-butene (CF 2 ═CFCHFCHF 2 ); 3,3,3-trifluoro-2-(trifluoromethyl)-1-propene (CH 2 ═C(CF 3 ) 2 ); 1,1,1,2,4-pentafluoro-2-butene (CH 2 FCH═CFCF 3 ); 1,1,1,3,4-pentafluoro-2-butene (CF 3 CH═CFCH 2 F); 3,3,4,4,4-pentafluoro-1-butene (CF 3 CF 2 CH═CH 2 ); 1,1,1,4,4-pentafluoro-2-butene (CHF 2 CH═CHCF 3 ); 1,1,1,2,3-pentafluoro-2-butene (CH 3 CF═CFCF 3 ); 2,3,3,4,4-pentafluoro-1-butene (CH 2 ═CFCF 2 CHF 2 ); 1,1,2,4,4-pentafluoro-2-butene (CHF 2 CF═CHCHF 2 ); 1,1,2,3,3-pentafluoro-1-butene (CH 3 CF 2 CF═CF 2 ); 1,1,2,3,4-pentafluoro-2-butene (CH 2 FCF═CFCHF 2 ); 1,1,3,3,3-pentafluoro-2-methyl-1-propene (CF 2 ═C(CF 3 )(CH 3 )); 2-(difluoromethyl)-3,3,3-trifluoro-1-propene (CH 2 ═C(CHF 2 )(CF 3 )); 2,3,4,4,4-pentafluoro-1-butene (CH 2 ═CFCHFCF 3 ); 1,2,4,4,4-pentafluoro-1-butene (CHF═CFCH 2 CF 3 ); 1,3,4,4,4-pentafluoro-1-butene (CHF═CHCHFCF 3 ); 1,3,3,4,4-pentafluoro-1-butene (CHF═CHCF 2 CHF 2 ); 1,2,3,4,4-pentafluoro-1-butene (CHF═CFCHFCHF 2 ); 3,3,4,4-tetrafluoro-1-butene (CH 2 ═CHCF 2 CHF 2 ); 1,1-difluoro-2-(difluoromethyl)-1-propene (CF 2 ═C(CHF 2 )(CH 3 )); 1,3,3,3-tetrafluoro-2-methyl-1-propene (CHF═C(CF 3 )(CH 3 )); 3,3-difluoro-2-(difluoromethyl)-1-propene (CH 2 ═C(CHF 2 ) 2 ); 1,1,1,2-tetrafluoro-2-butene (CF 3 CF═CHCH 3 ); 1,1,1,3-tetrafluoro-2-butene (CH 3 CF═CHCF 3 ); 1,1,1,2,3,4,4,5,5,5-decafluoro-2-pentene (CF 3 CF═CFCF 2 CF 3 ); 1,1,2,3,3,4,4,5,5,5-decafluoro-1-pentene (CF 2 ═CFCF 2 CF 2 CF 3 ); 1,1,1,4,4,4-hexafluoro-2-(trifluoromethyl)-2-butene ((CF 3 ) 2 C═CHCF 3 ); 1,1,1,2,4,4,5,5,5-nonafluoro-2-pentene (CF 3 CF═CHCF 2 CF 3 ); 1,1,1,3,4,4,5,5,5-nonafluoro-2-pentene (CF 3 CH═CFCF 2 CF 3 ); 1,2,3,3,4,4,5,5,5-nonafluoro-1-pentene (CHF═CFCF 2 CF 2 CF 3 ); 1,1,3,3,4,4,5,5,5-nonafluoro-1-pentene (CF 2 ═CHCF 2 CF 2 CF 3 ); 1,1,2,3,3,4,4,5,5-nonafluoro-1-pentene (CF 2 ═CFCF 2 CF 2 CHF 2 ); 1,1,2,3,4,4,5,5,5-nonafluoro-2-pentene (CHF 2 CF═CFCF 2 CF 3 ); 1,1,1,2,3,4,4,5,5-nonafluoro-2-pentene (CF 3 CF═CFCF 2 CHF 2 ); 1,1,1,2,3,4,5,5,5-nonafluoro-2-pentene (CF 3 CF═CFCHFCF 3 ); 1,2,3,4,4,4-hexafluoro-3-(trifluoromethyl)-1-butene (CHF═CFCF(CF 3 ) 2 ); 1,1,2,4,4,4-hexafluoro-3-(trifluoromethyl)-1-butene (CF 2 ═CFCH(CF 3 ) 2 ); 1,1,1,4,4,4-hexafluoro-2-(trifluoromethyl)-2-butene (CF 3 CH═C(CF 3 ) 2 ); 1,1,3,4,4,4-hexafluoro-3-(trifluoromethyl)-1-butene (CF 2 ═CHCF(CF 3 ) 2 ); 2,3,3,4,4,5,5,5-octafluoro-1-pentene (CH 2 ═CFCF 2 CF 2 CF 3 ); 1,2,3,3,4,4,5,5-octafluoro-1-pentene (CHF═CFCF 2 CF 2 CHF 2 ); 3,3,4,4,4-pentafluoro-2-(trifluoromethyl)-1-butene (CH 2 ═C(CF 3 )CF 2 CF 3 ); 1,1,4,4,4-pentafluoro-3-(trifluoromethyl)-1-butene (CF 2 ═CHCH(CF 3 ) 2 ); 1,3,4,4,4-pentafluoro-3-(trifluoromethyl)-1-butene (CHF═CHCF(CF 3 ) 2 ); 1,1,4,4,4-pentafluoro-2-(trifluoromethyl)-1-butene (CF 2 ═C(CF 3 )CH 2 CF 3 ); 3,4,4,4-tetrafluoro-3-(trifluoromethyl)-1-butene ((CF 3 ) 2 CFCH═CH 2 ); 3,3,4,4,5,5,5-heptafluoro-1-pentene (CF 3 CF 2 CF 2 CH═CH 2 ); 2,3,3,4,4,5,5-heptafluoro-1-pentene (CH 2 ═CFCF 2 CF 2 CHF 2 ); 1,1,3,3,5,5,5-heptafluoro-1-butene (CF 2 ═CHCF 2 CH 2 CF 3 ); 1,1,1,2,4,4,4-heptafluoro-3-methyl-2-butene (CF 3 CF═C(CF 3 )(CH 3 )); 2,4,4,4-tetrafluoro-3-(trifluoromethyl)-1-butene (CH 2 ═CFCH(CF 3 ) 2 ); 1,4,4,4-tetrafluoro-3-(trifluoromethyl)-1-butene (CHF═CHCH(CF 3 ) 2 ); 1,1,1,4-tetrafluoro-2-(trifluoromethyl)-2-butene (CH 2 FCH═C(CF 3 ) 2 ); 1,1,1,3-tetrafluoro-2-(trifluoromethyl)-2-butene (CH 3 CF═C(CF 3 ) 2 ); 1,1,1-trifluoro-2-(trifluoromethyl)-2-butene ((CF 3 ) 2 C═CHCH 3 ); 3,4,4,5,5,5-hexafluoro-2-pentene (CF 3 CF 2 CF═CHCH 3 ); 1,1,1,4,4,4-hexafluoro-2-methyl-2-butene (CF 3 C(CH 3 )═CHCF 3 ); 3,3,4,5,5,5-hexafluoro-1-pentene (CH 2 ═CHCF 2 CHFCF 3 ); 4,4,4-trifluoro-2-(trifluoromethyl)-1-butene (CH 2 ═C(CF 3 )CH 2 CF 3 ); 1,1,2,3,3,4,4,5,5,6,6,6-dodecafluoro-1-hexene (CF 3 (CF 2 ) 3 CF═CF 2 ); 1,1,1,2,2,3,4,5,5,6,6,6-dodecafluoro-3-hexene (CF 3 CF 2 CF═CFCF 2 CF 3 ); 1,1,1,4,4,4-hexafluoro-2,3-bis(trifluoromethyl)-2-butene ((CF 3 ) 2 C═C(CF 3 ) 2 ); 1,1,1,2,3,4,5,5,5-nonafluoro-4-(trifluoromethyl)-2-pentene ((CF 3 ) 2 CFCF═CFCF 3 ); 1,1,1,4,4,5,5,5-octafluoro-2-(trifluoromethyl)-2-pentene ((CF 3 ) 2 C═CHC 2 F 5 ); 1,1,1,3,4,5,5,5-octafluoro-4-(trifluoromethyl)-2-pentene ((CF 3 ) 2 CFCF═CHCF 3 ); 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene (CF 3 CF 2 CF 2 CF 2 CH═CH 2 ); 4,4,4-trifluoro-3,3-bis(trifluoromethyl)-1-butene (CH 2 ═CHC(CF 3 ) 3 ); 1,1,1,4,4,4-hexafluoro-3-methyl-2-(trifluoromethyl)-2-butene ((CF 3 ) 2 C═C(CH 3 )(CF 3 )); 2,3,3,5,5,5-hexafluoro-4-(trifluoromethyl)-1-pentene (CH 2 ═CFCF 2 CH(CF 3 ) 2 ); 1,1,1,2,4,4,5,5,5-nonafluoro-3-methyl-2-pentene (CF 3 CF═C(CH 3 )CF 2 CF 3 ); 1,1,1,5,5,5-hexafluoro-4-(trifluoromethyl)-2-pentene (CF 3 CH═CHCH(CF 3 ) 2 ); 3,4,4,5,5,6,6,6-octafluoro-2-hexene (CF 3 CF 2 CF 2 CF═CHCH 3 ); 3,3,4,4,5,5,6,6-octafluorol-hexene (CH 2 ═CHCF 2 CF 2 CF 2 CHF 2 ); 1,1,1,4,4-pentafluoro-2-(trifluoromethyl)-2-pentene ((CF 3 ) 2 C═CHCF 2 CH 3 ); 4,4,5,5,5-pentafluoro-2-(trifluoromethyl)-1-pentene (CH 2 ═C(CF 3 )CH 2 C 2 F 5 ); 3,3,4,4,5,5,5-heptafluoro-2-methyl-1-pentene (CF 3 CF 2 CF 2 C(CH 3 )═CH 2 ); 4,4,5,5,6,6,6-heptafluoro-2-hexene (CF 3 CF 2 CF 2 CH═CHCH 3 ); 4,4,5,5,6,6,6-heptafluoro-1-hexene (CH 2 ═CHCH 2 CF 2 C 2 F 5 ); 1,1,1,2,2,3,4-heptafluoro-3-hexene (CF 3 CF 2 CF═CFC 2 H 5 ); 4,5,5,5-tetrafluoro-4-(trifluoromethyl)-1-pentene (CH 2 ═CHCH 2 CF(CF 3 ) 2 ); 1,1,1,2,5,5,5-heptafluoro-4-methyl-2-pentene (CF 3 CF═CHCH(CF 3 )(CH 3 )); 1,1,1,3-tetrafluoro-2-(trifluoromethyl)-2-pentene ((CF 3 ) 2 C═CFC 2 H 5 ); 1,1,1,2,3,4,4,5,5,6,6,7,7,7-tetradecafluoro-2-heptene (CF 3 CF═CFCF 2 CF 2 C 2 F 5 ); 1,1,1,2,2,3,4,5,5,6,6,7,7,7-tetradecafluoro-3-heptene (CF 3 CF 2 CF═CFCF 2 C 2 F 5 ); 1,1,1,3,4,4,5,5,6,6,7,7,7-tridecafluoro-2-heptene (CF 3 CH═CFCF 2 CF 2 C 2 F 5 ); 1,1,1,2,4,4,5,5,6,6,7,7,7-tridecafluoro-2-heptene (CF 3 CF═CHCF 2 CF 2 C 2 F 5 ); 1,1,1,2,2,4,5,5,6,6,7,7,7-tridecafluoro-3-heptene (CF 3 CF 2 CH═CFCF 2 C 2 F 5 ); and 1,1,1,2,2,3,5,5,6,6,7,7,7-tridecafluoro-3-heptene (CF 3 CF 2 CF═CHCF 2 C 2 F 5 ).

8. The composition of claim 1 comprising:

a. at least one fluoroolefin selected from the group consisting of HFC-1225ye, HFC-1234yf, HFC-1234ze and HFC-1243zf; and

b. an effective amount of at least one stabilizer comprising a phenol selected from the group consisting of 2,6-di-tert-butyl-4-methylphenol; 2,6-di-tert-butyl-4-ethylphenol; 2,4-dimethyl-6-tertbutylphenol; tocopherol; hydroquinone; t-butyl hydroquinone; 4,4′-thio-bis(2-methyl-6-tert-butylphenol); 4,4′-thiobis(3-methyl-6-tertbutylphenol); 2,2′-thiobis(4-methyl-6-tert-butylphenol); 4,4′-methylenebis(2,6-di-tert-butylphenol); 4,4′-bis(2,6-di-tert-butylphenol); 2,2′-methylenebis(4-ethyl-6-tertbutylphenol); 2,2′-methylenebis(4-methyl-6-tert-butylphenol); 4,4-butylidenebis(3-methyl-6-tert-butylphenol); 4,4-isopropylidenebis(2,6-di-tert-butylphenol); 2,2′-methylenebis(4-methyl-6-nonylphenol); 2,2′-isobutylidenebis(4,6-dimethylphenol; 2,2′-methylenebis(4-methyl-6-cyclohexylphenol, 2,2′-methylenebis(4-ethyl-6-tert-butylphenol); butylated hydroxyl toluene (BHT); 2,6-di-tert-alpha-dimethylamino-p-cresol; 4,4-thiobis(6-tert-butyl-m-cresol; acylaminophenols; 2,6-di-tert-butyl-4(N,N′-dimethylaminomethylphenol); bis(3-methyl-4-hydroxy-5-tert-butylbenzyl)sulfide; bis(3,5-di-tert-butyl-4-hydroxybenzyl)sulfide and mixtures thereof.

9. The composition of claim 1 , further comprising a 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.

10. The composition of claim 1 , wherein said functionalized perfluoropolyethers comprise perfluoropolyether- or perfluoroalkyl-containing and phosphorus-containing partially esterified aryl phosphates, aryl phosphonates or salts thereof.

11. The composition of claim 10 , wherein said functionalized perfluoropolyethers contain either (i) a mono- or poly-alkylene oxide linking group between the phosphorus and a fluorocarbon group, or (ii) no linking group between the phosphorus and fluorocarbon.

12. The composition of claim 1 wherein said functionalized perfluoropolyether stabilizers are represented by Formula B,

which contain either a perfluoroalkyl or perfluoropolyether side chain.

13. The composition of claim 1 wherein said functionalized perfluoropolyether stabilizers are perfluoropolyether alkyl alcohols comprising a perfluoropolyether segment and one or more alcohols segments having a general formula, —CH 2 (C q H 2q )OH, wherein—C q H 2q represents a divalent linear or branched alkyl radical where q is an integer from 1 to about 10.

14. The composition of claim 1 wherein said functionalized perfluoropolyether stabilizers comprise substituted aryl pnictogen compositions having the structure [R f 1 —(C t R (u+v) )] m E(O) n (C t R 1 (u+v+1) ) (3−m) , wherein R f 1 is a fluoropolyether chain having a formula weight ranging from about 400 to about 15,000, comprises repeat units, and is selected from the group consisting of:

(a) J-O—(CF(CF 3 )CF 2 O) c (CFXO) d CFZ—;

(b) J 1 -O—(CF 2 CF 2 O) e (CF 2 O) f CFZ 1 —;

(c) J 2 -O—(CF(CF 3 )CF 2 O) j CF(CF 3 )CF 2 —;

(d) J 3 -O—(CQ 2 —CF 2 CF 2 —O) k —CQ 2 —CF 2 —;

(e) J 3 -O—(CF(CF 3 )CF 2 O) g (CF 2 CF 2 O) h (CFXO) i —CFZ—;

(f) J 4 -O—(CF 2 CF 2 O) r CF 2 —; and

(h) combinations of two or more thereof

wherein

J is a fluoroalkyl group selected from the group consisting of CF 3 , C 2 F 5 , C 3 F 7 , CF 2 Cl, C 2 F 4 Cl, C 3 F 6 Cl, and combinations of two or more thereof;

c and d are numbers such that the ratio of c:d ranges from about 0.01 to about 0.5;

X is F, CF 3 , or combinations thereof;

Z is F, Cl or CF 3 ;

J 1 is a fluoroalkyl group selected from the group consisting of CF 3 , C 2 F 5 , C 3 F 7 , CF 2 Cl, C 2 F 4 Cl, and combinations of two or more thereof;

e and f are numbers such that the ratio of el ranges from about 0.3 to about 5;

Z 1 is F or Cl;

J 2 is C 2 F 5 , C 3 F 7 , or combinations thereof;

j is an average number such that the formula weight of R f ranges from about 400 to about 15,000;

J 3 is selected from the group consisting of CF 3 , C 2 F 5 , C 3 F 7 , and combinations of two or more thereof;

k is an average number such that the formula weight of R f ranges from about 400 to about 15,000;

each Q is independently F, Cl, or H;

g, h and i are numbers such that (g+h) ranges from about 1 to about 50, the ratio of i:(g+h) ranges from about 0.1 to about 0.5;

J 4 is CF 3 , C 2 F 5 , or combinations thereof;

r is an average number such that the formula weight of R f ranges from about 400 to about 15,000; and

each R and R 1 is independently H, a C 1 -C 10 alkyl, a halogen, OR 3 , OH, SO 3 M, NR 2 2 , R 3 OH, R 3 SO 3 M, R 3 NR 2 2 , R 3 NO 2 , R 3 CN, C(O)OR 3 , C(O)OM, C(O)R 3 , or C(O)NR 2 2 , or combinations of two or more thereof;

wherein

R 2 is independently H, C 1 -C 10 alkyl, or combinations of two or more thereof;

R 3 is a C 1 -C 10 alkyl; and

M is hydrogen or a metal, preferably not aluminum;

t is equal to (6+u);

u is any combination of 0, 2, 4, 6, 8, 10, 12, 14, 16;

v is independently either 2 or 4;

n is 0 or 1;

E is P, As, or Sb; and

m is greater than about 0.5 to about 3, provided that, when E =P, m =3.0 and t =6, R cannot be exclusively H or contain F.

15. The composition of claim 1 wherein the functionalized perfluoropolyether stabilizers of the present invention comprise aryl perfluoropolyethers, which are monofunctional aryl perfluoropolyethers having the formula of R f —(Y) a —(C t R (u+v) —(O—C t R 1 (u+v) ) b —R, difunctional aryl perfluoropolyethers having the formula of R f 1 —[(Y) a —(C t R (u+v) )—(O—C t R 1 (u+v) ) b —R] 2 , or combinations thereof, wherein

each of R f and R f 1 has a formula weight of about 400 to about 15,000;

R f comprises repeat units selected from the group consisting of

(a) J-O—(CF(CF 3 )CF 2 O) c (CFXO) d CFZ—,

(b) J 1 -O—(CF 2 CF 2 O) e ,(CF 2 O) f CFZ 1 —,

(c) J 2 -O—(CF(CF 3 )CF 2 O) j CF(CF 3 )—,

(d) J 3 -O—(CQ 2 —CF 2 CF 2 —O) k —CQ 2 —,

(e) J 3 -O—(CF(CF 3 )CF 2 O) g (CF 2 CF 2 O) h (CFX—O)—CFZ—,

(f) J 4 -O—(CF 2 CF 2 O) k ,CF 2 —, and

(g) combinations of two or more thereof; and

where

the units with formulae CF 2 CF 2 O and CF 2 O are randomly distributed along the chain;

J is CF 3 , C 2 F 5 , C 3 F 7 , CF 2 Cl, C 2 F 4 Cl, C 3 F 6 Cl, or combinations of two or more thereof;

c and d are numbers such that the c/d ratio ranges from about 0.01 to about 0.5;

X is —F, —CF 3 , or combinations thereof;

Z is —F, —Cl or —CF 3 ;

Z 1 is —F or —Cl,

J 1 is CF 3 , C 2 F 5 , C 3 F 7 , CF 2 Cl, C 2 F 4 Cl, or combinations of two or more thereof;

e and f are numbers such that the e/f ratio ranges from about 0.3 to about 5;

J 2 is —C 2 F 5 , —C 3 F 7 , or combinations thereof;

j is an average number such that the formula weight of R f ranges from about 400 to about 15,000;

J 3 is CF 3 , C 2 F 5 , C 3 F 7 , or combinations of two or more thereof;

k is an average number such that the formula weight of R f ranges from about 400 to about 15,000;

each Q is independently —F, —Cl, or —H;

g, h and i are numbers such that (g+h) ranges from about 1 to about 50, the i/(g+h) ratio ranges from about 0.1 to about 0.5;

J 4 is CF 3 , C 2 F 5 , or combinations thereof;

k′ is an average number such that the formula weight of R f ranges from about 400 to about 15,000;

each R is independently —H, a halogen, —OH, —SO 3 M, NR 3 2 , —NO 2 , —R 4 OH, —R 4 SO 3 M, —R 4 NR 3 2 , —R 4 NO 2 , —R 4 CN, —C(O)R 4 , —C(O)OM, —C(O)R 4 , —C(O)NR 3 2 , or combinations of two or more thereof; except that when b =0, R cannot be four hydrogen atoms and —OH, or —Br, or —NH 2 ; or R cannot be solely H or —NO 2 , or combinations thereof;

each R 1 is independently H, —R 4 ,—OR 4 , a halogen, —OH, —SO 3 M, —NR 3 2 , —NO 2, —CN, —R 4 OH, —R 4 SO 3 M, —R 4 NR 3 2 , —R 4 NO 2 , —R 4 CN, —C(O)OR 4 , —C(O)OM, —C(O)R 4 , C(O)NR 3 2 , or combinations of two or more thereof provided that if b =0, the combination of R and R 2 cannot be four or more hydrogen atoms and —OH, —Br, —NH 2 , or —NO 2 ;

each R 3 is independently H, C 1 -C 10 alkyl, or combinations of two or more thereof;

R 4 is a C 1 -C 10 alkyl;

M is a hydrogen or metal ion;

a is 0 or 1;

b is 0-5;

Y is a divalent radical —CH 2 OCH 2 —, —(CH 2 ) 0 —O—, —(CF 2 ) n —, —CF 2 O—, —CF 2 OCF 2 —, —C(O)—, —C(S)—, or combinations of two or more thereof;

n is about 1 to about 5;

o is about 2 to about 5;

t is equal to 6+u;

u is any combination of 0, 2, 4, 6, 8, 10, 12, 14, 16;

v is independently either 2 or 4;

Rf 1 is —(CF 2 CF 2 O) e ,(CF 2 O) f CF 2 —, —(C 3 F 6 O) p (CF 2 CF 2 O) q (CFXO ) r CF 2 —, —(CF 2 CF 2 O)(C 3 F 6 O) w CF(CF 3 )—, —CF(CF 3 )O(C 3 F 6 O) w —Rf 2 —O (C 3 F 6 O) w CF(CF 3 )—, —((CQ 2 )CF 2 CF 2 O),CF 2 CF 2 —, or combinations of two or more thereof;

where

e, f, X, and Q are as defined above;

p, q and r are numbers such that (p+q) ranges from 1 to 50 and r/(p+q) ranges from 0.1 to 0.05;

each w is independently 2 to 45;

Rf 2 is linear or branched —C m F 2m —;

m is 1-10; and

s is an average number such that the formula weight of R f 1 ranges from 400 to 15,000.

16. A process for producing cooling comprising condensing the composition of claim 1 and thereafter evaporating said composition in the vicinity of a body to be cooled.

17. A process for producing heat comprising condensing the composition of claim 1 in the vicinity of a body to be heated, and thereafter evaporating said composition.

18. A method for stabilizing a composition comprising at least one fluoroolefin, said method comprising adding an effective amount of a stabilizer comprising a phenol and at least one compound selected from the group consisting of functionalized perfluoropolyethers to said composition comprising at least one fluoroolefin.

19. A method for reducing degradation of a composition comprising at least one fluoroolefin, wherein said degradation is caused by the presence of inadvertent air in a refrigeration, air-conditioning or heat pump system, said method comprising adding a stabilizer comprising at least one phenol and at least one compound selected from the group consisting of functionalized perfluoropolyethers to said composition comprising at least one fluoroolefin.

20. A method for reducing reaction with oxygen for a composition comprising at least one fluoroolefin, said method comprising adding an effective amount of stabilizer comprising at least one phenol and at least one compound selected from the group consisting of functionalized perfluoropolyethers to said composition comprising at least one fluoroolefin.