Granted Patent B2

US 11,851,602 · App. 17/409,311 · Granted Dec 26, 2023

Inventors: Andrew Edward Feiring (Wilmington, DE); Viacheslav A Petrov (Hockessin, DE); Barbara Haviland Minor (The Villages, FL); Mario Joseph Nappa (Leesburg, FL); Nandini C Mouli (Reisterstown, MD); Thomas Joseph Leck (Hockessin, DE); Jon Lee Howell (Bear, DE)

Assignee: THE CHEMOURS COMPANY FC, LLC

C09K5/045F25B39/02C09K2205/10C09K2205/102C09K2205/104C09K2205/11C09K2205/126C09K2205/132C09K2205/134C09K2205/24

Abstract

Claims (34)

1. A composition consisting of at least one fluoroolefin and an effective amount of a stabilizer consisting of:

a. at least one compound selected from the group consisting of an epoxide or a fluorinated epoxide represented by Formula A, wherein each of R 2 through R 5 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 R 2 through R 5 is a fluoroalkyl group;

b. at least one compound selected from the group consisting of organophosphates;

and a hydrocarbon.

2. The composition of claim 1 , wherein the epoxide is selected from the group consisting of 1,2-propylene oxide, 1,2-butylene oxide, butylphenylglycidyl ether, pentylphenylglycidyl ether, hexylphenylglycidyl ether, heptylphenylglycidyl ether, octylphenylglycidyl ether, nonylphenylglycidyl ether, decylphenylglycidyl ether, glycidyl methylphenylether, 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, trifluoromethyloxirane, 1,1-bis(trifluoromethyl)oxirane, and mixtures thereof.

3. The composition of claim 1 , wherein the organophosphate is selected from the group consisting of amine phosphates, trialkyl phosphates, triaryl phosphates, mixed alkyl-aryl phosphates, and cyclic phosphates.

4. The composition of claim 3 , wherein the organophosphate is selected from the group consisting of trimethyl phosphate; triethyl phosphate; tributyl phosphate; trioctyl phosphate; tri(2-ethylhexyl)phosphate; triphenyl phosphate; tricresyl phosphate; trixylenyl phosphate; isopropylphenyl phenyl phosphate; bis(t-butylphenyl) phenyl phosphate; butylated triphenyl phosphate; tert-butylated triphenyl phosphate; and iso-propylated triphenyl phosphate.

5. 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′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-propene, CHF═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 (CHF═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 ═CFCHFCRF2); 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-octafluoro1-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 ).

6. The composition of claim 5 , wherein the fluoroolefin is selected from the group consisting of 1,1,1,4,4,4-hexafluorobut-2-ene; 1,1,1,4,4,5,5,5-octafluoropent-2-ene; 1,1,1,4,4,5,5,6,6,6-decafluorohex-2-ene; 1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene; 1,1,1,2,2,5,5,6,6,6-decafluorohex-3-ene; 1,1,1,4,4,5,5,6,6,7,7,7-dodecafluorohept-2-ene; 1,1,1,4,4,5,6,6,6-nonafluoro-5-(trifluoromethyl)hex-2-ene; 1,1,1,4,5,5,6,6,6-nonafluoro-4-(trifluoromethyl)hex-2-ene; 1,1,1,5,5,5-hexafluoro-4,4-bis(trifluoromethyl)pent-2-ene; 1,1,1,2,2,5,5,6,6,7,7,7-dodecafluorohept-3-ene; 1,1,1,2,2,5,6,6,6-nonafluoro-5-(trifluoromethyl)hex-3-ene; 1,1,1,4,4,5,5,6,6,7,7,8,8,8-tetradecafluorooct-2-ene; 1,1,1,4,4,5,5,6,7,7,7-undecafluoro-6-(trifluoromethyl)hept-2-ene; 1,1,1,5,5,6,6,6-octafluoro-4,4-bis(trifluoromethyl)hex-2-ene; 1,1,1,2,2,5,5,6,6,7,7,8,8,8-tetradecafluorooct-3-ene; 1,1,1,2,2,5,5,6,7,7,7-undecafluoro-6-(trifluoromethyl)hept-3-ene; 1,1,1,2,2,5,6,6,7,7,7-undecafluoro-5-(trifluoromethyl)hept-3-ene; 1,1,1,2,2,6,6,6-octafluoro-5,5-bis(trifluoromethyl)hex-3-ene; 1,1,1,2,2,3,3,6,6,7,7,8,8,8-tetradecafluorooct-4-ene; 1,1,1,2,5,6,6,6-octafluoro-2,5-bis(trifluoromethyl)hex-3-ene; 1,1,1,2,5,5,6,6,7,7,7-undecafluoro-2-(trifluoromethyl)hept-3-ene; 1,1,1,4,4,5,5,6,6,7,7,8,8,9,9,9-hexadecafluoronon-2-ene; 1,1,1,4,5,5,6,6,7,7,8,8,8-tridecafluoro-4-(trifluoromethyl)hept-2-ene; 1,1,1,6,6,6-octafluoro-4,4-bis(trifluoromethyl)hept-2-ene; 1,1,1,2,2,5,5,6,6,7,7,8,8,9,9,9-hexadecafluoronon-3-ene; 1,1,1,2,2,5,5,6,6,7,8,8,8-tridecafluoro-7-(trifluoromethyl)oct-3-ene; 1,1,1,2,2,6,6,7,7,7-decafluoro-5,5-bis(trifluoromethyl)hept-3-ene; 1,1,1,2,2,3,3,6,6,7,7,8,8,9,9,9-hexadecafluoronon-4-ene; 1,1,1,2,2,3,3,6,6,7,8,8,8-tridecafluoro-7-(trifluoromethyl)oct-4-ene; 1,1,1,2,2,3,3,6,7,7,8,8,8-tridecafluoro-6-(trifluoromethyl)oct-4-ene; 1,1,1,5,5,6,6,7,7,7-decafluoro-2,2-bis(trifluoromethyl)hept-3-ene; 1,1,1,2,5,5,6,6,7,7,8,8,8-tridecafluoro-2(trifluoromethyl)oct-3-ene; 1,1,1,2,5,5,6,7,7,7-decafluoro-2,6-bis(trifluoromethyl)hept-3-ene; 1,1,1,2,5,6,6,7,7,7-decafluoro-2,5-bis(trifluoromethyl)hept-3-ene; 1,1,1,2,6,6,6-heptafluoro-2,5,5-tris(trifluoromethyl)hex-3-ene; 1,1,1,2,2,5,5,6,6,7,7,8,8,9,9,10,10,10-octadecafluorodec-3-ene; 1,1,1,2,2,5,6,6,7,7,8,8,9,9,9-pentadecafluoro-5-(trifluoromethyl)non-3-ene; 1,1,1,2,2,6,6,7,7,8,8,8-dodecafluoro-5,5-bis(trifluoromethyl)oct-3-ene; 1,1,1,2,2,3,3,6,6,7,7,8,8,9,9,10,10,10-octadecafluorodec-4-ene; 1,1,1,2,2,3,3,6,6,7,7,8,9,9,9-pentadecafluoro-8-(trifluoromethyl)non-4-ene; 1,1,1,2,2,3,3,7,7,8,8,8-dodecafluoro-6,6-bis(trifluoromethyl)oct-4-ene; 1,1,1,2,5,5,6,6,7,7,8,8,9,9,9-pentadecafluoro-2-(trifluoromethyl)non-3-ene; 1,1,1,2,5,5,6,6,7,8,8,8-dodecafluoro-2,7-bis(trifluoromethyl)oct-3-ene; 1,1,1,2,6,6,7,7,7-nonafluoro-2,5,5-tris(trifluoromethyl)hept-3-ene; 1,1,1,2,2,3,3,4,4,7,7,8,8,9,9,10,10,10-octadecafluorodec-5-ene; 1,1,1,2,3,3,6,6,7,7,8,8,9,9,9-pentadecafluoro-2-(trifluoromethyl)non-4-ene; 1,1,1,2,2,3,6,6,7,7,8,8,9,9,9-pentadecafluoro-3-(trifluoromethyl)non-4-ene; 1,1,1,5,5,6,6,7,7,8,8,8-dodecafluoro-2,2,-bis(trifluoromethyl)oct-3-ene; 1,1,1,2,3,3,6,6,7,8,8,8-dodecafluoro-2,7-bis(trifluoromethyl)oct-4-ene; 1,1,1,2,3,3,6,7,7,8,8,8-dodecafluoro-2,6-bis(trifluoromethyl)oct-4-ene; 1,1,1,5,5,6,7,7,7-nonafluoro-2,2,6-tris(trifluoromethyl)hept-3-ene; 1,1,1,2,2,3,6,7,7,8,8,8-dodecafluoro-3,6-bis(trifluoromethyl)oct-4-ene; 1,1,1,5,6,6,7,7,7-nonafluoro-2,2,5-tris(trifluoromethyl)hept-3-ene; and 1,1,1,6,6,6-hexafluoro-2,2,5,5-tetrakis(trifluoromethyl)hex-3-ene.

7. The compositions of claim 5 , wherein the fluoroolefin is selected from the group consisting of 1,2,3,3,4,4-hexafluorocyclobutene; 3,3,4,4-tetrafluorocyclobutene; 3,3,4,4,5,5,-hexafluorocyclopentene; 1,2,3,3,4,4,5,5-octafluorocyclopentene; and 1,2,3,3,4,4,5,5,6,6-decafluorocyclohexene.

8. 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.

9. 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.

10. A refrigeration, air-conditioning, heat pump, or chiller system containing the composition of claim 1 .

11. A composition consisting of:

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

b. an effective amount of a stabilizer consisting of:

i. at least one compound selected from the group consisting of an epoxide and a fluorinated epoxide represented by Formula A, wherein each of R 2 through R 5 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 R 2 through R 5 is a fluoroalkyl group;

 and

ii. at least one organophosphate; and

c. a hydrocarbon.

12. The composition of claim 11 , wherein said hydrocarbon is selected from the group consisting of propane, n-butane, isobutane, cyclobutane, n-pentane, 2-methylbutane, 2,2-dimethylpropane, cyclopentane, n-hexane, 2-methylpentane, 2,2-dimethylbutane, 2,3-dimethylbutane, 3-methylpentane, cyclohexane, n-heptane, and cycloheptane.

13. A process for producing cooling comprising condensing the composition of claim 11 and thereafter evaporating said composition in the vicinity of a body to be cooled.

14. A process for producing heat comprising condensing the composition of claim 11 in the vicinity of a body to be heated, and thereafter evaporating said composition.

15. A refrigeration, air-conditioning, heat pump, or chiller system containing the composition of claim 11 .

16. A composition, consisting of at least one fluoroolefin and an effective amount of a stabilizer consisting of:

a. at least one compound selected from the group consisting of an epoxide or a fluorinated epoxide represented by Formula A, wherein each of R 2 through R 5 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 R 2 through R 5 is a fluoroalkyl group;

b. at least one compound selected from the group consisting of organophosphates;

a lubricant selected from the group consisting of mineral oils, alkylbenzenes, polyalphaolefins, silicone oils, polyoxyalkylene glycol ethers, polyol esters, polyvinylethers and mixtures thereof;

and a hydrocarbon.

17. A refrigeration, air-conditioning, heat pump, or chiller system containing the composition of claim 16 .

Assignments (2)

Continuity (9)