Processes for separation of fluoroolefins from hydrogen fluoride by azeotropic distillation

1. A process for separating a mixture comprising HF and fluoroolefin, said process comprising:

a. feeding the composition comprising HF and fluoroolefin to a first distillation column;

b. removing an azeotrope composition comprising HF and fluoroolefin as a first distillate and either i) HF or ii) fluoroolefin as a first column bottoms composition;

c. condensing the first distillate to form 2 liquid phases, being i) an HF-rich phase and ii) a fluoroolefin-rich phase and separating said 2 liquid phases in a decanter; and

d. recycling a first liquid phase enriched in the same compound that is removed as the first column bottoms, said first liquid phase being either i) HF-rich phase or ii) fluoroolefin-rich phase, back to the first distillation column.

2. The process of claim 1 , further comprising feeding a second liquid phase not recycled in step (d), said second liquid phase being either i) HF-rich phase or ii) fluoroolefin-rich phase, to a second distillation column, and recovering the compound not recovered in step (b) as the first column bottoms composition as the second column bottoms composition.

3. The process of claim 1 , wherein said fluoroolefin is 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:

tetrafluoroethylene (CF 2 ═CF 2 ); hexafluoropropene (CF 3 CF═CF 2 ); 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 ═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-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 ).

4. The process of claim 3 wherein said fluoroolefin comprises at least one compound selected from the group consisting of HFC-1225ye, HFC-1234ze, HFC-1234yf, and HFC-1243zf.

5. The process of claim 1 , wherein said fluoroolefin is present in a concentration greater than the azeotrope composition for hydrogen fluoride and said fluoroolefin, and wherein the first column bottoms composition is fluoroolefin essentially free of hydrogen fluoride, and wherein said first liquid phase is enriched in fluoroolefin.

6. The process of claim 5 further comprising:

i. feeding the hydrogen fluoride-rich phase from the decanter to a second distillation column, and

ii. recovering hydrogen fluoride essentially free of fluoroolefin from the bottom of the second distillation column.

7. The process of claim 6 , further comprising recycling a second distillate composition to the two liquid phases in the decanter.

8. The process of claim 1 , wherein hydrogen fluoride is present in a concentration greater than the azeotrope concentration for hydrogen fluoride and said fluoroolefin, and wherein the first column bottoms composition is hydrogen fluoride essentially free of fluoroolefin, and wherein said first liquid phase is enriched in hydrogen fluoride.

9. The process of claim 8 further comprising:

i. feeding the fluoroolefin-rich phase from the decanter to a second distillation column, and

ii. recovering fluoroolefin essentially free of hydrogen fluoride from the bottom of the second distillation column.

10. The process of claim 9 , further comprising recycling a second distillate composition to the two liquid phases in the decanter.

11. The process of claim 3 , wherein said 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-nonfluoro-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; 1,1,1,2,2,3,6,7,7,8,8,8-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.

12. The composition of claim 3 , wherein said 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.