KR101399203B1 - Compositions comprising fluoroolefins and uses thereof - Google Patents

Abstract

The present invention relates to a fluoroolefin composition. The fluoroolefin compositions of the present invention are useful as refrigerants or heat transfer fluids, as well as in methods of providing cooling or heating. In addition, the fluoroolefin compositions of the present invention can be used to replace currently used refrigerant or heat transfer fluid compositions having a higher global warming index.

Description

COMPOUND COMPRISING FLUOROOLEFINS AND USES THEREOF FIELD OF THE INVENTION The present invention relates to compositions comprising fluoroolefins,

<Cross reference (s) of related application (s)>

This application claims priority benefit of U.S. Provisional Application No. 60 / 732,581, filed November 1, 2005, and U.S. Patent Application No. 11 / 486,791, filed July 13, 2006.

The present invention relates to a composition comprising at least one fluoroolefin for use in a refrigeration, air conditioning or heating pump system. The compositions of the present invention are useful in methods of providing refrigeration or heating as heat transfer fluids and many other uses.

The refrigeration industry has been exploring alternative refrigerants for ozone-depleting chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs), which have been abolished as a result of the Montreal Accords for decades. The solution for most refrigerant producers was the commercialization of hydrofluorocarbon (HFC) refrigerants. HFC-134a, currently the most widely used HFC refrigerant, has an ozone depletion potential of zero and is therefore not affected by current regulations abolished as a result of the Montreal Accord.

Additional environmental regulations may ultimately lead to the global abolition of certain HFC refrigerants. Currently, the automotive industry is facing regulations related to the global warming index for refrigerants used in mobile air conditioning. Thus, there is now a great need in the mobile air conditioning market for finding new refrigerants with reduced global warming potentials. If regulations are applied more widely in the future, there will be a much greater need for refrigerants that can be used in all areas of the refrigeration and air conditioning industry.

Alternative refrigerants for the currently proposed HFC-134a include HFC-152a, pure hydrocarbons such as butane or propane, or "natural" refrigerants such as CO ₂ . Most of these proposed alternatives are toxic, flammable and / or have low energy efficiency. Therefore, new alternative refrigerants are being pursued.

It is an object of the present invention to provide new refrigerant compositions and heat transfer fluid compositions that provide unique features to meet the demand for low or zero ozone depletion potential and lower global warming index compared to current refrigerants .

According to the present invention,

(i) a compound of the formula E or ZR ¹ CH = CHR ² , wherein R ¹ and R ² are independently C ₁ to C ₆ perfluoroalkyl groups, wherein the total number of carbons in the compound is at least 5, Olefins;

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

(iii) 2,3,3-Trifluoro-1-propene (CHF ₂ CF = CH ₂ ); In 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); 2-butene to 1,1,1,2,3,4,4,4- octafluoro _{(CF 3 CF = CFCF 3)} ; A 1,1,2,3,3,4,4,4- octafluoro-1-butene _{(CF 3 CF 2 CF = CF} 2); 2-butene to 1,1,1,2,4,4,4- heptafluoropropane _{(CF 3 CF = CHCF 3)} ; 1,2,3,3,4,4,4-heptafluoro-1-butene (CHF = CFCF ₂ CF ₃ ); 2-butene (CHF ₂ CF = CFCF ₃₎ a 1,1,1,2,3,4,4- heptafluoropropane; As 1,3,3,3- tetrafluoroethane (trifluoromethyl) -2-1-propene _{((CF 3) 2 C =} CHF); 1,1,3,3,4,4,4- heptafluoro-1-butene as a _{(CF 2 = CHCF 2 CF 3} ); 1,1,2,3,4,4,4- heptafluoro-1-butene as a (CF ₂ = CFCHFCF _3); A 1,1,2,3,3,4,4- heptafluoro-1-butene _{(CF 2 = CFCF 2 CHF 2} ); A 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 as a _{(CHF = CHCF 2 CF 3)} ; 1-butene (CHF = CFCHFCF ₃₎ a 1,2,3,4,4,4- hexafluoro; 1,2,3,3,4,4-hexafluoro-1-butene (CHF = CFCF ₂ CHF ₂ ); 1,1,2,3,4,4- hexafluoro-2-butene as a _{(CHF 2 CF = CFCHF 2)} ; 1,1,1,2,3,4-hexafluoro- ₂ -butene (CH ₂ FCF = CFCF ₃ ); 2-butene (CHF ₂ CH = CFCF ₃₎ a 1,1,1,2,4,4- hexafluoro; 1,1,1,3,4,4- hexafluoro-2-butene as a _{(CF 3 CH = CFCHF 2)} ; 1-butene _{(CF 2 = CFCF 2 CH 2} F) to 1,1,2,3,3,4- hexafluoro; 1,1,2,3,4,4- hexafluoro-1-butene as a (CF ₂ = CFCHFCHF _2); 3,3,3-trifluoro (trifluoromethyl) -2-propene-1 _{(CH 2 = C (CF 3} ) 2); A 1,1,1,2,4- pentafluoro-2-butene _{(CH 2 FCH = CFCF 3)} ; 1,1,1,3,4- pentafluoro-2-butene as a _{(CF 3 CH = CFCH 2 F} ); 3,3,4,4,4- pentafluoro-1-butene with _{(CF 3 CF 2 CH = CH} 2); 1,1,1,4,4- pentafluorophenyl-2-butene _{(CHF 2 CH = CHCF 3)} ; 2-butene (CH ₃ CF = CFCF ₃₎ with 1,1,1,2,3- pentafluoropropane; 2,3,3,4,4- pentafluorophenyl-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- pentafluorophenyl-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 pentafluoroethyl-2-methyl-1-propene _{(CF 2 = C (CF 3} ) (CH 3)); 2- (difluoro-methyl) -3,3,3-trifluoro-1-propene _{(CH 2 = C (CHF 2} ) (CF 3)); 1-butene (CH ₂ = CFCHFCF ₃₎ with 2,3,4,4,4- pentafluoropropane; 1,2,4,4,4- pentafluorophenyl-1-butene _{(CHF = CFCH 2 CF 3)} ; 1,3,4,4,4- pentafluorophenyl-1-butene (CHF = CHCHFCF _3); 1,3,3,4,4- pentafluoro-1-butene as a _{(CHF = CHCF 2 CHF 2)} ; 1,2,3,4,4- pentafluorophenyl-1-butene (CHF = CFCHFCHF _2); 1-butene as 3,3,4,4- tetrafluoroethane _{(CH 2 = CHCF 2 CHF 2} ); 1,1-di (difluoromethyl) -2-fluoro-1-propene _{(CF 2 = C (CHF 2} ) (CH 3)); 2-methyl-1-propene _{(CHF = C (CF 3)} (CH 3)) to 1,3,3,3- tetrafluoroethane; 3,3-di (difluoromethyl) -2-fluoro-1-propene _{(CH 2 = C (CHF 2} ) 2); 2-butene-1,1,1,2-tetrafluoroethane _{(CF 3 CF = CHCH 3)} ; 2-butene as 1,1,1,3- tetrafluoroethane (CF ₃ CH = CHCF _3); 1,1,1,2,3,4,4,5,5,5- to deca-fluoro-2-pentene _{(CF 3 CF = CFCF 2 CF} 3); 1,1,2,3,3,4,4,5,5,5- to deca-fluoro-1-pentene _{(CF 2 = CFCF 2 CF 2} CF 3); A 1,1,1,4,4,4- hexafluoro (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); A 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)} ; A 1,2,3,4,4,4- hexafluoro (trifluoromethyl) -3-butene _{(CHF = CFCF (CF 3)} 2); A 1,1,2,4,4,4- hexafluoro (trifluoromethyl) -3-butene-1 _{(CF 2 = CFCH (CF 3} ) 2); A 1,1,1,4,4,4- hexafluoro (trifluoromethyl) -2-butene _{(CF 3 CH = C (CF} 3) 2); A 1,1,3,4,4,4- hexafluoro (trifluoromethyl) -3-butene-1 _{(CF 2 = CHCF (CF 3} ) 2); A 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 ); With 3,3,4,4,4- pentafluoropropane (trifluoromethyl) -2-butene _{(CH 2 = C (CF 3} ) CF 2 CF 3); With 1,1,4,4,4- pentafluoropropane (trifluoromethyl) -3-butene-1 (CF = CHCH ₂ (CF _{3) 2);} With 1,3,4,4,4- pentafluoropropane (trifluoromethyl) -3-butene _{(CHF = CHCF (CF 3)} 2); With 1,1,4,4,4- pentafluoropropane (trifluoromethyl) -2-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 ); A 3,3,4,4,5,5,5- heptafluoro-1-pentene _{(CF 3 CF 2 CF 2 CH} = CH 2); A 2,3,3,4,4,5,5- heptafluoro-1-pentene _{(CH 2 = CFCF 2 CF 2} CHF 2); A 1,1,3,3,5,5,5- heptafluoro-1-butene _{(CF 2 = CHCF 2 CH 2} CF 3); 3-methyl-2-butene as a 1,1,1,2,4,4,4- heptafluoropropane _{(CF 3 CF = C (CF} 3) (CH 3)); As 2,4,4,4- tetrafluoroethane (trifluoromethyl) -3-butene _{(CH 2 = CFCH (CF 3} ) 2); As 1,4,4,4- tetrafluoroethane (trifluoromethyl) -3-butene _{(CHF = CHCH (CF 3)} 2); As 1,1,1,4- tetrafluoroethane (trifluoromethyl) -2-butene _{(CH 2 FCH = C (CF} 3) 2); As 1,1,1,3- tetrafluoroethane (trifluoromethyl) -2-butene _{(CH 3 CF = C (CF} 3) 2); 1,1,1-trifluoro (trifluoromethyl) -2-butene _{((CF 3) 2 C =} CHCH 3); A 3,4,4,5,5,5- hexafluoro-2-pentene _{(CF 3 CF 2 CF = CHCH} 3); A 1,1,1,4,4,4- hexafluoro-2-methyl-2-butene _{(CF 3 C (CH 3)} = CHCF 3); 1-pentene _{(CH 2 = CHCF 2 CHFCF 3} ) a 3,3,4,5,5,5- hexafluoro; 4,4,4-trifluoro (trifluoromethyl) -3-butene _{(CH 2 = C (CF 3} ) CH 2 CF 3); 1-hexene with 1,1,2,3,3,4,4,5,5,6,6,6- dodeca-fluoro _{(CF 3 (CF 2) 3} CF = CF 2); 3-hexene _{(CF 3 CF 2 CF = CFCF} 2 CF 3) in 1,1,1,2,2,3,4,5,5,6,6,6- dodeca-fluoro; A 1,1,1,4,4,4- hexafluoro (trifluoromethyl) -2,3-bis-2-butene _{((CF 3) 2 C =} C (CF 3) 2); A 1,1,1,2,3,4,5,5,5- nonafluoro -4- (trifluoromethyl) -2-pentene _{((CF 3) 2 CFCF =} CFCF 3); A 1,1,1,4,4,5,5,5- octafluoro -2- (trifluoromethyl) -2-pentene _{((CF 3) 2 C =} CHC 2 F 5); A 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 (trifluoromethyl) -3,3-bis-1-butene _{(CH 2 = CHC (CF 3} ) 3); (CF ₃ ) ₂ C = C (CH ₃ ) (CF ₃ )) in the presence of 1,1,1,4,4,4-hexafluoro-2- (trifluoromethyl) ; (Trifluoromethyl) -4-2,3,3,5,5,5- hexafluoro-1-pentene _{(CH 2 = CFCF 2 CH (} CF 3) 2); 3-methyl-2-pentene as a 1,1,1,2,4,4,5,5,5- nonafluoro _{(CF 3 CF = C (CH} 3) CF 2 CF 3); (Trifluoromethyl) -4-1,1,1,5,5,5-hexafluoro-2-pentene _{(CF 3 CH = CHCH (CF} 3) 2); A 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- octafluoro-1-hexene _{(CH 2 = CHCF 2 CF 2} CF 2 CHF 2); A 1,1,1,4,4- pentafluoro -2- (trifluoromethyl) -2-pentene _{((CF 3) 2 C =} CHCF 2 CH 3); With 4,4,5,5,5- pentafluoropropane (trifluoromethyl) -2-pentene _{(CH 2 = C (CF 3} ) CH 2 C 2 F 5); 2-methyl-1-pentene as a 3,3,4,4,5,5,5- heptafluoropropane _{(CF 3 CF 2 CF 2 C} (CH 3) = CH 2); A 4,4,5,5,6,6,6- heptafluoro-2-hexene _{(CF 3 CF 2 CF 2 CH} = CHCH 3); A 4,4,5,5,6,6,6- heptafluoro-1-hexene _{(CH 2 = CHCH 2 CF 2} C 2 F 5); A 1,1,1,2,2,3,4- heptafluoro-3-hexene _{(CF 3 CF 2 CF = CFC} 2 H 5); (Trifluoromethyl) -4-4,5,5,5- tetrafluoro-1-pentene _{(CH 2 = CHCH 2 CF (} CF 3) 2); 4-methyl-2-pentene to 1,1,1,2,5,5,5- heptafluoropropane _{(CF 3 CF = CHCH (CF} 3) (CH 3)); As 1,1,1,3- tetrafluoroethane -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- tetra deca fluoro-2-heptene as a _{(CF 3 CF = CFCF 2 CF} 2 C 2 F 5) ; _{(5 CF 3 CF 2 CF =} CFCF 2 C 2 F) 1,1,1,2,2,3,4,5,5,6,6,7,7,7- tetra deca fluoro-3-heptene ; 1,1,1,3,4,4,5,5,6,6,7,7,7- a tree deca-fluoro-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- a tree deca-fluoro-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- tree to deca-fluoro-3-heptene _{(CF 3 CF 2 CH = CFCF} 2 C 2 F 5); 1,1,1,2,2,3,5,5,6,6,7,7,7- tree to deca-fluoro-3-heptene _{(CF 3 CF 2 CF = CHCF} 2 C 2 F 5); _{CF 2 = CFOCF 2 CF 3 (} PEVE) , and CF ₂ = fluoroolefin selected from the group consisting of CFOCF ₃ (PMVE)

&Lt; RTI ID = 0.0 &gt; and / or &lt; / RTI &gt;

The present invention also provides a composition comprising: (i) one or more fluoroolefin compounds; And (ii) at least one combustible refrigerant; The fluoroolefin,

(a) a fluoroolefin of the formula E or ZR ¹ CH = CHR ² , wherein R ¹ and R ² are independently a C ₁ to C ₆ perfluoroalkyl group;

(b) cyclic fluoroolefins of the formula cyclo- [CX = CY (CZW) _n -] _wherein X, Y, Z and W are independently H or F and n is an integer from 2 to 5; And

(c) -1- propene (CF ₃ CF = CHF) with 1,2,3,3,3- pentafluoropropane; 1-propene to 1,1,3,3,3-pentafluoropropane _{(CF 3 CH = CF 2)} ; 1,1,2,3,3-pentafluoro-1-propene (CHF ₂ CF = CF ₂ ); 2-butene to 1,1,1,2,3,4,4,4- octafluoro _{(CF 3 CF = CFCF 3)} ; A 1,1,2,3,3,4,4,4- octafluoro-1-butene _{(CF 3 CF 2 CF = CF} 2); 2-butene to 1,1,1,2,4,4,4- heptafluoropropane _{(CF 3 CF = CHCF 3)} ; 1,2,3,3,4,4,4-heptafluoro-1-butene (CHF = CFCF ₂ CF ₃ ); 2-butene (CHF ₂ CF = CFCF ₃₎ a 1,1,1,2,3,4,4- heptafluoropropane; As 1,3,3,3- tetrafluoroethane (trifluoromethyl) -2-1-propene _{((CF 3) 2 C =} CHF); 1,1,3,3,4,4,4- heptafluoro-1-butene as a _{(CF 2 = CHCF 2 CF 3} ); 1,1,2,3,4,4,4- heptafluoro-1-butene as a (CF ₂ = CFCHFCF _3); A 1,1,2,3,3,4,4- heptafluoro-1-butene _{(CF 2 = CFCF 2 CHF 2} ); A 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 as a _{(CHF = CHCF 2 CF 3)} ; 1-butene (CHF = CFCHFCF ₃₎ a 1,2,3,4,4,4- hexafluoro; 1,2,3,3,4,4-hexafluoro-1-butene (CHF = CFCF ₂ CHF ₂ ); 1,1,2,3,4,4- hexafluoro-2-butene as a _{(CHF 2 CF = CFCHF 2)} ; 1,1,1,2,3,4-hexafluoro- ₂ -butene (CH ₂ FCF = CFCF ₃ ); 2-butene (CHF ₂ CH = CFCF ₃₎ a 1,1,1,2,4,4- hexafluoro; 1,1,1,3,4,4- hexafluoro-2-butene as a _{(CF 3 CH = CFCHF 2)} ; 1-butene _{(CF 2 = CFCF 2 CH 2} F) to 1,1,2,3,3,4- hexafluoro; 1,1,2,3,4,4- hexafluoro-1-butene as a (CF ₂ = CFCHFCHF _2); 3,3,3-trifluoro (trifluoromethyl) -2-propene-1 _{(CH 2 = C (CF 3} ) 2); 1,1,1,2,3,4,4,5,5,5- to deca-fluoro-2-pentene _{(CF 3 CF = CFCF 2 CF} 3); 1,1,2,3,3,4,4,5,5,5- to deca-fluoro-1-pentene _{(CF 2 = CFCF 2 CF 2} CF 3); A 1,1,1,4,4,4- hexafluoro (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); A 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)} ; A 1,2,3,4,4,4- hexafluoro (trifluoromethyl) -3-butene _{(CHF = CFCF (CF 3)} 2); A 1,1,2,4,4,4- hexafluoro (trifluoromethyl) -3-butene-1 _{(CF 2 = CFCH (CF 3} ) 2); A 1,1,1,4,4,4- hexafluoro (trifluoromethyl) -2-butene _{(CF 3 CH = C (CF} 3) 2); A 1,1,3,4,4,4- hexafluoro (trifluoromethyl) -3-butene-1 _{(CF 2 = CHCF (CF 3} ) 2); A 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 ); With 3,3,4,4,4- pentafluoropropane (trifluoromethyl) -2-butene _{(CH 2 = C (CF 3} ) CF 2 CF 3); With 1,1,4,4,4- pentafluoropropane (trifluoromethyl) -3-butene-1 (CF = CHCH ₂ (CF _{3) 2);} With 1,3,4,4,4- pentafluoropropane (trifluoromethyl) -3-butene _{(CHF = CHCF (CF 3)} 2); With 1,1,4,4,4- pentafluoropropane (trifluoromethyl) -2-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 ); A 3,3,4,4,5,5,5- heptafluoro-1-pentene _{(CF 3 CF 2 CF 2 CH} = CH 2); A 2,3,3,4,4,5,5- heptafluoro-1-pentene _{(CH 2 = CFCF 2 CF 2} CHF 2); A 1,1,3,3,5,5,5- heptafluoro-1-butene _{(CF 2 = CHCF 2 CH 2} CF 3); 3-methyl-2-butene as a 1,1,1,2,4,4,4- heptafluoropropane _{(CF 3 CF = C (CF} 3) (CH 3)); As 2,4,4,4- tetrafluoroethane (trifluoromethyl) -3-butene _{(CH 2 = CFCH (CF 3} ) 2); As 1,4,4,4- tetrafluoroethane (trifluoromethyl) -3-butene _{(CHF = CHCH (CF 3)} 2); As 1,1,1,4- tetrafluoroethane (trifluoromethyl) -2-butene _{(CH 2 FCH = C (CF} 3) 2); As 1,1,1,3- tetrafluoroethane (trifluoromethyl) -2-butene _{(CH 3 CF = C (CF} 3) 2); 1-hexene with 1,1,2,3,3,4,4,5,5,6,6,6- dodeca-fluoro _{(CF 3 (CF 2) 3} CF = CF 2); 3-hexene _{(CF 3 CF 2 CF = CFCF} 2 CF 3) in 1,1,1,2,2,3,4,5,5,6,6,6- dodeca-fluoro; A 1,1,1,4,4,4- hexafluoro (trifluoromethyl) -2,3-bis-2-butene _{((CF 3) 2 C =} C (CF 3) 2); A 1,1,1,2,3,4,5,5,5- nonafluoro -4- (trifluoromethyl) -2-pentene _{((CF 3) 2 CFCF =} CFCF 3); A 1,1,1,4,4,5,5,5- octafluoro -2- (trifluoromethyl) -2-pentene _{((CF 3) 2 C =} CHC 2 F 5); A 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 (trifluoromethyl) -3,3-bis-1-butene _{(CH 2 = CHC (CF 3} ) 3); (CF ₃ ) ₂ C = C (CH ₃ ) (CF ₃ )) in the presence of 1,1,1,4,4,4-hexafluoro-2- (trifluoromethyl) ; (Trifluoromethyl) -4-2,3,3,5,5,5- hexafluoro-1-pentene _{(CH 2 = CFCF 2 CH (} CF 3) 2); 3-methyl-2-pentene as a 1,1,1,2,4,4,5,5,5- nonafluoro _{(CF 3 CF = C (CH} 3) CF 2 CF 3); (Trifluoromethyl) -4-1,1,1,5,5,5-hexafluoro-2-pentene _{(CF 3 CH = CHCH (CF} 3) 2); 1,1,1,2,3,4,4,5,5,6,6,7,7,7- tetra deca fluoro-2-heptene as a _{(CF 3 CF = CFCF 2 CF} 2 C 2 F 5) ; _{(5 CF 3 CF 2 CF =} CFCF 2 C 2 F) 1,1,1,2,2,3,4,5,5,6,6,7,7,7- tetra deca fluoro-3-heptene ; 1,1,1,3,4,4,5,5,6,6,7,7,7- a tree deca-fluoro-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- a tree deca-fluoro-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- tree to deca-fluoro-3-heptene _{(CF 3 CF 2 CH = CFCF} 2 C 2 F 5); And a 3-heptene _{(CF 3 CF 2 CF = CHCF} 2 C 2 F 5) in a tree 1,1,1,2,2,3,5,5,6,6,7,7,7- deca fluoro Fluoroolefins selected from the group consisting of

&Lt; / RTI &gt;

The present invention also relates to

(i) a fluoroolefin of the formula E or ZR ¹ CH = CHR ² , wherein R ¹ and R ² are independently a C ₁ to C ₆ perfluoroalkyl group;

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

(iii) -1- propene (CF ₃ CF = CHF) with 1,2,3,3,3- pentafluoropropane; 1-propene to 1,1,3,3,3-pentafluoropropane _{(CF 3 CH = CF 2)} ; 1,1,2,3,3-pentafluoro-1-propene (CHF ₂ CF = CF ₂ ); 1,2,3,3-tetrafluoro-1-propene (CHF ₂ CF = CHF); 2,3,3,3- tetrafluoro-1-propene with _{(CF 3 CF = CH 2)} ; 1,3,3,3- tetrafluoro-1-propene with (CF ₃ CH = CHF); 1,1,2,3-tetrafluoro-1-propene (CH ₂ FCF = CF ₂ ); 1,1,3,3-tetrafluoro-1-propene (CHF ₂ CH = CF ₂ ); 2,3,3-Trifluoro-1-propene (CHF ₂ CF = CH ₂ ); 1-propene, 3,3,3-trifluoromethyl _{(CF 3 CH = CH 2)} ; In 1,1,2-trifluoro-1-propene _{(CH 3 CF = CF 2)} ; 1,1,3-trifluoro-1-propene (CH ₂ FCH = CF ₂ ); 1,2,3-trifluoro-1-propene (CH ₂ FCF = CHF); 1,3,3-trifluoro-1-propene (CHF ₂ CH = CHF); 2-butene to 1,1,1,2,3,4,4,4- octafluoro _{(CF 3 CF = CFCF 3)} ; A 1,1,2,3,3,4,4,4- octafluoro-1-butene _{(CF 3 CF 2 CF = CF} 2); 2-butene to 1,1,1,2,4,4,4- heptafluoropropane _{(CF 3 CF = CHCF 3)} ; 1,2,3,3,4,4,4-heptafluoro-1-butene (CHF = CFCF ₂ CF ₃ ); 2-butene (CHF ₂ CF = CFCF ₃₎ a 1,1,1,2,3,4,4- heptafluoropropane; As 1,3,3,3- tetrafluoroethane (trifluoromethyl) -2-1-propene _{((CF 3) 2 C =} CHF); 1,1,3,3,4,4,4- heptafluoro-1-butene as a _{(CF 2 = CHCF 2 CF 3} ); 1,1,2,3,4,4,4- heptafluoro-1-butene as a (CF ₂ = CFCHFCF _3); A 1,1,2,3,3,4,4- heptafluoro-1-butene _{(CF 2 = CFCF 2 CHF 2} ); A 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 as a _{(CHF = CHCF 2 CF 3)} ; 1-butene (CHF = CFCHFCF ₃₎ a 1,2,3,4,4,4- hexafluoro; 1,2,3,3,4,4-hexafluoro-1-butene (CHF = CFCF ₂ CHF ₂ ); 1,1,2,3,4,4- hexafluoro-2-butene as a _{(CHF 2 CF = CFCHF 2)} ; 1,1,1,2,3,4-hexafluoro- ₂ -butene (CH ₂ FCF = CFCF ₃ ); 2-butene (CHF ₂ CH = CFCF ₃₎ a 1,1,1,2,4,4- hexafluoro; 1,1,1,3,4,4- hexafluoro-2-butene as a _{(CF 3 CH = CFCHF 2)} ; 1-butene _{(CF 2 = CFCF 2 CH 2} F) to 1,1,2,3,3,4- hexafluoro; 1,1,2,3,4,4- hexafluoro-1-butene as a (CF ₂ = CFCHFCHF _2); 3,3,3-trifluoro (trifluoromethyl) -2-propene-1 _{(CH 2 = C (CF 3} ) 2); A 1,1,1,2,4- pentafluoro-2-butene _{(CH 2 FCH = CFCF 3)} ; 1,1,1,3,4- pentafluoro-2-butene as a _{(CF 3 CH = CFCH 2 F} ); 3,3,4,4,4- pentafluoro-1-butene with _{(CF 3 CF 2 CH = CH} 2); 1,1,1,4,4- pentafluorophenyl-2-butene _{(CHF 2 CH = CHCF 3)} ; 2-butene (CH ₃ CF = CFCF ₃₎ with 1,1,1,2,3- pentafluoropropane; 2,3,3,4,4- pentafluorophenyl-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- pentafluorophenyl-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 pentafluoroethyl-2-methyl-1-propene _{(CF 2 = C (CF 3} ) (CH 3)); 2- (difluoro-methyl) -3,3,3-trifluoro-1-propene _{(CH 2 = C (CHF 2} ) (CF 3)); 1-butene (CH ₂ = CFCHFCF ₃₎ with 2,3,4,4,4- pentafluoropropane; 1,2,4,4,4- pentafluorophenyl-1-butene _{(CHF = CFCH 2 CF 3)} ; 1,3,4,4,4- pentafluorophenyl-1-butene (CHF = CHCHFCF _3); 1,3,3,4,4- pentafluoro-1-butene as a _{(CHF = CHCF 2 CHF 2)} ; 1,2,3,4,4- pentafluorophenyl-1-butene (CHF = CFCHFCHF _2); 1-butene as 3,3,4,4- tetrafluoroethane _{(CH 2 = CHCF 2 CHF 2} ); 1,1-di (difluoromethyl) -2-fluoro-1-propene _{(CF 2 = C (CHF 2} ) (CH 3)); 2-methyl-1-propene _{(CHF = C (CF 3)} (CH 3)) to 1,3,3,3- tetrafluoroethane; 2-difluoro-methyl-3,3-difluoro-1-propene _{(CH 2 = C (CHF 2} ) 2); 2-butene-1,1,1,2-tetrafluoroethane _{(CF 3 CF = CHCH 3)} ; 2-butene as 1,1,1,3- tetrafluoroethane (CF ₃ CH = CHCF _3); 1,1,1,2,3,4,4,5,5,5- to deca-fluoro-2-pentene _{(CF 3 CF = CFCF 2 CF} 3); 1,1,2,3,3,4,4,5,5,5- to deca-fluoro-1-pentene _{(CF 2 = CFCF 2 CF 2} CF 3); A 1,1,1,4,4,4- hexafluoro (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); A 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)} ; A 1,2,3,4,4,4- hexafluoro (trifluoromethyl) -3-butene _{(CHF = CFCF (CF 3)} 2); A 1,1,2,4,4,4- hexafluoro (trifluoromethyl) -3-butene-1 _{(CF 2 = CFCH (CF 3} ) 2); A 1,1,1,4,4,4- hexafluoro (trifluoromethyl) -2-butene _{(CF 3 CH = C (CF} 3) 2); A 1,1,3,4,4,4- hexafluoro (trifluoromethyl) -3-butene-1 _{(CF 2 = CHCF (CF 3} ) 2); A 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 ); With 3,3,4,4,4- pentafluoropropane (trifluoromethyl) -2-butene _{(CH 2 = C (CF 3} ) CF 2 CF 3); With 1,1,4,4,4- pentafluoropropane (trifluoromethyl) -3-butene-1 (CF = CHCH ₂ (CF _{3) 2);} With 1,3,4,4,4- pentafluoropropane (trifluoromethyl) -3-butene _{(CHF = CHCF (CF 3)} 2); With 1,1,4,4,4- pentafluoropropane (trifluoromethyl) -2-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 ); A 3,3,4,4,5,5,5- heptafluoro-1-pentene _{(CF 3 CF 2 CF 2 CH} = CH 2); A 2,3,3,4,4,5,5- heptafluoro-1-pentene _{(CH 2 = CFCF 2 CF 2} CHF 2); A 1,1,3,3,5,5,5- heptafluoro-1-butene _{(CF 2 = CHCF 2 CH 2} CF 3); 3-methyl-2-butene as a 1,1,1,2,4,4,4- heptafluoropropane _{(CF 3 CF = C (CF} 3) (CH 3)); As 2,4,4,4- tetrafluoroethane (trifluoromethyl) -3-butene _{(CH 2 = CFCH (CF 3} ) 2); As 1,4,4,4- tetrafluoroethane (trifluoromethyl) -3-butene _{(CHF = CHCH (CF 3)} 2); As 1,1,1,4- tetrafluoroethane (trifluoromethyl) -2-butene _{(CH 2 FCH = C (CF} 3) 2); As 1,1,1,3- tetrafluoroethane (trifluoromethyl) -2-butene _{(CH 3 CF = C (CF} 3) 2); 1,1,1-trifluoro (trifluoromethyl) -2-butene _{((CF 3) 2 C =} CHCH 3); A 3,4,4,5,5,5- hexafluoro-2-pentene _{(CF 3 CF 2 CF = CHCH} 3); A 1,1,1,4,4,4- hexafluoro-2-methyl-2-butene _{(CF 3 C (CH 3)} = CHCF 3); 1-pentene _{(CH 2 = CHCF 2 CHFCF 3} ) a 3,3,4,5,5,5- hexafluoro; 3- (trifluoro methyl) - 4,4,4-trifluoro-1-butene _{(CH 2 = C (CF 3} ) CH 2 CF 3); 1-hexene with 1,1,2,3,3,4,4,5,5,6,6,6- dodeca-fluoro _{(CF 3 (CF 2) 3} CF = CF 2); 3-hexene _{(CF 3 CF 2 CF = CFCF} 2 CF 3) in 1,1,1,2,2,3,4,5,5,6,6,6- dodeca-fluoro; A 1,1,1,4,4,4- hexafluoro (trifluoromethyl) -2,3-bis-2-butene _{((CF 3) 2 C =} C (CF 3) 2); A 1,1,1,2,3,4,5,5,5- nonafluoro -4- (trifluoromethyl) -2-pentene _{((CF 3) 2 CFCF =} CFCF 3); A 1,1,1,4,4,5,5,5- octafluoro -2- (trifluoromethyl) -2-pentene _{((CF 3) 2 C =} CHC 2 F 5); A 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 (trifluoromethyl) -3,3-bis-1-butene _{(CH 2 = CHC (CF 3} ) 3); (CF ₃ ) ₂ C = C (CH ₃ ) (CF ₃ )). ; (Trifluoromethyl) -4-2,3,3,5,5,5- hexafluoro-1-pentene _{(CH 2 = CFCF 2 CH (} CF 3) 2); 3-methyl-2-pentene as a 1,1,1,2,4,4,5,5,5- nonafluoro _{(CF 3 CF = C (CH} 3) CF 2 CF 3); (Trifluoromethyl) -4-1,1,1,5,5,5-hexafluoro-2-pentene _{(CF 3 CH = CHCH (CF} 3) 2); A 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- octafluoro-1-hexene _{(CH 2 = CHCF 2 CF 2} CF 2 CHF 2); A 1,1,1,4,4- pentafluoro -2- (trifluoromethyl) -2-pentene _{((CF 3) 2 C =} CHCF 2 CH 3); With 4,4,5,5,5- pentafluoropropane (trifluoromethyl) -2-pentene _{(CH 2 = C (CF 3} ) CH 2 C 2 F 5); 2-methyl-1-pentene as a 3,3,4,4,5,5,5- heptafluoropropane _{(CF 3 CF 2 CF 2 C} (CH 3) = CH 2); A 4,4,5,5,6,6,6- heptafluoro-2-hexene _{(CF 3 CF 2 CF 2 CH} = CHCH 3); A 4,4,5,5,6,6,6- heptafluoro-1-hexene _{(CH 2 = CHCH 2 CF 2} C 2 F 5); A 1,1,1,2,2,3,4- heptafluoro-3-hexene _{(CF 3 CF 2 CF = CFC} 2 H 5); Methyl-1-pentene-4-trifluoro-4,5,5,5- tetrafluoroethane _{(CH 2 = CHCH 2 CF (} CF 3) 2); 4-methyl-2-pentene to 1,1,1,2,5,5,5- heptafluoropropane _{(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- tetra deca fluoro-2-heptene as a _{(CF 3 CF = CFCF 2 CF} 2 C 2 F 5) ; _{(5 CF 3 CF 2 CF =} CFCF 2 C 2 F) 1,1,1,2,2,3,4,5,5,6,6,7,7,7- tetra deca fluoro-3-heptene ; 1,1,1,3,4,4,5,5,6,6,7,7,7- a tree deca-fluoro-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- a tree deca-fluoro-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- tree to deca-fluoro-3-heptene _{(CF 3 CF 2 CH = CFCF} 2 C 2 F 5); 1,1,1,2,2,3,5,5,6,6,7,7,7- tree to deca-fluoro-3-heptene _{(CF 3 CF 2 CF = CHCF} 2 C 2 F 5); Fluoroolefins selected from the group consisting of CF ₂ = CFOCF ₂ CF ₃ (PEVE) and CF ₂ = CFOCF ₃ (PMVE)

At least one fluoroolefin selected from the group consisting of: (a) a centrifugal compressor; (b) a multistage centrifugal compressor, or (c) a single slab / single pass heat exchanger, wherein the composition is used in the apparatus to provide heating or cooling , And a method of using the composition in the device.

The present invention relates to a composition comprising at least one fluoroolefin. By fluoroolefin is meant any compound containing carbon, fluorine and optionally hydrogen or oxygen, and also containing one or more double bonds. These fluoroolefins may be linear, branched or cyclic.

These compositions have a variety of utility in the working fluid, which can be used in some instances as foam forming agents, foaming agents, fire extinguishing agents, heat transfer media (e.g., refrigeration systems, refrigerators, air conditioning systems, Heat transfer fluid and refrigerant for heat transfer).

A heat transfer fluid (also referred to herein as a heat transfer composition or heat transfer fluid composition) is a working fluid used to transfer heat from a heat source to a heat sink.

A refrigerant is a compound or mixture of compounds that functions as a heat transfer fluid in a cycle, where the fluid moves from liquid to gas, and vice versa.

The present invention provides a fluoroolefin having the formula E or ZR ¹ CH = CHR ² (wherein R ¹ and R ² are independently C ₁ to C ₆ perfluoroalkyl groups). Examples of R ¹ and R _{^2, CF 3, C 2 F 5} , CF 2 CF 2 CF 3, CF (CF 3) 2, CF 2 CF 2 CF 2 CF 3, CF (CF 3) CF 2 CF 3, _{CF 2 CF (CF 3) 2} , C (CF 3) 3, CF 2 CF 2 CF 2 CF 2 CF 3, CF 2 CF 2 CF (CF 3) 2, C (CF 3) 2 C 2 F 5, CF _{But are not limited to, 2} CF ₂ CF ₂ CF ₂ CF ₂ CF ₃ , CF (CF ₃ ) CF ₂ CF ₂ C ₂ F ₅ , and C (CF ₃ ) ₂ CF ₂ C ₂ F ₅ . In one embodiment, the fluoroolefin of formula I has at least about 3 carbon atoms in the molecule. In another embodiment, the fluoroolefin of formula (I) has about 4 or more carbon atoms in the molecule. In another embodiment, the fluoroolefin of formula (I) has at least about 5 carbon atoms in the molecule. Non-limiting examples of compounds of formula I are shown in Table 1 below.

Compounds of formula I can be prepared by contacting perfluoroalkyl iodides of formula R ¹ I with perfluoroalkyl trihydroolefins of the formula R ² CH = CH ₂ to give the trihydroiodopurine of formula R ¹ CH ₂ CHIR ² Lt; RTI ID = 0.0 &gt; R &lt; / RTI &gt; The trihydroiodoperfluoroalkane may then be dehydrogenated to form R ¹ CH = CHR ² . Alternatively, the olefin R ¹ CH = CHR ^2, the formula R ¹ CHICH ₂ R formed by alkyltrimethylenediamine hydrocarbyl olefin and reaction with an alkyl iodide, perfluoroalkyl of formula R ² I perfluoroalkyl of formula R ¹ CH = CH ₂ ² &lt; / RTI &gt; of trihydroiodoperfluoroalkane.

The contacting of the perfluoroalkyl iodide with the perfluoroalkyl trihydro olefin may be performed batchwise by combining the reactants in a suitable reaction vessel capable of working under the autogenous pressure of the reactants and products at the reaction temperature. Suitable reaction vessels are made especially from austenitic stainless steels, and from known high nickel alloys such as Monel nickel-copper alloys, Hastelloy nickel based alloys, Includes Inconel® nickel-chromium alloy.

Alternatively, the reaction may be carried out in a semi-batch mode in which the perfluoroalkyl trihydro-olefin reactant is added to the perfluoroalkyl iodide reactant by a suitable addition device such as a pump at the reaction temperature.

The ratio of perfluoroalkyl iodide to perfluoroalkyl trihydro olefin should be from about 1: 1 to about 4: 1, preferably from about 1.5: 1 to 2.5: 1. See Jeanneaux, et. al., Journal of Fluorine Chemistry, Vol. 4, pages 261-270 (1974)], ratios below 1.5: 1 tend to produce large amounts of 2: 1 adducts.

The preferred temperature for contacting the perfluoroalkyl iodide with the perfluoroalkyl trihydro olefin is preferably from about 150 ° C to about 300 ° C, preferably from about 170 ° C to about 250 ° C, Lt; 0 &gt; C to about 230 &lt; 0 &gt; C. Suitable contact times for the reaction of perfluoroalkyl iodide with perfluoroalkyl trihydroolefins are from about 0.5 to 18 hours, preferably from about 4 to about 12 hours.

The trihydroiodoperfluoroalkanes prepared by the reaction of perfluoroalkyl iodides with perfluoroalkyl trihydro olefins can be used directly in the step of removing hydrogen iodide or, preferably, Can be recovered and purified.

The iodide removal step is carried out by contacting the trihydroiodoperfluoroalkane with a basic material. Suitable basic materials include, but are not limited to, alkali metal hydroxides such as sodium hydroxide or potassium hydroxide, alkali metal oxides such as sodium oxide, alkaline earth metal hydroxides such as calcium hydroxide, , Calcium oxide), alkali metal alkoxides (e.g., sodium methoxide or sodium ethoxide), aqueous ammonia, sodium amide, or soda lime. Preferred basic materials are sodium hydroxide and potassium hydroxide. Said contacting of the basic material with the trihydroiodoperfluoroalkane is preferably carried out in the liquid phase in the presence of a solvent capable of dissolving at least a portion of both reactants. Suitable solvents for the hydrogen iodide removal step include one or more polar organic solvents such as alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol and tertiary butanol, , Acetonitrile, propionitrile, butyronitrile, benzonitrile, or adiponitrile), dimethylsulfoxide, N, N-dimethylformamide, N, N-dimethylacetamide, or sulfolane. The choice of solvent may depend on the product boiling point and the ease of separation of the minor solvent from the product during purification. Typically, ethanol or isopropanol is an excellent solvent for the reaction.

Typically, the iodide removal reaction can be carried out by adding one of the reactants (basic material or trihydroiodoperfluoroalkane) to the other reactants in a suitable reaction vessel. The reaction can be made from glass, ceramic or metal and is preferably stirred by an impeller or stirring mechanism.

Suitable temperatures for the hydrogen iodide removal reaction are from about 10 캜 to about 100 캜, preferably from about 20 캜 to about 70 캜. The iodide removal reaction can be carried out at ambient pressure, or at reduced or elevated pressure. It is important to remove the hydrogen iodide from the reaction vessel by distillation of the compound of formula I as it forms.

Alternatively, the iodide removal reaction may be carried out in the presence of a phase transfer catalyst in one or more organic solvents having lower polarity such as alkanes (e.g., hexane, heptane, or octane), aromatic hydrocarbons (e.g., toluene) , Halogenated hydrocarbons (e.g., methylene chloride, chloroform, carbon tetrachloride, or perchlorethylene), or ethers (e.g., diethyl ether, methyl tert-butyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, di For example, by contacting an aqueous solution of the basic substance with a solution of a trihydroiodoperfluoroalkane in a solvent such as tetrahydrofuran, dioxane, dimethoxyethane, dimethoxyethane, diglyme, or tetraglyme. Suitable phase transfer catalysts include, but are not limited to, quaternary ammonium halides (e.g., tetrabutylammonium bromide, tetrabutylammonium hydrosulfate, triethylbenzylammonium chloride, dodecyltrimethylammonium chloride and tricaprylylmethylammonium chloride) (E. G., 18-crown-6 and 15-crown &lt; / RTI &gt; compounds) known in the art as crown ethers (e. G., Triphenylmethane halides such as triphenylmethylphosphonium bromide and tetraphenylphosphonium chloride) -5).

Alternatively, the iodide removal reaction can be carried out in the absence of a solvent by adding a solid or liquid basic material to the trihydroiodoperfluoroalkane.

Suitable reaction times for the hydrogen iodide removal reaction are from about 15 minutes to about 6 hours or more, depending on the solubility of the reactants. Typically, the iodide removal reaction is rapid and requires about 30 minutes to about 3 hours to complete. The compounds of formula I may be recovered from the iodine removal reaction mixture by phase separation after addition of water, by distillation or by a combination thereof.

In another embodiment of the present invention, the fluoroolefin is selected from the group consisting of cyclic fluoroolefins (cyclo- [CX = CY (CZW) _n -] _wherein X, Y, Z and W are independently H And F, where n is an integer from 2 to 5. Representative cyclic fluoroolefins of Formula II are shown in Table 2 below.

In another embodiment, the fluoroolefin may comprise a compound as set forth in Table 3 below.

The compounds listed in Table 2 and Table 3 are either commercially available or can be prepared by methods known in the art or as described herein.

1,1,1,4,4-pentafluoro-2-butene is obtained by removal of 1,1,1,2,4,4-hexafluorobutane (CHF 3) by hydrogen fluoride removal on solid KOH in the vapor phase at room temperature ₂ CH ₂ CHFCF ₃ ). The synthesis of 1,1,1,2,4,4-hexafluorobutane is described in US 6,066,768, which is incorporated herein by reference.

1,1,1,4,4,4-Hexafluoro-2-butene is reacted with KOH using a phase transfer catalyst at about 60 &lt; 0 &gt; C to give 1,1,1,4,4,4-hexafluoro -2-iodobutane (CF ₃ CHICH ₂ CF ₃ ). A 1,1,1,4,4,4- hexafluoro-2-iodo Synthesis of butane, perfluoro at about 200 ℃ for about 8 hours under autogenous pressure methyl iodide (CF ₃ I) and 3 , And 3,3-trifluoropropene (CF ₃ CH = CH ₂ ).

3, 4, 5, 5, 5, 5-hexafluoro-2-pentene can be prepared by reacting 1,1,1,2,2,3,3-hepta It can be prepared by removal of the hydrogen fluoride-pentane _{(CF 3 CF 2 CF 2 CH} 2 CH 3) fluoro. A 1,1,1,2,2,3,3- heptafluoro-pentane is, 1-pentene _{(CF 3 CF 2 CF 2 CH} = as 3,3,4,4,5,5,5- heptafluoro CH ₂ ). &Lt; / RTI &gt;

1,1,1,2,3,4-Hexafluoro-2-butene was prepared by reacting 1,1,1,2,3,3,4-heptafluorobutane (CH ₂ FCF ₂ CHFCF ₃ ). &Lt; / RTI &gt;

A 1,1,1,2,4,4- hexafluoro-2-butene, butane to 1,1,1,2,2,4,4- heptafluoropropane with solid KOH (CHF ₂ CH ₂ CF ₂ CF ₃ ) by hydrogen fluoride removal.

A 1,1,1,3,4,4- hexafluoro-2-butene, butane to 1,1,1,3,3,4,4- heptafluoropropane with solid KOH (CF ₃ CH ₂ CF ₂ CHF ₂ ) by hydrogen fluoride removal.

1,1,1,2,4-pentafluoro-2-butene was prepared by reacting 1,1,1,2,2,3-hexafluorobutane (CH ₂ FCH ₂ CF ₂ CF ₃ ) with solid KOH And hydrogen fluoride removal.

A 1,1,1,3,4- pentafluoro-2-butene, 1,1,1,3,3,4- hexafluoro-butane as with solid _{KOH (CF 3 CH 2 CF 2} CH 2 F) By hydrogen fluoride removal.

1,1,1,3-tetrafluoro-2-butene is prepared by reacting 1,1,1,3,3-pentafluorobutane (CF ₃ CH ₂ CF ₂ CH ₃ ) with aqueous KOH at 120 ° C. Can be manufactured.

1,1,1,4,4,5,5,5-octafluoro-2-pentene can be prepared by reacting (CF ₃ CHICH ₂ CF ₂ CF ₃ ) with KOH using a phase transfer catalyst at about 60 ° C. Can be manufactured. Synthesis of 4-iodo-pentane in -1,1,1,2,2,5,5,5- octafluoro is, at about 200 ℃ for about 8 hours under autogenous pressure a perfluoroalkyl ethyl iodide (CF ₃ CF ₂ I) with 3,3,3-trifluoropropene.

1,1,1,2,2,5,5,6,6,6-Decafluoro-3-hexene is reacted with KOH using a phase transfer catalyst at about 60 &lt; 0 &gt; can be 2,5,5,6,6,6- to deca-fluoro-3-iodo be prepared from hexane _{(CF 3 CF 2 CHICH 2 CF} 2 CF 3). The synthesis of 1,1,1,2,2,5,5,6,6,6-decafluoro-3-iodohexane is carried out under atmospheric pressure at about 200 &lt; 0 &gt; C for about 8 hours with perfluoroethyl iodide (CF ₃ CF ₂ I) with 3,3,4,4,4-pentafluoro-1-butene (CF ₃ CF ₂ CH = CH ₂ ).

1,1,1,4,5,5,5-heptafluoro-4- (trifluoromethyl) -2-pentene was prepared by reacting 1,1,1,2,5,5,5 - (trifluoromethyl) hepta-fluoro-4-iodo-2-pentanol can be prepared by the removal of hydrogen fluoride _{(CF 3 CHICH 2 CF (CF} 3) 2). _{CF 3 CHICH 2 CF (CF 3} ) 2 is prepared at a high temperature such as about 200 ℃ (CF _{3) 2} from the reaction of CFI and CF ₃ CH = CH _2.

1,1,1,4,4,5,5,6,6,6-decafluoro-2-hexene is 1,1,1,4,4,4-hexafluoro-2-butene (CF ₃ CH = CHCF ₃ ) with tetrafluoroethylene (CF ₂ = CF ₂ ) and antimony pentafluoride (SbF ₅ ).

2,3,3,4,4-pentafluoro-l-butene is prepared by removal of hydrogen fluoride of 1,1,2,2,3,3-hexafluorobutane on alumina fluoride at elevated temperature .

2,3,3,4,4,4,5,5,5-Octafluoro-1-pentene can be prepared by reacting 2,2,3,3,4,4,5,5,5-nonafluoro Can be prepared by hydrogen fluoride removal of pentane.

1,2,3,3,4,4,5,5-Octafluoro-1-pentene was prepared by reacting 2,2,3,3,4,4,5,5,5- Can be produced by hydrogen fluoride removal of nonafluoropentane.

The compositions of the present invention may comprise a single compound of Formula I, Formula II or Table 3, or may comprise a combination of the above compounds. In addition, most of the compounds of formulas I, II and 3 may exist as different coordination isomers or stereoisomers. The present invention is intended to include all single coordination isomers, single stereoisomers, or any combination thereof. For example, 1,3,3,3-tetrafluoropropene (HFC-1234ze) has the meaning of representing E-isomer, Z-isomer, or any combination or mixture of these two isomers in any proportion . Another example is F12E, which refers to any combination or mixture of E-isomers, Z-isomers, or any of these two isomers.

The composition of the present invention has low or zero ozone depletion potential and low global warming potential (GWP). Mixtures of the fluoroolefins of the present invention or of the fluoroolefins of the present invention with other refrigerants have a lower global warming index than many of the hydrofluorocarbon refrigerants currently used. One aspect of the present invention is to provide a refrigerant having a global warming index of less than 1000, less than 500, less than 150, less than 100, or less than 50. [ Another aspect of the invention is to reduce the final GWP of the mixture by adding the fluoroolefin to the refrigerant mixture.

The composition of the present invention which is a combination or mixture can be prepared by any convenient method for combining the desired amounts of the individual components. A preferred method is to weigh the amount of the desired component and then combine the components in a suitable container. If desired, stirring may be used.

Alternative means of making the composition of the present invention include the steps of (i) recovering at least one component of a volume of refrigerant composition from at least one refrigerant vessel, (ii) recovering at least one of the impurities , And (iii) optionally, combining all or a portion of the recovered component volume with one or more additional refrigerant compositions or components.

The refrigerant vessel may be any vessel in which the refrigerant blend composition used for the refrigeration unit, air conditioning unit or heating pump unit is stored. The refrigerant vessel may be a refrigerating apparatus, an air conditioning apparatus or a heating pump apparatus in which a refrigerant blend is used. The refrigerant vessel may also be a storage vessel for collecting the recovered refrigerant blend components, including, but not limited to, pressurized gas cylinders.

Residual refrigerant means any amount of refrigerant blend or refrigerant blend component that can be removed from the refrigerant vessel by any known means for transferring the refrigerant blend or refrigerant blend component.

The impurities may be any component present in the refrigerant blend or refrigerant blend component due to use in a refrigeration unit, air conditioning unit or heating pump unit. Such impurities may include, but are not limited to, refrigerant lubricants (as described herein above), refrigerants, fine particles such as elastomers or metals that may come from air conditioning or heating pump devices, and any other materials that may adversely affect the performance of the refrigerant blend composition But are not limited to, other contaminants.

Such impurities can be removed sufficiently to enable the reuse of the refrigerant blend or refrigerant blend components without adversely affecting the equipment or performance of the refrigerant blend or refrigerant blend components.

It may be necessary to provide additional refrigerant blend or refrigerant blend components to the residual refrigerant blend or refrigerant blend component to produce a composition that meets the specificities required for a given product. For example, if the refrigerant blend has three components in a specific weight ratio range, it may be necessary to add a predetermined amount of one or more components to restore the composition to within a certain range.

The composition of the present invention, useful as a refrigerant or heat transfer fluid,

(i) a compound of the formula E or ZR ¹ CH = CHR ² , wherein R ¹ and R ² are independently C ₁ to C ₆ perfluoroalkyl groups, wherein the total number of carbons in the compound is at least 5, Olefins;

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

(iii) -1- propene (CF ₃ CF = CHF) with 1,2,3,3,3- pentafluoropropane; 1-propene to 1,1,3,3,3-pentafluoropropane _{(CF 3 CH = CF 2)} ; 1,1,2,3,3-pentafluoro-1-propene (CHF ₂ CF = CF ₂ ); 1,2,3,3-tetrafluoro-1-propene (CHF ₂ CF = CHF); 2,3,3,3- tetrafluoro-1-propene with _{(CF 3 CF = CH 2)} ; 1,1,2,3-tetrafluoro-1-propene (CH ₂ FCF = CF ₂ ); 1,1,3,3-tetrafluoro-1-propene (CHF ₂ CH = CF ₂ ); 2,3,3-Trifluoro-1-propene (CHF ₂ CF = CH ₂ ); 1-propene, 3,3,3-trifluoromethyl _{(CF 3 CH = CH 2)} ; In 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); 2-butene to 1,1,1,2,3,4,4,4- octafluoro _{(CF 3 CF = CFCF 3)} ; A 1,1,2,3,3,4,4,4- octafluoro-1-butene _{(CF 3 CF 2 CF = CF} 2); 2-butene to 1,1,1,2,4,4,4- heptafluoropropane _{(CF 3 CF = CHCF 3)} ; 1,2,3,3,4,4,4-heptafluoro-1-butene (CHF = CFCF ₂ CF ₃ ); 2-butene (CHF ₂ CF = CFCF ₃₎ a 1,1,1,2,3,4,4- heptafluoropropane; As 1,3,3,3- tetrafluoroethane (trifluoromethyl) -2-1-propene _{((CF 3) 2 C =} CHF); 1,1,3,3,4,4,4- heptafluoro-1-butene as a _{(CF 2 = CHCF 2 CF 3} ); 1,1,2,3,4,4,4- heptafluoro-1-butene as a (CF ₂ = CFCHFCF _3); A 1,1,2,3,3,4,4- heptafluoro-1-butene _{(CF 2 = CFCF 2 CHF 2} ); A 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 as a _{(CHF = CHCF 2 CF 3)} ; 1-butene (CHF = CFCHFCF ₃₎ a 1,2,3,4,4,4- hexafluoro; 1,2,3,3,4,4-hexafluoro-1-butene (CHF = CFCF ₂ CHF ₂ ); 1,1,2,3,4,4- hexafluoro-2-butene as a _{(CHF 2 CF = CFCHF 2)} ; 1,1,1,2,3,4-hexafluoro- ₂ -butene (CH ₂ FCF = CFCF ₃ ); 2-butene (CHF ₂ CH = CFCF ₃₎ a 1,1,1,2,4,4- hexafluoro; 1,1,1,3,4,4- hexafluoro-2-butene as a _{(CF 3 CH = CFCHF 2)} ; 1-butene _{(CF 2 = CFCF 2 CH 2} F) to 1,1,2,3,3,4- hexafluoro; 1,1,2,3,4,4- hexafluoro-1-butene as a (CF ₂ = CFCHFCHF _2); 3,3,3-trifluoro (trifluoromethyl) -2-propene-1 _{(CH 2 = C (CF 3} ) 2); A 1,1,1,2,4- pentafluoro-2-butene _{(CH 2 FCH = CFCF 3)} ; 1,1,1,3,4- pentafluoro-2-butene as a _{(CF 3 CH = CFCH 2 F} ); 3,3,4,4,4- pentafluoro-1-butene with _{(CF 3 CF 2 CH = CH} 2); 1,1,1,4,4- pentafluorophenyl-2-butene _{(CHF 2 CH = CHCF 3)} ; 2-butene (CH ₃ CF = CFCF ₃₎ with 1,1,1,2,3- pentafluoropropane; 2,3,3,4,4- pentafluorophenyl-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- pentafluorophenyl-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 pentafluoroethyl-2-methyl-1-propene _{(CF 2 = C (CF 3} ) (CH 3)); 2- (difluoro-methyl) -3,3,3-trifluoro-1-propene _{(CH 2 = C (CHF 2} ) (CF 3)); 1-butene (CH ₂ = CFCHFCF ₃₎ with 2,3,4,4,4- pentafluoropropane; 1,2,4,4,4- pentafluorophenyl-1-butene _{(CHF = CFCH 2 CF 3)} ; 1,3,4,4,4- pentafluorophenyl-1-butene (CHF = CHCHFCF _3); 1,3,3,4,4- pentafluoro-1-butene as a _{(CHF = CHCF 2 CHF 2)} ; 1,2,3,4,4- pentafluorophenyl-1-butene (CHF = CFCHFCHF _2); 1-butene as 3,3,4,4- tetrafluoroethane _{(CH 2 = CHCF 2 CHF 2} ); 1,1-di (difluoromethyl) -2-fluoro-1-propene _{(CF 2 = C (CHF 2} ) (CH 3)); 2-methyl-1-propene _{(CHF = C (CF 3)} (CH 3)) to 1,3,3,3- tetrafluoroethane; 3,3-di (difluoromethyl) -2-fluoro-1-propene _{(CH 2 = C (CHF 2} ) 2); 2-butene-1,1,1,2-tetrafluoroethane _{(CF 3 CF = CHCH 3)} ; 2-butene as 1,1,1,3- tetrafluoroethane (CF ₃ CH = CHCF _3); 1,1,1,2,3,4,4,5,5,5- to deca-fluoro-2-pentene _{(CF 3 CF = CFCF 2 CF} 3); 1,1,2,3,3,4,4,5,5,5- to deca-fluoro-1-pentene _{(CF 2 = CFCF 2 CF 2} CF 3); A 1,1,1,4,4,4- hexafluoro (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); A 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)} ; A 1,2,3,4,4,4- hexafluoro (trifluoromethyl) -3-butene _{(CHF = CFCF (CF 3)} 2); A 1,1,2,4,4,4- hexafluoro (trifluoromethyl) -3-butene-1 _{(CF 2 = CFCH (CF 3} ) 2); A 1,1,1,4,4,4- hexafluoro (trifluoromethyl) -2-butene _{(CF 3 CH = C (CF} 3) 2); A 1,1,3,4,4,4- hexafluoro (trifluoromethyl) -3-butene-1 _{(CF 2 = CHCF (CF 3} ) 2); A 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 ); With 3,3,4,4,4- pentafluoropropane (trifluoromethyl) -2-butene _{(CH 2 = C (CF 3} ) CF 2 CF 3); With 1,1,4,4,4- pentafluoropropane (trifluoromethyl) -3-butene-1 (CF = CHCH ₂ (CF _{3) 2);} With 1,3,4,4,4- pentafluoropropane (trifluoromethyl) -3-butene _{(CHF = CHCF (CF 3)} 2); With 1,1,4,4,4- pentafluoropropane (trifluoromethyl) -2-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 ); A 3,3,4,4,5,5,5- heptafluoro-1-pentene _{(CF 3 CF 2 CF 2 CH} = CH 2); A 2,3,3,4,4,5,5- heptafluoro-1-pentene _{(CH 2 = CFCF 2 CF 2} CHF 2); A 1,1,3,3,5,5,5- heptafluoro-1-butene _{(CF 2 = CHCF 2 CH 2} CF 3); 3-methyl-2-butene as a 1,1,1,2,4,4,4- heptafluoropropane _{(CF 3 CF = C (CF} 3) (CH 3)); As 2,4,4,4- tetrafluoroethane (trifluoromethyl) -3-butene _{(CH 2 = CFCH (CF 3} ) 2); As 1,4,4,4- tetrafluoroethane (trifluoromethyl) -3-butene _{(CHF = CHCH (CF 3)} 2); As 1,1,1,4- tetrafluoroethane (trifluoromethyl) -2-butene _{(CH 2 FCH = C (CF} 3) 2); As 1,1,1,3- tetrafluoroethane (trifluoromethyl) -2-butene _{(CH 3 CF = C (CF} 3) 2); 1,1,1-trifluoro (trifluoromethyl) -2-butene _{((CF 3) 2 C =} CHCH 3); A 3,4,4,5,5,5- hexafluoro-2-pentene _{(CF 3 CF 2 CF = CHCH} 3); A 1,1,1,4,4,4- hexafluoro-2-methyl-2-butene _{(CF 3 C (CH 3)} = CHCF 3); 1-pentene _{(CH 2 = CHCF 2 CHFCF 3} ) a 3,3,4,5,5,5- hexafluoro; 4,4,4-trifluoro (trifluoromethyl) -3-butene _{(CH 2 = C (CF 3} ) CH 2 CF 3); 1-hexene with 1,1,2,3,3,4,4,5,5,6,6,6- dodeca-fluoro _{(CF 3 (CF 2) 3} CF = CF 2); 3-hexene _{(CF 3 CF 2 CF = CFCF} 2 CF 3) in 1,1,1,2,2,3,4,5,5,6,6,6- dodeca-fluoro; A 1,1,1,4,4,4- hexafluoro (trifluoromethyl) -2,3-bis-2-butene _{((CF 3) 2 C =} C (CF 3) 2); A 1,1,1,2,3,4,5,5,5- nonafluoro -4- (trifluoromethyl) -2-pentene _{((CF 3) 2 CFCF =} CFCF 3); A 1,1,1,4,4,5,5,5- octafluoro -2- (trifluoromethyl) -2-pentene _{((CF 3) 2 C =} CHC 2 F 5); A 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 (trifluoromethyl) -3,3-bis-1-butene _{(CH 2 = CHC (CF 3} ) 3); (CF ₃ ) ₂ C = C (CH ₃ ) (CF ₃ )) in the presence of 1,1,1,4,4,4-hexafluoro-2- (trifluoromethyl) ; (Trifluoromethyl) -4-2,3,3,5,5,5- hexafluoro-1-pentene _{(CH 2 = CFCF 2 CH (} CF 3) 2); 3-methyl-2-pentene as a 1,1,1,2,4,4,5,5,5- nonafluoro _{(CF 3 CF = C (CH} 3) CF 2 CF 3); (Trifluoromethyl) -4-1,1,1,5,5,5-hexafluoro-2-pentene _{(CF 3 CH = CHCH (CF} 3) 2); A 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- octafluoro-1-hexene _{(CH 2 = CHCF 2 CF 2} CF 2 CHF 2); A 1,1,1,4,4- pentafluoro -2- (trifluoromethyl) -2-pentene _{((CF 3) 2 C =} CHCF 2 CH 3); With 4,4,5,5,5- pentafluoropropane (trifluoromethyl) -2-pentene _{(CH 2 = C (CF 3} ) CH 2 C 2 F 5); 2-methyl-1-pentene as a 3,3,4,4,5,5,5- heptafluoropropane _{(CF 3 CF 2 CF 2 C} (CH 3) = CH 2); A 4,4,5,5,6,6,6- heptafluoro-2-hexene _{(CF 3 CF 2 CF 2 CH} = CHCH 3); A 4,4,5,5,6,6,6- heptafluoro-1-hexene _{(CH 2 = CHCH 2 CF 2} C 2 F 5); A 1,1,1,2,2,3,4- heptafluoro-3-hexene _{(CF 3 CF 2 CF = CFC} 2 H 5); (Trifluoromethyl) -4-4,5,5,5- tetrafluoro-1-pentene _{(CH 2 = CHCH 2 CF (} CF 3) 2); 4-methyl-2-pentene to 1,1,1,2,5,5,5- heptafluoropropane _{(CF 3 CF = CHCH (CF} 3) (CH 3)); As 1,1,1,3- tetrafluoroethane -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- tetra deca fluoro-2-heptene as a _{(CF 3 CF = CFCF 2 CF} 2 C 2 F 5) ; _{(5 CF 3 CF 2 CF =} CFCF 2 C 2 F) 1,1,1,2,2,3,4,5,5,6,6,7,7,7- tetra deca fluoro-3-heptene ; 1,1,1,3,4,4,5,5,6,6,7,7,7- a tree deca-fluoro-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- a tree deca-fluoro-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- tree to deca-fluoro-3-heptene _{(CF 3 CF 2 CH = CFCF} 2 C 2 F 5); 1,1,1,2,2,3,5,5,6,6,7,7,7- tree to deca-fluoro-3-heptene _{(CF 3 CF 2 CF = CHCF} 2 C 2 F 5); _{CF 2 = CFOCF 2 CF 3 (} PEVE) , and CF ₂ = fluoroolefin selected from the group consisting of CFOCF ₃ (PMVE)

And at least one fluoroolefin selected from the group consisting of fluoroolefins.

The present invention is also directed to a composition comprising at least one fluoroolefin and at least one flammable refrigerant or heat transfer fluid,

(i) a compound of the formula E or ZR ¹ CH = CHR ² , wherein R ¹ and R ² are independently C ₁ to C ₆ perfluoroalkyl groups, wherein the total number of carbons in the compound is at least 5, Olefins;

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

(iii) -1- propene (CF ₃ CF = CHF) with 1,2,3,3,3- pentafluoropropane; 1-propene to 1,1,3,3,3-pentafluoropropane _{(CF 3 CH = CF 2)} ; 1,1,2,3,3-pentafluoro-1-propene (CHF ₂ CF = CF ₂ ); 1,2,3,3-tetrafluoro-1-propene (CHF ₂ CF = CHF); 2,3,3,3- tetrafluoro-1-propene with _{(CF 3 CF = CH 2)} ; 1,1,2,3-tetrafluoro-1-propene (CH ₂ FCF = CF ₂ ); 1,1,3,3-tetrafluoro-1-propene (CHF ₂ CH = CF ₂ ); 2,3,3-Trifluoro-1-propene (CHF ₂ CF = CH ₂ ); 1-propene, 3,3,3-trifluoromethyl _{(CF 3 CH = CH 2)} ; In 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); 2-butene to 1,1,1,2,3,4,4,4- octafluoro _{(CF 3 CF = CFCF 3)} ; A 1,1,2,3,3,4,4,4- octafluoro-1-butene _{(CF 3 CF 2 CF = CF} 2); 2-butene to 1,1,1,2,4,4,4- heptafluoropropane _{(CF 3 CF = CHCF 3)} ; 1,2,3,3,4,4,4-heptafluoro-1-butene (CHF = CFCF ₂ CF ₃ ); 2-butene (CHF ₂ CF = CFCF ₃₎ a 1,1,1,2,3,4,4- heptafluoropropane; As 1,3,3,3- tetrafluoroethane (trifluoromethyl) -2-1-propene _{((CF 3) 2 C =} CHF); 1,1,3,3,4,4,4- heptafluoro-1-butene as a _{(CF 2 = CHCF 2 CF 3} ); 1,1,2,3,4,4,4- heptafluoro-1-butene as a (CF ₂ = CFCHFCF _3); A 1,1,2,3,3,4,4- heptafluoro-1-butene _{(CF 2 = CFCF 2 CHF 2} ); A 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 as a _{(CHF = CHCF 2 CF 3)} ; 1-butene (CHF = CFCHFCF ₃₎ a 1,2,3,4,4,4- hexafluoro; 1,2,3,3,4,4-hexafluoro-1-butene (CHF = CFCF ₂ CHF ₂ ); 1,1,2,3,4,4- hexafluoro-2-butene as a _{(CHF 2 CF = CFCHF 2)} ; 1,1,1,2,3,4-hexafluoro- ₂ -butene (CH ₂ FCF = CFCF ₃ ); 2-butene (CHF ₂ CH = CFCF ₃₎ a 1,1,1,2,4,4- hexafluoro; 1,1,1,3,4,4- hexafluoro-2-butene as a _{(CF 3 CH = CFCHF 2)} ; 1-butene _{(CF 2 = CFCF 2 CH 2} F) to 1,1,2,3,3,4- hexafluoro; 1,1,2,3,4,4- hexafluoro-1-butene as a (CF ₂ = CFCHFCHF _2); 3,3,3-trifluoro (trifluoromethyl) -2-propene-1 _{(CH 2 = C (CF 3} ) 2); A 1,1,1,2,4- pentafluoro-2-butene _{(CH 2 FCH = CFCF 3)} ; 1,1,1,3,4- pentafluoro-2-butene as a _{(CF 3 CH = CFCH 2 F} ); 3,3,4,4,4- pentafluoro-1-butene with _{(CF 3 CF 2 CH = CH} 2); 1,1,1,4,4- pentafluorophenyl-2-butene _{(CHF 2 CH = CHCF 3)} ; 2-butene (CH ₃ CF = CFCF ₃₎ with 1,1,1,2,3- pentafluoropropane; 2,3,3,4,4- pentafluorophenyl-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- pentafluorophenyl-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 pentafluoroethyl-2-methyl-1-propene _{(CF 2 = C (CF 3} ) (CH 3)); 2- (difluoro-methyl) -3,3,3-trifluoro-1-propene _{(CH 2 = C (CHF 2} ) (CF 3)); 1-butene (CH ₂ = CFCHFCF ₃₎ with 2,3,4,4,4- pentafluoropropane; 1,2,4,4,4- pentafluorophenyl-1-butene _{(CHF = CFCH 2 CF 3)} ; 1,3,4,4,4- pentafluorophenyl-1-butene (CHF = CHCHFCF _3); 1,3,3,4,4- pentafluoro-1-butene as a _{(CHF = CHCF 2 CHF 2)} ; 1,2,3,4,4- pentafluorophenyl-1-butene (CHF = CFCHFCHF _2); 1-butene as 3,3,4,4- tetrafluoroethane _{(CH 2 = CHCF 2 CHF 2} ); 1,1-di (difluoromethyl) -2-fluoro-1-propene _{(CF 2 = C (CHF 2} ) (CH 3)); 2-methyl-1-propene _{(CHF = C (CF 3)} (CH 3)) to 1,3,3,3- tetrafluoroethane; 3,3-di (difluoromethyl) -2-fluoro-1-propene _{(CH 2 = C (CHF 2} ) 2); 2-butene-1,1,1,2-tetrafluoroethane _{(CF 3 CF = CHCH 3)} ; 2-butene as 1,1,1,3- tetrafluoroethane (CF ₃ CH = CHCF _3); 1,1,1,2,3,4,4,5,5,5- to deca-fluoro-2-pentene _{(CF 3 CF = CFCF 2 CF} 3); 1,1,2,3,3,4,4,5,5,5- to deca-fluoro-1-pentene _{(CF 2 = CFCF 2 CF 2} CF 3); A 1,1,1,4,4,4- hexafluoro (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); A 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)} ; A 1,2,3,4,4,4- hexafluoro (trifluoromethyl) -3-butene _{(CHF = CFCF (CF 3)} 2); A 1,1,2,4,4,4- hexafluoro (trifluoromethyl) -3-butene-1 _{(CF 2 = CFCH (CF 3} ) 2); A 1,1,1,4,4,4- hexafluoro (trifluoromethyl) -2-butene _{(CF 3 CH = C (CF} 3) 2); A 1,1,3,4,4,4- hexafluoro (trifluoromethyl) -3-butene-1 _{(CF 2 = CHCF (CF 3} ) 2); A 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 ); With 3,3,4,4,4- pentafluoropropane (trifluoromethyl) -2-butene _{(CH 2 = C (CF 3} ) CF 2 CF 3); With 1,1,4,4,4- pentafluoropropane (trifluoromethyl) -3-butene-1 (CF = CHCH ₂ (CF _{3) 2);} With 1,3,4,4,4- pentafluoropropane (trifluoromethyl) -3-butene _{(CHF = CHCF (CF 3)} 2); With 1,1,4,4,4- pentafluoropropane (trifluoromethyl) -2-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 ); A 3,3,4,4,5,5,5- heptafluoro-1-pentene _{(CF 3 CF 2 CF 2 CH} = CH 2); A 2,3,3,4,4,5,5- heptafluoro-1-pentene _{(CH 2 = CFCF 2 CF 2} CHF 2); A 1,1,3,3,5,5,5- heptafluoro-1-butene _{(CF 2 = CHCF 2 CH 2} CF 3); 3-methyl-2-butene as a 1,1,1,2,4,4,4- heptafluoropropane _{(CF 3 CF = C (CF} 3) (CH 3)); As 2,4,4,4- tetrafluoroethane (trifluoromethyl) -3-butene _{(CH 2 = CFCH (CF 3} ) 2); As 1,4,4,4- tetrafluoroethane (trifluoromethyl) -3-butene _{(CHF = CHCH (CF 3)} 2); As 1,1,1,4- tetrafluoroethane (trifluoromethyl) -2-butene _{(CH 2 FCH = C (CF} 3) 2); As 1,1,1,3- tetrafluoroethane (trifluoromethyl) -2-butene _{(CH 3 CF = C (CF} 3) 2); 1,1,1-trifluoro (trifluoromethyl) -2-butene _{((CF 3) 2 C =} CHCH 3); A 3,4,4,5,5,5- hexafluoro-2-pentene _{(CF 3 CF 2 CF = CHCH} 3); A 1,1,1,4,4,4- hexafluoro-2-methyl-2-butene _{(CF 3 C (CH 3)} = CHCF 3); 1-pentene _{(CH 2 = CHCF 2 CHFCF 3} ) a 3,3,4,5,5,5- hexafluoro; 4,4,4-trifluoro (trifluoromethyl) -3-butene _{(CH 2 = C (CF 3} ) CH 2 CF 3); 1-hexene with 1,1,2,3,3,4,4,5,5,6,6,6- dodeca-fluoro _{(CF 3 (CF 2) 3} CF = CF 2); 3-hexene _{(CF 3 CF 2 CF = CFCF} 2 CF 3) in 1,1,1,2,2,3,4,5,5,6,6,6- dodeca-fluoro; A 1,1,1,4,4,4- hexafluoro (trifluoromethyl) -2,3-bis-2-butene _{((CF 3) 2 C =} C (CF 3) 2); A 1,1,1,2,3,4,5,5,5- nonafluoro -4- (trifluoromethyl) -2-pentene _{((CF 3) 2 CFCF =} CFCF 3); A 1,1,1,4,4,5,5,5- octafluoro -2- (trifluoromethyl) -2-pentene _{((CF 3) 2 C =} CHC 2 F 5); A 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 (trifluoromethyl) -3,3-bis-1-butene _{(CH 2 = CHC (CF 3} ) 3); (CF ₃ ) ₂ C = C (CH ₃ ) (CF ₃ )) in the presence of 1,1,1,4,4,4-hexafluoro-2- (trifluoromethyl) ; (Trifluoromethyl) -4-2,3,3,5,5,5- hexafluoro-1-pentene _{(CH 2 = CFCF 2 CH (} CF 3) 2); 3-methyl-2-pentene as a 1,1,1,2,4,4,5,5,5- nonafluoro _{(CF 3 CF = C (CH} 3) CF 2 CF 3); (Trifluoromethyl) -4-1,1,1,5,5,5-hexafluoro-2-pentene _{(CF 3 CH = CHCH (CF} 3) 2); A 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- octafluoro-1-hexene _{(CH 2 = CHCF 2 CF 2} CF 2 CHF 2); A 1,1,1,4,4- pentafluoro -2- (trifluoromethyl) -2-pentene _{((CF 3) 2 C =} CHCF 2 CH 3); With 4,4,5,5,5- pentafluoropropane (trifluoromethyl) -2-pentene _{(CH 2 = C (CF 3} ) CH 2 C 2 F 5); 2-methyl-1-pentene as a 3,3,4,4,5,5,5- heptafluoropropane _{(CF 3 CF 2 CF 2 C} (CH 3) = CH 2); A 4,4,5,5,6,6,6- heptafluoro-2-hexene _{(CF 3 CF 2 CF 2 CH} = CHCH 3); A 4,4,5,5,6,6,6- heptafluoro-1-hexene _{(CH 2 = CHCH 2 CF 2} C 2 F 5); A 1,1,1,2,2,3,4- heptafluoro-3-hexene _{(CF 3 CF 2 CF = CFC} 2 H 5); (Trifluoromethyl) -4-4,5,5,5- tetrafluoro-1-pentene _{(CH 2 = CHCH 2 CF (} CF 3) 2); 4-methyl-2-pentene to 1,1,1,2,5,5,5- heptafluoropropane _{(CF 3 CF = CHCH (CF} 3) (CH 3)); As 1,1,1,3- tetrafluoroethane -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- tetra deca fluoro-2-heptene as a _{(CF 3 CF = CFCF 2 CF} 2 C 2 F 5) ; _{(5 CF 3 CF 2 CF =} CFCF 2 C 2 F) 1,1,1,2,2,3,4,5,5,6,6,7,7,7- tetra deca fluoro-3-heptene ; 1,1,1,3,4,4,5,5,6,6,7,7,7- a tree deca-fluoro-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- a tree deca-fluoro-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- tree to deca-fluoro-3-heptene _{(CF 3 CF 2 CH = CFCF} 2 C 2 F 5); 1,1,1,2,2,3,5,5,6,6,7,7,7- tree to deca-fluoro-3-heptene _{(CF 3 CF 2 CF = CHCF} 2 C 2 F 5); _{CF 2 = CFOCF 2 CF 3 (} PEVE) , and CF ₂ = fluoroolefin selected from the group consisting of CFOCF ₃ (PMVE)

&Lt; / RTI &gt;

Particularly useful in compositions comprising at least one flammable refrigerant and at least one fluoroolefin is a fluoro olefin that is itself non-flammable. The flammability of fluoroolefins is believed to be related to the number of fluorine and hydrogen atoms in the molecule. The following equation provides a flammability factor that can be calculated as an indicator of the predicted flammability.

Wherein,

F is the number of fluorine atoms in the molecule;

H is the number of hydrogen atoms in the molecule.

As a particular compound is determined to be experimentally flammable, a cut-off for the non-flammable fluoroolefin flammability factor is determined. The fluoroolefins were prepared using the electronic ignition source under conditions specified by ASHRAE (American Society of Heating, Refrigerating and Air-Conditioning Engineer, Inc.) Standard 34-2001 under the American Society of Testing and Materials (ASTM) , It can be determined whether it is flammable or non-flammable. This flammability test is performed using the compound of interest at various concentrations in air at 101 kPa (14.7 psia) and at a specific temperature (often 100 캜 (212 ℉)) to determine the flammability lower limit (LFL) and / Or flammability upper limit (UFL).

The flammability factors for the various fluoroolefins are described in Table 4 below, along with experimental determinations of whether they are flammable or nonflammable. Therefore, it is predictable for other fluoroolefins of the disclosure of the present invention which are most useful for combining with flammable refrigerants of the disclosure of the present invention as substantially non-flammable fluoroolefins.

The fluoroolefins listed in Table 4 can be determined based on the value of the flammability factor, whether flammable or nonflammable. If the flammability factor is greater than 0.70, the fluoroolefin may be expected to be non-flammable. If the flammability factor is less than 0.70, the fluoroolefin can be expected to be flammable.

In another embodiment of the present invention, the fluoroolefin for use in the composition with a flammable refrigerant,

(a) a fluoroolefin of the formula E or ZR ¹ CH = CHR ² , wherein R ¹ and R ² are independently a C ₁ to C ₆ perfluoroalkyl group;

(b) a poem of the formula cyclo- [CX = CY (CZW) _{n- wherein} X, Y, Z and W are independently H or F and n is an integer of 2 to 5) with a flammability factor greater than or equal to 0.70; Pentafluoroolefin; And

(c) -1- propene (CF ₃ CF = CHF) with 1,2,3,3,3- pentafluoropropane; 1-propene to 1,1,3,3,3-pentafluoropropane _{(CF 3 CH = CF 2)} ; 1,1,2,3,3-pentafluoro-1-propene (CHF ₂ CF = CF ₂ ); 2-butene to 1,1,1,2,3,4,4,4- octafluoro _{(CF 3 CF = CFCF 3)} ; A 1,1,2,3,3,4,4,4- octafluoro-1-butene _{(CF 3 CF 2 CF = CF} 2); 2-butene to 1,1,1,2,4,4,4- heptafluoropropane _{(CF 3 CF = CHCF 3)} ; 1,2,3,3,4,4,4-heptafluoro-1-butene (CHF = CFCF ₂ CF ₃ ); 2-butene (CHF ₂ CF = CFCF ₃₎ a 1,1,1,2,3,4,4- heptafluoropropane; As 1,3,3,3- tetrafluoroethane (trifluoromethyl) -2-1-propene _{((CF 3) 2 C =} CHF); 1,1,3,3,4,4,4- heptafluoro-1-butene as a _{(CF 2 = CHCF 2 CF 3} ); 1,1,2,3,4,4,4- heptafluoro-1-butene as a (CF ₂ = CFCHFCF _3); A 1,1,2,3,3,4,4- heptafluoro-1-butene _{(CF 2 = CFCF 2 CHF 2} ); A 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 as a _{(CHF = CHCF 2 CF 3)} ; 1-butene (CHF = CFCHFCF ₃₎ a 1,2,3,4,4,4- hexafluoro; 1,2,3,3,4,4-hexafluoro-1-butene (CHF = CFCF ₂ CHF ₂ ); 1,1,2,3,4,4- hexafluoro-2-butene as a _{(CHF 2 CF = CFCHF 2)} ; 1,1,1,2,3,4-hexafluoro- ₂ -butene (CH ₂ FCF = CFCF ₃ ); 2-butene (CHF ₂ CH = CFCF ₃₎ a 1,1,1,2,4,4- hexafluoro; 1,1,1,3,4,4- hexafluoro-2-butene as a _{(CF 3 CH = CFCHF 2)} ; 1-butene _{(CF 2 = CFCF 2 CH 2} F) to 1,1,2,3,3,4- hexafluoro; 1,1,2,3,4,4- hexafluoro-1-butene as a (CF ₂ = CFCHFCHF _2); 3,3,3-trifluoro (trifluoromethyl) -2-propene-1 _{(CH 2 = C (CF 3} ) 2); 1,1,1,2,3,4,4,5,5,5- to deca-fluoro-2-pentene _{(CF 3 CF = CFCF 2 CF} 3); 1,1,2,3,3,4,4,5,5,5- to deca-fluoro-1-pentene _{(CF 2 = CFCF 2 CF 2} CF 3); A 1,1,1,4,4,4- hexafluoro (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); A 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)} ; A 1,2,3,4,4,4- hexafluoro (trifluoromethyl) -3-butene _{(CHF = CFCF (CF 3)} 2); A 1,1,2,4,4,4- hexafluoro (trifluoromethyl) -3-butene-1 _{(CF 2 = CFCH (CF 3} ) 2); A 1,1,1,4,4,4- hexafluoro (trifluoromethyl) -2-butene _{(CF 3 CH = C (CF} 3) 2); A 1,1,3,4,4,4- hexafluoro (trifluoromethyl) -3-butene-1 _{(CF 2 = CHCF (CF 3} ) 2); A 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 ); With 3,3,4,4,4- pentafluoropropane (trifluoromethyl) -2-butene _{(CH 2 = C (CF 3} ) CF 2 CF 3); With 1,1,4,4,4- pentafluoropropane (trifluoromethyl) -3-butene-1 (CF = CHCH ₂ (CF _{3) 2);} With 1,3,4,4,4- pentafluoropropane (trifluoromethyl) -3-butene _{(CHF = CHCF (CF 3)} 2); With 1,1,4,4,4- pentafluoropropane (trifluoromethyl) -2-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 ); A 3,3,4,4,5,5,5- heptafluoro-1-pentene _{(CF 3 CF 2 CF 2 CH} = CH 2); A 2,3,3,4,4,5,5- heptafluoro-1-pentene _{(CH 2 = CFCF 2 CF 2} CHF 2); A 1,1,3,3,5,5,5- heptafluoro-1-butene _{(CF 2 = CHCF 2 CH 2} CF 3); 3-methyl-2-butene as a 1,1,1,2,4,4,4- heptafluoropropane _{(CF 3 CF = C (CF} 3) (CH 3)); As 2,4,4,4- tetrafluoroethane (trifluoromethyl) -3-butene _{(CH 2 = CFCH (CF 3} ) 2); As 1,4,4,4- tetrafluoroethane (trifluoromethyl) -3-butene _{(CHF = CHCH (CF 3)} 2); As 1,1,1,4- tetrafluoroethane (trifluoromethyl) -2-butene _{(CH 2 FCH = C (CF} 3) 2); As 1,1,1,3- tetrafluoroethane (trifluoromethyl) -2-butene _{(CH 3 CF = C (CF} 3) 2); 1-hexene with 1,1,2,3,3,4,4,5,5,6,6,6- dodeca-fluoro _{(CF 3 (CF 2) 3} CF = CF 2); 3-hexene _{(CF 3 CF 2 CF = CFCF} 2 CF 3) in 1,1,1,2,2,3,4,5,5,6,6,6- dodeca-fluoro; A 1,1,1,4,4,4- hexafluoro (trifluoromethyl) -2,3-bis-2-butene _{((CF 3) 2 C =} C (CF 3) 2); A 1,1,1,2,3,4,5,5,5- nonafluoro -4- (trifluoromethyl) -2-pentene _{((CF 3) 2 CFCF =} CFCF 3); A 1,1,1,4,4,5,5,5- octafluoro -2- (trifluoromethyl) -2-pentene _{((CF 3) 2 C =} CHC 2 F 5); A 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 (trifluoromethyl) -3,3-bis-1-butene _{(CH 2 = CHC (CF 3} ) 3); (CF ₃ ) ₂ C = C (CH ₃ ) (CF ₃ )) in the presence of 1,1,1,4,4,4-hexafluoro-2- (trifluoromethyl) ; (Trifluoromethyl) -4-2,3,3,5,5,5- hexafluoro-1-pentene _{(CH 2 = CFCF 2 CH (} CF 3) 2); 3-methyl-2-pentene as a 1,1,1,2,4,4,5,5,5- nonafluoro _{(CF 3 CF = C (CH} 3) CF 2 CF 3); (Trifluoromethyl) -4-1,1,1,5,5,5-hexafluoro-2-pentene _{(CF 3 CH = CHCH (CF} 3) 2); 1,1,1,2,3,4,4,5,5,6,6,7,7,7- tetra deca fluoro-2-heptene as a _{(CF 3 CF = CFCF 2 CF} 2 C 2 F 5) ; _{(5 CF 3 CF 2 CF =} CFCF 2 C 2 F) 1,1,1,2,2,3,4,5,5,6,6,7,7,7- tetra deca fluoro-3-heptene ; 1,1,1,3,4,4,5,5,6,6,7,7,7- a tree deca-fluoro-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- a tree deca-fluoro-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- tree to deca-fluoro-3-heptene _{(CF 3 CF 2 CH = CFCF} 2 C 2 F 5); And a 3-heptene _{(CF 3 CF 2 CF = CHCF} 2 C 2 F 5) in a tree 1,1,1,2,2,3,5,5,6,6,7,7,7- deca fluoro Fluoroolefins selected from the group consisting of

&Lt; / RTI &gt; fluoroolefin.

In another embodiment, the fluoroolefins of the present disclosure, which may be particularly useful in combination with flammable refrigerants,

(a) a fluoroolefin of the formula E or ZR ¹ CH = CHR ² , wherein the flammability factor is greater than or equal to 0.70, wherein R ¹ and R ² are independently C ₁ to C ₆ perfluoroalkyl groups; And

(b) a poem of the formula cyclo- [CX = CY (CZW) _{n- wherein} X, Y, Z and W are independently H or F and n is an integer of 2 to 5) with a flammability factor greater than or equal to 0.70; Cyclic olefin

And at least one fluoroolefin selected from the group consisting of fluoroolefins.

Although the flammability parameter provides a reference for predicting the flammability of a particular fluoroolefin compound, certain variables such as the position of the hydrogen atom on the molecule (certain isomers with the given molecular formula are considered combustible, while other isomers are non-flammable) Can exist. Thus, the flammability factor can only be used as a means to predict flammability characteristics.

The flammable refrigerant of the present invention includes any compound that can appear to proliferate the flame under certain conditions of composition upon mixing with temperature, pressure, and air. The flammable refrigerant was tested using an electronic ignition source under the conditions specified by ASHRAE (American Society of Heating, Refrigerating and Air-Conditioning Engineer, Inc.) Standard 34-2001 under the American Society of Testing and Materials (ASTM) &Lt; / RTI &gt; This flammability test can be carried out using refrigerants at various concentrations in the air at 101 kPa (14.7 psia) and at a specific temperature (typically 100 ° C (212 ° F)) or at room temperature (about 23 ° C (73 ° F) The flammability lower limit (LFL) and / or flammability upper limit (UFL) of the test compound is measured.

Substantially, the refrigerant may be classified as flammable if it leaks from the refrigeration unit or air conditioner and can cause a fire when in contact with the ignition source.

Flammable refrigerants of the present invention include carbon (HFC), an olefin, fluoroalkyl fluoroalkyl ether, hydrocarbon ethers, hydrocarbons, ammonia (NH _3), and combinations thereof as hydrochloride acid.

Examples of the flammable HFC refrigerant include a mixture of difluoromethane (HFC-32), fluoromethane (HFC-41), 1,1,1-trifluoroethane (HFC-143a), 1,1,2- Ethane (HFC-143), 1,1-difluoroethane (HFC-152a), fluoroethane (HFC-161), 1,1,1-trifluoropropane (HFC-263fb) 1,3,3-pentafluoropropane (HFC-365mfc), and combinations thereof. These flammable HFC refrigerants are commercially available from many sources, such as chemical synthesis companies, or can be prepared by the synthetic methods disclosed in the art.

The flammable refrigerant of the present invention comprises 1,2,3,3-tetrafluoro-1-propene (HFC-1234ye); 1,3,3,3-tetrafluoro-1-propene (HFC-1234ze); 2,3,3,3-tetrafluoro-1-propene (HFC-1234yf); 1,1,2,3-tetrafluoro-1-propene (HFC-1234yc); 1,1,3,3-tetrafluoro-1-propene (HFC-1234zc); 2,3,3-Trifluoro-1-propene (HFC-1243yf); 3,3,3-trifluoro-1-propene (HFC-1243zf); 1,1,2-Trifluoro-1-propene (HFC-1243yc); 1,1,3-trifluoro-1-propene (HFC-1243zc); 1,2,3-trifluoro-1-propene (HFC-1243ye); And 1,3,3-trifluoro-1-propene (HFC-1243ze).

The flammable refrigerant of the present invention further comprises a fluoroether which is similar to hydrofluorocarbons and which is also a compound containing at least one ether group oxygen atom. Representative fluoroether refrigerants include, but are not limited to, commercially available C ₄ F ₉ OC ₂ H ₅ .

The flammable refrigerant of the present invention further comprises a hydrocarbon refrigerant. Representative hydrocarbon refrigerants include propane, propylene, cyclopropane, n-butane, isobutane, n-pentane, 2-methylbutane (isopentane), cyclobutane, cyclopentane, 2,2- Dimethylbutane, 2,3-dimethylbutane, 2,3-dimethylpentane, 2-methylhexane, 3-methylhexane, 2-methylpentane, 3-ethylpentane, 3-methylpentane, cyclohexane, But are not limited to, cyclopentane and n-hexane. Flammable hydrocarbon refrigerants are readily available from a number of commercial sources.

The combustible refrigerant of the present invention is a hydrocarbon ether such as dimethyl ether (DME, CH ₃ OCH ₃ ) and methyl t-butyl ether (MTBE, (CH ₃ ) ₃ COCH ₃ ), both of which are available from numerous commercial sources .

Flammable refrigerants of the present invention, further includes a commercially available compound, ammonia (NH _3).

The flammable refrigerant of the present invention may be a mixture of two or more combustible refrigerants (e. G., Two HFCs or HFCs and hydrocarbons), which are considered to be a verified or substantially combustible refrigerant under the ASTM conditions described herein Mixtures or mixtures of more than one type of refrigerant such as mixtures comprising flammable refrigerants and non-flammable refrigerants.

R-134a, R-23, R125, R-236fa, R-245fa, and HCFC-22 / HFC-152a / HCFC- HFC-143a / HFC-134a (also known as ASHRAE designation R-404 or R-404A), a mixture of HFC- HCFC-22 / HFC-143a / HFC-125 (also known as ASHRAE designation R408 or R-407A, R-407B and R- HCFC-124 / HCFC-142b (also known as ASHRAE designation R-409 or R-409A), HFC-32 / HFC-125 (known as ASHRAE designation R-410A) And HFC-125 / HFC-143a (ASHRAE designations: R-507 or R507A) and carbon dioxide.

Examples of mixtures of more than one combustible refrigerant include propane / isobutane; HFC-152a / isobutane, R32 / propane; R32 / isobutane; And HFC / carbon dioxide mixtures such as HFC-152a / CO ₂ .

One aspect of the present invention is to provide a non-combustible refrigerant having a global warming index of less than 150, preferably less than 50. [ Another aspect of the invention is to reduce the flammability of the mixture by adding a non-flammable fluoroolefin to the flammable cryogen.

If a particular refrigerant is flammable, it may appear that adding a non-flammable compound to the flammable refrigerant may create a non-flammable refrigerant composition. Examples of such non-flammable refrigerant blends include R-410A (HFC-32 is a flammable refrigerant, HFC-125 is nonflammable), and R-407C (HFC-32 is a flammable refrigerant and HFC- Is not flammable).

 A composition of the present invention useful as a refrigerant or heat transfer fluid comprising one or more fluoroolefins and one or more flammable refrigerants comprises an effective amount of a fluoroolefin to produce a composition that is non-flammable based on the results of ASTM E681-01 can do.

The compositions of the present invention comprising at least one combustible refrigerant and at least one fluoroolefin may contain from about 1 wt% to about 99 wt% of a fluoroolefin and from about 99 wt% to about 1 wt% of a flammable refrigerant have.

In another embodiment, the compositions of the present invention may contain from about 10% to about 80% fluoroolefin and from about 90% to about 20% combustible refrigerant. In another embodiment, the compositions of the present invention may contain from about 20% to about 70% by weight of fluoroolefins and from about 80% to about 30% by weight of a flammable refrigerant.

An embodiment of the disclosure of the present invention is of particular importance where the fluoroolefin comprises HFC-1225ye and the flammable refrigerant comprises HFC-32 (difluoromethane). When measured by ASTM 681-01, compositions containing less than 37 wt% HFC-32 were non-flammable and compositions containing greater than 38 wt% HFC-32 were determined to be flammable. The disclosure of the present invention provides a non-flammable composition comprising from about 1.0 wt% to about 37.0 wt% HFC-32 and from about 99.0 wt% to about 63 wt% HFC-1225ye.

Also, embodiments of the disclosure of the present invention wherein the composition comprises HFC-1225ye, HFC-32 and HFC-125 are of particular importance. The composition of the present invention comprises about 20 wt% to about 95 wt% HFC-1225ye, about 1.0 wt% to about 65 wt% HFC-32, and about 1.0 wt% to about 40 wt% HFC-125 do. In yet another embodiment, the composition comprises from about 30 wt% to about 90 wt% HFC-1225ye, from about 5.0 wt% to about 55 wt% HFC-32, and from about 1.0 wt% to about 35 wt% . In another embodiment, the composition comprises from about 40% to about 85% HFC-1225ye, from about 10% to about 45% HFC-32, and from about 1.0% to about 28% HFC-125 . Compositions containing less than about 40% by weight of HFC-32 are expected to be non-flammable. This flammability range varies from less than about 45 wt.% HFC-32 to less than about 37 wt.% HFC-32, depending on the relative proportions of HFC-1225ye and HFC-125 present in the composition.

In another particularly important embodiment, the flammable refrigerant comprises a non-flammable fluoroolefin and HFC-1243zf, which is intended to reduce flammability of the overall composition. The composition may comprise from about 1.0 wt% to about 99 wt% HFC-1243zf and from about 99 wt% to about 1.0 wt% HFC-1225ye. The composition may comprise from about 40 wt% to about 70 wt% HFC-1243zf and from about 60 wt% to about 30 wt% HFC-1225ye.

In another particularly important embodiment, the composition comprises from about 1.0% to about 98% by weight of HFC-1243zf; From about 1.0 wt% to about 98 wt% HFC-1225ye; And about 1.0 wt% to about 50 wt% HFC-125. Alternatively, the composition may comprise from about 40% to about 70% by weight of HFC-1243zf; About 20 wt% to about 60 wt% HFC-1225ye; And from about 1.0 wt% to about 10 wt% HFC-125.

In another particularly important embodiment, the composition comprises from about 1.0% to about 98% by weight of HFC-1243zf; From about 1.0 wt% to about 98 wt% HFC-1225ye; And about 1.0 wt% to about 50 wt% HFC-32. Alternatively, the composition may comprise from about 40% to about 70% by weight of HFC-1243zf; About 20 wt% to about 60 wt% HFC-1225ye; And about 1.0 wt% to about 10 wt% HFC-32.

In another particularly important embodiment, the composition comprises from about 1.0% to about 97% by weight of HFC-1243zf; About 1.0 wt% to about 97 wt% HFC-1225ye; About 1.0 wt% to about 50 wt% HFC-125; And about 1.0 wt% to about 50 wt% HFC-32. Alternatively, the composition may comprise from about 40% to about 70% by weight of HFC-1243zf; About 20 wt% to about 60 wt% HFC-1225ye; And about 1.0 wt% to about 10 wt% HFC-125; And about 1.0 wt% to about 10 wt% HFC-32.

The present invention is also directed to a method of reducing flammability of a flammable refrigerant, including combining a flammable refrigerant with one or more fluoroolefins. The amount of fluoroolefin added should be an effective amount to produce a non-flammable composition as determined by ASTM 681-01.

The compositions of the present invention may be used in refrigeration, air conditioning, or heat pump systems in combination with a desiccant to aid in the removal of moisture. The desiccant may comprise a molecular sieve based on activated alumina, silica gel or zeolite. Representative molecular sieves include MOLSIV XH-7, XH-6, XH-9 and XH-11 (UOP LLC, Des Plaine, IL). Desiccants having small molecular sizes such as HFC-32, XH-11 are preferred for refrigerants.

The composition of the present invention may further comprise at least one lubricant. The lubricants of the present invention include those suitable for use with refrigeration or air conditioning devices. These lubricants are those commonly used in compression refrigeration systems using chlorofluorocarbon refrigerants. Such lubricants and their properties are discussed in the 1990 ASHRAE Handbook, Refrigeration Systems and Applications, chapter 8, "Lubricants in Refrigeration Systems ", pages 8.1 through 8.21, incorporated herein by reference. The lubricants of the present invention may include those conventionally known as "mineral oil" in the field of compression refrigeration lubrication. The mineral oil may be selected from the group consisting of paraffins (i.e., straight and branched chain carbon chains, saturated hydrocarbons), naphthenes (i.e., cyclic paraffins) and aromatic Unsaturated cyclic hydrocarbons). The lubricants of the present invention may additionally include those conventionally known as "synthetic oils" in the field of compression refrigeration lubrication. Synthetic oils include alkylaryl (i.e., linear and branched alkyl alkylbenzenes), synthetic paraffins and naphthenes, and poly (alpha olefins). Representative conventional lubricants of the present invention are commercially available BVM 100 N (paraffinic mineral oil sold by BVA Oils), Suniso® 3GS and Suniso® 5GS (Naphthenic mineral oil sold by Crompton Co.), Sontex® 372LT (naphthenic mineral oil sold by Pennzoil), Calumet® RO-30 (Naphthenic mineral oil sold by Calumet Lubricants), Zerol 75, Zerol 150 and Zerol 500 (a linear alkylbenzene marketed by Shrieve Chemicals) and HAB 22 Branched alkylbenzene marketed by Nippon Oil).

The lubricants of the present invention further include those that are designed for use with hydrofluorocarbon refrigerants and that are compatible with the refrigerants of the present invention under the operating conditions of compression refrigeration and air conditioning equipment. Such lubricants and their properties are discussed in "Synthetic Lubricants and High-Performance Fluids", R. L. Shubkin, editor, Marcel Dekker, 1993. Such lubricants include polyol esters (POE) such as Castrol 100 (Castrol), polyalkylene glycols (PAG) such as Dow (Dow Chemical, Midland, Mich. Dow Chemical), and polyvinyl ethers (PVE).

The lubricant of the present invention is selected in consideration of the requirements of a given compressor and the environment in which the lubricant is exposed.

In order to improve lubricity and system stability, refrigeration system additives commonly used in the compositions of the present invention may optionally be added. These additives are generally known in the refrigeration compressor lubrication field and include abrasion inhibitors, extreme pressure lubricants, corrosion and oxidation inhibitors, metal surface deactivators, foam and vesiculators, leak detectors, and the like . Generally, these additives are present in only small amounts relative to the total lubricant composition. They are typically used at a concentration of from about 0.1% to about 3% for each additive. These additives are selected based on the individual system requirements. Some typical examples of such additives may include, but are not limited to, lubricity enhancing additives such as, for example, phosphoric acid and alkyl or aryl esters of thiophosphates. In addition, metal dialkyldithiophosphates (e.g., zinc dialkyldithiophosphate or ZDDP, Lubrizol 1375) and other sources of such chemical groups may be used in the compositions of the present invention. Other antiwear additives include natural oil and asymmetric polyhydroxyl lubricant additives such as Synergol TMS (International Lubricants). Similarly, stabilizers such as antioxidants, free radicals (E.g., butylated hydroxytoluene, or BHT), hydroxylamine, thiol, phosphite, epoxide &lt; RTI ID = 0.0 &gt; But are not limited to, lactones. Water scavengers include, but are not limited to, orthoesters such as trimethyl-, triethyl-, or tripropyl orthoformate. Or combinations thereof.

In one embodiment, the present invention is directed to a process for preparing a fluorinated olefin comprising reacting one or more fluoroolefins and one or more fluoroolefins selected from the group consisting of thiophosphates, butylated triphenylphosphorothionates, organic phosphates, dialkyl thiophosphate esters, terpenes, terpenoids, fullerenes, But are not limited to, polyoxyalkylated aromatic, epoxide, fluorinated epoxide, oxetane, ascorbic acid, thiol, lactone, thioether, nitromethane, alkylsilane, benzophenone derivative, arylsulfide, divinylterephthalate, At least one stabilizer selected from the group consisting of diphenyl terephthalate, alkyl amines, sterically hindered amine antioxidants, and phenols. Alkylamines can include triethylamine, tributylamine, diisopropylamine, triisopropylamine, triisobutylamine, and other sources of such alkylamine compound families.

In another embodiment, the stabilizers of the present invention may comprise certain combinations of stabilizers. One combination of particularly important stabilizers includes one or more terpenes or terpenoids. These terpenes or terpenoids may be combined with one or more compounds selected from epoxides, fluorinated epoxides and oxetanes.

Terpene is a hydrocarbon compound characterized by a structure containing more than one isoprene (2-methyl-1,3-butadiene) repeat unit. Terpenes can be bicyclic or cyclic. Representative terpenes include, but are not limited to, myrcene (2-methyl-6-methyleneocta-l, 7-diene), alo-cymene, beta -ocymene, terbene, limonene (or d- limonene), retinal, Alpha-pinene), menthol, geraniol, farnesyl, phytol, vitamin A, terpinene, delta-3-carene, terpinolene, phellandrene, pentene and mixtures thereof. Do not. Terpene stabilizers are commercially available or can be prepared by methods known in the art or isolated from natural sources.

Terpenoids are natural products and related compounds which are characterized by a structure containing more than one isoprene repeat unit and which optionally contain oxygen. Representative terpenoids include carotenoids such as lycopene (CAS Registry Number [502-65-8]), beta carotene (CAS Registry Number [7235-40-7]) and xanthophyll, [144-68-3]); Retinoids such as heptacoxanthin (CAS registry number [512-39-0]), and isotretinoin (CAS registry number [4759-48-2]); Aviethane (CAS registration number [640-43-7]); Ambal acid (CAS Registry Number [24749-18-6]); Ari Stallan (CAS Registry Number [29788-49-6]); Artic acid (CAS registration number [24379-83-7]); Veyran (CAS registration number [2359-83-3]), bisabollan (CAS registration number [29799-19-7]); Bornan (CAS registration number [464-15-3]); Calofil (CAS registration number [20479-00-9]); Sedran (CAS registration number [13567-54-9]); (CAS registration number [545-22-2]); Dreman (CAS registration number [5951-58-6]); Eremofilan (CAS registration number [3242-05-5]); Uesden (CAS registration number [473-11-0]); Pennchan (CAS registration number [6248-88-0]); Gamma serine (CAS Registry Number [559-65-9]); German Mark (CAS registration number [645-10-3]); (CAS registration number [6902-95-0]); Gray anoxic acid (CAS registration number [39907-73-8]); Guaian (CAS registration number [489-80-5]); Himachiran (CAS registration number [20479-45-2]); Registration number (CAS registration number [471-62-5]); Closed Caption (CAS Registration Number [430-19-3]); Kauren (CAS registration number [1573-40-6]); Labs (CAS registration number [561-90-0]); LANOSSTAN (CAS registration number [474-20-4]); (CAS registration number [464-99-3]); p-menthane (CAS registration number [99-82-1]); Olean (CAS registration number [471-67-0]); Opiobolan (CAS Registry Number [20098-65-1]); Picric acid (CAS registry number [35732-97-9]); Pimaran (CAS registration number [30257-03-5]); Evacuation (CAS registration number [473-55-2]); Grape cardia (CAS registration number [471-78-3]); Protostan (CAS registration number [70050-78-1]); Losan (CAS registration number [6812-82-4]); Taxane (CAS registration number [1605-68-1]); Tutan (CAS registration number [471-12-5]); Tricotecan (CAS registration number [24706-08-9]); And uric acid (CAS registration number [464-93-7]). The terpenoids of the present invention are either commercially available or can be prepared by methods known in the art or can be isolated from natural sources.

In one embodiment, terpenes or terpenoid stabilizers can be combined with one or more epoxides. Representative epoxides include 1,2-propylene oxide (CAS Registry Number [75-56-9]); 1,2-butylene oxide (CAS registration number [106-88-7]); Or mixtures thereof.

In another embodiment, the terpene or terpenoid stabilizer of the present invention may be combined with one or more fluorinated epoxides. The fluorinated epoxide of the present invention can be represented by the following formula (3).

(3)

Wherein each of R ² to R ⁵ is H, alkyl having 1 to 6 carbon atoms or fluoroalkyl having 1 to 6 carbon atoms, provided that at least one of R ² to R ⁵ is a fluoroalkyl group .

Representative fluorinated epoxide stabilizers include, but are not limited to, trifluoromethyloxirane and 1,1-bis (trifluoromethyl) oxirane. Such compounds may be prepared by methods known in the art, for example, Journal of Fluorine Chemistry, volume 24, pages 93-104 (1984), Journal of Organic Chemistry, volume 56, pages 3187 to 3189 (1991) , And Journal of Fluorine Chemistry, volume 125, pages 99-105 (2004).

In another embodiment, the terpene or terpenoid stabilizer of the present invention may be combined with at least one oxetane. The oxetane stabilizer of the present invention may be a compound having at least one oxetane group, which is represented by the following formula (4).

&Lt; Formula 4 >

Wherein R ₁ to R ₆ are the same or different and can be selected from hydrogen, alkyl or substituted alkyl, aryl or substituted aryl.

Representative oxetane stabilizers include 3-ethyl-3-hydroxymethyl-oxetane, such as OXT-101 (Toagosei Co., Ltd); 3-ethyl-3 - ((phenoxy) methyl) -oxetane, such as OXT-211 (Doagosei Co., Ltd.); And 3-ethyl-3 - ((2-ethyl-hexyloxy) methyl) -oxetane such as OXT-212 (Doagosei Company, Limited).

Another particularly important embodiment is the combination of stabilizers comprising fullerene. The fullerene stabilizer may be combined with at least one compound selected from the group consisting of epoxides, fluorinated epoxides and oxetanes. The epoxides, fluorinated epoxides and oxetanes for combination with fullerene are described hereinabove for combinations with terpenes or terpenoids.

Another particularly important embodiment is the combination of stabilizers comprising phenol. The phenolic stabilizer may be combined with at least one compound selected from the group consisting of epoxides, fluorinated epoxides and oxetanes. The epoxides, fluorinated epoxides and oxetanes for combination with phenol are described hereinabove for combinations with terpenes or terpenoids.

Phenolic stabilizers may be any substituted or unsubstituted substituted or unsubstituted phenol compounds including phenol containing one or more substituted or unsubstituted cyclic, straight or branched aliphatic substituents, such as alkylated monophenols, e.g., For example 2,6-di-tert-butyl-4-methylphenol; 2,6-di-tert-butyl-4-ethylphenol; 2,4-dimethyl-6-tert-butylphenol; Tocopherol; Etc., hydroquinone and alkylated hydroquinone, for example t-butylhydroquinone, other derivatives of hydroquinone; , Hydroxylated thiodiphenyl ethers such as 4,4'-thio-bis (2-methyl-6-tert-butylphenol); 4,4'-thiobis (3-methyl-6-tert-butylphenol); 2,2'-thiobis (4-methyl-6-tert-butylphenol); Alkylidene-bisphenols such as 4,4'-methylenebis (2,6-di-tert-butylphenol); 4,4'-bis (2,6-di-tert-butylphenol); Derivatives of 2,2'- or 4,4-biphenol diols; 2,2'-methylenebis (4-ethyl-6-tert-butylphenol); 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- or 4,4-biphenyldiols such as 2,2'-methylenebis (4-ethyl-6-tert-butylphenol); Butylated hydroxytoluene (BHT), a bisphenol containing a hetero atom such as 2,6-di-tert-alpha-dimethylamino-p-cresol, 4,4-thiobis (6-tert- butyl-m - cresol); Etc; Acylaminophenol; 2,6-di-tert-butyl-4- (N, N'-dimethylaminomethylphenol); Sulfides such as bis (3-methyl-4-hydroxy-5-tert-butylbenzyl) sulfide; Bis (3,5-di-tert-butyl-4-hydroxybenzyl) sulfide; And the like.

In one embodiment of the invention, these combinations of stabilizers comprising terpenes or terpenoids, or one or more compounds selected from the group consisting of fullerene or phenol and epoxides, fluorinated epoxides and oxetanes,

Aleoxalyl bis (benzylidene) hydrazide (CAS Registry No. 6629-10-3);

N, N'-bis (3,5-di-tert-butyl-4-hydroxyhydrocinnamoyl hydrazine) (CAS Registry Number 32687-78-8);

2,2'-oxamidobis-ethyl- (3,5-di-tert-butyl-4-hydroxyhydrocinnamate) (CAS Registry No. 70331-94-1);

N, N ' - (di salicylidene) -1,2-propanediamine (CAS Registry No. 94-91-1); And

Ethylenediaminetetraacetic acid (CAS Registry No. 60-00-4) and salts thereof

Lt; RTI ID = 0.0 &gt; stabilizer &lt; / RTI &gt;

In another embodiment of the present invention, these combinations of stabilizers comprising terpenes or terpenoids, or one or more compounds selected from the group consisting of fullerene or phenol and epoxide, fluorinated epoxide and oxetane, Triethylamine; Tributylamine; Triisopropylamine; Diisobutylamine; Triisopropylamine; Triisobutylamine; And one or more alkylamines selected from the group consisting of sterically hindered amine antioxidants.

The composition of the present invention can be used in combination with other components such as hydrofluorocarbons (HFCs), deuterated hydrocarbons, deuterated hydrofluorocarbons, perfluorocarbons, fluoroethers, brominated compounds, iodinated compounds, alcohols, aldehydes, ketones, ₂ O), and combinations thereof. &Lt; Desc / Clms Page number 7 &gt; The tracers used in the present invention are compositions that are different from those used as refrigerants or heat transfer fluids and are added to refrigerant and heat transfer compositions in predetermined amounts to enable detection of any dilution, U.S. Patent Application No. 11 / 062,044, filed February 18, 2006).

Exemplary tracer compounds for use in the compositions of the present invention are listed in Table 5 below.

Compounds listed in Table 5 are either commercially available (from a chemical supplier) or can be prepared by methods known in the art.

A single tracer compound may be used in the compositions of the present invention in combination with a refrigeration / heating fluid, or multiple tracker compounds may be combined in any ratio to provide a tracer blend. The tracer blend may contain a plurality of tracer compounds from the same class of compounds or a plurality of tracer compounds from different classes of compounds. For example, the tracer blend may contain two or more dehydrohalogenated hydrofluorocarbons, or one dehydrogenated hydrofluorocarbon in combination with one or more perfluorocarbons.

In addition, some of the compounds of Table 4 exist as a number of structures or optical isomers. A single isomer or a plurality of isomers of the same compound may be used in any ratio to produce the tracer compound. In addition, single or multiple isomers of a given compound may be combined with any number of other compounds in any ratio to provide a tracer blend.

The tracer compound or tracer blend may be present in the composition at a total concentration of about 50 weight parts per million (ppm) to about 1000 ppm. Preferably, the tracer compound or tracer blend is present at a total concentration of from about 50 ppm to about 500 ppm, and most preferably, the tracer compound or tracer blend is present at a total concentration of from about 100 ppm to about 300 ppm.

The composition of the present invention may further comprise an ultraviolet (UV) dye and optionally a solubilizing agent. The UV dye can be used to detect the leakage of the refrigerant composition or heat transfer fluid by allowing the refrigeration, air conditioning, heating pump device to observe the fluorescence of the dye in the refrigerant or heat transfer fluid composition at or near the leak point in the device Lt; / RTI &gt; Fluorescence of the dye can be observed under ultraviolet light. Solubilizing agents may be required due to the low solubility of such UV dyes in some refrigerants and heat transfer fluids.

"Ultraviolet" dyes refer to UV fluorescent compositions that absorb light in the ultraviolet or "near" ultraviolet region of the electromagnetic spectrum. It is possible to detect fluorescence generated by the UV fluorescent dye under irradiation with UV light that emits radiation having a wavelength in an arbitrary region of 10 nm to 750 nm. Thus, if a refrigerant or heat transfer fluid containing such a UV fluorescent dye leaks at a given point in a refrigeration, air conditioning, or heat pump system, fluorescence can be detected near the leak point or leak point. Such UV fluorescent dyes include, but are not limited to, naphthalimide, perylene, coumarin, anthracene, phenanthracene, xanthene, thioxanthene, naphtoxanthene, fluorescein, , But is not limited thereto. The solubilizing agent of the present invention may be selected from the group consisting of hydrocarbons, hydrocarbon ethers, polyoxyalkylene glycol ethers, amides, nitriles, ketones, chlorocarbons, esters, lactones, aryl ethers, fluoroethers, and 1,1,1- And at least one compound selected from the group consisting of

Hydrocarbon solubilizing agents of the present invention include straight chain, branched or cyclic alkanes or hydrocarbons including alkenes containing up to 16 carbon atoms and only hydrogen and no other functional groups. Representative hydrocarbon solubilizing agents include propane, propylene, cyclopropane, n-butane, isobutane, n-pentane, octane, decane and hexadecane. If the refrigerant is a hydrocarbon, it should be appreciated that the solubilizer may not be the same hydrocarbon.

Hydrocarbon ether solubilizing agents of the present invention include ethers containing only carbon, hydrogen and oxygen, such as dimethyl ether (DME).

Polyoxyalkylene glycol ether solubilizing agents of the present invention has the formula _{^{R 1 [(OR 2) x}} OR 3] y ( wherein, x is an integer from 1 to 3; y is an integer from 1 to 4 and; R ¹ is selected from an aliphatic hydrocarbon radical having from hydrogen and from 1 to 6 carbon atoms and y of the binding site and; R ² is selected from aliphatic hydrocarbylene radicals having from 2 to 4 carbon atoms; R ³ is hydrogen and from 1 to 6 Lt; ¹ &gt; and R &lt; ³ &gt; are the hydrocarbon radicals; And has a molecular weight of from about 100 to about 300 amu. As used herein, a bond site means a radical site capable of forming a covalent bond with another radical. Hydrocarbylene radical means a divalent hydrocarbon radical. In the present invention, preferred polyoxyalkylene glycol ether solubilizing agents are those represented by the formula R ¹ [(OR ² ) _x OR ³ ] _{y wherein} x is preferably 1 to 2, y is preferably 1, R ¹ And R &lt; ³ &gt; are preferably independently selected from hydrogen and aliphatic hydrocarbon radicals having from 1 to 4 carbon atoms; R &lt; ² &gt; is preferably an aliphatic radical having 2 or 3 carbon atoms, Selected from hydrocarbylene radicals; The molecular weight is preferably from about 100 to about 250 amu, and most preferably from about 125 to about 250 amu. The R &lt; ¹ &gt; and R &lt; ³ &gt; hydrocarbon radicals having from one to six carbon atoms may be linear, branched or cyclic. Representative R ¹ and R ³ hydrocarbon radicals are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert- pentyl, cyclopentyl and cyclohexyl . When the hydroxyl free radicals on the present polyoxyalkylene glycol ether solubilizer can be immiscible with certain compression refrigeration system constituent materials (for example Mylar®), R ¹ and R ³ are preferably Is an aliphatic hydrocarbon radical having from one to four carbon atoms, most preferably one carbon atom. An R ² aliphatic hydrocarbylene radical having 2 to 4 carbon atoms forms a repeat oxyalkylene radical - (OR ² ) _x -, including an oxyethylene radical, an oxypropylene radical, and an oxybutylene radical. Oxyalkylene radicals containing R ² in one polyoxyalkylene glycol ether solubilizing agent molecule may contain groups may be the same, or one molecule of a different R ² oxyalkylene. The polyoxyalkylene glycol ether solubilizing agent of the present invention preferably comprises at least one oxypropylene radical. When R &^lt; 1 &gt; is an aliphatic or cycloaliphatic hydrocarbon radical having 1 to 6 carbon atoms and y &lt; 1 &gt; bonding sites, the radical may be linear, branched or cyclic. Representative R ¹ aliphatic hydrocarbon radicals having two bonding sites include, for example, ethylene radicals, propylene radicals, butylene radicals, pentylene radicals, hexylene radicals, cyclopentylene radicals and cyclohexylene radicals. Exemplary R &lt; ^{1 &gt;} aliphatic hydrocarbon radicals having 3 or 4 bonding sites are trimethylolpropane, glycerin, pentaerythritol, 1,2,3-trihydroxycyclohexane and 1,3,5-trihydroxycyclohexane Lt; RTI ID = 0.0 &gt; polyols, &lt; / RTI &gt; by removal of their hydroxyl radicals.

Representative polyoxyalkylene glycol ether solubilizing agents _{include, CH 3 OCH 2 CH (CH} 3) O (H or CH ₃₎ (propylene glycol methyl (or dimethyl) _{ether), CH 3 O [CH 2} CH (CH 3) O ] ₂ (H or CH ₃₎ (dipropylene glycol methyl (or dimethyl) _{ether), CH 3 O [CH 2} CH (CH 3) O] 3 (H or CH ₃₎ (tripropylene glycol methyl (or dimethyl) ether _{), C 2 H 5 OCH 2} CH (CH 3) O (H or C ₂ H ₅₎ (propylene glycol ethyl (or diethyl) _{ether), C 2 H 5 O [} CH 2 CH (CH 3) O] 2 (H or C ₂ H ₅ ) (dipropylene glycol ethyl (or diethyl) ether), C ₂ H ₅ O [CH ₂ CH (CH ₃ ) O] ₃ (H or C ₂ H ₅ ) (or diethyl) _{ether), C 3 H 7 OCH 2} CH (CH 3) O (H or C ₃ H ₇₎ (propylene glycol n- propyl (or di -n- propyl) ether), C ₃ H ₇ O _{[CH 2 CH (CH 3)} O] 2 (H or C ₃ H ₇₎ (dipropylene glycol n- propyl (or di -n- propyl) _{ether), C 3 H 7 O [} CH 2 CH (CH 3) O] ₃ (H or C ₃ H ₇₎ (tripropylene glycol n- propyl (or di -n- propyl) _{ether), C 4 H 9 OCH 2} CH (CH 3) OH ( propylene glycol n- butyl ether), C ₄ H _{9 O [CH 2 CH (CH} 3) O] 2 (H or C ₄ H ₉₎ (dipropylene glycol n- butyl (or di -n- butyl) _{ether), C 4 H 9 O [} CH 2 CH (CH ₃ ) O] ₃ (H or C ₄ H ₉ ) (tripropylene glycol n-butyl (or di-n-butyl) ether), (CH ₃ ) ₃ COCH ₂ CH (CH ₃ ) OH (propylene glycol t- _{ether), (CH 3) 3 CO} [CH 2 CH (CH 3) O] 2 (H or (CH _{3) 3)} (dipropylene glycol t- butyl (or di -t- butyl) ether), (CH ₃ ) ₃ CO [CH ₂ CH (CH ₃ ) O] ₃ (H or (CH ₃ ) ₃ ) (tripropylene glycol t-butyl (or di-t-butyl) ether), C ₅ H ₁₁ OCH ₂ CH ₃₎ OH (propylene glycol n- pentyl _{ether), C 4 H 9 OCH 2} CH (C 2 H 5) OH ( butylene glycol n- butyl _{ether), C 4 H 9 O [} CH 2 CH (C 2 H 5 ) O] ₂ H (di-butylene glycol n- butyl ether), trimethylolpropane tri -n- butyl Terminus _{(C 2 H 5 C (CH} 2 O (CH 2) 3 CH 3) 3) and trimethylolpropane di -n- butyl ether _{(C 2 H 5 C (CH} 2 OC (CH 2) 3 CH 3) 2 CH ₂ OH). &Lt; / _RTI &gt;

Amide solubilizing agents of the present invention, the formula ^{R 1 C (O) NR 2} R 3 and cycloalkyl ^{- [R 4 C (O)} N (R 5)] ( wherein, R ^1, R ^2, R ³ and R ⁵ Are independently selected from aliphatic and cycloaliphatic hydrocarbon radicals having from 1 to 12 carbon atoms and R &lt; ⁴ &gt; is selected from aliphatic hydrocarbylene radicals having from 3 to 12 carbon atoms, And has a molecular weight of from about 100 to about 300 amu. The molecular weight of the amide is preferably from about 160 to about 250 amu. R ¹ , R ² , R ³ and R ⁵ are radicals containing a non-hydrocarbon substituent selected from substituted hydrocarbon radicals, ie halogen (eg fluorine, chlorine) and alkoxide (eg methoxy) May optionally be included. R ¹ , R ² , R ³ and R ⁵ are heteroatom-substituted hydrocarbon radicals which contain at least one atom of nitrogen (aza-), oxygen (oxa-) or sulfur (thia-) in the radical chain Carbon atoms) radicals. In general, there are no more than 3, preferably no more than 1, non-hydrocarbon substituents and heteroatoms for each 10 carbon atoms of R ¹ to R ³ , and in applying such molecular weight ranges, The presence of hydrocarbon substituents and heteroatoms should be considered. Preferred amide solubilizing agents are composed of carbon, hydrogen, nitrogen and oxygen. Representative R ¹ , R ² , R ³ and R ⁵ aliphatic and alicyclic hydrocarbon radicals are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert- butyl, pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, cyclohexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl and coordinated isomers thereof. Preferred embodiments, the above-described formula cycloalkyl of amide solubilizing agents, and the ^{- [R 4 C (O)} N (R 5) -] is in the R ⁴ hydrocarbylene radical (CR ⁶ R ⁷⁾ _n ones that can be expressed as, i.e. formula cyclo ^{- [(CR 6 R 7)} n C (O) N (R 5) -] of these (in this case the above-mentioned molecular weight values) to lowest (in the formula, n is from 3 to 5, an integer; R ⁵ is R &lt; ⁶ &gt; and R &lt; ⁷ &gt; are independently selected (for each n) in the manner provided above in the definition of R &^lt; ¹ &gt; to R &^lt; ³ &gt;. Formula cyclo ^{- [(CR 6 R 7)} nC (O) N (R 5) -] In the lactams represented by any R ⁶ and R ⁷ are preferably hydrogen, or a single saturated hydrocarbon radical among the n methylene units And R &lt; ⁵ &gt; is a saturated hydrocarbon radical containing 3 to 12 carbon atoms. For example, 1- (saturated hydrocarbon radical) -5-methylpyrrolidin-2-one.

Representative amide solubilizing agents include 1-octylpyrrolidin-2-one, 1-decylpyrrolidin-2-one, 1-octyl-5-methylpyrrolidin- 1-pentyl-5-methylpiperid-2-one, 1-hexylcaprolactam, 1-hexyl-5-methylpiperidin- 2-one, 1,3-dimethylpiperid-2-one, 1-methylcaprolactam, 1-butyl-pyrrolidine- 1-decyl-5-methylpyrrolidin-2-one, 1-dodecylpyrrolid-2-one, N, N-dibutylformamide And N, N-diisopropylacetamide.

The ketone solubilizing agent of the present invention is represented by the formula R ¹ C (O) R ^{2 wherein} R ¹ and R ² are independently selected from aliphatic, alicyclic and aryl hydrocarbon radicals having 1 to 12 carbon atoms And includes a ketone having a molecular weight of about 70 to about 300 amu. In the ketone, R ¹ and R ² are preferably independently selected from aliphatic and alicyclic hydrocarbon radicals having from 1 to 9 carbon atoms. The molecular weight of the ketone is preferably about 100 to 200 amu. R &lt; ¹ &gt; and R &lt; ² &gt; may be connected together to form a 5, 6 or 7 membered cyclic cyclic ketone such as cyclopentanone, cyclohexanone and cycloheptanone. R ¹ and R ² may optionally contain radicals containing a non-hydrocarbon substituent selected from substituted hydrocarbon radicals, i. E. Halogen (e. G., Fluorine, chlorine) and alkoxide (e. G. Methoxy). R ¹ and R ² are heteroatom-substituted hydrocarbon radicals, that is to say those which contain atomic nitrogen (aza-), oxygen (keto-, oxa-) or sulfur (thia-) in the radical chain ) &Lt; / RTI &gt; radicals. In general, there are no more than 3, preferably no more than 1, non-hydrocarbon substituents and heteroatoms for each 10 carbon atoms of R ¹ and R ² , and in applying such molecular weight ranges, The presence of hydrocarbon substituents and heteroatoms should be considered. Representative R ¹ and R ² aliphatic, alicyclic and aryl hydrocarbon radicals in the formula R ¹ C (O) R ² are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, Butenyl, isobutyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, cyclohexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl and coordinated isomers thereof, Silyl and phenethyl.

Representative examples of the ketone solubilizing agent include 2-butanone, 2-pentanone, acetophenone, butyrophenone, hexanophenone, cyclohexanone, cycloheptanone, 2- 2-decanone, 2-decanone, 2-decanone, 3-octanone, diisobutyl ketone, 4-ethylcyclohexanone, 2- , 2-tridecanone, dihexyl ketone, and dicyclohexyl ketone.

The nitrile solubilizing agent of the present invention is represented by R ¹ CN (wherein R ¹ is selected from aliphatic, alicyclic or aryl hydrocarbon radicals having 5 to 12 carbon atoms) and has a molecular weight of about 90 to about 200 amu / RTI &gt; In the nitrile solubilizing agent, R &lt; ^{1 &gt;} is preferably selected from aliphatic and alicyclic hydrocarbon radicals having from 8 to 10 carbon atoms. The molecular weight of the nitrile solubilizing agent is preferably about 120 to about 140 amu. R ¹ may optionally include a radical containing a non-hydrocarbon substituent selected from a substituted hydrocarbon radical, i. E., A halogen (e. G., Fluorine, chlorine) and an alkoxide (e. G., Methoxy). R ¹ is a radical which contains a heteroatom-substituted hydrocarbon radical, i.e., consisting of a carbon atom, which contains in the radical chain atomic nitrogen (aza-), oxygen (keto-, oxa-) or sulfur (thia-) May optionally be included. In general, there are no more than 3, preferably no more than 1, non-hydrocarbon substituents and heteroatoms for each 10 carbon atoms of R &lt; ¹ &gt;, and any such non-hydrocarbon substituent And the presence of heteroatoms should be considered. Representative R ¹ aliphatic, alicyclic and aryl hydrocarbon radicals in the formula R ¹ CN are selected from the group consisting of pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, cyclohexyl, heptyl, octyl, nonyl, decyl, undecyl, As well as phenyl, benzyl, cumene, mesityl, tolyl, xylyl and phenethyl. Representative examples of nitrile solubilizers include 1-cyanopentane, 2,2-dimethyl-4-cyanopentane, 1-cyanoohexane, 1-cyanoheptane, 1-cyanooctane, But are not limited to, cyanononane, 1-cyanodecane, 2-cyanodecane, 1-cyanodecane and 1-cyanododecane.

The chlorocarbon solubilizing agent of the present invention is represented by the formula RCl _{x wherein} x is selected from integers of 1 or 2 and R is selected from aliphatic and alicyclic hydrocarbon radicals having 1 to 12 carbon atoms, And chlorocarbons having a molecular weight of about 100 to about 200 amu. The molecular weight of the chlorocarbon solubilizing agent is preferably about 120 to 150 amu. Representative R aliphatic and alicyclic hydrocarbon radicals in the formula RCl _x are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, , Cyclohexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl and coordinated isomers thereof.

Representative chlorocarbon solubilizers include, but are not limited to, 3- (chloromethyl) pentane, 3-chloro-3-methylpentane, 1-chloroohexane, 1,6-dichlorohexane, , 1-chlorodecane, and 1,1,1-trichlorodecane.

The ester solubilizing agents of the present invention include esters represented by the formula R ¹ CO ₂ R ^{2 wherein} R ¹ and R ² are independently selected from linear and cyclic, saturated and unsaturated, alkyl and aryl radicals . Preferred esters are based on the elements C, H and O and have a molecular weight of about 80 to about 550 amu.

Representative esters include (CH ₃ ) ₂ CHCH ₂ OOC (CH ₂ ) _2-4 OCOCH ₂ CH (CH ₃ ) ₂ (diisobutyl dicarboxylate), ethylhexanoate, ethylheptanoate, Exxate 700 "(commercial C ₇ alkyl acetate)," N, N'-diphenylmethane diisocyanate, diisopropylethylphosphate, Acquate 800 "(commercially available C ₈ alkyl acetate), dibutyl phthalate, and tert-butyl acetate.

The lactone solubilizing agent of the present invention includes lactones represented by the following structural formulas [A], [B] and [C].

These lactones contain a functional group -CO ₂ - in the ring with 6 atoms (A) or preferably 5 atoms (B), and in the case of structures [A] and [B], R ₁ to R ₈ are independently Hydrogen or a linear, branched, cyclic, bicyclic, saturated and unsaturated hydrocarbyl radical. Each of R ₁ to R ₈ may be connected to form a ring having another R ₁ to R ₈ . The lactone may have an alicyclic alkylidene group as in structure [C], wherein R ₁ to R ₆ are independently selected from hydrogen or linear, branched, cyclic, bicyclic, saturated and unsaturated hydrocarbyl radicals do. Each of R ₁ to R ₆ may be connected to form a ring having another R ₁ to R ₆ . The lactone solubilizer has a molecular weight range of from about 80 to about 300 amu, preferably from about 80 to about 200 amu.

Exemplary lactone solubilizers include, but are not limited to, the compounds listed in Table 6 below.

The lactone solubilizer generally has a kinematic viscosity at 40 DEG C of less than about 7 cSt. For example, at 40 占 폚, gamma-undecalactone has a kinematic viscosity of 5.4 cSt and cis- (3-hexyl-5-methyl) dihydrofuran-2-one has a kinematic viscosity of 4.5 cSt. Lactone solubilizers are commercially available or may be prepared by methods such as those described in U.S. Patent Application No. 10 / 910,495, filed August 3, 2004, which is incorporated herein by reference.

The aryl ether solubilizing agent of the present invention is a compound having the formula R ¹ OR ^{2 wherein} R ¹ is selected from an aryl hydrocarbon radical having 6 to 12 carbon atoms and R ² is an aliphatic hydrocarbon radical having 1 to 4 carbon atoms , And includes aryl ethers having a molecular weight of from about 100 to about 150 amu. Representative R ¹ aryl radicals in the formula R ¹ OR ² include phenyl, biphenyl, cumenyl, mesityl, tolyl, xylyl, naphthyl and pyridyl. Representative R ² aliphatic hydrocarbon radicals in the formula R ¹ OR ² include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and tert-butyl. Representative aromatic ether solubilizers include, but are not limited to, methyl phenyl ether (anisole), 1,3-dimethyloxybenzene, ethyl phenyl ether and butyl phenyl ether.

The fluoroether solubilizing agent of the present invention is a compound of the formula R ¹ OCF ₂ CF ₂ H wherein R ¹ is selected from aliphatic, cycloaliphatic and aromatic hydrocarbon radicals having from about 5 to about 15 carbon atoms, Lt; RTI ID = 0.0 &gt; linear &lt; / RTI &gt; saturated alkyl radical. Representative fluoroether solubilizers include, but are not limited to, C ₈ H ₁₇ OCF ₂ CF ₂ H and C ₆ H ₁₃ OCF ₂ CF ₂ H. If the refrigerant is a fluoroether, it should be appreciated that the solubilizer may not be the same fluoroether.

The fluoroether solubilizer may further comprise an ether derived from a fluoroolefin and a polyol. Fluoroolefin is CF ₂ ═CXY wherein X is hydrogen, chlorine or fluorine, Y is chlorine, fluorine, CF ₃ or OR _f and R _f is CF ₃ , C ₂ F ₅ or C ₃ F ₇ ) Type. Representative fluoroolefins are tetrafluoroethylene, chlorotrifluoroethylene, hexafluoropropylene, and perfluoromethyl vinyl ether. The polyol may be linear or branched. Linear polyol is HOCH ₂ (CHOH) _x (CRR ') _y CH ₂ OH wherein R and R' are hydrogen or CH ₃ or C ₂ H ₅ , x is an integer from 0 to 4, y is 0 Lt; / RTI &gt; to 4). The branched polyol can be C (OH) _t (R) _u (CH ₂ OH) _v [(CH ₂ ) _m CH ₂ OH] _{w wherein} R can be hydrogen, CH ₃ or C ₂ H ₅ , m May be an integer from 0 to 3, t and u may be 0 or 1, v and w may be an integer from 0 to 4, and t + u + v + w is 4) . Representative polyols are trimethylol propane, pentaerythritol, butanediol, and ethylene glycol.

The 1,1,1-trifluoroalkane solubilizing agent of the present invention is a compound represented by the formula CF ₃ R ^{1 wherein} R ¹ is selected from aliphatic and alicyclic hydrocarbon radicals having about 5 to about 15 carbon atoms, Lt; / RTI &gt; is a primary linear saturated alkyl radical. Representative 1,1,1-trifluoroalkane solubilizers include, but are not limited to, 1,1,1-trifluorohexane and 1,1,1-trifluorododecane.

The solubilizing agent of the present invention may be present as a single compound or as a mixture of more than one solubilizing agent. The mixture of solubilizers may contain two solubilizing agents (e. G., Two lactones) from the same class of compounds or two solubilizing agents (e. G., Lactones and polyoxyalkylene glycol ethers) from different classes have.

In a composition of the present invention comprising a refrigerant and a UV fluorescent dye or comprising a heat transfer fluid and a UV fluorescent dye, about 0.001% to about 1.0%, preferably about 0.005% to about 0.5% Most preferably, 0.01% to about 0.25% by weight is a UV dye.

The solubility of these UV fluorescent dyes in refrigerant and heat transfer compositions may be low. Therefore, the method of introducing these dyes into a refrigeration, air conditioning, or heat pump apparatus is inconvenient, costly and time consuming. U.S. Patent RE 36,951, which is incorporated herein by reference, describes the use of dye powders, solid pellets or slurries of dyes that can be inserted into the components of a refrigeration or air conditioning apparatus. As the refrigerant and lubricant circulate through the apparatus, the dye is dissolved, dispersed, and moved throughout the apparatus. Many other methods of introducing dyes into refrigeration or air conditioning devices are described in the literature.

Ideally, no specialized method for introducing into the refrigeration, air conditioning, or heat pump system by the UV fluorescent dye being dissolved in the refrigerant may be required. The present invention relates to a composition comprising a UV fluorescent dye that is combined with a solubilizing agent and dissolved in a refrigerant to be introduced into the system. The compositions of the present invention enable the storage and transport of dye-containing refrigerants and heat transfer fluids while maintaining the dye in solution even at low temperatures.

In a composition of the present invention comprising a refrigerant, a UV fluorescent dye and a solubilizing agent or comprising a heat transfer fluid and a UV fluorescent dye and a solubilizer, about 1 to about 50 weight percent of the total composition, preferably about 2 to about 25 Wt.%, Most preferably from about 5 to about 15 wt.% Is a solubilizing agent in a refrigerant or heat transfer fluid. In the compositions of the present invention, the UV fluorescent dye is present in the refrigerant or heat transfer fluid at a level of from about 0.001 wt% to about 1.0 wt%, preferably from about 0.005 wt% to about 0.5 wt%, and most preferably from about 0.01 wt% to about 0.25 wt% &Lt; / RTI &gt;

Solubilizing agents such as ketones may have undesirable odors, which may be blocked by the addition of an odor control agent or fragrance. Typical examples of odor control agents or fragrances include Evergreen, Fresh Lemon, Cherry, Cinnamon, Peppermint, Floral or Orange Peel, Commercially available), as well as d-limonene and pinene. Such an odor control agent may be used at a concentration of about 0.001% to about 15% by weight based on the total weight of the odor control agent and the solubilizing agent.

The present invention also relates to a method of using a refrigerant or heat transfer fluid composition comprising an ultraviolet fluorescent dye to detect leakage in a refrigerating device, an air conditioning device, or a heating pump device. The presence of the dye in the composition enables detection of refrigerant leakage in refrigeration, air conditioning, or heat pump systems. Leak detection assists in ineffective operation of the device or system or / and / or troubleshooting, and / or prevention of equipment failure. Leak detection also helps contain the chemicals used in the operation of the device.

The method includes the steps of mixing a composition comprising a refrigerant, an ultraviolet fluorescent dye or a heat transfer fluid and a UV fluorescent dye, and optionally a solubilizing agent as described herein, as described herein, in a refrigeration, air conditioning, To the apparatus, and detecting the UV fluorescent dye-containing refrigerant using suitable means. Suitable means for detecting the dye include, but are not limited to, an ultraviolet lamp (often referred to as "black light" or "blue light"). These ultraviolet lamps are commercially available from many sources specifically designed for UV fluorescent dye detection. By introducing the ultraviolet fluorescent dye-containing composition into a refrigeration, air conditioning, or heat pump apparatus and circulating throughout the system, the ultraviolet lamp is turned on the apparatus and the fluorescence of the dye near any leak point is observed, You can set a nearby location.

Mechanical refrigeration is primarily an application of thermodynamics in which a cooling medium, such as refrigerant, travels through a cycle so that they can be recovered for reuse. Commonly used cycles include vapor-compression, absorption, vapor-jet or vapor-ejectors, and air.

A steam-compression refrigeration system includes an evaporator, a compressor, a condenser, and an expansion device. In a steam-compression cycle, refrigerants are reused in multiple stages, providing a cooling effect in one stage and a heating effect in another stage. The cycle can be briefly described as follows. Liquid refrigerant is introduced into the evaporator through the expansion device and the liquid refrigerant boils at low temperature in the evaporator to form the gas and provide cooling. A low pressure gas is introduced into the compressor, where the gas is compressed and its pressure and temperature rise. Subsequently, high pressure (compressed) gaseous refrigerant is introduced into the condenser, where the refrigerant condenses and its heat is vented to the surroundings. When the refrigerant returns to the expansion device, the liquid is expanded from the high pressure level in the condenser to the low pressure level in the evaporator, and thus the cycle is repeated.

There are various types of compressors available for refrigeration applications. The compressor is generally designed to operate in a reciprocal, rotary, jet, centrifugal, scroll, screw or axial flow type, depending on the mechanical means of compressing the fluid, For example, reciprocating, scroll, or screw type) or dynamic (e.g., centrifugal or jet type) compressors.

The compositions of the present invention comprising fluoroolefins may be useful in any of the compressor types described above. The choice of refrigerant for any given compressor depends on many factors, including, for example, boiling and vapor pressure requirements.

A positive displacement or a dynamic compressor can be used in the method of the present invention. For certain refrigerant compositions comprising one or more fluoroolefins, a centrifugal compressor is one preferred type of equipment.

In a centrifugal compressor, a rotating member is used to radially accelerate the refrigerant, which typically includes an impeller and a diffuser housed within the casing. Centrifugal compressors typically capture the fluid at the impeller eye, or at the central inlet of the circulating impeller, and radially accelerate it towards the outside. Some pressure rise occurs in the impeller, but most pressure rise occurs in the diffuser area of the casing where the velocity is converted to a static pressure. Each impeller-diffuser set is a step in the compressor. The centrifugal type compressor is composed of 1 to 12 or more steps depending on the desired final pressure and the volume of the refrigerant to be handled.

The pressure ratio or compression ratio of the compressor is the ratio of the absolute discharge pressure to the absolute inflow pressure. The pressure delivered by the centrifugal compressor is virtually constant over a relatively wide range of capacities.

The positive displacement compressor draws the vapor into the chamber, and the volume of the chamber is reduced to compress the vapor. After being compressed, the vapor is discharged from the chamber by further decreasing the volume of the chamber to zero or nearly zero. Positive displacement compressors can accumulate pressure, which is limited only by the volume efficiency and the strength of the part to withstand pressure.

Unlike a positive displacement compressor, the centrifugal compressor is entirely dependent on the centrifugal force of a high speed inlet pellicle that compresses the vapor passing through the impeller. There is no constant side, so-called dynamic-compression exists.

The pressure that can be generated by the centrifugal compressor depends on the tip speed of the impeller. The tip speed is its velocity measured at the tip of the impeller, which is related to the diameter of the impeller and its revolutions per minute. The capacity of the centrifugal compressor is determined by the size of the passage through the impeller. This makes the size of the compressor more dependent on the required pressure than the capacity.

Due to the high speed operation, the centrifugal compressor is basically a high volume, low pressure machine. Centrifugal compressors work best when using low pressure refrigerants such as trichlorofluoromethane (CFC-11) or 1,2,2-trichlorotrifluoroethane (CFC-113). Some of the low pressure refrigerant fluids of the present invention may be suitable as drop alternatives to CFC-113 in conventional centrifugal equipment.

Large centrifugal compressors typically operate at 3000 to 7000 rpm (revolutions per minute). Small turbine centrifugal compressors (mini-centrifugal compressors) are designed for high speeds from about 40,000 to about 70,000 (rpm), which typically have small impeller sizes of less than about 0.15 m (about 6 inches).

As multi-stage impellers are used in centrifugal compressors to improve compressor efficiency, lower power may be required in use. In a two-stage system, during operation, the discharge of the first stage impeller proceeds to the suction of the second impeller. Both impellers can be operated by the use of a single axis (axis or axle). Each step can constitute a compression ratio of about 4: 1; That is, the absolute discharge pressure may be four times the absolute suction pressure. Several examples of two-stage centrifugal compressor systems, particularly for automotive applications, are described in US 5,065,990 and US 5,363,674, both of which are incorporated herein by reference.

The disclosure of the present invention also encompasses,

(i) a fluoroolefin of the formula E or ZR ¹ CH = CHR ² , wherein R ¹ and R ² are independently a C ₁ to C ₆ perfluoroalkyl group;

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

(iii) -1- propene (CF ₃ CF = CHF) with 1,2,3,3,3- pentafluoropropane; 1-propene to 1,1,3,3,3-pentafluoropropane _{(CF 3 CH = CF 2)} ; 1,1,2,3,3-pentafluoro-1-propene (CHF ₂ CF = CF ₂ ); 1,2,3,3-tetrafluoro-1-propene (CHF ₂ CF = CHF); 2,3,3,3- tetrafluoro-1-propene with _{(CF 3 CF = CH 2)} ; 1,3,3,3- tetrafluoro-1-propene with (CF ₃ CH = CHF); 1,1,2,3-tetrafluoro-1-propene (CH ₂ FCF = CF ₂ ); 1,1,3,3-tetrafluoro-1-propene (CHF ₂ CH = CF ₂ ); 2,3,3-Trifluoro-1-propene (CHF ₂ CF = CH ₂ ); 1-propene, 3,3,3-trifluoromethyl _{(CF 3 CH = CH 2)} ; In 1,1,2-trifluoro-1-propene _{(CH 3 CF = CF 2)} ; 1,1,3-trifluoro-1-propene (CH ₂ FCH = CF ₂ ); 1,2,3-trifluoro-1-propene (CH ₂ FCF = CHF); 1,3,3-trifluoro-1-propene (CHF ₂ CH = CHF); 2-butene to 1,1,1,2,3,4,4,4- octafluoro _{(CF 3 CF = CFCF 3)} ; A 1,1,2,3,3,4,4,4- octafluoro-1-butene _{(CF 3 CF 2 CF = CF} 2); 2-butene to 1,1,1,2,4,4,4- heptafluoropropane _{(CF 3 CF = CHCF 3)} ; 1,2,3,3,4,4,4-heptafluoro-1-butene (CHF = CFCF ₂ CF ₃ ); 2-butene (CHF ₂ CF = CFCF ₃₎ a 1,1,1,2,3,4,4- heptafluoropropane; As 1,3,3,3- tetrafluoroethane (trifluoromethyl) -2-1-propene _{((CF 3) 2 C =} CHF); 1,1,3,3,4,4,4- heptafluoro-1-butene as a _{(CF 2 = CHCF 2 CF 3} ); 1,1,2,3,4,4,4- heptafluoro-1-butene as a (CF ₂ = CFCHFCF _3); A 1,1,2,3,3,4,4- heptafluoro-1-butene _{(CF 2 = CFCF 2 CHF 2} ); A 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 as a _{(CHF = CHCF 2 CF 3)} ; 1-butene (CHF = CFCHFCF ₃₎ a 1,2,3,4,4,4- hexafluoro; 1,2,3,3,4,4-hexafluoro-1-butene (CHF = CFCF ₂ CHF ₂ ); 1,1,2,3,4,4- hexafluoro-2-butene as a _{(CHF 2 CF = CFCHF 2)} ; 1,1,1,2,3,4-hexafluoro- ₂ -butene (CH ₂ FCF = CFCF ₃ ); 2-butene (CHF ₂ CH = CFCF ₃₎ a 1,1,1,2,4,4- hexafluoro; 1,1,1,3,4,4- hexafluoro-2-butene as a _{(CF 3 CH = CFCHF 2)} ; 1-butene _{(CF 2 = CFCF 2 CH 2} F) to 1,1,2,3,3,4- hexafluoro; 1,1,2,3,4,4- hexafluoro-1-butene as a (CF ₂ = CFCHFCHF _2); 3,3,3-trifluoro (trifluoromethyl) -2-propene-1 _{(CH 2 = C (CF 3} ) 2); A 1,1,1,2,4- pentafluoro-2-butene _{(CH 2 FCH = CFCF 3)} ; 1,1,1,3,4- pentafluoro-2-butene as a _{(CF 3 CH = CFCH 2 F} ); 3,3,4,4,4- pentafluoro-1-butene with _{(CF 3 CF 2 CH = CH} 2); 1,1,1,4,4- pentafluorophenyl-2-butene _{(CHF 2 CH = CHCF 3)} ; 2-butene (CH ₃ CF = CFCF ₃₎ with 1,1,1,2,3- pentafluoropropane; 2,3,3,4,4- pentafluorophenyl-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- pentafluorophenyl-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 pentafluoroethyl-2-methyl-1-propene _{(CF 2 = C (CF 3} ) (CH 3)); 2- (difluoro-methyl) -3,3,3-trifluoro-1-propene _{(CH 2 = C (CHF 2} ) (CF 3)); 1-butene (CH ₂ = CFCHFCF ₃₎ with 2,3,4,4,4- pentafluoropropane; 1,2,4,4,4- pentafluorophenyl-1-butene _{(CHF = CFCH 2 CF 3)} ; 1,3,4,4,4- pentafluorophenyl-1-butene (CHF = CHCHFCF _3); 1,3,3,4,4- pentafluoro-1-butene as a _{(CHF = CHCF 2 CHF 2)} ; 1,2,3,4,4- pentafluorophenyl-1-butene (CHF = CFCHFCHF _2); 1-butene as 3,3,4,4- tetrafluoroethane _{(CH 2 = CHCF 2 CHF 2} ); 1,1-di (difluoromethyl) -2-fluoro-1-propene _{(CF 2 = C (CHF 2} ) (CH 3)); 2-methyl-1-propene _{(CHF = C (CF 3)} (CH 3)) to 1,3,3,3- tetrafluoroethane; 2-difluoro-methyl-3,3-difluoro-1-propene _{(CH 2 = C (CHF 2} ) 2); 2-butene-1,1,1,2-tetrafluoroethane _{(CF 3 CF = CHCH 3)} ; 2-butene as 1,1,1,3- tetrafluoroethane (CF ₃ CH = CHCF _3); 1,1,1,2,3,4,4,5,5,5- to deca-fluoro-2-pentene _{(CF 3 CF = CFCF 2 CF} 3); 1,1,2,3,3,4,4,5,5,5- to deca-fluoro-1-pentene _{(CF 2 = CFCF 2 CF 2} CF 3); A 1,1,1,4,4,4- hexafluoro (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); A 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)} ; A 1,2,3,4,4,4- hexafluoro (trifluoromethyl) -3-butene _{(CHF = CFCF (CF 3)} 2); A 1,1,2,4,4,4- hexafluoro (trifluoromethyl) -3-butene-1 _{(CF 2 = CFCH (CF 3} ) 2); A 1,1,1,4,4,4- hexafluoro (trifluoromethyl) -2-butene _{(CF 3 CH = C (CF} 3) 2); A 1,1,3,4,4,4- hexafluoro (trifluoromethyl) -3-butene-1 _{(CF 2 = CHCF (CF 3} ) 2); A 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 ); With 3,3,4,4,4- pentafluoropropane (trifluoromethyl) -2-butene _{(CH 2 = C (CF 3} ) CF 2 CF 3); With 1,1,4,4,4- pentafluoropropane (trifluoromethyl) -3-butene-1 (CF = CHCH ₂ (CF _{3) 2);} With 1,3,4,4,4- pentafluoropropane (trifluoromethyl) -3-butene _{(CHF = CHCF (CF 3)} 2); With 1,1,4,4,4- pentafluoropropane (trifluoromethyl) -2-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 ); A 3,3,4,4,5,5,5- heptafluoro-1-pentene _{(CF 3 CF 2 CF 2 CH} = CH 2); A 2,3,3,4,4,5,5- heptafluoro-1-pentene _{(CH 2 = CFCF 2 CF 2} CHF 2); A 1,1,3,3,5,5,5- heptafluoro-1-butene _{(CF 2 = CHCF 2 CH 2} CF 3); 3-methyl-2-butene as a 1,1,1,2,4,4,4- heptafluoropropane _{(CF 3 CF = C (CF} 3) (CH 3)); As 2,4,4,4- tetrafluoroethane (trifluoromethyl) -3-butene _{(CH 2 = CFCH (CF 3} ) 2); As 1,4,4,4- tetrafluoroethane (trifluoromethyl) -3-butene _{(CHF = CHCH (CF 3)} 2); As 1,1,1,4- tetrafluoroethane (trifluoromethyl) -2-butene _{(CH 2 FCH = C (CF} 3) 2); As 1,1,1,3- tetrafluoroethane (trifluoromethyl) -2-butene _{(CH 3 CF = C (CF} 3) 2); 1,1,1-trifluoro (trifluoromethyl) -2-butene _{((CF 3) 2 C =} CHCH 3); A 3,4,4,5,5,5- hexafluoro-2-pentene _{(CF 3 CF 2 CF = CHCH} 3); A 1,1,1,4,4,4- hexafluoro-2-methyl-2-butene _{(CF 3 C (CH 3)} = CHCF 3); 1-pentene _{(CH 2 = CHCF 2 CHFCF 3} ) a 3,3,4,5,5,5- hexafluoro; 3- (trifluoro methyl) - 4,4,4-trifluoro-1-butene _{(CH 2 = C (CF 3} ) CH 2 CF 3); 1-hexene with 1,1,2,3,3,4,4,5,5,6,6,6- dodeca-fluoro _{(CF 3 (CF 2) 3} CF = CF 2); 3-hexene _{(CF 3 CF 2 CF = CFCF} 2 CF 3) in 1,1,1,2,2,3,4,5,5,6,6,6- dodeca-fluoro; A 1,1,1,4,4,4- hexafluoro (trifluoromethyl) -2,3-bis-2-butene _{((CF 3) 2 C =} C (CF 3) 2); A 1,1,1,2,3,4,5,5,5- nonafluoro -4- (trifluoromethyl) -2-pentene _{((CF 3) 2 CFCF =} CFCF 3); A 1,1,1,4,4,5,5,5- octafluoro -2- (trifluoromethyl) -2-pentene _{((CF 3) 2 C =} CHC 2 F 5); A 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 (trifluoromethyl) -3,3-bis-1-butene _{(CH 2 = CHC (CF 3} ) 3); (CF ₃ ) ₂ C = C (CH ₃ ) (CF ₃ )). ; (Trifluoromethyl) -4-2,3,3,5,5,5- hexafluoro-1-pentene _{(CH 2 = CFCF 2 CH (} CF 3) 2); 3-methyl-2-pentene as a 1,1,1,2,4,4,5,5,5- nonafluoro _{(CF 3 CF = C (CH} 3) CF 2 CF 3); (Trifluoromethyl) -4-1,1,1,5,5,5-hexafluoro-2-pentene _{(CF 3 CH = CHCH (CF} 3) 2); A 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- octafluoro-1-hexene _{(CH 2 = CHCF 2 CF 2} CF 2 CHF 2); A 1,1,1,4,4- pentafluoro -2- (trifluoromethyl) -2-pentene _{((CF 3) 2 C =} CHCF 2 CH 3); With 4,4,5,5,5- pentafluoropropane (trifluoromethyl) -2-pentene _{(CH 2 = C (CF 3} ) CH 2 C 2 F 5); 2-methyl-1-pentene as a 3,3,4,4,5,5,5- heptafluoropropane _{(CF 3 CF 2 CF 2 C} (CH 3) = CH 2); A 4,4,5,5,6,6,6- heptafluoro-2-hexene _{(CF 3 CF 2 CF 2 CH} = CHCH 3); A 4,4,5,5,6,6,6- heptafluoro-1-hexene _{(CH 2 = CHCH 2 CF 2} C 2 F 5); A 1,1,1,2,2,3,4- heptafluoro-3-hexene _{(CF 3 CF 2 CF = CFC} 2 H 5); Methyl-1-pentene-4-trifluoro-4,5,5,5- tetrafluoroethane _{(CH 2 = CHCH 2 CF (} CF 3) 2); 4-methyl-2-pentene to 1,1,1,2,5,5,5- heptafluoropropane _{(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- tetra deca fluoro-2-heptene as a _{(CF 3 CF = CFCF 2 CF} 2 C 2 F 5) ; _{(5 CF 3 CF 2 CF =} CFCF 2 C 2 F) 1,1,1,2,2,3,4,5,5,6,6,7,7,7- tetra deca fluoro-3-heptene ; 1,1,1,3,4,4,5,5,6,6,7,7,7- a tree deca-fluoro-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- a tree deca-fluoro-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- tree to deca-fluoro-3-heptene _{(CF 3 CF 2 CH = CFCF} 2 C 2 F 5); 1,1,1,2,2,3,5,5,6,6,7,7,7- tree to deca-fluoro-3-heptene _{(CF 3 CF 2 CF = CHCF} 2 C 2 F 5); _{CF 2 = CFOCF 2 CF 3 (} PEVE); CF ₂ = CFOCF ₃ (PMVE), and combinations thereof.

At least one fluoroolefin selected from the group consisting of: (a) a centrifugal compressor; (b) a multistage centrifugal compressor, or (c) a refrigerant, air conditioning or heating pump device having a single slab / single pass heat exchanger.

Methods of providing heating or cooling can be used in stationary air conditioning, heat pumps, or mobile air conditioning and refrigeration systems. Stationary air conditioning and heating pump applications include windows, ductless, ducted, packaged ends, coolers and commercial products (including packed roof ropes). Refrigeration applications include household refrigerators and freezers, ice makers, self-contained coolers and freezers, large coolers and freezers, and transport refrigeration systems.

The compositions of the present invention may also be used in air conditioning, heating and refrigeration systems where fin and tube heat exchangers, microchannel heat exchangers and vertical or horizontal single pass tubes or plate heat exchangers are used.

Conventional microchannel heat exchangers may not be ideal for the low pressure refrigerant composition of the present invention. Low operating pressures and densities result in high flow rates and high friction losses in all components. In these cases, the evaporator design can be modified. A single slab / single pass heat exchanger arrangement can be used rather than several microchannel slabs connected in series (for the refrigerant path). Thus, the preferred heat exchanger for the refrigerant or heat transfer fluid composition of the present invention is a single slab / single pass heat exchanger.

The present invention also relates to a method of providing cooling, comprising evaporating the fluoroolefin composition of the present invention in the vicinity of the object to be cooled, and then condensing the composition.

The present invention also relates to a method of providing heating, comprising condensing the fluoroolefin composition of the present invention in the vicinity of the object to be heated, and then evaporating the composition.

The present invention also provides a process for preparing a composition comprising compressing a composition comprising at least one fluoroolefin in a centrifugal compressor, condensing the composition, and then evaporating the composition in the vicinity of the object to be cooled &Lt; / RTI &gt; Further, the centrifugal type compressor of the method of the present invention may be a multi-stage centrifugal type compressor, preferably a two-stage centrifugal type compressor.

The present invention also relates to a refrigeration apparatus, an air conditioning apparatus, or a system comprising at least one single slab / single pass heat exchanger, comprising condensing the composition of the present invention and then evaporating said composition in the vicinity of the object to be cooled To a method of providing cooling to a heat pump apparatus.

The compositions of the present invention are particularly useful in small turbine centrifugal compressors (mini-centrifugal compressors) that can be used for automatic and window air conditioning, heat pumps, or transport refrigeration as well as other applications. These high efficiency mini-centrifugal compressors can be driven by an electric motor, and thus can be operated independently of the engine speed. A constant compressor speed allows the system to provide a relatively constant cooling capability at all engine speeds. This, in particular, provides an opportunity for increased efficiency at higher engine speeds as compared to conventional R-134a automotive air conditioning systems. Considering the cyclic operation of a conventional system at high drive speeds, the benefits of these low pressure systems become more apparent.

Alternatively, the mini-centrifugal compressor may be propelled by a scaled gear drive assembly having an engine exhaust gas powered turbine or a ratioed belt drive, rather than using power. Currently, the power available in automotive design is about 14 V, but a new mini-centrifugal compressor requires about 50 V of power. Therefore, the use of alternative power sources is advantageous. A refrigeration or air conditioning device driven by an engine exhaust gas powered turbine is described in detail in U.S. Patent Application No. 11 / 367,517, filed March 3, 2006. A refrigeration or air conditioning device driven by a scaled gear drive assembly is described in detail in U.S. Patent Application No. 11 / 378,832, filed March 17, 2006.

The present invention also relates to a method of compressing a composition of the present invention in a mini-centrifugal compressor driven by an engine exhaust gas powered turbine; Condensing said composition; And then evaporating said composition in the vicinity of the object to be cooled.

The present invention also relates to a method of compressing a composition of the present invention in a mini-centrifugal compressor driven by a scaled gear drive assembly having a scaled belt drive; Condensing said composition; And then evaporating said composition in the vicinity of the object to be cooled.

The present invention includes one or more single slab / single pass heat exchangers, including compressing a composition of the present invention in a centrifugal compressor, condensing the composition, and then evaporating the composition in the vicinity of the object to be cooled To an air conditioning device, or to a method of providing cooling in a heating pump device.

The present invention also relates to a method of replacing a refrigerant composition having a high GWP refrigerant or a GWP of at least about 150 with a composition having a lower GWP. One method includes providing a composition comprising one or more fluoroolefins of the present invention as alternatives. In another embodiment of the present invention, a refrigerant or heat transfer fluid composition of the present invention having a lower GWP relative to the composition to be substituted is introduced into the refrigeration, air conditioning or heat pump apparatus. In some cases, it may be necessary to remove the high GWP refrigerant present in the device from the device prior to introducing the lower GWP composition. In other cases, the fluoroolefin composition of the present invention may be introduced into the apparatus while the high GWP refrigerant is present.

Global Warming Potential Index (GWP) is an index that estimates relative global warming contribution due to atmospheric release of 1 kg of a particular greenhouse gas compared to a 1 kg release of carbon dioxide. The GWP can be calculated for different time ranges representing the effect of atmospheric lifetime on a given gas. Typically, the GWP for a time span of 100 years is a reference value.

High GWP refrigerants are any compound capable of functioning as a refrigerant or heat transfer fluid having a GWP of at least about 1000, alternatively of at least 500, at least 150, at least 100, or at least 50 in a time horizon of 100 years. Based on the GWP calculation method published by the Intergovernmental Panel on Climate Change (IPCC), refrigerant and heat transfer fluids that need to be replaced include HFC-134a (1,1,1, 2-tetrafluoroethane), but are not limited thereto

The present invention provides compositions with zero or low ozone depletion potential and low global warming potential (GWP). Mixtures of the fluoroolefins of the present invention or of the fluoroolefins of the present invention with other refrigerants have a lower global warming index than many of the hydrofluorocarbon refrigerants currently in use. Typically, the fluoroolefins of the present invention are expected to have a GWP of less than about 25. One aspect of the present invention is to provide a refrigerant having a global warming index of less than 1000, less than 500, less than 150, less than 100, or less than 50. [ Another aspect of the invention is to reduce the final GWP of the mixture by adding fluoroolefins to the refrigerant mixture.

The present invention also relates to a method of reducing the GWP of said refrigerant or heat transfer fluid, comprising combining a refrigerant or heat transfer fluid with one or more fluoroolefins of the present invention. In another embodiment, a method of reducing global warming index comprises combining said first composition with a composition comprising at least one fluoroolefin to produce a refrigerant or heat transfer fluid having a global warming index lower than said first composition Lt; RTI ID = 0.0 &gt; a &lt; / RTI &gt; It can be determined that the GWP of the mixture or combination of compounds can be calculated as the weighted average of the GWP for each of the pure compounds.

The present invention also relates to a process for preparing a second refrigerant or heat transfer fluid composition having a lower global warming index than the original refrigerant or heat transfer fluid composition by combining the original refrigerant or heat transfer fluid composition with a composition of the present invention comprising at least one fluoroolefin, Or a heat transfer fluid composition comprising at least one fluoroolefin to reduce the global warming index of the original refrigerant or heat transfer fluid composition.

The present invention is also directed to a refrigeration, air conditioning or heating device having a GWP of at least about 150, including introducing a second refrigerant or heat transfer fluid composition having a lower GWP of the present invention into a refrigeration, To a method of reducing the GWP of the original refrigerant or heat transfer fluid composition in a heat pump apparatus.

The method of the present invention for reducing the GWP of the original refrigerant can be accomplished by introducing the original refrigerant or heat transfer fluid composition from the refrigeration, air conditioning, or heat pump device prior to introducing a second refrigerant or heat transfer fluid with a lower GWP And &lt; / RTI &gt;

The present invention is also directed to a method of replacing an original refrigerant or heat transfer fluid composition with a second refrigerant or heat transfer fluid composition, including providing the composition of the present invention as a second refrigerant or heat transfer fluid composition. The original refrigerant may be any refrigerant used in a refrigeration, air conditioning or heating pump arrangement that needs to be replaced.

The original refrigerant or heat transfer fluid that needs to be replaced may be any of a hydrofluorocarbon refrigerant, a chlorofluorocarbon refrigerant, a hydrochlorofluorocarbon refrigerant, a fluoroether refrigerant, or a blend of refrigerant compounds.

The hydrofluorocarbon refrigerant of the present invention, which may need to be replaced,

But are not limited thereto. These hydrofluorocarbon refrigerants are either commercially available or can be prepared by methods known in the art.

The hydrofluorocarbon refrigerant of the present invention can be used in combination with azeotropic, azeotropic mixed-like and non-azeotropic mixed compositions such as HFC-125 / HFC-143a / HFC-134a (known as ASHRAE name R404 or R404A) / HFC-125 / HFC-134a (also known as ASHRAE designation R407 or R407A, R407B or R407C), HFC-32 / HFC-125 (R410 or R410A) (Blend of R134a / R218 / isobutane), R423A (blend of R134a / R227ea), R507A (blend of R125 / R143a), and the like.

Chlorofluorocarbons of the present invention that may need to be replaced carbon _{refrigerant, R22 (CHF 2 Cl),} R123 (CHCl 2 CF 3), R124 (CHClFCF 3), R502 (CFC-115 (CClF 2 CF 3) and and the like being of the blend R22), being a blend) of _{R503 (R23 / R13 (CClF 3} ).

The hydrochlorofluorocarbons of the present invention which may need to be replaced are selected from the group consisting of R 12 (CF ₂ Cl ₂ ), R 11 (CCl ₃ F), R 113 (CCl ₂ FCClF ₂ ), R 114 (CF ₂ ClCF ₂ Cl) Or R401B (a blend of R22 / R152a / R124), R408A (blend of R22 / R125 / R143a), and the like.

The fluoroether refrigerant of the present invention, which may need to be replaced, may include compounds that are similar to hydrofluorocarbons and also contain one or more ether group oxygen atoms. Fluoroether refrigerants include, but are not limited to, C ₄ F ₉ OCH ₃ and C ₄ F ₉ OC ₂ H ₅ , both of which are commercially available.

The original refrigerant or heat transfer fluid composition of the present invention that may need to be replaced may optionally contain up to 10% by weight of dimethyl ether, or one or more C ₃ to C ₅ hydrocarbons such as propane, propylene, cyclopropane , n-butane, isobutane, n-pentane, cyclopentane, and neopentane (2,2-dimethylpropane). Examples of such refrigerants containing C ₃ to C ₅ hydrocarbons are HCFC-22 / HFC-125 / propane (known as ASHRAE name R402 or R402A and R402B), HCFC-22 / octafluoropropane / propane HFC-134a / isobutane (also known as ASHRAE name R413 or R413A), HCFC-22 / HCFC-124 / HCFC-142b / isobutane (also known as ASHRAE name R414 (Known as R414A and R414B), HFC-134a / HCFC-124 / n-butane (known as ASHRAE name R416 or R416A), HFC-125 / HFC- 134a / n-butane (ASHRAE name R417 or R417A) HFC-134a / isobutane (also known as ASHRAE names R422, R422A, R422B, R422C, R422D), HFC-125 / HFC-134a / dimethyl ether (known as ASHRAE designation R419 or R419A) ) Of an azeotrope-like composition.

The present invention also provides a refrigeration system, air conditioner, or R134a (HFC-134a, ethanol 1,1,1,2-tetrafluoroethane, CF ₃ CH ₂ F) in the heat pump apparatus of the original refrigerant or heat transfer fluid The method of any one of the preceding claims, wherein the composition is replaced with a second refrigerant or heat transfer fluid composition comprising at least one compound selected from the group consisting of trifluoromethyltrifluoro vinyl ether (PMVE) To a method of replacing the composition.

The present invention also provides a refrigeration system, air conditioner, heat pump or the R152a (HFC-152a, 1,1-difluoro ethane, CHF ₂ CH _3), the original of the refrigerant or heat transfer fluid composition in the apparatus, E- 1,3,3,3-tetrafluoropropene (E-HFC-1234ze), 1,2,3,3,3-pentafluoropropene (HFC-1225ye), 2,3,3,3- At least one compound selected from the group consisting of tetrafluoropropene (HFC-1234yf), 3,3,3-trifluoropropene (HFC-1243zf), and trifluoromethyltrifluorovinyl ether (PMVE) To a second refrigerant or heat transfer fluid composition comprising a first refrigerant or a heat transfer fluid composition.

The present invention also relates to a process for the production of E-1,3,3,3-tetrafluoropropene (E-HFC-1234ze), 1,2,3,3,3-pentafluoropropene (HFC- , 3,3,3-tetrafluoropropene (HFC-1234yf), 3,3,3-trifluoropropene (HFC-1243zf), and trifluoromethyltrifluorovinyl ether (PMVE) (HFC-227ea, HFC-227ea, 1, 1, 1, 2, 3, 3, 4, 5 or 6) in a freezing apparatus, an air conditioner, or a heating pump apparatus, comprising providing a composition comprising at least one compound selected from the group 3-heptafluoropropane, CF ₃ CHFCF ₃ ).

The present invention also relates to a process for the preparation of 1,1,1,3,4,5,5,5-octafluoro-4- (trifluoromethyl) -2-butene (HFC-152-11mmyyz); 1,1,1,4,4,5,5,5-octafluoro-2- (trifluoromethyl) -2-pentene (HFC-152-11mmtz); 1,1,1,2,2,3,4,5,5,6,6,6-dodecafluoro-3-hexene (HFC-151-12mcy); 1,1,1,3-tetrafluoro-2-butene (HFC-1354mzy); 1,1,1,4,4,4-hexafluoro-2,3-bis (trifluoromethyl) -2-butene (HFC-151-12mmtt); 1,2,3,3,4,4,5,5,6,6-decafluorocyclohexene (FC-C151-10y); 3,3,4,4,5,5,5,5-heptafluoro-2-methyl-1-pentene (HFC-1567fts); 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene (PFBE); 4,4,5,5,6,6,6-heptafluoro-2-hexene (HFC-1567szz); 1,1,1,4,4,5,5,6,6,6-decafluoro-2-hexene (F13E); 1,1,1,2,3,4,5,5,5-nonafluoro-4- (trifluoromethyl) -2-pentene (HFC-151-12mmzz); And a second refrigerant or heat transfer fluid comprising at least one compound selected from the group consisting of 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (F22E) a composition comprising substituted, freezer, air conditioner, or heat pump R113 (-1,2,2- trifluoro CFC-113, 1,1,2-trichloro ethane in the apparatus, CFCl ₂ CF ₂ Cl) &lt; / RTI &gt; to the original refrigerant or heat transfer fluid composition.

The present invention also relates to a process for the preparation of 1,1,1,3,4,5,5,5-octafluoro-4- (trifluoromethyl) -2-butene (HFC-152-11mmyyz); 1,1,1,4,4,5,5,5-octafluoro-2- (trifluoromethyl) -2-pentene (HFC-152-11mmtz); 1,1,1,2,2,3,4,5,5,6,6,6-dodecafluoro-3-hexene (HFC-151-12mcy); 1,1,1,3-tetrafluoro-2-butene (HFC-1354mzy); 1,1,1,4,4,4-hexafluoro-2,3-bis (trifluoromethyl) -2-butene (HFC-151-12mmtt); 1,2,3,3,4,4,5,5,6,6-decafluorocyclohexene (FC-C151-10y); 3,3,4,4,5,5,5,5-heptafluoro-2-methyl-1-pentene (HFC-1567fts); 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene (PFBE); 4,4,5,5,6,6,6-heptafluoro-2-hexene (HFC-1567szz); 1,1,1,4,4,5,5,6,6,6-decafluoro-2-hexene (F13E); 1,1,1,2,3,4,5,5,5-nonafluoro-4- (trifluoromethyl) -2-pentene (HFC-151-12mmzz); And a second refrigerant or heat transfer fluid comprising at least one compound selected from the group consisting of 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (F22E) R43-10mee (HFC-43-10mee, 1,1,1,2,3,4,4,5,5,5-hexafluoropropane) in a refrigerating apparatus, an air conditioning apparatus, or a heating pump apparatus, pentane as deca fluoro, CF ₃ CHFCHFCF ₂ CF ₃₎ which relates to the original method of replacing the refrigerant or heat transfer fluid composition.

The present invention also relates to a process for the preparation of 1,1,1,3,4,5,5,5-octafluoro-4- (trifluoromethyl) -2-butene (HFC-152-11mmyyz); 1,1,1,4,4,5,5,5-octafluoro-2- (trifluoromethyl) -2-pentene (HFC-152-11mmtz); 1,1,1,2,2,3,4,5,5,6,6,6-dodecafluoro-3-hexene (HFC-151-12mcy); 1,1,1,3-tetrafluoro-2-butene (HFC-1354mzy); 1,1,1,4,4,4-hexafluoro-2,3-bis (trifluoromethyl) -2-butene (HFC-151-12mmtt); 1,2,3,3,4,4,5,5,6,6-decafluorocyclohexene (FC-C151-10y); 3,3,4,4,5,5,5,5-heptafluoro-2-methyl-1-pentene (HFC-1567fts); 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene (PFBE); 4,4,5,5,6,6,6-heptafluoro-2-hexene (HFC-1567szz); 1,1,1,4,4,5,5,6,6,6-decafluoro-2-hexene (F13E); 1,1,1,2,3,4,5,5,5-nonafluoro-4- (trifluoromethyl) -2-pentene (HFC-151-12mmzz); And a second refrigerant or heat transfer fluid comprising at least one compound selected from the group consisting of 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (F22E) Heat-transfer fluid composition that is C ₄ F ₉ OCH ₃ (perfluorobutyl methyl ether) in a refrigerating device, an air-conditioning device, or a heat pump device, .

The present invention also relates to a process for the preparation of 1,1,1,3,4,5,5,5-octafluoro-4- (trifluoromethyl) -2-butene (HFC-152-11mmyyz); 1,1,1,4,4,5,5,5-octafluoro-2- (trifluoromethyl) -2-pentene (HFC-152-11mmtz); 1,1,1,2,2,3,4,5,5,6,6,6-dodecafluoro-3-hexene (HFC-151-12mcy); 1,1,1,3-tetrafluoro-2-butene (HFC-1354mzy); 1,1,1,4,4,4-hexafluoro-2,3-bis (trifluoromethyl) -2-butene (HFC-151-12mmtt); 1,2,3,3,4,4,5,5,6,6-decafluorocyclohexene (FC-C151-10y); 3,3,4,4,5,5,5,5-heptafluoro-2-methyl-1-pentene (HFC-1567fts); 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene (PFBE); 4,4,5,5,6,6,6-heptafluoro-2-hexene (HFC-1567szz); 1,1,1,4,4,5,5,6,6,6-decafluoro-2-hexene (F13E); 1,1,1,2,3,4,5,5,5-nonafluoro-4- (trifluoromethyl) -2-pentene (HFC-151-12mmzz); And a second refrigerant or heat transfer fluid comprising at least one compound selected from the group consisting of 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (F22E) which comprises substitution of a composition, R365mfc in the freezer, air conditioner, or heat pump apparatus (butane as HFC-365mfc, 1,1,1,3,3- _{pentafluoropropane, CF 3 CH 2 CF 2 CH} 3) Lt; RTI ID = 0.0 &gt; refrigerant or heat transfer fluid composition. &Lt; / RTI &gt;

The present invention also relates to a process for preparing 1,2,3,3,4,4,5,5-octafluorocyclopentene (FC-C1418y); 1,1,1,2,3,4,4,5,5,5-decafluoro-2-pentene (FC-141-10myy); 1,1,1,2,4,4,5,5,5-nonafluoro-2-pentene (HFC-1429myz); 1,1,1,3,4,4,5,5,5-nonafluoro-2-pentene (HFC-1429mzy); 3,3,4,4,5,5,5,5-heptafluoro-1-pentene (HFC-1447fz); 1,1,1,4,4,4-hexafluoro-2-butene (F11E); 1,1,1,4,4,4-hexafluoro-2- (trifluoromethyl) -2-butene (HFC-1429mzt); And a second refrigerant or heat transfer fluid composition comprising at least one compound selected from the group consisting of 1,1,1,4,4,5,5,5-octafluoro-2-pentene (F12E) (CFC-11, trichlorofluoromethane, CFCl ₃ ) in a refrigerating device, an air-conditioning device, or a heating pump device,

The present invention also relates to a process for preparing 1,2,3,3,4,4,5,5-octafluorocyclopentene (FC-C1418y); 1,1,1,2,3,4,4,5,5,5-decafluoro-2-pentene (FC-141-10myy); 1,1,1,2,4,4,5,5,5-nonafluoro-2-pentene (HFC-1429myz); 1,1,1,3,4,4,5,5,5-nonafluoro-2-pentene (HFC-1429mzy); 3,3,4,4,5,5,5,5-heptafluoro-1-pentene (HFC-1447fz); 1,1,1,4,4,4-hexafluoro-2-butene (F11E); 1,1,1,4,4,4-hexafluoro-2- (trifluoromethyl) -2-butene (HFC-1429mzt); And a second refrigerant or heat transfer fluid composition comprising at least one compound selected from the group consisting of 1,1,1,4,4,5,5,5-octafluoro-2-pentene (F12E) (HCFC-123, 2,2-dichloro-1,1,1-trifluoroethane, CF ₃ CHCl ₂ ) in a refrigerating device, an air conditioning device or a heating pump device, To a method of replacing a transfer fluid composition.

The present invention also relates to a process for the preparation of 2,3,3-trifluoropropene (HFC-1243yf); 1,1,1,4,4,4-hexafluoro-2-butene (F11E); 1,3,3,3-tetrafluoropropene (HFC-1234ze); 1,1,1,2,4,4,4-heptafluoro-2-butene (HFC-1327my); 1,2,3,3-tetrafluoropropene (HFC-1234ye); And a second refrigerant or heat transfer fluid composition comprising at least one compound selected from the group consisting of pentafluoroethyl trifluorovinyl ether (PEVE) and pentafluoroethyl trifluorovinyl ether (PEVE). (HFC-245fa, 1,1,1,3,3-pentafluoropropane, CF ₃ CH ₂ CHF ₂ ) in the apparatus.

The present invention is also directed to 1,1,1,2,3,4,4,4-octafluoro-2-butene (FC-1318my); 1,2,3,3,4,4-hexafluorocyclobutene (FC-C1316cc); 2,3,3,4,4,4-hexafluoro-1-butene (HFC-1336yf); And a second refrigerant or heat transfer fluid composition comprising at least one compound selected from the group consisting of 3,3,4,4,4-pentafluoro-1-butene (HFC-1345fz). freezer, air conditioner, or heat pump apparatus in the R114 (CFC-114, 1,2- dichloro-tetrafluoro-ethane in -1,1,2,2-, CFCl ₂ CF ₂ Cl) in the original refrigerant or heat transfer To a method of replacing a fluid composition.

The present invention is also directed to 1,1,1,2,3,4,4,4-octafluoro-2-butene (FC-1318my); 1,2,3,3,4,4-hexafluorocyclobutene (FC-C1316cc); 2,3,3,4,4,4-hexafluoro-1-butene (HFC-1336yf); And a second refrigerant or heat transfer fluid composition comprising at least one compound selected from the group consisting of 3,3,4,4,4-pentafluoro-1-butene (HFC-1345fz). (as HFC-236fa, 1,1,1,3,3,3- _{hexafluoropropane, CF 3 CH 2 CF 3)} R236fa in the freezer, air conditioner, or heat pump apparatus, the original of the refrigerant or heat transfer fluid To a method of replacing the composition.

The present invention relates to a process for producing E-1,3,3,3-tetrafluoropropene (E-HFC-1234ze); 1,2,3,3,3-pentafluoropropene (HFC-1225ye); 2,3,3,3-tetrafluoropropene (HFC-1234yf); 3,3,3-trifluoropropene (HFC-1243zf); And a second refrigerant or heat transfer fluid composition comprising at least one compound selected from the group consisting of trifluoromethyl trifluorovinyl ether (PMVE) and trifluoromethyl trifluorovinyl ether (PMVE). To a method of replacing the original refrigerant or heat transfer fluid composition that is R401A in the apparatus. R401A contains about 53 wt% HCFC-22 (chlorodifluoromethane, CHF ₂ Cl), about 13 wt% HFC-152a (1,1-difluoroethane, CHF ₂ CH ₃ ) ASHRAE designation for a refrigerant blend containing (ethane, CF ₃ CHClF 2-chloro -1,1,1,2- tetrafluoroethane)% by weight of HCFC-124.

The present invention is also directed to a process for the preparation of E-1,3,3,3-tetrafluoropropene (E-HFC-1234ze); 1,2,3,3,3-pentafluoropropene (HFC-1225ye); 2,3,3,3-tetrafluoropropene (HFC-1234yf); 3,3,3-trifluoropropene (HFC-1243zf); And a second refrigerant or heat transfer fluid composition comprising at least one compound selected from the group consisting of trifluoromethyl trifluorovinyl ether (PMVE) and trifluoromethyl trifluorovinyl ether (PMVE). &Lt; RTI ID = 0.0 &gt; R401B &lt; / RTI &gt; in the apparatus. R401B contains about 61 wt% HCFC-22 (chlorodifluoromethane, CHF ₂ Cl), about 11 wt% HFC-152a (1,1-difluoroethane, CHF ₂ CH ₃ ) ASHRAE designation for a refrigerant blend containing (ethane, CF ₃ CHClF 2-chloro -1,1,1,2- tetrafluoroethane)% by weight of HCFC-124.

The present invention is also directed to a process for the preparation of E-1,3,3,3-tetrafluoropropene (E-HFC-1234ze); 1,2,3,3,3-pentafluoropropene (HFC-1225ye); 2,3,3,3-tetrafluoropropene (HFC-1234yf); 3,3,3-trifluoropropene (HFC-1243zf); And a second refrigerant or heat transfer fluid composition comprising at least one compound selected from the group consisting of trifluoromethyl trifluorovinyl ether (PMVE) and trifluoromethyl trifluorovinyl ether (PMVE). To a method of replacing the original refrigerant or heat transfer fluid composition that is R409A in the apparatus. R409A contains about 60 wt% HCFC-22 (chlorodifluoromethane, CHF ₂ Cl), about 25 wt% HCFC-124 (2-chloro-1,1,1,2-tetrafluoroethane, CF ₃ CHClF), and about 15 wt% HCFC-142b (1-chloro-1,1-difluoroethane, CF ₂ ClCH ₃ ).

The present invention is also directed to a process for the preparation of E-1,3,3,3-tetrafluoropropene (E-HFC-1234ze); 1,2,3,3,3-pentafluoropropene (HFC-1225ye); 2,3,3,3-tetrafluoropropene (HFC-1234yf); 3,3,3-trifluoropropene (HFC-1243zf); And a second refrigerant or heat transfer fluid composition comprising at least one compound selected from the group consisting of trifluoromethyl trifluorovinyl ether (PMVE) and trifluoromethyl trifluorovinyl ether (PMVE). &Lt; RTI ID = 0.0 &gt; R409B &lt; / RTI &gt; in the device. R409B contains about 65 wt% HCFC-22 (chlorodifluoromethane, CHF ₂ Cl), about 25 wt% HCFC-124 (2-chloro-1,1,1,2-tetrafluoroethane, CF ₃ CHClf), and about 10 wt% HCFC-142b (1-chloro-1,1-difluoroethane, CF ₂ ClCH ₃ ).

The present invention also relates to a process for the production of E-1,3,3,3-tetrafluoropropene (E-HFC-1234ze), 1,2,3,3,3-pentafluoropropene (HFC- , 3,3,3-tetrafluoropropene (HFC-1234yf), 3,3,3-trifluoropropene (HFC-1243zf), and trifluoromethyltrifluorovinyl ether (PMVE) Replacing the original refrigerant or heat transfer fluid composition that is R414B in a refrigerating device, air conditioning device, or heat pump device, including replacing it with a second refrigerant or heat transfer fluid composition comprising at least one compound selected from the group &Lt; / RTI &gt; R414B contains about 50 wt% HCFC-22 (chlorodifluoromethane, CHF ₂ Cl), about 39 wt% HCFC-124 (2-chloro-1,1,1,2-tetrafluoroethane, CF ₃ CHClF), about 1.5% by weight isobutane _{(R600a, CH 3 CH (CH} 3) CH 3), and from about 9.5% by weight of HCFC-142b (1-chloro-1,1-difluoro ethane as a, CF ₂ ClCH ₃ ) &lt; / RTI &gt; for the refrigerant blend.

The present invention is also directed to a process for the preparation of E-1,3,3,3-tetrafluoropropene (E-HFC-1234ze); 1,2,3,3,3-pentafluoropropene (HFC-1225ye); 2,3,3,3-tetrafluoropropene (HFC-1234yf); 3,3,3-trifluoropropene (HFC-1243zf); And a second refrigerant or heat transfer fluid composition comprising at least one compound selected from the group consisting of trifluoromethyl trifluorovinyl ether (PMVE) and trifluoromethyl trifluorovinyl ether (PMVE). Lt; RTI ID = 0.0 &gt; R416A &lt; / RTI &gt; in the device. R416A is, _{(1,1,1,2-tetrafluoro-ethane, CF 3 CH 2 F) HFC} -134a of about 59% by weight), HCFC-124 of from about 39.5% by weight of (2-chloro -1,1, in 1, 2-tetrafluoro-ethane, CF ₃ CHClF), and the ASHRAE designation for a refrigerant blend containing n- butane _{(CH 3 CH 2 CH 2 CH} 3) from about 1.5% by weight.

The present invention also relates to a process for preparing 1,2,3,3,3-pentafluoropropene (HFC-1225ye); 2,3,3,3-tetrafluoropropene (HFC-1234yf); 3,3,3-trifluoropropene (HFC-1243zf); And a second refrigerant or heat transfer fluid composition comprising at least one compound selected from the group consisting of trifluoromethyl trifluorovinyl ether (PMVE) and trifluoromethyl trifluorovinyl ether (PMVE). (CFC-12, dichlorodifluoromethane, CF ₂ Cl ₂ ) in the apparatus to replace the original refrigerant or heat transfer fluid composition.

The present invention also relates to a process for preparing 1,2,3,3,3-pentafluoropropene (HFC-1225ye); 2,3,3,3-tetrafluoropropene (HFC-1234yf); 3,3,3-trifluoropropene (HFC-1243zf); And a second refrigerant or heat transfer fluid composition comprising at least one compound selected from the group consisting of trifluoromethyl trifluorovinyl ether (PMVE) and trifluoromethyl trifluorovinyl ether (PMVE). Lt; RTI ID = 0.0 &gt; R500 &lt; / RTI &gt; in the device. R500 is, approximately 73.8% of R12 ((CFC-12, weight-dichloro difluoro methane, CF ₂ Cl _2), and about 26.2 wt% R152a (HFC-152a, the ethane to 1,1-di-fluoro, CHF ₂ CH ₃ ) &lt; / RTI &gt; for the azeotropic mixed refrigerant blend.

The present invention is directed to a process for the production of a refrigerant or heat transfer fluid composition comprising an original refrigerant or heat transfer fluid composition that is R134a or R12 from about 1.0 wt% to about 37 wt% HFC-32 and from about 99 wt% to about 63 wt% Or a heat transfer fluid composition, in which the heat transfer fluid composition is replaced. In another embodiment, the second refrigerant or heat transfer fluid composition may comprise from about 1.0 wt% to about 10 wt% HFC-32 and from about 99 wt% to about 90 wt% HFC-1225ye.

The present invention is directed to a process for the preparation of a composition comprising an original refrigerant or heat transfer fluid composition that is R22, R404A or R410A in an amount of from about 1.0% to about 37% by weight HFC-32 and from about 99% 2 &lt; / RTI &gt; refrigerant or heat transfer fluid composition for a refrigerant or heat transfer fluid composition. In another embodiment, the second refrigerant or heat transfer fluid composition may comprise from about 20 wt% to about 37 wt% HFC-32 and from about 80 wt% to about 63 wt% HFC-1225ye.

The present invention also relates to a process for the manufacture of a refrigerant or heat transfer fluid composition comprising R20, R404A or R410A from about 20 wt% to about 95 wt% HFC-1225ye, from about 1.0 wt% to about 65 wt% HFC- To a second refrigerant or heat transfer fluid composition comprising from about 1.0% to about 40% by weight of HFC-125. In another embodiment, the second refrigerant or heat transfer fluid composition comprises from about 30 wt% to about 90 wt% HFC-1225ye, from about 5.0 wt% to about 55 wt% HFC-32, and from about 1.0 wt% 35% by weight HFC-125. In another embodiment, the second refrigerant or heat transfer fluid composition comprises from about 40 wt% to about 85 wt% HFC-1225ye, from about 10 wt% to about 45 wt% HFC-32, and from about 1.0 wt% By weight of HFC-125.

The present invention relates to a process for the preparation of a refrigerant or heat transfer fluid composition comprising R134a or R12,

HFC-1243zf and HFC-1225ye;

HFC-1243zf, HFC-1225ye, and HFC-125;

HFC-1243zf, HFC-1225ye, and HFC-32; or

HFC-1243zf, HFC-1225ye, HFC-125, and HFC-32

And a method of replacing said original refrigerant or heat transfer fluid composition, wherein said second refrigerant or heat transfer fluid composition is replaced by a second refrigerant or heat transfer fluid composition comprising said second refrigerant or heat transfer fluid composition.

In all of the above refrigerant replacement methods, fluoroolefins can be used to replace refrigerants in existing equipment. In addition, fluoroolefins can be used to replace such refrigerants in existing equipment designed for use with certain refrigerants. In addition, fluoroolefins can be used to replace refrigerants in existing equipment without the need to change or replace the lubricant.

The present invention is directed to a method of reducing fire risk in a refrigeration apparatus, an air conditioning apparatus, or a heating pump apparatus, comprising introducing the composition of the present invention into a refrigerant apparatus or air conditioning apparatus.

Considering the flammability, the refrigerant, the air conditioner, or the refrigerant that can leak from the heat pump device becomes a serious problem. If leaks occur in the refrigeration or air conditioning system, refrigerant and potentially a small amount of lubricant may be released from the system. If this leakage material comes into contact with the ignition source, a fire may occur. A fire hazard means the possibility of a fire occurring in or near a freezer, air conditioner, or heat pump unit. Reducing the fire risk in a refrigeration unit, air conditioning unit, or heat pump unit can be achieved by using a refrigerant or heat transfer fluid that is not considered flammable when measured and defined by the methods and standards described herein have. In addition, the non-flammable fluoroolefins of the present invention may be added to a flammable refrigerant or heat transfer fluid already present in the apparatus or before being added to the apparatus. The non-combustible fluoroolefins of the present invention reduce fire risk by reducing the probability of a fire in the event of a leak and / or reducing the temperature or size of any flames generated.

The present invention is also directed to a refrigerating apparatus, an air conditioning apparatus, a refrigeration system, a refrigeration system, an air conditioning system, a refrigeration system, a refrigeration system, , Or a method of reducing fire risk in or near a heat pump apparatus.

The present invention also relates to a process for the preparation of a refrigerating device, comprising combining a lubricant with at least one non-flammable fluoroolefin, and introducing the combination into a refrigerating device, an air conditioning device, , An air conditioning device, or a method of reducing fire risk in or near a heating pump device.

The present invention is also directed to a method of reducing fire risk in or near the apparatus, comprising introducing one or more fluoroolefins into a freezer, an air conditioner, or a heat pump apparatus.

The present invention also relates to a method of using said flammable refrigerant in a refrigeration apparatus, an air conditioning apparatus, or a heating pump apparatus, comprising combining a flammable refrigerant and at least one fluoroolefin.

The present invention is also directed to a method for reducing the flammability of said flammable refrigerant or heat transfer fluid, comprising combining a flammable refrigerant and at least one fluoroolefin.

The present invention is also directed to a method of delivering heat from a heat source to a heat sink, the composition of the present invention being supplied as a heat transfer fluid. The heat transfer method comprises transporting the composition of the present invention from a heat source to a heat sink.

Heat transfer fluids are used to transfer, transfer, or remove heat from one space, location, object, or object to a different space, location, object, or object by radiation, conduction, or convection. The heat transfer fluid may function as a second coolant by providing a means of delivery for cooling (or heating) from a far-frozen (or heated) system. In some systems, the heat transfer fluid may remain constant (i.e., not evaporated or condensed) throughout the transfer process. Alternatively, heat transfer fluids can also be used in the evaporative cooling process.

A heat source may be defined as any space, position, object, or object where it is desirable to transfer, move, or remove heat therefrom. An example of a heat source may be a space in which refrigeration or cooling is required (open or enclosed), such as a refrigerator or freezer case in a supermarket, a building space where air conditioning is required, or a passenger compartment of an automobile that requires air conditioning. A heat sink can be defined as any space, position, object, or object capable of absorbing heat. A vapor compression refrigeration system is an example of such a heat sink.

<Examples>

Example 1

Performance data

The following table 7 shows the pressure and discharge temperatures in the evaporator (Evap) and the condenser (Cond) for the compounds of the present invention compared to CFC-113, HFC-43-10mee, C ₄ F ₉ OCH ₃ and HFC- Disch T), energy efficiency (COP) and capacity (Cap). The data are based on the following conditions.

Evaporator temperature 40.0 ℉ (4.4 캜)

Condenser temperature 110.0 ℉ (43.3 캜)

The subcool temperature was 10.0 ((5.5 캜)

Recovery gas temperature 75.0 ((23.8 캜)

Compressor Efficiency 70%

Example 2

Performance data

Table 8 below shows the pressure, the discharge temperature (Disch T), the energy efficiency (COP) and the capacity (Cap) in the evaporator (Evap) and the condenser (Cond) for the compounds of the present invention compared to CFC-11 and HCFC- ). The data are based on the following conditions.

Evaporator temperature 40.0 ℉ (4.4 캜)

Condenser temperature 110.0 ℉ (43.3 캜)

Supercooling temperature of 10.0 ℉ (5.5 캜)

Recovery gas temperature 75.0 ((23.8 캜)

Compressor Efficiency 70%

Example 3

Performance data

Table 9 below shows the refrigeration performance as the pressure, the discharge temperature (Disch T), the energy efficiency (COP) and the capacity (Cap) in the evaporator (Evap) and the condenser (Cond) for the compound of the present invention as compared with HFC- Respectively. The data are based on the following conditions.

Evaporator temperature 40.0 ℉ (4.4 캜)

Condenser temperature 110.0 ℉ (43.3 캜)

Supercooling temperature of 10.0 ℉ (5.5 캜)

Recovery gas temperature 75.0 ((23.8 캜)

Compressor Efficiency 70%

Example 4

Performance data

In Table 10, the pressure, the discharge temperature (Disch T), the energy efficiency (COP) and the capacity (Cap) in the evaporator (Evap) and the condenser (Cond) for the compound of the present invention as compared to CFC-114 and HFC- ). The data are based on the following conditions.

Evaporator temperature 40.0 ℉ (4.4 캜)

Condenser temperature 110.0 ℉ (43.3 캜)

Supercooling temperature of 10.0 ℉ (5.5 캜)

Recovery gas temperature 75.0 ((23.8 캜)

Compressor Efficiency 70%

Example 5

Performance data

In Table 11, the pressure, the discharge temperature (Disch T), the energy efficiency (COP) in the evaporator (Evap) and the condenser (Cond) for the compound of the present invention as compared with HFC-134a, HFC- 152a and HFC- And capacity (Cap). The data are based on the following conditions.

Evaporator temperature 40.0 ℉ (4.4 캜)

Condenser temperature 110.0 ℉ (43.3 캜)

Supercooling temperature of 10.0 ℉ (5.5 캜)

Recovery gas temperature 75.0 ((23.8 캜)

Compressor Efficiency 70%

Example 6

Flammability

Combustible compounds can be identified by testing under the American Society of Testing and Materials (ASTM) E681-01 using an electronic ignition source. This flammability test is performed on the composition of the present disclosure at various concentrations in the air at 101 kPa (14.7 psia), 50% relative humidity and at the specified temperature to determine if it is flammable and, if flammable, Respectively. The results are shown in Table 12 below.

The results show that HFC-1234yf and E-HFC-1234ze are flammable and HFC-1225ye, HFC-1429myz / mzy and F12E are non-flammable. For a mixture of HFC-1225ye and HFC-32 (which is known to be flammable in pure state), it was determined that 37 wt% HFC-32 is the maximum amount that can be present to maintain non-flammability characteristics. Compositions comprising non-flammable fluoroolefins are a more acceptable candidate material as a refrigerant or heat transfer fluid composition.

Example 7

Tip speed for pressure rise

The tip speed can be estimated by obtaining some basic relationship to the refrigeration equipment in which the centrifugal compressor is used. The torque which the impeller ideally gives to the gas is defined by the following equation (1).

Wherein,

T = torque (N-m)

m = mass flow rate (kg / s)

v ₂ = tangential velocity (tip speed) of refrigerant discharged from the impeller (m / s)

r ₂ = radius of impeller outlet (m)

v ₁ = tangential velocity of the refrigerant introduced into the impeller (m / s)

r ₁ = radius of impeller inlet (m).

Assuming that the refrigerant is essentially introduced into the impeller in the axial direction, the tangential component of velocity, v ₁ = 0, is given by: &quot; (2) &quot;

The power required on the shaft is the product of torque and rotational speed.

Wherein,

P = power (W)

ω = angular velocity (rad / s).

Therefore, the following equation (4) is obtained.

At low refrigerant flow velocities, the tip speed of the impeller and the tangential velocity of the refrigerant are approximately equal,

Another equation for ideal power is the product of the mass flow rate and the isentropy of compression.

Wherein,

H _i is the enthalpy difference (kJ / kg) of the refrigerant from the saturated vapor to the saturated condensing condition in the evaporation condition.

When Equations (6) and (7) are combined, the following Equation (8) is obtained.

Although equation (8) is based on some basic assumptions, it provides a satisfactory estimate of the impeller tip velocity and provides an important way to compare the tip velocity of the refrigerant.

The theoretical tip speeds calculated for 1,2,2-trichlorotrifluoroethane (CFC-113) and compositions of the present invention are shown in Table 13 below. The assumed conditions for this comparison are as follows.

Evaporator temperature 40.0 ℉ (4.4 캜)

Condenser temperature 110.0 ℉ (43.3 캜)

Liquid supercooling temperature 10.0 ℉ (5.5 캜)

Recovery gas temperature 75.0 ((23.8 캜)

Compressor Efficiency 70%

These are typical conditions in which small turbine centrifugal compressors are operated.

This example shows that the compounds of the present invention have an end velocity within about 15% of CFC-113 and are an effective alternative to CFC-113 while minimizing compressor design. The most preferred composition has a tip speed within about 10% of CFC-113.

Example 8

Refrigeration performance data

Table 14 below shows the performance of various refrigerant compositions of the present invention as compared to HFC-134a. In Table 14, "Evap pressure" is the evaporator pressure, "Cond pressure" is the condenser pressure, "Comp Disch T" is the compressor discharge temperature, "COP" is the energy efficiency, and "CAP" is the capacity. The data are based on the following conditions.

Evaporator temperature 40.0 ℉ (4.4 캜)

Condenser temperature 130.0 ℉ (54.4 캜)

Supercooling amount 10.0 ℉ (5.5 캜)

Recovery gas temperature 60.0 ((15.6 캜)

Compressor Efficiency 100%

It is noted that the cooling capacity includes overheating.

Several compositions had much higher energy efficiency (COP) while maintaining a lower or equal discharge pressure and temperature compared to HFC-134a. The capacity of the compositions listed in Table 14 was also similar to R134a, indicating that these compositions could be alternative refrigerants for R134a in refrigeration and air conditioning applications, especially in mobile air conditioning applications. The results also show that the cooling capacity of HFC-1225ye can be improved by the addition of other compounds such as HFC-32.

Example 9

Refrigeration performance data

Table 15 below shows the performance of various refrigerant compositions of the present invention as compared to R404A and R422A. In Table 15, "Evap pressure" is the evaporator pressure, "Cond pressure" is the condenser pressure, "Comp Disch T" is the compressor discharge temperature, "EER" is the energy efficiency, and "CAP" is the capacity. The data are based on the following conditions.

Evaporator temperature -17.8 ℃

Condenser temperature 46.1 ℃

Supercooling amount 5.5 ℃

Recovery gas temperature 15.6 ℃

Compressor Efficiency 70%

It is noted that the cooling capacity includes overheating.

Several compositions have high energy efficiency (EER) comparable to R404A and R422A. The discharge temperature was also lower than R404A and R507A. The capacity of the compositions shown in Table 15 was also similar to R404A, R507A and R422A, indicating that these compositions could be alternative refrigerants for R404A, R507A or R422A in refrigeration and air conditioning.

Example 10

Refrigeration performance data

Table 16 below shows the performance of various refrigerant compositions of the present invention as compared to HCFC-22 and R410A. In Table 16, "Evap pressure" is the evaporator pressure, "Cond pressure" is the condenser pressure, "Comp Disch T" is the compressor discharge temperature, "EER" is the energy efficiency, and "CAP" is the capacity. The data are based on the following conditions.

Evaporator temperature 4 ℃

Condenser temperature 43 ° C

Subcooling amount 6 ℃

Recovery gas temperature 18 ℃

Compressor Efficiency 70%

It is noted that the cooling capacity includes overheating.

The composition had an energy efficiency (EER) comparable to R22 and R410A while maintaining the proper discharge temperature. The capacity for the specific compositions listed in Table 16 was also similar to R22, indicating that these compositions could be alternative refrigerants for R22 in refrigeration and air conditioning. In addition, in the compositions described in Table 16, there were compositions having a capacity close to or equivalent to the capacity of R410A, indicating that these compositions could be alternative refrigerants for R410A in refrigeration and air conditioning.

Example 11

Refrigeration performance data

Table 17 below shows the performance of various refrigerant compositions of the present invention as compared to HCFC-22, R410A, R407C and R417A. In Table 17, "Evap pressure" is the evaporator pressure, "Cond pressure" is the condenser pressure, "Comp Disch T" is the compressor discharge temperature, "EER" is the energy efficiency, and "CAP" is the capacity. The data are based on the following conditions.

Evaporator temperature 4.4 ℃

Condenser temperature 54.4 ℃

Supercooling amount 5.5 ℃

Recovery gas temperature 15.6 ℃

Compressor Efficiency 100%

It is noted that the cooling capacity includes overheating.

The composition had an energy efficiency (EER) comparable to R22, R407C, R417A and R410A while maintaining a low discharge temperature. The capacity for the compositions shown in Table 17 was also similar to R22, R407C and R417A, indicating that these compositions could be alternative refrigerants for R22, R407C or R417A in refrigeration and air conditioning.

Claims (14)

(i) cyclic fluoroolefins of the formula cyclo- [CX = CY (CZW) _n -] _wherein X, Y, Z and W are independently H or F and n is an integer from 2 to 5; And
(ii) -1- butene _{(CF 3 CF 2 CF = CF} 2) as a 1,1,2,3,3,4,4,4- octafluoro; 2-butene to 1,1,1,2,4,4,4- heptafluoropropane _{(CF 3 CF = CHCF 3)} ; 1,2,3,3,4,4,4-heptafluoro-1-butene (CHF = CFCF ₂ CF ₃ ); 2-butene (CHF ₂ CF = CFCF ₃₎ a 1,1,1,2,3,4,4- heptafluoropropane; As 1,3,3,3- tetrafluoroethane (trifluoromethyl) -2-1-propene _{((CF 3) 2 C =} CHF); 1,1,3,3,4,4,4- heptafluoro-1-butene as a _{(CF 2 = CHCF 2 CF 3} ); 1,1,2,3,4,4,4- heptafluoro-1-butene as a (CF ₂ = CFCHFCF _3); A 1,1,2,3,3,4,4- heptafluoro-1-butene _{(CF 2 = CFCF 2 CHF 2} ); A 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 as a _{(CHF = CHCF 2 CF 3)} ; 1-butene (CHF = CFCHFCF ₃₎ a 1,2,3,4,4,4- hexafluoro; 1,2,3,3,4,4-hexafluoro-1-butene (CHF = CFCF ₂ CHF ₂ ); 1,1,2,3,4,4- hexafluoro-2-butene as a _{(CHF 2 CF = CFCHF 2)} ; 1,1,1,2,3,4-hexafluoro- ₂ -butene (CH ₂ FCF = CFCF ₃ ); 2-butene (CHF ₂ CH = CFCF ₃₎ a 1,1,1,2,4,4- hexafluoro; 1,1,1,3,4,4- hexafluoro-2-butene as a _{(CF 3 CH = CFCHF 2)} ; 1-butene _{(CF 2 = CFCF 2 CH 2} F) to 1,1,2,3,3,4- hexafluoro; 1,1,2,3,4,4- hexafluoro-1-butene as a (CF ₂ = CFCHFCHF _2); A 1,1,1,2,4- pentafluoro-2-butene _{(CH 2 FCH = CFCF 3)} ; 1,1,1,3,4- pentafluoro-2-butene as a _{(CF 3 CH = CFCH 2 F} ); 3,3,4,4,4- pentafluoro-1-butene with _{(CF 3 CF 2 CH = CH} 2); 1,1,1,4,4- pentafluorophenyl-2-butene _{(CHF 2 CH = CHCF 3)} ; 2-butene (CH ₃ CF = CFCF ₃₎ with 1,1,1,2,3- pentafluoropropane; 2,3,3,4,4- pentafluorophenyl-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- pentafluorophenyl-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 pentafluoroethyl-2-methyl-1-propene _{(CF 2 = C (CF 3} ) (CH 3)); 2- (difluoro-methyl) -3,3,3-trifluoro-1-propene _{(CH 2 = C (CHF 2} ) (CF 3)); 1-butene (CH ₂ = CFCHFCF ₃₎ with 2,3,4,4,4- pentafluoropropane; 1,2,4,4,4- pentafluorophenyl-1-butene _{(CHF = CFCH 2 CF 3)} ; 1,3,4,4,4- pentafluorophenyl-1-butene (CHF = CHCHFCF _3); 1,3,3,4,4- pentafluoro-1-butene as a _{(CHF = CHCF 2 CHF 2)} ; 1,2,3,4,4- pentafluorophenyl-1-butene (CHF = CFCHFCHF _2); 1-butene as 3,3,4,4- tetrafluoroethane _{(CH 2 = CHCF 2 CHF 2} ); 1,1-di (difluoromethyl) -2-fluoro-1-propene _{(CF 2 = C (CHF 2} ) (CH 3)); 2-methyl-1-propene _{(CHF = C (CF 3)} (CH 3)) to 1,3,3,3- tetrafluoroethane; 3,3-di (difluoromethyl) -2-fluoro-1-propene _{(CH 2 = C (CHF 2} ) 2); 2-butene-1,1,1,2-tetrafluoroethane _{(CF 3 CF = CHCH 3)} ; 2-butene as 1,1,1,3- tetrafluoroethane (CF ₃ CH = CHCF _3); 1,1,1,2,3,4,4,5,5,5- to deca-fluoro-2-pentene _{(CF 3 CF = CFCF 2 CF} 3); 1,1,2,3,3,4,4,5,5,5- to deca-fluoro-1-pentene _{(CF 2 = CFCF 2 CF 2} CF 3); A 1,1,1,4,4,4- hexafluoro (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); A 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)} ; A 1,2,3,4,4,4- hexafluoro (trifluoromethyl) -3-butene _{(CHF = CFCF (CF 3)} 2); A 1,1,2,4,4,4- hexafluoro (trifluoromethyl) -3-butene-1 _{(CF 2 = CFCH (CF 3} ) 2); A 1,1,1,4,4,4- hexafluoro (trifluoromethyl) -2-butene _{(CF 3 CH = C (CF} 3) 2); A 1,1,3,4,4,4- hexafluoro (trifluoromethyl) -3-butene-1 _{(CF 2 = CHCF (CF 3} ) 2); A 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 ); With 3,3,4,4,4- pentafluoropropane (trifluoromethyl) -2-butene _{(CH 2 = C (CF 3} ) CF 2 CF 3); With 1,1,4,4,4- pentafluoropropane (trifluoromethyl) -3-butene-1 (CF = CHCH ₂ (CF _{3) 2);} With 1,3,4,4,4- pentafluoropropane (trifluoromethyl) -3-butene _{(CHF = CHCF (CF 3)} 2); With 1,1,4,4,4- pentafluoropropane (trifluoromethyl) -2-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 ); A 3,3,4,4,5,5,5- heptafluoro-1-pentene _{(CF 3 CF 2 CF 2 CH} = CH 2); A 2,3,3,4,4,5,5- heptafluoro-1-pentene _{(CH 2 = CFCF 2 CF 2} CHF 2); A 1,1,3,3,5,5,5- heptafluoro-1-butene _{(CF 2 = CHCF 2 CH 2} CF 3); 3-methyl-2-butene as a 1,1,1,2,4,4,4- heptafluoropropane _{(CF 3 CF = C (CF} 3) (CH 3)); As 2,4,4,4- tetrafluoroethane (trifluoromethyl) -3-butene _{(CH 2 = CFCH (CF 3} ) 2); As 1,4,4,4- tetrafluoroethane (trifluoromethyl) -3-butene _{(CHF = CHCH (CF 3)} 2); As 1,1,1,4- tetrafluoroethane (trifluoromethyl) -2-butene _{(CH 2 FCH = C (CF} 3) 2); As 1,1,1,3- tetrafluoroethane (trifluoromethyl) -2-butene _{(CH 3 CF = C (CF} 3) 2); 1,1,1-trifluoro (trifluoromethyl) -2-butene _{((CF 3) 2 C =} CHCH 3); A 3,4,4,5,5,5- hexafluoro-2-pentene _{(CF 3 CF 2 CF = CHCH} 3); A 1,1,1,4,4,4- hexafluoro-2-methyl-2-butene _{(CF 3 C (CH 3)} = CHCF 3); 1-pentene _{(CH 2 = CHCF 2 CHFCF 3} ) a 3,3,4,5,5,5- hexafluoro; 4,4,4-trifluoro (trifluoromethyl) -3-butene _{(CH 2 = C (CF 3} ) CH 2 CF 3); 1-hexene with 1,1,2,3,3,4,4,5,5,6,6,6- dodeca-fluoro _{(CF 3 (CF 2) 3} CF = CF 2); 3-hexene _{(CF 3 CF 2 CF = CFCF} 2 CF 3) in 1,1,1,2,2,3,4,5,5,6,6,6- dodeca-fluoro; A 1,1,1,4,4,4- hexafluoro (trifluoromethyl) -2,3-bis-2-butene _{((CF 3) 2 C =} C (CF 3) 2); A 1,1,1,2,3,4,5,5,5- nonafluoro -4- (trifluoromethyl) -2-pentene _{((CF 3) 2 CFCF =} CFCF 3); A 1,1,1,4,4,5,5,5- octafluoro -2- (trifluoromethyl) -2-pentene _{((CF 3) 2 C =} CHC 2 F 5); A 1,1,1,3,4,5,5,5- octafluoro -4- (trifluoromethyl) -2-pentene _{((CF 3) 2 CFCF =} CHCF 3); 4,4,4-trifluoro (trifluoromethyl) -3,3-bis-1-butene _{(CH 2 = CHC (CF 3} ) 3); (CF ₃ ) ₂ C = C (CH ₃ ) (CF ₃ )) in the presence of 1,1,1,4,4,4-hexafluoro-2- (trifluoromethyl) ; (Trifluoromethyl) -4-2,3,3,5,5,5- hexafluoro-1-pentene _{(CH 2 = CFCF 2 CH (} CF 3) 2); 3-methyl-2-pentene as a 1,1,1,2,4,4,5,5,5- nonafluoro _{(CF 3 CF = C (CH} 3) CF 2 CF 3); (Trifluoromethyl) -4-1,1,1,5,5,5-hexafluoro-2-pentene _{(CF 3 CH = CHCH (CF} 3) 2); A 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- octafluoro-1-hexene _{(CH 2 = CHCF 2 CF 2} CF 2 CHF 2); A 1,1,1,4,4- pentafluoro -2- (trifluoromethyl) -2-pentene _{((CF 3) 2 C =} CHCF 2 CH 3); With 4,4,5,5,5- pentafluoropropane (trifluoromethyl) -2-pentene _{(CH 2 = C (CF 3} ) CH 2 C 2 F 5); 2-methyl-1-pentene as a 3,3,4,4,5,5,5- heptafluoropropane _{(CF 3 CF 2 CF 2 C} (CH 3) = CH 2); A 4,4,5,5,6,6,6- heptafluoro-2-hexene _{(CF 3 CF 2 CF 2 CH} = CHCH 3); A 4,4,5,5,6,6,6- heptafluoro-1-hexene _{(CH 2 = CHCH 2 CF 2} C 2 F 5); A 1,1,1,2,2,3,4- heptafluoro-3-hexene _{(CF 3 CF 2 CF = CFC} 2 H 5); (Trifluoromethyl) -4-4,5,5,5- tetrafluoro-1-pentene _{(CH 2 = CHCH 2 CF (} CF 3) 2); 4-methyl-2-pentene to 1,1,1,2,5,5,5- heptafluoropropane _{(CF 3 CF = CHCH (CF} 3) (CH 3)); As 1,1,1,3- tetrafluoroethane -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- tetra deca fluoro-2-heptene as a _{(CF 3 CF = CFCF 2 CF} 2 C 2 F 5) ; _{(5 CF 3 CF 2 CF =} CFCF 2 C 2 F) 1,1,1,2,2,3,4,5,5,6,6,7,7,7- tetra deca fluoro-3-heptene ; 1,1,1,3,4,4,5,5,6,6,7,7,7- a tree deca-fluoro-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- a tree deca-fluoro-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- tree to deca-fluoro-3-heptene _{(CF 3 CF 2 CH = CFCF} 2 C 2 F 5); 1,1,1,2,2,3,5,5,6,6,7,7,7- tree to deca-fluoro-3-heptene _{(CF 3 CF 2 CF = CHCF} 2 C 2 F 5); _{CF 2 = CFOCF 2 CF 3 (} PEVE) , and CF ₂ = fluoroolefin selected from the group consisting of CFOCF ₃ (PMVE)
&Lt; RTI ID = 0.0 &gt; and / or &lt; / RTI &gt; (i) at least one fluoroolefin compound; And (ii) at least one combustible refrigerant; The fluoroolefin,
(a) cyclic fluoroolefins of the formula cyclo- [CX = CY (CZW) _n -] _wherein X, Y, Z and W are independently H or F and n is an integer from 2 to 5; And
(b) -2- butene (CF ₃ CF = CFCF ₃₎ a 1,1,1,2,3,4,4,4- octafluoro; A 1,1,2,3,3,4,4,4- octafluoro-1-butene _{(CF 3 CF 2 CF = CF} 2); 2-butene to 1,1,1,2,4,4,4- heptafluoropropane _{(CF 3 CF = CHCF 3)} ; 1,2,3,3,4,4,4-heptafluoro-1-butene (CHF = CFCF ₂ CF ₃ ); 2-butene (CHF ₂ CF = CFCF ₃₎ a 1,1,1,2,3,4,4- heptafluoropropane; As 1,3,3,3- tetrafluoroethane (trifluoromethyl) -2-1-propene _{((CF 3) 2 C =} CHF); 1,1,3,3,4,4,4- heptafluoro-1-butene as a _{(CF 2 = CHCF 2 CF 3} ); 1,1,2,3,4,4,4- heptafluoro-1-butene as a (CF ₂ = CFCHFCF _3); A 1,1,2,3,3,4,4- heptafluoro-1-butene _{(CF 2 = CFCF 2 CHF 2} ); A 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 as a _{(CHF = CHCF 2 CF 3)} ; 1-butene (CHF = CFCHFCF ₃₎ a 1,2,3,4,4,4- hexafluoro; 1,2,3,3,4,4-hexafluoro-1-butene (CHF = CFCF ₂ CHF ₂ ); 1,1,2,3,4,4- hexafluoro-2-butene as a _{(CHF 2 CF = CFCHF 2)} ; 1,1,1,2,3,4-hexafluoro- ₂ -butene (CH ₂ FCF = CFCF ₃ ); 2-butene (CHF ₂ CH = CFCF ₃₎ a 1,1,1,2,4,4- hexafluoro; 1,1,1,3,4,4- hexafluoro-2-butene as a _{(CF 3 CH = CFCHF 2)} ; 1-butene _{(CF 2 = CFCF 2 CH 2} F) to 1,1,2,3,3,4- hexafluoro; 1,1,2,3,4,4- hexafluoro-1-butene as a (CF ₂ = CFCHFCHF _2); 1,1,1,2,3,4,4,5,5,5- to deca-fluoro-2-pentene _{(CF 3 CF = CFCF 2 CF} 3); 1,1,2,3,3,4,4,5,5,5- to deca-fluoro-1-pentene _{(CF 2 = CFCF 2 CF 2} CF 3); A 1,1,1,4,4,4- hexafluoro (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); A 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)} ; A 1,2,3,4,4,4- hexafluoro (trifluoromethyl) -3-butene _{(CHF = CFCF (CF 3)} 2); A 1,1,2,4,4,4- hexafluoro (trifluoromethyl) -3-butene-1 _{(CF 2 = CFCH (CF 3} ) 2); A 1,1,1,4,4,4- hexafluoro (trifluoromethyl) -2-butene _{(CF 3 CH = C (CF} 3) 2); A 1,1,3,4,4,4- hexafluoro (trifluoromethyl) -3-butene-1 _{(CF 2 = CHCF (CF 3} ) 2); A 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 ); With 3,3,4,4,4- pentafluoropropane (trifluoromethyl) -2-butene _{(CH 2 = C (CF 3} ) CF 2 CF 3); With 1,1,4,4,4- pentafluoropropane (trifluoromethyl) -3-butene-1 (CF = CHCH ₂ (CF _{3) 2);} With 1,3,4,4,4- pentafluoropropane (trifluoromethyl) -3-butene _{(CHF = CHCF (CF 3)} 2); With 1,1,4,4,4- pentafluoropropane (trifluoromethyl) -2-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 ); A 3,3,4,4,5,5,5- heptafluoro-1-pentene _{(CF 3 CF 2 CF 2 CH} = CH 2); A 2,3,3,4,4,5,5- heptafluoro-1-pentene _{(CH 2 = CFCF 2 CF 2} CHF 2); A 1,1,3,3,5,5,5- heptafluoro-1-butene _{(CF 2 = CHCF 2 CH 2} CF 3); 3-methyl-2-butene as a 1,1,1,2,4,4,4- heptafluoropropane _{(CF 3 CF = C (CF} 3) (CH 3)); As 2,4,4,4- tetrafluoroethane (trifluoromethyl) -3-butene _{(CH 2 = CFCH (CF 3} ) 2); As 1,4,4,4- tetrafluoroethane (trifluoromethyl) -3-butene _{(CHF = CHCH (CF 3)} 2); As 1,1,1,4- tetrafluoroethane (trifluoromethyl) -2-butene _{(CH 2 FCH = C (CF} 3) 2); As 1,1,1,3- tetrafluoroethane (trifluoromethyl) -2-butene _{(CH 3 CF = C (CF} 3) 2); 1-hexene with 1,1,2,3,3,4,4,5,5,6,6,6- dodeca-fluoro _{(CF 3 (CF 2) 3} CF = CF 2); 3-hexene _{(CF 3 CF 2 CF = CFCF} 2 CF 3) in 1,1,1,2,2,3,4,5,5,6,6,6- dodeca-fluoro; A 1,1,1,4,4,4- hexafluoro (trifluoromethyl) -2,3-bis-2-butene _{((CF 3) 2 C =} C (CF 3) 2); A 1,1,1,2,3,4,5,5,5- nonafluoro -4- (trifluoromethyl) -2-pentene _{((CF 3) 2 CFCF =} CFCF 3); A 1,1,1,4,4,5,5,5- octafluoro -2- (trifluoromethyl) -2-pentene _{((CF 3) 2 C =} CHC 2 F 5); A 1,1,1,3,4,5,5,5- octafluoro -4- (trifluoromethyl) -2-pentene _{((CF 3) 2 CFCF =} CHCF 3); 4,4,4-trifluoro (trifluoromethyl) -3,3-bis-1-butene _{(CH 2 = CHC (CF 3} ) 3); (CF ₃ ) ₂ C = C (CH ₃ ) (CF ₃ )) in the presence of 1,1,1,4,4,4-hexafluoro-2- (trifluoromethyl) ; (Trifluoromethyl) -4-2,3,3,5,5,5- hexafluoro-1-pentene _{(CH 2 = CFCF 2 CH (} CF 3) 2); 3-methyl-2-pentene as a 1,1,1,2,4,4,5,5,5- nonafluoro _{(CF 3 CF = C (CH} 3) CF 2 CF 3); (Trifluoromethyl) -4-1,1,1,5,5,5-hexafluoro-2-pentene _{(CF 3 CH = CHCH (CF} 3) 2); 1,1,1,2,3,4,4,5,5,6,6,7,7,7- tetra deca fluoro-2-heptene as a _{(CF 3 CF = CFCF 2 CF} 2 C 2 F 5) ; _{(5 CF 3 CF 2 CF =} CFCF 2 C 2 F) 1,1,1,2,2,3,4,5,5,6,6,7,7,7- tetra deca fluoro-3-heptene ; 1,1,1,3,4,4,5,5,6,6,7,7,7- a tree deca-fluoro-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- a tree deca-fluoro-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- tree to deca-fluoro-3-heptene _{(CF 3 CF 2 CH = CFCF} 2 C 2 F 5); And a 3-heptene _{(CF 3 CF 2 CF = CHCF} 2 C 2 F 5) in a tree 1,1,1,2,2,3,5,5,6,6,7,7,7- deca fluoro Fluoroolefins selected from the group consisting of
&Lt; / RTI &gt; 3. A lubricant composition according to claim 1 or 2 selected from the group consisting of mineral oils, paraffins, naphthenes, synthetic paraffins, alkylbenzenes, poly-alpha-olefins, polyalkylene glycols, polyvinyl ethers, polyol esters, &Lt; / RTI &gt; Comprising cooling the composition of claim 1 or 2, and then evaporating said composition in the vicinity of the object to be cooled. Comprising heating the composition of claim 1 or 2 and then condensing the composition in the vicinity of the object to be heated. (i) cyclic fluoroolefins of the formula cyclo- [CX = CY (CZW) _n -] _wherein X, Y, Z and W are independently H or F and n is an integer from 2 to 5; or
(ii) -1- propene (CF ₃ CF = CHF) with 1,2,3,3,3- pentafluoropropane; 1-propene to 1,1,3,3,3-pentafluoropropane _{(CF 3 CH = CF 2)} ; 1,1,2,3,3-pentafluoro-1-propene (CHF ₂ CF = CF ₂ ); 1,2,3,3-tetrafluoro-1-propene (CHF ₂ CF = CHF); 2,3,3,3- tetrafluoro-1-propene with _{(CF 3 CF = CH 2)} ; 1,3,3,3- tetrafluoro-1-propene with (CF ₃ CH = CHF); 1,1,2,3-tetrafluoro-1-propene (CH ₂ FCF = CF ₂ ); 1,1,3,3-tetrafluoro-1-propene (CHF ₂ CH = CF ₂ ); 2,3,3-Trifluoro-1-propene (CHF ₂ CF = CH ₂ ); 1-propene, 3,3,3-trifluoromethyl _{(CF 3 CH = CH 2)} ; In 1,1,2-trifluoro-1-propene _{(CH 3 CF = CF 2)} ; 1,1,3-trifluoro-1-propene (CH ₂ FCH = CF ₂ ); 1,2,3-trifluoro-1-propene (CH ₂ FCF = CHF); 1,3,3-trifluoro-1-propene (CHF ₂ CH = CHF); 2-butene to 1,1,1,2,3,4,4,4- octafluoro _{(CF 3 CF = CFCF 3)} ; A 1,1,2,3,3,4,4,4- octafluoro-1-butene _{(CF 3 CF 2 CF = CF} 2); 2-butene to 1,1,1,2,4,4,4- heptafluoropropane _{(CF 3 CF = CHCF 3)} ; 1,2,3,3,4,4,4-heptafluoro-1-butene (CHF = CFCF ₂ CF ₃ ); 2-butene (CHF ₂ CF = CFCF ₃₎ a 1,1,1,2,3,4,4- heptafluoropropane; As 1,3,3,3- tetrafluoroethane (trifluoromethyl) -2-1-propene _{((CF 3) 2 C =} CHF); 1,1,3,3,4,4,4- heptafluoro-1-butene as a _{(CF 2 = CHCF 2 CF 3} ); 1,1,2,3,4,4,4- heptafluoro-1-butene as a (CF ₂ = CFCHFCF _3); A 1,1,2,3,3,4,4- heptafluoro-1-butene _{(CF 2 = CFCF 2 CHF 2} ); A 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 as a _{(CHF = CHCF 2 CF 3)} ; 1-butene (CHF = CFCHFCF ₃₎ a 1,2,3,4,4,4- hexafluoro; 1,2,3,3,4,4-hexafluoro-1-butene (CHF = CFCF ₂ CHF ₂ ); 1,1,2,3,4,4- hexafluoro-2-butene as a _{(CHF 2 CF = CFCHF 2)} ; 1,1,1,2,3,4-hexafluoro- ₂ -butene (CH ₂ FCF = CFCF ₃ ); 2-butene (CHF ₂ CH = CFCF ₃₎ a 1,1,1,2,4,4- hexafluoro; 1,1,1,3,4,4- hexafluoro-2-butene as a _{(CF 3 CH = CFCHF 2)} ; 1-butene _{(CF 2 = CFCF 2 CH 2} F) to 1,1,2,3,3,4- hexafluoro; 1,1,2,3,4,4- hexafluoro-1-butene as a (CF ₂ = CFCHFCHF _2); 3,3,3-trifluoro (trifluoromethyl) -2-propene-1 _{(CH 2 = C (CF 3} ) 2); A 1,1,1,2,4- pentafluoro-2-butene _{(CH 2 FCH = CFCF 3)} ; 1,1,1,3,4- pentafluoro-2-butene as a _{(CF 3 CH = CFCH 2 F} ); 3,3,4,4,4- pentafluoro-1-butene with _{(CF 3 CF 2 CH = CH} 2); 1,1,1,4,4- pentafluorophenyl-2-butene _{(CHF 2 CH = CHCF 3)} ; 2-butene (CH ₃ CF = CFCF ₃₎ with 1,1,1,2,3- pentafluoropropane; 2,3,3,4,4- pentafluorophenyl-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- pentafluorophenyl-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 pentafluoroethyl-2-methyl-1-propene _{(CF 2 = C (CF 3} ) (CH 3)); 2- (difluoro-methyl) -3,3,3-trifluoro-1-propene _{(CH 2 = C (CHF 2} ) (CF 3)); 1-butene (CH ₂ = CFCHFCF ₃₎ with 2,3,4,4,4- pentafluoropropane; 1,2,4,4,4- pentafluorophenyl-1-butene _{(CHF = CFCH 2 CF 3)} ; 1,3,4,4,4- pentafluorophenyl-1-butene (CHF = CHCHFCF _3); 1,3,3,4,4- pentafluoro-1-butene as a _{(CHF = CHCF 2 CHF 2)} ; 1,2,3,4,4- pentafluorophenyl-1-butene (CHF = CFCHFCHF _2); 1-butene as 3,3,4,4- tetrafluoroethane _{(CH 2 = CHCF 2 CHF 2} ); 1,1-di (difluoromethyl) -2-fluoro-1-propene _{(CF 2 = C (CHF 2} ) (CH 3)); 2-methyl-1-propene _{(CHF = C (CF 3)} (CH 3)) to 1,3,3,3- tetrafluoroethane; 2-difluoro-methyl-3,3-difluoro-1-propene _{(CH 2 = C (CHF 2} ) 2); 2-butene-1,1,1,2-tetrafluoroethane _{(CF 3 CF = CHCH 3)} ; 2-butene as 1,1,1,3- tetrafluoroethane (CF ₃ CH = CHCF _3); 1,1,1,2,3,4,4,5,5,5- to deca-fluoro-2-pentene _{(CF 3 CF = CFCF 2 CF} 3); 1,1,2,3,3,4,4,5,5,5- to deca-fluoro-1-pentene _{(CF 2 = CFCF 2 CF 2} CF 3); A 1,1,1,4,4,4- hexafluoro (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); A 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)} ; A 1,2,3,4,4,4- hexafluoro (trifluoromethyl) -3-butene _{(CHF = CFCF (CF 3)} 2); A 1,1,2,4,4,4- hexafluoro (trifluoromethyl) -3-butene-1 _{(CF 2 = CFCH (CF 3} ) 2); A 1,1,1,4,4,4- hexafluoro (trifluoromethyl) -2-butene _{(CF 3 CH = C (CF} 3) 2); A 1,1,3,4,4,4- hexafluoro (trifluoromethyl) -3-butene-1 _{(CF 2 = CHCF (CF 3} ) 2); A 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 ); With 3,3,4,4,4- pentafluoropropane (trifluoromethyl) -2-butene _{(CH 2 = C (CF 3} ) CF 2 CF 3); With 1,1,4,4,4- pentafluoropropane (trifluoromethyl) -3-butene-1 (CF = CHCH ₂ (CF _{3) 2);} With 1,3,4,4,4- pentafluoropropane (trifluoromethyl) -3-butene _{(CHF = CHCF (CF 3)} 2); With 1,1,4,4,4- pentafluoropropane (trifluoromethyl) -2-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 ); A 3,3,4,4,5,5,5- heptafluoro-1-pentene _{(CF 3 CF 2 CF 2 CH} = CH 2); A 2,3,3,4,4,5,5- heptafluoro-1-pentene _{(CH 2 = CFCF 2 CF 2} CHF 2); A 1,1,3,3,5,5,5- heptafluoro-1-butene _{(CF 2 = CHCF 2 CH 2} CF 3); 3-methyl-2-butene as a 1,1,1,2,4,4,4- heptafluoropropane _{(CF 3 CF = C (CF} 3) (CH 3)); As 2,4,4,4- tetrafluoroethane (trifluoromethyl) -3-butene _{(CH 2 = CFCH (CF 3} ) 2); As 1,4,4,4- tetrafluoroethane (trifluoromethyl) -3-butene _{(CHF = CHCH (CF 3)} 2); As 1,1,1,4- tetrafluoroethane (trifluoromethyl) -2-butene _{(CH 2 FCH = C (CF} 3) 2); As 1,1,1,3- tetrafluoroethane (trifluoromethyl) -2-butene _{(CH 3 CF = C (CF} 3) 2); 1,1,1-trifluoro (trifluoromethyl) -2-butene _{((CF 3) 2 C =} CHCH 3); A 3,4,4,5,5,5- hexafluoro-2-pentene _{(CF 3 CF 2 CF = CHCH} 3); A 1,1,1,4,4,4- hexafluoro-2-methyl-2-butene _{(CF 3 C (CH 3)} = CHCF 3); 1-pentene _{(CH 2 = CHCF 2 CHFCF 3} ) a 3,3,4,5,5,5- hexafluoro; 3- (trifluoro methyl) - 4,4,4-trifluoro-1-butene _{(CH 2 = C (CF 3} ) CH 2 CF 3); 1-hexene with 1,1,2,3,3,4,4,5,5,6,6,6- dodeca-fluoro _{(CF 3 (CF 2) 3} CF = CF 2); 3-hexene _{(CF 3 CF 2 CF = CFCF} 2 CF 3) in 1,1,1,2,2,3,4,5,5,6,6,6- dodeca-fluoro; A 1,1,1,4,4,4- hexafluoro (trifluoromethyl) -2,3-bis-2-butene _{((CF 3) 2 C =} C (CF 3) 2); A 1,1,1,2,3,4,5,5,5- nonafluoro -4- (trifluoromethyl) -2-pentene _{((CF 3) 2 CFCF =} CFCF 3); A 1,1,1,4,4,5,5,5- octafluoro -2- (trifluoromethyl) -2-pentene _{((CF 3) 2 C =} CHC 2 F 5); A 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 (trifluoromethyl) -3,3-bis-1-butene _{(CH 2 = CHC (CF 3} ) 3); (CF ₃ ) ₂ C = C (CH ₃ ) (CF ₃ )). ; (Trifluoromethyl) -4-2,3,3,5,5,5- hexafluoro-1-pentene _{(CH 2 = CFCF 2 CH (} CF 3) 2); 3-methyl-2-pentene as a 1,1,1,2,4,4,5,5,5- nonafluoro _{(CF 3 CF = C (CH} 3) CF 2 CF 3); (Trifluoromethyl) -4-1,1,1,5,5,5-hexafluoro-2-pentene _{(CF 3 CH = CHCH (CF} 3) 2); A 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- octafluoro-1-hexene _{(CH 2 = CHCF 2 CF 2} CF 2 CHF 2); A 1,1,1,4,4- pentafluoro -2- (trifluoromethyl) -2-pentene _{((CF 3) 2 C =} CHCF 2 CH 3); With 4,4,5,5,5- pentafluoropropane (trifluoromethyl) -2-pentene _{(CH 2 = C (CF 3} ) CH 2 C 2 F 5); 2-methyl-1-pentene as a 3,3,4,4,5,5,5- heptafluoropropane _{(CF 3 CF 2 CF 2 C} (CH 3) = CH 2); A 4,4,5,5,6,6,6- heptafluoro-2-hexene _{(CF 3 CF 2 CF 2 CH} = CHCH 3); A 4,4,5,5,6,6,6- heptafluoro-1-hexene _{(CH 2 = CHCH 2 CF 2} C 2 F 5); A 1,1,1,2,2,3,4- heptafluoro-3-hexene _{(CF 3 CF 2 CF = CFC} 2 H 5); Methyl-1-pentene-4-trifluoro-4,5,5,5- tetrafluoroethane _{(CH 2 = CHCH 2 CF (} CF 3) 2); 4-methyl-2-pentene to 1,1,1,2,5,5,5- heptafluoropropane _{(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- tetra deca fluoro-2-heptene as a _{(CF 3 CF = CFCF 2 CF} 2 C 2 F 5) ; _{(5 CF 3 CF 2 CF =} CFCF 2 C 2 F) 1,1,1,2,2,3,4,5,5,6,6,7,7,7- tetra deca fluoro-3-heptene ; 1,1,1,3,4,4,5,5,6,6,7,7,7- a tree deca-fluoro-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- a tree deca-fluoro-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- tree to deca-fluoro-3-heptene _{(CF 3 CF 2 CH = CFCF} 2 C 2 F 5); 1,1,1,2,2,3,5,5,6,6,7,7,7- tree to deca-fluoro-3-heptene _{(CF 3 CF 2 CF = CHCF} 2 C 2 F 5); _{CF 2 = CFOCF 2 CF 3 (} PEVE); CF ₂ = CFOCF ₃ (PMVE), and combinations thereof.
(A) a centrifugal compressor, (b) a multistage centrifugal compressor, or (c) a single slab / single pass heat exchanger having one or more fluoroolefins selected from the group consisting of A method of providing heating or cooling in a refrigeration, air conditioning or heating pump arrangement, comprising introducing into a refrigeration, air conditioning or heating pump arrangement. A method for controlling a fire hazard in a device comprising the steps of: introducing the composition of claim 1 or 2 into a refrigeration device, an air conditioning device or a heating pump device comprising a flammable refrigerant and optionally adding a lubricant to the added composition; &Lt; / RTI &gt; using said composition. A method of using the composition to reduce flammability of the combustible refrigerant, comprising combining a combustible refrigerant with the refrigerant or heat transfer fluid composition of claim 1. A global warming index of at least 150 in a refrigeration, air conditioning, or heat pump apparatus, or providing a composition of claim 1 or 2 in combination with, in combination with, a refrigerant having a Global Warming Index &Lt; / RTI &gt; The method of any of the preceding claims, comprising combining the original refrigerant or heat transfer fluid composition with the composition of claim 1 to produce a second refrigerant or heat transfer fluid composition having a global warming index lower than the original refrigerant or heat transfer fluid composition Wherein the composition of claim 1 is used to reduce the global warming index of the refrigerant or heat transfer fluid composition of the composition. The method of any of the preceding claims, further comprising introducing into the refrigeration, air conditioning or heating pump arrangement a second refrigerant or heat transfer fluid composition having a lower GWP of claim 1 or 2, Gt; GWP &lt; / RTI &gt; of the original refrigerant or heat transfer fluid composition. A method of replacing an original refrigerant or heat transfer fluid composition with a second refrigerant or heat transfer fluid composition comprising providing a composition comprising at least one fluoroolefin as a second refrigerant or heat transfer fluid composition,
Wherein the original refrigerant or heat transfer fluid composition comprises (i) 1,1,1,2-tetrafluoroethane (R134a), (ii) 1,1-difluoroethane (R152a), (iii) , 1,2,3,3,3-heptafluoropropane (R227ea), (iv) 1,1,2-trichloro-1,2,2-trifluoroethane (R113) 1,1,2,3,4,4,5,5,5- to deca-fluoro-pentane (R43-10mee), (vi) C 4 F 9 OCH 3, (vii) 1,1,1,3,3 Dichloro-1,1,1-trifluoroethane (R123), (x) 1,1,1-trifluoroethanone (R123), (iii) fluorotrichloromethane , 1,3,3-pentafluoropropane (R245fa), (xi) 1,2-dichloro-1,1,2,2-tetrafluoroethane (R124), (xii) 1,1,1,3 (Xii) R401A, (xiv) R401B, (xv) R409A, (xvi) R409B, (xvii) R414B, (xviii) R416A, (xix) dichlorodifluoro Methane (R12) and (xx) R500,
(i) 1,1,1,2-tetrafluoroethane (R134a) is replaced by a second refrigerant or heat transfer fluid composition comprising trifluoromethyltrifluorovinyl ether (PMVE);
(ii) when 1,1-difluoroethane (R152a) is E-1,3,3,3-tetrafluoropropene (E-HFC-1234ze), 1,2,3,3,3-pentafluoro (HFC-1225z), 2,3,3,3-tetrafluoropropene (HFC-1234yf), 3,3,3-trifluoropropene (HFC-1243zf), and trifluoromethyl tri A second refrigerant or heat transfer fluid composition comprising at least one compound selected from the group consisting of fluorovinyl ether (PMVE);
(iii) 1,1,1,2,3,3-heptafluoropropane (R227ea) is E-1,3,3,3-tetrafluoropropene (E-HFC-1234ze) 2,3,3,3-pentafluoropropene (HFC-1225ye), 2,3,3,3-tetrafluoropropene (HFC-1234yf), 3,3,3-trifluoropropene HFC-1243zf) and trifluoromethyltrifluorovinyl ether (PMVE); wherein the second refrigerant or heat transfer fluid composition comprises at least one compound selected from the group consisting of HFC-1243zf and trifluoromethyltrifluorovinyl ether (PMVE);
(iv) when 1,1,2-trichloro-1,2,2-trifluoroethane (R113) is 1,1,1,3,4,5,5,5-octafluoro-4- Fluoromethyl) -2-butene (HFC-152-11mmyyz); 1,1,1,4,4,5,5,5-octafluoro-2- (trifluoromethyl) -2-pentene (HFC-152-11mmtz); 1,1,1,2,2,3,4,5,5,6,6,6-dodecafluoro-3-hexene (HFC-151-12mcy); 1,1,1,3-tetrafluoro-2-butene (HFC-1354mzy); 1,1,1,4,4,4-hexafluoro-2,3-bis (trifluoromethyl) -2-butene (HFC-151-12mmtt); 1,2,3,3,4,4,5,5,6,6-decafluorocyclohexene (FC-C151-10y); 3,3,4,4,5,5,5,5-heptafluoro-2-methyl-1-pentene (HFC-1567fts); 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene (PFBE); 4,4,5,5,6,6,6-heptafluoro-2-hexene (HFC-1567szz); And at least one selected from the group consisting of 1,1,1,2,3,4,5,5,5-nonafluoro-4- (trifluoromethyl) -2-pentene (HFC-151-12mmzz) A second refrigerant or heat transfer fluid composition comprising the compound;
(v) 1,1,1,3,4,5,5,5-octafluoro-4- (trifluoromethyl) -2-butene (HFC-152-11mmyyz); 1,1,1,4,4,5,5,5-octafluoro-2- (trifluoromethyl) -2-pentene (HFC-152-11mmtz); 1,1,1,2,2,3,4,5,5,6,6,6-dodecafluoro-3-hexene (HFC-151-12mcy); 1,1,1,3-tetrafluoro-2-butene (HFC-1354mzy); 1,1,1,4,4,4-hexafluoro-2,3-bis (trifluoromethyl) -2-butene (HFC-151-12mmtt); 1,2,3,3,4,4,5,5,6,6-decafluorocyclohexene (FC-C151-10y); 3,3,4,4,5,5,5,5-heptafluoro-2-methyl-1-pentene (HFC-1567fts); 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene (PFBE); 4,4,5,5,6,6,6-heptafluoro-2-hexene (HFC-1567szz); And at least one selected from the group consisting of 1,1,1,2,3,4,5,5,5-nonafluoro-4- (trifluoromethyl) -2-pentene (HFC-151-12mmzz) A second refrigerant or heat transfer fluid composition comprising the compound;
(vi) C ₄ F ₉ OCH ₃ is 1,1,1,3,4,5,5,5-octafluoro-4- (trifluoromethyl) -2-butene (HFC-152-11mmyyz); 1,1,1,4,4,5,5,5-octafluoro-2- (trifluoromethyl) -2-pentene (HFC-152-11mmtz); 1,1,1,2,2,3,4,5,5,6,6,6-dodecafluoro-3-hexene (HFC-151-12mcy); 1,1,1,3-tetrafluoro-2-butene (HFC-1354mzy); 1,1,1,4,4,4-hexafluoro-2,3-bis (trifluoromethyl) -2-butene (HFC-151-12mmtt); 1,2,3,3,4,4,5,5,6,6-decafluorocyclohexene (FC-C151-10y); 3,3,4,4,5,5,5,5-heptafluoro-2-methyl-1-pentene (HFC-1567fts); 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene (PFBE); 4,4,5,5,6,6,6-heptafluoro-2-hexene (HFC-1567szz); And at least one selected from the group consisting of 1,1,1,2,3,4,5,5,5-nonafluoro-4- (trifluoromethyl) -2-pentene (HFC-151-12mmzz) A second refrigerant or heat transfer fluid composition comprising the compound;
(vii) 1,1,1,3,3-pentafluorobutane (R365mfc) is 1,1,1,3,4,5,5,5-octafluoro-4- (trifluoromethyl) 2-butene (HFC-152-11mmyyz); 1,1,1,4,4,5,5,5-octafluoro-2- (trifluoromethyl) -2-pentene (HFC-152-11mmtz); 1,1,1,2,2,3,4,5,5,6,6,6-dodecafluoro-3-hexene (HFC-151-12mcy); 1,1,1,3-tetrafluoro-2-butene (HFC-1354mzy); 1,1,1,4,4,4-hexafluoro-2,3-bis (trifluoromethyl) -2-butene (HFC-151-12mmtt); 1,2,3,3,4,4,5,5,6,6-decafluorocyclohexene (FC-C151-10y); 3,3,4,4,5,5,5,5-heptafluoro-2-methyl-1-pentene (HFC-1567fts); 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene (PFBE); 4,4,5,5,6,6,6-heptafluoro-2-hexene (HFC-1567szz); And at least one selected from the group consisting of 1,1,1,2,3,4,5,5,5-nonafluoro-4- (trifluoromethyl) -2-pentene (HFC-151-12mmzz) A second refrigerant or heat transfer fluid composition comprising the compound;
(viii) fluorotrichloromethane (R11) is 1,2,3,3,4,4,5,5-octafluorocyclopentene (FC-C1418y), 1,1,1,2,3,4 , 4,5,5,5-decafluoro-2-pentene (FC-141-10myy); 1,1,1,2,4,4,5,5,5-nonafluoro-2-pentene (HFC-1429myz); 1,1,1,3,4,4,5,5,5-nonafluoro-2-pentene (HFC-1429mzy); 3,3,4,4,5,5,5,5-heptafluoro-1-pentene (HFC-1447fz); And a second refrigerant comprising at least one compound selected from the group consisting of 1,1,1,4,4,4-hexafluoro-2- (trifluoromethyl) -2-butene (HFC-1429mzt) Replaced by a heat transfer fluid composition;
(ix) 2,2-dichloro-1,1,1-trifluoroethane (R123) is 1,2,3,3,4,4,5,5-octafluorocyclopentene (FC-C1418y); 1,1,1,2,3,4,4,5,5,5-decafluoro-2-pentene (FC-141-10myy); 1,1,1,2,4,4,5,5,5-nonafluoro-2-pentene (HFC-1429myz); 1,1,1,3,4,4,5,5,5-nonafluoro-2-pentene (HFC-1429mzy); 3,3,4,4,5,5,5,5-heptafluoro-1-pentene (HFC-1447fz); And a second refrigerant comprising at least one compound selected from the group consisting of 1,1,1,4,4,4-hexafluoro-2- (trifluoromethyl) -2-butene (HFC-1429mzt) Replaced by a heat transfer fluid composition;
(x) 1,1,1,3,3-pentafluoropropane (R245fa) is 2,3,3-trifluoropropene (HFC-1243yf); 1,3,3,3-tetrafluoropropene (HFC-1234ze); 1,1,1,2,4,4,4-heptafluoro-2-butene (HFC-1327my); 1,2,3,3-tetrafluoropropene (HFC-1234ye); And at least one compound selected from the group consisting of pentafluoroethyl trifluorovinyl ether (PEVE);
(xi) 1,2-dichloro-1,1,2,2-tetrafluoroethane (R124) is 1,1,1,2,3,4,4,4-octafluoro-2-butene -1318my); 1,2,3,3,4,4-hexafluorocyclobutene (FC-C1316cc); 2,3,3,4,4,4-hexafluoro-1-butene (HFC-1336yf); And at least one compound selected from the group consisting of 3,3,4,4,4-pentafluoro-1-butene (HFC-1345fz);
(xii) 1,1,1,3,3,3-hexafluoropropane (R236fa) is 1,1,1,2,3,4,4,4-octafluoro-2-butene (FC-1318my ); 1,2,3,3,4,4-hexafluorocyclobutene (FC-C1316cc); 2,3,3,4,4,4-hexafluoro-1-butene (HFC-1336yf); And at least one compound selected from the group consisting of 3,3,4,4,4-pentafluoro-1-butene (HFC-1345fz);
(xiii) R401A is E-1,3,3,3-tetrafluoropropene (E-HFC-1234ze); 1,2,3,3,3-pentafluoropropene (HFC-1225ye); 2,3,3,3-tetrafluoropropene (HFC-1234yf); 3,3,3-trifluoropropene (HFC-1243zf); And at least one compound selected from the group consisting of trifluoromethyltrifluoro vinyl ether (PMVE);
(xiv) R401B is E-1,3,3,3-tetrafluoropropene (E-HFC-1234ze); 1,2,3,3,3-pentafluoropropene (HFC-1225ye); 2,3,3,3-tetrafluoropropene (HFC-1234yf); 3,3,3-trifluoropropene (HFC-1243zf); And at least one compound selected from the group consisting of trifluoromethyltrifluoro vinyl ether (PMVE);
(xv) R409A is E-1,3,3,3-tetrafluoropropene (E-HFC-1234ze); 1,2,3,3,3-pentafluoropropene (HFC-1225ye); 2,3,3,3-tetrafluoropropene (HFC-1234yf); 3,3,3-trifluoropropene (HFC-1243zf); And at least one compound selected from the group consisting of trifluoromethyltrifluoro vinyl ether (PMVE);
(xvi) R409B is E-1,3,3,3-tetrafluoropropene (E-HFC-1234ze); 1,2,3,3,3-pentafluoropropene (HFC-1225ye); 2,3,3,3-tetrafluoropropene (HFC-1234yf); 3,3,3-trifluoropropene (HFC-1243zf); And at least one compound selected from the group consisting of trifluoromethyltrifluoro vinyl ether (PMVE);
(xvii) R414B is E-1,3,3,3-tetrafluoropropene (E-HFC-1234ze); 1,2,3,3,3-pentafluoropropene (HFC-1225ye); 2,3,3,3-tetrafluoropropene (HFC-1234yf); 3,3,3-trifluoropropene (HFC-1243zf); And at least one compound selected from the group consisting of trifluoromethyltrifluoro vinyl ether (PMVE);
(xviii) R416A is E-1,3,3,3-tetrafluoropropene (E-HFC-1234ze); 1,2,3,3,3-pentafluoropropene (HFC-1225ye); 2,3,3,3-tetrafluoropropene (HFC-1234yf); 3,3,3-trifluoropropene (HFC-1243zf); And at least one compound selected from the group consisting of trifluoromethyltrifluoro vinyl ether (PMVE);
(xix) Dichlorodifluoromethane (R12) is 1,2,3,3,3-pentafluoropropene (HFC-1225ye); 2,3,3,3-tetrafluoropropene (HFC-1234yf); 3,3,3-trifluoropropene (HFC-1243zf); And at least one compound selected from the group consisting of trifluoromethyltrifluoro vinyl ether (PMVE);
(xx) R 500 is 1,2,3,3,3-pentafluoropropene (HFC-1225ye); 2,3,3,3-tetrafluoropropene (HFC-1234yf); 3,3,3-trifluoropropene (HFC-1243zf); And at least one member selected from the group consisting of trifluoromethyltrifluorovinyl ether (PMVE) -trifluoropropene, 3,3,3-trifluoropropene, and trifluoromethyltrifluorovinyl ether Wherein the second refrigerant or heat transfer fluid composition comprises a compound.
A method of replacing an original refrigerant or heat transfer fluid composition with a second refrigerant or heat transfer fluid composition. A method of using the composition as a heat transfer fluid composition, comprising transferring the composition of claim 1 or 2 from a heat source to a heat sink. A refrigeration, air conditioning or heating pump device comprising an evaporator, a compressor, a condenser and an expansion device, and comprising the composition as claimed in claim 1 or 2.