Fluorinated alkene systems

Abstract

To provide a process for transferring heat efficiently.SOLUTION: A process includes contacting an article with a heat transfer media. The heat transfer media includes a composition including a compound of formula (4). RfCF3(CX5X6CX7X8)nCH=CHCX9X10CX11X12F...(4) In the compound of formula (4), Rf is a C1 to C10 perfluorinated alkyl group, X5, X6, X7, X8, X9, X10, X11 and X12 are each independently H, Cl, or F, and n is an integer of 0 or 1. The total number of F represented by X5, X6, X7, X8, X9, X10, X11 and X12 is at least 2 and the heat transfer media includes 1,1,1,4,4,5,5,5- octafluoropenta -2-ene (F12E, CF3CH=CHC2F5) as a co-compound.SELECTED DRAWING: Figure 1

Description

Technical Field

[0001] This application claims the benefit of U.S. Patent Application No. 62 / 835,703, filed Apr. 18, 2019. The disclosure of U.S. Patent Application No. 62 / 835,703 is incorporated herein by reference.

[0002] (Field of the Invention) The present invention is directed to the use of fluorinated alkene compounds such as heat transfer materials.

Background Art

[0003] There is interest in low-temperature heat utilization (i.e., heat at temperatures below about 300° C.). Such heat may be extracted from various commercial, industrial, or natural resources. The increase in the temperature of available heat by a high-temperature mechanical compression heat pump (HTHP) and the conversion of available heat into mechanical or electrical power via an organic Rankine cycle (ORC) are two promising approaches for the utilization of low-temperature heat.

[0004] ORC and HTHP require the use of a working fluid. Working fluids having a high global warming potential (GWP) commonly used in HTHP and ORC (e.g., HFC-245fa) have been under consideration, and there is a need for more environmentally sustainable working fluids for HTHP and ORC. More specifically, there is a need for a low-GWP working fluid having a boiling point higher than about 50° C. (hereinafter, “° C.”), which is particularly suitable for the conversion of available heat at temperatures close to or above 200° C. and is particularly suitable for heating from available heat at low temperatures to temperatures approaching 200° C. Even more specifically, a low-GWP working fluid having a boiling point close to that of ethanol (78.4° C.) can be advantageous as a replacement for ethanol in ORC systems for heavy-duty vehicles (e.g., trucks), particularly in Europe. Such fluids can also be used as solvents and heat transfer fluids for various applications including immersion cooling and phase change cooling (e.g., for electronics including data center cooling).

[0005] Fluoroalkenes such as F23E(C2F5CH=CHC3F7) can be prepared from F-heptene-3 starting materials using a four-step preparation including a continuous hydrogenation / dehydrofluorination process. However, this process is long and based on relatively expensive starting materials (F-heptene is produced using the reaction of hexafluoropropene (HFP) with 2 moles of tetrafluoroethylene (TFE)).

[0006] International Publication No. 2008 / 057513 describes a process for preparing internal dihydrofluoroolefins of the formula RCH=CHC2F5, which includes reacting a fluorinated olefin of the formula RCH=CHF, wherein R is selected from perfluoroalkyl groups having 1 to 10 carbon atoms, and the alkyl group is either an n-alkyl chain, a sec-alkyl chain, or an isoalkyl chain in the liquid phase with tetrafluoroethylene in the presence of a antimony pentafluoride (SbF5) catalyst, removing the Lewis acid catalyst, and isolating the dihydrofluoroolefin. The disclosure of International Application No. 2008 / 057513 is incorporated herein by reference.

Prior Art Documents

Patent Documents

[0007]

Patent Document 1

Summary of the Invention

Means for Solving the Problems

[0008] The present invention is summarized by various embodiments. One embodiment of the present invention relates to a process for transferring heat, providing an article, contacting the article with a heat transfer medium, and the heat transfer medium includes a composition containing a compound of formula (4), R f CF3(CX5X6CX7X8) n CH=CHCX9X 10 CX11 X 12 F(4) In the formula, R f is a C1-C 10 perfluorinated alkyl group, In the formula, X5, X6, X7, X8, X9, X 10 , X 11 and X 12 are each independently H, Cl, or F, n is an integer of 0 or 1, X5, X6, X7, X8, X9, X 10 , X 11 and X 12 the total number of F represented by is at least 2, and optionally, (E)-1,1,1,4,4,4-Hexafluoro-2-butene, (HFO-1336mzz(E), CF3CH=CHCF3), (Z)-1,1,1,4,4,4-Hexafluoro-2-butene, (HFO-1336mzz(Z), CF3CH=CHCF3), (E)-2,3-Bis(trifluoromethyl)oxirane, (HFO-1336mzz(E)(epoxide), CFCH(-O-)CHCF3), (Z)-2,3-Bis(trifluoromethyl)oxirane, (HFO-1336mzz(Z)(epoxide), CFCH(-O-)CHCF3), HFO-1234ze(Z), HFO-1234ye(E), HFO-1234ye(Z), HFO-1438mzz(E), HFO-1438mzz(Z), Heptafluoro-4-(trifluoromethyl)-penta-2-ene, ((HFO-153-10mzzy), (mixture of HFO-153-10 isomers)), HFO-162-13mcyz, HFO-162-13mczy, (E)-1,3,4,4,4-Pentafluoro-3-(trifluoromethyl)-1-butene, (HFO-1438ezy(E), CFH=CHCF(CF3)2), (Z)-1,3,4,4,4-Pentafluoro-3-(trifluoromethyl)-1-butene, (HFO-1438ezy(Z), CFH=CHCF(CF3)2), HFO-1336ze(E), HFO-1336ze(Z), HFC-245fa, HFC-245ea, HFC-365mfc, HFC-43-10mee, (E)-1-Chloro-3,3,3-trifluoro-propene, (HCFO-1233zd(E), CHCl=CHCF3), (Z)-1-Chloro-3,3,3-trifluoro-propene, (HCFO-1233zd(Z), CHCl=CHCF3), HCFO-1224yd(E), HCFO-1224yd(Z), Iso-pentane, n-pentane, Cyclopentane, n-hexane, Cyclohexane, Heptane, Methyl formate, Dimethoxymethane, Dimethoxyethane, Propanal, Methanol, Ethanol, Isopropanol, N-propanol, trans-1,2-Dichloro-ethylene, cis-1,2-Dichloro-ethylene, 1-Methoxyheptafluoropropane (HFE-7000, CH3OCF2CF2CF3), Methyl nonafluorobutyl ether (HFE-71DA,C4F9OCH3), methoxy-nonafluorobutane (HFE-7100, C4F9OCH3, CH3O-3(CF2)-CH3), ethoxy-nonafluorobutane (HFE-7200, CH3CH2OCF2CF2CF2CF3, C4F9OC2H5), dodecafluoro-2-methylpentan-3-one (NOVEC-649 or Novec-1230, CF3CF2C(O)CF(CF3)2), 1,1,1,2,2,3,4,5,5,5-decafluoro-3-methoxy-4-(trifluoromethyl)-pentane (Novec-7300; C7H3F, 13 O; n-C2F5CF(OCH3)CF(CF3)2), siloxane, methyl perfluoroheptene ether, methoxy-perfluoro-heptene ether or MPHE (HFX-110; C7F 13(OCH3)), MPPE (HFX - 75), perfluorohepta - 2 - ene / perfluorohepta - 3 - ene (HFO - 161 - 14myy / HFO - 161 - 14mcyy, PFH, mixture, CF3CF=CFCF2CF2CF2CF3 / CF3CF2CF=CFCF2CF2CF3), perfluorohepta - 1 - ene (FC - 141 - 10cy, CF2=CFCF2CF2CF2CF2CF3), 1 - bromo - 1,2,3,3,3 - pentafluoropropene, (R - 1215ybB, CF3CF=CFBr), 2 - bromo - 1,1,1,3,3 - pentafluoro - 2 - propene, (R - 1215xbB1, CF3CBr=CF2), (E) - 1 - bromo - 2,3,3,3 - tetrafluoropropene, (HBFO - 1224ydB(E), CF3CF=CHBr), (Z) - 1 - bromo - 2,3,3,3 - tetrafluoropropene, (HBFO - 1224ydB(Z), CF3CF=CHBr), 2 - bromo - 3,3,3 - trifluoro - propene, (BFO - 1233xfB, CF3CBr=CH2), trans - DCE / R - 1336mzz(Z) mixture, (suitable mixtures include those disclosed in WO 2008 / 134061), (trans - DCE / methyl perfluoroheptene ether, (suitable mixtures include those disclosed in US Patent Publication No. 2012 / 0227764(A1)), (trans - DCE / HFC - 43 - 10mee mixture, (CHCl=CHCl / CF3CHFCHFCF2CF3), (suitable mixtures include those disclosed as disclosed in US Patent No. 5196137)), 2 - bromo - 2 - chloro - 1,1,1 - trifluoroethane, (R - 123B1, CHBrClCF3), 2,3 - dichloro - 3,3 - difluoropropene, (R - 1232xf, CClF2CCl=CH2), (E) - 1,1,4,4 - tetrafluoro - 2 - butene, (R - 1345mzz(E), CHF2CH=CHCHF2), 2 - bromo - 1,1 - difluoroethane, (BDFE, CHF2CH2Br), 1 - chloro - 2,3,3,4,4,4 - hexafluoro - 1 - butene, (HCFO - 1326yd - Z, CF3CF2CF=CHCl), 1 - chloro - 2,3,A co - compound comprising at least one of 3 - trifluoro - propene, (HCFO - 1233yd - Z, CHF2CF=CHCl), 2-(1,1,2,2 - tetrafluoroethoxy)-1 - fluoroethylene, (HFO - 1345ezcEβγ, CFH=CHOCF2CF2H), 2,3,3,3 - tetrafluoro - 1-(1,1,2,2 - tetrafluoroethoxy)prop - 1 - ene, (HFO - 1438mzycEγδ, CF3CF=CHOCF2CF2H), 1-(difluoromethoxy)-2,3,3,3 - tetrafluoroprop - 1 - ene, (HFO - 1336pzEαβ, CF3CF=CHOCF2H), 2,3,3 - trifluoro - 1-(trifluoromethoxy)prop - 1 - ene, (HFO - 1336mzyEαβ, CHF2CF=CHOCF3), 1,1,1,2,2,5,5,6,6,6 - decafluoro - 3 - hexene, (F22E, C2F5CH=CHC2F5), 1,1,1,2,2,3,3,4,4,7,7,8,8,9,9,10,10,10 - octadecafluoro - 5 - decene, (F44E, C4F9CH=CHC4F9), or 1,1,1,2,3,4,4,5,5,5 - decafluoropentane, (HFC - 43 - 10mee, CF3CHFCHFCF2CF3).

[0009] One embodiment of the present invention relates to any combination of the foregoing embodiments, wherein the compound of formula (4) comprises 1,1,1,2,2,5,5,6,6,7,7,7 - dodecafluorohept - 2 - ene, C3F7CH=CHC2F5 (F23E).

[0010] Another embodiment of the present invention relates to any combination of the foregoing embodiments, wherein the co - compound comprises at least one of HFO - 1336mzz(E), HFO - 1336mzz(Z), HFO - 1234ze(Z), HFO - 1234ye(E), HFO - 1234ye(Z), or ethanol.

[0011] Another embodiment of the present invention is a process for transferring heat, comprising providing an article, contacting the article with a heat transfer medium, wherein the heat transfer medium is comprising a composition formed by a process of contacting a compound of formula (1), R f CH=CHF(1) wherein R f is a C1-C 10 perfluorinated alkyl group, a fluorinated ethylene compound of formula (2), CX1X2=CX3X4(2) wherein X1, X2, X3 and X4 are each independently H, Cl, or F, at least one of X1, X2, X3 or X4 is F, present in an amount sufficient to form a composition comprising a compound of formula (3) in the presence of a Lewis acid catalyst, R f CF3(CX5X6CX7X8) n CH=CHCX9X 10 CX 11 X 12 F(3) wherein X5, X6, X7, X8, X9, X 10 , X 11 and X 12 are each independently H, Cl, or F, n is an integer of 0 or 1, the total number of H, Cl, and F represented by X5, X6, X7, X8, X9, X 10 , X 11 and X 12 is the same as the total number of H, Cl, and F provided by the fluorinated ethylene compound of formula (2), and optionally, (E)-1,1,1,4,4,4-Hexafluoro-2-butene, (HFO-1336mzz(E), CF3CH=CHCF3), (Z)-1,1,1,4,4,4-Hexafluoro-2-butene, (HFO-1336mzz(Z), CF3CH=CHCF3), (E)-2,3-Bis(trifluoromethyl)oxirane, (HFO-1336mzz(E)(epoxide), CFCH(-O-)CHCF3), (Z)-2,3-Bis(trifluoromethyl)oxirane, (HFO-1336mzz(Z)(epoxide), CFCH(-O-)CHCF3), HFO-1234ze(Z), HFO-1234ye(E), HFO-1234ye(Z), HFO-1438mzz(E), HFO-1438mzz(Z), Heptafluoro-4-(trifluoromethyl)-penta-2-ene, ((HFO-153-10mzzy), (mixture of HFO-153-10 isomers)), HFO-162-13mcyz, HFO-162-13mczy, (E)-1,3,4,4,4-Pentafluoro-3-(trifluoromethyl)-1-butene, (HFO-1438ezy(E), CFH=CHCF(CF3)2), (Z)-1,3,4,4,4-Pentafluoro-3-(trifluoromethyl)-1-butene, (HFO-1438ezy(Z), CFH=CHCF(CF3)2), HFO-1336ze(E), HFO-1336ze(Z), HFC-245fa, HFC-245ea, HFC-365mfc, HFC-43-10mee, (E)-1-Chloro-3,3,3-trifluoro-propene, (HCFO-1233zd(E), CHCl=CHCF3), (Z)-1-Chloro-3,3,3-trifluoro-propene, (HCFO-1233zd(Z), CHCl=CHCF3), HCFO-1224yd(E), HCFO-1224yd(Z), iso-Pentane, n-Pentane, Cyclopentane, n-Hexane, Cyclohexane, Heptane, Methyl formate, Dimethoxymethane, Dimethoxyethane, Propanal, Methanol, Ethanol, Isopropanol, N-Propanol, trans-1,2-Dichloro-ethylene, cis-1,2-Dichloro-ethylene, 1-Methoxyheptafluoropropane (HFE-7000, CH3OCF2CF2CF3), Methyl nonafluorobutyl ether (HFE-71DA,C4F9OCH3), methoxy-nonafluorobutane (HFE-7100, C4F9OCH3, CH3O-3(CF2)-CH3), ethoxy-nonafluorobutane (HFE-7200, CH3CH2OCF2CF2CF2CF3, C4F9OC2H5), dodecafluoro-2-methylpentan-3-one (NOVEC-649 or Novec-1230, CF3CF2C(O)CF(CF3)2), 1,1,1,2,2,3,4,5,5,5-decafluoro-3-methoxy-4-(trifluoromethyl)-pentane (Novec-7300; C7H3F, 13 O; n-C2F5CF(OCH3)CF(CF3)2), siloxane, methyl perfluoroheptene ether, methoxy-perfluoro-heptene ether or MPHE (HFX-110; C7F 13(OCH3)), MPPE (HFX - 75), perfluorohepta - 2 - ene / perfluorohepta - 3 - ene (HFO - 161 - 14myy / HFO - 161 - 14mcyy, PFH, mixture, CF3CF = CFCF2CF2CF2CF3 / CF3CF2CF = CFCF2CF2CF3), perfluorohepta - 1 - ene (FC - 141 - 10cy, CF2 = CFCF2CF2CF2CF2CF3), 1 - bromo - 1,2,3,3,3 - pentafluoropropene, (R - 1215ybB, CF3CF = CFBr), 2 - bromo - 1,1,1,3,3 - pentafluoro - 2 - propene, (R - 1215xbB1, CF3CBr = CF2), (E) - 1 - bromo - 2,3,3,3 - tetrafluoropropene, (HBFO - 1224ydB(E), CF3CF = CHBr), (Z) - 1 - bromo - 2,3,3,3 - tetrafluoropropene, (HBFO - 1224ydB(Z), CF3CF = CHBr), 2 - bromo - 3,3,3 - trifluoro - propene, (BFO - 1233xfB, CF3CBr = CH2), trans - DCE / R - 1336mzz(Z) mixture, (preferred mixtures include those disclosed in WO 2008 / 134061), (trans - DCE / methyl perfluoroheptene ether, (preferred mixtures include those disclosed in US Patent Publication No. 2012 / 0227764(A1)), (trans - DCE / HFC - 43 - 10mee mixture, (CHCl = CHCl / CF3CHFCHFCF2CF3), (suitable mixtures include those disclosed as disclosed in US Patent No. 5,196,137)), 2 - bromo - 2 - chloro - 1,1,1 - trifluoroethane, (R - 123B1, CHBrClCF3), 2,3 - dichloro - 3,3 - difluoropropene, (R - 1232xf, CClF2CCl = CH2), (E) - 1,1,4,4 - tetrafluoro - 2 - butene, (R - 1345mzz(E), CHF2CH = CHCHF2), 2 - bromo - 1,1 - difluoroethane, (BDFE, CHF2CH2Br), 1 - chloro - 2,3,3,4,4,4 - hexafluoro - 1 - butene, (HCFO - 1326yd - Z, CF3CF2CF = CHCl), 1 - chloro - 2,3,3-Trifluoro-propene, (HCFO-1233yd-Z, CHF2CF=CHCl), 2-(1,1,2,2-tetrafluoroethoxy)-1-fluoroethylene, (HFO-1345ezcEβγ, CFH=CHOCF2CF2H), 2,3,3,3-tetrafluoro-1-(1,1,2,2-tetrafluoroethoxy)prop-1-ene, (HFO-1438mzycEγδ, CF3CF=CHOCF2CF2H), 1-(difluoromethoxy)-2,3,3,3-tetrafluoroprop-1-ene, (HFO-1336pzEαβ, CF3CF=CHOCF2H), 2,3,3-trifluoro The co-compound includes at least one of perfluoro-1-(trifluoromethoxy)prop-1-ene, (HFO-1336mzyEαβ, CHF2CF=CHOCF3), 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene, (F22E, C2F5CH=CHC2F5), 1,1,1,2,2,3,3,4,4,7,7,8,8,9,9,10,10,10-octadecafluoro-5-decene, (F44E, C4F9CH=CHC4F9), or 1,1,1,2,3,4,4,5,5,5-decafluoropentane, (HFC-43-10mee, CF3CHFCHFCF2CF3).

[0012] One embodiment of the present invention relates to any combination of the preceding embodiments, wherein the compound of formula (3) comprises 1,1,1,2,2,5,5,6,6,7,7,7 dodecafluorohept-2-ene, C3F7CH=CHC2F5(F23E).

[0013] Another embodiment of the invention relates to any combination of the preceding embodiments, wherein the co-compound comprises at least one of HFO-1336mzz(E), HFO-1336mzz(Z), HFO-1234ze(Z), HFO-1234ye(E), HFO-1234ye(Z), or ethanol.

[0014] Another embodiment of the present invention is a process for treating a surface, comprising: Providing a surface; contacting the surface with a treatment composition; The surface includes a processable material deposited thereon, The treatment composition includes a composition comprising 1,1,1,2,2,5,5,6,6,7,7,7-dodecafluorohepta-2-ene, C3F7CH=CHC2F5 (F23E), and optionally, (E)-1,1,1,4,4,4-Hexafluoro-2-butene, (HFO-1336mzz(E), CF3CH=CHCF3), (Z)-1,1,1,4,4,4-Hexafluoro-2-butene, (HFO-1336mzz(Z), CF3CH=CHCF3), (E)-2,3-Bis(trifluoromethyl)oxirane, (HFO-1336mzz(E)(epoxide), CFCH(-O-)CHCF3), (Z)-2,3-Bis(trifluoromethyl)oxirane, (HFO-1336mzz(Z)(epoxide), CFCH(-O-)CHCF3), HFO-1234ze(Z), HFO-1234ye(E), HFO-1234ye(Z), HFO-1438mzz(E), HFO-1438mzz(Z), Heptafluoro-4-(trifluoromethyl)-penta-2-ene, ((HFO-153-10mzzy), (mixture of HFO-153-10 isomers)), HFO-162-13mcyz, HFO-162-13mczy, (E)-1,3,4,4,4-Pentafluoro-3-(trifluoromethyl)-1-butene, (HFO-1438ezy(E), CFH=CHCF(CF3)2), (Z)-1,3,4,4,4-Pentafluoro-3-(trifluoromethyl)-1-butene, (HFO-1438ezy(Z), CFH=CHCF(CF3)2), HFO-1336ze(E), HFO-1336ze(Z), HFC-245fa, HFC-245ea, HFC-365mfc, HFC-43-10mee, (E)-1-Chloro-3,3,3-trifluoro-propene, (HCFO-1233zd(E), CHCl=CHCF3), (Z)-1-Chloro-3,3,3-trifluoro-propene, (HCFO-1233zd(Z), CHCl=CHCF3), HCFO-1224yd(E), HCFO-1224yd(Z), Iso-pentane, n-pentane, Cyclopentane, n-hexane, Cyclohexane, Heptane, Methyl formate, Dimethoxymethane, Dimethoxyethane, Propanal, Methanol, Ethanol, Isopropanol, N-propanol, trans-1,2-Dichloro-ethylene, cis-1,2-Dichloro-ethylene, 1-Methoxyheptafluoropropane (HFE-7000, CH3OCF2CF2CF3), Methyl nonafluorobutyl ether (HFE-71DA,C4F9OCH3), methoxy-nonafluorobutane (HFE-7100, C4F9OCH3, CH3O-3(CF2)-CH3), ethoxy-nonafluorobutane (HFE-7200, CH3CH2OCF2CF2CF2CF3, C4F9OC2H5), dodecafluoro-2-methylpentan-3-one (NOVEC-649 or Novec-1230, CF3CF2C(O)CF(CF3)2), 1,1,1,2,2,3,4,5,5,5-decafluoro-3-methoxy-4-(trifluoromethyl)-pentane (Novec-7300; C7H3F, 13 O; n-C2F5CF(OCH3)CF(CF3)2), siloxane, methyl perfluoroheptene ether, methoxy-perfluoro-heptene ether or MPHE (HFX-110; C7F 13(OCH3)), MPPE (HFX-75), perfluorohepta-2-ene / perfluorohepta-3-ene (HFO-161-14myy / HFO-161-14mcyy, PFH, mixture, CF3CF=CFCF2CF2CF2CF3 / CF3CF2CF=CFCF2CF2CF3), perfluorohepta-1-ene (FC-141-10cy, CF2=CFCF2CF2CF2CF2CF3), 1-bromo-1,2,3,3,3-pentafluoropropene, (R-1215ybB, CF3CF=CFBr), 2-bromo-1,1,1,3,3-pentafluoro-2-propene, (R-1215xbB1, CF3CBr=CF2), (E)-1-bromo-2,3,3,3-tetrafluoropropene, (HBFO-1224ydB(E), CF3CF=CHBr), (Z)-1-bromo-2,3,3,3-tetrafluoropropene, (HBFO-1224ydB(Z), CF3CF=CHBr), 2-bromo-3,3,3-trifluoro-propene, (BFO-1233xfB, CF3CBr=CH2), trans-DCE / R-1336mzz(Z) mixture, (suitable mixtures include those disclosed in WO 2008 / 134061), (trans-DCE / methyl perfluoroheptene ether, (suitable mixtures include those disclosed in US Patent Publication No. 2012 / 0227764 (Al)), (trans-DCE / HFC-43-10mee mixture, (CHCl=CHCl / CF3CHFCHFCF2CF3), (suitable mixtures include those disclosed as disclosed in US Patent No. 5,196,137)), 2-bromo-2-chloro-1,1,1-trifluoroethane, (R-123B1, CHBrClCF3), 2,3-dichloro-3,3-difluoropropene, (R-1232xf, CClF2CCl=CH2), (E)-1,1,4,4-tetrafluoro-2-butene, (R-1345mzz(E), CHF2CH=CHCHF2), 2-bromo-1,1-difluoroethane, (BDFE, CHF2CH2Br), 1-chloro-2,3,3,4,4,4-hexafluoro-1-butene, (HCFO-1326yd-Z, CF3CF2CF=CHCl), 1-chloro-2,3,Comprising at least one of 3-trifluoro-propene, (HCFO-1233yd-Z, CHF2CF=CHCl), 2-(1,1,2,2-tetrafluoroethoxy)-1-fluoroethylene, (HFO-1345ezcEβγ, CFH=CHOCF2CF2H), 2,3,3,3-tetrafluoro-1-(1,1,2,2-tetrafluoroethoxy)prop-1-ene, (HFO-1438mzycEγδ, CF3CF=CHOCF2CF2H), 1-(difluoromethoxy)-2,3,3,3-tetrafluoroprop-1-ene, (HFO-1336pzEαβ, CF3CF=CHOCF2H), 2,3,3-trifluoro-1-(trifluoromethoxy)prop-1-ene, (HFO-1336mzyEαβ, CHF2CF=CHOCF3), 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene, (F22E, C2F5CH=CHC2F5), 1,1,1,2,2,3,3,4,4,7,7,8,8,9,9,10,10,10-octadecafluoro-5-decene, (F44E, C4F9CH=CHC4F9), or 1,1,1,2,3,4,4,5,5,5-decafluoropentane, (HFC-43-10mee, CF3CHFCHFCF2CF3).

[0015] Another embodiment of the present invention is an evaporator, a condenser, a compressor, an expansion device, and a heat transfer medium, wherein the heat transfer medium comprises a composition containing C3F7CH=CHC2F5 (F23E), and optionally, (E)-1,1,1,4,4,4-Hexafluoro-2-butene, (HFO-1336mzz(E), CF3CH=CHCF3), (Z)-1,1,1,4,4,4-Hexafluoro-2-butene, (HFO-1336mzz(Z), CF3CH=CHCF3), (E)-2,3-Bis(trifluoromethyl)oxirane, (HFO-1336mzz(E)(epoxide), CFCH(-O-)CHCF3), (Z)-2,3-Bis(trifluoromethyl)oxirane, (HFO-1336mzz(Z)(epoxide), CFCH(-O-)CHCF3), HFO-1234ze(Z), HFO-1234ye(E), HFO-1234ye(Z), HFO-1438mzz(E), HFO-1438mzz(Z), Heptafluoro-4-(trifluoromethyl)-penta-2-ene, ((HFO-153-10mzzy), (mixture of HFO-153-10 isomers)), HFO-162-13mcyz, HFO-162-13mczy, (E)-1,3,4,4,4-Pentafluoro-3-(trifluoromethyl)-1-butene, (HFO-1438ezy(E), CFH=CHCF(CF3)2), (Z)-1,3,4,4,4-Pentafluoro-3-(trifluoromethyl)-1-butene, (HFO-1438ezy(Z), CFH=CHCF(CF3)2), HFO-1336ze(E), HFO-1336ze(Z), HFC-245fa, HFC-245ea, HFC-365mfc, HFC-43-10mee, (E)-1-Chloro-3,3,3-trifluoro-propene, (HCFO-1233zd(E), CHCl=CHCF3), (Z)-1-Chloro-3,3,3-trifluoro-propene, (HCFO-1233zd(Z), CHCl=CHCF3), HCFO-1224yd(E), HCFO-1224yd(Z), iso-Pentane, n-Pentane, Cyclopentane, n-Hexane, Cyclohexane, Heptane, Methyl formate, Dimethoxymethane, Dimethoxyethane, Propanal, Methanol, Ethanol, Isopropanol, N-Propanol, trans-1,2-Dichloro-ethylene, cis-1,2-Dichloro-ethylene, 1-Methoxyheptafluoropropane (HFE-7000, CH3OCF2CF2CF3), Methyl nonafluorobutyl ether (HFE-71DA,C4F9OCH3), methoxy-nonafluorobutane (HFE-7100, C4F9OCH3, CH3O-3(CF2)-CH3), ethoxy-nonafluorobutane (HFE-7200, CH3CH2OCF2CF2CF2CF3, C4F9OC2H5), dodecafluoro-2-methylpentan-3-one (NOVEC-649 or Novec-1230, CF3CF2C(O)CF(CF3)2), 1,1,1,2,2,3,4,5,5,5-decafluoro-3-methoxy-4-(trifluoromethyl)-pentane (Novec-7300; C7H3F, 13 O; n-C2F5CF(OCH3)CF(CF3)2), siloxane, methyl perfluoroheptene ether, methoxy-perfluoro-heptene ether or MPHE (HFX-110; C7F 13(OCH3)), MPPE (HFX-75), perfluorohepta-2-ene / perfluorohepta-3-ene (HFO-161-14myy / HFO-161-14mcyy, PFH, mixture, CF3CF=CFCF2CF2CF2CF3 / CF3CF2CF=CFCF2CF2CF3), perfluorohepta-1-ene (FC-141-10cy, CF2=CFCF2CF2CF2CF2CF3), 1-bromo-1,2,3,3,3-pentafluoropropene, (R-1215ybB, CF3CF=CFBr), 2-bromo-1,1,1,3,3-pentafluoro-2-propene, (R-1215xbB1, CF3CBr=CF2), (E)-1-bromo-2,3,3,3-tetrafluoropropene, (HBFO-1224ydB(E), CF3CF=CHBr), (Z)-1-bromo-2,3,3,3-tetrafluoropropene, (HBFO-1224ydB(Z), CF3CF=CHBr), 2-bromo-3,3,3-trifluoro-propene, (BFO-1233xfB, CF3CBr=CH2), trans-DCE / R-1336mzz(Z) mixture, (preferred mixtures include those disclosed in International Publication No. WO 2008 / 134061), (trans-DCE / methyl perfluoroheptene ether, (preferred mixtures include those disclosed in US Patent Publication No. US 2012 / 0227764(A1)), (trans-DCE / HFC-43-10mee mixture, (CHCl=CHCl / CF3CHFCHFCF2CF3), (suitable mixtures include those disclosed as disclosed in US Patent No. 5,196,137)), 2-bromo-2-chloro-1,1,1-trifluoroethane, (R-123B1, CHBrClCF3), 2,3-dichloro-3,3-difluoropropene, (R-1232xf, CClF2CCl=CH2), (E)-1,1,4,4-tetrafluoro-2-butene, (R-1345mzz(E), CHF2CH=CHCHF2), 2-bromo-1,1-difluoroethane, (BDFE, CHF2CH2Br), 1-chloro-2,3,3,4,4,4-hexafluoro-1-butene, (HCFO-1326yd-Z, CF3CF2CF=CHCl), 1-chloro-2,3,Comprising at least one of 3-trifluoro-propene, (HCFO-1233yd-Z, CHF2CF=CHCl), 2-(1,1,2,2-tetrafluoroethoxy)-1-fluoroethylene, (HFO-1345ezcEβγ, CFH=CHOCF2CF2H), 2,3,3,3-tetrafluoro-1-(1,1,2,2-tetrafluoroethoxy)prop-1-ene, (HFO-1438mzycEγδ, CF3CF=CHOCF2CF2H), 1-(difluoromethoxy)-2,3,3,3-tetrafluoroprop-1-ene, (HFO-1336pzEαβ, CF3CF=CHOCF2H), 2,3,3-trifluoro-1-(trifluoromethoxy)prop-1-ene, (HFO-1336mzyEαβ, CHF2CF=CHOCF3), 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene, (F22E, C2F5CH=CHC2F5), 1,1,1,2,2,3,3,4,4,7,7,8,8,9,9,10,10,10-octadecafluoro-5-decene, (F44E, C4F9CH=CHC4F9), or 1,1,1,2,3,4,4,5,5,5-decafluoropentane, (HFC-43-10mee, CF3CHFCHFCF2CF3).

[0016] One embodiment of the present invention relates to any combination of the foregoing embodiments, in which the condenser operates at a temperature higher than 100°C.

[0017] Another embodiment of the present invention is a heat pipe having a working fluid therein, wherein the working fluid comprises a composition containing C3F7CH=CHC2F5 (F23E), and optionally (E)-1,1,1,4,4,4-Hexafluoro-2-butene, (HFO-1336mzz(E), CF3CH=CHCF3), (Z)-1,1,1,4,4,4-Hexafluoro-2-butene, (HFO-1336mzz(Z), CF3CH=CHCF3), (E)-2,3-Bis(trifluoromethyl)oxirane, (HFO-1336mzz(E)(epoxide), CFCH(-O-)CHCF3), (Z)-2,3-Bis(trifluoromethyl)oxirane, (HFO-1336mzz(Z)(epoxide), CFCH(-O-)CHCF3), HFO-1234ze(Z), HFO-1234ye(E), HFO-1234ye(Z), HFO-1438mzz(E), HFO-1438mzz(Z), Heptafluoro-4-(trifluoromethyl)-penta-2-ene, ((HFO-153-10mzzy), (mixture of HFO-153-10 isomers)), HFO-162-13mcyz, HFO-162-13mczy, (E)-,1,3,4,4,4-Pentafluoro-3-(trifluoromethyl)-1-butene, (HFO-1438ezy(E), CFH=CHCF(CF3)2), (Z)-1,3,4,4,4-Pentafluoro-3-(trifluoromethyl)-1-butene, (HFO-1438ezy(Z), CFH=CHCF(CF3)2), HFO-1336ze(E), HFO-1336ze(Z), HFC-245fa, HFC-245ea, HFC-365mfc, HFC-43-10mee, (E)-1-Chloro-3,3,3-trifluoro-propene, (HCFO-1233zd(E), CHCl=CHCF3), (Z)-1-Chloro-3,3,3-trifluoro-propene, (HCFO-1233zd(Z), CHCl=CHCF3), HCFO-1224yd(E), HCFO-1224yd(Z), iso-Pentane, n-Pentane, Cyclopentane, n-Hexane, Cyclohexane, Heptane, Methyl formate, Dimethoxymethane, Dimethoxyethane, Propanal, Methanol, Ethanol, Isopropanol, N-Propanol, trans-1,2-Dichloro-ethylene, cis-1,2-Dichloroethylene, 1-Methoxyheptafluoropropane (HFE-7000, CH3OCF2CF2CF3), Methylnonafluorobutyl ether (HFE-71DA,C4F9OCH3), methoxy-nonafluorobutane (HFE-7100, C4F9OCH3, CH3O-3(CF2)-CH3), ethoxy-nonafluorobutane (HFE-7200, CH3CH2OCF2CF2CF2CF3, C4F9OC2H5), dodecafluoro-2-methylpentan-3-one (NOVEC-649 or Novec-1230, CF3CF2C(O)CF(CF3)2), 1,1,1,2,2,3,4,5,5,5-decafluoro-3-methoxy-4-(trifluoromethyl)-pentane (Novec-7300; C7H3F, 13 O; n-C2F5CF(OCH3)CF(CF3)2), siloxane, methyl perfluoroheptene ether, methoxy-perfluoro-heptene ether or MPHE (HFX-110; C7F 13(OCH3)), MPPE (HFX - 75), perfluorohepta - 2 - ene / perfluorohepta - 3 - ene (HFO - 161 - 14myy / HFO - 161 - 14mcyy, PFH, mixture, CF3CF = CFCF2CF2CF2CF3 / CF3CF2CF = CFCF2CF2CF3), perfluorohepta - 1 - ene (FC - 141 - 10cy, CF2 = CFCF2CF2CF2CF2CF3), 1 - bromo - 1,2,3,3,3 - pentafluoropropene, (R - 1215ybB, CF3CF = CFBr), 2 - bromo - 1,1,1,3,3 - pentafluoro - 2 - propene, (R - 1215xbB1, CF3CBr = CF2), (E) - 1 - bromo - 2,3,3,3 - tetrafluoropropene, (HBFO - 1224ydB(E), CF3CF = CHBr), (Z) - 1 - bromo - 2,3,3,3 - tetrafluoropropene, (HBFO - 1224ydB(Z), CF3CF = CHBr), 2 - bromo - 3,3,3 - trifluoro - propene, (BFO - 1233xfB, CF3CBr = CH2), trans - DCE / R - 1336mzz(Z) mixture, (suitable mixtures include those disclosed in WO 2008 / 134061), (trans - DCE / methyl perfluoroheptene ether, (suitable mixtures include those disclosed in US Patent Publication No. 2012 / 0227764(A1)), (trans - DCE / HFC - 43 - 10mee mixture, (CHCl = CHCl / CF3CHFCHFCF2CF3), (suitable mixtures include those disclosed as disclosed in US Patent No. 5,196,137)), 2 - bromo - 2 - chloro - 1,1,1 - trifluoroethane, (R - 123B1, CHBrClCF3), 2,3 - dichloro - 3,3 - difluoropropene, (R - 1232xf, CClF2CCl = CH2), (E) - 1,1,4,4 - tetrafluoro - 2 - butene, (R - 1345mzz(E), CHF2CH = CHCHF2), 2 - bromo - 1,1 - difluoroethane, (BDFE, CHF2CH2Br), 1 - chloro - 2,3,3,4,4,4 - hexafluoro - 1 - butene, (HCFO - 1326yd - Z, CF3CF2CF = CHCl), 1 - chloro - 2,3,Comprising at least one of 3-trifluoro-propene, (HCFO-1233yd-Z, CHF2CF=CHCl), 2-(1,1,2,2-tetrafluoroethoxy)-1-fluoroethylene, (HFO-1345ezcEβγ, CFH=CHOCF2CF2H), 2,3,3,3-tetrafluoro-1-(1,1,2,2-tetrafluoroethoxy)prop-1-ene, (HFO-1438mzycEγδ, CF3CF=CHOCF2CF2H), 1-(difluoromethoxy)-2,3,3,3-tetrafluoroprop-1-ene, (HFO-1336pzEαβ, CF3CF=CHOCF2H), 2,3,3-trifluoro-1-(trifluoromethoxy)prop-1-ene, (HFO-1336mzyEαβ, CHF2CF=CHOCF3), 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene, (F22E, C2F5CH=CHC2F5), 1,1,1,2,2,3,3,4,4,7,7,8,8,9,9,10,10,10-octadecafluoro-5-decene, (F44E, C4F9CH=CHC4F9), or 1,1,1,2,3,4,4,5,5,5-decafluoropentane, (HFC-43-10mee, CF3CHFCHFCF2CF3).

[0018] Another embodiment of the present invention relates to a process for recovering heat from a heat source and generating mechanical energy, the process comprising: (a) passing a first working fluid through a heat exchanger or evaporator in a liquid phase, the heat exchanger or evaporator being in communication with a heat source that supplies heat; (b) removing at least a portion of the first working fluid in a gas phase from the heat exchanger or evaporator; (c) passing said at least a portion of the first working fluid through an expander in a gas phase, wherein at least a portion of the heat is converted into mechanical energy; (d) passing at least a portion of the first working fluid from the expander to a condenser in a vapor phase, wherein said at least a portion of the first working fluid in the vapor phase is condensed into a second working fluid in a liquid phase; (e) Optionally, in step (a), a step of compressing and mixing the second working fluid in the liquid phase with the first working fluid in the liquid phase; (f) Optionally, a step of repeating steps (a) to (e) at least once; At least one of the first working fluid or the second working fluid contains a composition containing the compound of formula (4), R f CF3(CX5X6CX7X8) n CH=CHCX9X 10 CX 11 X 12 F(4) In the formula, R f is a C1-C 10 perfluorinated alkyl group, In the formula, X5, X6, X7, X8, X9, X 10 , X 11 and X 12 are each independently H, Cl, or F, and n is an integer of 0 or 1, X5, X6, X7, X8, X9, X 10 , X 11 and X 12 The total number of F represented by is at least 2, and optionally, (E)-1,1,1,4,4,4-Hexafluoro-2-butene, (HFO-1336mzz(E), CF3CH=CHCF3), (Z)-1,1,1,4,4,4-Hexafluoro-2-butene, (HFO-1336mzz(Z), CF3CH=CHCF3), (E)-2,3-Bis(trifluoromethyl)oxirane, (HFO-1336mzz(E)(epoxide), CFCH(-O-)CHCF3), (Z)-2,3-Bis(trifluoromethyl)oxirane, (HFO-1336mzz(Z)(epoxide), CFCH(-O-)CHCF3), HFO-1234ze(Z), HFO-1234ye(E), HFO-1234ye(Z), HFO-1438mzz(E), HFO-1438mzz(Z), Heptafluoro-4-(trifluoromethyl)-penta-2-ene, ((HFO-153-10mzzy), (mixture of HFO-153-10 isomers)), HFO-162-13mcyz, HFO-162-13mczy, (E)-1,3,4,4,4-Pentafluoro-3-(trifluoromethyl)-1-butene, (HFO-1438ezy(E), CFH=CHCF(CF3)2), (Z)-1,3,4,4,4-Pentafluoro-3-(trifluoromethyl)-1-butene, (HFO-1438ezy(Z), CFH=CHCF(CF3)2), HFO-1336ze(E), HFO-1336ze(Z), HFC-245fa, HFC-245ea, HFC-365mfc, HFC-43-10mee, (E)-1-Chloro-3,3,3-trifluoro-propene, (HCFO-1233zd(E), CHCl=CHCF3), (Z)-1-Chloro-3,3,3-trifluoro-propene, (HCFO-1233zd(Z), CHCl=CHCF3), HCFO-1224yd(E), HCFO-1224yd(Z), Iso-pentane, n-pentane, Cyclopentane, n-hexane, Cyclohexane, Heptane, Methyl formate, Dimethoxymethane, Dimethoxyethane, Propanal, Methanol, Ethanol, Isopropanol, N-propanol, trans-1,2-Dichloro-ethylene, cis-1,2-Dichloroethylene, 1-Methoxyheptafluoropropane (HFE-7000, CH3OCF2CF2CF3), Methyl nonafluorobutyl ether (HFE-71DA,C4F9OCH3), methoxy-nonafluorobutane (HFE-7100, C4F9OCH3, CH3O-3(CF2)-CH3), ethoxy-nonafluorobutane (HFE-7200, CH3CH2OCF2CF2CF2CF3, C4F9OC2H5), dodecafluoro-2-methylpentan-3-one (NOVEC-649 or Novec-1230, CF3CF2C(O)CF(CF3)2), 1,1,1,2,2,3,4,5,5,5-decafluoro-3-methoxy-4-(trifluoromethyl)-pentane (Novec-7300; C7H3F, 13 O; n-C2F5CF(OCH3)CF(CF3)2), siloxane, methyl perfluoroheptene ether, methoxy-perfluoro-heptene ether or MPHE (HFX-110; C7F 13(OCH3)), MPPE (HFX-75), perfluorohepta-2-ene / perfluorohepta-3-ene (HFO-161-14myy / HFO-161-14mcyy, PFH, mixture, CF3CF=CFCF2CF2CF2CF3 / CF3CF2CF=CFCF2CF2CF3), perfluorohepta-1-ene (FC-141-10cy, CF2=CFCF2CF2CF2CF2CF3), 1-bromo-1,2,3,3,3-pentafluoropropene, (R-1215ybB, CF3CF=CFBr), 2-bromo-1,1,1,3,3-pentafluoro-2-propene, (R-1215xbB1, CF3CBr=CF2), (E)-1-bromo-2,3,3,3-tetrafluoropropene, (HBFO-1224ydB(E), CF3CF=CHBr), (Z)-1-bromo-2,3,3,3-tetrafluoropropene, (HBFO-1224ydB(Z), CF3CF=CHBr), 2-bromo-3,3,3-trifluoro-propene, (BFO-1233xfB, CF3CBr=CH2), trans-DCE / R-1336mzz(Z) mixture, (suitable mixtures include those disclosed in WO 2008 / 134061), (trans-DCE / methyl perfluoroheptene ether, (suitable mixtures include those disclosed in US Patent Publication No. 2012 / 0227764(A1)), (trans-DCE / HFC-43-10mee mixture, (CHCl=CHCl / CF3CHFCHFCF2CF3), (suitable mixtures include those disclosed as disclosed in US Patent No. 5196137)), 2-bromo-2-chloro-1,1,1-trifluoroethane, (R-123B1, CHBrClCF3), 2,3-dichloro-3,3-difluoropropene, (R-1232xf, CClF2CCl=CH2), (E)-1,1,4,4-tetrafluoro-2-butene, (R-1345mzz(E), CHF2CH=CHCHF2), 2-bromo-1,1-difluoroethane, (BDFE, CHF2CH2Br), 1-chloro-2,3,3,4,4,4-hexafluoro-1-butene, (HCFO-1326yd-Z, CF3CF2CF=CHCl), 1-chloro-2,3,A co-compound comprising at least one of 3-trifluoro-propene, (HCFO-1233yd-Z, CHF2CF=CHCl), 2-(1,1,2,2-tetrafluoroethoxy)-1-fluoroethylene, (HFO-1345ezcEβγ, CFH=CHOCF2CF2H), 2,3,3,3-tetrafluoro-1-(1,1,2,2-tetrafluoroethoxy)prop-1-ene, (HFO-1438mzycEγδ, CF3CF=CHOCF2CF2H), 1-(difluoromethoxy)-2,3,3,3-tetrafluoroprop-1-ene, (HFO-1336pzEαβ, CF3CF=CHOCF2H), 2,3,3-trifluoro-1-(trifluoromethoxy)prop-1-ene, (HFO-1336mzyEαβ, CHF2CF=CHOCF3), 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene, (F22E, C2F5CH=CHC2F5), 1,1,1,2,2,3,3,4,4,7,7,8,8,9,9,10,10,10-octadecafluoro-5-decene, (F44E, C4F9CH=CHC4F9), or 1,1,1,2,3,4,4,5,5,5-decafluoropentane, (HFC-43-10mee, CF3CHFCHFCF2CF3).

[0019] In another embodiment of the invention, the apparatus includes: (a) a first heat exchanger through which a working fluid flows and is heated; (b) a compressor in fluid communication with the first heat exchanger that compresses the heated working fluid to a higher pressure; (c) a second heat exchanger in fluid communication with the compressor through which the high-pressure working fluid flows and is cooled; and (d) a pressure reducing device in fluid communication with the second heat exchanger that reduces the pressure of the cooled working fluid and is further in fluid communication with an evaporator such that the working fluid repeatedly flows through components (a), (b), (c), and (d) in a cycle later.

[0020] One embodiment of the present invention relates to any combination of the foregoing embodiments, wherein at least one of the first working fluid or the second working fluid includes a composition containing a compound of formula (4). R f CF3(CX5X6CX7X8) nCH=CHCX9X 10 CX 11 X 12 F(4) wherein, R f is a C1-C 10 perfluorinated alkyl group, wherein, X5, X6, X7, X8, X9, X 10 , X 11 and X 12 are each independently H, Cl, or F, n is an integer of 0 or 1, X5, X6, X7, X8, X9, X 10 , X 11 and X 12 the total number of F represented by is at least 2, and optionally, (E)-1,1,1,4,4,4-Hexafluoro-2-butene, (HFO-1336mzz(E), CF3CH=CHCF3), (Z)-1,1,1,4,4,4-Hexafluoro-2-butene, (HFO-1336mzz(Z), CF3CH=CHCF3), (E)-2,3-Bis(trifluoromethyl)oxirane, (HFO-1336mzz(E)(epoxide), CFCH(-O-)CHCF3), (Z)-2,3-Bis(trifluoromethyl)oxirane, (HFO-1336mzz(Z)(epoxide), CFCH(-O-)CHCF3), HFO-1234ze(Z), HFO-1234ye(E), HFO-1234ye(Z), HFO-1438mzz(E), HFO-1438mzz(Z), Heptafluoro-4-(trifluoromethyl)-penta-2-ene, ((HFO-153-10mzzy), (mixture of HFO-153-10 isomers)), HFO-162-13mcyz, HFO-162-13mczy, (E)-1,3,4,4,4-Pentafluoro-3-(trifluoromethyl)-1-butene, (HFO-1438ezy(E), CFH=CHCF(CF3)2), (Z)-1,3,4,4,4-Pentafluoro-3-(trifluoromethyl)-1-butene, (HFO-1438ezy(Z), CFH=CHCF(CF3)2), HFO-1336ze(E), HFO-1336ze(Z), HFC-245fa, HFC-245ea, HFC-365mfc, HFC-43-10mee, (E)-1-Chloro-3,3,3-trifluoro-propene, (HCFO-1233zd(E), CHCl=CHCF3), (Z)-1-Chloro-3,3,3-trifluoro-propene, (HCFO-1233zd(Z), CHCl=CHCF3), HCFO-1224yd(E), HCFO-1224yd(Z), Iso-pentane, n-pentane, Cyclopentane, n-hexane, Cyclohexane, Heptane, Methyl formate, Dimethoxymethane, Dimethoxyethane, Propanal, Methanol, Ethanol, Isopropanol, N-propanol, trans-1,2-Dichloro-ethylene, cis-1,2-Dichloro-ethylene, 1-Methoxyheptafluoropropane (HFE-7000, CH3OCF2CF2CF3), Methyl nonafluorobutyl ether (HFE-71DA,C4F9OCH3), methoxy-nonafluorobutane (HFE-7100, C4F9OCH3, CH3O-3(CF2)-CH3), ethoxy-nonafluorobutane (HFE-7200, CH3CH2OCF2CF2CF2CF3, C4F9OC2H5), dodecafluoro-2-methylpentan-3-one (NOVEC-649 or Novec-1230, CF3CF2C(O)CF(CF3)2), 1,1,1,2,2,3,4,5,5,5-decafluoro-3-methoxy-4-(trifluoromethyl)-pentane (Novec-7300; C7H3F, 13 O; n-C2F5CF(OCH3)CF(CF3)2), siloxane, methyl perfluoroheptene ether, methoxy-perfluoro-heptene ether or MPHE (HFX-110; C7F 13(OCH3)), MPPE (HFX - 75), perfluorohepta - 2 - ene / perfluorohepta - 3 - ene (HFO - 161 - 14myy / HFO - 161 - 14mcyy, PFH, mixture, CF3CF = CFCF2CF2CF2CF3 / CF3CF2CF = CFCF2CF2CF3), perfluorohepta - 1 - ene (FC - 141 - 10cy, CF2 = CFCF2CF2CF2CF2CF3), 1 - bromo - 1,2,3,3,3 - pentafluoropropene, (R - 1215ybB, CF3CF = CFBr), 2 - bromo - 1,1,1,3,3 - pentafluoro - 2 - propene, (R - 1215xbB1, CF3CBr = CF2), (E) - 1 - bromo - 2,3,3,3 - tetrafluoropropene, (HBFO - 1224ydB(E), CF3CF = CHBr), (Z) - 1 - bromo - 2,3,3,3 - tetrafluoropropene, (HBFO - 1224ydB(Z), CF3CF = CHBr), 2 - bromo - 3,3,3 - trifluoro - propene, (BFO - 1233xfB, CF3CBr = CH2), trans - DCE / R - 1336mzz(Z) mixture, (preferred mixtures include those disclosed in WO 2008 / 134061), (trans - DCE / methyl perfluoroheptene ether, (preferred mixtures include those disclosed in US 2012 / 0227764(A1)), (trans - DCE / HFC - 43 - 10mee mixture, (CHCl = CHCl / CF3CHFCHFCF2CF3), (suitable mixtures include those disclosed as disclosed in US Pat. No. 5,196,137)), 2 - bromo - 2 - chloro - 1,1,1 - trifluoroethane, (R - 123B1, CHBrClCF3), 2,3 - dichloro - 3,3 - difluoropropene, (R - 1232xf, CClF2CCl = CH2), (E) - 1,1,4,4 - tetrafluoro - 2 - butene, (R - 1345mzz(E), CHF2CH = CHCHF2), 2 - bromo - 1,1 - difluoroethane, (BDFE, CHF2CH2Br), 1 - chloro - 2,3,3,4,4,4 - hexafluoro - 1 - butene, (HCFO - 1326yd - Z, CF3CF2CF = CHCl), 1 - chloro - 2,3,Comprising a co-compound containing at least one of 3-trifluoro-propene, (HCFO-1233yd-Z, CHF2CF=CHCl), 2-(1,1,2,2-tetrafluoroethoxy)-1-fluoroethylene, (HFO-1345ezcEβγ, CFH=CHOCF2CF2H), 2,3,3,3-tetrafluoro-1-(1,1,2,2-tetrafluoroethoxy)prop-1-ene, (HFO-1438mzycEγδ, CF3CF=CHOCF2CF2H), 1-(difluoromethoxy)-2,3,3,3-tetrafluoroprop-1-ene, (HFO-1336pzEαβ, CF3CF=CHOCF2H), 2,3,3-trifluoro-1-(trifluoromethoxy)prop-1-ene, (HFO-1336mzyEαβ, CHF2CF=CHOCF3), 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene, (F22E, C2F5CH=CHC2F5), 1,1,1,2,2,3,3,4,4,7,7,8,8,9,9,10,10,10-octadecafluoro-5-decene, (F44E, C4F9CH=CHC4F9), or 1,1,1,2,3,4,4,5,5,5-decafluoropentane, (HFC-43-10mee, CF3CHFCHFCF2CF3).

[0021] In one embodiment, the process for transferring heat includes providing an article and contacting the article with a heat transfer medium. The heat transfer medium is a compound of formula (4), R f CF3(CX5X6CX7X8) n CH=CHCX9X 10 CX 11 X 12 and a composition containing a compound of F. In the compound of formula (4), R f is a C1-C 10 perfluorinated alkyl group, and X5, X6, X7, X8, X9, X 10 , X 11 and X 12 are each independently H, Cl, or F, n is an integer of 0 or 1, and the total number of F represented by X5, X6, X7, X8, X9, X 10 , X 11 and X 12 is at least 2.

[0022] The heat transfer medium can further contain one or more co-compounds.

[0023] In another embodiment, the process for transferring heat includes providing an article and contacting the article with a heat transfer medium. The heat transfer medium is a compound of formula (1), R f CH=CHF is contacted with a fluorinated ethylene compound of formula (2), CX1X2=CX3X4, to form a composition containing the composition. In the compound of formula (1), R f is a C1-C 10 perfluorinated alkyl group. In the compound of formula (2), X1, X2, X3, and X4 are each independently H, Cl, or F, and at least one of X1, X2, X3, or X4 is F. The contact is carried out in the presence of a Lewis acid catalyst in an amount sufficient to form a composition containing a compound of formula (3), R f CF3(CX5X6CX7X8) n CH=CHCX9X 10 CX 11 X 12 F. In the compound of formula (3), X5, X6, X7, X8, X9, X 10 、X 11 and X 12 are each independently H, Cl, or F, and the total number of H, Cl, and F represented by X5, X6, X7, X8, X9, X 10 、X 11 and X 12 is the same as the total number of H, Cl, and F provided by the fluorinated ethylene compound of formula (2).

[0024] The heat transfer medium can further contain one or more co-compounds.

[0025] In another embodiment, the process for treating a surface includes providing a surface and contacting the surface with a treatment composition. The surface includes a material capable of being treated deposited thereon. The treatment composition includes a composition containing 1,1,1,2,2,5,5,6,6,7,7,7-dodecafluorohepta-2-ene, C3F7CH=CHC2F5 (F23E).

[0026] The treatment composition can further include one or more co-compounds.

[0027] In another embodiment, a refrigerant system includes an evaporator, a condenser, a compressor, an expansion device, and a heat transfer medium. The heat transfer medium includes a composition containing 1,1,1,2,2,5,5,6,6,7,7,7-dodecafluorohepta-2-ene, C3F7CH=CHC2F5 (F23E).

[0028] The treatment composition can further include one or more co-compounds.

[0029] In another embodiment, a heat pipe system includes a heat pipe having a working fluid therein. The working fluid includes a composition containing 1,1,1,2,2,5,5,6,6,7,7,7-dodecafluorohepta-2-ene, C3F7CH=CHC2F5 (F23E).

[0030] The working fluid can further include one or more co-compounds.

[0031] In another embodiment, a process for transferring heat includes providing an article and contacting the article with a heat transfer medium. The heat transfer medium includes a composition containing a compound of formula (4), R f CF3(CX5X6CX7X8) n CH=CHCX9X 10 CX 11 X 12 F(4). In the compound of formula (4), R f is a C1-C 10 perfluorinated alkyl group, and X5, X6, X7, X8, X9, X 10 , X 11 and X12 is independently H, Cl, or F, n is an integer of 0 or 1, and the total number of F represented by X5, X6, X7, X8, X9, X 10 , X 11 and X 12 is at least 2.

[0032] The heat transfer medium can further contain one or more co-compounds.

[0033] Suitable co-compounds useful with the above-described working fluid, treatment compound, and heat transfer medium include (E)-1,1,1,4,4,4-hexafluoro-2-butene, (HFO-1336mzz(E), CF3CH=CHCF3), (Z)-1,1,1,4,4,4-hexafluoro-2-butene, (HFO-1336mzz(Z), CF3CH=CHCF3), (E)-2,3-bis(trifluoromethyl)oxirane, (HFO-1336mzz(E)(epoxide), CFCH(-O-)CHCF3), (Z)-2,3-bis(trifluoromethyl)oxirane, (HFO-1336mzz(Z)(epoxide), CFCH(-O-)CHCF3), HFO-1234ze(Z), HFO-1234ye(E), HFO-1234ye(Z), HFO-1438mzz(E), HFO-1438mzz(Z), heptafluoro-4-(trifluoromethyl)-penta-2-ene, ((HFO-153-10mzzy), (mixture of HFO-153-10 isomers)), HFO-162-13mcyz, HFO-162-13mczy, (E)-1,3,4,4,4-pentafluoro-3-(trifluoromethyl)-1-butene, (HFO-1438ezy(E), CFH=CHCF(CF3)2), (Z)-1,3,4,4,4-pentafluoro-3-(trifluoromethyl)-1-butene, (HFO-1438ezy(Z), CFH=CHCF(CF3)2), HFO-1336ze(E), HFO-1336ze(Z), HFC-245fa, HFC-245ea, HFC-365mfc, HFC-43-10mee, (E)-1-chloro-3,3,3-trifluoro-propene, (HCFO-1233zd(E), CHCl=CHCF3), (Z)-1-chloro-3,3,3-trifluoro-propene, (HCFO-1233zd(Z), CHCl=CHCF3), HCFO-1224yd(E), HCFO-1224yd(Z), iso-pentane, n-pentane, cyclopentane, n-hexane, cyclohexane, heptane, methyl formate, dimethoxymethane, dimethoxyethane, propanal, methanol, ethanol, isopropanol, N-propanol, trans-1,2-dichloro-ethylene, cis-1,2-dichloro-ethylene, 1-methoxyheptafluoropropane (HFE-7000,CH3OCF2CF2CF3), methyl nonafluorobutyl ether (HFE-71DA, C4F9OCH3), methoxy-nonafluorobutane (HFE-7100, C4F9OCH3, CH3O-3(CF2)-CH3), ethoxy-nonafluorobutane (HFE-7200, CH3CH2OCF2CF2CF2CF3, C4F9OC2H5), dodecafluoro-2-methylpentan-3-one (NOVEC-649 or Novec-1230, CF3CF2C(O)CF(CF3)2), 1,1,1,2,2,3,4,5,5,5-decafluoro-3-methoxy-4-(trifluoromethyl)-pentane (Novec-7300; C7H3F, 13 O; n-C2F5CF(OCH3)CF(CF3)2), siloxane, methyl perfluoroheptene ether, methoxy-perfluoro-heptene ether or MPHE (HFX-110; C7F 13(OCH3)), MPPE (HFX - 75), perfluorohepta - 2 - ene / perfluorohepta - 3 - ene (HFO - 161 - 14myy / HFO - 161 - 14mcyy, PFH, mixture, CF3CF = CFCF2CF2CF2CF3 / CF3CF2CF = CFCF2CF2CF3), perfluorohepta - 1 - ene (FC - 141 - 10cy, CF2 = CFCF2CF2CF2CF2CF3), 1 - bromo - 1,2,3,3,3 - pentafluoropropene, (R - 1215ybB, CF3CF = CFBr), 2 - bromo - 1,1,1,3,3 - pentafluoro - 2 - propene, (R - 1215xbB1, CF3CBr = CF2), (E) - 1 - bromo - 2,3,3,3 - tetrafluoropropene, (HBFO - 1224ydB(E), CF3CF = CHBr), (Z) - 1 - bromo - 2,3,3,3 - tetrafluoropropene, (HBFO - 1224ydB(Z), CF3CF = CHBr), 2 - bromo - 3,3,3 - trifluoro - propene, (BFO - 1233xfB, CF3CBr = CH2), trans - DCE / R - 1336mzz(Z) mixture, (suitable mixtures include those disclosed in WO 2008 / 134061), (trans - DCE / methyl perfluoroheptene ether, (suitable mixtures include those disclosed in US Patent Publication No. 2012 / 0227764(A1)), (trans - DCE / HFC - 43 - 10mee mixture, (CHCl = CHCl / CF3CHFCHFCF2CF3), (suitable mixtures include those disclosed as disclosed in US Patent No. 5,196,137)), 2 - bromo - 2 - chloro - 1,1,1 - trifluoroethane, (R - 123B1, CHBrClCF3), 2,3 - dichloro - 3,3 - difluoropropene, (R - 1232xf, CClF2CCl = CH2), (E) - 1,1,4,4 - tetrafluoro - 2 - butene, (R - 1345mzz(E), CHF2CH = CHCHF2), 2 - bromo - 1,1 - difluoroethane, (BDFE, CHF2CH2Br), 1 - chloro - 2,3,3,4,4,4 - hexafluoro - 1 - butene, (HCFO - 1326yd - Z, CF3CF2CF = CHCl), 1 - chloro - 2,3,It includes 3-trifluoro-propene, (HCFO-1233yd-Z, CHF2CF=CHCl), 2-(1,1,2,2-tetrafluoroethoxy)-1-fluoroethylene, (HFO-1345ezcEβγ, CFH=CHOCF2CF2H), 2,3,3,3-tetrafluoro-1-(1,1,2,2-tetrafluoroethoxy)prop-1-ene, (HFO-1438mzycEγδ, CF3CF=CHOCF2CF2H), 1-(difluoromethoxy)-2,3,3,3-tetrafluoroprop-1-ene, (HFO-1336pzEαβ, CF3CF=CHOCF2H), 2,3,3-trifluoro-1-(trifluoromethoxy)prop-1-ene, (HFO-1336mzyEαβ, CHF2CF=CHOCF3), 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene, (F22E, C2F5CH=CHC2F5), 1,1,1,2,2,3,3,4,4,7,7,8,8,9,9,10,10,10-octadecafluoro-5-decene, (F44E, C4F9CH=CHC4F9), or 1,1,1,2,3,4,4,5,5,5-decafluoropentane, (HFC-43-10mee, CF3CHFCHFCF2CF3).

[0034] One embodiment of the present invention relates to a partially regenerated composition formed by any combination of the aforementioned methods.

[0035] The embodiments can be used alone or in combination with each other. Other features and advantages of the present invention will become apparent from the following more detailed description taken in conjunction with the accompanying drawings which illustrate the principles of the invention by way of example.

Brief Description of the Drawings

[0036]

Figure 1

Figure 2

Figure 3

Figure 4

Figure 5

Figure 6

Figure 7

Figure 8

DETAILED DESCRIPTION OF THE INVENTION

[0037] A one-step synthesis for the production of fluorinated alkenes is provided.

[0038] Embodiments of the present disclosure provide a one-step synthesis for the production of fluorinated alkenes, for example, as compared to concepts that may not include one or more of the features disclosed herein. More specifically, the present disclosure provides a one-step synthesis for the production of fluorinated alkenes having perfluorinated alkyl chains.

[0039] The process can be carried out in any reactor suitable for gas-phase fluorination reactions. The reactor is made of a material resistant to the reactants used. The reactor may be constructed from materials resistant to the corrosive effects of hydrogen fluoride, such as stainless steel, Hastelloy®, Inconel®, Monel®, gold or gold wire, or quartz. The reaction may be carried out batchwise, continuously, semi-continuously, or in combinations thereof. Suitable reactors include batch reactor vessels and tubular reactors.

[0040] In one embodiment, a reagent of formula (1) R f CH=CHF(1) wherein R f is C1 to C 10It is a perfluorinated alkyl group, The reactor is filled, heated, and contacted with a fluorinated ethylene compound of formula (2) in the presence of a catalyst, CX1X2=CX3X4(2) wherein X1, X2, X3, and X4 are each independently H, Cl, or F, and at least one of X1, X2, X3, or X4 is F.

[0041] The temperature and pressure of the reactor are maintained at levels sufficient to result in the formation of a composition containing a compound of formula (3) in the presence of a Lewis acid catalyst, R f CF3(CX5X6CX7X8) n CH=CHCX9X 10 CX 11 X 12 F(3) wherein X5, X6, X7, and X8 are each independently H, Cl, or F, and n is an integer of 0 or 1, X5, X6, X7, X8, X9, X 10 、X 11 and X 12 The total number of each of H, Cl, and F represented by is the same as the total number of each of H, Cl, and F provided by the fluorinated ethylene compound of formula (2).

[0042] In some embodiments, the compound of formula (1) includes 1,3,3,3-tetrafluoro-1-propene, CF3CH=CHF (1234ze). In one embodiment, the compound of formula (1) is CF3CH=CHF (1234ze). *

[0043] * * *Note: There seem to be some incomplete or unclear parts in the original text, especially the parts with multiple consecutive short tags and some undefined or incomplete chemical formula fragments. The translation is done based on the best understanding of the provided text.*In some embodiments, the fluorinated ethylene of formula (2) comprises at least one of tetrafluoro-ethene, CF2=CF2 (TFE) or CFCl=CF2 (1-chloro-1,2,2-trifluoro-ethene), CF2=CH2 (1,1-difluoro-ethene), CH2=CHF (1-fluoro-ethene), CF2=CCl2 (1,1-dichloro-2,2-difluoro-ethene), CFCl=CFCl (1,2-dichloro-1,2-difluoro-ethene). In one embodiment, the fluorinated ethylene of formula (2) comprises tetrafluoro-ethene, CF2=CF2 (TFE).

[0044] In one embodiment, the compound of formula (1) comprises CF3CH=CHF (1234ze) and the fluorinated ethylene of formula (2) comprises CF2=CF2 (TFE). The reaction of CF3CH=CHF (1234ze) and CF2=CF2 (TFE) can result in the formation of a composition comprising 1,1,1,4,4,5,5,5-octafluoropent-2-ene, CF3CH=CHC2F5 (F12E).

[0045] If desired, 1,1,1,4,4,5,5,5-octafluoropent-2-ene can be isolated and optionally purified prior to use. Suitable uses of 1,1,1,4,4,5,5,5-octafluoropent-2-ene include, but are not limited to, reactive intermediates, refrigerants, heat transfer fluids, and solvents.

[0046] In some embodiments, the fluorinated ethylene of formula (2) can comprise a plurality of compounds of formula (2). The resulting compound of formula (3) can comprise a plurality of compounds of formula (3). In one embodiment, the fluorinated ethylene of formula (2) may comprise tetrafluoro-ethene, CF2=CF2 (TFE) and 1-chloro-1,2,2-trifluoro-ethene. In a further embodiment, the compound of formula (1) can comprise CF3CH=CHF (1234ze).

[0047] Examples of the resulting compound of formula (3) include 1,1,1,4,4,5,5,5 - octafluoropent - 2 - ene, CF3CH=CHC2F5 (F12E), and 4 - chloro - 1,1,1,4,5,5,5 - heptafluoropent - 2 - ene CF3CH=CHCFClCF3, 5 - chloro - 1,1,1,4,4,5,5 - heptafluoropent - 2 - ene CF3CH=CHCF2CF2Cl, 4,5 - dichloro - 1,1,1,4,5,5 - hexafluoropent - 2 - ene, CF3CH=CHCFClCF2Cl or 1,1,1,5,5,5 - hexafluoropent - 2 - ene CF3CH=CHCH2CF3.

[0048] The molar ratio of the compound of formula (2) and the compound of formula (1) contacted according to the present invention can be used to control the ratio of the composition and the reaction product. In some embodiments, the compound of formula (2) and the compound of formula (1) are contacted in an amount that provides a molar ratio of 0.01:1 to 5:1. In one embodiment, the compound of formula (2) and the compound of formula (1) are contacted in an amount that provides a molar ratio of (2):(1) of 0.1:1 to 2:1. A contact molar ratio of about 1:1 can produce a C5 compound, and a molar ratio of about 2:1 can produce a product C7 compound. Any desired ratio can be used, but a ratio of about 2:1 is useful. In one embodiment, the compound of formula (2) and the compound of formula (1) are contacted in an amount that provides a molar ratio of (2):(1) of 1:1 to 2:1. In one embodiment, the compound of formula (2) is (TFE) and the compound of formula (1) is (1234ze).

[0049] The reaction conditions and stoichiometry may be selected to cause a compound of formula (3) such as the above 1,1,1,4,4,5,5,5 - octafluoropent - 2 - ene, CF3CH=CHC2F5 (F12E) to act as a reactive intermediate. In some embodiments, the fluorinated ethylene of formula (2) may be provided in a stoichiometric excess relative to the amount of the compound of formula (1). In some embodiments, an excess of the compound of formula (2) such as (TFE) may cause one or more additional units of the compound of formula (2) to react with 1,1,1,4,4,5,5,5 - octafluoropent - 2 - ene to form an additional compound of formula (3) having an extended carbon chain. In one embodiment, the composition containing the compound of formula (3) may include 1,1,1,2,2,5,5,6,6,7,7,7 - dodecafluorohept - 2 - ene, C3F7CH=CHC2F5 (F23E).

[0050] The reaction is typically carried out in a closed system. In some embodiments, the Lewis acid is a strong Lewis acid. In one embodiment, the catalyst is aluminum chloride (AlCl3), or antimony pentafluoride (SbF5), or aluminum chlorofluoride AlCl x F 3-x where x may be an integer from 1 to 3 for the aluminum - based catalyst x. In some embodiments, x may be from 0.01 to 0.5. The amount of the catalyst can range from about 0.1 to about 20 wt%, optionally from about 1 to about 15, and optionally from about 5 to about 10 wt% of the reaction mixture.

[0051] Additional suitable strong Lewis acids are described in (Chemical Reviews, 1996, v. 96, pp. 3269-3301, the list of strong Lewis acids that may be described on page 3271, which is incorporated herein by reference). In some embodiments, the reaction mixture is heated to sub-ambient or ambient temperature. In some embodiments, the reaction mixture is heated to a temperature of -50 °C to 50 °C. In one embodiment, the reaction mixture is heated to a temperature of -50 °C to 25 °C. In some embodiments, the reaction is carried out at a reactor pressure of 0.1 pounds per square inch gauge (psig) to 300 pounds per square inch gauge (psig). In one embodiment, the reaction is carried out under autogenous pressure.

[0052] In some embodiments, the formation of the compound of formula (3) may be carried out in the presence of at least one of a solvent or a diluent, depending on whether all components of the reaction mixture are soluble. In some embodiments, the solvent or diluent is a perfluorinated saturated compound. In some embodiments, the perfluorinated saturated compound is perfluoropentane, perfluorohexane, the cyclic dimer of hexafluoropropene (a mixture of perfluoro-1,2- and perfluoro-1,3-dimethylcyclobutane), and combinations thereof, or the reaction product can be used as the reaction medium. The amount of at least one solvent or diluent can range from about 10 to about 50 volume percent, about 15 to 40, and in some cases about 20 to 30 volume percent of the reaction vessel.

[0053] In one particular embodiment, at least one diluent or solvent comprises the reaction product formed by contacting formulas (1) and (2). The reaction product diluent or solvent can be supplied to the reaction environment by recycling a portion of the recovered reaction product in a continuous process and leaving a residual portion of the reaction product in the reaction environment in a batch process, among other suitable techniques for delivering a diluent or solvent to the reaction environment.

[0054] In one embodiment of the present invention, the reaction is carried out in an environment that does not contain or substantially does not contain a compound having an OH group. Examples of such OH-containing compounds are hydrocarbon greases or oils, and solvents having an OH group such as water or alcohol. Substantially not containing means that there are less than 50 ppm, less than 25 ppm, and in some cases less than 10 ppm of OH-containing compounds present.

[0055] The compound of formula (3) can be used in many applications for heat transfer, such as a heat transfer fluid or a refrigerant. In one embodiment, heat is transferred from an article using the compound of formula (3) (for example, a reaction product mixture obtained by contacting the compounds of formulas (1) and (2)). The article can be brought into contact with a heat transfer medium containing at least one compound of formula (3).

[0056] In one embodiment, the heat transfer process may include providing an article and bringing the article into contact with a heat transfer medium. The heat transfer medium includes a composition containing a compound of formula (4), R f CF3(CX5X6CX7X8) n CH=CHCX9X 10 CX 11 X 12 F(4) wherein R f is a C1-C 10 perfluorinated alkyl group, X5, X6, X7 and X8 are each independently H, Cl, or F, n is an integer of 0 or 1, and the total number of F represented by X5, X6, X7, X8, X9, X 10 or X 11 and X 12 is at least 2. In some embodiments, the compound of formula (3) includes 1,1,1,2,2,5,5,6,6,7,7,7 dodecafluorohept-2-ene, C3F7CH=CHC2F5 (F23E).

[0057] The heat transfer medium composition comprises (E)-1,1,1,4,4,4-hexafluoro-2-butene, (HFO-1336mzz(E), CF3CH=CHCF3), (Z)-1,1,1,4,4,4-hexafluoro-2-butene, (HFO-1336mzz(Z), CF3CH=CHCF3), (E)-2,3-bis(trifluoromethyl)oxirane, (HFO-1336mzz(E)(epoxide), CFCH(-O-)CHCF3), (Z)-2,3-bis(trifluoromethyl)oxirane, (HFO-1336mzz(Z)(epoxide), CFCH(-O-)CHCF3), HFO-1234ze(Z), HFO-1234ye(E), HFO-1234ye(Z), HFO-1438mzz(E), HFO-1438mzz(Z), heptafluoro-4-(trifluoromethyl)-penta-2-ene, ((HFO-153-10mzzy), (mixture of HFO-153-10 isomers)), HFO-162-13mcyz, HFO-162-13mczy, (E)-1,3,4,4,4-pentafluoro-3-(trifluoromethyl)-1-butene, (HFO-1438ezy(E), CFH=CHCF(CF3)2), (Z)-1,3,4,4,4-pentafluoro-3-(trifluoromethyl)-1-butene, (HFO-1438ezy(Z), CFH=CHCF(CF3)2), HFO-1336ze(E), HFO-1336ze(Z), HFC-245fa, HFC-245ea, HFC-365mfc, HFC-43-10mee, (E)-1-chloro-3,3,3-trifluoro-propene, (HCFO-1233zd(E), CHCl=CHCF3), (Z)-1-chloro-3,3,3-trifluoro-propene, (HCFO-1233zd(Z), CHCl=CHCF3), HCFO-1224yd(E), HCFO-1224yd(Z), iso-pentane, n-pentane, cyclopentane, n-hexane, cyclohexane, heptane, methyl formate, dimethoxymethane, dimethoxyethane, propanal, methanol, ethanol, isopropanol, N-propanol, trans-1,2-dichloro-ethylene, cis-1,2-dichloro-ethylene, 1-methoxyheptafluoropropane (HFE-7000, CH3OCF2CF2CF3), methyl nonafluorobutyl ether (HFE-71DA,C4F9OCH3), methoxy-nonafluorobutane (HFE-7100, C4F9OCH3, CH3O-3(CF2)-CH3), ethoxy-nonafluorobutane (HFE-7200, CH3CH2OCF2CF2CF2CF3, C4F9OC2H5), dodecafluoro-2-methylpentan-3-one (NOVEC-649 or Novec-1230, CF3CF2C(O)CF(CF3)2), 1,1,1,2,2,3,4,5,5,5-decafluoro-3-methoxy-4-(trifluoromethyl)-pentane (Novec-7300; C7H3F, 13 O; n-C2F5CF(OCH3)CF(CF3)2), siloxane, methyl perfluoroheptene ether, methoxy-perfluoro-heptene ether or MPHE (HFX-110; C7F 13(OCH3), MPPE (HFX-75), perfluorohepta-2-ene / perfluorohepta-3-ene (HFO-161-14myy / HFO-161-14mcyy, PFH, mixture, CF3CF=CFCF2CF2CF2CF3 / CF3CF2CF=CFCF2CF2CF3), perfluorohepta-1-ene (FC-141-10cy, CF2=CFCF2CF2CF2CF2CF3), 1-bromo-1,2,3,3,3-pentafluoropropene, (R-1215ybB, CF3CF=CFBr), 2-bromo-1,1,1,3,3-pentafluoro-2-propene, (R-1215xbB1, CF3CBr=CF2), (E)-1-bromo-2,3,3,3-tetrafluoropropene, (HBFO-1224ydB(E), CF3CF=CHBr), (Z)-1-bromo-2,3,3,3-tetrafluoropropene, (HBFO-1224ydB(Z), CF3CF=CHBr), 2-bromo-3,3,3-trifluoro-propene, (BFO-1233xfB, CF3CBr=CH2), trans-DCE / R-1336mzz(Z) mixture, (suitable mixtures include those disclosed in International Publication No. WO 2008 / 134061), (trans-DCE / methyl perfluoroheptene ether, (suitable mixtures include those disclosed in US Patent Publication No. 2012 / 0227764(A1)), (trans-DCE / HFC-43-10mee mixture, (CHCl=CHCl / CF3CHFCHFCF2CF3), (suitable mixtures include those disclosed as disclosed in US Patent No. 5,196,137)), 2-bromo-2-chloro-1,1,1-trifluoroethane, (R-123B1, CHBrClCF3), 2,3-dichloro-3,3-difluoropropene, (R-1232xf, CClF2CCl=CH2), (E)-1,1,4,4-tetrafluoro-2-butene, (R-1345mzz(E), CHF2CH=CHCHF2), 2-bromo-1,1-difluoroethane, (BDFE, CHF2CH2Br), 1-chloro-2,3,3,4,4,4-hexafluoro-1-butene, (HCFO-1326yd-Z, CF3CF2CF=CHCl), 1-chloro-2,3,One or more co-compounds further comprising at least one of 3-trifluoro-propene, (HCFO-1233yd-Z, CHF2CF=CHCl), 2-(1,1,2,2-tetrafluoroethoxy)-1-fluoroethylene, (HFO-1345ezcEβγ, CFH=CHOCF2CF2H), 2,3,3,3-tetrafluoro-1-(1,1,2,2-tetrafluoroethoxy)prop-1-ene, (HFO-1438mzycEγδ, CF3CF=CHOCF2CF2H), 1-(difluoromethoxy)-2,3,3,3-tetrafluoroprop-1-ene, (HFO-1336pzEαβ, CF3CF=CHOCF2H), 2,3,3-trifluoro-1-(trifluoromethoxy)prop-1-ene, (HFO-1336mzyEαβ, CHF2CF=CHOCF3), 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene, (F22E, C2F5CH=CHC2F5), 1,1,1,2,2,3,3,4,4,7,7,8,8,9,9,10,10,10-octadecafluoro-5-decene, (F44E, C4F9CH=CHC4F9), or 1,1,1,2,3,4,4,5,5,5-decafluoropentane, (HFC-43-10mee, CF3CHFCHFCF2CF3). In some embodiments, the co-compound comprises at least one of HFO-1336mzz(E), HFO-1336mzz(Z), HFO-1234ze(Z), HFO-1234ye(E), HFO-1234ye(Z), or ethanol.,

[0058] In one embodiment, the heat transfer process may include providing an article and contacting the article with a heat transfer medium. The heat transfer medium includes a composition formed by a process that includes contacting a compound of formula (1), R f CH=CHF(1) wherein R f is a C1-C 10 perfluorinated alkyl group and is a fluorinated ethylene compound of formula (2), CX1X2=CX3X4(2) Wherein, X1, X2, X3 and X4 are each independently H, Cl, or F, and at least one of X1, X2, X3 or X4 is F. The process is carried out in the presence of a Lewis acid catalyst in an amount sufficient to form a composition comprising the compound of formula (3). R f CF3(CX5X6CX7X8) n CH=CHCX9X 10 CX 11 X 12 F(3) Wherein, X5, X6, X7 and X8 are each independently H, Cl, or F, n is an integer of 0 or 1, and the total number of each of H, Cl, and F represented by X5, X6, X7, X8, X9, X 10 , X 11 and X 12 is the same as the total number of each of H, Cl, and F provided by the fluorinated ethylene compound of formula (2). In some embodiments, the compound of formula (3) includes 1,1,1,2,2,5,5,6,6,7,7,7 dodecafluorohept-2-ene, C3F7CH=CHC2F5 (F23E).

[0059] Those skilled in the art will understand that during the reaction of the compound of formula (1) with the compound of formula (2), bond formation can occur at any carbon of the compound of formula (2). In some embodiments, this can result in a mixture of isomers. In some embodiments, one isomer can be predominant.

[0060] The heat transfer medium composition may further optionally contain one or more co-compounds. In one embodiment, the co-compound may be one of the above co-compounds.

[0061] In one embodiment, the heat transfer process may include providing a surface and treating the surface by contacting the surface with a treatment composition. The treatment composition includes a composition formed by a process of contacting the compound of formula (1), R f CH=CHF(1) Wherein, R f is C1 to C 10It is a perfluorinated alkyl group and is a fluorinated ethylene compound of formula (2). CX1X2=CX3X4(2) In the formula, X1, X2, X3, and X4 are each independently H, Cl, or F, and at least one of X1, X2, X3, or X4 is F. It is carried out in a sufficient amount in the presence of a Lewis acid catalyst to form a composition containing a compound of formula (3). R f CF3(CX5X6CX7X8) n CH=CHCX9X 10 CX 11 X 12 F(3) In the formula, X5, X6, X7, and X8 are each independently H, Cl, or F, n is an integer of 0 or 1, and the total number of H, Cl, and F represented by X5, X6, X7, X8, X9, X 10 , X 11 and X 12 is the same as the total number of H, Cl, and F provided by the fluorinated ethylene compound of formula (2). In some embodiments, the compound of formula (3) includes 1,1,1,2,2,5,5,6,6,7,7,7 dodecafluorohept-2-ene, C3F7CH=CHC2F5 (F23E).

[0062] The surface treatment composition may further optionally contain one or more co-compounds. In one embodiment, the co-compound may be the above co-compound.

[0063] In other embodiments, the heat transfer system may include a refrigerant system. The refrigerant system includes an evaporator, a condenser, a compressor, an expansion device, and a heat transfer medium. The heat transfer medium includes a composition formed by a process of contacting a compound of formula (1). R f CH=CHF(1) In the formula, R f is a C1-C 10 perfluorinated alkyl group and includes a fluorinated ethylene compound of formula (2). CX1X2=CX3X4(2) Wherein, X1, X2, X3 and X4 are each independently H, Cl, or F, and at least one of X1, X2, X3 or X4 is F. The process is carried out in the presence of a Lewis acid catalyst in an amount sufficient to form a composition comprising the compound of formula (3). R f CF3(CX5X6CX7X8) n CH=CHCX9X 10 CX 11 X 12 F(3) Wherein, X5, X6, X7 and X8 are each independently H, Cl, or F, n is an integer of 0 or 1, and the total number of each of H, Cl, and F represented by X5, X6, X7, X8, X9, X 10 , X 11 and X 12 is the same as the total number of each of H, Cl, and F provided by the fluorinated ethylene compound of formula (2). In some embodiments, the compound of formula (3) includes 1,1,1,2,2,5,5,6,6,7,7,7 dodecafluorohept-2-ene, C3F7CH=CHC2F5 (F23E).

[0064] In some embodiments, the condenser operates at a temperature above 100 °C, above 150 °C, above 175 °C, and / or above 200 °C.

[0065] The heat transfer medium may further optionally contain one or more co-compounds. In one embodiment, the co-compound may be one of the above co-compounds.

[0066] In one embodiment, it is a heat pipe system including a heat pipe having a working fluid inside. The working fluid contains a composition formed by a process of contacting with the compound of formula (1), R f CH=CHF(1) Wherein, R f is a C1-C 10 perfluorinated alkyl group, is a fluorinated ethylene compound of formula (2), CX1X2=CX3X4(2) wherein X1, X2, X3, and X4 are each independently H, Cl, or F, and at least one of X1, X2, X3, or X4 is reacted in the presence of a Lewis acid catalyst in a sufficient amount to form a composition comprising a compound of formula (3). R f CF3(CX5X6CX7X8) n CH=CHCX9X 10 CX 11 X 12 F(3) In the formula, X5, X6, X7, and X8 are each independently H, Cl, or F, n is an integer of 0 or 1, and X5, X6, X7, X8, X9, and X 10 , X 11 and X 12 is the same as the total number of H, Cl, and F provided by the fluorinated ethylene compound of Formula (2). In some embodiments, the compound of Formula (3) comprises 1,1,1,2,2,5,5,6,6,7,7,7 dodecafluorohept-2-ene, C3F7CH=CHC2F5(FE).

[0067] The working fluid may further optionally include one or more co-compounds, which in one embodiment may be one of the co-compounds described above.

[0068] In some embodiments, the compound of Formula (3) undergoes a phase transition from a liquid to a gas state at a temperature of at least 25° C., at least 30° C., at least 40° C., at least 50° C., at least 60° C., less than 140° C., less than 130° C., less than 120° C., less than 110° C., less than 100° C., less than 90° C., less than 80° C., less than 70° C., and combinations thereof. In one embodiment, the compound of Formula (3) undergoes a phase transition from a liquid to a gas state at a temperature between 50° C. and 90° C. In one embodiment, the compound of Formula (3) undergoes a phase transition from a liquid to a gas state at a temperature between 75° C. and 80° C.

[0069] In some embodiments, one or more co-compounds, if present, also undergo a phase transition from a liquid to a gaseous state at a temperature within the above range. In some embodiments, one or more co-compounds undergo a phase transition from a liquid to a gaseous state at a temperature within about 5 °C of the temperature of the phase transition from the liquid to the gaseous state of the compound of formula (3). In one embodiment, the co-compound undergoes a phase transition from a liquid to a gaseous state at a temperature within 3 °C of the temperature of the phase transition from the liquid to the gaseous state of the compound of formula (3).

[0070] In further embodiments, any of the compositions disclosed herein may be used in combination with at least one lubricant selected from the group consisting of polyalkylene glycols, polyol esters, polyvinyl ethers, mineral oils, alkylbenzenes, synthetic paraffins, synthetic naphthenes, poly(alpha)olefins.

[0071] In one embodiment, the lubricants include those suitable for use with refrigeration or air conditioning devices. These lubricants include those conventionally used in vapor compression refrigeration devices that utilize chlorofluorocarbon refrigerants. In one embodiment, the lubricants include those generally known as "mineral oils" in the field of compression refrigeration lubrication. Mineral oils include paraffins (i.e., saturated hydrocarbons with straight-chain and branched carbon chains), naphthenes (i.e., cyclic paraffins), and aromatics (i.e., unsaturated cyclic hydrocarbons containing one or more rings characterized by alternating double bonds). In one embodiment, the lubricants include those generally known as "synthetic oils" in the field of compression refrigeration lubrication. Synthetic oils include alkyl aromatics (i.e., alkyl benzenes with straight-chain and branched alkyls), synthetic paraffins and naphthenes, and poly(alpha olefins). Representative conventional lubricants are commercially available BVM 100 N (a paraffinic mineral oil sold by BVA Oils), naphthenic mineral oils commercially available from Crompton Co. under the trade names Suniso® 3GS and Suniso® 5GS, naphthenic mineral oils commercially available from Pennzoil under the trade name Sontex® 372LT, naphthenic mineral oils commercially available from Calumet Lubricants under the trade name Calumet® RO-30, linear alkyl benzenes commercially available from Shrieve Chemicals under the trade names Zerol® 75, Zerol® 150, and Zerol® 500, and HAB22 (a branched alkyl benzene sold by Nippon Oil).

[0072] In other embodiments, the lubricant is designed for use with hydrofluorocarbon refrigerants and may include those that are miscible with the refrigerants of the present invention under the operating conditions of compression refrigeration and air conditioning equipment. Such lubricants may include, but are not limited to, polyol esters (POE) such as Castrol® 100 (Castrol, United Kingdom), polyalkylene glycols (PAG) such as RL-488A manufactured by Dow (Dow Chemical, Midland, Michigan), polyvinyl ethers (PVE), and polycarbonates (PC).

[0073] The lubricant used with the compositions disclosed herein is selected by considering the requirements of a given compressor and the environment to which the lubricant will be exposed.

[0074] In one embodiment, the compositions disclosed herein may further include additives selected from the group consisting of compatibilizers, UV dyes, solubilizers, tracers, stabilizers, perfluoropolyethers (PFPE), and functionalized perfluoropolyethers.

[0075] In one embodiment, the composition may further include from about 0.01 weight percent to about 5 weight percent of a stabilizer, free radical scavenger, or antioxidant. Such other additives may include, but are not limited to, nitromethane, hindered phenol, hydroxylamine, thiol, phosphite, or lactone. A single additive or a combination may be used.

[0076] In an alternative embodiment, the compound of formula (1) may be dimerized. The compound of formula (1) can be reacted with itself in the absence of the fluorinated ethylene compound of formula (2) in the presence of a catalyst such as antimony pentafluoride (SbF5). In some embodiments, the reaction can be carried out in the presence of a solvent. Suitable solvents include those described above.

[0077] In one example of an alternative embodiment, the dimer may be formed by reacting 1,3,3,3 - tetrafluoro - 1 - propene, CF3CH=CHF (1234ze), as shown below.

[0078]

Chemical formula

[0079] In one embodiment, the above - described composition may be used in combination with a cooling device, which is referred to herein as a chiller. In one embodiment, the chiller may be a vapor - compression chiller. Such a vapor - compression chiller may be either a flooded evaporator chiller shown in FIG. 1 or a direct - expansion chiller shown in FIG. 2. Both the flooded evaporator chiller and the direct - expansion chiller may be air - cooled or water - cooled. In embodiments where the chiller is water - cooled, such a chiller is generally associated with a cooling tower for heat removal from the system. In embodiments where the chiller is air - cooled, the chiller is equipped with a finned - tube condenser coil and a fan for transferring heat from the refrigerant to the air to remove heat from the system. Air - cooled chiller systems are generally less expensive than a comparable - capacity water - cooled chiller system that includes a cooling tower and a water pump. However, water - cooled systems can be more efficient under many operating conditions because of the lower condensation temperature.

[0080] Chillers that include both flooded evaporators and direct - expansion chillers can be associated with an air - conditioning and distribution system that provides comfortable air - conditioning (cooling and dehumidifying air) in large commercial facilities such as hotels, office buildings, hospitals, universities, etc. In another embodiment, the chiller, most likely an air - cooled direct - expansion chiller, has found further utility in naval submarines and surface ships.

[0081] To show how a chiller operates using the composition of the present invention, reference is made to the drawings. A water-cooled flooded evaporator chiller is shown in FIG. 1. In this chiller, a first cooling medium, which is a warm liquid containing water and which, in some embodiments, contains additives such as glycol (e.g., ethylene glycol or propylene glycol), enters the chiller from a cooling system such as a configured cooling system, as shown by arrow 3 through coil 9 in evaporator 6 having an inlet and an outlet. The warm first cooling medium is distributed to the evaporator where it is cooled by the liquid refrigerant. This is shown at the cooler part of the evaporator. The liquid refrigerant evaporates at a temperature lower than the temperature of the warm first cooling medium flowing through coil 9. The cooled first cooling medium returns through the return bend of coil 9 and recirculates to the configured cooling system as shown by arrow 4. The liquid refrigerant evaporates and is drawn into compressor 7 as shown at the cooler part of evaporator 6 in FIG. 1, increasing the pressure and temperature of the refrigerant vapor. The compressor compresses this vapor so that it can be condensed in condenser 5 at high pressure and high temperature, higher than the pressure and temperature at which the vapor exits the evaporator. A second cooling medium, which is a liquid in the case of a water-cooled chiller, enters the condenser from the cooling tower of arrow 1 in FIG. 1 through coil 10 in condenser 5. The second cooling medium is warmed in the process and returned to the cooling tower or the environment through coil 10 and the return loop of arrow 2. This second cooling medium cools the vapor in the condenser, causing the condensation of the vapor into liquid refrigerant, whereby, at the cooler part of the condenser, there is liquid refrigerant as shown in FIG. 1. The liquid refrigerant condensed in the condenser flows through expansion device 8 and returns to the evaporator. Examples of this device may include an orifice, a capillary tube, or an expansion valve. Expansion device 8 reduces the pressure of the liquid refrigerant and partially converts the liquid refrigerant into vapor. That is, when the pressure drops between the condenser and the evaporator, the liquid refrigerant can be said to spurt out. The spurt cools the refrigerant, that is, both the liquid refrigerant and the refrigerant vapor, to the saturation temperature at the pressure of the evaporator, whereby both the liquid refrigerant and the refrigerant vapor will be present in the evaporator.

[0082] In the case of a single-component composition such as the compound of the above formula (3), it should be noted that the composition of the vapor refrigerant in the evaporator is the same as the composition of the liquid refrigerant in the evaporator. In this case, evaporation occurs at a constant temperature. However, when a refrigerant blend (or mixture) such as a combination of the compound of formula (3) and a co-compound is used, the liquid refrigerant and the refrigerant vapor in the evaporator (or condenser) can have different compositions.

[0083] Chillers with a cooling capacity exceeding 700 kW generally employ a flooded evaporator, and the refrigerant within the evaporator and condenser surrounds the coil or other conduits of the cooling medium (i.e., the refrigerant is on the shell side). The flooded evaporator requires more refrigerant but enables a closer approach temperature and higher efficiency. Chillers with a capacity of less than 700 kW generally employ an evaporator with refrigerant flowing inside the tubes and a cooling medium in the condenser surrounding the tubes, i.e., the cooling medium is on the shell side. Such chillers are called direct expansion (DX) chillers. A water-cooled direct expansion chiller is shown in FIG. 2. In a chiller as shown in FIG. 2, a first liquid cooling medium, which is a warm liquid such as warm water, enters the evaporator 6’ at the inlet 14. Most of the liquid refrigerant (along with a small amount of refrigerant vapor) enters the coil 9’ of the evaporator at the arrow 3’ and evaporates. As a result, the first liquid cooling medium is cooled in the evaporator, and the cooled first liquid cooling medium exits the evaporator at the outlet 16 and is sent to the object to be cooled such as a building. In this embodiment of FIG. 2, this is the cooled first liquid cooling medium that cools the building or other object to be cooled. The refrigerant vapor exits the evaporator at the arrow 4’ and is sent to the compressor 7’, where it is compressed and exits as a high-temperature and high-pressure refrigerant vapor. This refrigerant vapor enters the condenser 5’ through the coil 10’ of the condenser at 1’. The refrigerant vapor is cooled in the condenser by a second liquid cooling medium such as water and becomes liquid. The second liquid cooling medium enters the condenser through the cooling medium inlet 20 for the condenser. The second liquid cooling medium extracts heat from the refrigerant vapor that is being condensed, and that refrigerant vapor becomes liquid refrigerant, which warms the second liquid cooling medium in the condenser. The second liquid cooling medium exits the condenser through the condenser cooling medium outlet 18. The condensed refrigerant exits the condenser through the lower-temperature coil of FIG. 2, which is 10’, and flows through the expansion device 12. Examples of such an expansion device may include an orifice, a capillary tube, or an expansion valve. The expansion device 12 reduces the pressure of the liquid refrigerant. A small amount of vapor is produced as a result of the expansion and enters the evaporator with the liquid refrigerant through the coil 9’ to repeat the cycle.

[0084] In another embodiment, the cooling device may be a high-temperature heat pump device having at least two heating stages arranged as a cascade heating system, each stage circulating a working fluid through it, and including: (a) a first expansion device for reducing the pressure and temperature of a first working fluid liquid; (b) an evaporator in fluid communication with the first expansion device and having an inlet and an outlet; (c) a first compressor in fluid communication with the evaporator and having an inlet and an outlet; (d) a cascade heat exchange system in fluid communication with the first compressor and having (i) a first inlet and a first outlet, and (ii) a second inlet and a second outlet that are in thermal communication with the first inlet and the first outlet; (e) a second compressor in fluid communication with the second outlet of the cascade heat exchanger and having an inlet and an outlet; (f) a condenser in fluid communication with the second compressor and having an inlet and an outlet; and (g) a second expansion device in fluid communication with the condenser, wherein the second working fluid includes at least one alkyl perfluoroalkene ether. According to the present invention, a cascade heat pump system having at least two heating loops for circulating a working fluid through each loop is provided. One embodiment of such a cascade system is generally shown at 110 in FIG. 3. The cascade heat pump system 110 of the present invention includes at least two heating loops, namely a first or lower loop 112, which is a low-temperature loop, and a second or upper loop 114, which is a high-temperature loop 114, as shown in FIG. 3. Each loop circulates a working fluid through the loop.

[0085] The cascade heat pump system 110 includes a first expansion device 116. The first expansion device 116 has an inlet 116a and an outlet 116b. The first expansion device 116 reduces the pressure and temperature of the first working fluid liquid circulating through the first or low-temperature loop 112.

[0086] The cascade heat pump system 110 also includes an evaporator 118. The evaporator 118 has an inlet 118a and an outlet 118b. The first working fluid liquid from the first expansion device 116 enters the evaporator 118 through the evaporator inlet 118a, evaporates in the evaporator 118 to form first working fluid vapor. Then, the first working fluid vapor circulates to the evaporator outlet 118b.

[0087] The cascade heat pump system 110 also includes a first compressor 120. The first compressor 120 has an inlet 120a and an outlet 120b. The first working fluid vapor from the evaporator 118 circulates to the inlet 120a of the first compressor 120, is compressed, thereby increasing the pressure and temperature of the first working fluid vapor. Then, the compressed first working fluid vapor circulates to the outlet 120b of the first compressor 120.

[0088] The cascade heat pump system 110 also includes a cascade heat exchanger system 122. The cascade heat exchanger 122 has a first inlet 122a and a first outlet 122b. The first working fluid vapor from the first compressor 120 enters the first inlet 122a of the heat exchanger 122, condenses in the heat exchanger 122 to form a first working fluid liquid, thereby releasing heat. Then, the first working fluid liquid circulates to the first outlet 122b of the heat exchanger 122. The heat exchanger 122 also has a second inlet 122c and a second outlet 122d. The second working fluid liquid circulates from the second inlet 122c to the second outlet 122d of the heat exchanger 122, evaporates to form second working fluid vapor, thereby absorbing the heat released by the first working fluid (when it condenses). Then, the second working fluid vapor circulates to the second outlet 122d of the heat exchanger 122. Thus, in the embodiment of FIG. 3, the heat released by the first working fluid is directly absorbed by the second working fluid.

[0089] The cascade heat pump system 110 also includes a second compressor 124. The second compressor 124 has an inlet 124a and an outlet 124b. The second working fluid vapor from the cascade heat exchanger 122 is drawn into the compressor 124 through the inlet 124a and compressed, thereby increasing the pressure and temperature of the second working fluid vapor. The second working fluid vapor then circulates to the outlet 124b of the second compressor 124.

[0090] The cascade heat pump system 110 also includes a condenser 126 having an inlet 126a and an outlet 126b. The second working fluid from the second compressor 124 circulates from the inlet 126a and condenses in the condenser 126 to form a second working fluid liquid, thereby generating heat. The second working fluid liquid exits the condenser 126 through the outlet 126b.

[0091] The cascade heat pump system 110 also includes a second expansion device 128 having an inlet 128a and an outlet 128b. The second working fluid liquid passes through the second expansion device 128 that reduces the pressure and temperature of the second working fluid liquid exiting the condenser 126. This liquid may partially evaporate during this expansion. The second working fluid liquid with reduced pressure and temperature circulates from the expansion device 128 to the second inlet 122c of the cascade heat exchanger system 122.

[0092] As used herein, the terms "comprises," "comprising," "includes," "including," "has," "having," or any other variation thereof are intended to cover non-exclusive inclusion. For example, a composition, process, method, article, or apparatus that comprises elements listed is not necessarily limited to only those elements, but may include other elements not expressly listed or other elements associated with such composition, process, method, article, or apparatus. Further, unless expressly stated to the contrary, "or" refers to an inclusive "or" and not an exclusive "or." For example, the condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or absent), A is false (or absent) and B is true (or present), and both A and B are true (or present).

[0093] The transitional phrase "consisting of" excludes any element, step, or ingredient not specified. In the context of a claim, such a phrase closes the claim to the inclusion of materials other than those recited, except for impurities ordinarily associated with the recited materials. When the phrase "consisting of" appears in a clause within the body of a claim rather than immediately following the preamble, the phrase limits only the elements set forth in that clause and does not exclude other elements from the scope of the claim as a whole.

[0094] The transitional phrase "consisting essentially of" is used to define a composition, method that includes materials, steps, features, ingredients, or elements in addition to those literally disclosed, provided that the additional materials, steps, features, ingredients, or elements do not materially affect the basic and novel characteristics of the claimed invention, particularly the mode of operation for achieving any desired result of the process of the present invention. The term "consisting essentially of" has a meaning intermediate between "comprising" and "consisting of."

[0095] When the applicant defines the invention or a part thereof using non - limiting terms such as "comprising", it should be readily understood that (unless otherwise specified), such description should be construed to also include such an invention using the terms "consisting essentially of" or "consisting of".

[0096] Also, the use of "a" or "an" is for the purpose of describing the elements and components described in this specification. This is merely for convenience and is for giving the general meaning of the scope of the present invention. This description should be construed to include one or at least one, and the singular form also includes the plural form unless it is clear that it has a different meaning.

[0097] The following examples are provided to illustrate specific embodiments of the present invention and are not intended to limit the scope of the appended claims.

Example

[0098] An exemplary example of the formation of the compound of formula (3) is shown below.

[0099] (Example 1) Reaction of HFO - 1234ze with chlorotrifluoroethylene catalyzed by SbF5

[0100]

Chemical formula

[0101] 12 g (0.055 mol) of SbF5 was placed in a 400 mL Hastelloy® shaker tube, cooled with dry ice, evacuated, and filled with 150 g (1.32 mol) of HFO-1234ze and 150 g (1.29 mol) of chlorotrifluoroethylene (CTFE). This was placed in a barricade, warmed to ambient temperature, and stirred for 16 hours. The reaction vessel was cooled with ice, degassed, and the liquid product was added to 1 L of water. The organic layer was separated, dried over MgSO4, filtered, and 290 g of crude material was obtained. The crude material was fractionated to obtain 148 g (50% yield) of fraction with a boiling point. It was identified as a mixture of CF3CH=CHCF2CF2Cl and CF3CH=CHCFClCF3 in a ratio of 36:64 at 59 - 62 °C (the purity of this fraction was 97.8%). This fraction was redistilled to obtain 120 g of material with a purity of 99.3% and a boiling point of 60 - 61 °C. E-CF3CH=CHCF2CF2Cl: 19 F NMR (CDCl3): -66.38 (3F, m), -71.74 (2F, m), -113.98 (2F, m) ppm E-CF3CH=CHCFClCF3: 19 F NMR (CDCl3): -66.90 (3F, m), -82.15 (3F, m), -131.82 (1F, m) ppm 1 H NMR (CDCl3, mixed isomers): 6.48 (m) ppm GC / MS (m / z, mixture of isomers): 230 (M + , C5H2ClF7 + )

[0102] The ratio of CF3CH=CHCF2CF2Cl and CF3CH=CHCFClCF3 in the reaction product mixture can vary. The ratio of the reaction products can be in the range of about 30:70, about 32:68, about 34:66, and in some cases about 36:64.

[0103] (Example 2) Reaction of HFO-1234ze with chlorotrifluoroethylene catalyzed by AlCl3

[0104] [Chem.]

[0105] 12 g (0.09 mol) of anhydrous powdered AlCl3 was placed in a 400 mL Hastelloy® shaker tube, and the shaker tube was cooled, cooled with dry ice, evacuated, and filled with 75 g (0.66 mol) of HFO-1234ze and 75 g (0.64 mol) of chlorotrifluoroethylene (CTFE). The shaker tube was placed in a barricade, warmed to ambient temperature, and stirred for 16 hours. The reactor was cooled with ice, degassed, and the liquid product was added to 1 L of water. The organic layer was separated, dried over MgSO4, filtered, and 148 g of a crude material was obtained, which was found to contain 68% of a mixture of CF3CH=CHCF2CF2Cl and CF3CH=CHCFClCF3 (in a ratio of CF3CH=CHCF2CF2Cl and CF3CH=CHCFClCF3 of 54:46), along with higher boiling point materials. The calculated yield of the C5H2ClF7 fraction was 66%.

[0106] If desired, the amount of catalyst can be varied. The ratio of the reaction products of CF3CH=CHCF2CF2Cl and CF3CH=CHCFClCF3 can range from about 64:36, ~ about 62:38, and in some cases about 60:40.

[0107] Reaction of HFO-1234ze with SbF5 (comparative example). A 1 L Hastelloy (registered trademark) shaker tube stirred reactor was charged with 11 g (0.05 mol) of SbF5 cooled with dry ice, pressurized with nitrogen to leak, vented, evacuated, and 500 g (4.4 mol) of HFO-1234ze was condensed into the reactor. This was brought to ambient temperature and maintained at 25 - 30 °C for 12 hours. Water (100 mL) was injected into the reactor using a pump. The reactor was vented, opened, and the reaction mixture was added to a separatory funnel containing 1 L of water. The organic layer was separated, dried over MgSO4, filtered to obtain 474 g of a crude product, which was further flash distilled to obtain 400 g of a crude product. Fractionation was carried out using a 36-inch glass column with Hastelloy (registered trademark) packing, and 350 g (yield 70%) of the material was obtained at b.p. 86 - 87 °C. It was identified as E-CF3CH=CHCH(CF3)CF2H by NMR and GC / MS and contained 3% of the Z isomer. E-CF3CH=CHCH(CF3)CF2H: 19 F NMR (CDCl3): -65.86 (3F, m), -67.47 (3F, m), -120.00 (1F, ddm, 300, 54.1 Hz), -123.60 (1F, ddm, 300, 54.1 Hz) ppm 1 H (NMR (CDCl3, mixed isomers)): 6.06 (1H, m), 6.10 (1H, t, d, 54.1 or 2.5 Hz), 6.33 (1H, m) ppm GC / MS (m / z): 228 (M + 、C6H4F8 + )

[0108] (Example 3) Reaction of HFO-153-10ze using chlorotrifluoroethylene catalyzed by AlCl3

[0109]

Chemical formula

[0110] 1.0 g (0.007 mol) of anhydrous powdered AlCl3 was placed in a 50 mL flask in a dry box. The reactor was equipped with a thermocouple, a magnetic stir bar, and a dry ice condenser connected to a nitrogen line. The reactor was cooled with ice, and 11 g (0.042 mol) of HFO-153-10ze (C4F9CH=CHF) and 5 g (0.042 mol) of chlorotrifluoroethylene (CTFE) were introduced into the reaction mixture through the gas inlet tube over 30 minutes. The reaction vessel was slowly warmed to ambient temperature in a water bath and stirred for 4 hours. The crude reaction mixture was diluted with 300 mL of water, the organic layer was separated, dried over MgSO4, filtered to obtain 15 g of crude material, which was distilled using a 10-inch Vigreux column to give 7.9 g (75%) of material boiling at 120 - 129 °C, along with 3% of high-boiling material, containing a mixture of C4F9CH=CHCF2CF2Cl and C4F9CH=CHCFClCF3 (ratio 54:56). E-C4F9CH=CHCF2CF2Cl: 19 F NMR (CDCl3, J, Hz): -71.53 (2F, t, 4.7, Hz), -81.10 (3F t, 8.5, Hz), -113.68 (2F, m), -114.16 (2F, m) -124.35 (2F, m), -125.85 (2F, m) ppm 1 H NMR (CDCl3 J, Hz): 6.50 (m) E-C4F9CH=CHCFClCF3: 19 F NMR (CDCl3, J, Hz): -81.10 (3F t, 8.5, Hz), -81.84 (3F, d, 7.1, Hz), -113.68 (2F, m), -124.35 (2F, m), -125.85 (2F, m), -131.68 (1F, m) ppm 1 H NMR (CDCl3 J, Hz): 6.50 (m) MS (z / e, mixture of isomers): 361 [(M - F)+, C8H2ClF 12 + )

[0111] The ratio of the reaction products of C4F9CH=CHCF2CF2Cl and C4F9CH=CHCFClCF3 can be in the range of about 64:36, about 62:38, and in some cases about 60:40.

[0112] (Example 4) Reaction of HFO-1234ze with tetrafluoroethylene catalyzed by AlCl3

[0113] [Chemical formula]

[0114] 5 g (0.038 mol) of anhydrous powdered AlCl3 was placed in a 400 mL Hastelloy® shaker tube, and the shaker tube was cooled with dry ice, evacuated, and filled with 60 g (0.52 mol) of HFO-1234ze and 50 g (0.5 mol) of tetrafluoroethylene (TFE). The shaker tube was placed in a barricade and warmed to ambient temperature for 2 hours. Another 50 g (0.5 mol) of TFE was added and stirred for 12 hours. The reactor was cooled with ice, degassed, and the liquid product (140 g) was added to 1 L of water. The organic layer was separated, dried over MgSO4, and filtered to obtain 130 g of a crude material containing 65% of E-CF3CH=CHCF2CF3 (F12E) and 35% of E-C2F5CH=CHC3F7 (F23E). Fractionation using a 10-inch Vigreux column gave 46 g (yield 43%) identified as CF3CH=CHCF2CF3 (b.p. 29 - 30 °C) by GC / MS and NMR, and 28 g (yield 17%) of material with b.p. 70 - 74 °C (mainly 73 - 74 °C) identified as E-C2F5CH=CHC3F7 (purity 98%) by NMR and GC / MS. E-CF3CH=CHCF2CF3 19 19F NMR (CDCl3): -66.30 (3F, dm, 4.1 or 1.5 Hz), -85.07 (3F, m), -117.98 (2F, dm, 8.7 or 2.3 Hz) ppm GC / MS (m / z): 214 (M + , C5H2F8 + ) 1 1H NMR (CDCl3): 6.46 (m) ppm E-C2F5CH=CHC3F7: 19 19F NMR (CDCl3): -80.66 (3F, t, 9.1 Hz), -85.07 (3F, m), -115.28 (2F, quint, 8.7 Hz), -117.88 (2F, dm, 8.5 and 2.0 Hz), -127.88 (2F, s) ppm 1 1H NMR (CDCl3): 6.46 (m) ppm GC / MS (m / z): 314 (M + , C7H2F 12 + )

[0115] If desired, E-CF3CH=CHCF2CF3 (F12E) and E-C2F5CH=CHC3F7 (F23E) in the reaction product mixture can be varied by changing the amounts of the reactants. The amounts of E-CF3CH=CHCF2CF3 (F12E) and E-C2F5CH=CHC3F7 (F23E) in the reaction product can vary from 1 to 100 wt%, about 25 to 75 wt%, and in some cases about 50 to 50 wt%.

[0116] (Example 5) Reaction of HFO-1234ze with vinylidene fluoride catalyzed by AlCl3

[0117]

Chemical Structure

[0118] This reaction was carried out in a similar manner in a 400 mL Hastelloy® shaker tube by adding 5 g (0.038 mol) of anhydrous powdered AlCl3, 60 g (0.52 mol) of HFO-1234ze, and 32 g (0.5 mol) of vinylidene fluoride (VF2) to a one-port cold reaction vessel and using the same method. The reaction mixture was processed as described above. The crude product (89 g) was distilled to obtain 21 g (yield 24%) of a fraction having a boiling point of 63 - 68 °C, which was identified by GC / MS and NMR as a mixture of E-CF3CH=CHCH2CF3 and Z-CF3CH=CHCH2CF3 (ratio 92:8) along with 60 g of an uncharacterized high-boiling material. E-CF3CH=CHCH2CF3: 19 F NMR (CDCl3): -65.93 (3F, t, 9.2 Hz), -65.31 (3F, dm, 5.2 or 1.5 Hz) ppm 1 H NMR (CDCl3): 2.97 (2H, quint, 8.6 Hz), 5.91 (1H, m), 6.33 (1H, m) ppm Z-CF3CH=CHCH2CF3: 19 F NMR (CDCl3): -59.36 (3F, d, 7.9 Hz), -66.41 (3F, t, 9.2 Hz) ppm 1 H NMR (CDCl3): 3.16 (2H, quint, 8.6 Hz), 5.91 (m), 6.33 (1H, m) ppm GC / MS (m / z, mixed isomers): 178 (M + , C5H4F6 + )

[0119] The ratio of E-CF3CH=CHCH2CF3 and Z-CF3CH=CHCH2CF3 in the product mixture can range from about 1 - 100 wt%, about 25 - 75 wt%, and in some cases about 50 - 50 wt%. The ratio can be varied by changing at least one of the ratio of reactants, any solvent, and temperature.

[0120] Reaction of HFO-1234yf and tetrafluoroethylene Catalyst with AlCl3 (Comparative Example) The reaction of 5 g (0.038 mol) of anhydrous powdered AlCl3, 115 g (1 mol) of HFO-1234yf (CF3CF=CH2, an isomer of HFO-1234ze), and 50 g of TFE was carried out at ambient temperature as described above in a 400 mL Hastelloy (registered trademark) shaker tube. No pressure drop was observed over a 16-hour period, and no liquid product was recovered after the shaker tube was evacuated.

[0121] (Example 6) Cycle model of organic Rankine cycle Figure 4 is a schematic diagram of an organic Rankine cycle (ORC) model. The ORC efficiency of a specific composition of the present invention was determined by using the mass and energy balances that specify the system and unit operations shown in Figure 4. Using typical conditions of an ORC system for generating electricity from a low-temperature heat source, the theoretical performance was calculated. Thus, the average condenser and boiler temperatures are 40 °C and 100 °C, respectively, and 5 K for both superheat and subcooling. The entropy efficiencies for pump compression and turbine expansion are 85% and 50%, respectively. The power generation efficiency is the ratio of the thermal input energy utilized as the net shaft work, which is 100%x(W - W ポンプ ) / Q h where. The volumetric power capacity is the next shaft work multiplied by the density of the fluid exiting the turbine, i.e., (W - W ポンプ )×ρ3. W is the work output from the turbine, W ポンプ is the work input to the pump, Q h is the heat source input, and ρ3 is the density of the fluid exiting the turbine.

[0122] The efficiency and capacity of the binary fluid blend over the entire composition range were determined. Figures 5 and 6 show the dependence of efficiency and capacity on the fluid composition for the product component, formula (3), E-F23E with the co-compound R-1336mzzZ. From Figure 5, it can be seen that the theoretical efficiency can have up to 37 wt% of E-F23E. This maximum efficiency at 37 wt% of E-F23E was compared with R-1233zdE or R-1225yeE or R-1225yeZ and R245fa. As shown in Table 1, E-F23E / R-1336mzzZ is in the range of about 30 to about 40 F23E, and 70 to 60 wt% of R-1336mzzZ is efficient. In particular, the 37 / 63 wt% blend results in the maximum efficiency.

[0123]

Table 1

[0124] (Example 7) HTHP cycle model The heating coefficient (COP h ) and the volumetric heating capacity (CAP h ) of the specific compositions of the present invention were determined by using the mass and energy balances that specify the system and unit operations shown in Figure 2. The average evaporator and condenser temperatures are 70 °C and 100 °C, respectively, for a 30-degree temperature rise. There is superheat and subcooling of 5 to 10 Kelvin, respectively. The entropy efficiency for compression is 70%. COP h is the ratio of the high-temperature heat output per kg of the working fluid circulating through the condenser to the power input to the compressor per kg of the working fluid circulating through the compressor (W), i.e., Q h / W. CAP h is the product of the heating effect and the density of the fluid entering the compressor (ρ1), i.e., Q h ×ρ1. Using these conditions, the COP h and CAP h of the binary fluid blend of the specific present invention were calculated over a range of compositions. Figures 7 and 8 show the COP hshows the dependencies, and are, respectively, 1) E-F23E with E-F12E, and 2) E-F23E containing the co-compound R-1336mzzZ. COP h It can be seen from FIGS. 7 and 8 that h has a maximum value for both binary systems with about 51 wt % of E-F23E.

[0125] The two-component composition has a maximum COP at 51 wt % of E-F23E h value. This maximum efficiency for both blends of the invention with about 51 wt % of E-F23E was compared with the net fluid E-F23E, E-F12E, R-1336mzzZ or R-1233zdE and R245fa. As shown in Table 2, both blends of the invention, E-F23E / E-F12E and E-F23E / R-1336mzzZ, both have a maximum COP h value at about 51 wt-% E-F23E, and E-F23E / E-F12E has a maximum COP h value at 51 wt-% E-F23E.

[0126]

Table 2

[0127] Although the invention has been described with reference to one or more embodiments, it will be understood by those skilled in the art that various changes can be made without departing from the scope of the invention and equivalents can be used in place of its elements. Additionally, many modifications can be made without departing from the essential scope of the invention to adapt a particular situation or material to the teachings of the invention. Accordingly, the invention is not limited to the specific embodiments disclosed as the best mode contemplated for carrying out the invention, but the invention is intended to include all embodiments included within the scope of the appended claims. Additionally, all numerical values specified in the detailed description are to be construed as if both the exact and approximate values were explicitly specified.

Claims

Claim 1 A process for transferring heat, comprising: providing an article; and contacting the article with a heat transfer medium, wherein the heat transfer medium comprises a composition containing a compound of formula (4). R f CF 3 (CX 5 X 6 CX 7 X 8 ) n CH=CHCX 9 X 10 CX 11 X 12 F(4) In the formula, R f is a C 1 -C 10 perfluorinated alkyl group, wherein X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 and X 12 are each independently H, Cl, or F, and n is an integer of 0 or 1, X 5 、 X 6 、 X 7 、 X 8 、 X 9 、 X 10 、 X 11 and X 12 The total number of F represented by is at least 2, and 1,1,1,4,4,5,5,5 - Octafluoropent - 2 - ene (F12E, CF 3 CH=CHC 2 F 5 ), (E) - 1,1,1,4,4,4 - Hexafluoro - 2 - butene, (HFO - 1336mzz(E), CF 3 CH=CHCF 3 ), (Z) - 1,1,1,4,4,4 - Hexafluoro - 2 - butene, (HFO - 1336mzz(Z), CF 3 CH=CHCF 3 ), (E) - 2,3 - Bis(trifluoromethyl)oxirane, (HFO - 1336mzz(E)(epoxide), CFCH( - O - )CHCF 3 ), (Z) - 2,3 - Bis(trifluoromethyl)oxirane, (HFO - 1336mzz(Z)(epoxide), CFCH( - O - )CHCF 3 ), HFO - 1234ze(Z), HFO - 1234ye(E), HFO - 1234ye(Z), HFO - 1438mzz(E), HFO - 1438mzz(Z), Heptafluoro - 4 - (trifluoromethyl) - pent - 2 - ene, ((HFO - 153 - 10mzzy), (mixture of HFO - 153 - 10 isomers)), HFO - 162 - 13mcyz, HFO - 162 - 13mczy, (E) - 1,3,4,4,4 - Pentafluoro - 3 - (trifluoromethyl) - 1 - butene, (HFO - 1438ezy(E), CFH=CHCF(CF 3 )) 2 ), (Z) - 1,3,4,4,4 - Pentafluoro - 3 - (trifluoromethyl) - 1 - butene, (HFO - 1438ezy(Z), CFH=CHCF(CF 3 )) 2 ), HFO - 1336ze(E), HFO - 1336ze(Z), HFC - 245fa, HFC - 245ea, HFC - 365mfc, HFC - 43 - 10mee, (E) - 1 - Chloro - 3,3,3 - trifluoro - propene, (HCFO - 1233zd(E), CHCl=CHCF 3 ), (Z) - 1 - Chloro - 3,3,3 - trifluoro - propene, (HCFO - 1233zd(Z), CHCl=CHCF 3 ), HCFO-1224yd(E), HCFO-1224yd(Z), iso-pentane, n-pentane, cyclopentane, n-hexane, cyclohexane, heptane, methyl formate, dimethoxymethane, dimethoxyethane, propanal, methanol, ethanol, isopropanol, N-propanol, trans-1,2-dichloro-ethylene, cis-1,2-dichloro-ethylene, 1-methoxyheptafluoropropane (HFE-7000, CH 3 OCF 2 CF 2 CF 3 ), methyl nonafluorobutyl ether (HFE-71DA, C 4 F 9 OCH 3 ), methoxy-nonafluorobutane (HFE-7100, C 4 F 9 OCH 3 , CH 3 O-3(CF 2 )-CH 3 ), ethoxy-nonafluorobutane (HFE-7200, CH 3 CH 2 OCF 2 CF 2 CF 2 CF 3 , C 4 F 9 OC 2 H 5 ), dodecafluoro-2-methylpentan-3-one (NOVEC-649 or Novec-1230, CF 3 CF 2 C(O)CF(CF 3 ) 2 ), 1,1,1,2,2,3,4,5,5,5-decafluoro-3-methoxy-4-(trifluoromethyl)-pentane (Novec-7300; C 7 H 3 F 13 O; n-C 2 F 5 CF(OCH 3 )CF(CF 3 ) 2 ), siloxane, methyl perfluoroheptene ether, methoxy-perfluoro-heptene ether or MPHE (HFX-110; C 7 F 13 (OCH 3 )), MPPe(HFX-75), perfluorohepta-2-ene / perfluorohepta-3-ene (HFO-161-14myy / HFO-161-14mcyy, PFH, mixture, CF 3 CF=CFCF 2 CF 2 CF 2 CF 3 / CF 3 CF 2 CF=CFCF 2 CF 2 CF 3 )), perfluorohepta-1-ene (FC-141-10cy, CF 2 =CFCF 2 CF 2 CF 2 CF 2 CF 3 ), 1-bromo-1,2,3,3,3-pentafluoropropene, (R-1215ybB, CF 3 CF=CFBr), 2-bromo-1,1,1,3,3-pentafluoro-2-propene, (R-1215xbB1, CF 3 CBr=CF 2 ), (E)-1-bromo-2,3,3,3-tetrafluoropropene, (HBFO-1224ydB(E), CF 3 CF=CHBr), (Z)-1-bromo-2,3,3,3-tetrafluoropropene, (HBFO-1224ydB(Z), CF 3 CF=CHBr), 2-bromo-3,3,3-trifluoro-propene, (BFO-1233xfB, CF 3 CBr=CH 2 ), trans-DCE / R-1336mzz(Z) mixture, (suitable mixtures include those disclosed in International Publication No. 2008 / 134061), (trans-DCE / methyl perfluoroheptene ether, (suitable mixtures include those disclosed in US Patent Publication No. 2012 / 0227764(Al)), (trans-DCE / HFC-43-10mee mixture, (CHCl=CHCl / CF 3 CHFCHFCF 2 CF 3 ), (Examples of suitable mixtures include those disclosed as in U.S. Patent No. 5,196,137), 2-bromo-2-chloro-1,1,1-trifluoroethane, (R-123B1, CHBrClCF 3 ), 2,3-dichloro-3,3-difluoropropene, (R-1232xf, CClF 2 CCl=CH 2 ), (E)-1,1,4,4-tetrafluoro-2-butene, (R-1345mzz(E), CHF 2 CH=CHCHF 2 ), 2-bromo-1,1-difluoroethane, (BDFE, CHF 2 CH 2 Br), 1-chloro-2,3,3,4,4,4-hexafluoro-1-butene, (HCFO-1326yd-Z, CF 3 CF 2 CF=CHCl), 1-chloro-2,3,3-trifluoropropene, (HCFO-1233yd-Z, CHF 2 CF=CHCl), 2-(1,1,2,2-tetrafluoroethoxy)-1-fluoroethylene, (HFO-1345ezcEβγ, CFH=CHOCF 2 CF 2 H), 2,3,3,3-tetrafluoro-1-(1,1,2,2-tetrafluoroethoxy)prop-1-ene, (HFO-1438mzycEγδ, CF 3 CF=CHOCF 2 CF 2 H), 1-(difluoromethoxy)-2,3,3,3-tetrafluoroprop-1-ene, (HFO-1336pzEαβ, CF 3 CF=CHOCF 2 H), 2,3,3-trifluoro-1-(trifluoromethoxy)prop-1-ene, (HFO-1336mzyEαβ, CHF 2 CF=CHOCF 3 ), 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene, (F22E, C 2 F 5 CH=CHC 2 F 5 ), 1,1,1,2,2,3,3,4,4,7,7,8,8,9,9,10,10,10 - octadecafluoro - 5 - decene, (F44E,C 4 F 9 CH=CHC 4 F 9 ), or 1,1,1,2,3,4,4,5,5,5 - decafluoropentane, (HFC - 43 - 10mee,CF 3 CHFCHFCF 2 CF 3 ), a process comprising a co - compound containing at least one of these. Claim 2 The compound of the formula (4) is 1,1,1,2,2,5,5,6,6,7,7,7-dodecafluorohept-2-ene (F23E, C 3 F 7 CH=CHC 2 F 5 ), The process according to claim 1. Claim 3 The co-compound is 1,1,1,4,4,5,5,5 - octafluoropent - 2 - ene (F12E, CF 3 CH=CHC 2 F 5 ), the process according to claim 2. Claim 4 The composition contains 40 to 60% by weight of 1,1,1,2,2,5,5,6,6,7,7,7-dodecafluorohept-2-ene (F23E, C 3 F 7 CH=CHC 2 F 5 ), and 40 to 60% by weight of 1,1,1,4,4,5,5,5-octafluoropent-2-ene (F12E, CF 3 CH=CHC 2 F 5 ), and the process according to claim 3. Claim 5 A process for treating a surface, comprising: providing a surface; and contacting the surface with a treatment composition, wherein the surface comprises a material capable of being treated deposited thereon, and wherein the treatment composition comprises a composition containing a compound of formula (4). R f CF 3 (CX 5 X 6 CX 7 X 8 ) n CH=CHCX 9 X 10 CX 11 X 12 F(4) In the formula, R f is a C 1 -C 10 perfluorinated alkyl group, wherein, X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 and X 12 are each independently H, Cl, or F, and n is an integer of 0 or 1, X 5 、 X 6 、 X 7 、 X 8 、 X 9 、 X 10 、 X 11 and X 12 The total number of F represented by is at least 2, and 1,1,1,4,4,5,5,5 - Octafluoropent - 2 - ene (F12E, CF 3 CH=CHC 2 F 5 ), (E) - 1,1,1,4,4,4 - Hexafluoro - 2 - butene, (HFO - 1336mzz(E), CF 3 CH=CHCF 3 ), (Z) - 1,1,1,4,4,4 - Hexafluoro - 2 - butene, (HFO - 1336mzz(Z), CF 3 CH=CHCF 3 ), (E) - 2,3 - Bis(trifluoromethyl)oxirane, (HFO - 1336mzz(E)(epoxide), CFCH( - O - )CHCF 3 ), (Z) - 2,3 - Bis(trifluoromethyl)oxirane, (HFO - 1336mzz(Z)(epoxide), CFCH( - O - )CHCF 3 ), HFO - 1234ze(Z), HFO - 1234ye(E), HFO - 1234ye(Z), HFO - 1438mzz(E), HFO - 1438mzz(Z), Heptafluoro - 4 - (trifluoromethyl) - pent - 2 - ene, ((HFO - 153 - 10mzzy), (mixture of HFO - 153 - 10 isomers)), HFO - 162 - 13mcyz, HFO - 162 - 13mczy, (E) - 1,3,4,4,4 - Pentafluoro - 3 - (trifluoromethyl) - 1 - butene, (HFO - 1438ezy(E), CFH=CHCF(CF 3 )) 2 ), (Z) - 1,3,4,4,4 - Pentafluoro - 3 - (trifluoromethyl) - 1 - butene, (HFO - 1438ezy(Z), CFH=CHCF(CF 3 )) 2 ), HFO - 1336ze(E), HFO - 1336ze(Z), HFC - 245fa, HFC - 245ea, HFC - 365mfc, HFC - 43 - 10mee, (E) - 1 - Chloro - 3,3,3 - trifluoro - propene, (HCFO - 1233zd(E), CHCl=CHCF 3 ), (Z) - 1 - Chloro - 3,3,3 - trifluoro - propene, (HCFO - 1233zd(Z), CHCl=CHCF 3 ), HCFO-1224yd(E), HCFO-1224yd(Z), iso-pentane, n-pentane, cyclopentane, n-hexane, cyclohexane, heptane, methyl formate, dimethoxymethane, dimethoxyethane, propanal, methanol, ethanol, isopropanol, N-propanol, trans-1,2-dichloro-ethylene, cis-1,2-dichloro-ethylene, 1-methoxyheptafluoropropane (HFE-7000, CH 3 OCF 2 CF 2 CF 3 ), methyl nonafluorobutyl ether (HFE-71DA, C 4 F 9 OCH 3 ), methoxy-nonafluorobutane (HFE-7100, C 4 F 9 OCH 3 , CH 3 O-3(CF 2 )-CH 3 ), ethoxy-nonafluorobutane (HFE-7200, CH 3 CH 2 OCF 2 CF 2 CF 2 CF 3 , C 4 F 9 OC 2 H 5 ), dodecafluoro-2-methylpentan-3-one (Novec-649 or Novec-1230, CF 3 CF 2 C(O)CF(CF 3 ) 2 ), 1,1,1,2,2,3,4,5,5,5-decafluoro-3-methoxy-4-(trifluoromethyl)-pentane (Novec-7300; C 7 H 3 F 13 O; n-C 2 F 5 CF(OCH 3 )CF(CF 3 ) 2 ), siloxane, methyl perfluoroheptene ether, methoxy-perfluoro-heptene ether or MPHE (HFX-110; C 7 F 13 (OCH 3 )、MPPE(HFX - 75)、perfluorohepta - 2 - ene / perfluorohepta - 3 - ene (HFO - 161 - 14myy / HFO - 161 - 14mcyy, PFH, mixture, CF 3 CF = CFCF 2 CF 2 CF 2 CF 3 / CF 3 CF 2 CF = CFCF 2 CF 2 CF 3 )、perfluorohepta - 1 - ene (FC - 141 - 10cy, CF 2 = CFCF 2 CF 2 CF 2 CF 2 CF 3 )、1 - bromo - 1,2,3,3,3 - pentafluoropropene, (R - 1215ybB, CF 3 CF = CFBr)、2 - bromo - 1,1,1,3,3 - pentafluoro - 2 - propene, (R - 1215xbB1, CF 3 CBr = CF 2 )、(E) - 1 - bromo - 2,3,3,3 - tetrafluoropropene, (HBFO - 1224ydB(E), CF 3 CF = CHBr)、(Z) - 1 - bromo - 2,3,3,3 - tetrafluoropropene, (HBFO - 1224ydB(Z), CF 3 CF = CHBr)、2 - bromo - 3,3,3 - trifluoro - propene, (BFO - 1233xfB, CF 3 CBr = CH 2 )、trans - DCE / R - 1336mzz(Z) mixture, (Suitable mixtures include those disclosed in International Publication No. 2008 / 134061)、(trans - DCE / methyl perfluoroheptene ether, (Suitable mixtures include those disclosed in US Patent Publication No. 2012 / 0227764(A1))、(trans - DCE / HFC - 43 - 10mee mixture, (CHCl = CHCl / CF 3 CHFCHFCF 2 CF 3 ), (Examples of suitable mixtures include those disclosed as in U.S. Patent No. 5,196,137), 2-bromo-2-chloro-1,1,1-trifluoroethane, (R-123B1, CHBrClCF 3 ), 2,3-dichloro-3,3-difluoropropene, (R-1232xf, CClF 2 CCl=CH 2 ), (E)-1,1,4,4-tetrafluoro-2-butene, (R-1345mzz(E), CHF 2 CH=CHCHF 2 ), 2-bromo-1,1-difluoroethane, (BDFE, CHF 2 CH 2 Br), 1-chloro-2,3,3,4,4,4-hexafluoro-1-butene, (HCFO-1326yd-Z, CF 3 CF 2 CF=CHCl), 1-chloro-2,3,3-trifluoropropene, (HCFO-1233yd-Z, CHF 2 CF=CHCl), 2-(1,1,2,2-tetrafluoroethoxy)-1-fluoroethylene, (HFO-1345ezcEβγ, CFH=CHOCF 2 CF 2 H), 2,3,3,3-tetrafluoro-1-(1,1,2,2-tetrafluoroethoxy)prop-1-ene, (HFO-1438mzycEγδ, CF 3 CF=CHOCF 2 CF 2 H), 1-(difluoromethoxy)-2,3,3,3-tetrafluoroprop-1-ene, (HFO-1336pzEαβ, CF 3 CF=CHOCF 2 H), 2,3,3-trifluoro-1-(trifluoromethoxy)prop-1-ene, (HFO-1336mzyEαβ, CHF 2 CF=CHOCF 3 ), 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene, (F22E, C 2 F 5 CH=CHC 2 F 5 ), 1, 1, 1, 2, 2, 3, 3, 4, 4, 7, 7, 8, 8, 9, 9, 10, 10, 10 - octadecafluoro - 5 - decene, (F44E, C 4 F 9 CH=CHC 4 F 9 ), or 1, 1, 1, 2, 3, 4, 4, 5, 5, 5 - decafluoropentane, (HFC - 43 - 10mee, CF 3 CHFCHFCF 2 CF 3 ), a process comprising a co - compound containing at least one of them. Claim 6 The compound of the formula (4) is 1,1,1,2,2,5,5,6,6,7,7,7-dodecafluorohept-2-ene (F23E, C 3 F 7 CH=CHC 2 F 5 ), The process according to claim 5. Claim 7 The co-compound is 1,1,1,4,4,5,5,5-octafluoropent-2-ene (F12E, CF 3 CH=CHC 2 F 5 ), the process according to claim 6. Claim 8 The composition comprises 40 to 60% by weight of 1,1,1,2,2,5,5,6,6,7,7,7-dodecafluorohept-2-ene (F23E, C 3 F 7 CH=CHC 2 F 5 ) and 40 to 60% by weight of 1,1,1,4,4,5,5,5-octafluoropent-2-ene (F12E, CF 3 CH=CHC 2 F 5 ) and the process according to claim 7. Claim 9 A cooling, heating, or power generation system, comprising: an evaporator; a condenser; a compressor; an expansion device; and a heat transfer medium, wherein the heat transfer medium comprises a composition containing a compound of formula (4). R f CF 3 (CX 5 X 6 CX 7 X 8 ) n CH=CHCX 9 X 10 CX 11 X 12 F(4) In the formula, R f is a C 1 -C 10 perfluorinated alkyl group, and wherein, X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 and X 12 are each independently H, Cl, or F, and n is an integer of 0 or 1, X 5 、 X 6 、 X 7 、 X 8 、 X 9 、 X 10 、 X 11 and X 12 The total number of F represented by is at least 2, and 1,1,1,4,4,5,5,5 - Octafluoropent - 2 - ene (F12E, CF 3 CH=CHC 2 F 5 ), (E) - 1,1,1,4,4,4 - Hexafluoro - 2 - butene, (HFO - 1336mzz(E), CF 3 CH=CHCF 3 ), (Z) - 1,1,1,4,4,4 - Hexafluoro - 2 - butene, (HFO - 1336mzz(Z), CF 3 CH=CHCF 3 ), (E) - 2,3 - Bis(trifluoromethyl)oxirane, (HFO - 1336mzz(E)(epoxide), CFCH( - O - )CHCF 3 ), (Z) - 2,3 - Bis(trifluoromethyl)oxirane, (HFO - 1336mzz(Z)(epoxide), CFCH( - O - )CHCF 3 ), HFO - 1234ze(Z), HFO - 1234ye(E), HFO - 1234ye(Z), HFO - 1438mzz(E), HFO - 1438mzz(Z), Heptafluoro - 4 - (trifluoromethyl) - pent - 2 - ene, ((HFO - 153 - 10mzzy), (mixture of HFO - 153 - 10 isomers)), HFO - 162 - 13mcyz, HFO - 162 - 13mczy, (E) - 1,3,4,4,4 - Pentafluoro - 3 - (trifluoromethyl) - 1 - butene, (HFO - 1438ezy(E), CFH=CHCF(CF 3 )) 2 ), (Z) - 1,3,4,4,4 - Pentafluoro - 3 - (trifluoromethyl) - 1 - butene, (HFO - 1438ezy(Z), CFH=CHCF(CF 3 )) 2 ), HFO - 1336ze(E), HFO - 1336ze(Z), HFC - 245fa, HFC - 245ea, HFC - 365mfc, HFC - 43 - 10mee, (E) - 1 - Chloro - 3,3,3 - trifluoro - propene, (HCFO - 1233zd(E), CHCl=CHCF 3 ), (Z) - 1 - Chloro - 3,3,3 - trifluoro - propene, (HCFO - 1233zd(Z), CHCl=CHCF 3 ), HCFO-1224yd(E), HCFO-1224yd(Z), iso-pentane, n-pentane, cyclopentane, n-hexane, cyclohexane, heptane, methyl formate, dimethoxymethane, dimethoxyethane, propanal, methanol, ethanol, isopropanol, N-propanol, trans-1,2-dichloro-ethylene, cis-1,2-dichloro-ethylene, 1-methoxyheptafluoropropane (HFE-7000, CH 3 OCF 2 CF 2 CF 3 ), methyl nonafluorobutyl ether (HFE-71DA, C 4 F 9 OCH 3 ), methoxy-nonafluorobutane (HFE-7100, C 4 F 9 OCH 3 , CH 3 O-3(CF 2 )-CH 3 ), ethoxy-nonafluorobutane (HFE-7200, CH 3 CH 2 OCF 2 CF 2 CF 2 CF 3 , C 4 F 9 OC 2 H 5 ), dodecafluoro-2-methylpentan-3-one (NOVEC-649 or Novec-1230, CF 3 CF 2 C(O)CF(CF 3 ) 2 ), 1,1,1,2,2,3,4,5,5,5-decafluoro-3-methoxy-4-(trifluoromethyl)-pentane (Novec-7300; C 7 H 3 F 13 On-C 2 F 5 CF(OCH 3 )CF(CF 3 ) 2 ), siloxane, methyl perfluoroheptene ether, methoxy-perfluoro-heptene ether or MPHE (HFX-110; C 7 F 13 (OCH 3 )), MPPe(HFX-75), perfluorohepta-2-ene / perfluorohepta-3-ene(HFO-161-14myy / HFO-161-14mcyy, PFH, mixture, CF 3 CF=CFCF 2 CF 2 CF 2 CF 3 / CF 3 CF 2 CF=CFCF 2 CF 2 CF 3 )), perfluorohepta-1-ene(FC-141-10cy, CF 2 =CFCF 2 CF 2 CF 2 CF 2 CF 3 ), 1-bromo-1,2,3,3,3-pentafluoropropene, (R-1215ybB, CF 3 CF=CFBr), 2-bromo-1,1,1,3,3-pentafluoro-2-propene, (R-1215xbB1, CF 3 CBr=CF 2 ), (E)-1-bromo-2,3,3,3-tetrafluoropropene, (HBFO-1224ydB(E), CF 3 CF=CHBr), (Z)-1-bromo-2,3,3,3-tetrafluoropropene, (HBFO-1224ydB(Z), CF 3 CF=CHBr), 2-bromo-3,3,3-trifluoro-propene, (BFO-1233xfB, CF 3 CBr=CH 2 ), trans-DCE / R-1336mzz(Z) mixture, (suitable mixtures include those disclosed in International Publication No. 2008 / 134061), (trans-DCE / methyl perfluoroheptene ether, (suitable mixtures include those disclosed in US Patent Publication No. 2012 / 0227764(Al)), (trans-DCE / HFC-43-10mee mixture, (CHCl=CHCl / CF 3 CHFCHFCF 2 CF 3 ), (Suitable mixtures include those disclosed as in U.S. Patent No. 5,196,137), 2-bromo-2-chloro-1,1,1-trifluoroethane, (R-123B1, CHBrClCF 3 ), 2,3-dichloro-3,3-difluoropropene, (R-1232xf, CClF 2 CCl=CH 2 ), (E)-1,1,4,4-tetrafluoro-2-butene, (R-1345mzz(E), CHF 2 CH=CHCHF 2 ), 2-bromo-1,1-difluoroethane, (BDFE, CHF 2 CH 2 Br), 1-chloro-2,3,3,4,4,4-hexafluoro-1-butene, (HCFO-1326yd-Z, CF 3 CF 2 CF=CHCl), 1-chloro-2,3,3-trifluoropropene, (HCFO-1233yd-Z, CHF 2 CF=CHCl), 2-(1,1,2,2-tetrafluoroethoxy)-1-fluoroethylene, (HFO-1345ezcEβγ, CFH=CHOCF 2 CF 2 H), 2,3,3,3-tetrafluoro-1-(1,1,2,2-tetrafluoroethoxy)prop-1-ene, (HFO-1438mzycEγδ, CF 3 CF=CHOCF 2 CF 2 H), 1-(difluoromethoxy)-2,3,3,3-tetrafluoroprop-1-ene, (HFO-1336pzEαβ, CF 3 CF=CHOCF 2 H), 2,3,3-trifluoro-1-(trifluoromethoxy)prop-1-ene, (HFO-1336mzyEαβ, CHF 2 CF=CHOCF 3 ), 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene, (F22E, C 2 F 5 CH=CHC 2 F 5 ), 1,1,1,2,2,3,3,4,4,7,7,8,8,9,9,10,10,10 - octadecafluoro - 5 - decene, (F44E,C 4 F 9 CH = CHC 4 F 9 ), or 1,1,1,2,3,4,4,5,5,5 - decafluoropentane, (HFC - 43 - 10mee,CF 3 CHFCHFCF 2 CF 3 ) and a system comprising a co - compound containing at least one of them. Claim 10 The compound of formula (4) is 1,1,1,2,2,5,5,6,6,7,7,7-dodecafluorohept-2-ene (F23E, C 3 F 7 CH=CHC 2 F 5 ), The system according to claim 9. Claim 11 wherein the co-compound is 1,1,1,4,4,5,5,5 - octafluoropent - 2 - ene (F12E, CF 3 CH=CHC 2 F 5 ), the system according to claim 10. Claim 12 The composition comprises 40 to 60% by weight of 1,1,1,2,2,5,5,6,6,7,7,7-dodecafluorohept-2-ene (F23E, C 3 F 7 CH=CHC 2 F 5 ) and 40 to 60% by weight of 1,1,1,4,4,5,5,5-octafluoropent-2-ene (F12E, CF 3 CH=CHC 2 F 5 ) and the system according to claim 11. Claim 13 The system according to claim 9, wherein the condenser operates at a temperature higher than 100°C. Claim 14 A heat pipe system, comprising: a heat pipe having a working fluid therein; wherein the working fluid comprises a composition containing a compound of formula (4). R f CF 3 (CX 5 X 6 CX 7 X 8 ) n CH=CHCX 9 X 10 CX 11 X 12 F(4) In the formula, R f is a C 1 -C 10 perfluorinated alkyl group, and wherein X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , and X 12 are each independently H, Cl, or F, and n is an integer of 0 or 1, X 5 、X 6 、X 7 、X 8 、X 9 、X 10 、X 11 and X 12 The total number of F represented by is at least 2, and 1,1,1,4,4,5,5,5 - Octafluoropent - 2 - ene (F12E, CF 3 CH=CHC 2 F 5 ), (E) - 1,1,1,4,4,4 - Hexafluoro - 2 - butene, (HFO - 1336mzz(E), CF 3 CH=CHCF 3 ), (Z) - 1,1,1,4,4,4 - Hexafluoro - 2 - butene, (HFO - 1336mzz(Z), CF 3 CH=CHCF 3 ), (E) - 2,3 - Bis(trifluoromethyl)oxirane, (HFO - 1336mzz(E)(epoxide), CFCH( - O - )CHCF 3 ), (Z) - 2,3 - Bis(trifluoromethyl)oxirane, (HFO - 1336mzz(Z)(epoxide), CFCH( - O - )CHCF 3 ), HFO - 1234ze(Z), HFO - 1234ye(E), HFO - 1234ye(Z), HFO - 1438mzz(E), HFO - 1438mzz(Z), Heptafluoro - 4 - (trifluoromethyl) - pent - 2 - ene, ((HFO - 153 - 10mzzy), (mixture of HFO - 153 - 10 isomers)), HFO - 162 - 13mcyz, HFO - 162 - 13mczy, (E) - 1,3,4,4,4 - Pentafluoro - 3 - (trifluoromethyl) - 1 - butene, (HFO - 1438ezy(E), CFH=CHCF(CF 3 )) 2 ), (Z) - 1,3,4,4,4 - Pentafluoro - 3 - (trifluoromethyl) - 1 - butene, (HFO - 1438ezy(Z), CFH=CHCF(CF 3 )) 2 ), HFO - 1336ze(E), HFO - 1336ze(Z), HFC - 245fa, HFC - 245ea, HFC - 365mfc, HFC - 43 - 10mee, (E) - 1 - Chloro - 3,3,3 - trifluoro - propene, (HCFO - 1233zd(E), CHCl=CHCF 3 ), (Z) - 1 - Chloro - 3,3,3 - trifluoro - propene, (HCFO - 1233zd(Z), CHCl=CHCF 3 ), HCFO-1224yd(E), HCFO-1224yd(Z), iso-pentane, n-pentane, cyclopentane, n-hexane, cyclohexane, heptane, methyl formate, dimethoxymethane, dimethoxyethane, propanal, methanol, ethanol, isopropanol, N-propanol, trans-1,2-dichloro-ethylene, cis-1,2-dichloro-ethylene, 1-methoxyheptafluoropropane (HFE-7000, CH 3 OCF 2 CF 2 CF 3 ), methyl nonafluorobutyl ether (HFE-71DA, C 4 F 9 OCH 3 ), methoxy-nonafluorobutane (HFE-7100, C 4 F 9 OCH 3 , CH 3 O-3(CF 2 )-CH 3 ), ethoxy-nonafluorobutane (HFE-7200, CH 3 CH 2 OCF 2 CF 2 CF 2 CF 3 , C 4 F 9 OC 2 H 5 ), dodecafluoro-2-methylpentan-3-one (Novec-649 or Novec-1230, CF 3 CF 2 C(O)CF(CF 3 ) 2 ), 1,1,1,2,2,3,4,5,5,5-decafluoro-3-methoxy-4-(trifluoromethyl)-pentane (Novec-7300; C 7 H 3 F 13 O; n-C 2 F 5 CF(OCH 3 )CF(CF 3 ) 2 ), siloxane, methyl perfluoroheptene ether, methoxy-perfluoro-heptene ether or MPHE (HFX-110; C 7 F 13 (OCH 3 )、MPPE (HFX-75)、perfluorohepta-2-ene / perfluorohepta-3-ene (HFO-161-14myy / HFO-161-14mcyy, PFH, mixture, CF 3 CF=CFCF 2 CF 2 CF 2 CF 3 / CF 3 CF 2 CF=CFCF 2 CF 2 CF 3 )、perfluorohepta-1-ene (FC-141-10cy, CF 2 =CFCF 2 CF 2 CF 2 CF 2 CF 3 )、1-bromo-1,2,3,3,3-pentafluoropropene, (R-1215ybB, CF 3 CF=CFBr)、2-bromo-1,1,1,3,3-pentafluoro-2-propene, (R-1215xbB1, CF 3 CBr=CF 2 )、(E)-1-bromo-2,3,3,3-tetrafluoropropene, (HBFO-1224ydB(E), CF 3 CF=CHBr)、(Z)-1-bromo-2,3,3,3-tetrafluoropropene, (HBFO-1224ydB(Z), CF 3 CF=CHBr)、2-bromo-3,3,3-trifluoro-propene, (BFO-1233xfB, CF 3 CBr=CH 2 )、trans-DCE / R-1336mzz(Z) mixture, (Suitable mixtures include those disclosed in International Publication No. 2008 / 134061), (trans-DCE / methyl perfluoroheptene ether, (Suitable mixtures include those disclosed in U.S. Patent Publication No. 2012 / 0227764(Al)), (trans-DCE / HFC-43-10mee mixture, (CHCl=CHCl / CF 3 CHFCHFCF 2 CF 3 ), (Suitable mixtures include those disclosed as in U.S. Patent No. 5,196,137), 2-bromo-2-chloro-1,1,1-trifluoroethane, (R-123B1, CHBrClCF 3 ), 2,3-dichloro-3,3-difluoropropene, (R-1232xf, CClF 2 CCl=CH 2 ), (E)-1,1,4,4-tetrafluoro-2-butene, (R-1345mzz(E), CHF 2 CH=CHCHF 2 ), 2-bromo-1,1-difluoroethane, (BDFE, CHF 2 CH 2 Br), 1-chloro-2,3,3,4,4,4-hexafluoro-1-butene, (HCFO-1326yd-Z, CF 3 CF 2 CF=CHCl), 1-chloro-2,3,3-trifluoropropene, (HCFO-1233yd-Z, CHF 2 CF=CHCl), 2-(1,1,2,2-tetrafluoroethoxy)-1-fluoroethylene, (HFO-1345ezcEβγ, CFH=CHOCF 2 CF 2 H), 2,3,3,3-tetrafluoro-1-(1,1,2,2-tetrafluoroethoxy)prop-1-ene, (HFO-1438mzycEγδ, CF 3 CF=CHOCF 2 CF 2 H), 1-(difluoromethoxy)-2,3,3,3-tetrafluoroprop-1-ene, (HFO-1336pzEαβ, CF 3 CF=CHOCF 2 H), 2,3,3-trifluoro-1-(trifluoromethoxy)prop-1-ene, (HFO-1336mzyEαβ, CHF 2 CF=CHOCF 3 ), 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene, (F22E, C 2 F 5 CH=CHC 2 F 5 ), 1,1,1,2,2,3,3,4,4,7,7,8,8,9,9,10,10,10 - octadecafluoro - 5 - decene, (F44E,C 4 F 9 CH=CHC 4 F 9 ), or 1,1,1,2,3,4,4,5,5,5 - decafluoropentane, (HFC - 43 - 10mee,CF 3 CHFCHFCF 2 CF 3 ), and a heat pipe system containing a co - compound comprising at least one of them. Claim 15 The compound of the formula (4) is 1,1,1,2,2,5,5,6,6,7,7,7-dodecafluorohept-2-ene (F23E, C 3 F 7 CH=CHC 2 F 5 ), The system according to claim 14. Claim 16 wherein the co-compound is 1,1,1,4,4,5,5,5-octafluoropent-2-ene (F12E, CF 3 CH=CHC 2 F 5 ), the system according to claim 15. Claim 17 The composition contains 40 to 60% by weight of 1,1,1,2,2,5,5,6,6,7,7,7-dodecafluorohept-2-ene (F23E, C 3 F 7 CH=CHC 2 F 5 ) and 40 to 60% by weight of 1,1,1,4,4,5,5,5 - octafluoropent - 2 - ene (F12E, CF 3 CH=CHC 2 F 5 ), the system according to claim 16. Claim 18 A process for recovering heat from a heat source and generating mechanical energy, comprising: (a) passing a first working fluid through a heat exchanger or an evaporator in a liquid phase, wherein the heat exchanger or the evaporator is in communication with the heat source supplying the heat; (b) removing at least a portion of the first working fluid in a gas phase from the heat exchanger or the evaporator; (c) passing at least a portion of the first working fluid through an expander in a gas phase, wherein at least a portion of the heat is converted into mechanical energy; (d) passing at least a portion of the first working fluid from the expander to a condenser in a vapor phase, wherein at least a portion of the first working fluid in the vapor phase is condensed into a second working fluid in a liquid phase; (e) optionally, in step (a), compressing and mixing the first working fluid and the second working fluid in a liquid phase in a liquid phase; (f) optionally, repeating steps (a) to (e) at least once; wherein at least one of the first working fluid or the second working fluid comprises a composition containing a compound of formula (4). R f CF 3 (CX 5 X 6 CX 7 X 8 ) n CH=CHCX 9 X 10 CX 11 X 12 F(4) In the formula, R f is a C 1 -C 10 perfluorinated alkyl group, wherein, X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 and X 12 are each independently H, Cl, or F, and n is an integer of 0 or 1, X 5 、 X 6 、 X 7 、 X 8 、 X 9 、 X 10 、 X 11 and X 12 The total number of Fs represented by is at least 2, and, 1,1,1,4,4,5,5,5 - Octafluoropent - 2 - ene (F12E, CF 3 CH=CHC 2 F 5 ), (E) - 1,1,1,4,4,4 - Hexafluoro - 2 - butene, (HFO - 1336mzz(E), CF 3 CH=CHCF 3 ), (Z) - 1,1,1,4,4,4 - Hexafluoro - 2 - butene, (HFO - 1336mzz(Z), CF 3 CH=CHCF 3 ), (E) - 2,3 - Bis(trifluoromethyl)oxirane, (HFO - 1336mzz(E)(epoxide), CFCH( - O - )CHCF 3 ), (Z) - 2,3 - Bis(trifluoromethyl)oxirane, (HFO - 1336mzz(Z)(epoxide), CFCH( - O - )CHCF 3 ), HFO - 1234ze(Z), HFO - 1234ye(E), HFO - 1234ye(Z), HFO - 1438mzz(E), HFO - 1438mzz(Z), Heptafluoro - 4 - (trifluoromethyl) - pent - 2 - ene, ((HFO - 153 - 10mzzy), (mixture of HFO - 153 - 10 isomers)), HFO - 162 - 13mcyz, HFO - 162 - 13mczy, (E) - 1,3,4,4,4 - Pentafluoro - 3 - (trifluoromethyl) - 1 - butene, (HFO - 1438ezy(E), CFH=CHCF(CF 3 )) 2 ), (Z) - 1,3,4,4,4 - Pentafluoro - 3 - (trifluoromethyl) - 1 - butene, (HFO - 1438ezy(Z), CFH=CHCF(CF 3 )) 2 ), HFO - 1336ze(E), HFO - 1336ze(Z), HFC - 245fa, HFC - 245ea, HFC - 365mfc, HFC - 43 - 10mee, (E) - 1 - Chloro - 3,3,3 - trifluoro - propene, (HCFO - 1233zd(E), CHCl=CHCF 3 ), (Z) - 1 - Chloro - 3,3,3 - trifluoro - propene, (HCFO - 1233zd(Z), CHCl=CHCF 3 ), HCFO-1224yd(E), HCFO-1224yd(Z), iso-pentane, n-pentane, cyclopentane, n-hexane, cyclohexane, heptane, methyl formate, dimethoxymethane, dimethoxyethane, propanal, methanol, ethanol, isopropanol, N-propanol, trans-1,2-dichloro-ethylene, cis-1,2-dichloro-ethylene, 1-methoxyheptafluoropropane (HFE-7000, CH 3 OCF 2 CF 2 CF 3 ), methyl nonafluorobutyl ether (HFE-71DA, C 4 F 9 OCH 3 ), methoxy-nonafluorobutane (HFE-7100, C 4 F 9 OCH 3 , CH 3 O-3(CF 2 )-CH 3 ), ethoxy-nonafluorobutane (HFE-7200, CH 3 CH 2 OCF 2 CF 2 CF 2 CF 3 , C 4 F 9 OC 2 H 5 ), dodecafluoro-2-methylpentan-3-one (NOVEC-649 or Novec-1230, CF 3 CF 2 C(O)CF(CF 3 ) 2 ), 1,1,1,2,2,3,4,5,5,5-decafluoro-3-methoxy-4-(trifluoromethyl)-pentane (Novec-7300; C 7 H 3 F 13 O; n-C 2 F 5 CF(OCH 3 )CF(CF 3 ) 2 ), siloxane, methyl perfluoroheptene ether, methoxy-perfluoro-heptene ether or MPHE (HFX-110; C 7 F 13 (OCH 3 )), MPPe(HFX-75), perfluorohepta-2-ene / perfluorohepta-3-ene (HFO-161-14myy / HFO-161-14mcyy, PFH, mixture, CF 3 CF=CFCF 2 CF 2 CF 2 CF 3 / CF 3 CF 2 CF=CFCF 2 CF 2 CF 3 )), perfluorohepta-1-ene (FC-141-10cy, CF 2 =CFCF 2 CF 2 CF 2 CF 2 CF 3 ), 1-bromo-1,2,3,3,3-pentafluoropropene, (R-1215ybB, CF 3 CF=CFBr), 2-bromo-1,1,1,3,3-pentafluoro-2-propene, (R-1215xbB1, CF 3 CBr=CF 2 ), (E)-1-bromo-2,3,3,3-tetrafluoropropene, (HBFO-1224ydB(E), CF 3 CF=CHBr), (Z)-1-bromo-2,3,3,3-tetrafluoro-propene, (HBFO-1224ydB(Z), CF 3 CF=CHBr), 2-bromo-3,3,3-trifluoro-propene, (BFO-1233xfB, CF 3 CBr=CH 2 ), trans-DCE / R-1336mzz(Z) mixture, (suitable mixtures include those disclosed in International Publication No. 2008 / 134061), (trans-DCE / methyl perfluoroheptene ether, (suitable mixtures include those disclosed in U.S. Patent Publication No. 2012 / 0227764(Al)), (trans-DCE / HFC-43-10mee mixture, (CHCl=CHCl / CF 3 CHFCHFCF 2 CF 3 ), (Suitable mixtures include those disclosed as in U.S. Patent No. 5,196,137), 2-bromo-2-chloro-1,1,1-trifluoroethane, (R-123B1, CHBrClCF 3 ), 2,3-dichloro-3,3-difluoropropene, (R-1232xf, CClF 2 CCl=CH 2 ), (E)-1,1,4,4-tetrafluoro-2-butene, (R-1345mzz(E), CHF 2 CH=CHCHF 2 ), 2-bromo-1,1-difluoroethane, (BDFE, CHF 2 CH 2 Br), 1-chloro-2,3,3,4,4,4-hexafluoro-1-butene, (HCFO-1326yd-Z, CF 3 CF 2 CF=CHCl), 1-chloro-2,3,3-trifluoropropene, (HCFO-1233yd-Z, CHF 2 CF=CHCl), 2-(1,1,2,2-tetrafluoroethoxy)-1-fluoroethylene, (HFO-1345ezcEβγ, CFH=CHOCF 2 CF 2 H), 2,3,3,3-tetrafluoro-1-(1,1,2,2-tetrafluoroethoxy)prop-1-ene, (HFO-1438mzycEγδ, CF 3 CF=CHOCF 2 CF 2 H), 1-(difluoromethoxy)-2,3,3,3-tetrafluoroprop-1-ene, (HFO-1336pzEαβ, CF 3 CF=CHOCF 2 H), 2,3,3-trifluoro-1-(trifluoromethoxy)prop-1-ene, (HFO-1336mzyEαβ, CHF 2 CF=CHOCF 3 ), 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene, (F22E, C 2 F 5 CH=CHC 2 F 5 ), 1,1,1,2,2,3,3,4,4,7,7,8,8,9,9,10,10,10 - octadecafluoro - 5 - decene, (F44E,C 4 F 9 CH=CHC 4 F 9 ), or 1,1,1,2,3,4,4,5,5,5 - decafluoropentane, (HFC - 43 - 10mee,CF 3 CHFCHFCF 2 CF 3 ), and a process comprising a co - compound containing at least one of them. Claim 19 The compound of formula (4) is 1,1,1,2,2,5,5,6,6,7,7,7-dodecafluorohept-2-ene (F23E, C 3 F 7 CH=CHC 2 F 5 ), The process according to claim 18. Claim 20 The co-compound is 1,1,1,4,4,5,5,5-octafluoropent-2-ene (F12E, CF 3 CH=CHC 2 F 5 ), and the process according to claim 19. Claim 21 The composition contains 40 to 60% by weight of 1,1,1,2,2,5,5,6,6,7,7,7-dodecafluorohept-2-ene (F23E, C 3 F 7 CH=CHC 2 F 5 ) and 40 to 60% by weight of 1,1,1,4,4,5,5,5 - octafluoropent - 2 - ene (F12E, CF 3 CH=CHC 2 F 5 ), the process according to claim 20. Claim 22 A high-temperature heat pump device, the device comprising: (a) a first heat exchanger through which a working fluid flows and is heated; (b) a compressor in fluid communication with the first heat exchanger for compressing the heated working fluid to a higher pressure; (c) a second heat exchanger in fluid communication with the compressor through which the high-pressure working fluid flows and is cooled; and (d) a pressure reducing device in fluid communication with the second heat exchanger for reducing the pressure of the cooled working fluid and further in fluid communication with the evaporator such that the working fluid later repeatedly flows through components (a), (b), (c) and (d) in a cycle. The working fluid includes a composition containing a compound of formula (4). R f CF 3 (CX 5 X 6 CX 7 X 8 ) n CH=CHCX 9 X 10 CX 11 X 12 F(4) In the formula, R f is a C 1 -C 10 perfluorinated alkyl group, wherein X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 and X 12 are each independently H, Cl, or F, and n is an integer of 0 or 1, X 5 、 X 6 、 X 7 、 X 8 、 X 9 、 X 10 、 X 11 and X 12 The total number of F represented by is at least 2, and 1,1,1,4,4,5,5,5 - Octafluoropent - 2 - ene (F12E, CF 3 CH=CHC 2 F 5 ), (E) - 1,1,1,4,4,4 - Hexafluoro - 2 - butene, (HFO - 1336mzz(E), CF 3 CH=CHCF 3 ), (Z) - 1,1,1,4,4,4 - Hexafluoro - 2 - butene, (HFO - 1336mzz(Z), CF 3 CH=CHCF 3 ), (E) - 2,3 - Bis(trifluoromethyl)oxirane, (HFO - 1336mzz(E)(epoxide), CFCH( - O - )CHCF 3 ), (Z) - 2,3 - Bis(trifluoromethyl)oxirane, (HFO - 1336mzz(Z)(epoxide), CFCH( - O - )CHCF 3 ), HFO - 1234ze(Z), HFO - 1234ye(E), HFO - 1234ye(Z), HFO - 1438mzz(E), HFO - 1438mzz(Z), Heptafluoro - 4 - (trifluoromethyl) - pent - 2 - ene, ((HFO - 153 - 10mzzy), (mixture of HFO - 153 - 10 isomers)), HFO - 162 - 13mcyz, HFO - 162 - 13mczy, (E) - 1,3,4,4,4 - Pentafluoro - 3 - (trifluoromethyl) - 1 - butene, (HFO - 1438ezy(E), CFH=CHCF(CF 3 )) 2 ), (Z) - 1,3,4,4,4 - Pentafluoro - 3 - (trifluoromethyl) - 1 - butene, (HFO - 1438ezy(Z), CFH=CHCF(CF 3 )) 2 ), HFO - 1336ze(E), HFO - 1336ze(Z), HFC - 245fa, HFC - 245ea, HFC - 365mfc, HFC - 43 - 10mee, (E) - 1 - Chloro - 3,3,3 - trifluoro - propene, (HCFO - 1233zd(E), CHCl=CHCF 3 ), (Z) - 1 - Chloro - 3,3,3 - trifluoro - propene, (HCFO - 1233zd(Z), CHCl=CHCF 3 ), HCFO-1224yd(E), HCFO-1224yd(Z), iso-pentane, n-pentane, cyclopentane, n-hexane, cyclohexane, heptane, methyl formate, dimethoxymethane, dimethoxyethane, propanal, methanol, ethanol, isopropanol, N-propanol, trans-1,2-dichloro-ethylene, cis-1,2-dichloro-ethylene, 1-methoxyheptafluoropropane (HFE-7000, CH 3 OCF 2 CF 2 CF 3 ), methyl nonafluorobutyl ether (HFE-71DA, C 4 F 9 OCH 3 ), methoxy-nonafluorobutane (HFE-7100, C 4 F 9 OCH 3 , CH 3 O-3(CF 2 )-CH 3 ), ethoxy-nonafluorobutane (HFE-7200, CH 3 CH 2 OCF 2 CF 2 CF 2 CF 3 , C 4 F 9 OC 2 H 5 ), dodecafluoro-2-methylpentan-3-one (NOVEC-649 or Novec-1230, CF 3 CF 2 C(O)CF(CF 3 ) 2 ), 1,1,1,2,2,3,4,5,5,5-decafluoro-3-methoxy-4-(trifluoromethyl)-pentane (Novec-7300; C 7 H 3 F 13 O; n-C 2 F 5 CF(OCH 3 )CF(CF 3 ) 2 ), siloxane, methyl perfluoroheptene ether, methoxy-perfluoro-heptene ether or MPHE (HFX-110; C 7 F 13 (OCH 3 )), MPPe(HFX-75), perfluorohepta-2-ene / perfluorohepta-3-ene (HFO-161-14myy / HFO-161-14mcyy, PFH, mixture, CF 3 CF=CFCF 2 CF 2 CF 2 CF 3 / CF 3 CF 2 CF=CFCF 2 CF 2 CF 3 )), perfluorohepta-1-ene (FC-141-10cy, CF 2 =CFCF 2 CF 2 CF 2 CF 2 CF 3 ), 1-bromo-1,2,3,3,3-pentafluoropropene, (R-1215ybB, CF 3 CF=CFBr), 2-bromo-1,1,1,3,3-pentafluoro-2-propene, (R-1215xbB1, CF 3 CBr=CF 2 ), (E)-1-bromo-2,3,3,3-tetrafluoropropene, (HBFO-1224ydB(E), CF 3 CF=CHBr), (Z)-1-bromo-2,3,3,3-tetrafluoropropene, (HBFO-1224ydB(Z), CF 3 CF=CHBr), 2-bromo-3,3,3-trifluoro-propene, (BFO-1233xfB, CF 3 CBr=CH 2 ), trans-DCE / R-1336mzz(Z) mixture, (suitable mixtures include those disclosed in International Publication No. 2008 / 134061), (trans-DCE / methyl perfluoroheptene ether, (suitable mixtures include those disclosed in U.S. Patent Publication No. 2012 / 0227764(Al)), (trans-DCE / HFC-43-10mee mixture, (CHCl=CHCl / CF 3 CHFCHFCF 2 CF 3 ), (Examples of suitable mixtures include those disclosed as in Japanese Patent Publication No. 5196137), 2-bromo-2-chloro-1,1,1-trifluoroethane, (R-123B1, CHBrClCF 3 ), 2,3-dichloro-3,3-difluoropropene, (R-1232xf, CClF 2 CCl=CH 2 ), (E)-1,1,4,4-tetrafluoro-2-butene, (R-1345mzz(E), CHF 2 CH=CHCHF 2 ), 2-bromo-1,1-difluoroethane, (BDFE, CHF 2 CH 2 Br), 1-chloro-2,3,3,4,4,4-hexafluoro-1-butene, (HCFO-1326yd-Z, CF 3 CF 2 CF=CHCl), 1-chloro-2,3,3-trifluoropropene, (HCFO-1233yd-Z, CHF 2 CF=CHCl), 2-(1,1,2,2-tetrafluoroethoxy)-1-fluoroethylene, (HFO-1345ezcEβγ, CFH=CHOCF 2 CF 2 H), 2,3,3,3-tetrafluoro-1-(1,1,2,2-tetrafluoroethoxy)prop-1-ene, (HFO-1438mzycEγδ, CF 3 CF=CHOCF 2 CF 2 H), 1-(difluoromethoxy)-2,3,3,3-tetrafluoroprop-1-ene, (HFO-1336pzEαβ, CF 3 CF=CHOCF 2 H), 2,3,3-trifluoro-1-(trifluoromethoxy)prop-1-ene, (HFO-1336mzyEαβ, CHF 2 CF=CHOCF 3 ), 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene, (F22E, C 2 F 5 CH=CHC 2 F 5 ), 1,1,1,2,2,3,3,4,4,7,7,8,8,9,9,10,10,10 - octadecafluoro - 5 - decene, (F44E,C 4 F 9 CH=CHC 4 F 9 ), or 1,1,1,2,3,4,4,5,5,5 - decafluoropentane, (HFC - 43 - 10mee,CF 3 CHFCHFCF 2 CF 3 ) and comprising a co - compound containing at least one of them, a high - temperature heat pump device. Claim 23 The compound of the formula (4) is 1,1,1,2,2,5,5,6,6,7,7,7-dodecafluorohept-2-ene (F23E, C 3 F 7 CH=CHC 2 F 5 ), The high-temperature heat pump device according to claim 22. Claim 24 The co-compound is 1,1,1,4,4,5,5,5-octafluoropent-2-ene (F12E, CF 3 CH=CHC 2 F 5 ), The high-temperature heat pump device according to claim 23. Claim 25 The composition contains 40 to 60% by weight of 1,1,1,2,2,5,5,6,6,7,7,7-dodecafluorohept-2-ene (F23E, C 3 F 7 CH=CHC 2 F 5 ) and 40 to 60% by weight of 1,1,1,4,4,5,5,5-octafluoropent-2-ene (F12E, CF 3 CH=CHC 2 F 5 ) and is the high-temperature heat pump device according to claim 24.

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