Synthesis of HFO-153-10MCZZ involving catalytic coupling of HCFC-225CA or CFC-215CB

Abstract

In one embodiment, a method for producing fluoroolefins includes coupling 3,3-dichloro-1,1,1,2,2-pentafluoropropane (CF3-CF2-CHCl2) in the presence of a catalyst in the liquid phase to form a composition comprising 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (CF3CF2CH=CHCF2CF3). In another embodiment, a method for producing fluoroolefins includes coupling 1,1,1-trichloropentafluoropropane (CF3-CF2-CCl3) in the presence of a first catalyst in the gas phase to form a composition comprising 3,4-dichloro-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (CF3-CF2-CCl=CCl-CF2-CF3). The method further includes coupling CF3CF2CH m Cl 3-m and chlorine (Cl2) to form CF3-CF2-CCl3. The method may further include hydrodechlorinating 3,4-dichloro-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene with hydrogen (H2) in the presence of a second catalyst in the gas phase to form a composition comprising CF3CF2CH=CHCF2CF3 and 3-chloro-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (CF3CF2CCl=CHCF2CF3).

Description

[Technical field]

[0001] This application claims the benefit of Application No. 63 / 313,773, filed February 25, 2022. The disclosure of Application No. 63 / 313,773 is incorporated herein by reference in its entirety.

[0002] FIELD OF THEINVENTION The present disclosure relates to the production of fluorinated alkene compounds. More specifically, the present disclosure relates to the production of hydrofluoroolefins (HFOs) 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (HFO-153-10mczz; CF 3 CF 2 CH=CHCF 2 CF 3 ) regarding. [Background technology]

[0003] Increasing societal awareness of the environmental impacts of fossil fuel extraction, transportation, and use has led to an increase in atmospheric CO 2 There is a new driver for environmental sustainability in the form of regulations and reductions in emissions of equivalents. New working fluids with low Global Warming Potential (GWP) and Ozone Depletion Potential (ODP) for both existing and new applications in the thermal management segment are required to comply with these new regulations. Summary of the Invention [Means for solving the problem]

[0004] In one embodiment, the method for producing fluoroolefins comprises the steps of: 3 -CF 2 -CHCl 2 ) is coupled in the liquid phase in the presence of a catalyst to give 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (HFO-153-10mczz; CF 3 CF 2 CH=CHCF 2 CF 3).

[0005] In another embodiment, a method for producing a fluoroolefin comprises the steps of: reacting 1,1,1-trichloropentafluoropropane (CF 3 -CF 2 -CCl 3 ) to give 3,4-dichloro-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (CF 3 -CF 2 -CCl=CCl-CF 2 -CF 3 ).

[0006] In yet another embodiment, the method for producing fluoroolefins comprises the steps of: 3 CF 2 CH n Cl 3-n and chlorine (Cl 2 ) to CF 3 -CF 2 -CCl 3 wherein n is an integer selected from the group consisting of 1, 2, and 3.

[0007] In yet another embodiment, the method for producing a fluoroolefin comprises reacting a fluoroolefin of formula (1)C in the presence of a first catalyst. 2 F 5 CH n Cl 3-n (1) (wherein n is 0 or 1) is coupled to a compound of formula (2)C 2 F 5 CX 1 =CX 2 C 2 F 5 (2) (wherein, when n is 0, X 1 and X 2 is Cl, and when n is 1, X 1 and X 2 is H.

[0008] The present invention includes the following aspects and embodiments. In one embodiment, a method for producing a fluoroolefin is disclosed herein. The method described herein comprises the step of producing 3,3-dichloro-1,1,1,2,2-pentafluoropropane (CF 3 -CF 2 -CHCl 2 ) is coupled in the liquid phase in the presence of a catalyst to give 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (CF 3 CF 2 CH=CHCF 2 CF 3 ).

[0009] Also disclosed herein, according to any of the preceding embodiments, is a method, wherein the coupling step is carried out in an aprotic solvent.

[0010] Also disclosed herein, in accordance with the foregoing embodiments, is a method, wherein the aprotic solvent is selected from the group consisting of dimethylformamide, dimethylacetamide, dimethylsulfoxide, and N-methylpyrrolidone.

[0011] Also disclosed herein, in accordance with any of the preceding embodiments, is a method, wherein the catalyst is selected from the group consisting of 2,2-bipyridine, copper(I) salts, and combinations thereof.

[0012] Also disclosed herein, in accordance with the foregoing embodiments, is a method, wherein the copper(I) salt is selected from the group consisting of CuCl, CuBr, CuI, and copper(I) acetate.

[0013] Also disclosed herein, according to any of the foregoing embodiments, is a method wherein the contacting is carried out in the liquid phase or the gas phase.

[0014] In one embodiment, a method for producing a fluoroolefin is disclosed herein. The method described herein comprises the step of producing 1,1,1-trichloropentafluoropropane (CF) in the gas phase in the presence of a first catalyst. 3 -CF 2 -CCl 3) to give 3,4-dichloro-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (CF 3 -CF 2 -CCl=CCl-CF 2 -CF 3 ).

[0015] Also disclosed herein is a method, according to any combination of the preceding embodiments, wherein the first catalyst comprises Ru / SiC.

[0016] According to any of the above-mentioned embodiments, in the gas phase, CF 3 CF 2 CH n Cl 3-n and chlorine (Cl 2 ) to CF 3 -CF 2 -CCl 3 Also disclosed herein are methods further comprising forming: wherein n is an integer selected from the group consisting of 1, 2, and 3. In some embodiments, the forming step is performed in the absence of a catalyst. In other embodiments, the forming step is performed in the presence of a catalyst selected from the group consisting of an activated carbon catalyst, a metal halide catalyst, a metal oxide catalyst, a metal oxyhalide catalyst, and combinations thereof.

[0017] According to any of the foregoing embodiments, 3,4-dichloro-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene is converted to hydrogen (H) in the gas phase in the presence of a second catalyst. 2 ) to give 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (CF 3 CF 2 CH=CHCF 2 CF 3 ) and 3-chloro-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (CF 3 CF 2 CCl=CHCF 2 CF 3 Also disclosed herein are methods further comprising forming a composition comprising:

[0018] Also disclosed herein, in accordance with the foregoing embodiment, is a method wherein the second catalyst comprises a nickel-containing catalyst.

[0019] Also disclosed herein, in accordance with the foregoing embodiment, is a method wherein the second catalyst comprises an iridium / carbon catalyst.

[0020] Also disclosed herein, in accordance with the foregoing embodiments, is a method wherein the second catalyst comprises a bimetallic catalyst on a carbon support.

[0021] According to any of the above-mentioned embodiments, hydrogen (H 2 ) to obtain 3-chloro-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (CF 3 CF 2 CCl=CHCF 2 CF 3 ) is hydrodechlorinated to give 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (CF 3 CF 2 CH=CHCF 2 CF 3 Also disclosed herein are methods further comprising forming a

[0022] Also disclosed herein, in accordance with the foregoing embodiments, is a method, wherein the third catalyst is selected from the group consisting of a nickel-containing catalyst, an iridium / carbon catalyst, a bimetallic catalyst on a carbon support, a gold catalyst on a support, a platinum catalyst on a support, a palladium catalyst on a support, a copper catalyst on a support, and combinations thereof.

[0023] Also disclosed herein, according to any of the foregoing embodiments, is a method wherein the contacting is carried out in the liquid phase or the gas phase.

[0024] In one embodiment, a method for producing fluoroolefins is disclosed herein. The method described herein comprises reacting CF 3 CF 2 CH n Cl 3-n and chlorine (Cl 2) to CF 3 -CF 2 -CCl 3 wherein n is an integer selected from the group consisting of 1, 2 and 3.

[0025] Also disclosed herein, in accordance with any of the foregoing embodiments, is a method, wherein the forming step is carried out in the absence of a catalyst.

[0026] In accordance with the foregoing embodiment, also disclosed herein is a method wherein n is 1.

[0027] In accordance with the foregoing embodiment, also disclosed herein is a method wherein n is 3.

[0028] In one embodiment, disclosed herein is a method for producing a fluoroolefin. The method disclosed herein comprises the step of: 2 F 5 CH n Cl 3-n (1), where n is 0 or 1, in the presence of a first catalyst to produce a compound of formula (2) 2 F 5 CX 1 =CX 2 C 2 F 5 (2) (wherein, when n is 0, X 1 and X 2 is Cl, and when n is 1, X 1 and X 2 is H.

[0029] According to the above embodiment, n is 1 and X 1 and X 2 Also disclosed herein are methods, wherein is H and the coupling is carried out in solution phase.

[0030] Also disclosed herein, according to any of the preceding embodiments, is a method, wherein the coupling step is carried out in an aprotic solvent.

[0031] Also disclosed herein, in accordance with the foregoing embodiments, is a method, wherein the aprotic solvent is selected from the group consisting of dimethylformamide, dimethylacetamide, dimethylsulfoxide, and N-methylpyrrolidone.

[0032] Also disclosed herein, in accordance with any of the preceding embodiments, is a method, wherein the first catalyst is selected from the group consisting of 2,2-bipyridine, a copper(I) salt, and combinations thereof.

[0033] Also disclosed herein, in accordance with the foregoing embodiments, is a method, wherein the copper(I) salt is selected from the group consisting of CuCl, CuBr, CuI, and copper(I) acetate.

[0034] Also disclosed herein, according to any of the foregoing embodiments, is a method, wherein the coupling step is carried out in the liquid phase or in the gas phase.

[0035] According to any of the foregoing embodiments, n is 0 and X 1 and X 2 Also disclosed herein are methods wherein is Cl and the coupling step is carried out in the gas phase.

[0036] Also disclosed herein is a method, according to any combination of the preceding embodiments, wherein the first catalyst comprises Ru / SiC.

[0037] According to the above embodiment, in the gas phase, CF 3 CF 2 CH m Cl 3-m and chlorine (Cl 2 ) to CF 3 -CF 2 -CCl 3 Also disclosed herein are methods further comprising forming: wherein m is an integer selected from the group consisting of 1, 2, and 3. In some embodiments, the forming step is performed in the absence of a catalyst. In other embodiments, the forming step is performed in the presence of a catalyst selected from the group consisting of an activated carbon catalyst, a metal halide catalyst, a metal oxide catalyst, a metal oxyhalide catalyst, and combinations thereof.

[0038] According to the above embodiment, hydrogen (H 2 ) was used to hydrodechlorinate 3,4-dichloro-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene to obtain 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (CF 3 CF 2 CH=CHCF 2 CF 3 ) and 3-chloro-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (CF 3 CF 2 CCl=CHCF 2 CF 3 Also disclosed herein are methods further comprising forming a composition comprising:

[0039] Also disclosed herein, in accordance with the foregoing embodiments, is a method, wherein the second catalyst is selected from the group consisting of a nickel-containing catalyst, an iridium / carbon catalyst, and a bimetallic catalyst on a carbon support.

[0040] According to any of the above-mentioned embodiments, hydrogen (H 2 ) to obtain 3-chloro-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (CF 3 CF 2 CCl=CHCF 2 CF 3 ) is hydrodechlorinated to give 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (CF 3 CF 2 CH=CHCF 2 CF 3 Also disclosed herein are methods further comprising forming a

[0041] Also disclosed herein, in accordance with the foregoing embodiments, is a method, wherein the third catalyst is selected from the group consisting of a nickel-containing catalyst, an iridium / carbon catalyst, a bimetallic catalyst on a carbon support, a gold catalyst on a support, a platinum catalyst on a support, a palladium catalyst on a support, a copper catalyst on a support, and combinations thereof.

[0042] Also disclosed herein, in accordance with any of the foregoing embodiments, is a composition formed by any of the foregoing methods.

[0043] According to a particular embodiment of the present invention, fluoroolefin EC 2 F 5 CF=CFC 2 F 5 (E-HFO-151-12mcyy), EC 2 F 5 CH=CHC 2 F 5 (E-HFO-153-10mczz), C 3 F 7 CH=CHCF 3 (HFO-153-10mzz), (CF 3 ) 2 CFCH=CHCF 3 (HFO-153-10mzzy), ZC 2 F 5 CF=CFC 2 F 5 (z-FO-151-12mcyZ) is eHFO-153-10mzcc and is used for thermal energy management of electrical components.

[0044] According to another embodiment, EC 2 F 5 CF=CFC 2 F 5 (E-HFO-151-12mcyy), EC 2 F 5 CH=CHC 2 F 5 (E-HFO-153-10mczz), C 3 F 7 CH=CHCF 3 (HFO-153-10mczz), (CF 3 ) 2 CFCH=CHCF 3 (HFO-153-10mzzy), ZC 2 F 5 CF=CFC 2 F 5Fluoroolefins including (z-FO-151-12mcyZ) are used with electrical components requiring thermal management such as electronic devices, computers, servers, and data centers, as well as heat transfer components found in batteries, electric motors, hybrid electric vehicles (HEVs), mild hybrid electric vehicles (M HEVs), plug-in hybrid electric vehicles (PHEVs), or one of the electric vehicles (EVs), heat pump systems in these vehicles, and electrified mass transportation.

[0045] Other features and advantages of the present invention will become apparent from the following more detailed description, which illustrates, by way of example, the principles of the invention. [Brief description of the drawings]

[0046] [Figure 1] FIG. 1 is a schematic diagram in which one of the fluoroolefins, including the E / Z fluoroolefins described herein, is used as the circulated thermal fluid. [Diagram 2] FIG. 1 is a schematic diagram of one embodiment of immersion cooling using E / Z fluoroolefins described herein. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0047] EC that can be used alone or in blends 2 F 5 CF=CFC 2 F 5 (E-HFO-151-12mcyy), EC 2 F 5 CH=CHC 2 F 5 ,(E-HFO-153-10mczz),C 3 F 7 CH=CHCF 3 (HFO-153-10mzz), (CF 3 ) 2 CFCH=CHCF 3 (HFO-153-10mzzy), or ZC 2 F 5 CF=CFC 2 F5 (z-FO-151-12mcyZ).

[0048] As used herein, the terms "comprises," "comprising," "includes," "including," "has," "having," or any other variation thereof, are intended to cover non-exclusive inclusions. For example, a composition, process, method, article, or device that includes recited elements is not necessarily limited to only those elements, but may include other elements not expressly recited or inherent in such composition, process, method, article, device, etc. Furthermore, unless expressly stated to the contrary, "or" refers to an inclusive "or," not an exclusive "or." For example, a 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).

[0049] The transitional phrase "consisting of" excludes any unspecified element, step, or ingredient. When in a claim, such a phrase closes the claim to including materials other than those recited, except for impurities ordinarily accompanying the materials. When the phrase "consists of" appears within a clause in the body of a claim rather than immediately following the introductory paragraph, the phrase is limited to only the elements recited in that clause and does not exclude other elements from the claim as a whole.

[0050] The transitional phrase "consisting essentially of" is used to define compositions, methods, and methods that include materials, steps, mechanisms, components, or elements in addition to those literally disclosed, provided that these additionally included materials, steps, mechanisms, components, or elements do not materially affect the basic and novel feature(s) of the claimed invention, particularly the mechanism of action for achieving any desired result of the inventive process. The term "consisting essentially of" has a meaning intermediate between "comprising" and "consisting of."

[0051] A synthetic method for producing fluorinated alkenes that overcomes the above limitations is provided. 1,1,1,2,2,5,5,6,6,6-Decafluoro-3-hexene (HFO-153-10mczz; CF 3 CF 2 CH=CHCF 2 CF 3 Disclosed herein are synthetic routes for forming compositions comprising:

[0052] For example, embodiments of the present disclosure provide a method for producing fluorinated alkenes. More specifically, the present disclosure provides a method for producing fluorinated alkenes having perfluoroalkyl chains. The resulting fluorinated alkenes are environmentally friendly, exhibit low GWP and zero ozone depletion potential (ODP), are non-flammable, non-conductive, and exhibit low liquid viscosity.

[0053] The disclosed methods and compositions are directed to the production of 3,4-dichloro-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (CFO-151-10mcxx; CF 3 -CF 2 -CCl=CCl-CF 2 -CF 3 ), 3-chloro-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (HCFO-152-10mcxz; CF 3 CF 2 CCl=CHCF 2 CF 3), and / or 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (HFO-153-10mczz; CF 3 CF 2 CH=CHCF 2 CF 3 Each of these compounds has an E isomer form (E-CFO-151-10mcxx, E-HCFO-152-10mcxz, and E-HFO153-10mczz, respectively) and a Z isomer form (Z-CFO-151-10mcxx, Z-HCFO152-10mcxz, and Z-HFO-153-10mczz, respectively). As used herein, when the form is not specified, the composition may include the E isomer, the Z isomer, or any combination thereof.

[0054] In some embodiments, the E isomer is preferred. In some embodiments, the starting materials and / or process conditions are selected to increase the formation of the E isomer over the Z isomer. In some embodiments, the process includes a step of separating the E isomer from the Z isomer.

[0055] The first method for producing fluoroolefins is the use of 3,3-dichloro-1,1,1,2,2-pentafluoropropane (HCFC-225ca; CF 3 -CF 2 -CHCl 2 ) in the presence of a catalyst in a liquid phase in a reactor, 1,1,1,2,2,5,5,6,6,6-Decafluoro-3-hexene (HFO-153-10mczz; CF 3 CF 2 CH=CHCF 2 CF 3 In some embodiments, the reactor is a Hastelloy® shaker tube. In some embodiments, copper powder is also provided in the reactor.

[0056] In exemplary embodiments, the coupling step is carried out at a temperature ranging from about 50° C. to about 140° C., or from about 60° C. to about 120° C., or from about 80° C. to about 120° C., or any value, range, or subrange therebetween.

[0057] In some embodiments, the solution phase coupling is carried out in an aprotic solvent. Suitable aprotic solvents can include, but are not limited to, dimethylformamide, dimethylacetamide, dimethylsulfoxide, or N-methylpyrrolidone.

[0058] In some embodiments, the catalyst is 2,2-bipyridine. In other embodiments, the catalyst is a copper(I) salt. In other embodiments, the catalyst is a combination of 2,2-bipyridine and a copper(I) salt. Suitable copper(I) salts may include, but are not limited to, CuCl, CuBr, CuI, and copper(I) acetate.

[0059] In some embodiments, the HCFC-225ca starting material may be mixed with other fluorinated compounds, such as 1,3-dichloro-1,1,2,2,3-pentafluoropropane (HCFC-225cb; CCIF 2 -CF 2 -CHClF) and / or 2,2-dichloro-1,1,1,3,3-pentafluoropropane (HCFC-225aa; CF 3 -CCl 2 -CHF 2 ) is also included.

[0060] In some embodiments, the first method further comprises purifying the HFO-153-10mczz.

[0061] A second method for producing fluoroolefins is the synthesis of 1,1,1-trichloropentafluoropropane (CFC-215cb; in the gas phase, CF 3 -CF 2 -CCl 3) is coupled in a reactor in the presence of a first catalyst to produce 3,4-dichloro-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (CFO-151-10mcxx; CF 3 -CF 2 -CCl=CCl-CF 2 -CF 3 In some embodiments, the reactor is an alloy tube reactor, such as, for example, a Monel® tube reactor.

[0062] In some embodiments, the first catalyst comprises Ru / SiC. In some embodiments, hydrogen gas (H 2 ) is also fed to the reactor.

[0063] In exemplary embodiments, the vapor phase coupling is carried out at a temperature in the range of about 100° C. to about 140° C., or about 125° C. to about 135° C., or about 127° C. to about 133° C., or about 130° C., or any value, range, or subrange therebetween.

[0064] In some embodiments, the gas phase coupling is conducted at a pressure of about 0 psig to about 175 psig, or about 125 psig to about 170 psig, or about 140 psig to about 160 psig, or about 145 psig to about 155 psig, or about 150 psig, or any value, range, or subrange therebetween.

[0065] In some embodiments, the gas phase coupling is carried out for a contact time ranging from about 10 seconds to about 30 minutes. The catalytic contact time can range from about 50 seconds to about 1 minute, from about 70 seconds to about 30 minutes, and sometimes from about 80 minutes to about 20 minutes.

[0066] In some embodiments, the second method also includes reacting a molecule of formula (2), CF, in the gas phase. 3 CF 2 CH n Cl 3-nin a reactor to form CFC-215cb, where n is 1, 2, or 3. In some embodiments, the reactor is a metal alloy reactor. In some embodiments, the metal alloy reactor is an Inconel® tube. In some embodiments, the chlorination step is carried out in the absence of a catalyst. In some embodiments, the chlorination step is carried out in the presence of a catalyst. In some embodiments, the catalyst is an activated carbon catalyst, a metal halide catalyst, a metal oxide catalyst, and / or a metal oxyhalide catalyst, each of which may be provided with or without a support. In some embodiments, the chlorination step is carried out using ultraviolet (UV) radiation.

[0067] In some embodiments, the molecule of formula (2) is HCFC-225ca. In some embodiments, the HCFC-225ca starting material can also be chlorinated to produce other fluorinated compounds, such as 1,1,3-trichloropentafluoropropane (CFC-215ca; CCIF 2 -CF 2 -CCl 2 F) contains HCFC-225cb.

[0068] In some embodiments, the molecule of formula (2) is selected from the group consisting of 1,1,1,2,2-pentafluoropropane, 1,1,1,2,2-pentafluoro-3-chloropropane (HCFC-235cb; CF 3 -CF 2 -CH 2 Cl).

[0069] In some embodiments, the molecule of formula (2) is 1,1,1,2,2-pentafluoropropane (HFC-245cb; CF 3 -CF 2 -CH 3 ).

[0070] In some embodiments, chlorine gas (Cl 2 ) is also fed to the reactor for the chlorination reaction.

[0071] In some embodiments, the vapor phase chlorination is carried out at a temperature ranging from about 200°C to about 300°C.

[0072] In some embodiments, the gas phase chlorination is carried out for a contact time ranging from about 10 seconds to about 2 hours, or from about 1 minute to about 1 hour, or from about 5 minutes to about 30 minutes, or any value, range, or subrange therebetween.

[0073] In some embodiments, the vapor phase chlorination is carried out under a pressure ranging from about atmospheric pressure (0 psig) to about 200 psig (about 1.38 MPa).

[0074] In some embodiments, the second process comprises reacting hydrogen (H 2 ) in the gas phase in the presence of a second catalyst. 2 ) to hydrodechlorinate CFO-153-10mcxx in a reactor to produce HFO-151-10mczz and 3-chloro-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (CF 3 CF 2 CCl=CHCF 2 CF 3 ).

[0075] In some embodiments, the second catalyst comprises a nickel-containing catalyst. When the second catalyst comprises a nickel-containing catalyst, the vapor phase hydrodechlorination is preferably carried out for a contact time in the range of about 50 seconds to about 80 seconds.

[0076] In some embodiments, the second catalyst comprises an iridium / carbon catalyst. When the second catalyst comprises an iridium / carbon catalyst, the gas phase hydrodechlorination is preferably carried out for a contact time ranging from about 50 seconds to about 300 seconds.

[0077] In some embodiments, the second catalyst comprises a bimetallic catalyst on a carbon support. When the second catalyst comprises a bimetallic catalyst on a carbon support, the gas phase hydrodechlorination is preferably carried out for a contact time in the range of about 50 seconds to about 130 seconds.

[0078] In some embodiments, the vapor phase hydrodechlorination is carried out at a temperature in the range of about 70° C. to about 270° C., or about 120° C. to about 270° C., or about 120° C. to about 140° C., or about 190° C. to about 210° C., or about 240° C. to about 260° C., or about 130° C., or about 200° C., or about 250° C., or any value, range, or subrange therebetween.

[0079] In some embodiments, the vapor phase hydrodechlorination is conducted at a pressure of from about 0 psig to about 175 psig, or from about 130 psig to about 170 psig, or from about 140 psig to about 160 psig, or from about 145 psig to about 155 psig, or about 150 psig, or any value, range, or subrange therebetween.

[0080] In some embodiments, hydrogen gas (H 2 ) is also fed to the reactor for the hydrodechlorination reaction.

[0081] In some embodiments, the second process comprises the step of reacting hydrogen (H 2 ) in the gas phase in the presence of a third catalyst. 2 ) to CF 3 CF 2 CCl=CHCF 2 CF 3 to form HFO-153-10mczz.

[0082] In some embodiments, the third catalyst comprises a nickel-containing catalyst, an iridium / carbon catalyst, a bimetallic catalyst on a carbon support, a gold catalyst on carbon or other support, a platinum catalyst on carbon or other support, a palladium catalyst on carbon or other support, and / or a copper catalyst on carbon or other support.

[0083] In some embodiments, the second method further comprises purifying HFO-153-10mczz. In some embodiments, the purifying step comprises purifying E-HFO-153-10mczz.

[0084] In some embodiments, the third method comprises reacting a molecule of formula (2), CF, in the gas phase.3 CF 2 CH n Cl 3-n in a reactor to form CFC-215cb, where n is 1, 2, or 3. In some embodiments, the reactor is a metal alloy reactor. In some embodiments, the metal alloy reactor is an Inconel® tube. In some embodiments, the chlorination step is carried out in the absence of a catalyst.

[0085] In some embodiments, the composition is formed by any of the methods described above.

[0086] HFO-153-10mczz can be isolated and optionally purified prior to use. Suitable applications for HFO-153-10mczz can include, but are not limited to, working fluids in systems utilizing thermodynamic cycles, cooling media, specialty fluids for thermal management, submersion cooling fluids, reactive intermediates, refrigerants, heat transfer fluids with or without phase change, carrier fluids, or solvents.

[0087] The good dielectric properties and suitable boiling point make E-HFO-153-10mczz a potential candidate for use as a cooling medium for lithium-ion batteries (LiBs) in automobiles.

[0088] In another exemplary embodiment, the properties of E-HFO-153-10mczz provide benefits in carrier fluid applications: E-HFO-153-10mczz exhibits favorable properties that allow it to provide traditional carrier fluid behavior for the deposition or removal of soluble compounds, readily dissolving, transporting, and / or depositing certain media.

[0089] In other exemplary embodiments, E-HFO-153-10mczz is used as a solvent for any of a number of different applications. For example, the properties of E-HFO-153-10mczz may be beneficial in solvent cleaning applications. Additional solvent-based applications of E-HFO-153-10mczz include as a fluid for removing particulates, grease, oil, and contaminants. E-HFO-153-10mczz may be used as a solvent in a variety of applications such as cleaning (vapor degreasing, flux removal).

[0090] In an exemplary embodiment, E-HFO-153-10mczz serves as a specialty fluid for thermal management with a slightly elevated boiling range where the product is environmentally friendly (low GWP and ODP), non-flammable, non-conductive, and has low liquid viscosity.

[0091] E-HFO-153-10mczz may be used as the working fluid for immersion cooling, which may be two-phase immersion cooling or single-phase immersion cooling.

[0092] Two-phase immersion cooling is an emerging cooling technology for the high-performance cooling market as applied to high-performance server systems. Its cooling relies on heat absorbed in the process of vaporizing the immersion cooling fluid into a gas. The fluid used in this application must meet certain requirements to be viable in use. For example, the boiling point of the fluid should be in the range of 30-75°C. In general, this range accommodates maintaining a sufficiently cool temperature for the server components while allowing the generated heat to be sufficiently dissipated to an external heat sink. Alternatively, the operating temperature of the server and immersion cooling system can be increased or decreased by using a closed system and increasing or decreasing the pressure within the system to increase or decrease the boiling point of a given fluid.

[0093] Single-phase immersion cooling has a long history in cooling computer servers. There is no phase change in single-phase immersion cooling. Instead, the liquid warms as it circulates through the computer server and / or heat exchanger, and is then pumped through the heat exchanger for cooling before returning to the server, thereby transferring heat away from the computer server. Fluids used in single-phase immersion cooling have the same requirements as in two-phase immersion cooling, except that their boiling points are typically higher than 30-75 °C to reduce evaporative losses.

[0094] In an exemplary embodiment, E-HFO-153-10mczz serves as an immersion cooling fluid with an operating temperature range close to ambient temperature. Embodiments of the present disclosure provide an immersion cooling fluid for thermal management that is environmentally friendly (i.e., has a low Global Warming Potential (GWP) and zero Ozone Depletion Potential (ODP)) compared to, for example, concepts that do not include one or more of the features disclosed herein.

[0095] In an exemplary embodiment, the submersion cooling fluid cools the heat generating components of the device by at least partially submerging the heat generating components in the submersion cooling fluid in a liquid state such that heat is transferred from the heat generating components using the submersion cooling fluid. Such devices may include, but are not limited to, high capacity energy storage devices, electrical components, mechanical components, and optical components. Suitable devices may include, but are not limited to, microprocessors, wafers used to manufacture semiconductor devices, power control semiconductors, power distribution switchgear, power transformers, circuit boards, multi-chip modules, packaged and unpackaged semiconductor devices, lasers, fuel cells, electrochemical cells, and energy storage devices such as batteries.

[0096] Opportunities for E-HFO-153-10mczz as a new working fluid exist in a variety of heat transfer applications including, but not limited to, cooling power electronics, e.g., televisions, cell phones, monitors, drones, and avionics equipment; battery thermal management in both automotive and stationary systems; powertrains for electronic vehicles; insulated gate bipolar transistors (IGBTs); electronic devices - data center servers; computer server systems; telecommunications infrastructure; 5G networks; displays; military electronics; high temperature mechanical vapor compression heat pumps (HTHP), stationary air conditioning and cooling equipment, Organic Rankine Cycles (ORC); and potentially anywhere a working fluid provides a medium to transport heat, or where there is passive evaporative cooling, such as heat pipes.

[0097] E-HFO-153-10mczz may be used in many applications for the transfer of heat, for example as a heat transfer fluid or refrigerant. In one embodiment, E-HFO-153-10mczz may be used to transfer heat from an article. The article may be in contact with a heat transfer medium comprising E-HFO-153-10mczz.

[0098] E-HFO-153-10mczz and / or Z-HFO-153-10mczz may be used in a variety of applications involving working fluids. The working fluid provides a medium for transporting heat or for generating power through mechanical means by expansion. The working fluid is typically in a liquid state in a first region. The working fluid absorbs heat in the first region, vaporizes, and travels to a second region having a lower temperature where it condenses. The working fluid is typically returned to the first region after condensation so the heat transfer cycle can be repeated. The working fluid may be used in conjunction with compression systems, expansion systems, pumps, or passive evaporative cooling such as heat pipes or thermosiphons.

[0099] In use, the working fluid in the first region is exposed to a higher (first) temperature and the working fluid is vaporized, absorbing thermal energy. The vaporized working fluid travels to a second region that is at a lower (second) temperature than the first region. The working fluid condenses in the second region, releasing thermal energy that is transported out of the system. The working fluid is then returned to the first region. The working fluid typically travels in a cyclical fashion between the first and second regions, transporting thermal energy between the first and second regions.

[0100] The working fluid is selected to undergo a phase transition from a liquid to a gaseous state over a desired operating temperature range of a system, such as, for example, a heat pipe or thermosiphon. In some embodiments, the composition of the working fluid comprises E-HFO-153-10mczz and / or Z-HFO-153-10mczz. In some embodiments, the operating temperature is at least 0° C., at least 10° C., at least 20° C., at least 30° C., at least 40° C., at least 50° C., at least 60° C., at least 70° C., at least 80° C., at least 90° C., at least 100° C., less than 125° C., less than 120° C., less than 110° C., less than 100° C., less than 90° C., less than 75° C., less than 70° C., less than 65° C., less than 60° C., less than 55° C., and combinations thereof.

[0101] The ability of a working fluid to transport heat is related to the working fluid's heat of vaporization. The greater the working fluid's heat of vaporization, the greater the amount of energy it absorbs, transports across the heat pipe during vaporization, and releases during condensation. In some embodiments, E-HFO-153-10mczz may exhibit a heat of vaporization of at least 35 kilojoules per mole (kJ / mol).

[0102] The working fluid may also be selected based at least in part on additional material properties. A working fluid having a lower viscosity will flow more easily between the two regions because the working fluid will condense and return to the first region. In some embodiments, E-HFO-153-10mczz may exhibit a lower viscosity than water at the same temperature over the operating temperature range. In some embodiments, E-HFO-153-10mczz may exhibit a viscosity of less than 0.5 centipoise at 55° C.

[0103] E-HFO-153-10mczz as a working fluid for heat transfer applications may be selected based at least in part on the surface tension exhibited by the material. For example, in heat pipe applications, a working fluid exhibiting a high surface tension may be more easily transported between hot and cold regions. In some embodiments, the selection of the wick material may increase the rate at which condensed working fluid is returned to the hot region of the heat pipe. In some embodiments, the working fluid may exhibit a lower surface tension than water at the same temperature over the operating temperature range. In some embodiments, E-HFO-153-10mczz may exhibit a surface tension of less than 64.5 dynes / cm at 70°C, less than 66.3 dynes / cm at 60°C, and / or less than 67.9 dynes / cm at 50°C.

[0104] The working fluid may also be selected based at least in part on other thermodynamic properties of the material. A working fluid that exhibits a lower specific heat and / or a lower thermal conductivity than water at the same temperature may enhance energy transport between the hot and cold regions of the heat pipe. In some embodiments, the working fluid may exhibit a specific heat of less than 4.2 J / g·K. In some embodiments, E-HFO-153-10mczz may exhibit a thermal conductivity of less than 0.6 W / m·K at 20° C.

[0105] The working fluid may also be selected to exhibit a dielectric constant suitable for electrical applications. Generally, materials exhibiting a low dielectric constant enhance the electrical insulation of electrical components immersed therein. In some embodiments, the dielectric constant of the working fluid is less than about 8 over its operating frequency range (0-20 GHz). Suitable dielectric working fluids include E-HFO-153-10mczz and have a dielectric constant of less than 7.3, less than 5.5, less than 5.0, less than 4.0, less than 3.5, less than 2.7, less than 2.5, less than 2.0, less than 1.9, less than 1.8, or less than 1.5 over the operating frequency range (0-20 GHz). Other embodiments include compounds and mixtures thereof having a dielectric constant greater than 1.0 and less than 8.0, greater than 2.0 and less than 7.3, greater than 2.5 and less than 5.5, or greater than 3.5 and less than 5.0.

[0106] Table 1 shows certain properties associated with working fluids for HFO10mczz compared to other similar compounds.

[0107] [Table 1] * Measured using ASTM D924 ** Calculated using conventional methods known in the art

[0108] Additional additives may be added to the working fluid. Suitable additives include linear hydrocarbons, linear halocarbons, cyclic hydrocarbons, cyclic halocarbons, heptafluorocyclopentane, alcohols (e.g., methanol, ethanol, isopropanol), ethers, halogenated ethers, ketones, and halogenated ketones. Examples of suitable additives include pentane (boiling point 36° C.), hexane (boiling point 69° C.), heptane (boiling point 98° C.), octane (boiling point 125° C.), cyclopentane (boiling point 49° C.), cyclohexane (boiling point 80° C.), cycloheptane (boiling point 118° C.), methylcyclobutane (boiling point 39° C.), methylcyclopentane (boiling point 72° C.), diethyl ether (boiling point 35° C.), diisopropyl ether (boiling point 69° C.), C 4 F 9OCH 3 (CAS163702-07-6), C 4 F 9 OCH 2 CH 3 (CAS163702-05-4), iC 4 F 9 OCH 2 CH 3 (CAS163702-06-5), (CF 3 ) 2 CFCF(OCH 3 )CF 2 CF 3 (73DE, CAS132182-92-4), C 3 F 7 OCH 3 (CAS375-03-1), (CF 3 ) 2 CFCF(OCH 2 CH 3 )CF 2 CF 2 CF 3 (HFE7500, CAS 297730-93-9), 1,1,1,2,3,3-hexafluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)pentane (HFE7600, CAS 870778-34-0), furan,2,3,3,4,4-pentafluorotetrahydro-5-methoxy-2,5-bis[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-(HFE7700), [CAS 812-05-4], and 1,1,1,2,4,4,5,5,5-nonafluoro-(2-trifluoromethyl)-3-pentanone (Novec1230, CAS 756-13-8). EXAMPLES

[0109] An illustrative example of a method for forming HFO-153-10mczz is provided below.

[0110] Example 1 Coupling of HCFC-225ca and copper in DMF 100 g (0.49 mol) of 3,3-dichloro-1,1,1,2,2-pentafluoropropane (HCFC-225ca), 8 g (1.28 mol) of pure metallic copper (Cu) powder, 6 g (0.013 mol) of 2,2-bipyridine, and 200 g of dimethylformamide (DMF) were charged to a 400 mL Hastelloy® C shaker tube. The starting HCFC-225ca contained about 2.2% HCFC-225cb. The reactor was cooled to 0° C. and then evacuated. The reaction mixture was then heated to 90° C. with stirring and stirred at 90° C. for 4 hours. The reactor pressure rose to 21 psig at 90° C. The pressure then dropped to −5 psig after the reactor was cooled to room temperature.

[0111] [ka]

[0112] The liquid phase of the reaction was analyzed by GC-FID-MS. The data are reported in area percent by gas chromatography flame ionization detection (GC-FID) in Table 2. The selectivity to E-HFO-153-10mczz was approximately 85%.

[0113] [Table 2]

[0114] Example 2 Chlorination of HCFC-225ca / HCFC-225cb mixtures to CFC-215ca / CFC-215cb An Inconel 600 tube with dimensions of 15 inches long by 0.5 inches outside diameter (OD) and 0.43 inches inside diameter (ID) was set up as the reactor. After purging with N2 to remove air from the reactor, 3,3-dichloro-1,1,1,2,2-pentafluoropropane (HCFC-225ca) and 1,3-dichloro-1,1,2,2,3-pentafluoropropane (HCFC-225cb) and N 2 and Cl 2The mixture of gases was fed to the reactor under the conditions shown in Table 3. The reactor effluent was analyzed by online GC-MS-FID. The reaction did not contain a catalyst.

[0115] [ka]

[0116] As shown in Table 3, HCFC-225ca and HCFC-225cb were efficiently chlorinated to 1,1,1-trichloropentafluoropropane (CFC-215cb) and 1,1,3-trichloropentafluoropropane (CFC-215ca), respectively, without a catalyst.

[0117] [Table 3]

[0118] Example 4 Chlorination of HFC-245cb to HCFC-225ca and CFC-215cb An Inconel 600 tube with dimensions of 15 inches long by 0.5 inches outer diameter and 0.43 inches inner diameter was set up as the reactor. N 2 After purging, 1,1,1,2,2-pentafluoropropane (HCFC-245cb) and Cl 2 The mixture of gases was discharged to the reactor at atmospheric pressure and under the conditions shown in Table 4 for the chlorination reaction. The reactor effluent was analyzed by online GC-MS-FID. The reaction did not contain any catalyst.

[0119] [ka]

[0120] [Table 4]

[0121] As shown in Table 5, HFC-245cb was efficiently chlorinated to 3,3-dichloro-1,1,1,2,2-pentafluoropropane (HCFC-225ca) and 1,1,1-trichloropentafluoropropane (CFC-215cb) without a catalyst.

[0122] [Table 5]

[0123] Example 5 Coupling of CFC-215cb with Ru / SiC catalyst 10 mL of 2% Ru / SiC catalyst pellets were placed in a Monel 400 reactor with a length of 12 inches and an outer diameter of ½ inch. N was used to remove air from the reactor. 2 After purging, the catalyst was 2 The mixture was activated with CFC-215cb and H 2 at a temperature of 130°C, a pressure of 150 psi, an organic flow rate of 3.57 cc / hr, and 30.4 standard cubic centimeters per minute (sccm) of N 2 flow rate, and 30.4 sccm H 2 The flow rate was fed to the reactor.

[0124] [ka]

[0125] The reactor effluent was analyzed by online GC-MS-FID. As shown in Tables 6 and 7, CFC-215cb reached high conversion and HFO-151-10mcxx was produced with high selectivity.

[0126] [Table 6]

[0127] [Table 7]

[0128] Example 6 Hydrodechlorination of CFO-151-10mcxx using 56% Ni catalyst 10 mL of 56% nickel-containing 1 / 8" tablet catalyst (BASFE474TR, BASF, Ludwigshafen, Germany) was placed in a Monel 400 reactor with a length of 12 inches and an outer diameter of 1 / 2 inch. N was used to remove air from the reactor. 2 After purging, the catalyst is 2 The mixture was activated with CFO-151-10mcxx and H 2 The temperature was 250°C, the pressure was 150 psi, the organic flow rate was 0.75 cc / hr, and the N 2 Flow rate, and H of 25.1 sccm 2 The flow rate was fed to the reactor.

[0129] [ka]

[0130] The reactor effluent was analyzed by online GC-MS-FID. As shown in Tables 8 and 9 below, CFO-151-10mcxx reached high conversion and HFO-153-10mczz was produced with good selectivity.

[0131] [Table 8]

[0132] [Table 9]

[0133] Example 7 Hydrodechlorination of CFO-151-10mcxx using 1% Ir / C catalyst 10 mL of 1% Ir / C catalyst was placed in a Monel 400 reactor with a length of 12 inches and an outer diameter of ½ inch. N 2 After purging, the catalyst is2 The mixture was activated with CFO-151-10mcxx and H 2 At a pressure of 150 psi, an organic flow rate of 0.86 cc / hr, and 17.9 sccm H 2 The reactor was fed at the flow rates and temperatures shown in Table 11.

[0134] [ka]

[0135] The reactor effluent was analyzed by online GC-MS-FID. As shown in Tables 10 and 11, CFO-151-10mcxx reached high conversion and HFO-153-10mczz was produced. PFH in Table 10 is perfluorohexyne.

[0136] [Table 10]

[0137] [Table 11]

[0138] Example 8 Hydrodechlorination of CFO-151-10mcxx using bimetallic catalysts Six milliliters of bimetallic catalyst on a solid carbon support was placed in a Monel 400 reactor with a length of 12 inches and an outer diameter of ½ inch. N was used to remove air from the reactor. 2 After purging, the catalyst was 2 The mixture was activated with CFO-151-10mcxx and H 2 At a pressure of 150 psi, an organic flow rate of 3.20 cc / hr, and 25.0 sccm H 2 Flow rate, and temperature and N 2 The flow rate was fed to the reactor.

[0139] [ka]

[0140] The reactor effluent was analyzed by online GC-MS-FID. As shown in Tables 12 and 13, CFO-151-10mcxx reached high conversion and HFO-153-10mczz was produced with high selectivity.

[0141] [Table 12]

[0142] [Table 13]

[0143] FIG. 1 shows a system 100 having at least a first loop 112 and an optional second loop 116. 2 F 5 CF=CFC 2 F 5 (E-HFO-151-12mcyy), EC 2 F 5 CH=CHC 2 F 5 (E-HFO-153-10mczz), C 3 F 7 CH=CHCF 3 (HFO-153-10mzz), (CF 3 ) 2 CFCH=CHCF 3 (HFO-153-10mzzy), ZC 2 F 5 CF=CFC 2 F 5 (z-FO-151-12mcyZ) or EC 2 F 5 CF=CFC 2 F 5 (E-HFO-151-12mcyy), EC 2 F 5 CH=CHC 2 F 5 (E-HFO-153-10mczz), C 3F 7 CH=CHCF 3 (HFO-153-10mzz), (CF 3 ) 2 CFCH=CHCF 3 (HFO-153-10mzzy), ZC 2 F 5 CF=CFC 2 F 5 A source 101 of (z-FO-151-12mcyZ) can be utilized to charge the loop system 112 or to replenish or replace existing refrigerant in the loop system 11. The loop system 112 generally includes at least one exchanger 110, a pressure regulator 104, at least one exchanger 106, a compressor 108, and a charge valve 102, which may be arranged in series as shown.

[0144] 1 also shows an optional second loop 116 with a third exchanger that exchanges thermal energy between loops 112 and 116. A prime mover 126 (compressor, pump, etc.) drives the EC 2 F 5 CF=CFC 2 F 5 (E-HFO-151-12mcyy), EC 2 F 5 CH=CHC 2 F 5 (E-HFO-153-10mczz), C 3 F 7 CH=CHCF 3 (HFO-153-10mzz), (CF 3 ) 2 CFCH=CHCF 3 (HFO-153-10mzzy), ZC 2 F 5 CF=CFC 2 F 5(z-FO-151-12mcyZ), or blends thereof, are circulated to various electrical components, such as batteries, electric motors, computer components, etc., that require thermal management to regulate temperature. Thermal energy from one or more of components 118, 120, 122, and 124 is used to exchange heat with the working fluid and may be used to heat other fluids, such as air, water, or other fluids. Valves (not shown) are included in all flow paths to aid in thermal management, as well as thermal energy exchangers upstream or downstream of components 118, 120, 122, and 124. Four components requiring thermal management are shown, but fewer or more components may be included.

[0145] 2 illustrates an exemplary immersion cooling embodiment 200 that includes a two-phase tank 202, one or more condenser units, a pump 206, a liquid cooling unit, a condenser return line 210 and a cooling fluid supply line 212, as well as an immersion fluid 214 and electrical components 216. The immersion fluid is an EC 2 F 5 CF=CFC 2 F 5 (E-HFO-151-12mcyy), EC 2 F 5 CH=CHC 2 F 5 (E-HFO-153-10mczz), C 3 F 7 CH=CHCF 3 (HFO-153-10mzz), (CF 3 ) 2 CFCH=CHCF 3 (HFO-153-10mzzy), ZC 2 F 5 CF=CFC 2 F 5 (z-FO-151-12mcyZ) or EC 2 F 5 CF=CFC 2 F 5 (E-HFO-151-12mcyy), EC 2 F 5 CH=CHC 2 F 5(E-HFO-153-10mczz), C 3 F 7 CH=CHCF 3 (HFO-153-10mzz), (CF 3 ) 2 CFCH=CHCF 3 (HFO-153-10mzzy), ZC 2 F 5 CF=CFC 2 F 5 (z-FO-151-12mcyZ).

[0146] The thermal regulating fluids described herein are 2 F 5 CF=CFC 2 F 5 (E-HFO-151-12mcyy), EC 2 F 5 CH=CHC 2 F 5 (E-HFO-153-10mczz), C 3 F 7 CH=CHCF 3 (HFO-153-10mczz), (CF 3 ) 2 CFCH=CHCF 3 (HFO-153-10mzzy), ZC 2 F 5 CF=CFC 2 F 5 (z-FO-151-12mcyZ) or EC 2 F 5 CF=CFC 2 F 5 (E-HFO-151-12mcyy), EC 2 F 5 CH=CHC 2 F 5 (E-HFO-153-10mczz), C 3 F 7 CH=CHCF 3 (HFO-153-10mczz), (CF 3 ) 2 CFCH=CHCF 3(HFO-153-10mzzy), ZC 2 F 5 CF=CFC 2 F 5 (z-FO-151-12mcyZ).

[0147] In use, the thermal conditioning medium is a fluoroolefin EC 60 ... 2 F 5 CF=CFC 2 F 5 (E-HFO-151-12mcyy), EC 2 F 5 CH=CHC 2 F 5 (E-HFO-153-10mczz), C 3 F 7 CH=CHCF 3 (HFO-153-10mzz), (CF 3 ) 2 CFCH=CHCF 3 (HFO-153-10mzzy), ZC 2 F 5 CF=CFC 2 F 5 (z-FO-151-12mcyZ), or a blend thereof. The method or system further includes at least one motive force for circulating a thermal conditioning fluid, whether in the first and / or second loop, to manage the thermal condition of at least one of said electrical components.

[0148] In certain embodiments, thermal energy is exchanged between the working fluid and an electrical component by contacting the electrical component selected from one of: televisions, cell phones, monitors, drones, and avionics devices; batteries, powertrains for electric vehicles, insulated gate bipolar transistors (IGBTs), electronic devices - data center servers, computer server systems, telecommunications infrastructure, 5G networks; displays, and military electronics, and the working fluid is connected to an EC 2 F 5 CF=CFC 2 F 5 (E-HFO-151-12mcyy), EC 2 F 5 CH=CHC 2 F 5 (E-HFO-153-10mczz), C 3 F 7 CH=CHCF 3 (HFO-153-10mzz), (CF 3 ) 2 CFCH=CHCF 3 (HFO-153-10mzzy), ZC 2 F 5 CF=CFC 2 F 5 (z-FO-151-12mcyZ), and at least one of the fluoroolefins is included to regulate the thermal condition of at least one component.

[0149] In certain embodiments, the thermal energy of a working fluid in a system selected from one of a high temperature mechanical vapor compression heat pump (HTHP), a stationary air conditioning and refrigeration system, and an organic Rankine cycle (ORC) is utilized to generate an EC 2 F 5 CF=CFC 2 F 5 (E-HFO-151-12mcyy), EC 2 F 5 CH=CHC 2 F 5 (E-HFO-153-10mczz), C 3 F 7 CH=CHCF 3 (HFO-153-10mzz), (CF3 ) 2 CFCH=CHCF 3 (HFO-153-10mzzy), ZC 2 F 5 CF=CFC 2 F 5 A working fluid comprising at least one of the fluoroolefins including (z-FO-151-12mcyZ) is contacted with the system and components of the system to thermally regulate the thermal condition of the system.

[0150] The system further includes at least one heat exchange component for exchanging heat between the thermal conditioning fluid and a device for circulating one of air, water, a glycol-based fluid such as ethylene glycol or propylene glycol, or other fluids.

[0151] The present system and method regulates the exchange of thermal energy between a thermal conditioning medium and at least one electrical component requiring thermal management from one of a hybrid electric vehicle (HEV), a mild hybrid electric vehicle (MHEV), a plug-in hybrid electric vehicle (PHEV), or an electric vehicle (EV) by circulating a thermal conditioning fluid in direct / indirect thermal contact with the at least one electrical component, the thermal conditioning fluid being in accordance with an EC 2 F 5 CF=CFC 2 F 5 (E-HFO-151-12mcyy), EC 2 F 5 CH=CHC 2 F 5 (E-HFO-153-10mczz), C 3 F 7 CH=CHCF 3 (HFO-153-10mzz), (CF 3 ) 2 CFCH=CHCF 3 (HFO-153-10mzzy), ZC 2 F 5 CF=CFC 2 F 5(z-FO-151-12mcyZ), or blends thereof.

[0152] Other embodiments Transferring thermal energy between a working fluid and an electrical component, comprising: an electrical component selected from one of: televisions, mobile phones, monitors, drones, and avionics devices; batteries, powertrains for electric vehicles, insulated gate bipolar transistors (IGBTs), electronic devices - data center servers, computer server systems, telecommunications infrastructure, 5G networks; displays, and military electronics; or and an electrical component selected from one of a high temperature mechanical vapor compression heat pump (HTHP), a stationary air conditioning and cooling system, and an organic Rankine cycle (ORC). EC 2 F 5 CF=CFC 2 F 5 (E-HFO-151-12mcyy), EC 2 F 5 CH=CHC 2 F 5 (E-HFO-153-10mczz), C 3 F 7 CH=CHCF 3 (HFO-153-10mzz), (CF 3 ) 2 CFCH=CHCF 3 (HFO-153-10mzzy), ZC 2 F 5 CF=CFC 2 F 5 (z-FO-151-12mcyZ), and thermally adjusting the thermal condition of the at least one component.

[0153] 1. A system for transferring thermal energy between a working fluid and an electrical component, comprising: Televisions, mobile phones, monitors, drones, and avionics devices; batteries, powertrains for electric vehicles, insulated gate bipolar transistors (IGBTs), electronic devices - data center servers, computer server systems, telecommunications infrastructure, 5G networks; displays, and military electronics; or A component containing one of the following: a high temperature mechanical vapor compression heat pump (HTHP), a stationary air conditioning and cooling system, and an organic Rankine cycle (ORC), EC in energy exchange contact with the part 2 F 5 CF=CFC 2 F 5 (E-HFO-151-12mcyy), EC 2 F 5 CH=CHC 2 F 5 ,(E-HFO-153-10mczz),C 3 F 7 CH=CHCF 3 (HFO-153-10mzz), (CF 3 ) 2 CFCH=CHCF 3 (HFO-153-10mzzy), ZC 2 F 5 CF=CFC 2 F 5 The thermal condition of the one component is thermally adjusted by contacting it with a working fluid circulating fluid containing at least one of the fluoroolefins including (z-FO-151-12mcyZ).

[0154] A system for transferring thermal energy between a working fluid and an electrical component, comprising: 2 F 5 CF=CFC 2 F 5 (E-HFO-151-12mcyy), EC 2 F 5 CH=CHC 2 F 5 (E-HFO-153-10mczz), C 3 F 7 CH=CHCF 3(HFO-153-10mzz), (CF 3 ) 2 CFCH=CHCF 3 (HFO-153-10mzzy), ZC 2 F 5 CF=CFC 2 F 5 (z-FO-151-12mcyZ), a motive force for circulating the working fluid, a control valve for directing the working fluid to one or more electrical components and collecting the working fluid from the one or more electrical components, and components for exchanging and recovering energy from the working fluid.

[0155] A method for transferring thermal energy between a working fluid and an electrical component, the electrical component comprising: 2 F 5 CF=CFC 2 F 5 (E-HFO-151-12mcyy), EC 2 F 5 CH=CHC 2 F 5 (E-HFO-153-10mczz), C 3 F 7 CH=CHCF 3 (HFO-153-10mzz), (CF 3 ) 2 CFCH=CHCF 3 (HFO-153-10mzzy), ZC 2 F 5 CF=CFC 2 F 5 (z-FO-151-12mcyZ), a motive force for circulating the working fluid, directing the working fluid into contact with one or more electrical components, and collecting the working fluid from the one or more electrical components, and a motive force for recovering energy from the working fluid.

[0156] EC 2 F 5 CF=CFC 2 F5 (E-HFO-151-12mcyy), EC 2 F 5 CH=CHC 2 F 5 (E-HFO-153-10mczz), C 3 F 7 CH=CHCF 3 (HFO-153-10mzz), (CF 3 ) 2 CFCH=CHCF 3 (HFO-153-10mzzy), ZC 2 F 5 CF=CFC 2 F 5 A method of transferring thermal energy between at least one of fluoroolefins including (z-FO-151-12mcyZ) and an electrical component by immersion using the system of FIG.

[0157] 2. A method or system for transferring thermal energy by immersion by selecting a working fluid exhibiting a dielectric constant suitable for electrical applications and exhibiting a low dielectric constant to enhance electrical insulation of the electrical component, and immersing the electrical component in at least one of fluoroolefins including E-C2F5CF=CFC2F5 (E-HFO-151-12mcyy), E-C2F5CH=CHC2F5 (E-HFO-153-10mczz), C3F7CH=CHCF3 (HFO-153-10mzz), (CF3)2CFCH=CHCF3 (HFO-153-10mzzy), Z-C2F5CF=CFC2F5 (Z-FO-151-12mcyZ).

[0158] A method or system for transferring thermal energy by immersing an electrical component in a tank containing a dielectric immersion fluid comprising at least E-HFO-153-10mczz.

[0159] 1. A method or system for transferring thermal energy by immersing an electrical component in a tank containing a dielectric immersion fluid that includes at least E-HFO-153-10mczz and has a dielectric constant of less than 7.3, less than 5.5, less than 5.0, less than 4.0, less than 3.5, less than 2.7, less than 2.5, less than 2.0, less than 1.9, less than 1.8, or less than 1.5 over the operating frequency range (0-20 GHz).

[0160] At least the systems of

[0138] to

[0140] further comprise a tank for holding the immersion fluid and a closed loop circuit for circulating a medium for controlling the temperature of the heated immersion fluid.

[0161] Although the present 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 and equivalents can be substituted for elements thereof without departing from the scope of the invention. In addition, many modifications can be made to adapt a particular situation or material to the teachings of the invention without departing from the essential scope of the invention. Therefore, it is not intended that the invention be limited to the particular embodiment disclosed as the best mode contemplated for carrying out this invention, but the invention is intended to include all embodiments falling within the scope of the appended claims. In addition, all numerical values ​​specified in the detailed description should be interpreted as if both exact and approximate values ​​were explicitly specified.

Claims

1. A method for producing a fluoroolefin, comprising coupling 3,3-dichloro-1,1,1,2,2-pentafluoropropane in the liquid phase in the presence of a catalyst to form a composition comprising 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene.

2. The method of claim 1 , wherein the coupling step is carried out in an aprotic solvent.

3. 3. The method of claim 2, wherein the aprotic solvent is selected from the group consisting of dimethylformamide, dimethylacetamide, dimethylsulfoxide, and N-methylpyrrolidone.

4. 10. The method of claim 1, wherein the catalyst is selected from the group consisting of 2,2-bipyridine, copper (I) salts, and combinations thereof.

5. 5. The method of claim 4, wherein the copper(I) salt is selected from the group consisting of CuCl, CuBr, CuI, and copper(I) acetate.

6. 10. The method of claim 1, wherein the coupling step is carried out in the presence of copper powder.

7. A method for producing a fluoroolefin, comprising coupling 1,1,1-trichloropentafluoropropane in the vapor phase in the presence of a first catalyst to form a composition comprising 3,4-dichloro-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene.

8. The method of claim 7 , wherein the first catalyst comprises Ru / SiC.

9. In the gas phase, in the presence of a second catalyst, hydrogen (H 2 ) to hydrodechlorinate the 3,4-dichloro-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene, resulting in 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (CF 3 CF 2 CH=CHCF 2 CF 3 ) and 3-chloro-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (CF 3 CF 2 CCl=CHCF 2 CF 3 8. The method of claim 7, further comprising forming a composition comprising:

10. 10. The method of claim 9, wherein the second catalyst comprises a nickel-containing catalyst, an iridium / carbon catalyst, or a bimetallic catalyst on a carbon support.

11. 11. The method of claim 10, further comprising hydrodechlorinating the 3-chloro-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene with hydrogen in the vapor phase in the presence of a third catalyst to form 1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene.

12. 12. The method of claim 11, wherein the third catalyst is selected from the group consisting of a nickel-containing catalyst, an iridium / carbon catalyst, a bimetallic catalyst on a carbon support, a gold catalyst on a support, a platinum catalyst on a support, a palladium catalyst on a support, a copper catalyst on a support, and combinations thereof.

13. 10. A composition formed by the method of claim 1.

14. 8. A composition formed by the method of claim 7.

15. 10. A composition formed by the method of claim 9.

16. 12. A composition formed by the method of claim 11.

17. 1. A method for transferring thermal energy, comprising: providing at least one electrical component requiring thermal management from one of a hybrid electric vehicle (HEV), a mild hybrid electric vehicle (MHEV), a plug-in hybrid electric vehicle (PHEV), or an electric vehicle (EV); and circulating a thermal conditioning fluid in direct / indirect thermal contact with the at least one electrical component, wherein the thermal conditioning fluid is an E-C 2 F 5 CF = CFC 2 F 5 , E.-C. 2 F 5 CH=CHC 2 F 5 , C 3 F 7 CH=CHCF 3 , (CF 3 ) 2 CFCH=CHCF 3 , Z.C. 2 F 5 CF = CFC 2 F 5 and thermally modulating the thermal condition of said at least one component by at least one fluoroolefin comprising:

18. 1. A method for transferring thermal energy between a working fluid and an electrical component, comprising: a) televisions, mobile phones, monitors, drones, and avionics devices; batteries, powertrains for electric vehicles, insulated gate bipolar transistors (IGBTs), electronic devices - data center servers, computer server systems, telecommunications infrastructure, 5G networks; displays, and military electronics; or b) High temperature mechanical vapor compression heat pumps (HTHPs), stationary air conditioning and refrigeration units, and organic Rankine cycles (ORCs); The electrical component selected from one of E-C 2 F 5 CF = CFC 2 F 5 , E.-C. 2 F 5 CH=CHC 2 F 5 , C 3 F 7 CH=CHCF 3 , (CF 3 ) 2 CFCH=CHCF 3 , Z.C. 2 F 5 CF = CFC 2 F 5 and thermally conditioning the thermal condition of the at least one component.

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