Synthesis of (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene

Abstract

The present application relates to a process for preparing (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene.

Description

[Technical Field]

[0001] This application relates to a process for preparing (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene. [Background technology]

[0002] Growing public awareness of the environmental impact of fossil fuel extraction, transportation, and use is creating a new driving force for environmental conservation, in the form of regulating and reducing emissions of CO2 equivalents into the atmosphere. New working fluids with low global warming potential (GWP) and ozone depletion potential (ODP) for both existing and new applications in the temperature control segment must comply with these new regulations. [Overview of the project] [Means for solving the problem]

[0003] This application provides, in particular, a process for preparing (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, which includes reacting hexafluoropropa-1-ene with 1,3,3,3-tetrafluoropropa-1-ene in the presence of an acid catalyst.

[0004] This application further provides a process for preparing (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, which includes fluorinating 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane in the presence of a catalyst.

[0005] This application further states, (i)(E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, (ii) One or more compounds selected from the following: (Z)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2ene, Hexafluoropropa-1-ene, and 1,3,3,3-tetrafluoropropane-1-ene The present invention provides a composition containing the following:

[0006] This application further states, (i)(E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, (ii) One or more compounds selected from the following: 1,1,1,4,5,5,5-heptafluoro-2-(trifluoromethyl)penta-2-ene, (E)-4-chloro-1,1,1,5,5,5-hexafluoro-4-(trifluoromethyl)penta-2-ene, and 1,1,1,5,5,5-Hexafluoro-2-(trifluoromethyl)penta-2,3-diene The present invention provides a composition containing the following:

[0007] This application further states, (i) 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane, (ii) One or more compounds selected from 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane and 3,3,3-trifluoropropane-1-ene, The present invention provides a composition containing the following:

[0008] In some embodiments, the compositions provided herein are prepared according to one or more of the processes described herein.

[0009] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as those commonly understood by those skilled in the art to which the present invention pertains. Methods and materials for use in the present invention are described herein, and other suitable methods and materials known in the art may also be used. Materials, methods, and examples are illustrative and not intended to limit the scope. All publications, patent applications, patents, sequences, database entries, and other references referenced herein are incorporated herein by reference in their entirety. In the event of any conflict, including definitions, this specification shall prevail. [Modes for carrying out the invention]

[0010] Hydrofluoroolefins (HFOs) can be useful in a variety of applications, including but not limited to foaming, heat transfer, refrigeration, cleaning, and solvent applications. Among the recently developed HFOs, (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene (i.e., F13iE or HFO-153-10mzzt) can be useful in heat transfer fluid applications (e.g., for use in electric vehicle batteries). Therefore, this application provides a novel process for preparing (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene.

[0011] Definitions and Abbreviations When used herein, the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having,” or any other variations thereof are intended to encompass non-exclusive inclusion. For example, a process, method, article, or apparatus that includes a list of elements is not necessarily limited to those elements alone, and may include other elements not expressly described for or specific to such process, method, article, or apparatus. Furthermore, unless expressly stated otherwise, “or” means an inclusive “or” and not an exclusive “or.” For example, condition A or B is satisfied by any one of the following: A is true (or exists) and B is false (or does not exist); A is false (or does not exist) and B is true (or exists); and both A and B are true (or exist).

[0012] As used herein, the term “consists essentially of” is used to define compositions and methods that include materials, processes, features, components, or elements in addition to those literally disclosed, provided that these additionally included materials, processes, features, components, or elements do not substantially affect the fundamental and novel features of the claimed invention, in particular the mechanism of operation for achieving any of the desired results of the processes of the present invention. The terms “consists essentially of” or “consisting essentially of” take an intermediate position between “includes” and “consists of.”

[0013] Furthermore, the use of "a" or "an" is used to describe the elements and components described herein. This is done solely for convenience and to give a general sense of the scope of the invention. This description should be interpreted as including one or at least one, and the singular form also includes the plural form unless it is evident that it has a different meaning.

[0014] As used herein, the term "about" means to account for variations due to experimental error (e.g., about plus or minus 10% of the indicated value). All measured values reported herein are understood to be modified by the term "about" whether or not the term "about" is explicitly used, unless otherwise specified.

[0015] As used herein, the term "alkyl" alone or in combination includes cyclic or acyclic and straight-chain or branched alkyl groups such as methyl, ethyl, n-propyl, i-propyl, or various isomers thereof. For example, an alkyl group may contain from 1 to 10 carbon atoms. The alkyl group may be a lower alkyl containing from 1 to 6 carbon atoms.

[0016] As used in the present invention, the term "catalyst" means a substance that accelerates a chemical reaction but is not consumed by the reaction, and thus can be recovered without chemically changing at the end of the reaction.

[0017] When a quantity, concentration, or other value or parameter is given as any one of a range, a preferred range, or a list of preferred upper and / or lower values, these are to be understood as specifically disclosing all ranges formed from any pair of any range upper limit or preferred upper value and any range lower limit or preferred lower value, regardless of whether or not the ranges are separately disclosed. When a numerical range is recited herein, unless otherwise indicated, this range is intended to include its endpoints and all integers and fractions within the range.

[0018] The following abbreviations can be used herein. F13iE or HFO-153-10mzzt: (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene HCFO: hydrochlorofluorolefin HCFO-153-10mzzx:(E)-4-chloro-1,1,1,5,5,5-hexafluoro-4-(trifluoromethyl)penta-2-ene HFC: Hydrofluorocarbon HCFC-216aa:2,2-Dichloro-1,1,1,3,3,3-Hexafluoropropane HFC-549mdfx: 2,4-Dichloro-1,1,1,5,5,5-Hexafluoro-2-(trifluoromethyl)pentane HFO: Hydrofluoroolefin HFO-1234ze:1,3,3,3-tetrafluoropropane-1-ene HFO-1529mztt:1,1,1,5,5,5-Hexafluoro-2-(trifluoromethyl)penta-2,3-diene HFO-153-10mezt:1,1,1,4,5,5,5-heptafluoro-2-(trifluoromethyl)penta-2-ene HFP: Hexafluoropropene TFP:3,3,3-trifluoropropane-1-ene

[0019] The process of the present invention This application provides a process for preparing (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, comprising reacting hexafluoropropa-1-ene with 1,3,3,3-tetrafluoropropa-1-ene in the presence of an acid catalyst.

[0020] In some embodiments, the acid catalyst is a Lewis acid catalyst. As used herein, the term “Lewis acid catalyst” compound (e.g., metallic compounds) acts as an electron pair acceptor to enhance the reactivity of a substrate. Exemplary Lewis acid catalysts include, but are not limited to, transition metal Lewis acid catalysts (e.g., titanium, zinc, iron, copper, and zinc-based Lewis acid catalysts) and main group Lewis acid catalysts (e.g., aluminum, boron, silicon, tin, and antimony Lewis acid catalysts). In some embodiments, the acid catalyst is a strong Lewis acid catalyst. Additional examples of Lewis acid catalysts can be found, for example, in International Publication Nos. 2008 / 057513 and 2018 / 022500, the respective disclosures of which are incorporated herein by reference in their entirety.

[0021] In some embodiments, the acid catalyst is selected from SbF5, aluminum chlorofluoride (ACF), and aluminum chloride. In some embodiments, the acid catalyst is SbF5.

[0022] In some embodiments, the reaction between hexafluoropropa-1-ene and 1,3,3,3-tetrafluoropropa-1-ene takes place at temperatures ranging from approximately -30°C to approximately 100°C, for example, approximately -30°C to approximately 75°C, approximately -30°C to approximately 50°C, approximately -30°C to approximately 25°C, approximately -30°C to approximately 10°C, approximately -30°C to approximately 0°C, approximately 0°C to approximately 100°C, and approximately 0°C to approximately 75°C. The reaction is carried out at temperatures of approximately 0°C to 50°C, approximately 0°C to 25°C, approximately 0°C to 10°C, approximately 10°C to 100°C, approximately 10°C to 75°C, approximately 10°C to 50°C, approximately 10°C to 25°C, approximately 25°C to 100°C, approximately 25°C to 75°C, approximately 25°C to 50°C, approximately 50°C to 100°C, approximately 50°C to 75°C, or approximately 75°C to 100°C. In some embodiments, the reaction between hexafluoropropa-1-ene and 1,3,3,3-tetrafluoropropa-1-ene is carried out at temperatures of approximately 25°C to 75°C. In some embodiments, the reaction between hexafluoropropa-1-ene and 1,3,3,3-tetrafluoropropa-1-ene is carried out at temperatures of approximately 40°C to 60°C.

[0023] In some embodiments, the reaction between hexafluoropropa-1-ene and 1,3,3,3-tetrafluoropropa-1-ene is carried out at a pressure of about 1 atm to about 25 atm, for example, about 1 atm to about 20 atm, about 1 atm to about 15 atm, about 1 atm to about 10 atm, about 1 atm to about 5 atm, about 5 atm to about 25 atm, about 5 atm to about 20 atm, about 5 atm to about 15 atm, about 5 atm to about 10 atm, about 10 atm to about 25 atm, about 10 atm to about 20 atm, about 10 atm to about 15 atm, about 15 atm to about 25 atm, about 15 atm to about 20 atm, or about 20 atm to about 25 atm.

[0024] In some embodiments, the reaction between hexafluoropropa-1-ene and 1,3,3,3-tetrafluoropropa-1-ene is carried out as a liquid-phase reaction. In some embodiments, the reaction between hexafluoropropa-1-ene and 1,3,3,3-tetrafluoropropa-1-ene is carried out in the absence of additional solvent components.

[0025] In some embodiments, the process for preparing (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene includes premixing hexafluoropropa-1-ene with an acid catalyst to form a first mixture. In some embodiments, the premixing of hexafluoropropa-1-ene with the acid catalyst to form the first mixture is carried out before reacting with 1,3,3,3-tetrafluoropropa-1-ene. In some embodiments, the mixing of hexafluoropropa-1-ene with the acid catalyst is carried out in a liquid phase. In some embodiments, the first mixture is a liquid.

[0026] In some embodiments, the premixing of hexafluoropropa-1-ene and the acid catalyst is carried out at a pressure of about 1 atm to about 25 atm, for example, about 1 atm to about 20 atm, about 1 atm to about 15 atm, about 1 atm to about 10 atm, about 1 atm to about 5 atm, about 5 atm to about 25 atm, about 5 atm to about 20 atm, about 5 atm to about 15 atm, about 5 atm to about 10 atm, about 10 atm to about 25 atm, about 10 atm to about 20 atm, about 10 atm to about 15 atm, about 15 atm to about 25 atm, about 15 atm to about 20 atm, or about 20 atm to about 25 atm.

[0027] In some embodiments, the process includes adding 1,3,3,3-tetrafluoropropane-1-ene to a first mixture, thereby forming (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene.

[0028] In some embodiments, the present application relates to a process for preparing (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, (i) Premixing hexafluoropropane-1-ene and SbF5 to form a first mixture, (ii) Reacting 1,3,3,3-tetrafluoropropane-1-ene with the first mixture to form (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, It provides a process that includes this.

[0029] This application further provides a process for preparing (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, which includes fluorinating 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane in the presence of a catalyst.

[0030] In some embodiments, fluorination involves reacting 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane in the presence of a fluorinating agent.

[0031] In some embodiments, one molar equivalent of fluorinating agent or an excess of fluorinating agent is used based on one equivalent of 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane. In some embodiments, one molar equivalent of fluorinating agent is used based on one equivalent of 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane. In some embodiments, a molar excess of fluorinating agent is used based on one equivalent of 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane.

[0032] In some embodiments, about 1 to about 25 molar equivalents of fluorinating agent are used based on 1 equivalent of 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane, for example, about 1 to about 20, about 1 to about 15, about 1 to about 10, about 1 to about 5, about 1 to about 2, about 2 to about 25, about 2 to about 20, about 2 to about 15, about 2 to about 10, about 2 to about 5, about 5 to about 25, about 5 to about 20, about 5 to about 15, about 5 to about 10, about 10 to about 25, about 10 to about 20, about 10 to about 15, about 15 to about 25, about 15 to about 20, or about 20 to about 25 molar equivalents of fluorinating agent. In some embodiments, about 6 to about 25 molar equivalents of a fluorinating agent are used based on 1 equivalent of 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane.

[0033] In some embodiments, the fluorinating agent is selected from hydrogen fluoride, antimony trifluoride, antimony tetrafluoride, antimony pentafluoride, antimony trichloride / hydrogen fluoride, antimony tetrachloride / hydrogen fluoride, or any mixture thereof. In some embodiments, the fluorinating agent is hydrogen fluoride.

[0034] In some embodiments, fluorination is carried out as liquid-phase fluorination.

[0035] In some embodiments, liquid-phase fluorination is carried out at temperatures of approximately 50°C to approximately 150°C, for example, approximately 50°C to approximately 125°C, approximately 50°C to approximately 100°C, approximately 50°C to approximately 75°C, approximately 75°C to approximately 150°C, approximately 75°C to approximately 125°C, approximately 75°C to approximately 100°C, approximately 100°C to approximately 150°C, approximately 100°C to approximately 125°C, or approximately 125°C to approximately 150°C.

[0036] In some embodiments, liquid-phase fluorination is performed at approximately 0 psig to approximately 600 psig, for example, approximately 0 psig to approximately 500 psig, approximately 0 psig to approximately 400 psig, approximately 0 psig to approximately 300 psig, approximately 0 psig to approximately 200 psig, approximately 0 psig to approximately 100 psig, approximately 0 psig to approximately 50 psig, approximately 50 psig to approximately 600 psig, approximately 50 psig to approximately 500 psig, approximately 50 psig to approximately 400 psig, approximately 50 psig to approximately 300 psig, approximately 50 psig to approximately 200 psig, approximately 50 psig to approximately 100 psig, approximately 100 psig to approximately 600 psig, and approximately 100 The procedure is performed at pressures of approximately psig to 500 psig, approximately 100 psig to 400 psig, approximately 100 psig to 300 psig, approximately 100 psig to 200 psig, approximately 200 psig to 600 psig, approximately 200 psig to 500 psig, approximately 200 psig to 400 psig, approximately 200 psig to 300 psig, approximately 300 psig to 600 psig, approximately 300 psig to 500 psig, approximately 300 psig to 400 psig, approximately 400 psig to 600 psig, approximately 400 psig to 500 psig, or approximately 500 psig to 600 psig.

[0037] In some embodiments, fluorination is carried out as gas-phase fluorination.

[0038] In some embodiments, gas-phase fluorination is carried out at temperatures of approximately 200°C to approximately 400°C, for example, approximately 200°C to approximately 350°C, approximately 200°C to approximately 300°C, approximately 200°C to approximately 250°C, approximately 250°C to approximately 400°C, approximately 250°C to approximately 350°C, approximately 250°C to approximately 300°C, approximately 300°C to approximately 400°C, approximately 300°C to approximately 350°C, or approximately 350°C to approximately 400°C.

[0039] In some embodiments, gas-phase fluorination is carried out at pressures of approximately 0 psig to approximately 200 psig, for example, approximately 0 psig to approximately 150 psig, approximately 0 psig to approximately 100 psig, approximately 0 psig to approximately 50 psig, approximately 0 psig to approximately 25 psig, approximately 25 psig to approximately 200 psig, approximately 25 psig to approximately 150 psig, approximately 25 psig to approximately 100 psig, approximately 25 psig to approximately 50 psig, approximately 50 psig to approximately 200 psig, approximately 50 psig to approximately 150 psig, approximately 50 psig to approximately 100 psig, approximately 100 psig to approximately 200 psig, approximately 100 psig to approximately 150 psig, or approximately 150 psig to approximately 200 psig.

[0040] In some embodiments, the catalyst is a chromium catalyst. Examples of chromium catalysts include, but are not limited to, chromium-based catalysts such as chromium oxyfluoride, which may be unsupported or supported on a carrier such as activated carbon, graphite, graphite fluoride, or alumina fluoride. The chromium catalyst may be used alone or in the presence of a co-catalyst selected from nickel, cobalt, manganese, or zinc salts. In one embodiment, the chromium catalyst is chromium oxide with a high surface area or chromium / nickel (Cr / Ni / AlF3) on alumina fluoride, the preparation of which is reported in European Patent No. 486,333, the disclosure of which is incorporated herein by reference in its entirety.

[0041] Chromium oxyfluoride catalysts can be prepared by treating Cr2O3 (chromium oxide) with HF, CCl3F, or hydrofluorocarbons. In some embodiments, chromium oxyfluoride catalysts are prepared by treating dry Cr2O3 with a fluorinating agent such as CCl3F or HF. This treatment can be achieved by placing Cr2O3 in a suitable container (which may be a reactor used to carry out the fluorination reaction described herein) and then passing HF over the dry Cr2O3 at a suitable temperature (e.g., about 200°C to 450°C) for a suitable period (e.g., about 15 to 300 minutes).

[0042] In some embodiments, chromium oxyfluoride catalysts can be prepared by treating Cr2O3 with hydrofluorocarbons at high temperatures. In some embodiments, chromium catalysts (e.g., chromium oxyfluoride catalysts) are prepared in situ. Exemplary methods for preparing Cr2O3 can be found in U.S. Patents 5,036,036, 4,828,818, and 3,258,500, the disclosures of which are incorporated herein by reference in their entirety.

[0043] In some embodiments, the catalyst is selected from chromium oxyfluoride, chromium oxyfluoride on activated carbon, chromium oxyfluoride on graphite, chromium oxyfluoride on fluoride graphite, chromium oxyfluoride on fluoride alumina, chromium oxide, high surface area chromium oxide, fluorinated alumina, and chromium / nickel on fluoride alumina. In some embodiments, the fluorination is liquid-phase fluorination, and the catalyst is a chromium catalyst. Additional examples of catalysts that may be suitable for one or more of the processes described herein can be found, for example, in International Publication No. 2018 / 022500, the disclosure of which is incorporated herein by reference in its entirety.

[0044] In some embodiments, the catalyst is activated before fluorination. In some embodiments, activation involves heating the catalyst to a temperature of about 350°C to about 400°C over a first period, for example, about 350°C to about 380°C, about 350°C to about 360°C, about 360°C to about 400°C, about 360°C to about 380°C, or about 380°C to about 400°C. In some embodiments, heating over the first period is carried out in the presence of nitrogen gas.

[0045] In some embodiments, activation further includes heating the catalyst to a temperature of about 350°C to about 400°C, for example, about 350°C to about 380°C, about 350°C to about 360°C, about 360°C to about 400°C, about 360°C to about 380°C, or about 380°C to about 400°C, in the presence of hydrogen fluoride over a second period.

[0046] In some embodiments, the heating over the second period is carried out in the presence of nitrogen, air, or a mixture thereof. In some embodiments, the heating over the second period is carried out in the presence of nitrogen. In some embodiments, the heating over the second period is carried out in the presence of air. In some embodiments, the heating over the second period is carried out in the presence of a mixture of nitrogen and air.

[0047] In some embodiments, 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane is prepared by a process comprising reacting 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane with 3,3,3-trifluoropropane-1-ene in the presence of an iron catalyst and a trialkyl phosphate or phosphine ligand.

[0048] In some embodiments, the iron catalyst is a metal ferrous iron. In some embodiments, the metallic iron component of the iron catalyst may originate from any source (including combinations of sources) of iron components, including but not limited to iron powder, iron wire, iron screen, or iron shavings. In some embodiments, the iron catalyst is iron chloride. In some embodiments, the iron catalyst is iron(III) chloride. In some embodiments, the iron catalyst is a combination of a metal ferrous iron and iron chloride. In some embodiments, the iron catalyst is a combination of a metal ferrous iron and iron(III) chloride. Addition

[0049] In some embodiments, 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane is prepared in the presence of an iron catalyst and a trialkyl phosphate. In some embodiments, the trialkyl phosphate is tri(C 1-6 It is an alkyl) phosphate. In some embodiments, it is a trialkyl phosphate (e.g., tri(C) 1-6 The alkyl phosphate is tributyl phosphate.

[0050] In some embodiments, 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane is prepared in the presence of an iron catalyst and a phosphine ligand. In some embodiments, the phosphine ligand is selected from alkylphosphines or arylphosphines. Examples of phosphine ligands include, but are not limited to, triphenylphosphine and tributylphosphine. Examples of phosphine ligands can be found, for example, in International Publication No. 2018 / 022500, the disclosure of which is incorporated herein by reference in whole.

[0051] In some embodiments, the reaction between 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane and 3,3,3-trifluoropropane-1-ene is carried out at temperatures of about 50°C to about 250°C, for example, about 50°C to about 200°C, about 50°C to about 150°C, about 50°C to about 100°C, about 100°C to about 250°C, about 100°C to about 200°C, about 100°C to about 150°C, about 150°C to about 250°C, about 150°C to about 200°C, and about 200°C to about 250°C.

[0052] In some embodiments, the present application relates to a process for preparing (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, (i) Reacting 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane with 3,3,3-trifluoropropa-1-ene in the presence of an iron metal and tributyl phosphate to form 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane, (ii) Reacting 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane with hydrogen fluoride in the presence of a chromium catalyst to form (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, It provides a process that includes this.

[0053] In some embodiments, (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene prepared according to one or more of the processes described herein is substantially isolated. "Substantially isolated" means that the compound is at least partially or substantially separated from the environment in which it was formed or detected. Partial isolation may include, for example, a composition in which (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene is concentrated. Substantial isolation may include a composition containing at least about 50% by weight, at least about 60% by weight, at least about 70% by weight, at least about 80% by weight, at least about 90% by weight, at least about 95% by weight, at least about 97% by weight, or at least about 99% by weight of (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene. Methods for isolating compounds are commonplace in the art.

[0054] In some embodiments, the processes described herein may be carried out in a reaction zone including any reaction vessel of an appropriate size for the scale of the reaction. In some embodiments, the reaction zone includes a reaction vessel made of a corrosion-resistant material. In some embodiments, the material includes an alloy, for example, a nickel-based alloy such as Hastelloy®, a nickel-chromium alloy commercially available from Special Metals Corp. (New Hartford, New York) under the trade name Inconel®, or a nickel-copper alloy commercially available from Special Metals Corp. under the trade name Monel®, or a vessel having a fluoropolymer lining. In some embodiments, the reaction vessel may include, but is not limited to, austenitic stainless steel and other materials with a copper cladding.

[0055] Composition of the present invention This application further provides compositions comprising one or more major components (e.g., (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene) in combination with one or more additional compounds (i.e., trace components). For example, the presence of additional compounds in a sample containing one or more of the major components (e.g., (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene) can be used to identify the process by which one or more of the major components were produced. In some embodiments, the compositions are prepared according to one or more processes described herein.

[0056] Therefore, this application is, (i)(E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, (ii) One or more compounds selected from the following: (Z)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2ene, Hexafluoropropa-1-ene, and 1,3,3,3-tetrafluoropropane-1-ene The present invention provides a composition containing the following:

[0057] In some embodiments, the composition contains about 2 to about 3 mole percent of (Z)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene. In some embodiments, the composition further comprises SbF5.

[0058] In some embodiments, the composition (i)(E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, (ii) One or more compounds selected from the following: (Z)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2ene, Hexafluoropropa-1-ene, and 1,3,3,3-tetrafluoropropane-1-ene and a composition containing It is prepared according to the process described herein.

[0059] In some embodiments, the composition (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2ene, (Z)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2ene, Hexafluoropropa-1-ene, and 1,3,3,3-tetrafluoropropane-1-ene Includes.

[0060] In some embodiments, compositions comprising (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, (Z)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, hexafluoropropa-1-ene, and 1,3,3,3-tetrafluoropropa-1-ene are prepared according to the processes described herein.

[0061] This application further provides compositions comprising (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene and 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane. In some embodiments, the composition further comprises hydrogen fluoride, chromium oxyfluoride, or a combination thereof. In some embodiments, the composition further comprises hydrogen fluoride. In some embodiments, the composition further comprises chromium oxyfluoride. In some embodiments, the composition further comprises a combination of hydrogen fluoride and chromium oxyfluoride. In some embodiments, the composition comprising (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene and 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane is prepared according to the processes described herein.

[0062] This application further states, (i) 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane, (ii) One or more compounds selected from 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane and 3,3,3-trifluoropropane-1-ene, Includes a composition containing the following:

[0063] In some embodiments, the composition includes an iron metal, iron chloride, and a trialkyl phosphate (e.g., tri(C) 1~6 The composition further comprises an alkyl phosphate, or any combination thereof. In some embodiments, the composition comprises an iron metal, iron chloride, and tri(C) 1~6 The composition further comprises an alkyl phosphate, or any combination thereof. In some embodiments, the composition further comprises an iron metal, iron(III) chloride, and tributyl phosphate, or any combination thereof. In some embodiments, the composition further comprises an iron metal, tributyl phosphate, or any combination thereof.

[0064] In some embodiments, (i) 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane, (ii) One or more compounds selected from 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane and 3,3,3-trifluoropropane-1-ene, composition containing It is prepared according to the process described herein.

[0065] In some embodiments, the composition 2,4-Dichloro-1,1,1,5,5,5-Hexafluoro-2-(trifluoromethyl)pentane, 2,2-Dichloro-1,1,1,3,3,3-Hexafluoropropane, and 3,3,3-trifluoropropa-1-ene Includes.

[0066] In some embodiments, compositions comprising 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane, 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane, and 3,3,3-trifluoropropane-1-ene are prepared according to the processes described herein.

[0067] This application further states, (i)(E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, (ii) One or more compounds selected from 1,1,1,4,5,5,5-heptafluoro-2-(trifluoromethyl)penta-2-ene (HFO-153-10mezt), (E)-4-chloro-1,1,1,5,5,5-hexafluoro-4-(trifluoromethyl)penta-2-ene (HCFO-153-10mzzx), and 1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)penta-2,3-diene (HFO-1529mztt), The present invention provides a composition containing the following:

[0068] In some embodiments, the composition further comprises 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane. In some embodiments, the composition further comprises hydrogen fluoride. In some embodiments, the composition further comprises the chromium catalyst described herein.

[0069] In some embodiments, the composition (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2ene, 1,1,1,4,5,5,5-heptafluoro-2-(trifluoromethyl)penta-2-ene (HFO-153-10mezt), (E)-4-chloro-1,1,1,5,5,5-hexafluoro-4-(trifluoromethyl)penta-2-ene (HCFO-153-10mzzx), and 1,1,1,5,5,5-Hexafluoro-2-(trifluoromethyl)penta-2,3-diene (HFO-1529mztt) Includes.

[0070] In some embodiments, compositions comprising (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, 1,1,1,4,5,5,5-heptafluoro-2-(trifluoromethyl)penta-2-ene (HFO-153-10mezt), (E)-4-chloro-1,1,1,5,5,5-hexafluoro-4-(trifluoromethyl)penta-2-ene (HCFO-153-10mzzx), and 1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)penta-2,3-diene (HFO-1529mztt) are prepared according to the processes described herein.

[0071] In some embodiments, the composition (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2ene, 1,1,1,4,5,5,5-heptafluoro-2-(trifluoromethyl)penta-2-ene (HFO-153-10mezt), (E)-4-chloro-1,1,1,5,5,5-hexafluoro-4-(trifluoromethyl)penta-2-ene (HCFO-153-10mzzx), 1,1,1,5,5,5-Hexafluoro-2-(trifluoromethyl)penta-2,3-diene (HFO-1529mztt), and 2,4-Dichloro-1,1,1,5,5,5-Hexafluoro-2-(trifluoromethyl)pentane Includes.

[0072] In some embodiments, compositions comprising (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, 1,1,1,4,5,5,5-heptafluoro-2-(trifluoromethyl)penta-2-ene (HFO-153-10mezt), (E)-4-chloro-1,1,1,5,5,5-hexafluoro-4-(trifluoromethyl)penta-2-ene (HCFO-153-10mzzx), 1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)penta-2,3-diene (HFO-1529mztt), and 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane are prepared according to the processes described herein. [Examples]

[0073] The present invention will be described in more detail by specific examples. The following examples are provided for illustrative purposes only and are not intended to limit the invention in any way. Those skilled in the art will readily recognize various non-essential parameters that can be changed or modified to obtain essentially the same results.

[0074] Example 1. Preparation of (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene (F13iE)

[0075] [ka] Step 1. Preparation of 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane (HFC-549mdfx)

[0076] [ka] 222 g of (CF-3)2CCl2 (i.e., HFC 216aa), 1 g of cut iron wire, 0.5 g of FeCl3, and 3 g of O=P(OBu)3 were charged into a 400 mL Hastelloy shaker tube. The shaker tube was closed, cooled with dry ice, evacuated, and purged with nitrogen. This cycle was repeated three times. Subsequently, 20 g of 3,3,3-trifluoropropa-1-ene (i.e., TFP) was charged into the tube. The tube was heated to 150°C, and an additional 76 g of TFP was added to the reaction vessel, which was maintained at 150°C for 12 hours. The reactor was then removed at ambient temperature, and 220 g of crude reaction mixture containing ~50% of the title product was isolated. The reaction mixture was subjected to vacuum distillation to obtain 75 g of 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane (yield 31%, purity 95%). 19 F NMR(CDCl3):-72.14(3F,q,10.8Hz),-72.59(3F,q,10.8Hz),-75.72(3F,d,6.7Hz)ppm; 1 H NMR(CDCl3):2.74(1H,m),2.96(1H,m),4.45(1H,quint.,6.8Hz)ppm;MS(m / z):316(M + , C6H3Cl2F9 + )

[0077] Step 2. Gas phase preparation of (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene (F13iE)

[0078] [ka] 4 cc of chromium catalyst was charged into an Inconel® pipe (OD 0.5 inch, length 10 inch, wall thickness 0.034). The reactor was heated to a target temperature of 325°C. 2,4-Dichloro-1,1,1,5,5,5-Hexafluoro-2-(trifluoromethyl)pentane (GC purity 96%) was supplied via an ISCO pump (0.38 mL / hour) and a vaporizer controlled to 140°C. The HF / organic molar ratio was 15, the contact time was 10 seconds, and the reaction was carried out at 0 psig. Online analysis of the reactor effluent using Agilent® 6890GC / 5973MS showed that 90% of the starting materials were converted, with a selectivity of 15-20% for (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene and 55-60% for (E)-4-chloro-1,1,1,5,5,5-hexafluoro-4-(trifluoromethyl)penta-2-ene.

[0079] The trace products observed included (E)-4-chloro-1,1,1,5,5,5-hexafluoro-4-(trifluoromethyl)penta-2-ene (HCFO-153-10mzzx), 1,1,1,4,5,5,5-heptafluoro-2-(trifluoromethyl)penta-2-ene (HFO-153-10mezt), and 1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)penta-2,3-diene (HFO-1529mztt).

[0080] Example 2. Another preparation of (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene (F13iE)

[0081] [ka] 10 g of freshly distilled antimony pentafluoride (SbF5) was charged into a 400 mL shaker tube. The tube was closed, cooled with dry ice, evacuated, and charged with 75 g of hexafluoropropene. The shaker tube was heated to 50 °C and HFO-1234ze was injected in 20 g increments (total 40 g). Heating was continued for 12 hours. 100 mL of water was injected into the reactor, the shaker tube was vented, and the contents were removed. 90 g of a crude reaction mixture containing ~60% (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene along with the dimer of HFO-1234ze was isolated (confirmed via GC / MS).

[0082] The reaction mixture was fractionated using a 50 cm Vigreux distillation column to afford 54 g (50% yield) of (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene. b.p. 48 - 49 °C (E / Z isomer ratio 97:3). The title product was identified by comparison with a standard prepared by an independent method. 19 19F NMR (CDCl3): -65.91 (3F, dd, 3.8, 1.8 Hz), -76.75 (6F, d, 7.6 Hz), -187.43 (1F, m) ppm; 1 1H NMR (CDCl3): 6.44 (m) ppm; MS (m / z): 264 (M + , C6H2F 10 + ).

[0083] Other Embodiments 1. In some embodiments, the present application provides a process for preparing (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, which comprises reacting hexafluoroprop-1-ene with 1,3,3,3-tetrafluoroprop-1-ene in the presence of an acid catalyst. 2. The process according to embodiment 1, wherein the acid catalyst is a Lewis acid catalyst. 3. The process according to embodiment 1, wherein the acid catalyst is a strong Lewis acid catalyst. 4. The process according to Embodiment 1, wherein the acid catalyst is selected from SbF5, aluminum chlorofluoride (ACF), and aluminum chloride. 5. The process according to Embodiment 1, wherein the acid catalyst is SbF5. 6. The process according to any one of Embodiments 1 to 5, wherein the reaction is carried out at a temperature of approximately -30°C to approximately 100°C. 7. The process according to any one of Embodiments 1 to 5, wherein the reaction is carried out at a temperature of approximately 25°C to approximately 75°C. 8. The process according to any one of Embodiments 1 to 5, wherein the reaction is carried out at a temperature of approximately 40°C to approximately 60°C. 9. The process according to any one of Embodiments 1 to 8, wherein the reaction is carried out at a pressure of approximately 1 atm to approximately 25 atm. 10. The method according to any one of Embodiments 1 to 9, wherein the reaction is carried out as a liquid-phase reaction. 11. The process according to any one of Embodiments 1 to 10, wherein the process is carried out in the absence of additional solvent components. 12. The process according to any one of Embodiments 1 to 11, wherein the process comprises pre-mixing the hexafluoropropa-1-ene and the acid catalyst to form a first mixture before reacting the hexafluoropropa-1-ene with the 1,3,3,3-tetrafluoropropa-1-ene. 13. The process according to Embodiment 12, wherein the mixing of hexafluoropropa-1-ene and the acid catalyst is carried out in a liquid phase. 14. The process according to Embodiment 12 or 13, wherein the first mixture is a liquid. 15. The process according to any one of embodiments 12 to 14, wherein the premixing is carried out at a pressure of approximately 1 atm to approximately 25 atm. 16. The process according to any one of Embodiments 12 to 15, further comprising adding the 1,3,3,3-tetrafluoropropane-1-ene to the first mixture to form (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene. 17. In some embodiments, the present application provides a process for preparing (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, comprising fluorinating 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane in the presence of a catalyst. 18. The process according to Embodiment 17, wherein the fluorination comprises reacting 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane in the presence of a fluorinating agent. 19. The process according to Embodiment 18, wherein about 6 to about 25 molar equivalents of a fluorinating agent are used based on 1 equivalent of the 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane. 20. The process according to Embodiment 18 or 19, wherein the fluorinating agent is selected from hydrogen fluoride, antimony trifluoride, antimony tetrafluoride, antimony pentafluoride, antimony trichloride / hydrogen fluoride, antimony tetrachloride / hydrogen fluoride, or any mixture thereof. 21. The process according to any one of Embodiments 17 to 20, wherein the fluorination is carried out as liquid-phase fluorination. 22. The process according to any one of Embodiments 17 to 21, wherein the fluorination is carried out at a temperature of approximately 50°C to approximately 150°C. 23. The process according to any one of embodiments 17 to 22, wherein the fluorination is carried out at a pressure of approximately 0 psig to approximately 600 psig. 24. The process according to any one of Embodiments 17 to 23, wherein the fluorinating agent is hydrogen fluoride. 25. The process according to any one of embodiments 17 to 24, wherein the catalyst is a chromium catalyst. 26. The process according to any one of Embodiments 17 to 24, wherein the catalyst is selected from chromium oxyfluoride, chromium oxyfluoride on activated carbon, chromium oxyfluoride on graphite, chromium oxyfluoride on fluoride graphite, chromium oxyfluoride on fluoride alumina, chromium oxide, high surface area chromium oxide, fluorinated alumina, and chromium / nickel on fluoride alumina. 27. The process according to any one of embodiments 17-20 and 24-26, wherein the fluorination is carried out as gas-phase fluorination. 28. The process according to Embodiment 27, wherein the fluorination is carried out at a temperature of approximately 200°C to approximately 400°C. 29. The process according to Embodiment 27 or 28, wherein the fluorination is carried out at a pressure of approximately 0 psig to approximately 200 psig. 30. The process according to any one of Embodiments 17 to 29, wherein the catalyst is activated before the fluorination. 31. The process according to Embodiment 30, wherein the activation comprises heating the catalyst to a temperature of about 350°C to about 400°C over a first period. 32. The process according to Embodiment 31, wherein the heating over the first period is carried out in the presence of nitrogen gas. 33. The process according to any one of embodiments 30 to 32, wherein the activation further comprises heating the catalyst to a temperature of about 350°C to about 400°C in the presence of hydrogen fluoride over a second period. 34. The process according to Embodiment 33, wherein the heating over the second period is carried out in the presence of nitrogen, air, or a mixture thereof. 35. The process according to any one of Embodiments 17 to 34, wherein the 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane is prepared by a process comprising reacting 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane with 3,3,3-trifluoropropa-1-ene in the presence of an iron catalyst and a trialkyl phosphate. 36. The process according to Embodiment 35, wherein the iron catalyst is an iron metal. 37. The trialkyl phosphate is tri(C 1-6 The process according to embodiment 35 or 36, wherein the alkyl phosphate is used. 38. The relevant bird (C 1-6 The process according to Embodiment 36, wherein the alkyl) phosphate is tributyl phosphate. 39. The process according to any one of embodiments 35 to 38, wherein the reaction is carried out at a temperature of approximately 50°C to approximately 250°C. 40. In some embodiments, this application is valid. (i)(E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, (ii) One or more compounds selected from the following: (Z)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2ene, Hexafluoropropa-1-ene, and 1,3,3,3-tetrafluoropropane-1-ene The present invention provides a composition containing the following: 41. The composition according to Embodiment 40, wherein the composition contains about 2 to about 3 mole percent of (Z)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene. 42. The composition according to Embodiment 40 or 41, wherein the composition further comprises SbF5. 43. In some embodiments, this application is, (i)(E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, (ii) One or more compounds selected from the following: (Z)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2ene, Hexafluoropropa-1-ene, and 1,3,3,3-tetrafluoropropane-1-ene and, The present invention provides a composition prepared according to the process described in any one of Embodiments 1 to 16. 44. In some embodiments, this application is valid. (i)(E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, (ii) One or more compounds selected from the following: 1,1,1,4,5,5,5-heptafluoro-2-(trifluoromethyl)penta-2-ene, (E)-4-chloro-1,1,1,5,5,5-hexafluoro-4-(trifluoromethyl)penta-2-ene, and 1,1,1,5,5,5-Hexafluoro-2-(trifluoromethyl)penta-2,3-diene The present invention provides a composition containing the following: 45. The composition according to Embodiment 44, wherein the composition further comprises 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane. 46. ​​The composition according to Embodiment 44 or 45, wherein the composition further comprises hydrogen fluoride, chromium oxyfluoride, or a combination thereof. 47. In some embodiments, this application is, (i)(E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, (ii) One or more compounds selected from the following: 1,1,1,4,5,5,5-heptafluoro-2-(trifluoromethyl)penta-2-ene, (E)-4-chloro-1,1,1,5,5,5-hexafluoro-4-(trifluoromethyl)penta-2-ene, 1,1,1,5,5,5-Hexafluoro-2-(trifluoromethyl)penta-2,3-diene, and 2,4-Dichloro-1,1,1,5,5,5-Hexafluoro-2-(trifluoromethyl)pentane and, The present invention provides a composition prepared according to the process described in any one of Embodiments 17 to 39. 48. In some embodiments, the present application provides compositions comprising (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene and 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane, which are prepared according to the process described in any one of Embodiments 17 to 39. 49. In some embodiments, this application is valid. (i) 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane, (ii) One or more compounds selected from 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane and 3,3,3-trifluoropropane-1-ene, The present invention provides a composition containing the following: 50. The composition according to Embodiment 49, wherein the composition further comprises iron metal, iron chloride, tributyl phosphate, or any combination thereof. 51. In some embodiments, this application is, (i) 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane, (ii) One or more compounds selected from 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane and 3,3,3-trifluoropropane-1-ene, Includes, The present invention provides a composition prepared according to the process described in any one of embodiments 35 to 39.

[0084] While the present invention has been described in conjunction with its detailed description, it should be understood that the foregoing description is intended to illustrate, and not limit, the scope of the invention as defined by the appended claims. Other aspects, advantages, and modifications are within the scope of the following claims. It should be understood by those skilled in the art related to the present invention that any feature described herein with respect to any particular aspect and / or embodiment of the present invention can be combined with one or more other features of any other aspect and / or embodiment of the present invention described herein, and can be modified as appropriate to ensure the suitability of the combination. Such combinations are deemed to be part of the present invention as contemplated by this disclosure. The main inventions described herein are listed below. (1) A process for preparing (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, comprising reacting hexafluoropropa-1-ene with 1,3,3,3-tetrafluoropropa-1-ene in the presence of an acid catalyst. (2) The process according to (1), wherein the acid catalyst is a Lewis acid catalyst. (3) The process according to (1), wherein the acid catalyst is a strong Lewis acid catalyst. (4) The process according to (1), wherein the acid catalyst is selected from SbF5, aluminum chlorofluoride (ACF), and aluminum chloride. (5) The process according to (1), wherein the acid catalyst is SbF5. (6) The process according to (1), wherein the reaction is carried out at a temperature of about -30°C to about 100°C. (7) The process according to (1), wherein the reaction is carried out at a temperature of approximately 25°C to approximately 75°C. (8) The process according to (1), wherein the reaction is carried out at a temperature of about 40°C to about 60°C. (9) The process according to (1), wherein the reaction is carried out at a pressure of about 1 atm to about 25 atm. (10) The process according to (1), wherein the reaction is carried out as a liquid-phase reaction. (11) The process according to (1), wherein the process is carried out in the absence of additional solvent components. (12) The process according to (1), wherein the process comprises premixing the hexafluoropropa-1-ene and the acid catalyst to form a first mixture before reacting with the 1,3,3,3-tetrafluoropropa-1-ene. (13) The process according to (12), wherein the mixing of the hexafluoropropa-1-ene and the acid catalyst is carried out in a liquid phase. (14) The process according to (12), wherein the first mixture is a liquid. (15) The process according to (12), wherein the premixing is carried out at a pressure of about 1 atm to about 25 atm. (16) The process according to (12), further comprising adding the 1,3,3,3-tetrafluoropropane-1-ene to the first mixture to form (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene. (17) A process for preparing (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, comprising fluorinating 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane in the presence of a catalyst. (18) The process according to (17), wherein the fluorination comprises reacting 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane in the presence of a fluorinating agent. (19) The process according to (18), using about 6 to about 25 molar equivalents of a fluorinating agent based on 1 equivalent of the aforementioned 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane. (20) The process according to (18), wherein the fluorinating agent is selected from hydrogen fluoride, antimony trifluoride, antimony tetrafluoride, antimony pentafluoride, antimony trichloride / hydrogen fluoride, antimony tetrachloride / hydrogen fluoride, or any mixture thereof. (21) The process according to (20), wherein the fluorination is carried out as liquid-phase fluorination. (22) The process according to (21), wherein the fluorination is carried out at a temperature of about 50°C to about 150°C. (23) The process according to (21), wherein the fluorination is carried out at a pressure of about 0 psig to about 600 psig. (24) The process according to (18), wherein the fluorinating agent is hydrogen fluoride. (25) The method according to (18), wherein the catalyst is a chromium catalyst. (26) The process according to (18), wherein the catalyst is selected from chromium oxyfluoride, chromium oxyfluoride on activated carbon, chromium oxyfluoride on graphite, chromium oxyfluoride on fluoride graphite, chromium oxyfluoride on fluoride alumina, chromium oxide, high surface area chromium oxide, fluorinated alumina, and chromium / nickel on fluoride alumina. (27) The process according to (26), wherein the fluorination is carried out as gas-phase fluorination. (28) The process according to (27), wherein the fluorination is carried out at a temperature of about 200°C to about 400°C. (29) The process according to (27), wherein the fluorination is carried out at a pressure of about 0 psig to about 200 psig. (30) The process according to (18), wherein the catalyst is activated before the fluorination. (31) The process according to (30), wherein the activation comprises heating the catalyst to a temperature of about 350°C to about 400°C over a first period. (32) The process according to (31), wherein the heating over the first period is carried out in the presence of nitrogen gas. (33) The process according to (31), wherein the activation further comprises heating the catalyst to a temperature of about 350°C to about 400°C in the presence of hydrogen fluoride over a second period. (34) The process according to (33), wherein the heating over the second period is carried out in the presence of nitrogen, air, or a mixture thereof. (35) The process according to (18), wherein the 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane is prepared by a process comprising reacting 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane with 3,3,3-trifluoropropa-1-ene in the presence of an iron catalyst and a trialkyl phosphate. (36) The process according to (35), wherein the iron catalyst is an iron metal. (37) The trialkyl phosphate is tri(C 1~6 The process described in (35), wherein the alkyl) phosphate is used. (38) The aforementioned Tri(C 1~6 The process according to (35), wherein the alkyl) phosphate is tributyl phosphate. (39) The process according to (35), wherein the reaction is carried out at a temperature of about 50°C to about 250°C. (40) A composition, (i)(E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, (ii) One or more compounds selected from the following: (Z)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2ene, Hexafluoropropa-1-ene, and 1,3,3,3-tetrafluoropropane-1-ene A composition containing the following. (41) The composition according to (40), wherein the composition comprises about 2 to about 3 mole percent of (Z)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene. (42) The composition according to (40), wherein the composition further comprises SbF5. (43) A composition, (i)(E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, (ii) One or more compounds selected from the following: (Z)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2ene, Hexafluoropropa-1-ene, and 1,3,3,3-tetrafluoropropane-1-ene and, A composition prepared according to the process described in (1). (44) A composition, (i)(E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, (ii) One or more compounds selected from the following: 1,1,1,4,5,5,5-heptafluoro-2-(trifluoromethyl)penta-2-ene, (E)-4-chloro-1,1,1,5,5,5-hexafluoro-4-(trifluoromethyl)penta-2-ene, and 1,1,1,5,5,5-Hexafluoro-2-(trifluoromethyl)penta-2,3-diene A composition containing the following. (45) The composition according to (44), wherein the composition further comprises 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane. (46) The composition according to (44), wherein the composition further comprises hydrogen fluoride, chromium oxyfluoride, or a combination thereof. (47) A composition, (i)(E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, (ii) One or more compounds selected from the following: 1,1,1,4,5,5,5-heptafluoro-2-(trifluoromethyl)penta-2-ene, (E)-4-chloro-1,1,1,5,5,5-hexafluoro-4-(trifluoromethyl)penta-2-ene, 1,1,1,5,5,5-Hexafluoro-2-(trifluoromethyl)penta-2,3-diene, and 2,4-Dichloro-1,1,1,5,5,5-Hexafluoro-2-(trifluoromethyl)pentane and, A composition prepared according to the process described in (17). (48) A composition, (i) 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane, (ii) One or more compounds selected from 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane and 3,3,3-trifluoropropane-1-ene, A composition containing the following: (49) The composition according to (48), wherein the composition further comprises an iron metal, iron chloride, tributyl phosphate, or any combination thereof. (50) A composition, (i) 2,4-dichloro-1,1,1,5,5,5-hexafluoro-2-(trifluoromethyl)pentane, (ii) One or more compounds selected from 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane and 3,3,3-trifluoropropane-1-ene, Includes, A composition prepared according to the process described in (35).

Claims

1. A process for preparing (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene, comprising reacting hexafluoropropa-1-ene with 1,3,3,3-tetrafluoropropa-1-ene in the presence of an acid catalyst.

2. The acid catalyst is SbF 5 The process according to claim 1, selected from aluminum chlorofluoride (ACF) and aluminum chloride.

3. The process according to claim 1, wherein the process comprises pre-mixing the hexafluoroproper-1-ene and the acid catalyst to form a first mixture before reacting with the 1,3,3,3-tetrafluoroproper-1-ene.

4. The process according to claim 3, further comprising adding the 1,3,3,3-tetrafluoropropa-1-ene to the first mixture to form (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)penta-2-ene.

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