E-Fluorobutene Compositions Containing 1,1,1,4,4,4-Hexafluoro-2-butene and Uses Thereof

Abstract

The present disclosure relates to fluorobutene compositions, including E-1,1,1,4,4,4-hexafluoro-2-butene and fluorinated compounds, that may be useful as refrigerants, heat transfer compositions, aerosol propellants, foaming agents, blowing agents, solvents, cleaning agents, dispersion media, displacement drying agents, buffing agents, polymerization media, blowing agents for polyolefins and polyurethanes, gas dielectrics, power cycle working fluids, fire extinguishing agents, and fire suppressants in liquid or gas form, and in methods for detecting leaks.

Description

[Technical field]

[0001] The present invention relates generally to fluorobutene compositions, including E-1,1,1,4,4,4-hexafluoro-2-butene (E-1336mzz), that have improved performance, particularly in cooling applications. [Background technology]

[0002] New environmental regulations have created a need for new compositions for use in a wide range of applications, including use as aerosol propellants, refrigerants, cleaning agents, blowing agents for thermoplastic and thermosetting foams, heat transfer media, gas dielectrics, fire extinguishing and suppressing agents, power cycle working fluids, polymerization media, particulate removal fluids, dispersion media, buffing abrasives, and displacement drying agents.Compounds with low ozone depletion potential and low global warming potential are of particular interest.It is believed that certain hydrofluoroolefin compositions meet both of these goals.

[0003] E-HFO-1336mzz (E or trans-1,1,1,4,4,4-hexafluoro-2-butene, trans-CFCH=CHCF) and Z-HFO-1336mzz (Z or cis-1,1,1,4,4,4-hexafluoro-2-butene, cis-CFCH=CHCF), both have zero ozone depletion potential and low global warming potential and have been identified as potential refrigerants. WO 2007 / 53697 discloses compositions comprising E and / or Z-HFO-1336mzz and their use in various applications. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] WO 2007 / 53697 Summary of the Invention [Means for solving the problem]

[0005] E-1,1,1,4,4,4-hexafluoro-2-butene (E-HFO-1336mzz) can be used as a refrigerant, heat transfer fluid, foam expansion agent, power cycle working fluid, among other uses. It has also been advantageously found that E-HFO-1336mzz has a low global warming potential (GWP), GWP=32. Thus, fluorobutene compositions including E-HFO-1336mzz may be good candidates for replacing higher GWP saturated compounds such as CFCs (chlorofluorocarbons), HCFCs (hydrochlorofluorocarbons), or HFCs (hydrofluorocarbons) in many uses.

[0006] The present disclosure provides fluorobutene compositions comprising E-1,1,1,4,4,4-hexafluoro-2-butene (referred to herein as E-1336mzz or E1336mzz). More specifically, the compositions comprise E-1336mzz and one or more fluorinated compounds. The fluorinated compounds enhance the properties of E-1336mzz in applications such as use as a heat transfer fluid.

[0007] The present disclosure provides a fluorobutene composition comprising E-1,1,1,4,4,4-hexafluoro-2-butene and a fluorinated compound selected from the group consisting of 1,1,1,2,4,4,4-heptafluorobutane, 2-chloro-1,1,1-trifluoroethane, E-1-chloro-3,3,3-trifluoropropene, Z-1-chloro-3,3,3-trifluoropropene, and 2-chloro-3,3,3-trifluoropropene. The fluorobutene composition comprises at least 99% by weight of E-1,1,1,4,4,4-hexafluoro-2-butene.

[0008] The fluorobutene compositions may be used as refrigerants, heat transfer compositions, thermodynamic cycle (e.g., heating or cooling cycle) working fluids, gas dielectrics, power cycle working fluids, and as aerosol propellants, foaming agents (blowing agents), solvents, cleaning agents, dispersion media, displacement drying agents, buffing agents, polymerization media, blowing agents for polyolefins and polyurethanes, fire extinguishing agents, and fire suppression agents in liquid or gas form.

[0009] In some embodiments, the fluorobutene composition comprises 0.0001-0.9 wt. % of the fluorinated compound, or 0.0005-0.4 wt. % of the fluorinated compound, or 0.005-0.2 wt. % of the fluorinated compound.

[0010] In some embodiments, the fluorinated compound is 1,1,1,2,4,4,4-heptafluorobutane, or 2-chloro-1,1,1-trifluoroethane, or E-1-chloro-3,3,3-trifluoropropene, or Z-1-chloro-3,3,3-trifluoropropene, or 2-chloro-3,3,3-trifluoropropene.

[0011] In some embodiments, the fluorinated compound further comprises Z-1,1,1,4,4,4-hexafluoro-2-butene.

[0012] In some embodiments, the fluorobutene composition comprises E-1336mzz and E-1233zd, or E-1336mzz, E-1233zd, and Z-1336mzz.

[0013] In some embodiments, the fluorobutene composition has improved cooling performance over that of E-1336mzz alone. In certain embodiments, the performance improvement is a higher cooling capacity. In certain embodiments, the performance improvement is a higher efficiency (COP).

[0014] In some embodiments, the fluorobutene compositions include lubricants. In certain embodiments, such compositions exhibit improved solubility of the lubricant with E1336mzz and improved lubricity in heat transfer systems.

[0015] The fluorobutene compositions disclosed herein are non-flammable. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0016] composition E-HFO-1336mzz may be produced, for example, by reaction of chlorinated hydro(fluoro)carbons, such as CF3CHClCH2CCl3 (HCFC-343jfd), or CF3CHClCH2CF3 (HCFC-346mdf), or CCl3CHClCH2CCl3 (HCC-340jfd), or CCl2=CClCH=CCl2 (HCO-2320az), in the liquid or gas phase, or by isomerization of Z-HFO-1336mzz. Processes for preparing E-HFO-1336mzz are disclosed, for example, in U.S. Patent Nos. 9,174,896, 10,479,745, 10,611,709, U.S. Patent Application Publication Nos. 2021 / 0188743, WO 2020 / 206247, and WO 2020 / 206335. Such disclosures are incorporated herein by reference. Other processes for producing E-HFO-1336mzz are known to those of skill in the art.

[0017] In one embodiment, the present disclosure provides a fluorobutene composition comprising E-1,1,1,4,4,4-hexafluoro-2-butene and a fluorinated compound selected from the group consisting of 1,1,1,2,4,4,4-heptafluorobutane, 1,1,1,3,3-pentafluoropropane, 2-chloro-1,1,1-trifluoroethane, E-1-chloro-3,3,3-trifluoropropene, Z-1-chloro-3,3,3-trifluoropropene, and 2-chloro-3,3,3-trifluoropropene. The fluorobutene composition comprises at least 99% by weight of E-1,1,1,4,4,4-hexafluoro-2-butene.

[0018] E-HFO-1336mzz and fluorinated compounds are commercially available or can be made by processes known in the art. Such compounds can be purchased from specialized fluorochemical suppliers, such as SynQuest Laboratories, Inc. (Alachua, Florida, USA).

[0019] E-HFO-1336mzz may be produced, for example, by reaction of chlorinated hydro(fluoro)carbons, such as CF3CHClCH2CCl3 (HCFC-343jfd), or CF3CHClCH2CF3 (HCFC-346mdf), or CCl3CHClCH2CCl3 (HCC-340jfd), or CCl2=CClCH=CCl2 (HCO-2320az), in the liquid or gas phase, or by isomerization of Z-HFO-1336mzz. Processes for preparing E-HFO-1336mzz are disclosed, for example, in U.S. Patent Nos. 9,174,896, 10,479,745, 10,611,709, U.S. Patent Application Publication Nos. 2021 / 0188743, WO 2020 / 206247, and WO 2020 / 206335. Such disclosures are incorporated herein by reference. Other processes for producing E-HFO-1336mzz are known to those of skill in the art.

[0020] The compositions of the present invention may contain E-HFO-1336mzz and one fluorinated compound, or two fluorinated compounds, or three or more fluorinated compounds.

[0021] In one embodiment, the total amount of fluorinated compounds in the composition comprising E-HFO-1336mzz is in the range of from greater than zero weight percent to less than 1.0 weight percent, based on the total weight of the composition. In another embodiment, the total amount of fluorinated compounds is in the range of from greater than zero weight percent to less than 0.5 weight percent, based on the total weight of the composition. In another embodiment, the total amount of fluorinated compounds is in the range of from 0.01 ppm (by weight) to about 1 weight percent. In another embodiment, the total amount of fluorinated compounds is in the range of from 0.1 ppm (by weight) to about 1 weight percent. In another embodiment, the total amount of fluorinated compounds is in the range of from 0.001 weight percent to about 1 weight percent. In another embodiment, the total amount of fluorinated compounds is in the range of from 0.001 weight percent to about 0.5 weight percent.

[0022] Table 1 provides a list of fluorinated and other compounds that may be present in the fluorobutene compositions disclosed herein.

[0023] [Table 1]

[0024] For refrigerant applications such as use in air conditioning, heat pumps, refrigeration and power cycles (e.g., organic Rankine cycles), fluorinated compounds may also provide improved solubility in refrigeration lubricants such as mineral oil, alkylbenzenes, synthetic paraffins, synthetic naphthenes, poly(alpha)olefins, polyol esters (POE), polyalkylene glycols (PAG), polyvinyl ethers (PVE) or perfluoropolyethers (PFPE), or mixtures thereof.

[0025] In certain embodiments, the fluorinated compounds may also provide improved solubility for the active ingredient within the polymeric components of the aerosol or foam.

[0026] Fluorinated compounds may also provide improved solubility for the active ingredient within the polymeric components of the aerosol propellant or foam.

[0027] Unsaturated fluorocarbons, such as E-HFO-1336mzz, exhibit different solubility than other commonly used fluorocarbon propellants. Their low solubility can make the production of single-phase aqueous homogeneous aerosol formulations difficult. The presence of low levels of certain fluorinated compounds can improve mixing and facilitate use of the formulation and aerosol product.

[0028] Unsaturated fluorocarbons, such as E-HFO-1336mzz, also exhibit different solubility than other commonly used blowing agents. Their low solubility may act to promote initial small bubble growth during the foaming reaction, but may make mixing difficult. The presence of fluorinated compounds may improve mixing and foam processing performance without compromising the benefits of lower HFO solubility. Fluorinated compounds may also impart improved thermal insulation performance to foam insulation products.

[0029] For refrigerant applications such as use in air conditioning, heat pumps, refrigeration and power cycles (e.g., organic Rankine cycles), fluorinated compounds may also provide improved solubility in refrigeration lubricants such as mineral oil, alkylbenzenes, synthetic paraffins, synthetic naphthenes, poly(alpha)olefins, polyol esters (POE), polyalkylene glycols (PAG), polyvinyl ethers (PVE) or perfluoropolyethers (PFPE), or mixtures thereof.

[0030] Furthermore, certain fluorinated compounds may act to improve leak detection performance. Refrigerant leakage may result in loss of refrigerant from the system, thus increasing operating costs due to the need for refrigerant replenishment. Even a small amount of refrigerant loss from the system may prevent normal operation. Ultimately, refrigerant leakage may lead to excessive environmental pollution. Specifically, fluorinated compounds may improve the detection of refrigerant at the leak site, even at low levels. Thus, the system may be repaired or redesigned to prevent refrigerant leakage.

[0031] The presence of fluorinated compounds (as defined herein) in fluorobutene compositions with E-1336mzz can improve performance when the fluorobutene compositions are used in many applications, but the level of fluorination is kept low so as not to detract from the benefits of using E1336mzz instead of, for example, high GWP alternatives and other options.

[0032] Purpose The fluorobutene compositions disclosed herein, including E-HFO-1336mzz, are useful as heat transfer compositions with low global warming potential (GWP), refrigerants, power cycle working fluids, aerosol propellants, foaming agents, blowing agents, solvents, cleaning agents, dispersion media, displacement drying agents, buffing agents, polymerization media, blowing agents for polyolefins and polyurethanes, gas dielectrics, fire extinguishing agents, and fire suppressants in liquid or gas form. The disclosed compositions can act as working fluids used to transport heat from a heat source to a heat sink. Such heat transfer compositions may also be useful as refrigerants in cycles where the fluid undergoes a phase change, i.e., changing from liquid to gas and vice versa.

[0033] Exemplary heat transfer systems include, but are not limited to, air conditioners, freezers, refrigerators, heat pumps, water chillers, flooded evaporator chillers, direct expansion chillers, walk-in coolers, heat pumps, mobile refrigerators, mobile air conditioning units, and combinations thereof.

[0034] In one embodiment, compositions comprising E-HFO-1336mzz are useful in mobile heat transfer systems, including refrigeration, air conditioning, or heat pump systems or equipment. In another embodiment, the compositions are useful in stationary heat transfer systems, including refrigeration, air conditioning, or heat pump systems or equipment.

[0035] As used herein, a mobile heat transfer system refers to any cooling, air conditioning or heating equipment incorporated into a road, rail, sea or air transportation unit. In addition, a mobile cooling or air conditioning unit includes those equipment that are independent of any moving carrier and are known as "intermodal" systems. Such intermodal systems include "containers" (combined sea / land transportation) as well as "swap bodies" (combined road / rail transportation).

[0036] As used herein, a stationary heat transfer system is a system that is fixed in place during operation. Stationary heat transfer systems may be associated with or attached to any of a variety of buildings, or may be standalone devices located outdoors, such as soft drink vending machines. These stationary applications may be stationary air conditioning and heat pumps, including, but not limited to, transcritical heat pumps (with condenser temperatures greater than 50° C., 70° C., 80° C., 100° C., 120° C., 140° C., 160° C., 180° C., or 200° C.), residential, commercial, or industrial air conditioning systems, and chillers and high temperature heat pumps, including window, ductless, ducted, packaged terminal chillers, and their exteriors connected to buildings, e.g., rooftop systems). In stationary cooling applications, the disclosed compositions may be useful in high, medium and / or low temperature cooling appliances, including commercial, industrial or residential refrigerators and freezers, ice makers, self-contained coolers and freezers, flooded evaporator chillers, direct expansion chillers, walk-in and reach-in coolers and freezers, and combination systems. In some embodiments, the disclosed compositions may be used in supermarket refrigeration systems.

[0037] Thus, in accordance with the present invention, compositions as disclosed herein comprising E-HFO-1336mzz may be useful in methods for producing cooling, for achieving heating, and for heat transfer.

[0038] In one embodiment, a method is provided for producing cooling comprising evaporating any of the present compositions including E-HFO-1336mzz in the vicinity of an object to be cooled and then condensing the composition.

[0039] In another embodiment, a method for achieving heating is provided that includes condensing any of the present compositions including E-HFO-1336mzz in the vicinity of an object to be heated and then evaporating the composition.

[0040] In another embodiment, a method of using the composition comprising E-HFO-1336mzz as a heat transfer fluid composition is disclosed, the method comprising transporting the composition from a heat source to a heat sink.

[0041] In many applications, some embodiments of the present compositions comprising E-HFO-1336mzz are useful as refrigerants and provide at least the same cooling capacity (meaning cooling capacity and energy efficiency) as the refrigerant they seek to replace. Additionally, the compositions of the present invention provide heating performance (meaning heating capacity and energy efficiency) equivalent to the refrigerant they replace.

[0042] In another embodiment, the compositions of the present invention comprising Z-HFO-1336mzz may be used to supplement the refrigerant in a chiller. For example, if the performance of a chiller using HCFC-114 is compromised due to a refrigerant leak, the compositions disclosed herein can be added to restore performance to original specifications.

[0043] In another embodiment, there is provided a heat exchange system comprising any of the present compositions comprising E-HFO-1336mzz, the system being selected from the group consisting of systems having an air conditioner, a freezer, a refrigerator, a heat pump, a water chiller, a flooded evaporator chiller, a direct expansion chiller, a walk-in cooler, a heat pump, a mobile refrigerator, a mobile air conditioning unit, and combinations thereof. Additionally, compositions comprising E-HFO-1336mzz may be useful in secondary loop systems in which these compositions are used as the primary refrigerant to provide cooling for a secondary heat transfer fluid, thereby cooling a remote location.

[0044] In one embodiment, a heat transfer system is provided comprising any of the present compositions comprising E-HFO-1336mzz. In another embodiment, a refrigeration, air conditioning or heat pump appliance is disclosed comprising any of the present compositions comprising E-HFO-1336mzz. In another embodiment, a stationary refrigeration or air conditioning appliance is disclosed comprising any of the present compositions comprising E-HFO-1336mzz. In yet another embodiment, a mobile refrigeration or air conditioning appliance containing the composition disclosed herein is disclosed.

[0045] In one embodiment, the present invention relates to a method for providing heating in a high temperature heat pump comprising condensing a vapor working fluid comprising a composition comprising E-HFO-1336mzz in a condenser, thereby producing a liquid working fluid. The high temperature heat pump may be operated at a condenser temperature of at least about 100° C.

[0046] The high temperature heat pump may comprise a centrifugal compressor or a positive displacement compressor.

[0047] The method for achieving heating may further include passing a heat transfer medium through a condenser such that condensation of the working fluid heats the heat transfer medium, and passing the heated heat transfer medium from the condenser to an object to be heated.

[0048] The object to be heated may be any space, object, or fluid that can be heated, such as water or air for space heating. In one embodiment, the object to be heated may be a room, a building, or the cabin of an automobile. Alternatively, in another embodiment, the object to be heated may be a second medium or heat transfer fluid, such as a chemical process stream.

[0049] According to the present invention, there is provided a method for converting heat from a heat source into mechanical energy. The method includes heating a working fluid using heat provided from a heat source, expanding the heated working fluid to reduce the pressure of the working fluid, and generating mechanical energy when the pressure of the working fluid is reduced. The method is characterized by using a working fluid comprising the fluorobutene composition disclosed herein. The method for converting heat from a heat source into mechanical energy is a power cycle, which may be an organic Rankine cycle (ORC).

[0050] The method is provided for converting heat from a heat source into mechanical energy, and may be a subcritical power cycle, in which an organic working fluid used in the cycle receives heat at a pressure below the critical pressure of the organic working fluid, and the working fluid is maintained at a pressure below its critical pressure throughout the cycle.

[0051] The method is provided for converting heat from a heat source to mechanical energy, and may be a transcritical power cycle, in which an organic working fluid used in the cycle receives heat at a pressure above the critical pressure of the organic working fluid. In a transcritical cycle, the working fluid is compressed to a pressure above its critical pressure before heating, and then during expansion the working fluid pressure is reduced below its critical pressure.

[0052] The method is provided for converting heat from a heat source into mechanical energy, and may be a supercritical power cycle, in which a working fluid is maintained at a pressure above its critical pressure throughout a complete cycle (e.g., compression, heating, expansion and cooling).

[0053] In another embodiment, the present invention relates to foam expansion agent compositions comprising E-HFO-1336mzz that are used to make foams. In other embodiments, the present invention provides foamable compositions, preferably thermoset (such as polyurethane, polyisocyanurate or phenolic) and thermoplastic (such as polystyrene, polyethylene or polypropylene) foam compositions, and methods for preparing foams. In such foam embodiments, one or more of the present compositions comprising E-HFO-1336mzz are included as foam expansion agents within a foamable composition, which preferably includes one or more additional components that are capable of reacting and / or mixing under appropriate conditions and foaming to form a foam or cellular structure.

[0054] Disclosed herein is a process for preparing a thermoplastic foam, the process comprising providing a foamable composition comprising a thermoplastic polymer and a blowing agent, the blowing agent comprising a fluorobutene composition comprising E-HFO-1336mzz, the thermoplastic polymer comprising a polystyrene homopolymer, a polystyrene copolymer, a styrene-acrylonitrile copolymer, or a blend of two or more thereof, and expanding the foamable composition to produce a closed shell polymer foam.

[0055] The foamable composition for preparing thermoplastic foam may further include auxiliary blowing agents, nucleating agents, flame retardants, cell stabilizers, surfactants, preservatives, colorants, antioxidants, reinforcing agents, fillers, antistatic agents, IR attenuators, extrusion aids, plasticizers, viscosity modifiers, and other known additives, all in amounts to achieve the desired effect. Examples of nucleating agents are talc, graphite, and magnesium silicate. Examples of flame retardants include tetrabromo-bisphenol A and polymeric flame retardants.

[0056] Disclosed herein is a process for preparing polyurethane or polyisocyanurate foams, comprising reacting a polyisocyanate with an active hydrogen-containing compound in the presence of a blowing agent comprising a composition comprising E-HFO-1336mzz to obtain the foamed reaction product. Examples of active hydrogen-containing compounds include polyols, such as polyether or polyester polyols. Some hydroxyl groups can be replaced by amine groups, whereby the active hydrogen-containing compound contains both hydroxyl and amine groups. While any suitable polyisocyanate can be used in the process, examples of polyisocyanates that are useful for making polyisocyanate-based foams include at least one of aromatic, aliphatic, and cycloaliphatic polyisocyanates, among others.

[0057] Typically, an active hydrogen-containing compound and optionally other additives are mixed with a blowing agent prior to reaction with a suitable polyisocyanate to form a foam-forming composition. Such foam-forming compositions are typically known in the art as isocyanate-reactive preblends, or B-side compositions. The B-side composition contains an active hydrogen-containing compound and preferably also contains a blowing agent composition of the present invention. The A-side composition includes a polyisocyanate. The foam-forming composition, including the A-side composition and the B-side composition, can be prepared in any manner convenient to one of ordinary skill in the art, including simply weighing the desired amounts of each component and then combining them in a suitable vessel at the desired temperature and pressure.

[0058] It is often desirable to employ small amounts of additives in the B-side compositions, including one or more members of the group consisting of catalysts, surfactants, flame retardants such as TCPP, preservatives, colorants, antioxidants, reinforcing agents, fillers, and antistatic agents, among others well known in the art.

[0059] In the process of making polyurethane or polyisocyanurate or polyurethane / polyisocyanurate foams, active hydrogen-containing compounds, polyisocyanates, and other ingredients are contacted, thoroughly mixed, and allowed to expand and cure into a cellular polymer.

[0060] Another embodiment of the present invention relates to the use of the composition comprising E-HFO-1336mzz of the present invention as a propellant in a sprayable composition. Additionally, the present invention relates to a sprayable fluorobutene composition comprising E-HFO-1336mzz. The active ingredient to be sprayed together with the inert ingredients, solvents and other materials may be present in the sprayable composition. In one embodiment, the sprayable composition is an aerosol. The composition can be used to formulate medical drugs, such as anti-asthma drugs and breath fresheners, in addition to various industrial aerosols or other sprayable compositions, such as contact cleaners, dusters, lubricant sprays, mold release sprays, insecticides, and the like, as well as consumer aerosols, such as personal care products (e.g., hairsprays, deodorants and perfumes), household products (e.g., waxes, polishes, pan sprays, room fresheners and household insecticides) and automotive products (e.g., cleaners and polishers). Examples of these include metered dose inhalers (MDIs) for the treatment of asthma and other chronic obstructive pulmonary diseases, and for delivery of medication to accessible mucous membranes or intranasally.

[0061] The present invention further relates to a process for producing an aerosol product comprising the step of adding a fluorobutene composition comprising E-HFO-1336mzz of the present invention to a formulation including an active ingredient in an aerosol container, where the composition functions as a propellant. Additionally, the present invention further relates to a process for producing an aerosol product comprising the step of adding a fluorobutene composition comprising E-HFO-1336mzz of the present invention to a barrier type aerosol package (such as a bag in a can or a piston can) where the composition remains separate from other formulation components in the aerosol container and where the composition functions as a propellant. Additionally, the present invention further relates to a process for producing an aerosol product comprising the step of adding only a fluorobutene composition comprising E-HFO-1336mzz of the present invention to an aerosol package where the composition functions as an active ingredient (e.g., a duster, or a cooling or freezing spray).

[0062] Also provided is a method for detecting a leak from a container comprising sampling the air adjacent the container and detecting at least one fluorinated compound with a means for detecting the leak, wherein the container contains a fluorobutene composition of the invention comprising HFO-1336mzz-E.

[0063] The container may be any known container, system, or equipment filled with a fluorobutene composition including 1336mzz-E, including, but not limited to, storage containers, transport containers, aerosol cans, fire extinguishing systems, chiller equipment, heat pump equipment, heat transfer vessels, and power cycle equipment (e.g., organic Rankine cycle systems).

[0064] The means for detecting a leak may be any known sensor designed to detect leaks, including, but not limited to, electrochemical leak detectors, corona discharge leak detectors, and mass spectrometry leak detectors.

[0065] "Proximate" a container means within 12 inches of the container's exterior surface. Alternatively, adjacent may be within 6 inches, within 3 inches, or within 1 inch of the container's exterior surface.

[0066] Without further elaboration, it is believed that one skilled in the art can, using the description herein, utilize the present invention to its fullest extent. The following specific embodiments are therefore to be construed as merely illustrative, and not constraining in any way whatsoever the remainder of the disclosure.

[0067] Selected Embodiments 1. This embodiment is a fluorobutene composition comprising E-1,1,1,4,4,4-hexafluoro-2-butene and a fluorinated compound selected from the group consisting of 1,1,1,2,4,4,4-heptafluorobutane, 1,1,1,3,3-pentafluoropropane, 2-chloro-1,1,1-trifluoroethane, E-1-chloro-3,3,3-trifluoropropene, Z-1-chloro-3,3,3-trifluoropropene, and 2-chloro-3,3,3-trifluoropropene, wherein the composition comprises at least 99% by weight E-1,1,1,4,4,4-hexafluoro-2-butene. 2. The composition of embodiment 1, wherein the fluorinated compound is present in an amount of 0.0001 to 0.9 wt.%. 3. The composition of embodiment 1, wherein the fluorinated compound is present in an amount of 0.0005 to 0.4% by weight. 4. The composition of embodiment 1, wherein the fluorinated compound is present in an amount of 0.005 to 0.2 wt.%. 5. The composition of any one of embodiments 1 to 4, further comprising a compound selected from the group consisting of vinyl chloride, 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, 1,1,1,2,4,4,4-heptafluoro-2-butene, and 1,1,1,4,4,4-hexafluorobutane. 6. The composition of any one of embodiments 1 to 5, further comprising Z-1,1,1,4,4,4-hexafluoro-2-butene. 7. The composition of embodiment 6, comprising 1,1,1,2,4,4,4-heptafluorobutane. 8. The composition of embodiment 6, comprising 2-chloro-1,1,1-trifluoroethane. 9. The composition of embodiment 6 comprising E-1-chloro-3,3,3-trifluoropropene, Z-1-chloro-3,3,3-trifluoropropene, 2-chloro-3,3,3-trifluoropropene, or a mixture of two or more thereof. 10. The composition of any one of embodiments 1-9, wherein the composition comprises less than 0.1% by weight of 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene. 11. The composition of any one of embodiments 1-9, wherein the composition contains less than 0.01% by weight of vinyl chloride. 12. The composition of any one of embodiments 1-9, wherein the composition comprises less than 0.1% by weight of 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene and less than 0.01% by weight of vinyl chloride. 13. This embodiment is a fluorobutene composition comprising E-1,1,1,4,4,4-hexafluoro-2-butene, Z-1,1,1,4,4,4-hexafluoro-2-butene, 1,1,1,2,4,4,4-heptafluorobutane, 2-chloro-1,1,1-trifluoroethane, E-1-chloro-3,3,3-trifluoropropene, Z-1-chloro-3,3,3-trifluoropropene, and 2-chloro-3,3,3-trifluoropropene, wherein the composition comprises greater than 99% by weight E-1,1,1,4,4,4-hexafluoro-2-butene. 14. This embodiment is a fluorobutene composition comprising E-1,1,1,4,4,4-hexafluoro-2-butene and at least two fluorinated compounds selected from the group consisting of 1,1,1,3,3-pentafluoropropane, 2-chloro-1,1,1-trifluoroethane, E-1-chloro-3,3,3-trifluoropropene, Z-1-chloro-3,3,3-trifluoropropene, 2-chloro-3,3,3-trifluoropropene, 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, and 1,1,1,2,4,4,4-heptafluoro-2-butene. 15. The composition comprising: 1,1,1,3,3-pentafluoropropane and 2-chloro-1,1,1-trifluoroethane, or 1,1,1,3,3-Pentafluoropropane and E-1-chloro-3,3,3-trifluoropropene, or 1,1,1,3,3-Pentafluoropropane and Z-1-chloro-3,3,3-trifluoropropene, or 1,1,1,3,3-pentafluoropropane and 2-chloro-3,3,3-trifluoropropene, or 1,1,1,3,3-Pentafluoropropane and 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, or 1,1,1,3,3-pentafluoropropane and 1,1,1,2,4,4,4-heptafluoro-2-butene, or 2-Chloro-1,1,1-trifluoroethane and E-1-chloro-3,3,3-trifluoropropene, or 2-chloro-1,1,1-trifluoroethane and Z-1-chloro-3,3,3-trifluoropropene, or 2-chloro-1,1,1-trifluoroethane and 2-chloro-3,3,3-trifluoropropene, or 2-Chloro-1,1,1-trifluoroethane and 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, or 2-Chloro-1,1,1-trifluoroethane and 1,1,1,2,4,4,4-heptafluoro-2-butene 16. The fluorobutene composition of embodiment 15, comprising: 16. This embodiment is a fluorobutene composition comprising E-1,1,1,4,4,4-hexafluoro-2-butene and at least three fluorinated compounds selected from the group consisting of 1,1,1,3,3-pentafluoropropane, 2-chloro-1,1,1-trifluoroethane, E-1-chloro-3,3,3-trifluoropropene, Z-1-chloro-3,3,3-trifluoropropene, 2-chloro-3,3,3-trifluoropropene, 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, and 1,1,1,2,4,4,4-heptafluoro-2-butene (1327mz). 17. The composition comprising: 1,1,1,3,3-pentafluoropropane, 2-chloro-1,1,1-trifluoroethane and Z-1-chloro-3,3,3-trifluoropropene, or 1,1,1,3,3-pentafluoropropane, 2-chloro-1,1,1-trifluoroethane and E-1-chloro-3,3,3-trifluoropropene, or 1,1,1,3,3-pentafluoropropane, 2-chloro-1,1,1-trifluoroethane and 2-chloro-3,3,3-trifluoropropene, or 1,1,1,3,3-pentafluoropropane, 2-chloro-1,1,1-trifluoroethane and 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, or 1,1,1,3,3-pentafluoropropane, 2-chloro-1,1,1-trifluoroethane and 1,1,1,2,4,4,4-heptafluoro-2-butene, or 1,1,1,3,3-pentafluoropropane, E-1-chloro-3,3,3-trifluoropropene and Z-1-chloro-3,3,3-trifluoropropene, or 1,1,1,3,3-pentafluoropropane, E-1-chloro-3,3,3-trifluoropropene and 2-chloro-3,3,3-trifluoropropene, or 1,1,1,3,3-Pentafluoropropane, E-1-chloro-3,3,3-trifluoropropene and 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, or 1,1,1,3,3-pentafluoropropane, E-1-chloro-3,3,3-trifluoropropene and 1,1,1,2,4,4,4-heptafluoro-2-butene, or 1,1,1,3,3-pentafluoropropane, Z-1-chloro-3,3,3-trifluoropropene and 2-chloro-3,3,3-trifluoropropene, or 1,1,1,3,3-pentafluoropropane, Z-1-chloro-3,3,3-trifluoropropene and 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, or 1,1,1,3,3-pentafluoropropane, Z-1-chloro-3,3,3-trifluoropropene and 1,1,1,2,4,4,4-heptafluoro-2-butene, or 2-chloro-1,1,1-trifluoroethane, E-1-chloro-3,3,3-trifluoropropene and Z-1-chloro-3,3,3-trifluoropropene, or 2-chloro-1,1,1-trifluoroethane, E-1-chloro-3,3,3-trifluoropropene and 2-chloro-3,3,3-trifluoropropene, or 2-Chloro-1,1,1-trifluoroethane, E-1-chloro-3,3,3-trifluoropropene and 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, or 2-Chloro-1,1,1-trifluoroethane, E-1-chloro-3,3,3-trifluoropropene and 1,1,1,2,4,4,4-heptafluoro-2-butene, or 2-chloro-1,1,1-trifluoroethane, Z-1-chloro-3,3,3-trifluoropropene and 2-chloro-3,3,3-trifluoropropene, or 2-Chloro-1,1,1-trifluoroethane, Z-1-chloro-3,3,3-trifluoropropene and 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, or 2-chloro-1,1,1-trifluoroethane, Z-1-chloro-3,3,3-trifluoropropene and 1,1,1,2,4,4,4-heptafluoro-2-butene, or 2-chloro-1,1,1-trifluoroethane, 2-chloro-3,3,3-trifluoropropene and 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, or 2-chloro-1,1,1-trifluoroethane, 2-chloro-3,3,3-trifluoropropene and 1,1,1,2,4,4,4-heptafluoro-2-butene, or 2-chloro-1,1,1-trifluoroethane, 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene and 1,1,1,2,4,4,4-heptafluoro-2-butene, or E-1-chloro-3,3,3-trifluoropropene, Z-1-chloro-3,3,3-trifluoropropene and 2-chloro-3,3,3-trifluoropropene, or E-1-chloro-3,3,3-trifluoropropene, Z-1-chloro-3,3,3-trifluoropropene and 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, or E-1-chloro-3,3,3-trifluoropropene, Z-1-chloro-3,3,3-trifluoropropene and 1,1,1,2,4,4,4-heptafluoro-2-butene, or E-1-chloro-3,3,3-trifluoropropene, 2-chloro-3,3,3-trifluoropropene and 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, or Z-1-chloro-3,3,3-trifluoropropene, 2-chloro-3,3,3-trifluoropropene and 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, or Z-1-Chloro-3,3,3-trifluoropropene, 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene and 1,1,1,2,4,4,4-heptafluoro-2-butene 17. The fluorobutene composition of embodiment 16, comprising: 18. The fluorobutene composition of any one of the preceding embodiments, further comprising a lubricant selected from the group consisting of mineral oils, such as paraffins, naphthenes, and aromatics, alkylaryls, such as linear and branched alkyl alkylbenzenes, synthetic paraffins, synthetic naphthenes, poly(alpha olefins), polyol esters, polyalkylene glycols, and polyvinyl ethers. 19. This embodiment is a method of forming a foam, comprising: (a) adding to a foamable composition the composition of any of embodiments 1-17; and (b) treating the foamable composition under conditions effective to form a foam. 20. This embodiment is a process for preparing a thermoplastic foam, comprising providing a foamable composition comprising a thermoplastic polymer and a blowing agent, wherein the blowing agent comprises the composition of any of embodiments 1-17. 21. This embodiment is a process for preparing a polyurethane or polyisocyanurate foam comprising reacting a polyisocyanate with an active hydrogen-containing compound in the presence of a blowing agent comprising the composition of any of embodiments 1-17 to obtain the foamed reaction product. 22. This embodiment is a process for producing an aerosol product comprising adding a composition according to any one of embodiments 1-17 to a formulation containing an active ingredient in an aerosol container, wherein the composition functions as a propellant. 23. This embodiment is directed to a process for treating a surface comprising providing a surface and contacting the surface with a treatment composition, the surface includes a treatable material deposited thereon; The process wherein the treatment composition comprises the fluorobutene composition according to any one of embodiments 1 to 17. 24. The process of embodiment 23, wherein the treating composition substantially dissolves the treatable material. 25. This embodiment is directed to a process for forming a composition comprising providing a solute and contacting the solute with a solvent, The process wherein the solvent comprises the fluorobutene composition of any one of embodiments 1 to 17. 26. This embodiment is a method for producing cooling comprising evaporating a composition described in any one of embodiments 1-18 in the vicinity of an object to be cooled and then condensing the composition. 27. This embodiment is a method for generating heat comprising condensing a composition described in any one of embodiments 1-18 in the vicinity of an object to be heated, and then evaporating the composition. 28. This embodiment is directed to a process for transferring heat comprising providing an article and contacting the article with a heat transfer medium; The process wherein the heat transfer medium comprises the fluorobutene composition according to any one of the first to eighteenth embodiments. 29. This embodiment is a process for converting heat to mechanical energy comprising heating a working fluid comprising the composition of any of embodiments 1-18 and then expanding the heated working fluid. 30. This embodiment includes an evaporator, a condenser, a compressor, an expansion device, and a heat transfer medium; A cooling system, wherein a heat transfer medium comprises the fluorobutene composition according to any one of the first to eighteenth embodiments. 31. This embodiment is a chiller apparatus comprising the fluorobutene composition of any one of embodiments 1-18. 32. The fluorobutene composition according to any one of embodiments 1 to 18 for use in a chiller appliance, preferably a medium temperature chiller appliance. 33. This embodiment is the use of the fluorobutene composition according to any one of embodiments 1 to 18 in a chiller appliance, preferably a medium temperature chiller appliance. 34. This embodiment is a method for producing cooling, comprising evaporating a composition described in any one of embodiments 1-18 in the vicinity of an object to be cooled, and then condensing the composition. 35. This embodiment is a cooling appliance, an air conditioner, or a heat pump appliance containing the composition of any one of embodiments 1 to 18, wherein the cooling appliance is preferably a fixed or mobile cooling appliance, and the air conditioner is preferably a mobile air conditioner, more preferably an automotive air conditioner. 36. This embodiment is a method for providing heating in a high temperature heat pump, comprising condensing in a condenser a vapor working fluid comprising the composition of any one of embodiments 1-18, thereby producing a liquid working fluid. 37. This embodiment is a method comprising: heating a working fluid using heat provided from a heat source; expanding the heated working fluid to reduce a pressure of the working fluid; and generating mechanical energy as the pressure of the working fluid is reduced, wherein the method uses a working fluid comprising the composition of any one of embodiments 1 to 17. EXAMPLES

[0068] Materials: The materials used to prepare the examples are either commercially available or can be prepared by known methods.

[0069] Examples 1-4. Preparation of E1336MZZ with Fluorinated Compounds E-HFO-1336mzz is prepared as follows: Inconel® pipe (0.5 inch (1.27 cm) OD, 10 inch (25.4 cm) length, 0.35 inch (0.89 cm wall thickness)) is the reactor and is packed with 6 cc of chromium catalyst. The catalyst is activated with HF. The reactor is operated at 80 psig. HCFC-343jfd and HF are fed in a 1 / 20 molar ratio. The contact time is 20 seconds.

[0070] Fluorobutene compositions containing E1336 with the fluorinated compounds listed in Table 2 are prepared using the amounts of additive compounds provided.

[0071] [Table 2]

[0072] Example 5. Performance test Compositions were prepared by mixing the components in the amounts listed and the cooling performance of these compositions was determined and is provided in Tables 3 and 4.

[0073] Cycle input parameters: Average evaporator temperature = 4.44℃ Evaporator superheat degree (K)=6 Suction line superheat degree (K)=0 Condenser average temperature = 37.78℃ Subcooling (K)=0 Compressor isentropic efficiency = 0.85 Compressor volumetric efficiency = 0.95 Glide is defined as the average of the evaporator glide and the condenser glide. The average dipole moment and GWP are calculated using a weighted average.

[0074] [Table 3]

[0075] [Table 4]

[0076] [Table 5]

[0077] [Table 6]

[0078] As can be seen from the performance in Tables 3 and 4, the compositions of the present invention exhibit improved energy efficiency (COP) versus pure E1336mzz.

Claims

1. 1. A fluorobutene composition comprising: E-1,1,1,4,4,4-hexafluoro-2-butene; and a fluorinated compound selected from the group consisting of 1,1,1,2,4,4,4-heptafluorobutane, 1,1,1,3,3-pentafluoropropane, 2-chloro-1,1,1-trifluoroethane, E-1-chloro-3,3,3-trifluoropropene, Z-1-chloro-3,3,3-trifluoropropene, and 2-chloro-3,3,3-trifluoropropene, wherein the composition comprises at least 99% by weight of E-1,1,1,4,4,4-hexafluoro-2-butene.

2. The composition of claim 1, wherein the fluorinated compound is present in an amount of 0.0001 to 0.9 weight percent.

3. The composition of claim 1, wherein the fluorinated compound is present in an amount of 0.0005 to 0.4 weight percent.

4. The composition of claim 1, wherein the fluorinated compound is present in an amount of 0.005 to 0.2 wt %.

5. The composition of any one of claims 1 to 4, further comprising a compound selected from the group consisting of vinyl chloride, 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, 1,1,1,2,4,4,4-heptafluoro-2-butene, and 1,1,1,4,4,4-hexafluorobutane.

6. The composition of any one of claims 1 to 5, further comprising Z-1,1,1,4,4,4-hexafluoro-2-butene.

7. The composition of claim 6 comprising 1,1,1,2,4,4,4-heptafluorobutane.

8. The composition of claim 6 comprising 2-chloro-1,1,1-trifluoroethane.

9. 7. The composition of claim 6 comprising E-1-chloro-3,3,3-trifluoropropene, Z-1-chloro-3,3,3-trifluoropropene, 2-chloro-3,3,3-trifluoropropene, or a mixture of two or more thereof.

10. The composition of any one of claims 1 to 9, wherein the composition comprises less than 0.1% by weight of 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene.

11. The composition of any one of claims 1 to 9, wherein the composition comprises less than 0.01% by weight of vinyl chloride.

12. The composition of any one of claims 1 to 9, wherein the composition comprises less than 0.1% by weight of 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene and less than 0.01% by weight of vinyl chloride.

13. 1. A fluorobutene composition comprising E-1,1,1,4,4,4-hexafluoro-2-butene, Z-1,1,1,4,4,4-hexafluoro-2-butene, 1,1,1,2,4,4,4-heptafluorobutane, 2-chloro-1,1,1-trifluoroethane, E-1-chloro-3,3,3-trifluoropropene, Z-1-chloro-3,3,3-trifluoropropene, and 2-chloro-3,3,3-trifluoropropene, wherein the composition comprises greater than 99% by weight of E-1,1,1,4,4,4-hexafluoro-2-butene.

14. 1. A fluorobutene composition comprising: E-1,1,1,4,4,4-hexafluoro-2-butene; and at least two fluorinated compounds selected from the group consisting of 1,1,1,3,3-pentafluoropropane, 2-chloro-1,1,1-trifluoroethane, E-1-chloro-3,3,3-trifluoropropene, Z-1-chloro-3,3,3-trifluoropropene, 2-chloro-3,3,3-trifluoropropene, 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, and 1,1,1,2,4,4,4-heptafluoro-2-butene.

15. The composition, 1,1,1,3,3-pentafluoropropane and 2-chloro-1,1,1-trifluoroethane, or 1,1,1,3,3-pentafluoropropane and E-1-chloro-3,3,3-trifluoropropene, or 1,1,1,3,3-pentafluoropropane and Z-1-chloro-3,3,3-trifluoropropene, or 1,1,1,3,3-pentafluoropropane and 2-chloro-3,3,3-trifluoropropene, or 1,1,1,3,3-pentafluoropropane and 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, or 1,1,1,3,3-pentafluoropropane and 1,1,1,2,4,4,4-heptafluoro-2-butene, or 2-chloro-1,1,1-trifluoroethane and E-1-chloro-3,3,3-trifluoropropene, or 2-chloro-1,1,1-trifluoroethane and Z-1-chloro-3,3,3-trifluoropropene, or 2-chloro-1,1,1-trifluoroethane and 2-chloro-3,3,3-trifluoropropene, or 2-chloro-1,1,1-trifluoroethane and 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, or 2-Chloro-1,1,1-trifluoroethane and 1,1,1,2,4,4,4-heptafluoro-2-butene 16. The fluorobutene composition of claim 15, comprising:

16. 1. A fluorobutene composition comprising: E-1,1,1,4,4,4-hexafluoro-2-butene; and at least three fluorinated compounds selected from the group consisting of 1,1,1,3,3-pentafluoropropane, 2-chloro-1,1,1-trifluoroethane, E-1-chloro-3,3,3-trifluoropropene, Z-1-chloro-3,3,3-trifluoropropene, 2-chloro-3,3,3-trifluoropropene, 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, and 1,1,1,2,4,4,4-heptafluoro-2-butene (1327mz).

17. The composition, 1,1,1,3,3-pentafluoropropane, 2-chloro-1,1,1-trifluoroethane and Z-1-chloro-3,3,3-trifluoropropene, or 1,1,1,3,3-pentafluoropropane, 2-chloro-1,1,1-trifluoroethane and E-1-chloro-3,3,3-trifluoropropene, or 1,1,1,3,3-pentafluoropropane, 2-chloro-1,1,1-trifluoroethane and 2-chloro-3,3,3-trifluoropropene, or 1,1,1,3,3-pentafluoropropane, 2-chloro-1,1,1-trifluoroethane and 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, or 1,1,1,3,3-pentafluoropropane, 2-chloro-1,1,1-trifluoroethane and 1,1,1,2,4,4,4-heptafluoro-2-butene, or 1,1,1,3,3-pentafluoropropane, E-1-chloro-3,3,3-trifluoropropene and Z-1-chloro-3,3,3-trifluoropropene, or 1,1,1,3,3-pentafluoropropane, E-1-chloro-3,3,3-trifluoropropene and 2-chloro-3,3,3-trifluoropropene, or 1,1,1,3,3-pentafluoropropane, E-1-chloro-3,3,3-trifluoropropene and 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, or 1,1,1,3,3-pentafluoropropane, E-1-chloro-3,3,3-trifluoropropene and 1,1,1,2,4,4,4-heptafluoro-2-butene, or 1,1,1,3,3-pentafluoropropane, Z-1-chloro-3,3,3-trifluoropropene and 2-chloro-3,3,3-trifluoropropene, or 1,1,1,3,3-pentafluoropropane, Z-1-chloro-3,3,3-trifluoropropene and 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, or 1,1,1,3,3-pentafluoropropane, Z-1-chloro-3,3,3-trifluoropropene and 1,1,1,2,4,4,4-heptafluoro-2-butene, or 2-chloro-1,1,1-trifluoroethane, E-1-chloro-3,3,3-trifluoropropene and Z-1-chloro-3,3,3-trifluoropropene, or 2-chloro-1,1,1-trifluoroethane, E-1-chloro-3,3,3-trifluoropropene and 2-chloro-3,3,3-trifluoropropene, or 2-chloro-1,1,1-trifluoroethane, E-1-chloro-3,3,3-trifluoropropene and 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, or 2-chloro-1,1,1-trifluoroethane, E-1-chloro-3,3,3-trifluoropropene and 1,1,1,2,4,4,4-heptafluoro-2-butene, or 2-chloro-1,1,1-trifluoroethane, Z-1-chloro-3,3,3-trifluoropropene and 2-chloro-3,3,3-trifluoropropene, or 2-chloro-1,1,1-trifluoroethane, Z-1-chloro-3,3,3-trifluoropropene and 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, or 2-chloro-1,1,1-trifluoroethane, Z-1-chloro-3,3,3-trifluoropropene and 1,1,1,2,4,4,4-heptafluoro-2-butene, or 2-chloro-1,1,1-trifluoroethane, 2-chloro-3,3,3-trifluoropropene and 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, or 2-chloro-1,1,1-trifluoroethane, 2-chloro-3,3,3-trifluoropropene and 1,1,1,2,4,4,4-heptafluoro-2-butene, or 2-chloro-1,1,1-trifluoroethane, 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene and 1,1,1,2,4,4,4-heptafluoro-2-butene, or E-1-chloro-3,3,3-trifluoropropene, Z-1-chloro-3,3,3-trifluoropropene and 2-chloro-3,3,3-trifluoropropene, or E-1-chloro-3,3,3-trifluoropropene, Z-1-chloro-3,3,3-trifluoropropene and 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, or E-1-chloro-3,3,3-trifluoropropene, Z-1-chloro-3,3,3-trifluoropropene and 1,1,1,2,4,4,4-heptafluoro-2-butene, or E-1-chloro-3,3,3-trifluoropropene, 2-chloro-3,3,3-trifluoropropene and 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, or Z-1-chloro-3,3,3-trifluoropropene, 2-chloro-3,3,3-trifluoropropene and 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene, or Z-1-chloro-3,3,3-trifluoropropene, 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene and 1,1,1,2,4,4,4-heptafluoro-2-butene 17. The fluorobutene composition of claim 16, comprising:

18. 18. The fluorobutene composition of any one of claims 1 to 17, further comprising a lubricant selected from the group consisting of mineral oils such as paraffins, naphthenes, and aromatics, alkylaryls such as linear and branched alkyl alkylbenzenes, synthetic paraffins, synthetic naphthenes, poly(alpha olefins), polyol esters, polyalkylene glycols, and polyvinyl ethers.

19. 18. A method of forming a foam comprising: (a) adding to a foamable composition the composition of any one of claims 1 to 17; and (b) treating the foamable composition under conditions effective to form a foam.

20. 18. A process for preparing a thermoplastic foam comprising providing a foamable composition comprising a thermoplastic polymer and a blowing agent, the blowing agent comprising the composition of any one of claims 1 to 17.

21. 18. A process for preparing a polyurethane or polyisocyanurate foam comprising reacting a polyisocyanate with an active hydrogen-containing compound in the presence of a blowing agent comprising the composition of any one of claims 1 to 17 to obtain said foamed reaction product.

22. 20. A process for producing an aerosol product, comprising adding a composition according to any one of claims 1 to 17 to a formulation comprising an active ingredient in an aerosol container, said composition acting as a propellant.

23. A process for treating a surface, comprising providing a surface and contacting the surface with a treatment composition, the surface includes a treatable material deposited thereon; A process wherein the treatment composition comprises the fluorobutene composition of any one of claims 1 to 17.

24. 24. The process of claim 23, wherein the treatment composition substantially dissolves the treatable material.

25. A process for forming a composition, comprising: providing a solute; and contacting the solute with a solvent; The process wherein the solvent comprises the fluorobutene composition of any one of claims 1 to 17.

26. 20. A method for producing cooling, comprising evaporating a composition according to any one of claims 1 to 18 in the vicinity of an object to be cooled, and thereafter condensing the composition.

27. 20. A method for producing heat, comprising condensing a composition according to any one of claims 1 to 18 in the vicinity of an object to be heated and then evaporating the composition.

28. 1. A process for transferring heat, comprising: providing an article; and contacting the article with a heat transfer medium; The process wherein the heat transfer medium comprises the fluorobutene composition of any one of claims 1 to 18.

29. 20. A process for converting heat into mechanical energy, comprising heating a working fluid comprising the composition of any one of claims 1 to 18 and then expanding the heated working fluid.

30. A cooling system comprising an evaporator, a condenser, a compressor, an expansion device, and a heat transfer medium; A cooling system, wherein the heat transfer medium comprises the fluorobutene composition of any one of claims 1 to 18.

31. Chiller equipment comprising the fluorobutene composition of any one of claims 1 to 18.

32. Fluorobutene composition according to any one of claims 1 to 18 for use in chiller equipment, preferably medium temperature chiller equipment.

33. Use of the fluorobutene composition according to any one of claims 1 to 18 in a chiller appliance, preferably a medium temperature chiller appliance.

34. 20. A method for producing cooling, comprising evaporating a composition according to any one of claims 1 to 18 in the vicinity of an object to be cooled, and thereafter condensing the composition.

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