Stabilized chlorofluoroethylenes

Abstract

The present application provides compositions comprising one or more chlorofluoroethenes and one or more stabilizer components, which can be used, for example, in refrigeration, air conditioning, or heat pump systems, and for reducing oxidation byproducts of one or more chlorofluoroethenes.

Description

Technical Field

[0001] This application provides compositions comprising one or more chlorofluoroethylene and one or more stabilizer components, which can be used, for example, in refrigeration, air conditioning, cooler or heat pump systems, and for reducing oxidative byproducts of chlorofluoroethylene. Background Technology

[0002] Vinyl chlorofluorocarbons (CFCs) are stable molecules under normal refrigeration conditions. However, they can be oxidized in the presence of trace amounts of air. The oxidation products, upon contact with moisture, produce HCl and HF, which can negatively impact systems using CFCs.

[0003] The industry requires stable refrigerants that meet an evolving regulatory environment. The regulatory landscape for refrigerants is constantly evolving, considering more than just the recently highlighted Ozone Depletion Potential (ODP) and Global Warming Potential (GWP). More specifically, refrigerant compositions are needed that not only meet low ODP standards and have low GWP, but also provide excellent performance across a wide range of applications and meet evolving regulatory standards.

[0004] This invention addresses certain problems associated with conventional refrigerants and provides a refrigerant containing stabilized chlorofluoroethylene that meets the evolving regulatory environment. Summary of the Invention

[0005] This application particularly provides a composition comprising one or more chlorofluoroethylenes and one or more stabilizer components selected from antioxidants, acid scavengers and metal stabilizers, or any combination thereof.

[0006] This application further provides a method for refrigeration, the method comprising condensing the composition provided herein and subsequently evaporating the composition in the vicinity of the subject to be cooled.

[0007] The present invention further provides a method for generating heat, the method comprising evaporating the composition provided herein and subsequently condensing the composition in the vicinity of the subject to be heated.

[0008] This application further provides air conditioning systems, heat pump systems, cooler systems, and refrigeration systems that include the compositions provided herein.

[0009] This application further provides a method for replacing an existing refrigerant in a refrigeration, air conditioning, or heat pump system with an alternative composition provided herein (e.g., an alternative composition comprising one or more chlorofluoroethylenes as provided herein), the method comprising providing the composition provided herein as a substitute for the existing refrigerant.

[0010] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. Methods and materials used in this invention are described herein; other suitable methods and materials known in the art may also be used. These materials, methods, and examples are illustrative only and are not intended to be limiting. All publications, patent applications, patents, sequences, database entries, and other references mentioned herein are incorporated herein by reference in their entirety. In the event of any conflict, this specification (including definitions) shall prevail. Detailed Implementation

[0011] There is a need to provide alternative compositions to reduce decomposition byproducts, such as those arising from the oxidation of vinylchlorofluorocarbons (e.g., one or more vinylchlorofluorocarbons provided herein). Therefore, this disclosure provides compositions (e.g., heat transfer compositions and / or refrigerant compositions) comprising one or more vinylchlorofluorocarbons and one or more stabilizer components. The compositions provided herein can reduce undesirable degradation byproducts, such as chlorides (e.g., hydrogen chloride), fluorides (e.g., hydrogen fluoride), and / or phosgene, arising from the decomposition (e.g., oxidation) of one or more vinylchlorofluorocarbons provided herein.

[0012] In some implementations, one or more chlorofluoroethylenes are independently selected from:

[0013] Trichlorofluoroethylene;

[0014] 1,1-Dichloro-2,2-difluoroethylene (CFO-1112a);

[0015] Chlorotrifluoroethylene (CFO-1113);

[0016] 1-Chloro-2,2-difluoroethylene (HCFO-1122);

[0017] E-1-Chloro-1,2-Difluoroethylene (E-HCFO-1122a);

[0018] Z-1-Chloro-1,2-Difluoroethylene (Z-HCFO-1122a);

[0019] E-1-Chloro-2-Fluoride (E-HCFO-1131);

[0020] Z-1-Chloro-2-Fluoride (Z-HCFO-1131);

[0021] 1-Chloro-1-fluoroethylene (HCFO-1131a);

[0022] 1,2-Dichloro-1-fluoroethylene (HCFO-1121); and

[0023] 1,1-Dichloro-2-fluoroethylene (HCFO-1121a).

[0024] In some embodiments, the chlorofluoroethylene provided herein is not E-1,2-dichloro-1,2-difluoroethylene, Z-1,2-dichloro-1,2-difluoroethylene, or a mixture thereof. In some embodiments, the chlorofluoroethylene provided herein is not E-1,2-dichloro-1,2-difluoroethylene. In some embodiments, the chlorofluoroethylene provided herein is not Z-1,2-dichloro-1,2-difluoroethylene. In some embodiments, the chlorofluoroethylene provided herein is not a mixture of E-1,2-dichloro-1,2-difluoroethylene and Z-1,2-dichloro-1,2-difluoroethylene.

[0025] In some embodiments, the composition comprises one type of chlorofluoroethylene (CFC) provided herein. In some embodiments, the composition comprises two types of CFCs provided herein. In some embodiments, the composition comprises three types of CFCs provided herein. In some embodiments, the composition comprises four types of CFCs provided herein.

[0026] In some embodiments, chlorofluoroethylene is selected from the group consisting of 1-chloro-2,2-difluoroethylene and 1-chloro-1,2-difluoroethylene.

[0027] In some embodiments, vinyl chloride is trichlorofluoroethylene. In some embodiments, vinyl chloride is 1,1-dichloro-2,2-difluoroethylene. In some embodiments, vinyl chloride is chlorotrifluoroethylene. In some embodiments, vinyl chloride is 1-chloro-2,2-difluoroethylene. In some embodiments, vinyl chloride is 1-chloro-1,2-difluoroethylene. In some embodiments, vinyl chloride is E-1-chloro-1,2-difluoroethylene. In some embodiments, vinyl chloride is Z-1-chloro-1,2-difluoroethylene. In some embodiments, vinyl chloride is E-1-chloro-2-fluoroethylene. In some embodiments, vinyl chloride is Z-1-chloro-2-fluoroethylene. In some embodiments, vinyl chloride is 1-chloro-1-fluoroethylene. In some embodiments, vinyl chloride is 1,2-dichloro-1-fluoroethylene. In some embodiments, vinyl chloride is 1,1-dichloro-2-fluoroethylene.

[0028] In some embodiments, one or more stabilizer components are each selected from antioxidants, acid scavengers and metal stabilizers, or any combination thereof.

[0029] In some embodiments, one or more stabilizer components are present in small amounts relative to the overall composition. In some embodiments, the amount of one or more stabilizer components in the disclosed composition is less than about 0.1 weight percent to up to about 5 weight percent of the total composition. In some embodiments of the invention, the additive is present in the disclosed composition in an amount from about 0.1 weight percent to about 5 weight percent of the total composition, or in an amount from about 0.1 weight percent to about 3.5 weight percent. The one or more stabilizer components selected for the disclosed composition are chosen based on the application and / or the requirements of individual equipment components or systems.

[0030] In some embodiments, each stabilizer component is independently present in the composition at concentrations from about 0.5 ppm to about 1500 ppm, for example, about 0.5 ppm, about 30 ppm, about 50 ppm, about 75 ppm, about 100 ppm, about 200 ppm, about 300 ppm, about 400 ppm, about 500 ppm, about 600 ppm, about 700 ppm, about 800 ppm, about 900 ppm, about 1000 ppm, about 1100 ppm, about 1200 ppm, about 1300 ppm, about 1400 ppm, about 1500 ppm, or within any of the foregoing concentrations. In some embodiments, each stabilizer component is independently present in the composition at a concentration from about 500 ppm to about 1000 ppm. In some embodiments, each stabilizer component is independently present in the composition at a concentration of about 500 ppm or about 1000 ppm. In some embodiments, each stabilizer component is independently present in the composition at a concentration of about 1000 ppm.

[0031] In some embodiments, the composition comprises one or more chlorofluoroethylenes provided herein and an antioxidant. In some embodiments, the composition comprises one or more chlorofluoroethylenes provided herein and an antioxidant. In some embodiments, the composition comprises 1-chloro-2,2-difluoroethylene and an antioxidant. In some embodiments, the composition comprises 1-chloro-1,2-difluoroethylene and an antioxidant. In some embodiments, the composition comprises (E)-1-chloro-1,2-difluoroethylene and an antioxidant. In some embodiments, the composition comprises (Z)-1-chloro-1,2-difluoroethylene and an antioxidant.

[0032] In some embodiments, the antioxidant is selected from terpenes, butylated hydroxytoluene, butylated hydroxyanisole, tert-butylhydroquinone, propyl 3,4,5-trihydroxybenzoate, 2-phenyl-2-propanol, 1-(2,4,5-trihydroxyphenyl)-1-butanone, 4-methoxyphenol, bisphenol methane derivatives, 2,2'-methylenebis(4-methyl-6-tert-butylphenol), and 2-isopropyl-5-methylphenol. In some embodiments, the antioxidant is selected from m-xylene, o-xylene, p-xylene, thymol, limonene (especially d-limonene), and pinene.

[0033] In some embodiments, the composition comprises one or more chlorofluoroethylenes provided herein and an acid scavenger. In some embodiments, the composition comprises 1-chloro-2,2-difluoroethylene and an acid scavenger. In some embodiments, the composition comprises 1-chloro-1,2-difluoroethylene and an acid scavenger. In some embodiments, the composition comprises (E)-1-chloro-1,2-difluoroethylene and an acid scavenger. In some embodiments, the composition comprises (Z)-1-chloro-1,2-difluoroethylene and an acid scavenger.

[0034] In some embodiments, the acid scavenger is selected from epoxides and amines. In some embodiments, the acid scavenger is an epoxide. In some embodiments, the acid scavenger is epoxide-butane. In some embodiments, the epoxide-butane is 1,2-epoxide-butane.

[0035] In some embodiments, the composition comprises one or more chlorofluoroethylenes and a metal stabilizer. In some embodiments, the composition comprises 1-chloro-2,2-difluoroethylene and a metal stabilizer. In some embodiments, the composition comprises 1-chloro-1,2-difluoroethylene and a metal stabilizer. In some embodiments, the composition comprises (E)-1-chloro-1,2-difluoroethylene and a metal stabilizer. In some embodiments, the composition comprises (Z)-1-chloro-1,2-difluoroethylene and a metal stabilizer.

[0036] In some embodiments, the metal stabilizer is selected from N,N'-bis(salicylic acid)-1,2-propanediamine and benzotriazole. In some embodiments, the metal stabilizer is N,N'-bis(salicylic acid)-1,2-propanediamine. In some embodiments, the metal stabilizer is benzotriazole.

[0037] In some embodiments, the composition comprises one or more chlorofluoroethylenes, an antioxidant, and an acid scavenger. In some embodiments, the composition comprises 1-chloro-2,2-difluoroethylene, an antioxidant, and an acid scavenger. In some embodiments, the composition comprises 1-chloro-1,2-difluoroethylene, an antioxidant, and an acid scavenger. In some embodiments, the composition comprises (E)-1-chloro-1,2-difluoroethylene, an antioxidant, and an acid scavenger. In some embodiments, the composition comprises (Z)-1-chloro-1,2-difluoroethylene, an antioxidant, and an acid scavenger.

[0038] In some embodiments, the composition comprises one or more chlorofluoroethylenes, 1,2-epoxybutane, and one or more antioxidants selected from the group consisting of m-xylene, o-xylene, p-xylene, thymol, d-limonene, and pinene. In some embodiments, the composition comprises 1-chloro-2,2-difluoroethylene, 1,2-epoxybutane, and one or more antioxidants selected from the group consisting of m-xylene, o-xylene, p-xylene, thymol, d-limonene, and pinene. In some embodiments, the composition comprises 1-chloro-1,2-difluoroethylene, 1,2-epoxybutane, and one or more antioxidants selected from the group consisting of m-xylene, o-xylene, p-xylene, thymol, d-limonene, and pinene. In some embodiments, the composition comprises (E)-1-chloro-1,2-difluoroethylene, 1,2-epoxybutane, and one or more antioxidants selected from the group consisting of m-xylene, o-xylene, p-xylene, thymol, d-limonene, and pinene. In some embodiments, the composition comprises (Z)-1-chloro-1,2-difluoroethylene, 1,2-epoxybutane, and one or more antioxidants selected from the group consisting of m-xylene, o-xylene, p-xylene, thymol, d-limonene, and pinene.

[0039] In some embodiments, the composition comprises one or more chlorofluoroethylene, m-xylene, and epoxide. In some embodiments, the composition comprises 1-chloro-2,2-difluoroethylene, m-xylene, and epoxide. In some embodiments, the composition comprises 1-chloro-1,2-difluoroethylene, m-xylene, and epoxide. In some embodiments, the composition comprises (E)-1-chloro-1,2-difluoroethylene, m-xylene, and epoxide. In some embodiments, the composition comprises (Z)-1-chloro-1,2-difluoroethylene, m-xylene, and epoxide.

[0040] In some embodiments, the composition comprises one or more chlorofluoroethylene, m-xylene, and 1,2-epoxybutane. In some embodiments, the composition comprises 1-chloro-2,2-difluoroethylene, m-xylene, and 1,2-epoxybutane. In some embodiments, the composition comprises 1-chloro-1,2-difluoroethylene, m-xylene, and 1,2-epoxybutane. In some embodiments, the composition comprises (E)-1-chloro-1,2-difluoroethylene, m-xylene, and 1,2-epoxybutane. In some embodiments, the composition comprises (Z)-1-chloro-1,2-difluoroethylene, m-xylene, and 1,2-epoxybutane.

[0041] In some embodiments, compositions comprising one or more chlorofluoroethylenes (e.g., 1-chloro-2,2-difluoroethylene, 1-chloro-1,2-difluoroethylene, (E)-1-chloro-1,2-difluoroethylene or (Z)-1-chloro-1,2-difluoroethylene), m-xylene and 1,2-epoxybutane contain about 0.5 ppm to about 1500 ppm of m-xylene, for example, about 0.5 ppm, about 30 ppm, about 50 ppm, about 75 ppm, about 100 ppm, about 200 ppm, about 300 ppm, about 400 ppm, about 500 ppm, about 600 ppm, about 700 ppm, about 800 ppm, about 900 ppm, about 1000 ppm, about 1100 ppm, about 1200 ppm, about 1300 ppm, about 1400 ppm, about 1500 ppm of m-xylene, or within any of the foregoing concentrations. In some embodiments, the composition contains about 900 ppm to about 1100 ppm of m-xylene. In some embodiments, the composition contains about 1000 ppm of m-xylene.

[0042] In some embodiments, compositions comprising one or more chlorofluoroethylenes (e.g., 1-chloro-2,2-difluoroethylene, 1-chloro-1,2-difluoroethylene, (E)-1-chloro-1,2-difluoroethylene, or (Z)-1-chloro-1,2-difluoroethylene), m-xylene, and 1,2-epoxybutane comprise about 0.5 ppm to about 1,500 ppm of 1,2-epoxybutane, for example, about 0.5 ppm, about 30 ppm, about 50 ppm, about 100 ppm, about 200 ppm, about 300 ppm, about 400 ppm, about 500 ppm, about 600 ppm, about 700 ppm, about 800 ppm, about 900 ppm, about 1000 ppm, about 1100 ppm, about 1200 ppm, about 1300 ppm, about 1400 ppm, or about 1500 ppm of 1,2-epoxybutane, or within any of the foregoing concentrations. In some embodiments, the composition comprises about 1000 ppm of m-xylene and about 1000 ppm of 1,2-epoxybutane.

[0043] In some embodiments, the composition comprises one or more of the chlorofluoroethylene, o-xylene, and epoxide provided herein. In some embodiments, the composition comprises 1-chloro-2,2-difluoroethylene, o-xylene, and epoxide. In some embodiments, the composition comprises 1-chloro-1,2-difluoroethylene, o-xylene, and epoxide. In some embodiments, the composition comprises (E)-1-chloro-1,2-difluoroethylene, o-xylene, and epoxide. In some embodiments, the composition comprises (Z)-1-chloro-1,2-difluoroethylene, o-xylene, and epoxide.

[0044] In some embodiments, the composition comprises one or more of the chlorofluoroethylene, o-xylene, and 1,2-epoxybutane provided herein. In some embodiments, the composition comprises one or more of the chlorofluoroethylene, o-xylene, and 1,2-epoxybutane. In some embodiments, the composition comprises 1-chloro-2,2-difluoroethylene, o-xylene, and 1,2-epoxybutane. In some embodiments, the composition comprises 1-chloro-1,2-difluoroethylene, o-xylene, and 1,2-epoxybutane. In some embodiments, the composition comprises (E)-1-chloro-1,2-difluoroethylene, o-xylene, and epoxybutane. In some embodiments, the composition comprises (Z)-1-chloro-1,2-difluoroethylene, o-xylene, and 1,2-epoxybutane.

[0045] In some embodiments, compositions comprising one or more chlorofluoroethylenes (e.g., 1-chloro-2,2-difluoroethylene, 1-chloro-1,2-difluoroethylene, (E)-1-chloro-1,2-difluoroethylene or (Z)-1-chloro-1,2-difluoroethylene), o-xylene, and 1,2-epoxybutane contain 0.5 ppm to about 1500 ppm of o-xylene, for example, about 0.5 ppm, about 30 ppm, about 50 ppm, about 75 ppm, about 100 ppm, about 200 ppm, about 300 ppm, about 400 ppm, about 500 ppm, about 600 ppm, about 700 ppm, about 800 ppm, about 900 ppm, about 1000 ppm, about 1100 ppm, about 1200 ppm, about 1300 ppm, about 1400 ppm, or about 1500 ppm of o-xylene, or within any of the foregoing concentrations. In some embodiments, the composition contains about 900 ppm to about 1100 ppm of o-xylene. In some embodiments, the composition contains about 1000 ppm of o-xylene.

[0046] In some embodiments, a composition comprising one or more chlorofluoroethylenes (e.g., 1-chloro-2,2-difluoroethylene, 1-chloro-1,2-difluoroethylene, (E)-1-chloro-1,2-difluoroethylene, or (Z)-1-chloro-1,2-difluoroethylene), o-xylene, and 1,2-epoxybutane comprises about 500 ppm to about 1500 ppm of 1,2-epoxybutane, for example, about 500 ppm, about 600 ppm, about 700 ppm, about 800 ppm, about 900 ppm, about 1000 ppm, about 1100 ppm, about 1200 ppm, about 1300 ppm, about 1400 ppm, or about 1500 ppm of 1,2-epoxybutane. In some embodiments, the composition comprises about 900 ppm to about 1100 ppm of 1,2-epoxybutane. In some embodiments, the composition comprises about 1000 ppm of 1,2-epoxybutane.

[0047] In some embodiments, a composition comprising one or more chlorofluoroethylenes (e.g., 1-chloro-2,2-difluoroethylene, 1-chloro-1,2-difluoroethylene, (E)-1-chloro-1,2-difluoroethylene or (Z)-1-chloro-1,2-difluoroethylene), o-xylene and 1,2-epoxybutane comprises about 1000 ppm of o-xylene and about 1000 ppm of 1,2-epoxybutane.

[0048] In some embodiments, the composition comprises one or more of the chlorofluoroethylene, p-xylene, and epoxide provided herein. In some embodiments, the composition comprises 1-chloro-2,2-difluoroethylene, p-xylene, and epoxide. In some embodiments, the composition comprises 1-chloro-1,2-difluoroethylene, p-xylene, and epoxide. In some embodiments, the composition comprises (E)-1-chloro-1,2-difluoroethylene, p-xylene, and epoxide. In some embodiments, the composition comprises (Z)-1-chloro-1,2-difluoroethylene, p-xylene, and epoxide.

[0049] In some embodiments, the composition comprises one or more chlorofluoroethylenes, p-xylene, and 1,2-epoxybutane. In some embodiments, the composition comprises 1-chloro-2,2-difluoroethylene, p-xylene, and 1,2-epoxybutane. In some embodiments, the composition comprises 1-chloro-1,2-difluoroethylene, p-xylene, and 1,2-epoxybutane. In some embodiments, the composition comprises (E)-1-chloro-1,2-difluoroethylene, p-xylene, and 1,2-epoxybutane. In some embodiments, the composition comprises (Z)-1-chloro-1,2-difluoroethylene, p-xylene, and 1,2-epoxybutane.

[0050] In some embodiments, compositions comprising one or more chlorofluoroethylenes (e.g., 1-chloro-2,2-difluoroethylene, 1-chloro-1,2-difluoroethylene, (E)-1-chloro-1,2-difluoroethylene or (Z)-1-chloro-1,2-difluoroethylene), p-xylene, and 1,2-epoxybutane contain about 0.5 ppm to about 1500 ppm of p-xylene, for example, about 0.5 ppm, about 30 ppm, about 50 ppm, about 75 ppm, about 100 ppm, about 200 ppm, about 300 ppm, about 400 ppm, about 500 ppm, about 600 ppm, about 700 ppm, about 800 ppm, about 900 ppm, about 1000 ppm, about 1100 ppm, about 1200 ppm, about 1300 ppm, about 1400 ppm, or about 1500 ppm of p-xylene, or within any of the foregoing concentrations. In some embodiments, the composition contains about 900 ppm to about 1100 ppm of p-xylene. In some embodiments, the composition contains about 1000 ppm of p-xylene.

[0051] In some embodiments, compositions comprising one or more chlorofluoroethylenes (e.g., 1-chloro-2,2-difluoroethylene, 1-chloro-1,2-difluoroethylene, (E)-1-chloro-1,2-difluoroethylene, or (Z)-1-chloro-1,2-difluoroethylene), p-xylene, and 1,2-epoxybutane contain about 500 ppm to about 1500 ppm of 1,2-epoxybutane, for example, about 500 ppm, about 600 ppm, about 700 ppm, about 800 ppm, about 900 ppm, about 1000 ppm, about 1100 ppm, about 1200 ppm, about 1300 ppm, about 1400 ppm, or about 1500 ppm of 1,2-epoxybutane. In some embodiments, the composition contains about 900 ppm to about 1100 ppm of 1,2-epoxybutane. In some embodiments, the composition contains about 1000 ppm of 1,2-epoxybutane.

[0052] In some embodiments, a composition comprising one or more chlorofluoroethylenes (e.g., 1-chloro-2,2-difluoroethylene, 1-chloro-1,2-difluoroethylene, (E)-1-chloro-1,2-difluoroethylene or (Z)-1-chloro-1,2-difluoroethylene), p-xylene and 1,2-epoxybutane comprises about 1,000 ppm of p-xylene and about 1,000 ppm of 1,2-epoxybutane.

[0053] In some embodiments, the composition comprises one or more chlorofluoroethylene, thymol, and epoxide. In some embodiments, the composition comprises 1-chloro-2,2-difluoroethylene, thymol, and epoxide. In some embodiments, the composition comprises 1-chloro-1,2-difluoroethylene, thymol, and epoxide. In some embodiments, the composition comprises (E)-1-chloro-1,2-difluoroethylene, thymol, and epoxide. In some embodiments, the composition comprises (Z)-1-chloro-1,2-difluoroethylene, thymol, and epoxide.

[0054] In some embodiments, the composition comprises one or more chlorofluoroethylenes, thymol, and 1,2-epoxybutane. In some embodiments, the composition comprises 1-chloro-2,2-difluoroethylene, thymol, and 1,2-epoxybutane. In some embodiments, the composition comprises 1-chloro-1,2-difluoroethylene, thymol, and 1,2-epoxybutane. In some embodiments, the composition comprises (E)-1-chloro-1,2-difluoroethylene, thymol, and 1,2-epoxybutane. In some embodiments, the composition comprises (Z)-1-chloro-1,2-difluoroethylene, thymol, and 1,2-epoxybutane.

[0055] In some embodiments, compositions comprising one or more chlorofluoroethylenes (e.g., 1-chloro-2,2-difluoroethylene, 1-chloro-1,2-difluoroethylene, (E)-1-chloro-1,2-difluoroethylene, or (Z)-1-chloro-1,2-difluoroethylene), thymol, and 1,2-epoxybutane contain about 100 ppm to about 1000 ppm of thymol, for example, about 100 ppm, about 200 ppm, about 300 ppm, about 400 ppm, about 500 ppm, about 600 ppm, about 700 ppm, about 800 ppm, about 900 ppm, or about 1000 ppm of thymol. In some embodiments, the composition contains about 400 ppm to about 600 ppm of thymol. In some embodiments, the composition contains about 500 ppm of thymol.

[0056] In some embodiments, compositions comprising one or more chlorofluoroethylenes (e.g., 1-chloro-2,2-difluoroethylene, 1-chloro-1,2-difluoroethylene, (E)-1-chloro-1,2-difluoroethylene or (Z)-1-chloro-1,2-difluoroethylene), thymol and 1,2-epoxybutane comprise about 0.5 ppm to about 1,500 ppm of 1,2-epoxybutane, for example, about 0.5 ppm, about 30 ppm, about 50 ppm, about 75 ppm, about 100 ppm, about 200 ppm, about 300 ppm, about 400 ppm, about 500 ppm, about 600 ppm, about 700 ppm, about 800 ppm, about 900 ppm, about 1000 ppm, about 1100 ppm, about 1200 ppm, about 1300 ppm, about 1400 ppm or about 1500 ppm of 1,2-epoxybutane, or within any of the foregoing concentrations. In some embodiments, the composition comprises about 900 ppm to about 1100 ppm of 1,2-epoxybutane. In some embodiments, the composition comprises about 1000 ppm of 1,2-epoxybutane.

[0057] In some embodiments, a composition comprising one or more chlorofluoroethylenes (e.g., 1-chloro-2,2-difluoroethylene, 1-chloro-1,2-difluoroethylene, (E)-1-chloro-1,2-difluoroethylene or (Z)-1-chloro-1,2-difluoroethylene), thymol and 1,2-epoxybutane comprises about 500 ppm of thymol and about 1000 ppm of 1,2-epoxybutane.

[0058] In some embodiments, the composition comprises one or more chlorofluoroethylene, pinene, and epoxide. In some embodiments, the composition comprises 1-chloro-2,2-difluoroethylene, pinene, and epoxide. In some embodiments, the composition comprises 1-chloro-1,2-difluoroethylene, pinene, and epoxide. In some embodiments, the composition comprises (E)-1-chloro-1,2-difluoroethylene, pinene, and epoxide. In some embodiments, the composition comprises (Z)-1-chloro-1,2-difluoroethylene, pinene, and epoxide.

[0059] In some embodiments, the composition comprises one or more of the chlorofluoroethylene, pinene, and 1,2-epoxybutane provided herein. In some embodiments, the composition comprises 1-chloro-2,2-difluoroethylene, pinene, and 1,2-epoxybutane. In some embodiments, the composition comprises 1-chloro-1,2-difluoroethylene, pinene, and 1,2-epoxybutane. In some embodiments, the composition comprises (E)-1-chloro-1,2-difluoroethylene, pinene, and 1,2-epoxybutane. In some embodiments, the composition comprises (Z)-1-chloro-1,2-difluoroethylene, pinene, and 1,2-epoxybutane.

[0060] In some embodiments, compositions comprising one or more chlorofluoroethylenes (e.g., 1-chloro-2,2-difluoroethylene, 1-chloro-1,2-difluoroethylene, (E)-1-chloro-1,2-difluoroethylene, or (Z)-1-chloro-1,2-difluoroethylene), pinene, and 1,2-epoxybutane contain about 100 ppm to about 1000 ppm of pinene, such as about 100 ppm, about 200 ppm, about 300 ppm, about 400 ppm, about 500 ppm, about 600 ppm, about 700 ppm, about 800 ppm, about 900 ppm, or about 1000 ppm of pinene. In some embodiments, the composition contains about 400 ppm to about 600 ppm of pinene. In some embodiments, the composition contains about 500 ppm of pinene.

[0061] In some embodiments, compositions comprising one or more chlorofluoroethylenes (e.g., 1-chloro-2,2-difluoroethylene, 1-chloro-1,2-difluoroethylene, (E)-1-chloro-1,2-difluoroethylene or (Z)-1-chloro-1,2-difluoroethylene), pinene and 1,2-epoxybutane comprise about 0.5 ppm to about 1,500 ppm of 1,2-epoxybutane, for example, about 0.5 ppm, about 30 ppm, about 50 ppm, about 75 ppm, about 100 ppm, about 200 ppm, about 300 ppm, about 400 ppm, about 500 ppm, about 600 ppm, about 700 ppm, about 800 ppm, about 900 ppm, about 1000 ppm, about 1100 ppm, about 1200 ppm, about 1300 ppm, about 1400 ppm or about 1500 ppm of 1,2-epoxybutane, or within any of the foregoing concentrations. In some embodiments, the composition comprises about 900 ppm to about 1100 ppm of 1,2-epoxybutane. In some embodiments, the composition comprises about 1000 ppm of 1,2-epoxybutane.

[0062] In some embodiments, a composition comprising one or more chlorofluoroethylenes (e.g., 1-chloro-2,2-difluoroethylene, 1-chloro-1,2-difluoroethylene, (E)-1-chloro-1,2-difluoroethylene or (Z)-1-chloro-1,2-difluoroethylene), pinene and 1,2-epoxybutane contains about 500 ppm pinene and about 1000 ppm 1,2-epoxybutane.

[0063] In some embodiments, the composition comprises one or more chlorofluoroethylenes, d-limonene, and epoxide. In some embodiments, the composition comprises 1-chloro-2,2-difluoroethylene, d-limonene, and epoxide. In some embodiments, the composition comprises 1-chloro-1,2-difluoroethylene, d-limonene, and epoxide. In some embodiments, the composition comprises (E)-1-chloro-1,2-difluoroethylene, d-limonene, and epoxide. In some embodiments, the composition comprises (Z)-1-chloro-1,2-difluoroethylene, d-limonene, and epoxide.

[0064] In some embodiments, the composition comprises one or more of the chlorofluoroethylene, d-limonene, and 1,2-epoxybutane provided herein. In some embodiments, the composition comprises 1-chloro-2,2-difluoroethylene, d-limonene, and 1,2-epoxybutane. In some embodiments, the composition comprises 1-chloro-1,2-difluoroethylene, d-limonene, and 1,2-epoxybutane. In some embodiments, the composition comprises (E)-1-chloro-1,2-difluoroethylene, d-limonene, and 1,2-epoxybutane. In some embodiments, the composition comprises (Z)-1-chloro-1,2-difluoroethylene, d-limonene, and 1,2-epoxybutane.

[0065] In some embodiments, compositions comprising one or more chlorofluoroethylenes (e.g., 1-chloro-2,2-difluoroethylene, 1-chloro-1,2-difluoroethylene, (E)-1-chloro-1,2-difluoroethylene, or (Z)-1-chloro-1,2-difluoroethylene), d-limonene, and 1,2-epoxybutane contain about 100 ppm to about 1000 ppm of d-limonene, for example, about 100 ppm, about 200 ppm, about 300 ppm, about 400 ppm, about 500 ppm, about 600 ppm, about 700 ppm, about 800 ppm, about 900 ppm, or about 1000 ppm of d-limonene. In some embodiments, the composition contains about 400 ppm to about 600 ppm of d-limonene. In some embodiments, the composition contains about 500 ppm of d-limonene.

[0066] In some embodiments, compositions comprising one or more chlorofluoroethylenes (e.g., 1-chloro-2,2-difluoroethylene, 1-chloro-1,2-difluoroethylene, (E)-1-chloro-1,2-difluoroethylene or (Z)-1-chloro-1,2-difluoroethylene), d-limonene, and 1,2-epoxybutane comprise about 0.5 ppm to about 1,500 ppm of 1,2-epoxybutane, for example, about 0.5 ppm, about 30 ppm, about 50 ppm, about 75 ppm, about 100 ppm, about 200 ppm, about 300 ppm, about 400 ppm, about 500 ppm, about 600 ppm, about 700 ppm, about 800 ppm, about 900 ppm, about 1000 ppm, about 1100 ppm, about 1200 ppm, about 1300 ppm, about 1400 ppm, or about 1500 ppm of 1,2-epoxybutane, or within any of the foregoing concentrations. In some embodiments, the composition comprises about 900 ppm to about 1100 ppm of 1,2-epoxybutane. In some embodiments, the composition comprises about 1000 ppm of 1,2-epoxybutane.

[0067] In some embodiments, compositions comprising one or more chlorofluoroethylenes (e.g., 1-chloro-2,2-difluoroethylene, 1-chloro-1,2-difluoroethylene, (E)-1-chloro-1,2-difluoroethylene, or (Z)-1-chloro-1,2-difluoroethylene), d-limonene, and 1,2-epoxybutane comprise about 500 ppm of d-limonene and about 1000 ppm of 1,2-epoxybutane. In some embodiments, compositions provided herein comprise one or more additional compounds selected from the following:

[0068] (E)-1-chloro-1,2-difluoroethylene (E-1122a);

[0069] (Z)-1-chloro-1,2-difluoroethylene (Z-1122a);

[0070] 1,2-Dichloro-1,1-difluoroethane (R-132b);

[0071] 2-Chloro-1,1,1-trifluoroethane (R-133a); and

[0072] 1-Chloro-1,2,2,2-Tetrafluoroethane (R-124).

[0073] In some embodiments, the compositions provided herein comprise one or more additional compounds selected from the following:

[0074] 1-Chloro-2,2-difluoroethylene (1122);

[0075] (E)-1,2-dichloro-1,2-difluoroethylene (E-1112);

[0076] (Z)-1,2-Dichloro-1,2-difluoroethylene (Z-1112);

[0077] 1-Chloro-1,2,2-trifluoroethane (R-133);

[0078] Chlorotrifluoroethylene (R-1113); and

[0079] 1-Chloro-2,2,2-trifluoroethane (R-133a).

[0080] In some embodiments, the compositions provided herein consist essentially of one or more chlorofluoroethylenes (e.g., 1-chloro-2,2-difluoroethylene, 1-chloro-1,2-difluoroethylene, (E)-1-chloro-1,2-difluoroethylene or (Z)-1-chloro-1,2-difluoroethylene) and one or more stabilizer components selected from antioxidants, acid scavengers and metal stabilizers, or any combination thereof.

[0081] In some embodiments, the compositions provided herein consist of one or more chlorofluoroethylenes (e.g., 1-chloro-2,2-difluoroethylene, 1-chloro-1,2-difluoroethylene, (E)-1-chloro-1,2-difluoroethylene or (Z)-1-chloro-1,2-difluoroethylene) and one or more stabilizer components selected from antioxidants, acid scavengers and metal stabilizers, or any combination thereof.

[0082] In some embodiments, the compositions provided herein consist essentially of: one or more chlorofluoroethylenes (e.g., 1-chloro-2,2-difluoroethylene, 1-chloro-1,2-difluoroethylene, (E)-1-chloro-1,2-difluoroethylene or (Z)-1-chloro-1,2-difluoroethylene) provided herein and one or more stabilizer components selected from antioxidants, acid scavengers and metal stabilizers, or any combination thereof; and one or more additional compounds.

[0083] In some embodiments, the compositions provided herein consist essentially of: 1-chloro-2,2-difluoroethylene and one or more stabilizer components selected from antioxidants, acid scavengers, and metal stabilizers, or any combination thereof; and one or more additional compounds selected from:

[0084] (E)-1-chloro-1,2-difluoroethylene (E-1122a);

[0085] (Z)-1-chloro-1,2-difluoroethylene (Z-1122a);

[0086] 1,2-Dichloro-1,1-difluoroethane (R-132b);

[0087] 2-Chloro-1,1,1-trifluoroethane (R-133a); and

[0088] 1-Chloro-1,2,2,2-Tetrafluoroethane (R-124).

[0089] In some embodiments, the compositions provided herein consist essentially of: 1-chloro-2,2-difluoroethylene, 1,2-epoxybutane, and one or more antioxidants selected from the group consisting of m-xylene, o-xylene, p-xylene, thymol, and pinene; and one or more additional compounds selected from the group consisting of:

[0090] (E)-1-chloro-1,2-difluoroethylene (E-1122a);

[0091] (Z)-1-chloro-1,2-difluoroethylene (Z-1122a);

[0092] 1,2-Dichloro-1,1-difluoroethane (R-132b);

[0093] 2-Chloro-1,1,1-trifluoroethane (R-133a); and

[0094] 1-Chloro-1,2,2,2-Tetrafluoroethane (R-124).

[0095] In some embodiments, the compositions provided herein consist of: one or more chlorofluoroethylenes and one or more stabilizer components selected from antioxidants, acid scavengers and metal stabilizers, or any combination thereof; and one or more additional compounds.

[0096] In some embodiments, the compositions provided herein comprise: 1-chloro-2,2-difluoroethylene and one or more stabilizer components selected from antioxidants, acid scavengers, and metal stabilizers, or any combination thereof; and one or more additional compounds selected from the following:

[0097] (E)-1-chloro-1,2-difluoroethylene (E-1122a);

[0098] (Z)-1-chloro-1,2-difluoroethylene (Z-1122a);

[0099] 1,2-Dichloro-1,1-difluoroethane (R-132b);

[0100] 2-Chloro-1,1,1-trifluoroethane (R-133a); and

[0101] 1-Chloro-1,2,2,2-Tetrafluoroethane (R-124).

[0102] In some embodiments, the compositions provided herein comprise: 1-chloro-2,2-difluoroethylene, 1,2-epoxybutane, and one or more antioxidants selected from the group consisting of m-xylene, o-xylene, p-xylene, thymol, and pinene; and one or more additional compounds selected from the group consisting of:

[0103] (E)-1-chloro-1,2-difluoroethylene (E-1122a);

[0104] (Z)-1-chloro-1,2-difluoroethylene (Z-1122a);

[0105] 1,2-Dichloro-1,1-difluoroethane (R-132b);

[0106] 2-Chloro-1,1,1-trifluoroethane (R-133a); and

[0107] 1-Chloro-1,2,2,2-Tetrafluoroethane (R-124).

[0108] In some embodiments, the compositions provided herein comprise: 1-chloro-1,2-difluoroethylene and one or more stabilizer components selected from antioxidants, acid scavengers, and metal stabilizers, or any combination thereof; and one or more additional compounds selected from the following:

[0109] 1-Chloro-2,2-difluoroethylene (1122);

[0110] (E)-1,2-dichloro-1,2-difluoroethylene (E-1112);

[0111] (Z)-1,2-Dichloro-1,2-difluoroethylene (Z-1112);

[0112] 1-Chloro-1,2,2-trifluoroethane (R-133);

[0113] Chlorotrifluoroethylene (R-1113); and

[0114] 1-Chloro-2,2,2-trifluoroethane (R-133a).

[0115] In some embodiments, the compositions provided herein comprise: 1-chloro-1,2-difluoroethylene, 1,2-epoxybutane, and one or more antioxidants selected from the group consisting of m-xylene, o-xylene, p-xylene, thymol, and pinene; and one or more additional compounds selected from the group consisting of:

[0116] 1-Chloro-2,2-difluoroethylene (1122);

[0117] (E)-1,2-dichloro-1,2-difluoroethylene (E-1112);

[0118] (Z)-1,2-Dichloro-1,2-difluoroethylene (Z-1112);

[0119] 1-Chloro-1,2,2-trifluoroethane (R-133);

[0120] Chlorotrifluoroethylene (R-1113); and

[0121] 1-Chloro-2,2,2-trifluoroethane (R-133a).

[0122] In some embodiments, it has been found that the compositions of the present invention are free of or substantially free of Class A fluorinated substances, and that the degradation products of the compositions are free of or substantially free of Class A fluorinated substances.

[0123] In one embodiment, as used herein, “Class A fluorinated substance” includes any substance that: (i) contains at least one perfluoromethyl (-CF3) or perfluoromethylene (-CF2-) carbon atom (without any H / Cl / Br / I bonded to that carbon atom); and (ii) Complies with Annex XIII (Section 1.1.1) of the EU REACH Regulation ( https: / / reachonline.eu / reach / en / annex-xiii-1-1.1-1.1.1.html, as accessed on May 2, 2023 The provisions of the document and the attached XV restriction report dated March 22, 2023 () are as follows. https: / / echa.europa.eu / documents / 10162 / f605d4b5-7c17-7414- 8823-b49b9fd43aea, as accessed on May 2, 2023. The persistence standards in soil / sediments and water cited in [reference needed] are incorporated herein by reference. In one embodiment, Class A fluorides include, but are not limited to, trifluoroacetic acid (TFA).

[0124] In another embodiment, as used herein, “Class A fluorinated substance” includes any substance having a concentration of ≤250 Pa*m. 3 Henry's Law constant / mol and It contains at least one perfluoromethyl (-CF3) or perfluoromethylene (-CF2-) carbon atom (without any H / Cl / Br / I atoms attached to that carbon atom). In one embodiment, Class A fluorinated substances include, but are not limited to, TFA.

[0125] Therefore, according to some embodiments, the compositions of the present invention comprising, consisting of, or substantially consisting of stabilized vinyl chloride, are free from or substantially free from Class A fluorinated substances, such as TFA. In one embodiment, the term “free from” as used herein with respect to the presence of Class A fluorinated substances in the compositions of the present invention means that the amount of such substances in these compositions is sufficiently low to be undetectable (including, but not limited to, 0%) when measured by: gas chromatography using a flame ionization detector, gas chromatography analyzing gas or liquid samples using a mass spectrometer, and / or ion chromatography analyzing water samples after bubbling with a hot fluid passed through water. Such methods are well known to those skilled in the art. In one embodiment, the term "substantially free" as used herein with respect to the presence of Class A fluorinated substances in the compositions of the invention means that the amount of such substances in the composition is >0 wt.% and ≤5 wt.%, or >0 wt.% and ≤4 wt.%, or >0 wt.% and ≤3 wt.%, or >0 wt.% and ≤2 wt.%, or >0 wt.% and ≤1 wt.%, and all values ​​and ranges between these values, when measured by: gas chromatography (GC) techniques, such as gas chromatography (GC) or GC-MS using a flame ionization or electron capture detector (GC / MS method); ion chromatography (IC) or ion chromatography-mass spectrometry (IC-MS); or high performance liquid chromatography (HPLC) or high performance liquid chromatography-mass spectrometry (HPLC-MS). TFA analytical standards are available for gas chromatography or ion chromatography and are commercially available, for example, from Sigma Aldrich. In some implementations, the stabilized 1,2-dichloro-1,2-difluoroethylene is free of Class A fluorinated substances, meaning that these substances are undetectable by the methods and techniques described herein.

[0126] Furthermore, in some embodiments, the degradation products of such compositions of the present invention, comprising, or substantially comprising stabilized vinylchlorofluoroethylene, are free from or substantially free from Class A fluorinated substances, such as TFA. In one embodiment, the term “free from” as used herein with respect to the formation of Class A fluorinated substances by the compositions of the present invention means that the theoretical molar yield of such substance in the environmental media of air, soil / sediment, and water generated during the tropospheric degradation of these compositions is sufficiently low to be undetectable (including, but not limited to, 0%) by means of: GC techniques, such as GC or GC / MS methods using flame ionization or electron capture detectors; IC or IC-MS techniques; or HPLC or HPLC-MS techniques. In one embodiment, the term "substantially free" as used herein with respect to the formation of Class A fluorinated substances from the compositions of the present invention means, when measured by: a theoretical molar yield of such substances in the environmental media of air, soil / sediment, and water generated during the tropospheric degradation of the composition >0% and ≤5%, or >0% and ≤4%, or >0% and ≤3%, or >0% and ≤2%, or >0% and ≤1%, and all values ​​and ranges between therewith; GC techniques, such as GC or GC / MS methods using flame ionization or electron capture detectors; IC or IC-MS techniques; or HPLC or HPLC-MS techniques. In some embodiments, the degradation products of such compositions of the present invention, comprising, or substantially comprising stabilized 1,2-dichloro-1,2-difluoroethylene, are free of Class A fluorinated substances, such as TFA, meaning that these substances are undetectable by the methods and techniques described herein.

[0127] As used herein, the terms “comprising,” “including,” “having,” or any other variations thereof are intended to cover non-exclusive inclusion. For example, a process, method, article of manufacture, or apparatus that includes a list of elements is not necessarily limited to those components, but may include other elements not expressly listed or other elements inherent to such a process, method, article of manufacture, or apparatus. Furthermore, unless expressly stated to the contrary, “or” means inclusive or not exclusive. For example, any of the following satisfy conditions A or B: 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).

[0128] As used herein, the term "substantially composed of" is used to define a composition or method that includes, in addition to the materials, steps, features, components, or elements explicitly disclosed, such additional materials, steps, features, components, or elements, provided that these additionally included materials, steps, features, components, or elements do not materially affect the essential and novel features of the claimed invention, particularly the mode of action for achieving the desired results of any of the methods of the invention. The meaning of the term "substantially composed of" falls between "comprising" and "composed of".

[0129] Additionally, the term "a kind" is used to describe the elements and components described herein. This is done merely for convenience and to provide a general meaning regarding the scope of the invention. This description should be interpreted as including a kind or at least one kind, and unless otherwise clearly different, the singular expression also covers the plural reference.

[0130] As used herein, the term “about” means taking into account variations attributable to experimental error (e.g., a caliber value plus or minus approximately 10%). Whether or not the term is explicitly used, all measurements reported herein should be understood to be modified by the term “about” unless otherwise explicitly stated.

[0131] When a quantity, concentration, or other value or parameter is given as a range, preferred range, or list of preferred upper and / or lower limits, whether or not the range is disclosed individually, it should be understood as specifically disclosing the entire range formed by any pair of any upper or preferred value with any lower or preferred value. When a range of a numerical value is given herein, unless otherwise stated, the range is intended to include its endpoints and all integers and fractions falling within that range.

[0132] Cooling capacity (sometimes called refrigeration capacity) is a term used to define the enthalpy change of a refrigerant or working fluid per unit mass of refrigerant or working fluid circulating in an evaporator. Volumetric cooling capacity refers to the amount of heat removed by the refrigerant or working fluid per unit volume of refrigerant vapor leaving the evaporator. Cooling capacity is used to evaluate the ability of a refrigerant, working fluid, or heat transfer composition to cool. Therefore, the higher the volumetric cooling capacity of the working fluid, the greater the rate of cooling that can be achieved at the evaporator for a given compressor's maximum volumetric flow rate. Cooling rate refers to the amount of heat removed by the refrigerant in the evaporator per unit time.

[0133] Similarly, volumetric heating capacity is a term that defines the amount of heat provided by the refrigerant or working fluid in the condenser per unit volume of refrigerant or working fluid vapor entering the compressor. The higher the volumetric heating capacity of the refrigerant or working fluid, the greater the rate of heating that can be produced at the condenser at the maximum volumetric flow rate achievable by a given compressor.

[0134] The coefficient of performance (COP) is the amount of heat removed from the evaporator divided by the energy required to operate the compressor. A higher COP indicates higher energy efficiency. COP is directly related to the energy efficiency ratio (EER), which is an efficiency rating for refrigeration or air conditioning equipment under a specific set of internal and external temperatures.

[0135] As used herein, a heat transfer medium comprises a composition for carrying heat from a heat source to a radiator. For example, heat can travel from the body to be cooled to a cooler evaporator, or from a cooler condenser to a cooling tower or other structure from which heat can be dissipated to the surrounding environment.

[0136] As used herein, a working fluid or refrigerant comprises a compound or mixture of compounds (e.g., the composition provided herein) that acts to transfer heat in a cycle, wherein the working fluid undergoes a phase change from liquid to gas and returns to liquid in repeated cycles.

[0137] Subcooling occurs when the temperature of a liquid drops below its saturation point at a given pressure. The saturation point is the temperature at which a vapor composition completely condenses into a liquid (also known as the bubble point). However, subcooling continues to cool the liquid to an even lower temperature at a given pressure. Net cooling capacity can be increased by cooling the liquid below its saturation temperature. Subcooling thus improves the cooling capacity and energy efficiency of a system. Subcooling is the amount of cooling below the saturation temperature (measured in degrees Celsius) or the degree to which a liquid composition is cooled below its saturation temperature.

[0138] The term "superheat" defines the degree to which a vapor composition is heated above its saturated vapor temperature. The saturated vapor temperature is the temperature at which the first drop of liquid forms if the vapor composition is cooled; it is also known as the "dew point".

[0139] The compositions provided herein can act as a working fluid for carrying heat from a heat source to a radiator. Such heat transfer compositions can also be used as a refrigerant in a cycle, wherein the fluid undergoes a phase change; that is, from liquid to gas and back, or vice versa. Examples of heat transfer systems include, but are not limited to, air conditioners, refrigerators, freezers, heat pumps, water-cooled coolers, flooded evaporator coolers, direct expansion coolers, walk-in coolers, high-temperature heat pumps, portable refrigerators, portable air conditioning units, immersion cooling systems, data center cooling systems, and combinations thereof. Therefore, this application provides heat transfer systems (e.g., heat transfer devices) as described herein, which include the compositions provided herein. In some embodiments, the compositions provided herein can be used as a working fluid in a heat transfer device (e.g., a working fluid for refrigeration or heating applications). In some embodiments, the compositions provided herein can be used in devices or systems including high-temperature heat pumps. In some embodiments, the high-temperature heat pump includes a centrifugal compressor. In some embodiments, the compositions provided herein can be used in devices or systems including cooler devices. In some embodiments, the compositions provided herein can be used in devices or systems including centrifugal cooler devices. In some embodiments, the compositions provided herein can be used in devices or systems including screw or scroll cooler units. In some embodiments, the compositions provided herein can be used in centrifugal high-temperature heat pumps.

[0140] Mechanical vapor compression refrigeration systems, air conditioning systems, and heat pump systems include an evaporator, compressor, condenser, and expansion unit. The refrigeration cycle reuses the refrigerant in multiple steps, producing a cooling effect in one step and a heating effect in different steps. This cycle can be described as follows: Liquid refrigerant enters the evaporator through the expansion unit, and the liquid refrigerant boils in the evaporator by absorbing heat from the environment at a low temperature, forming a gas and cooling. Typically, air or a heat transfer fluid flows through or around the evaporator to transfer the cooling effect caused by the evaporation of the refrigerant in the evaporator to the body being cooled. The low-pressure gas enters the compressor, where it is compressed to increase its pressure and temperature. The higher-pressure (compressed) gaseous refrigerant then enters the condenser, where it condenses and releases its heat to the environment. The refrigerant returns to the expansion unit, through which the liquid expands from the higher pressure level in the condenser to the lower pressure level in the evaporator, thus repeating the cycle.

[0141] A subject to be cooled or heated can be defined as any space, location, object, or subject to which cooling or heating is desired. Examples include spaces (open or enclosed) that require air conditioning, cooling, or heating, such as rooms, apartments, or buildings such as apartment buildings, university dormitories, townhouses or other row houses or single-family homes, hospitals, office buildings, supermarkets, college or university classrooms or administrative buildings, and passenger compartments of cars or trucks. Furthermore, a subject to be cooled can include electronic equipment such as computer equipment, central processing units (CPUs), data centers, server clusters, and personal computers.

[0142] The term "nearby" means that in a refrigerant-containing system, the evaporator is located within or adjacent to the body to be cooled, such that air moving through the evaporator will move into or around the body to be cooled. In methods for heating, "nearby" means that in a refrigerant-containing system, the condenser is located within or adjacent to the body to be heated, such that air moving through the evaporator will move into or around the body to be heated. For example, in some embodiments, for heat transfer, "nearby" may mean that the body to be cooled is directly immersed in the heat transfer composition, or that a tube containing the heat transfer composition is inserted into and surrounds the body internally and extends to the exterior of the electronic device.

[0143] Exemplary refrigeration systems include, but are not limited to, devices comprising: commercial, industrial, or residential refrigerators and freezers, ice makers, freestanding coolers and freezers, vending machines, flooded evaporator coolers, direct expansion coolers, water-cooled coolers, centrifugal coolers, screw coolers, scroll coolers, walk-in and pick-and-place coolers and freezers, and combined systems. In some embodiments, the compositions provided herein can be used in supermarket refrigeration systems. Furthermore, stationary applications may utilize a secondary loop system that uses a primary refrigerant for cooling at one location, with the cooling capacity transferred to a remote location via a secondary heat transfer fluid.

[0144] In some embodiments, the compositions provided herein can be used in mobile heat transfer systems, including refrigeration, air conditioning, cooler, or heat pump systems or devices. In some embodiments, the compositions can be used in stationary heat transfer systems, including refrigeration, air conditioning, cooler, or heat pump systems or devices.

[0145] As used herein, a mobile refrigeration, air conditioning, cooler, or heat pump system refers to any refrigeration, air conditioning, or heat pump unit integrated into a road, rail, sea, or air transport unit. Mobile air conditioning or heat pump systems can be used in automobiles, trucks, railcars, or other transport systems. Mobile refrigeration can include transport refrigeration in trucks, aircraft, or railcars. Furthermore, devices designed to provide refrigeration for systems independent of any mobile transport vehicle (referred to as "intermodal" systems) are included in this invention. Such intermodal systems include "containers" (sea-land intermodal transport) and "interchangeable containers" (road-rail intermodal transport).

[0146] As used herein, a stationary air conditioning or heat pump system is a system that is located in a fixed position during operation. Stationary air conditioning or heat pump systems can be incorporated into or attached to a variety of buildings. These stationary applications can be stationary air conditioning and heat pumps, including but not limited to coolers (including centrifugal, screw, or scroll coolers), heat pumps (including residential heat pumps and high-temperature heat pumps), residential, commercial, or industrial air conditioning systems, and include window air conditioning systems, ductless air conditioning systems, ducted air conditioning systems, enclosed terminal air conditioning systems, and air conditioning systems located externally but connected to the building, such as rooftop systems.

[0147] Fixed heat transfer can refer to systems used to cool electronic equipment, such as immersion cooling systems, submerged cooling systems, phase change cooling systems, central data cooling systems, or simple liquid cooling systems.

[0148] In some embodiments, a method is provided for using the composition of the present invention as a heat transfer fluid. The method includes delivering the composition from a heat source to a radiator.

[0149] In some embodiments, a method for refrigeration is provided, comprising evaporating any of the compounds or compositions of the present invention near the subject to be cooled, and subsequently condensing the composition.

[0150] In some embodiments, a method for generating heat is provided, which includes condensing any of the compositions of the invention near the subject to be heated, and thereafter evaporating the composition.

[0151] In some embodiments, the composition is used for heat transfer, wherein the working fluid is the heat transfer component.

[0152] In some embodiments, the compositions of the present invention are used in the fields of refrigeration or air conditioning.

[0153] In some embodiments, the compositions of the present invention are used in coolers or heat pumps.

[0154] In some embodiments, the compositions of the present invention are used in methods that replace existing refrigerants.

[0155] In some embodiments, the compositions of the present invention can be used to reduce or eliminate the flammability of the flammable refrigerants provided herein. In some embodiments, the present application provided herein is a method for reducing the flammability of a flammable refrigerant, the method comprising adding a composition comprising the compositions disclosed herein to the flammable refrigerant.

[0156] The compositions provided herein can be used as alternatives to currently used (“existing”) refrigerants. As used herein, the term “existing refrigerant” should be understood to mean the refrigerant for which the heat transfer system was originally designed to operate, or the refrigerant currently present in the heat transfer system. In some embodiments, the existing refrigerant is selected from R-123 (2,2-dichloro-1,1,1-trifluoroethane), R-245fa (1,1,1,3,3-pentafluoropropane), R-514A (74.7... wt% HFO-1336mzzZ (Z-1,1,1,4,4,4-six) (a blend of fluoro-2-butene and 25.3 wt% trans-1,2-dichloroethylene) R-1233zdE (E-1-chloro-3,3,3-trifluoropropylene) and R-1224ydZ (Z-1-chloro-2,3,3,3-tetrafluoropropylene). In some embodiments, the existing refrigerant is R-123. In some embodiments, the existing refrigerant is R-245fa. In some embodiments, the existing refrigerant is R-514A. In some embodiments, the existing refrigerant is R-1233zdE. In some embodiments, the existing refrigerant is R-1224ydZ.

[0157] Typically, alternative refrigerants are most useful if they can be used in original refrigeration equipment designed for different refrigerants (e.g., with minimal or no system modifications). In many applications, some embodiments of the disclosed compositions can be used as refrigerants and provide cooling performance (i.e., cooling capacity) at least equivalent to that of the refrigerant to be replaced.

[0158] In some embodiments, a method for operating a heat transfer system or for transferring heat is provided, the heat transfer system being designed to operate with existing refrigerants, the method being achieved by charging an empty system with the composition of the present invention, or substantially replacing the existing refrigerant with the composition of the present invention. In some embodiments, the existing refrigerant is selected from R-123, R-245fa, R-514A, R-1233zdE, and R-1224ydZ. In some embodiments, the existing refrigerant is R-123. In some embodiments, the existing refrigerant is R-245fa. In some embodiments, the existing refrigerant is R-514A. In some embodiments, the existing refrigerant is R-1233zdE. In some embodiments, the existing refrigerant is R-1224ydZ.

[0159] As used herein, the term "substantially replace" should be understood to mean allowing existing refrigerant to be discharged from or pumped from the system before filling the system with the composition of the present invention. The system may be flushed with one or more amounts of the replacement refrigerant prior to filling. It should be understood that in some embodiments, a small amount of existing refrigerant may remain in the system after the composition of the present invention has been filled.

[0160] In another embodiment, a method is provided for refilling a heat transfer system containing an existing refrigerant and lubricant, the method comprising substantially removing the existing refrigerant from the heat transfer system while retaining a majority of the lubricant in the system, and introducing one of the compositions of the present invention into the heat transfer system. In some embodiments, the lubricant in the system is partially replaced. In some embodiments, the existing refrigerant is selected from R-123, R-245fa, R-514A, R-1233zdE, and R-1224ydZ. In some embodiments, the existing refrigerant is R-123. In some embodiments, the existing refrigerant is R-245fa. In some embodiments, the existing refrigerant is R-514A. In some embodiments, the existing refrigerant is R-1233zdE. In some embodiments, the existing refrigerant is R-1224ydZ.

[0161] In some embodiments, the compositions of the present invention can be used to replenish the refrigerant charge in a cooler. For example, if a cooler using one or more chlorofluoroethylenes provided herein experiences performance degradation due to the decomposition (e.g., oxidation) of the one or more chlorofluoroethylenes and refrigerant leakage, the compositions disclosed herein can be added to restore performance to specifications.

[0162] In some embodiments, a heat exchange system comprising any of the compositions disclosed herein is provided, wherein the system is selected from the group consisting of: air conditioners, refrigerators, freezers, heat pumps, water-cooled coolers, flooded evaporator coolers, direct expansion coolers, walk-in coolers, heat pumps, portable refrigerators, portable air conditioning units, and systems having combinations thereof. Furthermore, the compositions provided herein can be used in secondary loop systems, wherein these compositions act as the primary refrigerant and thus provide cooling to the secondary heat transfer fluid, thereby cooling a remote location.

[0163] Therefore, the system can operate more efficiently if the heat exchanger operates in counter-current mode or a cross-flow mode with counter-current tendency. Counter-current tendency means that the closer the heat exchanger is to counter-current mode, the more efficient the heat transfer. Therefore, air conditioning heat exchangers (especially evaporators) are designed to provide some aspects of counter-current tendency.

[0164] Therefore, this article provides an air conditioning or heat pump system, wherein the system includes one or more heat exchangers (evaporators, condensers or both) that operate in a counter-current mode or a cross-current mode with a counter-current tendency.

[0165] In some embodiments, this document provides a refrigeration system comprising one or more heat exchangers (evaporators, condensers, or both) that operate in a counter-current mode or a cross-flow mode with a counter-current tendency.

[0166] In some implementations, the refrigeration, air conditioning, or heat pump system is a stationary refrigeration, air conditioning, or heat pump system. In some implementations, the refrigeration, air conditioning, or heat pump system is a portable refrigeration, air conditioning, or heat pump system.

[0167] Furthermore, in some embodiments, the disclosed composition may act as a primary refrigerant in a secondary loop system that provides cooling to a remote location using a secondary heat transfer fluid, which may comprise water, an aqueous salt solution (e.g., calcium chloride), glycol, carbon dioxide, or a fluorinated hydrocarbon fluid (meaning HFC, HCFC, hydrofluoroolefin (“HFO”), hydrochlorofluoroolefin (“HCFO”), chlorofluoroolefin (“CFO”), or perfluorocarbon (“PFC”)). In this case, the secondary heat transfer fluid is the body to be cooled because it is adjacent to the evaporator and is cooled before moving to a second remote body to be cooled. In some embodiments, the disclosed composition may act as a secondary heat transfer fluid, thus transferring or providing cooling (or heating) to a remote location.

[0168] In some embodiments, the compositions provided herein also contain a lubricant.

[0169] In one embodiment, the lubricant is selected from the group consisting of: mineral oil, alkylbenzene, polyol ester, polyalkylene glycol, polyethylene ether, polycarbonate, perfluoropolyether, polysiloxane, silicate ester, phosphate ester, paraffin, cycloalkanes, polyalphaolefins, and combinations thereof.

[0170] The lubricant disclosed herein may be a commercially available lubricant. For example, the lubricant may be a paraffinic mineral oil (sold by BVA Oils under the trademark BVM 100 N); or by Crompton Co. under the trademark Suniso. ® 1GS, Suniso ® 3GS and Suniso ® 5GS sells cycloalkanes mineral oil; produced by Pennzoil under the trademark Sontex. ® 372LT is a naphthenic mineral oil sold under the trademark Calumet Lubricants. ®RO-30 is a cycloalkane mineral oil sold by Shrieve Chemicals under the trademark Zerol. ® 75. Zerol ® 150 and Zerol ® Straight-chain alkylbenzenes sold by 500; and branched-chain alkylbenzenes sold by Nippon Oil under the trademark HAB22; under the trademark Castrol ® 100 polyol esters (POEs) sold by Castrol, United Kingdom; polyalkylene glycols (PAGs) (such as RL-488A from Dow (Dow Chemical, Midland, Michigan)) and mixtures thereof, and such mixtures are meant to be any mixture of lubricants disclosed in this paragraph.

[0171] Although the weight proportions of the above compositions have been disclosed herein, it should be understood that in some heat transfer systems where the compositions are already used, one or more equipment components of such systems may still require additional lubricants. For example, in some refrigeration, air conditioning, and heat pump systems, lubricants may be filled into the compressor and / or compressor lubricant reservoir. Such lubricants are additional additions, independent of any lubricating additives already present in the refrigerant of such systems. During use, the refrigerant may carry a certain amount of equipment lubricant with it while in the compressor, altering the refrigerant-lubricant composition and causing it to deviate from the initial ratio.

[0172] In some embodiments, the compositions provided herein further comprise at least one dye. The dye may be at least one ultraviolet (UV) dye. As used herein, a “UV” dye is defined as a UV fluorescent or phosphorescent composition that absorbs light in the ultraviolet or “near” ultraviolet region of the electromagnetic spectrum. The fluorescence produced by a UV fluorescent dye under UV light irradiation can be detected, the UV light emitting at least some wavelengths ranging from 10 nanometers to about 775 nanometers.

[0173] UV dyes are useful for detecting leaks in compositions by making the fluorescence of the dye at or near a leak point in a device (such as a refrigeration unit, air conditioner, or heat pump) observable. This UV emission (e.g., fluorescence from the dye) can be observed under ultraviolet light. Therefore, if a composition containing such a UV dye leaks from a given point in the device, fluorescence can be detected at or near that leak point.

[0174] In some embodiments, the UV dye may be a fluorescent dye. In some embodiments, the fluorescent dye is selected from the group consisting of: naphthalenedicarboximide, perylene, coumarin, anthracene, phenanthrene, xanthannathoxane, naphthoxane, fluorescein, and derivatives of the dye and combinations thereof, whereby combinations refer to mixtures of any of the aforementioned dyes or derivatives thereof disclosed in this paragraph.

[0175] In some embodiments, the compositions provided herein further comprise at least one solubilizer selected to improve the solubility of one or more dyes in the disclosed compositions. In some embodiments, the weight ratio of dye to solubilizer is in the range of about 99:1 to about 1:1. The solubilizer comprises at least one compound selected from the group consisting of hydrocarbons, hydrocarbon ethers, polyoxyalkylene glycol ethers (such as dipropylene glycol dimethyl ether), amides, nitriles, ketones, chlorinated hydrocarbons (such as dichloromethane, trichloroethylene, chloroform, or mixtures thereof), esters, lactones, aromatic ethers, fluoroethers, and 1,1,1-trifluoroanes and mixtures thereof, where mixtures refer to mixtures of any of the solubilizers disclosed in this paragraph.

[0176] In some embodiments, the compositions provided herein further comprise at least one compatibilizer to improve the compatibility of one or more lubricants with the disclosed compositions. The compatibilizer may be selected from the group consisting of hydrocarbons, hydrocarbon ethers, polyoxyalkylene glycol ethers (such as dipropylene glycol dimethyl ether), amides, nitriles, ketones, chlorinated hydrocarbons (such as dichloromethane, trichloroethylene, chloroform, or mixtures thereof), esters, lactones, aromatic ethers, fluoroethers, 1,1,1-trifluoroanes, and mixtures thereof, where "mixtures" refers to a mixture of any of the compatibilizers disclosed in this paragraph.

[0177] The solubilizers and / or compatibilizers provided herein may be selected from the group consisting of hydrocarbon ethers (consisting of ethers containing only carbon, hydrogen and oxygen, such as dimethyl ether (DME)) and mixtures thereof, wherein such mixtures refer to any mixture of hydrocarbon ethers disclosed in this paragraph.

[0178] The compatibilizers provided herein may be straight-chain or cyclic aliphatic or aromatic hydrocarbon compatibilizers, and contain 3 to 15 carbon atoms. The compatibilizer may be at least one hydrocarbon, selected from the group consisting of at least the following: propane, including propylene and propane; butane, including n-butane and isobutene; pentane, including n-pentane, isopentane, neopentane, and cyclopentane; hexane; octane; nonane; and decane, etc. Commercially available hydrocarbon compatibilizers include, but are not limited to, those from Exxon Chemical (USA) and sold under the trademark Isopar. ® H (for undecane (C) 11 ) and dodecane (C 12 A mixture of (a high-purity C)11 To C 12 (Isoprosae), Aromatic 150 (C9 to C) 11 Aromatic 200 (C9 to C) 15 (Fang ethnic group) and Naptha 140 (C5 to C) 11 Mixtures of paraffins, cycloalkanes and aromatic hydrocarbons, and mixtures thereof, wherein such mixtures refer to any mixture of hydrocarbons disclosed in this paragraph.

[0179] The compatibilizers provided herein may alternatively be at least one polymeric compatibilizer. The polymeric compatibilizer may be a random copolymer of fluorinated and non-fluorinated acrylates, wherein the polymer comprises at least one compound of the formula CH2=C(R 1 CO2R 2 CH2=C(R) 3 C6H4R 4 and CH2=C(R 5 C6H4XR 6 The repeating unit of the monomer is represented, where X is oxygen or sulfur; R 1 R 3 and R 5 Independently selected from the group consisting of H and C1-C4 alkyl radicals; and R 2 R 4 and R 6 Independently selected from the group consisting of carbon-chain-based free radicals containing C and F, and may further contain H, Cl, ether oxygen, or sulfur in the form of sulfide, sulfoxide, or sulfone groups, and mixtures thereof. Examples of such polymerizable compatibilizers include those commercially available under the trademark Zonyl® PHS from El du Pont de Nemours and Company, (Wilmington, DE, 19898, USA). Zonyl ® PHS is a random copolymer, which is produced by polymerizing 40% by weight of CH2=C(CH3)CO2CH2CH2(CF2CF2). m F (also known as Zonyl) ® Methacrylate or ZFM, where m is 1 to 12, mainly 2 to 8) and 60% by weight lauryl methacrylate (CH2=C(CH3)CO2(CH2)). 11 It is made from CH3, also known as LMA.

[0180] In some embodiments, the compatibilizer components provided herein contain about 0.01 to 30 weight percent (based on the total amount of compatibilizer) of an additive that reduces the surface energy of metallic copper, aluminum, steel, or other metals and their alloys found in heat exchangers, thereby reducing the adhesion of the lubricant to the metal. Examples of additives that reduce metal surface energy include those marketed under the trademark Zonyl. ® FSA, Zonyl ® FSP and Zonyl ® The additives that FSJ purchases from DuPont.

[0181] In some embodiments, the compositions provided herein further comprise a metal surface deactivator. In some embodiments, the metal surface deactivator is selected from the group consisting of: oxalyl bis(benzylmethyl)hydrazide (CAS Registry No. 6629-10-3), N,N'-bis(3,5-di-tert-butyl-4-hydroxycinnamic acid)hydrazide (CAS Registry No. 32687-78-8), 2,2'-oxalamidobis-ethyl-(3,5-di-tert-butyl-4-hydroxycinnamate) (CAS Registry No. 70331-94-1), N,N'-(disaleneyl)-1,2-diaminopropane (CAS Registry No. 94-91-7), and ethylenediaminetetraacetic acid (CAS Registry No. 60-00-4), salts thereof, and mixtures thereof, wherein such mixtures refer to any mixture of metal surface deactivators disclosed in this paragraph.

[0182] In some embodiments, the compositions provided herein further comprise a tracer. The tracer may be two or more tracer compounds, derived from the same class of compounds or from different classes of compounds. In some embodiments, the tracer is present in the composition at a total concentration of about 50 parts per million (ppm) to about 1000 ppm based on the total weight of the composition. In some embodiments, the tracer is present at a total concentration of about 50 ppm to about 500 ppm. Alternatively, the tracer is present at a total concentration of about 100 ppm to about 300 ppm.

[0183] The tracer may be selected from the group consisting of: hydrofluorocarbons (HFCs), deuterated hydrofluorocarbons, perfluorocarbons, fluoroethers, brominated compounds, iodinated compounds, alcohols, aldehydes and ketones, nitrous oxide, and combinations thereof. Alternatively, the tracer may be selected from the group consisting of: trifluoromethane (HFC-23), fluoroethane (HFC-161), 1,1,1,2,2,3,3-heptafluoropropane (HFC-227ca), 1,1,1,2,2,3-hexafluoropropane (HFC-236cb), 1,1,1,2,3,3-hexafluoropropane (HFC-236ea), 1,1,1,2,2-pentafluoropropane (HFC-245cb), 1,1,2,2-tetrafluoropropane (HFC-254cb), 1,1,1,2- Tetrafluoropropane (HFC-254eb), 1,1,1-trifluoropropane (HFC-263fb), 2,2-difluoropropane (HFC-272ca), 2-fluoropropane (HFC-281ea), 1-fluoropropane (HFC-281fa), 1,1,1,2,2,3,3,4-nonafluorobutane (HFC-329p), 1,1,1-trifluoro-2-methylpropane (HFC-329mmz), 1,1,1,2,2,4,4,4-octafluorobutane (HFC-338mf), 1,1,2 2,3,3,4,4-Octafluoride (HFC-338pcc), 1,1,1,2,2,3,3-Hepenofluorobutane (HFC-347s), hexafluoroethane (perfluoroethane, PFC-116), perfluorocyclopropane (PFC-C216), perfluoropropane (PFC-218), perfluorocyclobutane (PFC-C318), perfluorobutane (PFC-31-10mc), perfluoro-2-methylpropane (CF3CF(CF3)2), perfluoro-1,3-dimethylcyclobutane (PFC-C51-12) Mycm), trans-perfluoro-2,3-dimethylcyclobutane (PFC-C51-12mym, trans), cis-perfluoro-2,3-dimethylcyclobutane (PFC-C51-12mym, cis), perfluoromethylcyclopentane, perfluoromethylcyclohexane, perfluorodimethylcyclohexane (ortho, meta, or para), perfluoroethylcyclohexane, perfluorodihydroindene, perfluorotrimethylcyclohexane and its isomers, perfluoroisopropylcyclohexane, cis-perfluorodecahydronaphthalene, trans-perfluorodecahydronaphthalene, cis- or trans-perfluoromethyldecahydronaphthalene, and mixtures thereof. In some embodiments, the tracer is a blend containing two or more hydrofluorocarbons, or a combination of one hydrofluorocarbon and one or more perfluorocarbons.

[0184] The tracer can be added to the composition of the present invention in a predetermined amount, so that any dilution, contamination or other changes to the composition can be detected.

[0185] It should be understood that some of the additives mentioned above that are suitable for use with non-refrigerant components have been identified as potential refrigerants. However, according to the present invention, when these additives are used, they are present in amounts that do not affect the novelty and essential properties of the refrigerant mixtures of the present invention.

[0186] In some embodiments, the refrigerant compositions disclosed herein can be prepared by any convenient method, thereby combining the components in desired amounts according to standards in the art. A preferred method is to weigh the required amounts of components and then combine them in a suitable container. Stirring may be used if necessary.

[0187] Example

[0188] This invention will be described in more detail by way of specific embodiments. The following embodiments are provided for illustrative purposes and are not intended to limit the invention in any way. Those skilled in the art will readily recognize that various non-critical parameters can be changed or modified to produce substantially the same results.

[0189] Example 1

[0190] A mixture of 1-chloro-2,2-difluoroethylene (HCFO-1122 (30 g)) with 1000 ppm air and 500 ppm water was heated to 50 °C in a 210 mL shaking tube for two weeks. The shaking tube was then cooled to room temperature (rt), and 30 mL of deionized water was added to the container. After phase separation, fluoride and chloride in the water were determined using ion chromatography, and pH was determined using a pH meter. Results for illustrative 1-chloro-2,2-difluoroethylene + stabilizer compositions are listed in Table 1. N / D = Not detected.

[0191] Table 1 .

[0192]

[0193] The following additional components were also identified in one or more compositions detected in Table 1: (E)-1-chloro-1,2-difluoroethylene (E-1122a); (Z)-1-chloro-1,2-difluoroethylene (Z-1122a); 1,2-dichloro-1,1-difluoroethane (R-132b); 2-chloro-1,1,1-trifluoroethane (R-133a); and 1-chloro-1,2,2,2-tetrafluoroethane (R-124).

[0194] Example 2 .

[0195] 30 g of 1-chloro-1,2-difluoroethylene (HCFO-1122a, 1:1 E / Z mixture) was heated to 50 °C in a 210 mL shaking tube with 1000 ppm air and 500 ppm water for two weeks. The shaking tube was then cooled to room temperature, and 30 mL of deionized water was added to the container. After phase separation, fluoride and chloride levels in the water were determined using ion chromatography, and the pH was measured using a pH meter. Results for illustrative 1-chloro-1,2-difluoroethylene + stabilizer compositions are listed in Table 2. N / D = Not detected.

[0196] Table 2 .

[0197]

[0198] The following additional components were also identified in one or more compositions detected in Table 2: 1-chloro-2,2-difluoroethylene (1122); (E)-1,2-dichloro-1,2-difluoroethylene (E-1112); (Z)-1,2-dichloro-1,2-difluoroethylene (Z-1112); 1-chloro-1,2,2-trifluoroethane (R-133); chlorotrifluoroethylene (R-1113); and 1-chloro-2,2,2-trifluoroethane (R-133a).

[0199] Other implementation plans

[0200] 1. In some embodiments, this application provides a composition comprising one or more vinyl chlorides and one or more stabilizer components, said stabilizer components being selected from antioxidants, acid scavengers, and metal stabilizers, or any combination thereof. Each of said one or more vinyl chlorides is independently selected from the group consisting of:

[0201] 1,1-Dichloro-2,2-difluoroethylene;

[0202] Chlorotrifluoroethylene;

[0203] 1-Chloro-2,2-Difluoroethylene;

[0204] E-1-Chloro-1,2-Difluoroethylene;

[0205] Z-1-Chloro-1,2-Difluoroethylene;

[0206] E-1-Chloro-2-fluoroethylene;

[0207] Z-1-Chloro-2-fluoroethylene;

[0208] 1-Chloro-1-fluoroethylene;

[0209] 1,2-Dichloro-1-fluoroethylene; and

[0210] 1,1-Dichloro-2-fluoroethylene.

[0211] 2. The composition according to embodiment 1, wherein the chlorofluoroethylene is selected from the group consisting of 1-chloro-2,2-difluoroethylene and 1-chloro-1,2-difluoroethylene.

[0212] 3. The composition according to embodiment 1, wherein the chlorofluoroethylene is 1-chloro-2,2-difluoroethylene.

[0213] 4. The composition according to embodiment 3, wherein the 1-chloro-1,2-difluoroethylene is (E)-1-chloro-1,2-difluoroethylene.

[0214] 5. The composition according to embodiment 3, wherein the 1-chloro-1,2-difluoroethylene is (Z)-1-chloro-1,2-difluoroethylene.

[0215] 6. The composition according to any one of embodiments 1 to 5, wherein the composition comprises one or more chlorofluoroethylenes and an antioxidant.

[0216] 7. The composition according to embodiment 6, wherein the antioxidant is selected from terpenes, butylated hydroxytoluene, butylated hydroxyanisole, tert-butylhydroquinone, propyl 3,4,5-trihydroxybenzoate, 2-phenyl-2-propanol, 1-(2,4,5-trihydroxyphenyl)-1-butanone, 4-methoxyphenol, bisphenol methane derivatives, 2,2'-methylenebis(4-methyl-6-tert-butylphenol), and 2-isopropyl-5-methylphenol.

[0217] 8. The composition according to any one of embodiments 1 to 5, wherein the composition comprises one or more chlorofluoroethylenes and an acid scavenger.

[0218] 9. The composition according to embodiment 8, wherein the acid scavenger is selected from epoxides and amines.

[0219] 10. The composition according to embodiment 8 or 9, wherein the acid scavenger is epoxide.

[0220] 11. The composition according to any one of embodiments 1 to 5, wherein the composition comprises one or more chlorofluoroethylenes and a metal stabilizer.

[0221] 12. The composition according to embodiment 11, wherein the metal stabilizer is selected from N,N'-bis(salicylyl)-1,2-propanediamine and benzotriazole.

[0222] 13. The composition according to any one of embodiments 1 to 5, wherein the composition comprises one or more of the chlorofluoroethylene, an antioxidant, and an acid scavenger.

[0223] 14. The composition according to any one of embodiments 1 to 5, wherein the composition comprises one or more chlorofluoroethylene, 1,2-epoxybutane and one or more antioxidants selected from m-xylene, o-xylene, p-xylene, thymol and pinene.

[0224] 15. The composition according to embodiment 1, wherein the composition comprises 1-chloro-2,2-difluoroethylene, 1,2-epoxybutane and one or more antioxidants selected from m-xylene, o-xylene, p-xylene, thymol and pinene.

[0225] 16. The composition according to embodiment 15, wherein the composition further comprises one or more additional compounds selected from:

[0226] (E)-1-chloro-1,2-difluoroethylene (E-1122a);

[0227] (Z)-1-chloro-1,2-difluoroethylene (Z-1122a);

[0228] 1,2-Dichloro-1,1-difluoroethane (R-132b);

[0229] 2-Chloro-1,1,1-trifluoroethane (R-133a); and

[0230] 1-Chloro-1,2,2,2-Tetrafluoroethane (R-124).

[0231] 17. The composition according to embodiment 1, wherein the composition comprises 1-chloro-1,2-difluoroethylene, 1,2-epoxybutane and one or more antioxidants selected from m-xylene, o-xylene, p-xylene, thymol and pinene.

[0232] 18. The composition according to embodiment 17, wherein the composition further comprises one or more additional compounds selected from:

[0233] 1-Chloro-2,2-difluoroethylene (1122);

[0234] (E)-1,2-dichloro-1,2-difluoroethylene (E-1112);

[0235] (Z)-1,2-Dichloro-1,2-difluoroethylene (Z-1112);

[0236] 1-Chloro-1,2,2-trifluoroethane (R-133);

[0237] Chlorotrifluoroethylene (R-1113); and

[0238] 1-Chloro-2,2,2-trifluoroethane (R-133a).

[0239] 19. The composition according to any one of embodiments 1 to 5, wherein the composition is substantially composed of: the one or more chlorofluoroethylenes and the one or more stabilizer components, wherein the one or more stabilizer components are selected from antioxidants, acid scavengers and metal stabilizers, or any combination thereof.

[0240] 20. The composition according to any one of embodiments 1 to 5, wherein the composition comprises: the one or more chlorofluoroethylenes and the one or more stabilizer components, wherein the one or more stabilizer components are selected from antioxidants, acid scavengers and metal stabilizers, or any combination thereof.

[0241] 21. The composition according to embodiment 16, wherein the composition comprises essentially the following: the 1-chloro-2,2-difluoroethylene, 1,2-epoxybutane, one or more antioxidants selected from the group consisting of m-xylene, o-xylene, p-xylene, thymol and pinene; and one or more additional compounds.

[0242] 22. The composition according to embodiment 16, wherein the composition comprises: the 1-chloro-2,2-difluoroethylene, 1,2-epoxybutane, one or more antioxidants selected from the group consisting of m-xylene, o-xylene, p-xylene, thymol, and pinene; and one or more additional compounds.

[0243] 23. The composition according to embodiment 18, wherein the composition comprises essentially the following: the 1-chloro-1,2-difluoroethylene, 1,2-epoxybutane, one or more antioxidants selected from the group consisting of m-xylene, o-xylene, p-xylene, thymol and pinene; and one or more additional compounds.

[0244] 24. The composition according to embodiment 18, wherein the composition comprises: the 1-chloro-1,2-difluoroethylene, 1,2-epoxybutane, one or more antioxidants selected from the group consisting of m-xylene, o-xylene, p-xylene, thymol and pinene; and one or more additional compounds.

[0245] 25. The composition according to any one of embodiments 1 to 24, wherein the one or more stabilizer components are present in the composition at the following concentrations: about 0.5 ppm, about 30 ppm, about 50 ppm, about 75 ppm, about 100 ppm, about 200 ppm, about 300 ppm, about 400 ppm, about 500 ppm, about 600 ppm, about 700 ppm, about 800 ppm, about 900 ppm, about 1000 ppm, about 1100 ppm, about 1200 ppm, about 1300 ppm, about 1400 ppm, or about 1500 ppm.

[0246] 26. The composition according to any one of embodiments 1 to 25, wherein the one or more stabilizer components are present in the composition at a concentration of X ppm to Y ppm, wherein:

[0247] aX is selected from the following groups: approximately 0.5 ppm, approximately 30 ppm, approximately 50 ppm, approximately 75 ppm, approximately 100 ppm, approximately 200 ppm, approximately 300 ppm, approximately 400 ppm, approximately 500 ppm, approximately 600 ppm, approximately 700 ppm, approximately 800 ppm, approximately 900 ppm, approximately 1000 ppm, approximately 1100 ppm, approximately 1200 ppm, approximately 1300 ppm, and approximately 1400 ppm; and

[0248] bY selects from the following groups: approximately 30 ppm, approximately 50 ppm, approximately 75 ppm, approximately 100 ppm, approximately 200 ppm, approximately 300 ppm, approximately 400 ppm, approximately 500 ppm, approximately 600 ppm, approximately 700 ppm, approximately 800 ppm, approximately 900 ppm, approximately 1000 ppm, approximately 1100 ppm, approximately 1200 ppm, approximately 1300 ppm, approximately 1400 ppm, and approximately 1500 ppm.

[0249] 27. In some embodiments, this application provides a method for refrigeration, the method comprising condensing a composition according to any one of embodiments 1 to 26, and subsequently evaporating the composition in the vicinity of the body to be cooled.

[0250] 28. In some embodiments, this application provides a method for heating, the method comprising evaporating a composition according to any one of embodiments 1 to 26, and subsequently condensing the composition in the vicinity of the body to be heated.

[0251] 29. In some embodiments, this application provides an air conditioning system, a heat pump system, a cooler system, or a refrigeration system, said system comprising a composition according to any one of embodiments 1 to 26.

[0252] 30. The air conditioning system, heat pump system, cooler system or refrigeration system according to embodiment 29, wherein the system includes an evaporator, a compressor, a condenser and an expansion device.

[0253] 31. In some embodiments, this application provides a method for replacing an existing refrigerant in an air conditioning system, heat pump system, cooler system, or refrigeration system, the method comprising providing a composition according to any one of embodiments 1 to 26.

[0254] 32. The method according to embodiment 31, wherein the existing refrigerant is selected from the group consisting of: R-123, R-245fa, R-514A, R-1233zdE and R-1224ydZ.

[0255] 33. The composition according to any one of embodiments 1 to 26, wherein the composition is free from or substantially free from Class A fluorinated substances, and wherein the degradation products of the composition are free from or substantially free from Class A fluorinated substances.

[0256] It should be understood that although the invention has been described in conjunction with its embodiments, the foregoing description is intended to be illustrative and not to limit the scope of the invention, which is defined by the scope of the appended claims. Other aspects, advantages, and modifications are within the scope of the following claims. Those skilled in the art will understand that any feature described herein with respect to any particular aspect and / or embodiment of the invention may be combined with one or more of any other feature of any other aspect and / or embodiment of the invention described herein, and appropriate modifications may be made to ensure compatibility of the combinations. Such combinations are considered part of the invention contemplated by this disclosure.

Claims

1. A composition comprising one or more vinyl chlorides and one or more stabilizer components, said one or more stabilizer components being selected from antioxidants, acid scavengers, and metal stabilizers, or any combination thereof; wherein each of said one or more vinyl chlorides is independently selected from the group consisting of: Trichlorofluoroethylene; 1,1-Dichloro-2,2-difluoroethylene; Chlorotrifluoroethylene; 1-Chloro-2,2-Difluoroethylene; E-1-Chloro-1,2-Difluoroethylene; Z-1-Chloro-1,2-Difluoroethylene; E-1-Chloro-2-fluoroethylene; Z-1-Chloro-2-fluoroethylene; 1-Chloro-1-fluoroethylene; 1,2-Dichloro-1-fluoroethylene; and 1,1-Dichloro-2-fluoroethylene.

2. The composition according to claim 1, wherein the chlorofluoroethylene is selected from the group consisting of 1-chloro-2,2-difluoroethylene and 1-chloro-1,2-difluoroethylene.

3. The composition according to claim 1, wherein the chlorofluoroethylene is 1-chloro-2,2-difluoroethylene.

4. The composition according to claim 1, wherein the chlorofluoroethylene is 1-chloro-1,2-difluoroethylene.

5. The composition according to claim 1, wherein the 1-chloro-1,2-difluoroethylene is (E)-1-chloro-1,2-difluoroethylene.

6. The composition according to claim 1, wherein the 1-chloro-1,2-difluoroethylene is (Z)-1-chloro-1,2-difluoroethylene.

7. The composition according to claim 1, wherein the composition comprises one or more chlorofluoroethylenes and an antioxidant.

8. The composition according to claim 1, wherein the antioxidant is selected from terpenes, butylated hydroxytoluene, butylated hydroxyanisole, tert-butylhydroquinone, propyl 3,4,5-trihydroxybenzoate, 2-phenyl-2-propanol, 1-(2,4,5-trihydroxyphenyl)-1-butanone, 4-methoxyphenol, bisphenol methane derivatives, 2,2'-methylenebis(4-methyl-6-tert-butylphenol), and 2-isopropyl-5-methylphenol.

9. The composition of claim 1, wherein the composition comprises one or more chlorofluoroethylenes and an acid scavenger.

10. The composition according to claim 1, wherein the acid scavenger is selected from epoxides and amines.

11. The composition according to claim 1, wherein the acid scavenger is epoxide.

12. The composition of claim 1, wherein the composition comprises one or more chlorofluoroethylenes and a metal stabilizer.

13. The composition according to claim 1, wherein the metal stabilizer is selected from N,N'-bis(salicylyl)-1,2-propanediamine and benzotriazole.

14. The composition of claim 1, wherein the composition comprises one or more of the chlorofluoroethylene, an antioxidant, and an acid scavenger.

15. The composition of claim 1, wherein the composition comprises one or more chlorofluoroethylenes, 1,2-epoxybutane, and one or more antioxidants selected from m-xylene, o-xylene, p-xylene, thymol, and pinene.

16. The composition of claim 1, wherein the composition comprises 1-chloro-2,2-difluoroethylene, 1,2-epoxybutane and one or more antioxidants selected from the group consisting of m-xylene, o-xylene, p-xylene, thymol, and pinene.

17. The composition of claim 16, further comprising one or more additional compounds selected from: (E)-1-chloro-1,2-difluoroethylene (E-1122a); (Z)-1-chloro-1,2-difluoroethylene (Z-1122a); 1,2-Dichloro-1,1-difluoroethane (R-132b); 2-Chloro-1,1,1-trifluoroethane (R-133a); and 1-Chloro-1,2,2,2-Tetrafluoroethane (R-124).

18. The composition of claim 1, wherein the composition comprises 1-chloro-1,2-difluoroethylene, 1,2-epoxybutane and one or more antioxidants selected from m-xylene, o-xylene, p-xylene, thymol and pinene.

19. The composition of claim 18, further comprising one or more additional compounds selected from: 1-Chloro-2,2-difluoroethylene (1122); (E)-1,2-dichloro-1,2-difluoroethylene (E-1112); (Z)-1,2-Dichloro-1,2-difluoroethylene (Z-1112); 1-Chloro-1,2,2-trifluoroethane (R-133); Chlorotrifluoroethylene (R-1113); and 1-Chloro-2,2,2-trifluoroethane (R-133a).

20. The composition according to claim 1, wherein the composition comprises substantially the following: The one or more chlorofluoroethylenes and the one or more stabilizer components, wherein the one or more stabilizer components are selected from antioxidants, acid scavengers and metal stabilizers, or any combination thereof.

21. The composition according to claim 1, wherein the composition comprises: The one or more chlorofluoroethylenes and the one or more stabilizer components, wherein the one or more stabilizer components are selected from antioxidants, acid scavengers and metal stabilizers, or any combination thereof.

22. The composition according to claim 17, wherein the composition comprises substantially the following: The 1-chloro-2,2-difluoroethylene, 1,2-epoxybutane, one or more antioxidants selected from the following: m-xylene, o-xylene, p-xylene, thymol, d-limonene, and pinene; and one or more additional compounds.

23. The composition according to claim 17, wherein the composition comprises: The 1-chloro-2,2-difluoroethylene, 1,2-epoxybutane, one or more antioxidants selected from the following: m-xylene, o-xylene, p-xylene, thymol, d-limonene, and pinene; and one or more additional compounds.

24. The composition according to claim 19, wherein the composition comprises substantially the following: The 1-chloro-1,2-difluoroethylene, 1,2-epoxybutane, one or more antioxidants selected from the group consisting of m-xylene, o-xylene, p-xylene, thymol, d-limonene, and pinene; and one or more additional compounds.

25. The composition according to claim 19, wherein the composition comprises: The 1-chloro-1,2-difluoroethylene, 1,2-epoxybutane, one or more antioxidants selected from the group consisting of m-xylene, o-xylene, p-xylene, thymol, d-limonene, and pinene; and one or more additional compounds.

26. A method for refrigeration, the method comprising condensing the composition according to claim 1, and subsequently evaporating the composition in the vicinity of the body to be cooled.

27. A method for generating heat, the method comprising evaporating the composition according to claim 1, and subsequently condensing the composition in the vicinity of the body to be heated.

28. An air conditioning system, heat pump system, cooler system, or refrigeration system, said system comprising the composition according to claim 1.

29. The air conditioning system, heat pump system, cooler system or refrigeration system according to claim 28, wherein the system includes an evaporator, a compressor, a condenser and an expansion device.

30. A method for replacing an existing refrigerant in an air conditioning system, heat pump system, cooler system, or refrigeration system, the method comprising providing a composition according to claim 1 in place of the existing refrigerant.

31. The method of claim 30, wherein the conventional refrigerant is selected from the group consisting of: R-123, R-245fa, R-514A, R-1233zdE and R-1224ydZ.

32. The composition of claim 1, wherein the composition is free from or substantially free from Class A fluorinated substances, and wherein the degradation products of the composition are free from or substantially free from Class A fluorinated substances.

Images