Azeotropic compositions comprising bis (perfluoroalkyl) ethylene and uses thereof

Abstract

A composition includes bis (perfluoroalkyl) ethylene and at least one additional compound. Bis (perfluoroalkyl) ethylene and at least one additional compound are present in the composition in an amount effective to form an azeotropic or azeotrope-like composition. A method of coating a surface includes dissolving a coating composition in a carrier liquid to form a solution. The carrier liquid comprises an azeotropic or azeotrope-like composition. The method further includes applying the solution to the surface and removing the carrier liquid from the coating composition to coat the surface with the coating composition. A method of cooling a system includes two-phase immersion cooling of the system with a coolant comprising an azeotropic or azeotrope-like composition. A method of cleaning a surface includes contacting a composition comprising an azeotropic or azeotrope-like composition with a surface.

Description

Technical Field

[0001] This disclosure relates to azeotropic or azeotropic compositions comprising bis(perfluoroalkyl)ethylene and at least one additional compound. The compositions described herein can be used, for example, in precision cleaning and heat transfer applications, as well as as carrier fluids. Background Technology

[0002] Fluorinated compounds, such as perfluorocarbons (PFCs), hydrofluorocarbons (HFCs), and hydrofluoroethers (HFEs), are widely used in demanding applications, such as precision cleaning, heat transfer, and liquid-carrying applications, due to their high thermal stability, relatively low toxicity, and non-flammability. These fluorinated compounds offer unique properties such as high density and low surface tension.

[0003] These substances are often blended with other components to enhance solubility or improve heat transfer properties, such as specific heat capacity, boiling point, or heat of vaporization, for cleaning and fluid-carrying applications. Many of these applications, including vapor degreasing for cleaning and two-phase evaporative cooling for heat transfer, require formulations with azeotropic properties to ensure consistent composition. Non-flammable HFC compounds and blends have been widely used in fluid-carrying, precision cleaning, and heat transfer operations, providing non-flammability and improved worker safety for critical applications in the electronics, aerospace, and defense industries.

[0004] However, these highly stable PFC, HFC, and HFE compounds all have long atmospheric lifetimes when released into the atmosphere and are subject to increasing scrutiny due to their high global warming potential (GWP) and therefore their contribution to global warming. Hydrofluoroolefin (HFO) compounds have recently been commercially introduced as low-GWP alternatives to these high-GWP substances. However, currently available HFO compounds have boiling points significantly lower or higher than existing PFC, HFC, and HFE compounds, which may hinder the transition to these sustainable alternatives.

[0005] Therefore, there is a need for new low-GWP formulations with boiling points in the range of 40°C to 60°C, which can serve as more direct alternatives to existing fluorinated compounds. Summary of the Invention

[0006] This disclosure particularly provides a composition comprising:

[0007] i) bis(perfluoroalkyl)ethylene; and

[0008] ii) at least one additional compound;

[0009] The bis(perfluoroalkyl)ethylene and at least one additional compound are present in the composition in an amount that effectively forms an azeotropic composition or an azeotropic-like composition.

[0010] This disclosure also provides a method for coating a surface, the method comprising:

[0011] The coating composition is dissolved in a carrier liquid to form a solution, the carrier liquid containing bis(perfluoroalkyl)ethylene and at least one additional compound in an amount of an azeotropic composition or azeotropic-like composition that effectively forms the carrier liquid.

[0012] Apply the solution to the surface; and

[0013] Remove the carrier liquid from the coating composition to coat the surface with the coating composition.

[0014] This disclosure further provides a method for cooling a system, the method comprising two-phase immersion cooling of the system with a coolant comprising bis(perfluoroalkyl)ethylene and at least one additional compound present in an amount that effectively forms an azeotropic composition or azeotropic-like composition of the coolant.

[0015] This disclosure further provides a method for cleaning a surface, the method comprising contacting a composition with the surface, the composition comprising bis(perfluoroalkyl)ethylene and at least one additional compound present in an amount that effectively forms an azeotropic or azeotropic composition.

[0016] 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; alternatively, suitable methods and materials known in the art may also be used. The materials, methods, and examples described are exemplary 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 case of any conflict, this specification and its included definitions shall prevail.

[0017] Various aspects and embodiments of the present invention can be used alone or in combination with each other. Other features and advantages of the invention will become apparent from the following more detailed description of preferred embodiments of the principles of the invention, illustrated by way of example. Attached Figure Description

[0018] Figure 1 The boiling points of a binary mixture of E-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (E-HFO-153-10mczz) and perfluoroethyl isopropyl ketone (PEIK) at atmospheric pressure are shown.

[0019] Figure 2 The boiling points of a binary mixture of E-HFO-153-10mczz and cis-1-chloro-2,3,3-trifluoropropene (HCFO-1233ydZ) at atmospheric pressure are shown.

[0020] Figure 3 The boiling points of a binary mixture of E-HFO-153-10mczz and 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether (HFE-347pc-f) at atmospheric pressure are shown.

[0021] Figure 4 The boiling point of a binary mixture of E-HFO-153-10mczz and cyclohexane at atmospheric pressure is shown.

[0022] Figure 5 The boiling points of a binary mixture of E-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)-2-pentene (E-HFO-153-10mzzy) and PEIK at atmospheric pressure are shown.

[0023] Figure 6 The boiling points of a binary mixture of E-HFO-153-10mzzy and HCFO-1233ydZ at atmospheric pressure are shown.

[0024] Figure 7 The boiling point of a binary mixture of E-HFO-153-10mzzy and HFE-347pc-f at atmospheric pressure is shown.

[0025] Figure 8 The boiling point of a binary mixture of E-HFO-153-10mzzy and cyclohexane at atmospheric pressure is shown.

[0026] Figure 9 The boiling point of a binary mixture of E-HFO-153-10mzzy and n-heptane at atmospheric pressure is shown.

[0027] Figure 10 The boiling point of a binary mixture of E-HFO-153-10mzzy and n-hexane at atmospheric pressure is shown.

[0028] Figure 11 The boiling point of a binary mixture of E-HFO-153-10mzzy and acetone at atmospheric pressure is shown.

[0029] Figure 12 The boiling point of the binary mixture of E-HFO-153-10mzzy and methyl acetate at atmospheric pressure is shown.

[0030] Figure 13 The boiling point of a binary mixture of E-HFO-153-10mzzy and methylcyclohexane at atmospheric pressure is shown.

[0031] Figure 14The boiling point of a binary mixture of E-HFO-153-10mzzy and hexafluoropropyl methyl ether (HFPME) at atmospheric pressure is shown. Detailed Implementation

[0032] An azeotropic or azeotropic composition comprising bis(perfluoroalkyl)ethylene and at least one additional compound is disclosed. Also disclosed are azeotropic or azeotropic compositions comprising bis(perfluoroalkyl)ethylene and at least one additional compound, and related methods, for cleaning, liquid-carrying, and heat transfer applications.

[0033] This disclosure provides novel binary and ternary azeotropic and azeotropic-like compositions comprising mixtures of hydrofluorocarbons. These compositions are practical in many applications previously provided by chlorofluorocarbon (CFC) compounds. The compositions of this disclosure have some or all of the following desirable properties: minimal or no environmental impact, and the ability to dissolve oils, greases, and / or fluxes.

[0034] In an exemplary embodiment, bis(perfluoroalkyl)ethylene has the chemical structure shown in formula (1):

[0035] R1CH=CHR2(1)

[0036] Where R1 and R2 are independently of equation C n F 2n+1 Straight-chain or branched perfluorinated carbon, where n is an integer in the range of 1 to 5.

[0037] The stereoisomer composition of bis(perfluoroalkyl)ethylene can be a pure Z (cis) isomer, a pure E (trans) isomer, or any mixture of Z and E isomers. Definitions and abbreviations

[0038] 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 elements, but may include other elements not expressly listed or inherent to such process, method, article of manufacture, or apparatus. Furthermore, unless expressly stated otherwise, “or” refers to an inclusive or non-exclusive or. For example, conditions A or B satisfy one of the following: A is true (or exists) and B is false (or does not exist); A is false (or does not exist) and B is true (or exists); and both A and B are true (or exist).

[0039] As used herein, the term "substantially composed of" is used to define a composition or method that includes, in addition to those disclosed in the literature, materials, steps, features, components, or elements, provided that such additionally included materials, steps, features, components, or elements do not significantly affect one or more essential and novel features of the invention protected by the claims, particularly the mode of action for achieving the desired results of any of the methods of the invention. The term "substantially composed of" occupies an intermediate position between "comprising" and "composed of".

[0040] Furthermore, the terms "an" or "a" are used to describe the elements and components described herein. This is for convenience only and to give a general meaning to the scope of the invention. The description should be understood to include one or at least one, and the singular includes the plural, unless it is obvious that it means otherwise.

[0041] As used herein, the term “about” is intended to account for variations due to experimental error (e.g., adding or subtracting approximately 10% of the indicated value). Unless otherwise expressly stated, all measurements reported herein should be understood to be modified by the term “about,” whether or not the term is explicitly used.

[0042] As used in this article, the term "atmospheric pressure" refers to a pressure of approximately 101 MPa.

[0043] As used herein, the term "%isomeric pure body" refers to the weight of the isomeric compound relative to the total weight of the isomeric compound and its stereoisomers.

[0044] When quantities, concentrations, or other values ​​or parameters are given as a list of ranges, preferred ranges, or preferred upper and / or preferred lower limits, it should be understood as specifically disclosing all ranges formed by any pair of any upper or preferred range value and any lower or preferred range value, regardless of whether the range is disclosed individually. Wherever a numerical range is given herein, the range is intended to include its endpoints, as well as all integers and fractions within that range, unless otherwise indicated.

[0045] As is known in the art, an azeotropic composition is a mixture of two or more different components that, when in liquid form and (1a) at a given constant pressure, will boil at a substantially constant temperature, which may be higher or lower than the boiling temperature of a single component, or (1b) at a given constant temperature, will boil at a substantially constant pressure, which may be higher or lower than the boiling pressure of a single component, and (2) will boil at a substantially constant composition, although the phase composition is constant, it is not necessarily equal (see, for example, MF Doherty and MFMalone, Conceptual Design of Distillation Systems, McGraw-Hill (New York), 2001, 185).

[0046] In addition to the characteristics (1a), (1b) and (2) mentioned above, homogeneous azeotropes are substances in which a single gas phase and a single liquid phase are in equilibrium, and the composition of each component is identical in each coexisting equilibrium phase. The general term "azeotrope" is a commonly used alternative name for homogeneous azeotropes.

[0047] As used herein, an "azeotropic-like" composition is one that behaves similarly to an azeotropic composition (i.e., exhibiting constant boiling characteristics or a tendency not to fractionate upon boiling or evaporation). Therefore, during boiling or evaporation, the vapor and liquid compositions, if fundamentally altered, change only to a minimal or negligible degree. Conversely, the vapor and liquid compositions of non-azeotropic compositions undergo substantial changes during boiling or evaporation.

[0048] As used herein, the term "azeotropic-like" or "azeotropic-like behavior" refers to a composition that exhibits a dew point pressure and a bubble point pressure with almost no pressure difference. In some embodiments, the difference between the dew point pressure and the bubble point pressure at a given temperature is 3% or less. In some embodiments, the difference between the bubble point pressure and the dew point pressure is 5% or less. Azeotropic and azeotropic compositions

[0049] This disclosure provides a composition comprising:

[0050] i) bis(perfluoroalkyl)ethylene; and

[0051] ii) at least one additional compound;

[0052] The bis(perfluoroalkyl)ethylene and at least one additional compound are present in the composition in an amount that effectively forms an azeotropic composition or an azeotropic-like composition.

[0053] In some embodiments, bis(perfluoroalkyl)ethylene and at least one additional compound constitute at least 98% by weight of the composition. In some embodiments, bis(perfluoroalkyl)ethylene and at least one additional compound constitute at least 99% by weight of the composition. In some embodiments, bis(perfluoroalkyl)ethylene and at least one additional compound constitute at least 99.5% by weight of the composition. In some embodiments, the composition consists essentially of bis(perfluoroalkyl)ethylene and at least one additional compound. In some embodiments, the composition consists of bis(perfluoroalkyl)ethylene and at least one additional compound.

[0054] In some embodiments, bis(perfluoroalkyl)ethylene is at least 99 wt% isomer purity, such as, for example, at least 99.5 wt%, at least 99.8 wt%, or at least 99.9 wt%, in Z or E form. In other embodiments, bis(perfluoroalkyl)ethylene is a mixture of Z and E isomers, such as, for example, 40 wt% to 60 wt% Z form and 40 wt% to 60 wt% E form. In some embodiments, bis(perfluoroalkyl)ethylene is a synthetic isomer mixture, rather than a Z-rich or E-rich fraction.

[0055] In some embodiments, bis(perfluoroalkyl)ethylene is E-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (E-HFO-153-10mczz) and / or E-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)-2-pentene (E-HFO-153-10mzzy).

[0056] In some embodiments, the composition is a binary azeotrope.

[0057] In some embodiments, the additional compounds include perfluoroethyl isopropyl ketone, cis-1-chloro-2,3,3-trifluoropropene, 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether, cyclohexane, cyclopentane, n-heptane, n-hexane, acetone, methyl acetate, methylcyclohexane, hexafluoropropyl methyl ether (HFPME), or combinations thereof.

[0058] In some embodiments, the composition comprises, by weight, about 37% to about 76% E-HFO-153-10mczz and about 24% to about 63% perfluoroethyl isopropyl ketone, or any value, range, or subrange thereof. In some embodiments, the composition has a boiling point in the range of about 48.5°C to about 48.8°C at a pressure of about 101 kPa.

[0059] In some embodiments, the composition comprises about 43% to about 66% E-HFO-153-10mczz and about 34% to about 57% perfluoroethyl isopropyl ketone by weight. In some embodiments, the composition has a boiling point in the range of about 48.5°C to about 48.7°C at a pressure of about 101 kPa.

[0060] In some embodiments, the composition comprises, by weight, about 54% to about 83% E-HFO-153-10mczz and about 17% to about 46% cis-1-chloro-2,3,3-trifluoropropene, or any value, range, or subrange thereof. In some embodiments, the composition has a boiling point in the range of about 44.4°C to about 45.1°C at a pressure of about 101 kPa.

[0061] In some embodiments, the composition comprises about 60% to about 78% E-HFO-153-10mczz and about 22% to about 40% cis-1-chloro-2,3,3-trifluoropropene by weight. In some embodiments, the composition has a boiling point in the range of about 44.4°C to about 44.8°C at a pressure of about 101 kPa.

[0062] In some embodiments, the composition comprises, by weight, about 54% to about 91% E-HFO-153-10mczz and about 9% to about 46% 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether, or any value, range, or subrange thereof. In some embodiments, the composition has a boiling point in the range of about 50.5°C to about 51.5°C at a pressure of about 101 kPa.

[0063] In some embodiments, the composition comprises, by weight, about 60% to about 84% E-HFO-153-10mczz and about 16% to about 40% 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether. In some embodiments, the composition has a boiling point in the range of about 50.5°C to about 51.0°C at a pressure of about 101 kPa.

[0064] In some embodiments, the composition comprises, by weight, about 84% to about 95% E-HFO-153-10mczz and about 5% to about 16% cyclohexane, or any value, range, or subrange thereof. In some embodiments, the composition has a boiling point in the range of about 46.4°C to about 46.9°C at a pressure of about 101 kPa.

[0065] In some embodiments, the composition comprises about 86% to about 94% E-HFO-153-10mczz and about 6% to about 14% cyclohexane by weight. In some embodiments, the composition has a boiling point in the range of about 46.4°C to about 46.7°C at a pressure of about 101 kPa.

[0066] In some embodiments, the composition comprises, by weight, about 53% to about 79% E-HFO-153-10mczz and about 21% to about 47% cyclopentane, or any value, range, or subrange thereof. In some embodiments, the composition has a boiling point in the range of about 35°C to about 36°C at a pressure of about 101 kPa.

[0067] In some embodiments, the composition comprises E-HFO-153-10mczz and has a boiling point of about 35°C to about 49°C at a pressure of about 101 kPa, or any value, range, or subrange thereof.

[0068] In some embodiments, the composition comprises, by weight, about 10% to about 60% E-HFO-153-10mzzy and about 40% to about 90% perfluoroethyl isopropyl ketone, or any value, range, or subrange thereof. In some embodiments, the composition has a boiling point in the range of about 48.0°C to about 48.4°C at a pressure of about 101 kPa.

[0069] In some embodiments, the composition comprises about 18% to about 45% E-HFO-153-10mzzy and about 55% to about 82% perfluoroethyl isopropyl ketone by weight. In some embodiments, the composition has a boiling point in the range of about 48.0°C to about 48.2°C at a pressure of about 101 kPa.

[0070] In some embodiments, the composition comprises, by weight, about 55% to about 83% E-HFO-153-10mzzy and about 17% to about 45% cis-1-chloro-2,3,3-trifluoropropene, or any value, range, or subrange thereof. In some embodiments, the composition has a boiling point in the range of about 43.7°C to about 44.5°C at a pressure of about 101 kPa.

[0071] In some embodiments, the composition comprises about 60% to about 78% E-HFO-153-10mzzy and about 22% to about 40% cis-1-chloro-2,3,3-trifluoropropene by weight. In some embodiments, the composition has a boiling point in the range of about 43.7°C to about 44.2°C at a pressure of about 101 kPa.

[0072] In some embodiments, the composition comprises, by weight, about 65% to about 92% E-HFO-153-10mzzy and about 8% to about 35% 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether, or any value, range, or subrange thereof. In some embodiments, the composition has a boiling point in the range of about 47.9°C to about 48.2°C at a pressure of about 101 kPa.

[0073] In some embodiments, the composition comprises, by weight, about 68% to about 91% E-HFO-153-10mzzy and about 9% to about 32% 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether. In some embodiments, the composition has a boiling point in the range of about 47.9°C to about 48.1°C at a pressure of about 101 kPa.

[0074] In some embodiments, the composition comprises, by weight, about 81.2% to about 94.5% E-HFO-153-10mzzy and about 5.5% to about 18.8% cyclohexane, or any value, range, or subrange thereof. In some embodiments, the composition has a boiling point in the range of about 46.6°C to about 47.0°C at a pressure of about 101 kPa.

[0075] In some embodiments, the composition comprises about 83.8% to about 93.5% E-HFO-153-10mzzy and about 6.5% to about 16.2% cyclohexane by weight. In some embodiments, the composition has a boiling point in the range of about 46.6°C to about 47.0°C at a pressure of about 101 kPa.

[0076] In some embodiments, the composition comprises, by weight, about 52% to about 84% E-HFO-153-10mzzy and about 16% to about 48% cyclopentane, or any value, range, or subrange thereof. In some embodiments, the composition has a boiling point in the range of about 35.5°C to about 36.5°C at a pressure of about 101 kPa.

[0077] In some embodiments, the composition comprises, by weight, about 96.6% to about 98.6% E-HFO-153-10mzzy and about 1.4% to about 3.4% n-heptane, or any value, range, or subrange thereof. In some embodiments, the composition has a boiling point in the range of about 48.5°C to about 48.7°C at a pressure of about 101 kPa.

[0078] In some embodiments, the composition comprises, by weight, about 71% to about 93% E-HFO-153-10mzzy and about 7% to about 29% n-hexane, or any value, range, or subrange thereof. In some embodiments, the composition has a boiling point in the range of about 44.3°C to about 44.9°C at a pressure of about 101 kPa.

[0079] In some embodiments, the composition comprises about 77% to about 92% E-HFO-153-10mzzy and about 8% to about 23% n-hexane by weight. In some embodiments, the composition has a boiling point in the range of about 44.3°C to about 44.6°C at a pressure of about 101 kPa.

[0080] In some embodiments, the composition comprises, by weight, about 75% to about 91% E-HFO-153-10mzzy and about 9% to about 25% acetone, or any value, range, or subrange thereof. In some embodiments, the composition has a boiling point in the range of about 46.4°C to about 46.9°C at a pressure of about 101 kPa.

[0081] In some embodiments, the composition comprises about 79% to about 89.5% E-HFO-153-10mzzy and about 10.5% to about 21% acetone by weight. In some embodiments, the composition has a boiling point in the range of about 46.4°C to about 46.7°C at a pressure of about 101 kPa.

[0082] In some embodiments, the composition comprises, by weight, about 66% to about 88.7% E-HFO-153-10mzzy and about 11.3% to about 34% methyl acetate, or any value, range, or subrange thereof. In some embodiments, the composition has a boiling point in the range of about 47.3°C to about 47.8°C at a pressure of about 101 kPa.

[0083] In some embodiments, the composition comprises about 69% to about 84.4% E-HFO-153-10mzzy and about 15.6% to about 31% methyl acetate by weight. In some embodiments, the composition has a boiling point in the range of about 47.3°C to about 47.8°C at a pressure of about 101 kPa.

[0084] In some embodiments, the composition comprises, by weight, about 97.2% to about 98.5% E-HFO-153-10mzzy and about 1.5% to about 2.8% methylcyclohexane, or any value, range, or subrange thereof. In some embodiments, the composition has a boiling point in the range of about 49.3°C to about 49.5°C at a pressure of about 101 kPa.

[0085] In some embodiments, the composition comprises, by weight, about 70% to about 91% E-HFO-153-10mzzy and about 9% to about 30% HFPME, or any value, range, or subrange thereof. In some embodiments, the composition has a boiling point in the range of about 48.3°C to about 48.7°C at a pressure of about 101 kPa.

[0086] In some embodiments, the composition is a ternary azeotrope.

[0087] In some embodiments, the composition comprises, by weight, about 70% to about 74% E-HFO-153-10mzzy, about 18% to about 19% 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether, and about 8% to about 11% cyclohexane, or any values, ranges, or subranges thereof. In some embodiments, the composition has a boiling point in the range of about 46.0°C to about 46.6°C at a pressure of about 101 kPa.

[0088] In some embodiments, the composition comprises, by weight, about 68% to about 72% E-HFO-153-10mzzy, about 20% to about 21.5% cis-1-chloro-2,3,3-trifluoropropene, and about 9% to about 10% n-hexane, or any value, range, or subrange thereof. In some embodiments, the composition has a boiling point in the range of about 43.0°C to about 43.8°C at a pressure of about 101 kPa.

[0089] In some embodiments, the composition comprises, by weight, about 69% to about 73% E-HFO-153-10mzzy, about 23% to about 26% cis-1-chloro-2,3,3-trifluoropropene, and about 4% to about 5% cyclohexane, or any value, range, or subrange thereof. In some embodiments, the composition has a boiling point in the range of about 44.8°C to about 45.4°C at a pressure of about 101 kPa. How to use

[0090] In some embodiments, the compositions described herein can be used as a carrier fluid. In some embodiments, the carrier fluid facilitates the deposition of fluorinated lubricants, such as fluorinated lubricants for hard disk drives, for example. Therefore, this disclosure also provides a method for depositing a fluorinated lubricant, the method comprising contacting the compositions described herein with the fluorinated lubricant and transporting the fluorinated lubricant together with the compositions to a target location.

[0091] In some embodiments, the method of coating a surface includes dissolving a coating composition in a carrier liquid of the composition described herein to form a solution. The method further includes applying the solution to the surface and removing the carrier liquid from the coating composition to coat the surface with the coating composition. In some embodiments, the coating composition comprises a perfluoropolyether. In some embodiments, the surface is the surface of a hard disk drive.

[0092] In some embodiments, the compositions described herein can be used as a coolant. In some embodiments, the compositions described herein are coolants in two-phase immersion cooling systems. In some embodiments, two-phase immersion cooling systems are used in data centers or electric vehicle battery packs. Therefore, this disclosure also provides a method for cooling a system, the method comprising performing two-phase immersion cooling on the system using the compositions described herein.

[0093] In some embodiments, the compositions described herein can be used as degreasing agents and / or cleaning agents for precision cleaning and / or industrial cleaning. In some embodiments, the compositions described herein can be used for vapor degreasing, aerosol cleaning, and / or cold cleaning. Therefore, this disclosure also provides methods for cleaning surfaces, the methods comprising contacting the surfaces with the compositions described herein.

[0094] The method of contacting the device, surface, or substrate is not critical and can be achieved, for example, by immersing the device, surface, or substrate in a bath containing the composition provided herein, spraying the device, surface, or substrate with the composition provided herein, or wiping the device, surface, or substrate with a material (e.g., a cloth) moistened with the composition. Alternatively, the compositions provided herein can also be used in vapor degreasing or solder stripping equipment designed for the removal of such residues. Such vapor degreasing or solder stripping equipment is available from various suppliers, such as Forward Technology (a subsidiary of Crest Group, Trenton, NJ), Trek Industries (Azusa, CA), and Ultronix, Inc. (Hatfield, PA), among others.

[0095] In some embodiments, the surface or substrate may be an integrated circuit device, in which case the residue includes rosin flux or oil. The integrated circuit device may be a circuit board with various types of components, such as flip chips, micro-ball grid arrays (µBGAs), or chip-scale packaged components. The surface or substrate may additionally be a metallic surface, such as stainless steel. The rosin flux may be any type commonly used for soldering integrated circuit devices, including but not limited to RMA (medium-active rosin), RA (active rosin), WS (water-soluble), and OA (organic acid). Oil residues include, but are not limited to, mineral oil, machine oil, and silicone oil.

[0096] In some implementations, the compositions described herein can be used in the electronics, aerospace, and / or defense industries.

[0097] In some embodiments, an azeotropic or azeotropic composition comprising bis(perfluoroalkyl)ethylene and at least one additional compound can be used in any or all of the above-described methods of use. In some embodiments, the bis(perfluoroalkyl)ethylene and at least one additional compound constitute at least 98% by weight of such a composition. In some embodiments, the bis(perfluoroalkyl)ethylene and at least one additional compound constitute at least 99% by weight of such a composition. In some embodiments, such a composition consists essentially of bis(perfluoroalkyl)ethylene and at least one additional compound. In some embodiments, such a composition consists of bis(perfluoroalkyl)ethylene and at least one additional compound. Example

[0098] The invention will be described in more detail through 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.

[0099] In the following embodiments, E-HFO-153-10mczz is trans-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (HFO-153-10mczz(E)) having less than 0.1 mol% cis-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (HFO-153-10mczz(Z)), and E-HFO-153-10mzzy is trans-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)-2-pentene (HFO-153-10mzzy(E)) having less than 0.1 mol% cis-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)-2-pentene (HFO-153-10mzzy(Z)). Example 1

[0100] Solvents were screened based on their azeotropic behavior with E-HFO-153-10mczz or E-HFO-153-10mzzy using an atmospheric boiling point meter. The screened solvents included perfluoroethyl isopropyl ketone (PEIK; Novec). ™ 649; 3M, St. Paul, MN), cis-1-chloro-2,3,3-trifluoropropene (HCFO-1233ydZ; AsahiKlin) ™ AS-300; AGC Chemicals Americas Inc., Exton, PA), 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether (HFE-347pc-f; AsahiKlin) ™ AE-3000; AGC Chemicals), cyclohexane, cyclopentane, n-heptane, n-hexane, acetone, methyl acetate, methylcyclohexane, 2,3-dihydrodecafluoropentane (HFC-43-10mee; Vertrel) ™ XF; The Chemours Company, Wilmington, DE), cis-1,1,1,4,4,4-hexafluoro-2-butene (HFO-1336mzzZ), methyl nonafluorobutyl ether (Novec) ™ 7100,3M), ethoxy-nonafluorobutane (Novec) ™ 7200; 3M), heptafluorocyclopentane, methyl ethyl ketone, dimethyl carbonate and trimethylpentane.

[0101] A known amount of HFO was placed in a boiling point meter and heated to atmospheric boiling point, and the boiling point was recorded. A known amount of the second component was added, and the boiling point of the blend was recorded after each addition. Mixtures showing boiling points lower than the boiling points of both components were azeotropic. The results are shown in Table 1. Table 1 Screening of Binary Azeotropic Behavior

[0102]

[0103] Both E-HFO-153-10mczz and E-HFO-153-10mzzy exhibited azeotropic behavior with PEIK, HCFO-1233ydZ, HFE-347pc-f, cyclohexane, and cyclopentane. E-HFO-153-10mzzy also showed azeotropic behavior with n-heptane, n-hexane, acetone, methyl acetate, and methylcyclohexane. Other tested solvents did not show azeotropic behavior with E-HFO-153-10mzzy. Example 2

[0104] Azeotropic binary mixtures of E-HFO-153-10mczz and PEIK were screened using a boiling point meter. A known amount of E-HFO-153-10mczz was poured into a boiling point meter and heated to the atmospheric boiling point, which was recorded. A known amount of PEIK was added, and the boiling point was allowed to equilibrate, and then recorded. This process was repeated for a series of binary compositions.

[0105] Figure 1 A graph showing boiling point as a function of composition is shown. At a pressure of about 101 kPa, the binary mixture of E-HFO-153-10mczz and PEIK is at least azeotropic or azeotropic-like (with boiling points in the range of about 48.5°C to about 48.8°C) in the range of about 24 wt% PEIK to about 63 wt% PEIK, and alternatively in the range of about 34 wt% PEIK to about 57 wt% PEIK (with boiling points in the range of about 48.5°C to about 48.7°C), or any value, range, or subrange in between. Example 3

[0106] Azeotropic binary mixtures of E-HFO-153-10mczz and HCFO-1233ydZ were screened using a boiling point meter. A known amount of E-HFO-153-10mczz was poured into a boiling point meter and heated to its atmospheric boiling point, which was recorded. A known amount of HCFO-1233ydZ was added, and the boiling point was allowed to equilibrate, and then recorded. This process was repeated for a series of binary compositions.

[0107] Figure 2 A graph showing boiling point as a function of composition is shown. At a pressure of about 101 kPa, the binary mixture of E-HFO-153-10mczz and HCFO-1233ydZ is at least an azeotropic or azeotropic-like mixture in the range of about 17 wt% HCFO-1233ydZ to about 46 wt% HCFO-1233ydZ (with a boiling point in the range of about 44.4°C to about 45.1°C), alternatively in the range of about 22 wt% HCFO-1233ydZ to about 40 wt% HCFO-1233ydZ (with a boiling point in the range of about 44.4°C to about 44.8°C), or any value, range, or subrange between them. Example 4

[0108] Azeotropic binary mixtures of E-HFO-153-10mczz and HFE-347pc-f were screened using a boiling point meter. A known amount of E-HFO-153-10mczz was poured into a boiling point meter and heated to the atmospheric boiling point, which was recorded. A known amount of HFE-347pc-f was added, and the boiling point was allowed to equilibrate, and then recorded. This process was repeated for a series of binary compositions.

[0109] Figure 3 A graph showing boiling point as a function of composition is shown. At a pressure of about 101 kPa, the binary mixture of E-HFO-153-10mczz and HFE-347pc-f is at least an azeotropic or azeotropic-like mixture in the range of about 9 wt% HFE-347pc-f to about 46 wt% HFE-347pc-f (with a boiling point in the range of about 50.5°C to about 51.5°C), alternatively in the range of about 16 wt% HFE-347pc-f to about 40 wt% HFE-347pc-f (with a boiling point in the range of about 50.5°C to about 51.0°C), or any value, range, or subrange between them. Example 5

[0110] Azeotropic binary mixtures of E-HFO-153-10mczz and cyclohexane were screened using a boiling point meter. A known amount of E-HFO-153-10mczz was poured into a boiling point meter and heated to the atmospheric boiling point, which was recorded. A known amount of cyclohexane was added, and the boiling point was allowed to equilibrate, and then recorded. This process was repeated for a series of binary compositions.

[0111] Figure 4 A graph showing boiling point as a function of composition is shown. At a pressure of about 101 kPa, the binary mixture of E-HFO-153-10mczz and cyclohexane is azeotropic or azeotropic-like (with boiling points in the range of about 5 wt% cyclohexane to about 16 wt% cyclohexane), alternatively azeotropic or azeotropic (with boiling points in the range of about 46.4 °C to about 46.9 °C), or any value, range, or subrange thereof, in the range of about 6 wt% cyclohexane to about 14 wt% cyclohexane. Example 6

[0112] Azeotropic binary mixtures of E-HFO-153-10mzzy and PEIK were screened using a boiling point meter. A known amount of E-HFO-153-10mzzy was poured into a boiling point meter and heated to the atmospheric boiling point, which was recorded. A known amount of PEIK was added, and the boiling point was allowed to equilibrate, and then recorded. This process was repeated for a series of binary compositions.

[0113] Figure 5 A graph showing boiling point as a function of composition is shown. At a pressure of about 101 kPa, the binary mixture of E-HFO-153-10mzzy and PEIK is at least azeotropic or azeotropic-like (with boiling points in the range of about 40 wt% PEIK to about 90 wt% PEIK), alternatively azeotropic or azeotropic-like (with boiling points in the range of about 55 wt% PEIK to about 82 wt% PEIK), or any value, range, or subrange between them. Example 7

[0114] Azeotropic binary mixtures of E-HFO-153-10mzzy and HCFO-1233ydZ were screened using a boiling point meter. A known amount of E-HFO-153-10mzzy was poured into the boiling point meter and heated to its atmospheric boiling point, which was then recorded. A known amount of HCFO-1233ydZ was added, and the boiling point was allowed to equilibrate, and then recorded. This process was repeated for a series of binary compositions.

[0115] Figure 6 A graph showing boiling point as a function of composition is shown. At a pressure of about 101 kPa, the binary mixture of E-HFO-153-10mzzy and HCFO-1233ydZ is at least an azeotropic or azeotropic-like mixture in the range of about 7 wt% HCFO-1233ydZ to about 45 wt% HCFO-1233ydZ (with a boiling point in the range of about 43.7°C to about 44.5°C), alternatively in the range of about 22 wt% HCFO-1233ydZ to about 40 wt% HCFO-1233ydZ (with a boiling point in the range of about 43.7°C to about 44.2°C), or any value, range, or subrange between them. Example 8

[0116] Azeotropic binary mixtures of E-HFO-153-10mzzy and HFE-347pc-f were screened using a boiling point meter. A known amount of E-HFO-153-10mzzy was poured into a boiling point meter and heated to its atmospheric boiling point, which was recorded. A known amount of HFE-347pc-f was added, and the boiling point was allowed to equilibrate, and then recorded. This process was repeated for a series of binary compositions.

[0117] Figure 7A graph showing boiling point as a function of composition is shown. At a pressure of about 101 kPa, the binary mixture of E-HFO-153-10mzzy and HFE-347pc-f is at least an azeotropic or azeotropic-like mixture in the range of about 8 wt% HFE-347pc-f to about 35 wt% HFE-347pc-f (with a boiling point in the range of about 47.9 °C to about 48.2 °C), alternatively in the range of about 9 wt% HFE-347pc-f to about 32 wt% HFE-347pc-f (with a boiling point in the range of about 47.9 °C to about 48.1 °C), or any value, range, or subrange between them. Example 9

[0118] Azeotropic binary mixtures of E-HFO-153-10mzzy and cyclohexane were screened using a boiling point meter. A known amount of E-HFO-153-10mzzy was poured into a boiling point meter and heated to its atmospheric boiling point, which was recorded. A known amount of cyclohexane was added, and the boiling point was allowed to equilibrate, and then recorded. This process was repeated for a series of binary compositions.

[0119] Figure 8 A graph showing boiling point as a function of composition is shown. At a pressure of about 101 kPa, the binary mixture of E-HFO-153-10mzzy and cyclohexane is azeotropic or azeotropic-like (with boiling points in the range of about 5.5 wt% cyclohexane to about 18.8 wt% cyclohexane), alternatively in the range of about 6.5 wt% cyclohexane to about 16.2 wt% cyclohexane (with boiling points in the range of about 46.6 °C to about 46.8 °C), or any value, range, or subrange in between. Example 10

[0120] Azeotropic binary mixtures of E-HFO-153-10mzzy and n-heptane were screened using a boiling point meter. A known amount of E-HFO-153-10mzzy was poured into a boiling point meter and heated to its atmospheric boiling point, which was recorded. A known amount of n-heptane was added, and the boiling point was allowed to equilibrate, and then recorded. This process was repeated for a series of binary compositions.

[0121] Figure 9 A graph showing boiling point as a function of composition is shown. At a pressure of about 101 kPa, the binary mixture of E-HFO-153-10mzzy and n-heptane is azeotropic or azeotropic-like, with a boiling point ranging from about 1.4 wt% n-heptane to about 3.4 wt% n-heptane, and its boiling point is in the range of about 48.5 °C to about 48.7 °C. Example 11

[0122] Azeotropic binary mixtures of E-HFO-153-10mzzy and n-hexane were screened using a boiling point meter. A known amount of E-HFO-153-10mzzy was poured into a boiling point meter and heated to its atmospheric boiling point, which was recorded. A known amount of n-hexane was added, and the boiling point was allowed to equilibrate, and then recorded. This process was repeated for a series of binary compositions.

[0123] Figure 10 A graph showing boiling point as a function of composition is shown. At a pressure of about 101 kPa, the binary mixture of E-HFO-153-10mzzy and n-hexane is azeotropic or azeotropic-like (with boiling points in the range of about 7 wt% n-hexane to about 29 wt% n-hexane), alternatively azeotropic or azeotropic (with boiling points in the range of about 44.3 °C to about 44.9 °C), or any value, range, or subrange thereof, in the range of about 8 wt% n-hexane to about 23 wt% n-hexane. Example 12

[0124] Azeotropic binary mixtures of E-HFO-153-10mzzy and acetone were screened using a boiling point meter. A known amount of E-HFO-153-10mzzy was poured into a boiling point meter and heated to atmospheric boiling point, which was recorded. A known amount of acetone was added, and the boiling point was allowed to equilibrate, and then recorded. This process was repeated for a series of binary compositions.

[0125] Figure 11 A graph showing boiling point as a function of composition is shown. At a pressure of about 101 kPa, the binary mixture of E-HFO-153-10mzzy and acetone is azeotropic or azeotropic-like (with boiling points in the range of about 9 wt% acetone to about 25 wt% acetone), alternatively azeotropic or azeotropic (with boiling points in the range of about 46.4 °C to about 46.9 °C), or any value, range, or subrange thereof, in the range of about 10.5 wt% acetone to about 21 wt% acetone. Example 13

[0126] Azeotropic binary mixtures of E-HFO-153-10mzzy and methyl acetate were screened using a boiling point meter. A known amount of E-HFO-153-10mzzy was poured into a boiling point meter and heated to atmospheric boiling point, which was recorded. A known amount of methyl acetate was added, and the boiling point was allowed to equilibrate, and then recorded. This process was repeated for a series of binary compositions.

[0127] Figure 12 A graph showing boiling point as a function of composition is shown. At a pressure of about 101 kPa, the binary mixture of E-HFO-153-10mzzy and methyl acetate is azeotropic or azeotropic-like (with boiling points in the range of about 47.3°C to about 47.8°C) at least in the range of about 11.3 wt% methyl acetate to about 34 wt% methyl acetate, and alternatively in the range of about 15.6 wt% methyl acetate to about 31 wt% methyl acetate (with boiling points in the range of about 47.3°C to about 47.6°C), or any value, range, or subrange between them. Example 14

[0128] Azeotropic binary mixtures of E-HFO-153-10mzzy and methylcyclohexane were screened using a boiling point meter. A known amount of E-HFO-153-10mzzy was poured into a boiling point meter and heated to atmospheric boiling point, which was recorded. A known amount of methylcyclohexane was added, and the boiling point was allowed to equilibrate, and then recorded. This process was repeated for a series of binary compositions.

[0129] Figure 13 A graph showing boiling point as a function of composition is shown. At a pressure of approximately 101 kPa, the binary mixture of E-HFO-153-10mzzy and methylcyclohexane is azeotropic or azeotropic-like, with a boiling point ranging from approximately 1.5 wt% methylcyclohexane to approximately 2.8 wt% methylcyclohexane, and its boiling point is in the range of approximately 49.3 °C to approximately 49.5 °C. Example 15

[0130] Azeotropic binary mixtures of E-HFO-153-10mzzy and hexafluoropropyl methyl ether (HFPME) were screened using a boiling point meter. A known amount of E-HFO-153-10mzzy was poured into a boiling point meter and heated to atmospheric boiling point, which was recorded. A known amount of HFPME was added, and the boiling point was allowed to equilibrate, and then recorded. This process was repeated for a series of binary compositions.

[0131] Figure 14 A graph showing boiling point as a function of composition is shown. At a pressure of about 101 kPa, the binary mixture of E-HFO-153-10mzzy and HFPME is azeotropic or azeotropic-like (with boiling points in the range of about 9 wt% HFPME to about 30 wt% HFPME), alternatively in the range of about 16 wt% HFPME to about 26 wt% HFPME (with boiling points in the range of about 48.3 °C to about 48.5 °C), or any value, range, or subrange in between. Example 16

[0132] A ternary azeotrope containing E-HFO-153-10mzzy, HFE-347pc-f, and cyclohexane was determined using an atmospheric distillation experiment, starting with the initial ternary composition listed in Table 2, at approximately 101 kPa using a 20-plate Vigreux distillation column. Distillation was allowed to proceed with reflux through the column for one hour, and the first 10% fraction was collected and its composition analyzed by gas chromatography / flame ionization detection (GC / FID). Table 2. Ternary compositions of E-HFO-153-10mzzy, HFE-347pc-f, and cyclohexane.

[0133]

[0134] The ternary composition exhibits azeotropic behavior because the blend cannot be effectively separated by fractionation. Furthermore, the boiling point and dew point of the mixture are lower than those of either of the components or the binary compound.

[0135] A ternary mixture of azeotropic components (72 wt% E-HFO-153-10mzzy, 18.5 wt% HFE-347pc-f, and 9.5 wt% cyclohexane) was prepared, and the dielectric constant was measured according to ASTM D924, and the volume resistivity was measured according to ASTM D1169. The dielectric constant was 2.38 F / m, and the volume resistivity was 8.37 × 10⁻⁶. 11 It has an Ω-cm dielectric property comparable to commercially available fluorinated compounds, while also reducing operating temperature and boiling point.

[0136] A ternary mixture of azeotropic compositions (72 wt% E-HFO-153-10mzzy, 18.5 wt% HFE-347pc-f, and 9.5 wt% cyclohexane) was prepared, and its flash point was tested in a closed cup according to ASTM D56 label specifications. The mixture did not exhibit a flash point in the range of -15°C to 46°C. Example 17

[0137] A ternary azeotrope containing E-HFO-153-10mzzy, HCFO-1233ydZ, and n-hexane was determined using an atmospheric distillation experiment, starting with the initial ternary composition listed in Table 2, at approximately 101 kPa using a 20-plate Vigreux distillation column. Distillation allowed for reflux through the column for one hour, and the first 10% fraction was collected and its composition analyzed by GC / FID. Table 3. Ternary compositions of E-HFO-153-10mzzy, HCFO-1233ydZ and n-hexane

[0138]

[0139] The ternary composition exhibits azeotropic behavior because the blend cannot be effectively separated by fractionation. Furthermore, the boiling point and dew point of the mixture are lower than those of either of the components or the binary compound. Example 18

[0140] A ternary azeotrope containing E-HFO-153-10mzzy, HCFO-1233ydZ, and cyclohexane was determined using an atmospheric distillation experiment, starting with the initial ternary composition listed in Table 2, at approximately 101 kPa using a 20-plate Vigreux distillation column. Distillation allowed for reflux through the column for one hour, and the first 10% fraction was collected and its composition analyzed by GC / FID. Table 4. Ternary compositions of E-HFO-153-10mzzy, HCFO-1233ydZ and cyclohexane.

[0141]

[0142] The ternary composition exhibits azeotropic behavior because the blend cannot be effectively separated by fractionation. Furthermore, the boiling point and dew point of the mixture are lower than those of either of the components or the binary compound. Other implementation plans

[0143] Implementation Scheme 1: A composition comprising: i) bis(perfluoroalkyl)ethylene; and ii) at least one additional compound; wherein the bis(perfluoroalkyl)ethylene and the at least one additional compound are present in the composition in an amount that effectively forms an azeotropic composition or an azeotropic-like composition.

[0144] Implementation Scheme 2: The composition according to Implementation Scheme 1, wherein the bis(perfluoroalkyl)ethylene and the at least one additional compound are at least 98% by weight based on the weight of the composition.

[0145] Implementation Scheme 3: The composition according to Implementation Scheme 1, wherein the bis(perfluoroalkyl)ethylene and the at least one additional compound are at least 99% by weight based on the weight of the composition.

[0146] Implementation Scheme 4: The composition according to Implementation Scheme 1, wherein the composition is substantially composed of the bis(perfluoroalkyl)ethylene and the at least one additional compound.

[0147] Implementation Scheme 5: The composition according to Implementation Scheme 1, wherein the bis(perfluoroalkyl)ethylene has the formula (1):

[0148] CHR1=CHR2(1)

[0149] Where R1 and R2 are independently of equation C n F 2n+1Straight-chain or branched perfluorinated carbon, where n is an integer in the range of 1 to 5.

[0150] Implementation Scheme 6: The composition according to Implementation Scheme 1, wherein the bis(perfluoroalkyl)ethylene is selected from the group consisting of: E-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (E-HFO-153-10mczz) and E-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)-2-pentene (E-HFO-153-10mzzy).

[0151] Implementation Scheme 7: The composition according to Implementation Scheme 6, wherein the bis(perfluoroalkyl)ethylene comprises E-HFO-153-10mczz.

[0152] Implementation Scheme 8: The composition according to Implementation Scheme 7, wherein the at least one additional compound is selected from the group consisting of: perfluoroethyl isopropyl ketone, cis-1-chloro-2,3,3-trifluoropropene, 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether, cyclohexane, cyclopentane, and combinations thereof.

[0153] Implementation Scheme 9: The composition according to Implementation Scheme 7, wherein the at least one additional compound comprises perfluoroethyl isopropyl ketone, and the composition comprises about 37% to about 76% of E-HFO-153-10mczz and about 24% to about 63% of perfluoroethyl isopropyl ketone by weight of the composition.

[0154] Implementation Scheme 10: The composition according to Implementation Scheme 7, wherein the at least one additional compound comprises cis-1-chloro-2,3,3-trifluoropropene, and the composition comprises about 54% to about 83% E-HFO-153-10mczz and about 17% to about 46% cis-1-chloro-2,3,3-trifluoropropene by weight of the composition.

[0155] Embodiment 11: The composition according to Embodiment 7, wherein the at least one additional compound comprises 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether, and the composition comprises about 54% to about 91% E-HFO-153-10mczz and about 9% to about 46% 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether by weight of the composition.

[0156] Implementation Scheme 12: The composition according to Implementation Scheme 7, wherein the at least one additional compound comprises cyclohexane, and the composition comprises about 84% to about 95% E-HFO-153-10mczz and about 5% to about 16% cyclohexane by weight of the composition.

[0157] Implementation Scheme 13: The composition according to Implementation Scheme 7, wherein the at least one additional compound comprises cyclopentane, and the composition comprises about 53% to about 79% E-HFO-153-10mczz and about 21% to about 47% cyclopentane by weight of the composition.

[0158] Implementation Scheme 14: The composition according to Implementation Scheme 7, wherein the composition has a boiling point of about 35°C to about 49°C at a pressure of about 101 kPa.

[0159] Implementation Scheme 15: The composition according to Implementation Scheme 6, wherein the bis(perfluoroalkyl)ethylene comprises E-HFO-153-10mzzy.

[0160] Implementation Scheme 16: The composition according to Implementation Scheme 15, wherein the at least one additional compound is selected from the group consisting of: perfluoroethyl isopropyl ketone, cis-1-chloro-2,3,3-trifluoropropene, 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether, cyclohexane, cyclopentane, n-heptane, n-hexane, acetone, methyl acetate, methylcyclohexane, HFPME, and combinations thereof.

[0161] Embodiment 17: The composition according to Embodiment 15, wherein the at least one additional compound comprises perfluoroethyl isopropyl ketone, and the composition comprises about 10% to about 60% of E-HFO-153-10mzzy and about 40% to about 90% of perfluoroethyl isopropyl ketone by weight of the composition.

[0162] Embodiment 18: The composition according to Embodiment 15, wherein the at least one additional compound comprises cis-1-chloro-2,3,3-trifluoropropene, and the composition comprises about 55% to about 83% E-HFO-153-10mzzy and about 17% to about 45% cis-1-chloro-2,3,3-trifluoropropene by weight of the composition.

[0163] Embodiment 19: The composition according to Embodiment 15, wherein the at least one additional compound comprises 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether, and the composition comprises about 65% to about 92% E-HFO-153-10mzzy and about 8% to about 35% 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether by weight of the composition.

[0164] Embodiment 20: The composition according to Embodiment 15, wherein the at least one additional compound comprises cyclohexane, and the composition comprises about 81.2% to about 94.5% E-HFO-153-10mzzy and about 5.5% to about 18.8% cyclohexane by weight of the composition.

[0165] Implementation Scheme 21: The composition according to Implementation Scheme 15, wherein the at least one additional compound comprises cyclopentane, and the composition comprises about 52% to about 84% E-HFO-153-10mzzy and about 16% to about 48% cyclopentane by weight of the composition.

[0166] Embodiment 22: The composition according to Embodiment 15, wherein the at least one additional compound comprises n-heptane, and the composition comprises about 96.6% to about 98.6% of E-HFO-153-10mzzy and about 1.4% to about 3.4% of n-heptane by weight of the composition.

[0167] Implementation Scheme 23: The composition according to Implementation Scheme 15, wherein the at least one additional compound comprises n-hexane, and the composition comprises about 71% to about 93% of E-HFO-153-10mzzy and about 7% to about 29% of n-hexane by weight of the composition.

[0168] Implementation Scheme 24: The composition according to Implementation Scheme 15, wherein the at least one additional compound comprises acetone, and the composition comprises about 75% to about 91% E-HFO-153-10mzzy and about 9% to about 25% acetone by weight of the composition.

[0169] Embodiment 25: The composition according to Embodiment 15, wherein the at least one additional compound comprises methyl acetate, and the composition comprises about 66% to about 88.7% E-HFO-153-10mzzy and about 11.3% to about 34% methyl acetate by weight of the composition.

[0170] Embodiment 26: The composition according to Embodiment 15, wherein the at least one additional compound comprises methylcyclohexane, and the composition comprises about 97.2% to about 98.5% E-HFO-153-10mzzy and about 1.5% to about 2.8% methylcyclohexane by weight of the composition.

[0171] Embodiment 27: The composition according to Embodiment 15, wherein the at least one additional compound comprises methylcyclohexane and cyclohexane, and the composition comprises about 70% to about 74% E-HFO-153-10mzzy, about 18% to about 19% 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether and about 8% to about 11% cyclohexane by weight.

[0172] Embodiment 28: The composition according to Embodiment 15, wherein the at least one additional compound comprises cis-1-chloro-2,3,3-trifluoropropene and n-hexane, and the composition comprises about 68% to about 72% E-HFO-153-10mzzy, about 20% to about 21.5% cis-1-chloro-2,3,3-trifluoropropene and about 9% to about 10% n-hexane by weight.

[0173] Embodiment 29: The composition according to Embodiment 15, wherein the at least one additional compound comprises cis-1-chloro-2,3,3-trifluoropropene and cyclohexane, and the composition comprises about 69% to about 73% E-HFO-153-10mzzy, about 23% to about 26% cis-1-chloro-2,3,3-trifluoropropene and about 4% to about 5% cyclohexane by weight of the composition.

[0174] Implementation Scheme 30: The composition according to Implementation Scheme 15, wherein the composition has a boiling point of about 35°C to about 49°C at a pressure of about 101 kPa.

[0175] Implementation Scheme 31: A method of coating a surface, the method comprising: dissolving a coating composition in a carrier liquid to form a solution, the carrier liquid comprising bis(perfluoroalkyl)ethylene and at least one additional compound present in an amount of an azeotropic composition or azeotropic-like composition that effectively forms the carrier liquid; applying the solution to the surface; and removing the carrier liquid from the coating composition to coat the surface with the coating composition.

[0176] Implementation Scheme 32: The method according to Implementation Scheme 31, wherein the bis(perfluoroalkyl)ethylene has the formula (1):

[0177] CHR1=CHR2(1)

[0178] Where R1 and R2 are independently of equation C n F 2n+1 Straight-chain or branched perfluorinated carbon, where n is an integer in the range of 1 to 5.

[0179] Implementation Scheme 33: The method according to Implementation Scheme 31, wherein the bis(perfluoroalkyl)ethylene is selected from the group consisting of: E-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (E-HFO-153-10mczz) and E-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)-2-pentene (E-HFO-153-10mzzy).

[0180] Implementation Scheme 34: The method according to Implementation Scheme 31, wherein the at least one additional compound is selected from the group consisting of: perfluoroethyl isopropyl ketone, cis-1-chloro-2,3,3-trifluoropropene, 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether, cyclohexane, cyclopentane, n-heptane, n-hexane, acetone, methyl acetate, methylcyclohexane, hexafluoropropyl methyl ether, and combinations thereof.

[0181] Implementation Scheme 35: The method according to Implementation Scheme 31, wherein the coating composition comprises a perfluoropolyether.

[0182] Implementation Scheme 36: A method for cooling a system, the method comprising two-phase immersion cooling of the system with a coolant comprising bis(perfluoroalkyl)ethylene and at least one additional compound present in an amount that effectively forms an azeotropic composition or azeotropic-like composition of the coolant.

[0183] Implementation Scheme 37: The method according to Implementation Scheme 36, wherein the bis(perfluoroalkyl)ethylene has the formula (1):

[0184] CHR1=CHR2(1)

[0185] Where R1 and R2 are independently of equation C n F 2n+1 Straight-chain or branched perfluorinated carbon, where n is an integer in the range of 1 to 5.

[0186] Implementation Scheme 38: The method according to Implementation Scheme 36, wherein the bis(perfluoroalkyl)ethylene is selected from the group consisting of: E-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (E-HFO-153-10mczz) and E-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)-2-pentene (E-HFO-153-10mzzy).

[0187] Implementation Scheme 39: The method according to Implementation Scheme 36, wherein the at least one additional compound is selected from the group consisting of: perfluoroethyl isopropyl ketone, cis-1-chloro-2,3,3-trifluoropropene, 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether, cyclohexane, cyclopentane, n-heptane, n-hexane, acetone, methyl acetate, methylcyclohexane, hexafluoropropyl methyl ether, and combinations thereof.

[0188] Implementation Scheme 40: A method for cleaning a surface, the method comprising contacting a composition with the surface, the composition comprising bis(perfluoroalkyl)ethylene and at least one additional compound present in an amount that effectively forms the composition as an azeotrope or azeotrope.

[0189] Implementation Scheme 41: The method according to Implementation Scheme 40, wherein the bis(perfluoroalkyl)ethylene has the formula (1):

[0190] CHR1=CHR2(1)

[0191] Where R1 and R2 are independently of equation C n F 2n+1 Straight-chain or branched perfluorinated carbon, where n is an integer in the range of 1 to 5.

[0192] Implementation Scheme 42: The method according to Implementation Scheme 40, wherein the bis(perfluoroalkyl)ethylene is selected from the group consisting of: E-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (E-HFO-153-10mczz) and E-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)-2-pentene (E-HFO-153-10mzzy).

[0193] Implementation Scheme 43: The method according to Implementation Scheme 40, wherein the at least one additional compound is selected from the group consisting of: perfluoroethyl isopropyl ketone, cis-1-chloro-2,3,3-trifluoropropene, 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether, cyclohexane, cyclopentane, n-heptane, n-hexane, acetone, methyl acetate, methylcyclohexane, hexafluoropropyl methyl ether, and combinations thereof.

[0194] All of the above references are incorporated herein by reference.

[0195] It should be understood that although the invention has been described in conjunction with a detailed description, the foregoing description is intended to illustrate and not limit the scope of the invention, which is defined by the appended claims. Other aspects, advantages, and modifications are within the scope of the following claims. Those skilled in the art to which this invention pertains will understand that any feature of any particular aspect and / or embodiment of the invention described herein may be combined with one or more features of any other aspect and / or embodiment of the invention described herein, modified where appropriate to ensure compatibility of the combination. Such combinations are considered part of the invention contemplated by this disclosure.

Claims

1. A composition comprising: i) bis(perfluoroalkyl)ethylene; and ii) At least one additional compound; The bis(perfluoroalkyl)ethylene and the at least one additional compound are present in the composition in an amount that effectively forms an azeotropic composition or an azeotropic-like composition.

2. The composition according to claim 1, wherein the bis(perfluoroalkyl)ethylene and the at least one additional compound constitute at least 98% by weight of the composition.

3. The composition according to claim 1, wherein the bis(perfluoroalkyl)ethylene is selected from the group consisting of: E-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (E-HFO-153-10mczz) and E-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)-2-pentene (E-HFO-153-10mzzy).

4. The composition according to claim 3, wherein the bis(perfluoroalkyl)ethylene comprises E-HFO-153-10mczz.

5. The composition according to claim 4, wherein the at least one additional compound is selected from the group consisting of: perfluoroethyl isopropyl ketone, cis-1-chloro-2,3,3-trifluoropropene, 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether, cyclohexane, cyclopentane, and combinations thereof.

6. The composition of claim 4, wherein the at least one additional compound comprises perfluoroethyl isopropyl ketone, and the composition comprises about 37% to about 76% E-HFO-153-10mczz and about 24% to about 63% perfluoroethyl isopropyl ketone by weight of the composition.

7. The composition of claim 4, wherein the at least one additional compound comprises cis-1-chloro-2,3,3-trifluoropropene, and the composition comprises about 54% to about 83% E-HFO-153-10mczz and about 17% to about 46% cis-1-chloro-2,3,3-trifluoropropene by weight of the composition.

8. The composition of claim 4, wherein the at least one additional compound comprises 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether, and the composition comprises about 54% to about 91% E-HFO-153-10mczz and about 9% to about 46% 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether by weight of the composition.

9. The composition of claim 4, wherein the at least one additional compound comprises cyclohexane, and the composition comprises about 84% to about 95% E-HFO-153-10mczz and about 5% to about 16% cyclohexane by weight of the composition.

10. The composition of claim 4, wherein the at least one additional compound comprises cyclopentane, and the composition comprises about 53% to about 79% E-HFO-153-10mczz and about 21% to about 47% cyclopentane by weight of the composition.

11. The composition according to claim 4, wherein the composition has a boiling point of about 35°C to about 49°C at a pressure of about 101 kPa.

12. The composition according to claim 3, wherein the bis(perfluoroalkyl)ethylene comprises E-HFO-153-10mzzy.

13. The composition of claim 12, wherein the at least one additional compound is selected from the group consisting of: perfluoroethyl isopropyl ketone, cis-1-chloro-2,3,3-trifluoropropene, 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether, cyclohexane, cyclopentane, n-heptane, n-hexane, acetone, methyl acetate, methylcyclohexane, hexafluoropropyl methyl ether (HFPME), and combinations thereof.

14. The composition of claim 13, wherein the at least one additional compound comprises perfluoroethyl isopropyl ketone, and the composition comprises about 10% to about 60% E-HFO-153-10mzzy and about 40% to about 90% perfluoroethyl isopropyl ketone by weight of the composition.

15. The composition of claim 13, wherein the at least one additional compound comprises cis-1-chloro-2,3,3-trifluoropropene, and the composition comprises about 55% to about 83% E-HFO-153-10mzzy and about 17% to about 45% cis-1-chloro-2,3,3-trifluoropropene by weight of the composition.

16. The composition of claim 13, wherein the at least one additional compound comprises 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether, and the composition comprises about 65% to about 92% E-HFO-153-10mzzy and about 8% to about 35% 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether by weight of the composition.

17. The composition of claim 13, wherein the at least one additional compound comprises cyclohexane, and the composition comprises about 81.2% to about 94.5% E-HFO-153-10mzzy and about 5.5% to about 18.8% cyclohexane by weight of the composition.

18. The composition of claim 13, wherein the at least one additional compound comprises cyclopentane, and the composition comprises about 52% to about 84% E-HFO-153-10mzzy and about 16% to about 48% cyclopentane by weight of the composition.

19. The composition of claim 13, wherein the at least one additional compound comprises n-heptane, and the composition comprises about 96.6% to about 98.6% of E-HFO-153-10mzzy and about 1.4% to about 3.4% of n-heptane by weight of the composition.

20. The composition of claim 13, wherein the at least one additional compound comprises n-hexane, and the composition comprises about 71% to about 93% E-HFO-153-10mzzy and about 7% to about 29% n-hexane by weight of the composition.

21. The composition of claim 13, wherein the at least one additional compound comprises acetone, and the composition comprises about 75% to about 91% E-HFO-153-10mzzy and about 9% to about 25% acetone by weight of the composition.

22. The composition of claim 13, wherein the at least one additional compound comprises methyl acetate, and the composition comprises about 66% to about 88.7% E-HFO-153-10mzzy and about 11.3% to about 34% methyl acetate by weight of the composition.

23. The composition of claim 13, wherein the at least one additional compound comprises methylcyclohexane, and the composition comprises about 97.2% to about 98.5% E-HFO-153-10mzzy and about 1.5% to about 2.8% methylcyclohexane by weight of the composition.

24. The composition of claim 13, wherein the at least one additional compound comprises HFPME, and the composition comprises about 70% to about 91% E-HFO-153-10mzzy and about 9% to about 30% HFPME by weight of the composition.

25. The composition of claim 13, wherein the at least one additional compound comprises methylcyclohexane and cyclohexane, and the composition comprises about 70% to about 74% E-HFO-153-10mzzy, about 18% to about 19% 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether and about 8% to about 11% cyclohexane by weight.

26. The composition of claim 13, wherein the at least one additional compound comprises cis-1-chloro-2,3,3-trifluoropropene and n-hexane, and the composition comprises, by weight of the composition, about 68% to about 72% E-HFO-153-10mzzy, about 20% to about 21.5% cis-1-chloro-2,3,3-trifluoropropene and about 9% to about 10% n-hexane.

27. The composition of claim 13, wherein the at least one additional compound comprises cis-1-chloro-2,3,3-trifluoropropene and cyclohexane, and the composition comprises, by weight of the composition, about 69% to about 73% of E-HFO-153-10mzzy, about 23% to about 26% of cis-1-chloro-2,3,3-trifluoropropene and about 4% to about 5% of cyclohexane.

28. The composition according to claim 13, wherein the composition has a boiling point of about 35°C to about 49°C at a pressure of about 101 kPa.

29. A method for coating a surface, the method comprising: The coating composition is dissolved in a carrier liquid to form a solution, said carrier liquid comprising bis(perfluoroalkyl)ethylene and at least one additional compound in an amount of an azeotropic composition or azeotropic-like composition that effectively forms the carrier liquid. The solution is applied to the surface; as well as Remove the carrier liquid from the coating composition to coat the surface with the coating composition.

30. The method of claim 29, wherein the bis(perfluoroalkyl)ethylene is selected from the group consisting of: E-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (E-HFO-153-10mczz) and E-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)-2-pentene (E-HFO-153-10mzzy).

31. The method of claim 29, wherein the at least one additional compound is selected from the group consisting of: perfluoroethyl isopropyl ketone, cis-1-chloro-2,3,3-trifluoropropene, 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether, cyclohexane, cyclopentane, n-heptane, n-hexane, acetone, methyl acetate, methylcyclohexane, hexafluoropropyl methyl ether, and combinations thereof.

32. The method of claim 29, wherein the coating composition comprises a perfluoropolyether.

33. A method for cooling a system, the method comprising two-phase immersion cooling of the system with a coolant comprising bis(perfluoroalkyl)ethylene and at least one additional compound present in an amount that effectively forms an azeotropic composition or azeotropic-like composition of the coolant.

34. The method of claim 33, wherein the bis(perfluoroalkyl)ethylene is selected from the group consisting of: E-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (E-HFO-153-10mczz) and E-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)-2-pentene (E-HFO-153-10mzzy).

35. The method of claim 33, wherein the at least one additional compound is selected from the group consisting of: perfluoroethyl isopropyl ketone, cis-1-chloro-2,3,3-trifluoropropene, 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether, cyclohexane, cyclopentane, n-heptane, n-hexane, acetone, methyl acetate, methylcyclohexane, hexafluoropropyl methyl ether, and combinations thereof.

36. A method for cleaning a surface, the method comprising contacting a composition with the surface, the composition comprising bis(perfluoroalkyl)ethylene and at least one additional compound present in an amount that effectively forms the composition as an azeotrope or azeotrope.

37. The method of claim 36, wherein the bis(perfluoroalkyl)ethylene is selected from the group consisting of: E-1,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (E-HFO-153-10mczz) and E-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)-2-pentene (E-HFO-153-10mzzy).

38. The method of claim 36, wherein the at least one additional compound is selected from the group consisting of: perfluoroethyl isopropyl ketone, cis-1-chloro-2,3,3-trifluoropropene, 1,1,1,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether, cyclohexane, cyclopentane, n-heptane, n-hexane, acetone, methyl acetate, methylcyclohexane, hexafluoropropyl methyl ether, and combinations thereof.

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