Azeotropic compositions comprising a bis(perfluoroalkyl)ethylene and uses thereof

Abstract

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

Description

TITLE OF THE INVENTIONAZEOTROPIC COMPOSITIONS COMPRISING A BIS(PERFLUOROALKYL)ETHYLENE AND USES THEREOFTECHNICAL FIELD

[0001] The present disclosure relates to azeotropic or azeotrope-like compositions including a bis(perfluoroalkyl)ethylene and at least one additional compound. The compositions described herein may be useful, for example, in precision cleaning and heat transfer applications and as carrier fluids.BACKGROUND

[0002] Fluorochemicals, such as perfluorocarbon (PFC), hydrofluorocarbon (HFC), and hydrofluoroether (HFE) compounds, have been used extensively in demanding applications such as precision cleaning, heat transfer, and carrier fluid applications due to high thermal stability, relatively low toxicity, and non-flammability. These fluorochemicals offer unique properties such as high density and low surface tension.

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

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

[0005] Thus, there is a need for new low GWP formulations that are more direct replacements for existing fluorochemicals with boiling points in the 40 °C to 60 °C range.SUMMARY

[0006] The present disclosure provides, inter alia, a composition, comprising: i) a 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 amounts effective to form an azeotropic composition or an azeotrope-like composition.

[0007] The present disclosure also provides a process of coating a surface, comprising: dissolving a coating composition in a carrier fluid, the carrier fluid comprising a bis(perfluoroalkyl)ethylene and at least one additional compound present in amounts effective to form an azeotropic composition or an azeotrope-like composition of the carrier fluid, to form a solution; applying the solution to the surface; and removing the carrier fluid from the coating composition to coat the surface with the coating composition.

[0008] The present disclosure further provides a process of cooling a system, comprising two-phase immersion cooling said system with a coolant comprising a bis(perfluoroalkyl)ethylene and at least one additional compound present in amounts effective to form an azeotropic composition or an azeotrope-like composition of the coolant.

[0009] The present disclosure yet further provides a process of cleaning a surface, comprising contacting a composition with said surface, the composition comprising abis(perfluoroalkyl)ethylene and at least one additional compound present in amounts effective to form the composition as azeotropic or an azeotrope-like.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 belongs. Methods and materials are described herein for use in the present invention; other, suitable methods and materials known in the art can also be used. The materials, methods, and examples are illustrative only and not intended to be limiting. All publications, patent applications, patents, sequences, database entries, and other references mentioned herein are incorporated by reference in their entirety. In case of conflict, the present specification, including definitions, will control.

[0010] The various aspects and embodiments of the invention can be used alone or in combinations with each other. Other features and advantages of the present invention will be apparent from the following more detailed description of the preferred embodiment which illustrates, by way of example, the principles of the invention.BRIEF DESCRIPTION OF THE DRAWINGS

[0011] FIG. 1 shows the boiling points of binary mixtures 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.

[0012] FIG. 2 shows the boiling points of binary mixtures of E-HFO-153-10mczz and cis-1-chloro-2,3,3-trifluoropropene (HCFO-1233ydZ) at atmospheric pressure.

[0013] FIG. 3 shows the boiling points of binary mixtures of E-HFO-153-10mczz and 1 , 1 , 1 ,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether (HFE-347pc-f) at atmospheric pressure.

[0014] FIG. 4 shows the boiling points of binary mixtures of E-HFO-153-10mczz and cyclohexane at atmospheric pressure.

[0015] FIG. 5 shows the boiling points of binary mixtures of E-1, 1 ,1, 4, 5,5,5- heptafluoro-4-(trifluoromethyl)-2-pentene (E-HFO-153-10mzzy) and PEIK at atmospheric pressure.

[0016] FIG. 6 shows the boiling points of binary mixtures of E-HFO-153-10mzzy and HCFO-1233ydZ at atmospheric pressure.

[0017] FIG. 7 shows the boiling points of binary mixtures of E-HFO-153-10mzzy and HFE-347pc-f at atmospheric pressure.

[0018] FIG. 8 shows the boiling points of binary mixtures of E-HFO-153-10mzzy and cyclohexane at atmospheric pressure.

[0019] FIG. 9 shows the boiling points of binary mixtures of E-HFO-153-10mzzy and n-heptane at atmospheric pressure.

[0020] FIG. 10 shows the boiling points of binary mixtures of E-HFO-153-10mzzy and n-hexane at atmospheric pressure.

[0021] FIG. 11 shows the boiling points of binary mixtures of E-HFO-153-10mzzy and acetone at atmospheric pressure.

[0022] FIG. 12 shows the boiling points of binary mixtures of E-HFO-153-10mzzy and methyl acetate at atmospheric pressure.

[0023] FIG. 13 shows the boiling points of binary mixtures of E-HFO-153-10mzzy and methyl cyclohexane at atmospheric pressure.

[0024] FIG. 14 shows the boiling points of binary mixtures of E-HFO-153-10mzzy and hexafluoropropyl methyl ether (HFPME) at atmospheric pressure.DETAILED DESCRIPTION

[0025] Disclosed are azeotropic or azeotrope-like compositions including a bis(perfluoroalkyl)ethylene and at least one additional compound. Azeotropic or azeotrope-like compositions including a bis(perfluoroalkyl)ethylene and at least one additional compound for cleaning, carrier fluid, and heat transfer applications and associated processes are also disclosed.

[0026] The present disclosure provides new binary and ternary azeotropic and azeotrope-like compositions comprising hydrofluorocarbon mixtures. These compositions have utility in many of the applications formerly served by chlorofluorocarbon (CFG) compounds. The compositions of the present disclosurepossess some or all of the desired properties of little or no environmental impact and the ability to dissolve oils, greases, and / or fluxes.

[0027] In exemplary embodiments, the bis(perfluoroalkyl)ethylene has the chemical structure shown in Formula (1):RICH=CHR2(1) where Ri and R2are independently linear or branched perfluorocarbons of the formula CnF2n+i, where n is an integer in the range of 1 to 5.

[0028] The stereoisomeric composition of the bis(perfluoroalkyl)ethylene may be the pure Z (cis) isomer, the pure E (trans) isomer, or any mixture of the Z and E isomers.Definitions and Abbreviations

[0029] As used herein, the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having” or any other variation thereof, are intended to cover a non-exclusive inclusion. For example, a process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus. Further, unless expressly stated to the contrary, “or” refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).

[0030] As used herein, the term “consisting essentially of” is used to define a composition or method that includes materials, steps, features, components, or elements, in addition to those literally disclosed provided that these additional included materials, steps, features, components, or elements do not materially affect the basic and novel characteristic(s) of the claimed invention, especially the mode of action to achieve the desired result of any of the processes of the present invention. The term “consists essentially of’ or “consisting essentially of” occupies a middle ground between “comprising” and “consisting of’.

[0031] Also, use of “a” or “an” are employed to describe elements and components described herein. This is done merely for convenience and to give a general sense of the scope of the invention. This description should be read to include one or atleast one and the singular also includes the plural unless it is obvious that it is meant otherwise.

[0032] As used herein, the term “about” is meant to account for variations due to experimental error (e.g., plus or minus approximately 10% of the indicated value). All measurements reported herein are understood to be modified by the term “about”, whether or not the term is explicitly used, unless explicitly stated otherwise.

[0033] As used herein, the term “atmospheric pressure” refers to a pressure of about 101 MPa.

[0034] As used herein, the term “% isomerically pure” refers to the amount of an isomeric compound, by weight, compared to the total amount, by weight, of the isomeric compound and its stereoisomer.

[0035] When an amount, concentration, or other value or parameter is given as either a range, preferred range or a list of upper preferable values and / or lower preferable values, this is to be understood as specifically disclosing all ranges formed from any pair of any upper range limit or preferred value and any lower range limit or preferred value, regardless of whether ranges are separately disclosed. Where a range of numerical values is recited herein, unless otherwise stated, the range is intended to include the endpoints thereof, and all integers and fractions within the range.

[0036] As recognized in the art, an azeotropic composition is an admixture of two or more different components which, when in liquid form and (1a) under a given constant pressure, will boil at a substantially constant temperature, which temperature may be higher or lower than the boiling temperatures of the individual components, or (1 b) at a given constant temperature, will boil at a substantially constant pressure, which pressure may be higher or lower than the boiling pressure of the individual components, and (2) will boil at substantially constant composition, which phase compositions, while constant, are not necessarily equal (see, e.g., M. F. Doherty and M.F. Malone, Conceptual Design of Distillation Systems, McGraw-Hill (New York), 2001 , 185).

[0037] A homogeneous azeotrope, in which a single vapor phase is in equilibrium with a single liquid phase, has, in addition to properties (1a), (1b), and (2) above, thecomposition of each component is the same in each of the coexisting equilibrium phases. The general term “azeotrope” is a commonly used alternative name for a homogeneous azeotrope.

[0038] As used herein, an “azeotrope-like” composition refers to a composition that behaves like an azeotropic composition (i.e., has constant boiling characteristics or a tendency not to fractionate upon boiling or evaporation). Hence, during boiling or evaporation, the vapor and liquid compositions, if they change at all, change only to a minimal or negligible extent. In contrast, the vapor and liquid compositions of non- azeotrope-like compositions change to a substantial degree during boiling or evaporation.

[0039] As used herein, the terms “azeotrope-like” or “azeotrope-like behavior” refer to compositions that exhibit dew point pressure and bubble point pressure with virtually no pressure differential. In some embodiments, the difference in the dew point pressure and bubble point pressure at a given temperature is 3% or less. In some embodiments, the difference in the bubble point and dew point pressures is 5% or less.Azeotrope and Azeotrope-Like Compositions

[0040] The present disclosure provides a composition, comprising: i) a 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 amounts effective to form an azeotropic composition or an azeotrope-like composition.

[0041] In some embodiments, the bis(perfluoroalkyl)ethylene and the at least one additional compound are at least 98 wt%, by weight of the composition. In some embodiments, the bis(perfluoroalkyl)ethylene and the at least one additional compound are at least 99 wt%, by weight of the composition. In some embodiments, the bis(perfluoroalkyl)ethylene and the at least one additional compound are at least 99.5 wt%, by weight of the composition. In some embodiments, the composition consists essentially of the bis(perfluoroalkyl)ethylene and the at least one additionalcompound. In some embodiments, the composition consists of the bis(perfluoroalkyl)ethylene and the at least one additional compound.

[0042] In some embodiments, the bis(perfluoroalkyl)ethylene is at least 99% isomerically pure, by weight, such as, for example, at least 99.5% pure, at least 99.8% pure, or at least 99.9% pure, in either the Z or the E form. In other embodiments, the bis(perfluoroalkyl)ethylene is an isomeric mixture of the Z and E forms, such as, for example, 40 to 60% by weight of the Z form and 40 to 60% by weight of the E form. In some embodiments, the bis(perfluoroalkyl)ethylene is the isomeric mixture as synthesized rather than a Z-rich or an E-rich fraction.

[0043] In some embodiments, the 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-153-1 Omzzy).

[0044] In some embodiments, the composition is a binary azeotrope.

[0045] In some embodiments, the additional compound includes 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, methyl cyclohexane, hexafluoropropyl methyl ether (HFPME), or a combination thereof.

[0046] In some embodiments, the composition includes about 37% to about 76% E-HFO-153-10mczz and about 24% to about 63% perfluoroethyl isopropyl ketone, by weight of the composition, or any values, ranges, or sub-ranges therebetween. 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.

[0047] In some embodiments, the composition includes about 43% to about 66% E-HFO-153-10mczz and about 34% to about 57% perfluoroethyl isopropyl ketone, by weight of the composition. 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.

[0048] In some embodiments, the composition includes 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, or any values, ranges, or sub-rangestherebetween. 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.

[0049] In some embodiments, the composition includes about 60% to about 78% E-HFO-153-10mczz and about 22% to about 40% cis-1-chloro-2,3,3- trifluoropropene, by weight of the composition. 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.

[0050] In some embodiments, the composition includes 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, or any values, ranges, or subranges therebetween. 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.

[0051] In some embodiments, the composition includes 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, by weight of the composition. 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.

[0052] In some embodiments, the composition includes about 84% to about 95% E-HFO-153-10mczz and about 5% to about 16% cyclohexane, by weight of the composition, or any values, ranges, or sub-ranges therebetween. 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.

[0053] In some embodiments, the composition includes about 86% to about 94% E-HFO-153-10mczz and about 6% to about 14% cyclohexane, by weight of the composition. 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.

[0054] In some embodiments, the composition includes about 53% to about 79% E-HFO-153-10mczz and about 21% to about 47% cyclopentane, by weight of the composition, or any values, ranges, or sub-ranges therebetween. 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.

[0055] In some embodiments, the composition includes E-HFO-153-10mczz and has a boiling point of about 35 °C to about 49 °C, or any values, ranges, or subranges therebetween, at a pressure of about 101 kPa.

[0056] In some embodiments, the composition includes about 10% to about 60% E-HFO-153-10mzzy and about 40% to about 90% perfluoroethyl isopropyl ketone, by weight of the composition, or any values, ranges, or sub-ranges therebetween. 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.

[0057] In some embodiments, the composition includes about 18% to about 45% E-HFO-153-10mzzy and about 55% to about 82% perfluoroethyl isopropyl ketone, by weight of the composition. 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.

[0058] In some embodiments, the composition includes 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, or any values, ranges, or sub-ranges therebetween. 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.

[0059] In some embodiments, the composition includes about 60% to about 78% E-HFO-153-10mzzy and about 22% to about 40% cis-1-chloro-2,3,3- trifluoropropene, by weight of the composition. 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.

[0060] In some embodiments, the composition includes 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, or any values, ranges, or subranges therebetween. 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.

[0061] In some embodiments, the composition includes 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, by weight of the composition. In some embodiments, thecomposition has a boiling point in the range of about 47.9 °C to about 48.1 °C at a pressure of about 101 kPa.

[0062] In some embodiments, the composition includes 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, or any values, ranges, or sub-ranges therebetween. 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.

[0063] In some embodiments, the composition includes about 83.8% to about 93.5% E-HFO-153-10mzzy and about 6.5% to about 16.2% cyclohexane, by weight of the composition. 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.

[0064] In some embodiments, the composition includes about 52% to about 84% E-HFO-153-10mzzy and about 16% to about 48% cyclopentane, by weight of the composition, or any values, ranges, or sub-ranges therebetween. 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.

[0065] In some embodiments, the composition includes about 96.6% to about 98.6% E-HFO-153-10mzzy and about 1.4% to about 3.4% n-heptane, by weight of the composition, or any values, ranges, or sub-ranges therebetween. 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.

[0066] In some embodiments, the composition includes about 71% to about 93% E-HFO-153-10mzzy and about 7% to about 29% n-hexane, by weight of the composition, or any values, ranges, or sub-ranges therebetween. 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.

[0067] In some embodiments, the composition includes about 77% to about 92% E-HFO-153-10mzzy and about 8% to about 23% n-hexane, by weight of the composition. 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.

[0068] In some embodiments, the composition includes about 75% to about 91% E-HFO-153-10mzzy and about 9% to about 25% acetone, by weight of the composition, or any values, ranges, or sub-ranges therebetween. 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.

[0069] In some embodiments, the composition includes about 79% to about 89.5% E-HFO-153-10mzzy and about 10.5% to about 21% acetone, by weight of the composition. 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.

[0070] In some embodiments, the composition includes about 66% to about 88.7% E-HFO-153-10mzzy and about 11.3% to about 34% methyl acetate, by weight of the composition, or any values, ranges, or sub-ranges therebetween. 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.

[0071] In some embodiments, the composition includes about 69% to about 84.4% E-HFO-153-10mzzy and about 15.6% to about 31% methyl acetate, by weight of the composition. 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.

[0072] In some embodiments, the composition includes about 97.2% to about 98.5% E-HFO-153-10mzzy and about 1.5% to about 2.8% methyl cyclohexane, by weight of the composition, or any values, ranges, or sub-ranges therebetween. 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.

[0073] In some embodiments, the composition includes about 70% to about 91% E-HFO-153-10mzzy and about 9 % HFPME to about 30 % HFPME, by weight of the composition, or any values, ranges, or sub-ranges therebetween. In some embodiments, the composition has a boiling point in the range of about 48.3 °C to about 48.7 °C a pressure of about 101 kPa.

[0074] In some embodiments, the composition is a ternary azeotrope.

[0075] In some embodiments, the composition includes 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 of the composition, or any values, ranges, or sub-ranges therebetween. 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.

[0076] In some embodiments, the composition includes 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 of the composition, or any values, ranges, or sub-ranges therebetween. 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.

[0077] In some embodiments, the composition includes 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, or any values, ranges, or sub-ranges therebetween. 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.Methods of Use

[0078] In some embodiments, compositions described herein are useful as carrier fluids. In some embodiments, the carrier fluids aid in the deposition of fluorolubricants, such as, for example, fluorolubricants for hard-disk drives. Accordingly, the present disclosure further provides processes of depositing a fluorolubricant, comprising contacting a composition described herein with said fluorolubricant and transporting said fluorolubricant with said composition to a target location.

[0079] In some embodiments, a process of coating a surface include dissolving a coating composition in a carrier fluid of a composition described herein to form a solution. The process further includes applying the solution to the surface and removing the carrier fluid from the coating composition to coat the surface with the coating composition. In some embodiments, the coating composition includes a perfluoropolyether. In some embodiments, the surface is a surface of a disk of a hard disk drive.

[0080] In some embodiments, compositions described herein are useful as coolants. In some embodiments, compositions described herein are coolants in two- phase immersion cooling systems. In some embodiments, the two-phase immersion cooling systems are for data centers or electric vehicle batteries. Accordingly, the present disclosure further provides processes for cooling a system, comprising two- phase immersion cooling the system with a composition described herein.

[0081] In some embodiments, compositions described herein are useful as degreasers and / or cleaners for precision cleaning and / or industrial cleaning. In some embodiments, compositions described herein are useful for vapor degreasing, aerosol cleaning, and / or cold cleaning. Accordingly, the present disclosure further provides processes of cleaning a surface, comprising contacting a composition described herein with said surface.

[0082] The means for contacting a device, surface, or substrate is not critical and may be accomplished, for example, by immersion of 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) that has been wet with the composition. Alternatively, a composition provided herein may also be used in a vapor degreasing or defluxing apparatus designed for such residue removal. Such vapor degreasing or defluxing equipment is available from various suppliers such as Forward Technology (a subsidiary of the Crest Group, Trenton, NJ), Trek Industries (Azusa, CA), and Ultronix, Inc. (Hatfield, PA) among others.

[0083] In some embodiments, the surface or substrate may be an integrated circuit device, in which case, the residue comprises 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 (pBGAs), or Chip scale packaging components. The surface or substrate may additionally be a metal surface such as stainless steel. The rosin flux may be any type commonly used in the soldering of integrated circuit devices, including but not limited to RMA (rosin mildly activated), RA (rosin activated), WS (water soluble), and OA (organic acid). Oil residues include but are not limited to mineral oils, motor oils, and silicone oils.

[0084] In some embodiments, compositions described herein are useful in the electronics industry, the aviation industry, and / or the defense industry.

[0085] In some embodiments, azeotropic or azeotrope- 1 ike compositions comprising a bis(perfluoroalkyl)ethylene and at least one additional compound are useful in any or all of the above-mentioned methods of use. In some embodiments, the bis(perfluoroalkyl)ethylene and least one additional compound are at least 98%, by weight of such compositions. In some embodiments, the bis(perfluoroalkyl)ethylene and least one additional compound are at least 99%, by weight of such compositions. In some embodiments, such compositions consist essentially of the bis(perfluoroalkyl)ethylene and least one additional compound. In some embodiments, such compositions consist of the bis(perfluoroalkyl)ethylene and least one additional compound.EXAMPLES

[0086] The invention will be described in greater detail by way of specific examples. The following examples are offered for illustrative purposes, and are not intended to limit the invention in any manner. Those of skill in the art will readily recognize a variety of non-critical parameters which can be changed or modified to yield essentially the same results.

[0087] In the following examples, the E-HFO-153-10mczz was trans- 1 ,1 ,1,2,2,5,5,6,6,6-decafluoro-3-hexene (HFO-153-10mczz(E)) with less than 0.1 mol% cis-1 ,1,1,2,2,5,5,6,6,6-decafluoro-3-hexene (HFO-153-10mczz(Z)), and the E- H FO-153- 10mzzy was trans-1 ,1 ,1,4, 5,5,5-heptafluoro-4-(trifluoromethyl)-2-pentene (HFO-153-10mzzy(E)) with less than 0.1 mol% cis-1,1,1 ,4,5,5, 5-heptafluoro-4- (trifluoromethyl)-2-pentene (HFO-153-10mzzy(Z)).Example 1

[0088] Solvents were screened for azeotropic behavior with E-HFO-153-10mczz or E-HFO-153-10mzzy by atmospheric ebulliometer methods. 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-trifluoroethylether (HFE-347pc-f; AsahiKlin™ AE-3000; AGC Chemicals), cyclohexane, cyclopentane, n-heptane, n-hexane, acetone, methyl acetate, methyl cyclohexane, 2,3-dihydrodecafluropentane (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 trimethyl pentane.

[0089] A known amount of HFO was charged to an ebulliometer and heated to the atmospheric boiling point, and the boiling point was recorded. Known amounts of the second component were added and the boiling point of the blended composition was recorded after each addition. Mixtures that demonstrated boiling points below the boiling point of both components are azeotropic. The results are shown in Table 1.TABLE 1 Binary Azeotropic Behavior Screening

[0090] Both E-HFO-153-10mczz and E-HFO-153-10mzzy showed 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 methyl cyclohexane. The other tested solvents did not show azeotropic behavior with E-HFO-153-10mzzy.Example 2

[0091] An ebulliometer method was used to screen for azeotropic binary mixtures of E-HFO-153-10mczz and PEIK. A known amount of E-HFO-153-10mczz was decanted into the ebulliometer 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 was then recorded. This was repeated over a range of binary compositions.

[0092] FIG. 1 shows a plot of the boiling point as a function of composition. The binary mixture of E-HFO-153-10mczz and PEIK was azeotropic or azeotrope-like at least over the range of about 24 wt% PEIK to about 63 wt% PEIK with a boiling point in the range of about 48.5 °C to about 48.8 °C, alternatively over the range of about 34 wt% PEIK to about 57 wt% PEIK with a boiling point in the range of about 48.5 °C to about 48.7 °C, or any value, range, or sub-range therebetween at a pressure of about 101 kPa.Example 3

[0093] An ebulliometer method was used to screen for azeotropic binary mixtures of E-HFO-153-10mczz and HCFO-1233ydZ. A known amount of E-HFO-153-10mczz was decanted into the ebulliometer and heated to the atmospheric boiling point, which was recorded. A known amount of HCFO-1233ydZ was added, and the boiling point was allowed to equilibrate and was then recorded. This was repeated over a range of binary compositions.

[0094] FIG. 2 shows a plot of the boiling point as a function of composition. The binary mixture of E-HFO-153-10mczz and HCFO-1233ydZ was azeotropic or azeotrope-like at least over 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 over 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 sub-range therebetween at a pressure of about 101 kPa.Example 4

[0095] An ebulliometer method was used to screen for azeotropic binary mixtures of E-HFO-153-10mczz and HFE-347pc-f. A known amount of E-HFO-153-10mczz was decanted into the ebulliometer 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 was then recorded. This was repeated over a range of binary compositions.

[0096] FIG. 3 shows a plot of the boiling point as a function of composition. The binary mixture of E-HFO-153-10mczz and HFE-347pc-f was azeotropic or azeotrope-like at least over 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 over 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 sub-range therebetween at a pressure of about 101 kPa.Example 5

[0097] An ebulliometer method was used to screen for azeotropic binary mixtures of E-HFO-153-10mczz and cyclohexane. A known amount of E-HFO-153-10mczz was decanted into the ebulliometer 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 was then recorded. This was repeated over a range of binary compositions.

[0098] FIG. 4 shows a plot of the boiling point as a function of composition. The binary mixture of E-HFO-153-10mczz and cyclohexane was azeotropic or azeotropelike at least over the range of about 5 wt% cyclohexane to about 16 wt% cyclohexane with a boiling point in the range of about 46.4 °C to about 46.9 °C, alternatively over the range of about 6 wt% cyclohexane to about 14 wt% cyclohexane with a boiling point in the range of about 46.4 °C to about 46.7 °C, or any value, range, or sub-range therebetween at a pressure of about 101 kPa.Example 6

[0099] An ebulliometer method was used to screen for azeotropic binary mixtures of E-HFO-153-10mzzy and PEIK. A known amount of E-HFO-153-10mzzy was decanted into the ebulliometer 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 was then recorded. This was repeated over a range of binary compositions.

[0100] FIG. 5 shows a plot of the boiling point as a function of composition. The binary mixture of E-HFO-153-10mzzy and PEIK was azeotropic or azeotrope-like at least over the range of about 40 wt% PEIK to about 90 wt% PEIK with a boiling point in the range of about 48.0 °C to about 48.4 °C, alternatively over the range of about 55 wt% PEIK to about 82 wt% PEIK with a boiling point in the range of about 48.0 °C to about 48.2 °C, or any value, range, or sub-range therebetween at a pressure of about 101 kPa.Example 7

[0101] An ebulliometer method was used to screen for azeotropic binary mixtures of E-HFO-153-10mzzy and HCFO-1233ydZ. A known amount of E-HFO-153-10mzzy was decanted into the ebulliometer and heated to the atmospheric boiling point, which was recorded. A known amount of HCFO-1233ydZ was added, and the boiling point was allowed to equilibrate and was then recorded. This was repeated over a range of binary compositions.

[0102] FIG. 6 shows a plot of the boiling point as a function of composition. The binary mixture of E-HFO-153-10mzzy and HCFO-1233ydZ was azeotropic or azeotrope-like at least over 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 over 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 sub-range therebetween at a pressure of about 101 kPa.Example 8

[0103] An ebulliometer method was used to screen for azeotropic binary mixtures of E-HFO-153-10mzzy and HFE-347pc-f. A known amount of E-HFO-153-10mzzy was decanted into the ebulliometer 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 was then recorded. This was repeated over a range of binary compositions.

[0104] FIG. 7 shows a plot of the boiling point as a function of composition. The binary mixture of E-HFO-153-10mzzy and HFE-347pc-f was azeotropic or azeotrope-like at least over 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 over 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 sub-range therebetween at a pressure of about 101 kPa.Example 9

[0105] An ebulliometer method was used to screen for azeotropic binary mixtures of E-HFO-153-10mzzy and cyclohexane. A known amount of E-HFO-153-10mzzy was decanted into the ebulliometer 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 was then recorded. This was repeated over a range of binary compositions.

[0106] FIG. 8 shows a plot of the boiling point as a function of composition. The binary mixture of E-HFO-153-10mzzy and cyclohexane was azeotropic or azeotropelike at least over the range of about 5.5 wt% cyclohexane to about 18.8 wt% cyclohexane with a boiling point in the range of about 46.6 °C to about 47.0 °C, alternatively over the range of about 6.5 wt% cyclohexane to about 16.2 wt% cyclohexane with a boiling point in the range of about 46.6 °C to about 46.8 °C, or any value, range, or sub-range therebetween at a pressure of about 101 kPa.Example 10

[0107] An ebulliometer method was used to screen for azeotropic binary mixtures of E-HFO-153-10mzzy and n-heptane. A known amount of E-HFO-153-10mzzy was decanted into the ebulliometer and heated to the atmospheric boiling point, which was recorded. A known amount of n-heptane was added, and the boiling point was allowed to equilibrate and was then recorded. This was repeated over a range of binary compositions.

[0108] FIG. 9 shows a plot of the boiling point as a function of composition. The binary mixture of E-HFO-153-10mzzy and n-heptane was azeotropic or azeotropelike at least over the range of about 1 .4 wt% n-heptane to about 3.4 wt% n-heptane with a boiling point in the range of about 48.5 °C to about 48.7 °C at a pressure of about 101 kPa.Example 11

[0109] An ebulliometer method was used to screen for azeotropic binary mixtures of E-HFO-153-10mzzy and n-hexane. A known amount of E-HFO-153-10mzzy was decanted into the ebulliometer and heated to the atmospheric boiling point, which was recorded. A known amount of n-hexane was added, and the boiling point was allowed to equilibrate and was then recorded. This was repeated over a range of binary compositions.

[0010] FIG. 10 shows a plot of the boiling point as a function of composition. The binary mixture of E-HFO-153-10mzzy and n-hexane was azeotropic or azeotropelike at least over the range of about 7 wt% n-hexane to about 29 wt% n-hexane with a boiling point in the range of about 44.3 °C to about 44.9 °C, alternatively over the range of about 8 wt% n-hexane to about 23 wt% n-hexane with a boiling point in the range of about 44.3 °C to about 44.6 °C, or any value, range, or sub-range therebetween at a pressure of about 101 kPa.Example 12

[0011] An ebulliometer method was used to screen for azeotropic binary mixtures of E-HFO-153-10mzzy and acetone. A known amount of E-HFO-153-10mzzy was decanted into the ebulliometer and heated to the atmospheric boiling point, whichwas recorded. A known amount of acetone was added, and the boiling point was allowed to equilibrate and was then recorded. This was repeated over a range of binary compositions.

[0112] FIG. 11 shows a plot of the boiling point as a function of composition. The binary mixture of E-HFO-153-10mzzy and acetone was azeotropic or azeotrope- 1 ike at least over the range of about 9 wt% acetone to about 25 wt% acetone with a boiling point in the range of about 46.4 °C to about 46.9 °C, alternatively over the range of about 10.5 wt% acetone to about 21 wt% acetone with a boiling point in the range of about 46.4 °C to about 46.7 °C, or any value, range, or sub-range therebetween at a pressure of about 101 kPa.Example 13

[0113] An ebulliometer method was used to screen for azeotropic binary mixtures of E-HFO-153-10mzzy and methyl acetate. A known amount of E-HFO-153-10mzzy was decanted into the ebulliometer and heated to the atmospheric boiling point, which was recorded. A known amount of methyl acetate was added, and the boiling point was allowed to equilibrate and was then recorded. This was repeated over a range of binary compositions.

[0114] FIG. 12 shows a plot of the boiling point as a function of composition. The binary mixture of E-HFO-153-10mzzy and methyl acetate was azeotropic or azeotrope-like at least over the range of about 11.3 wt% methyl acetate to about 34 wt% methyl acetate with a boiling point in the range of about 47.3 °C to about 47.8 °C, alternatively over the range of about 15.6 wt% methyl acetate to about 31 wt% methyl acetate with a boiling point in the range of about 47.3 °C to about 47.6 °C, or any value, range, or sub-range therebetween at a pressure of about 101 kPa.Example 14

[0115] An ebulliometer method was used to screen for azeotropic binary mixtures of E-HFO-153-10mzzy and methyl cyclohexane. A known amount of E-HFO-153- 10mzzy was decanted into the ebulliometer and heated to the atmospheric boiling point, which was recorded. A known amount of methyl cyclohexane was added, and the boiling point was allowed to equilibrate and was then recorded. This was repeated over a range of binary compositions.

[0116] FIG. 13 shows a plot of the boiling point as a function of composition. The binary mixture of E-HFO-153-10mzzy and methyl cyclohexane was azeotropic or azeotrope-like at least over the range of about 1.5 wt% methyl cyclohexane to about 2.8 wt% methyl cyclohexane with a boiling point in the range of about 49.3 °C to about 49.5 °C at a pressure of about 101 kPa.Example 15

[0117] An ebulliometer method was used to screen for azeotropic binary mixtures of E-HFO-153-10mzzy and hexafluoropropyl methyl ether (HFPME). A known amount of E-HFO-153-10mzzy was decanted into the ebulliometer and heated to the atmospheric boiling point, which was recorded. A known amount of HFPME was added, and the boiling point was allowed to equilibrate and was then recorded. This was repeated over a range of binary compositions.

[0118] FIG. 14 shows a plot of the boiling point as a function of composition. The binary mixture of E-HFO-153-10mzzy and HFPME was azeotropic or azeotrope-like at least over the range of about 9 wt% HFPME to about 30 wt% HFPME with a boiling point in the range of about 48.3 °C to about 48.7 °C, alternatively over the range of about 16 wt% HFPME to about 26 wt% HFPME with a boiling point in the range of about 48.3 °C to about 48.5 °C, or any value, range, or sub-range therebetween at a pressure of about 101 kPa.Example 16

[0119] A ternary azeotrope including E-HFO-153-10mzzy, HFE-347pc-f, and cyclohexane was determined via atmospheric distillation experiments starting from the initial ternary composition listed in Table 2 using a 20-plate Vigreux distillation column at a pressure of about 101 kPa. The distillation was allowed to reflux through the column for one hour, and the first 10% fraction was collected and analyzed for composition via gas chromatography / flame ionization detection (GC / FID).TABLE 2 Ternary Compositions of E-HFO-153-10mzzy, HFE-347pc-f, and Cyclohexane

[0120] The ternary composition demonstrated azeotropic behavior, as the blend could not be effectively separated by fractional distillation. Additionally, the boiling point and dew point of the mixture were lower than any of the components or the binaries.

[0121] A ternary mixture of the azeotropic composition (72 wt% E-HFO-153- 10mzzy,18.5 wt% HFE-347pc-f and 9.5 wt% cyclohexane) was prepared and measured for dielectric constant following ASTM D924 and volume resistivity following ASTM D1169. The dielectric constant was 2.38 F / m and the volume resistivity was 8.37X1011Q-cm, which are dielectric properties comparable to commercially available fluorochemicals while enabling a lower operating temperature with the reduced boiling point.

[0122] A ternary mixture of the azeotropic composition (72 wt% E-HFO-153- 10mzzy,18.5 wt% HFE-347pc-f and 9.5 wt% cyclohexane) was prepared and tested for flash point following ASTM D56 Tag closed cup. The mixture did not exhibit a flash point in the range of -15 °C and 46 °C.Example 17

[0123] A ternary azeotrope including E-HFO-153-1 Omzzy, HCFO-1233ydZ, and n- hexane was determined via atmospheric distillation experiments starting from the initial ternary composition listed in Table 2 using a 20-plate Vigreux distillationcolumn at a pressure of about 101 kPa. The distillation was allowed to reflux through the column for one hour, and the first 10% fraction was collected and analyzed for composition via GC / FID.TABLE 3 Ternary Compositions of E-HFO-153-10mzzy, HCFO-1233ydZ, and n- hexane

[0124] The ternary composition demonstrated azeotropic behavior, as the blend could not be effectively separated by fractional distillation. Additionally, the boiling point and dew point of the mixture were lower than any of the components or the binaries.Example 18

[0125] A ternary azeotrope including E-HFO-153-10mzzy, HCFO-1233ydZ, and cyclohexane was determined via atmospheric distillation experiments starting from the initial ternary composition listed in Table 2 using a 20-plate Vigreux distillation column at a pressure of about 101 kPa. The distillation was allowed to reflux through the column for one hour, and the first 10% fraction was collected and analyzed for composition via GC / FID.TABLE 4 Ternary Compositions of E-HFO-153-10mzzy, HCFO-1233ydZ, and Cyclohexane

[0126] The ternary composition demonstrated azeotropic behavior, as the blend could not be effectively separated by fractional distillation. Additionally, the boiling point and dew point of the mixture were lower than any of the components or the binaries.OTHER EMBODIMENTS

[0127] Embodiment 1 : a composition, comprising: i) a 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 amounts effective to form an azeotropic composition or an azeotrope- 1 ike composition.

[0128] Embodiment 2: the composition of embodiment 1 , wherein the bis(perfluoroalkyl)ethylene and the at least one additional compound are at least 98 wt%, by weight of the composition.

[0129] Embodiment 3: the composition of embodiment 1, wherein the bis(perfluoroalkyl)ethylene and the at least one additional compound are at least 99 wt%, by weight of the composition.

[0130] Embodiment 4: the composition of embodiment 1 , wherein the composition consists essentially of the bis(perfluoroalkyl)ethylene and the at least one additional compound.

[0131] Embodiment 5: the composition of embodiment 1 , wherein the bis(perfluoroalkyl)ethylene is of Formula (1):CHRI=CHR2(1)

[0132] wherein Ri and R2are independently linear or branched perfluorocarbons of the formula CnF2n+i, where n is an integer in the range of 1 to 5.

[0133] Embodiment 6: the composition of embodiment 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).

[0134] Embodiment 7: the composition of embodiment 6, wherein the bis(perfluoroalkyl)ethylene comprises E-HFO-153-10mczz.

[0135] Embodiment 8: the composition of embodiment 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.

[0136] Embodiment 9: the composition of embodiment 7, 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.

[0137] Embodiment 10: the composition of embodiment 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.

[0138] Embodiment 11 : the composition of 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.

[0139] Embodiment 12: the composition of embodiment 7, wherein the at least one additional compound comprises cyclohexane and the composition comprises about84% to about 95% E-HFO-153-10mczz and about 5% to about 16% cyclohexane, by weight of the composition.

[0140] Embodiment 13: the composition of embodiment 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.

[0141] Embodiment 14: the composition of embodiment 7, wherein the composition has a boiling point of about 35 °C to about 49 °C at a pressure of about 101 kPa.

[0142] Embodiment 15: the composition of embodiment 6, wherein the bis(perfluoroalkyl)ethylene comprises E-HFO-153-10mzzy.

[0143] Embodiment 16: the composition of embodiment 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, methyl cyclohexane, HFPME, and combinations thereof.

[0144] Embodiment 17: the composition of embodiment 15, 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.

[0145] Embodiment 18: the composition of 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.

[0146] Embodiment 19: the composition of 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.

[0147] Embodiment 20: the composition of 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.

[0148] Embodiment 21 : the composition of embodiment 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.

[0149] Embodiment 22: the composition of embodiment 15, wherein the at least one additional compound comprises n-heptane and the composition comprises about 96.6% to about 98.6% E-HFO-153-10mzzy and about 1.4% to about 3.4% n- heptane, by weight of the composition.

[0150] Embodiment 23: the composition of embodiment 15, 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.

[0151] Embodiment 24: the composition of embodiment 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.

[0152] Embodiment 25: the composition of 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.

[0153] Embodiment 26: the composition of embodiment 15, wherein the at least one additional compound comprises methyl cyclohexane and the composition comprises about 97.2% to about 98.5% E-HFO-153-10mzzy and about 1.5% to about 2.8% methyl cyclohexane, by weight of the composition.

[0154] Embodiment 27: the composition of embodiment 15, wherein the at least one additional compound comprises methyl cyclohexane and cyclohexane and the composition comprises about 70% to about 74% E-HFO-153-10mzzy, about 18% toabout 19% 1 , 1 , 1 ,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether, and about 8% to about 11% cyclohexane, by weight of the composition.

[0155] Embodiment 28: the composition of 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 of the composition.

[0156] Embodiment 29: the composition of 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.

[0157] Embodiment 30: the composition of embodiment 15, wherein the composition has a boiling point of about 35 °C to about 49 °C at a pressure of about 101 kPa.

[0158] Embodiment 31 : a process of coating a surface, comprising: dissolving a coating composition in a carrier fluid, the carrier fluid comprising a bis(perfluoroalkyl)ethylene and at least one additional compound present in amounts effective to form an azeotropic composition or an azeotrope- 1 ike composition of the carrier fluid, to form a solution; applying the solution to the surface; and removing the carrier fluid from the coating composition to coat the surface with the coating composition.

[0159] Embodiment 32: the process of embodiment 31 , wherein the bis(perfluoroalkyl)ethylene is of Formula (1):CHRI=CHR2(1)

[0160] wherein Ri and R2are independently linear or branched perfluorocarbons of the formula CnF2n+i, where n is an integer in the range of 1 to 5.

[0161] Embodiment 33: the process of embodiment 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).

[0162] Embodiment 34: the process of embodiment 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, methyl cyclohexane, hexafluoropropyl methyl ether, and combinations thereof.

[0163] Embodiment 35: the process of embodiment 31 , wherein the coating composition comprises a perfluoropolyether.

[0164] Embodiment 36: a process of cooling a system, comprising two-phase immersion cooling said system with a coolant comprising a bis(perfluoroalkyl)ethylene and at least one additional compound present in amounts effective to form an azeotropic composition or an azeotrope- 1 ike composition of the coolant.

[0165] Embodiment 37: the process of embodiment 36, wherein the bis(perfluoroalkyl)ethylene is of Formula (1):CHRI=CHR2(1)

[0166] wherein Ri and R2are independently linear or branched perfluorocarbons of the formula CnF2n+i, where n is an integer in the range of 1 to 5.

[0167] Embodiment 38: the process of embodiment 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).

[0168] Embodiment 39: the process of embodiment 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, methyl cyclohexane, hexafluoropropyl methyl ether, and combinations thereof.

[0169] Embodiment 40: a process of cleaning a surface, comprising contacting a composition with said surface, the composition comprising a bis(perfluoroalkyl)ethylene and at least one additional compound present in amounts effective to form the composition as azeotropic or an azeotrope-like.

[0170] Embodiment 41 : the process of embodiment 40, wherein the bis(perfluoroalkyl)ethylene is of Formula (1):CHRI=CHR2(1)

[0171] wherein Ri and R2are independently linear or branched perfluorocarbons of the formula CnF2n+i, where n is an integer in the range of 1 to 5.

[0172] Embodiment 42: the process of embodiment 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).

[0173] Embodiment 43: the process of embodiment 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, methyl cyclohexane, hexafluoropropyl methyl ether, and combinations thereof.

[0174] All above-mentioned references are hereby incorporated by reference herein.

[0175] It is to be understood that while the invention has been described in conjunction with the detailed description thereof, the foregoing description is intended to illustrate and not 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. It should be appreciated by those persons having ordinary skill in the art(s) to which the present invention relates that any of the features described herein in respect of any particular aspect and / or embodiment of the present invention can be combined with one or more of any of the other features of any other aspects and / or embodiments of the present invention described herein, with modifications as appropriate to ensure compatibility of the combinations. Such combinations are considered to be part of the present invention contemplated by this disclosure.

Claims

CLAIMSWhat is claimed is:

1. A composition, comprising: i) a 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 amounts effective to form an azeotropic composition or an azeotrope- 1 ike composition.

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

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

5. The composition of 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 of 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 of 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, methyl cyclohexane, 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% E-HFO-153-10mzzy and about 1.4% to about 3.4% 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 methyl cyclohexane and the composition comprises about 97.2% toabout 98.5% E-HFO-153-10mzzy and about 1.5% to about 2.8% methyl cyclohexane, by weight of the composition.

23. 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.

24. The composition of claim 13, wherein the at least one additional compound comprises methyl cyclohexane 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 of the composition.

25. 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 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 of the composition.

26. 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 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.

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

28. A process of coating a surface, comprising: dissolving a coating composition in a carrier fluid, the carrier fluid comprising a bis(perfluoroalkyl)ethylene and at least one additional compound present in amounts effective to form an azeotropic composition or an azeotrope- 1 ike composition of the carrier fluid, to form a solution; applying the solution to the surface; and removing the carrier fluid from the coating composition to coat the surface with the coating composition.

29. The process 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).

30. The process 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, methyl cyclohexane, hexafluoropropyl methyl ether, and combinations thereof.

31. The process of claim 29, wherein the coating composition comprises a perfluoropolyether.

32. A process of cooling a system, comprising two-phase immersion cooling said system with a coolant comprising a bis(perfluoroalkyl)ethylene and at least one additional compound present in amounts effective to form an azeotropic composition or an azeotrope- 1 ike composition of the coolant.

33. The process 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).

34. The process 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, methyl cyclohexane, hexafluoropropyl methyl ether, and combinations thereof.

35. A process of cleaning a surface, comprising contacting a composition with said surface, the composition comprising a bis(perfluoroalkyl)ethylene and at least one additional compound present in amounts effective to form the composition as azeotropic or an azeotrope- 1 ike.

36. The process 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).

37. The process 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, methyl cyclohexane, hexafluoropropyl methyl ether, and combinations thereof.

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