Azeotrope and azeotrope-like compositions comprising neopentane and isomers of hfo-1336mzz

Abstract

To provide a composition useful in various applications including heat transfer applications and refrigeration applications.SOLUTION: The present invention provides a composition comprising: (i) neopentane; and (ii) Z-1,1,1,4,4,4-hexafluoro-2-butene, wherein the Z-1,1,1,4,4,4-hexafluoro-2-butene is present in the composition in an amount effective to form an azeotrope or azeotrope-like composition with the neopentane.SELECTED DRAWING: None

Description

Technical Field

[0001] The present application relates to an azeotropic composition and an azeotrope-like composition comprising neopentane and a compound selected from E-1,1,1,4,4,4-hexafluoro-2-butene (HFO-1336mzz(E)) and Z-1,1,1,4,4,4-hexafluoro-2-butene (HFO-1336mzz(Z)). The compositions described herein may be useful in a variety of applications including, but not limited to, heat transfer applications and refrigeration applications.

Background Art

[0002] Over the past few decades, efforts have been made in many industries to find alternatives to ozone-depleting chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs). CFCs and HCFCs have been used in a wide range of applications including, for example, their use as aerosol propellants, refrigerants, and heat transfer media. In the search for alternatives to these widely used compounds, the use of hydrofluoroolefins (HFOs) has received attention in many industries.

Summary of the Invention

Means for Solving the Problems

[0003] The present application particularly relates to i) neopentane (i.e., 2,2-dimethylpropane), and ii) a compound selected from E-1,1,1,4,4,4-hexafluoro-2-butene (i.e., HFO-1336mzz(E)) and Z-1,1,1,4,4,4-hexafluoro-2-butene (i.e., HFO-1336mzz(Z)), Provided is a composition in which E-1,1,1,4,4,4-hexafluoro-2-butene or Z-1,1,1,4,4,4-hexafluoro-2-butene is present in the composition in an amount effective to form an azeotropic or azeotrope-like composition with neopentane.

[0004] This application further provides a method of using the compositions provided herein as propellants and heat transfer agents (e.g., in refrigeration or heat transfer applications).

[0005] Unless defined otherwise, 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 for use in the present invention are described herein, and other suitable methods and materials known in the art may 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 herein by reference in their entirety. In case of conflict, the present specification, including definitions, will control.

Brief Description of the Drawings

[0006]

Figure 1

Figure 2

Modes for Carrying Out the Invention

[0007] This application relates to i) neopentane (i.e., 2,2-dimethylpropane), and ii) a compound selected from E-1,1,1,4,4,4-hexafluoro-2-butene (i.e., HFO-1336mzz(E)) and Z-1,1,1,4,4,4-hexafluoro-2-butene (i.e., HFO-1336mzz(Z)), the composition comprising E-1,1,1,4,4,4-hexafluoro-2-butene or Z-1,1,1,4,4,4-hexafluoro-2-butene being present in the composition in an amount effective to form an azeotropic composition or an azeotrope-like composition with neopentane.

[0008] Definitions and Abbreviations As used herein, the terms "comprises," "comprising," "includes," "including," "has," "having," or any other variation thereof are intended to cover non-exclusive inclusion. For example, a process, method, article, or apparatus that comprises 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, or apparatus. Further, unless expressly stated to the contrary, "or" refers to an inclusive "or" and not to an exclusive "or." For example, condition A or B is satisfied by any one of the following: i.e., A is true (or present) and B is false (or absent), A is false (or absent) and B is true (or present), and both A and B are true (or present).

[0009] As used herein, "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 additionally included materials, steps, features, components, or elements do not substantially affect the basic and novel characteristics (s) of the claimed invention, particularly the mechanism of action for achieving any desired result of the process of the present invention. The term "consisting essentially of" or "consisting essentially of" takes an intermediate position between "comprising" and "consisting of".

[0010] For example, in some embodiments, the compositions provided herein are i) neopentane and ii) a compound selected from E-1,1,1,4,4,4-hexafluoro-2-butene (HFO-1336mzz(E)) and Z-1,1,1,4,4,4-hexafluoro-2-butene (HFO-1336mzz(Z)), wherein E-1,1,1,4,4,4-hexafluoro-2-butene or Z-1,1,1,4,4,4-hexafluoro-2-butene is present in the composition in an amount effective to form an azeotropic or azeotrope-like composition with neopentane, and iii) one or more additional components described herein (the one or more additional components do not substantially affect the basic and novel properties (s) of the composition), consisting essentially of.

[0011] Also, the use of "a" or "an" is employed to describe the elements and components described herein. This is done merely for convenience and to give a general sense of the scope of the present invention. This description should be construed to include one or at least one, and the singular form also includes the plural form unless it is clear that it has a different meaning.

[0012] As used herein, the term "about" means to account for variations due to experimental error (e.g., about plus or minus 10% of the indicated value). All measurements reported herein are understood to be modified by the term "about" whether or not the term "about" is explicitly used, unless otherwise specified.

[0013] As used herein, the term "azeotropic composition" refers to a composition in which, at a given temperature in equilibrium, the boiling point pressure (of the liquid phase) is the same as the dew point pressure (of the vapor phase) (i.e., X2 = Y2). One way to characterize an azeotropic composition is that the vapor produced by partial evaporation or distillation of the liquid may have the same composition as the liquid from which the vapor is evaporated or distilled (i.e., the mixture distills / refluxes without change in composition). A constant boiling composition is characterized as azeotropic in that it exhibits a maximum or minimum boiling point compared to a non-azeotropic mixture of the same components. An azeotropic composition can also be characterized by a minimum or maximum value of the vapor pressure of the mixture relative to the vapor pressure of each undiluted component at a given temperature.

[0014] As used herein, the terms "azeotrope-like composition" and "near-azeotropic composition" refer to a composition in which the difference between the bubble point ("BP") pressure and the dew point ("DP") pressure of the composition at a specific temperature is 5% or less relative to the bubble point pressure (i.e., [(BP - VP) / BP]×100 ≦ 5). As used herein, the terms "3% azeotrope-like composition" and "3% near-azeotropic composition" are understood to mean a composition in which the difference between the bubble point pressure ("BP") and the dew point pressure ("DP") of the composition at a specific temperature is 3% or less relative to the bubble point pressure (i.e., [(BP - DP) / BP]×100 ≦ 3).

[0015] A binary azeotropic composition or an azeotrope-like composition of a substantially constant-boiling mixture can be characterized in many ways according to selected conditions. For example, it is well known to those skilled in the art that at different pressures, the composition of a given azeotropic composition or azeotrope-like composition varies at least to some extent, similar to the boiling point temperature. Thereby, an azeotropic composition or an azeotrope-like composition of two compounds represents a unique type of relationship, but has a composition that varies according to temperature and / or pressure. Therefore, in order to define azeotropic compositions and azeotrope-like compositions, ranges of composition rather than fixed compositions are often used.

[0016] For the purposes of the present invention, an "effective amount" refers to the amount of each component of the compositions provided herein that, when combined, forms an azeotropic composition or an azeotrope-like composition. This definition includes the amounts of each component, and these amounts can vary according to the pressure applied to the composition as long as the azeotropic composition or azeotrope-like composition continues to exist at different pressures (although the boiling points may be different). Therefore, the effective amount includes the amounts of each component of the compositions of the present invention that form an azeotropic composition or an azeotrope-like composition at temperatures or pressures other than those described herein (which can be expressed, for example, as weight %).

[0017] As used herein, the term "mole fraction" refers to the ratio of the number of moles of one component in a composition to the total number of moles of the two components in a binary composition (e.g., X2 = m2 / (m1 + m2)).

[0018] To determine the relative volatility of any two compounds, a method known as the PTx method can be used. In this procedure, the total absolute pressure within a cell of known volume is measured at a constant temperature for various compositions of the two compounds. The use of the PTx method is described in detail in "Phase Equilibrium in Process Design", Wiley-Interscience Publisher, 1970, by Harold R. Null, pages 124 - 126, which is incorporated herein by reference. The resulting pressure versus liquid composition data is also referred to as vapor-liquid equilibrium data (i.e., VLE data).

[0019] These measured values can be converted into the compositions of the vapor and liquid in the equilibrium state in the PTx cell by using an activity coefficient model such as the non-random two-liquid (NRTL) equation, for example, to represent a liquid-phase non-ideal system. For example, the use of activity coefficient equations such as the NRTL equation is described in detail in "The Properties of Gases and Liquids", 4th Edition, published by McGraw Hill, written by Reid, Prausnitz, and Poling, pages 241-387, and "Phase Equilibria in Chemical Engineering", published by Butterworth Publishers in 1985, written by Stanley M. Walas, pages 165-244. Regarding the collection of VLE data, the determination of interaction parameters by regression methods, and the use of equations of state to predict the non-ideal behavior of the system, it is taught in "Double Azeotropy in Binary Mixtures of NH3 and CHF2CF2" C.-P. Chai Kao, M.E. Paulaitis, A. Yokozeki, Fluid Phase Equilibria, Volume 127 (1997) pages 191-203. All of the above references are incorporated herein by reference. Although not wishing to be bound by any theory or explanation, the NRTL equation, in combination with the PTx cell data, can sufficiently predict the relative volatility of the compositions provided herein, and thus it is considered that the behavior of these mixtures in a multi-stage separation device such as a distillation column can be predicted.

[0020] When a quantity, concentration, or other value or parameter is given as any of a range, a preferred range, or a list of preferred upper and / or lower values, these are to be understood as specifically disclosing all ranges formed from any pair of any range upper limit or preferred upper value and any range lower limit or preferred lower value, whether or not the ranges are separately disclosed. When a numerical range is recited herein, unless otherwise indicated, the range is intended to include its endpoints and all integers and fractions within the range.

[0021] Composition A composition comprising: i) neopentane; and ii) a compound selected from E-1,1,1,4,4,4-hexafluoro-2-butene and Z-1,1,1,4,4,4-hexafluoro-2-butene.

[0022] In some embodiments, the compositions provided herein are azeotropic mixtures or azeotrope-like compositions. In some embodiments, the compositions provided herein are azeotropic compositions. In some embodiments, the compositions provided herein are azeotrope-like compositions. In some embodiments, E-1,1,1,4,4,4-hexafluoro-2-butene or Z-1,1,1,4,4,4-hexafluoro-2-butene is present in the composition in an amount effective to form an azeotropic composition or an azeotrope-like composition with neopentane.

[0023] In some embodiments, the compositions provided herein include neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene, and the E-1,1,1,4,4,4-hexafluoro-2-butene is present in the composition in an amount effective to form an azeotropic or azeotrope-like composition with neopentane. In some embodiments, the composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene is an azeotropic mixture composition (i.e., an azeotropic composition). In some embodiments, the composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene is an azeotrope-like composition.

[0024] In some embodiments, the composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 40 to about 60 mol% neopentane, such as from about 40 to about 55, from about 40 to about 50, from about 40 to about 45, from about 45 to about 60, from about 45 to about 55, from about 45 to about 50, from about 50 to about 60, from about 50 to about 55, or from about 55 to about 60 mol% neopentane. In some embodiments, the composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 40 to about 50 mol% neopentane.

[0025] In some embodiments, the composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 60 to about 40 mol% E-1,1,1,4,4,4-hexafluoro-2-butene, such as from about 60 to about 45, from about 60 to about 50, from about 60 to about 55, from about 55 to about 40, from about 55 to about 45, from about 55 to about 50, from about 50 to about 40, from about 50 to about 45, or from about 45 to about 40 mol% E-1,1,1,4,4,4-hexafluoro-2-butene. In some embodiments, the composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene comprises from 60 to about 50 mol% E-1,1,1,4,4,4-hexafluoro-2-butene.

[0026] In some embodiments, the composition comprises from about 40 to about 60 mol% of neopentane and from about 60 to about 40 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene. In some embodiments, the composition comprises from about 40 to about 60 mol% of neopentane and from about 60 to about 40 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene and has a boiling point of from about -40°C to about 120°C at a pressure of from about 2 psi to about 390 psi.

[0027] In some embodiments, the composition comprises from about 40 to about 50 mol% of neopentane and from about 60 to about 50 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene. In some embodiments, the composition comprises from about 40 to about 50 mol% of neopentane and from about 60 to about 50 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene and has a boiling point of from about 0.9°C to about 128°C at a pressure of from about 1 atm to about 30 atm.

[0028] In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene comprises from 98.0 to about 99.9 mol% of neopentane, such as from about 98.0 to about 99.8, from about 98.0 to about 99.5, from about 98.0 to about 99.3, from about 98.0 to about 99.0, from about 98.0 to about 98.8, from about 98.0 to about 98.5, from about 98.5 to about 99.9, from about 98.5 to about 99.8, from about 98.5 to about 99.5, from about 98.5 to about 99.3, from about 98.5 to about 99.0, from about 98.5 to about 98.8, from about 98.8 to about 99.9, from about 98.8 to about 99.8, from about 98.8 to about 99.5, from about 98.8 to about 99.3, from about 98.8 to about 99.0, from about 99.0 to about 99.9, from about 99.0 to about 99.8, from about 99.0 to about 99.5, from about 99.0 to about 99.3, from about 99.3 to about 99.9, from about 99.3 to about 99.8, from about 99.3 to about 99.5, from about 99.5 to about 99.9, from about 99.5 to about 99.8, or from about 99.8 to about 99.9 mol% of neopentane. In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 98.2 to about 99.8 mol% of neopentane.

[0029] In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 2.0 to about 0.1 mole percent of E-1,1,1,4,4,4-hexafluoro-2-butene, for example, from about 2.0 to about 0.2, from about 2.0 to about 0.5, from about 2.0 to about 0.7, from about 2.0 to about 1.0, from about 2.0 to about 1.2, from about 2.0 to about 1.5, from about 1.5 to about 0.1, from about 1.5 to about 0.2, from about 1.5 to about 0.5, from about 1.5 to about 0.7, from about 1.5 to about 1.0, from about 1.5 to about 1.2, from about 1.2 to about 0.1, from about 1.2 to about 0.2, from about 1.2 to about 0.5, from about 1.2 to about 0.7, from about 1.2 to about 1.0, from about 1.0 to about 0.1, from about 1.0 to about 0.2, from about 1.0 to about 0.5, from about 1.0 to about 0.7, from about 0.7 to about 0.1, from about 0.7 to about 0.2, from about 0.7 to about 0.5, from about 0.5 to about 0.1, from about 0.5 to about 0.2, or from about 0.2 to about 0.1 mole percent of E-1,1,1,4,4,4-hexafluoro-2-butene.

[0030] In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 1.6 to about 0.2 mole percent of E-1,1,1,4,4,4-hexafluoro-2-butene.

[0031] In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 98.4 to about 99.8 mole percent of neopentane and from about 1.6 to about 0.2 mole percent of E-1,1,1,4,4,4-hexafluoro-2-butene. In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 98.4 to about 99.8 mole percent of neopentane and from about 1.6 to about 0.2 mole percent of E-1,1,1,4,4,4-hexafluoro-2-butene and has a boiling point of from about 8.3 °C to about 9.3 °C at a pressure of about 1 atmosphere.

[0032] In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 35 to about 65 mol% neopentane, such as from about 35 to about 60, from about 35 to about 55, from about 35 to about 50, from about 35 to about 45, from about 35 to about 40, from about 40 to about 65, from about 40 to about 60, from about 40 to about 55, from about 40 to about 50, from about 40 to about 45, from about 45 to about 65, from about 45 to about 60, from about 45 to about 55, from about 45 to about 50, from about 50 to about 65, from about 50 to about 60, from about 50 to about 55, from about 55 to about 65, from about 55 to about 60, or from about 60 to about 65 mol% neopentane. In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 38.4 to about 62.6 mol% neopentane.

[0033] In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 70 to about 35 mol% E-1,1,1,4,4,4-hexafluoro-2-butene, such as from about 70 to about 40, from about 70 to about 45, from about 70 to about 50, from about 70 to about 55, from about 70 to about 60, from about 70 to about 65, from about 65 to about 35, from about 65 to about 40, from about 65 to about 45, from about 65 to about 50, from about 65 to about 55, from about 65 to about 60, from about 60 to about 35, from about 60 to about 40, from about 60 to about 45, from about 60 to about 50, from about 60 to about 55, from about 55 to about 35, from about 55 to about 40, from about 55 to about 45, from about 55 to about 50, from about 50 to about 35, from about 50 to about 40, from about 50 to about 45, from about 45 to about 35, from about 45 to about 40, or from about 40 to about 35 mol% E-1,1,1,4,4,4-hexafluoro-2-butene. In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 65.2 to about 37.4 mol% E-1,1,1,4,4,4-hexafluoro-2-butene.

[0034] In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 38.4 to about 62.6 mole percent neopentane and from about 65.2 to about 37.4 mole percent E-1,1,1,4,4,4-hexafluoro-2-butene. In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 38.4 to about 62.6 mole percent neopentane and from about 65.2 to about 37.4 mole percent E-1,1,1,4,4,4-hexafluoro-2-butene and has a boiling point of from about 0.9 °C to about 1.2 °C at a pressure of about 1 atmosphere.

[0035] In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 0.1 to about 3.0 mole percent neopentane, such as from about 0.1 to about 2.8, from about 0.1 to about 2.5, from about 0.1 to about 2.0, from about 0.1 to about 1.5, from about 0.1 to about 1.0, from about 0.1 to about 0.5, from about 0.5 to about 3.0, from about 0.5 to about 2.8, from about 0.5 to about 2.5, from about 0.5 to about 2.0, from about 0.5 to about 1.5, from about 0.5 to about 1.0, from about 1.0 to about 3.0, from about 1.0 to about 2.8, from about 1.0 to about 2.5, from about 1.0 to about 2.0, from about 1.0 to about 1.5, from about 1.5 to about 3.0, from about 1.5 to about 2.8, from about 1.5 to about 2.5, from about 1.5 to about 2.0, from about 2.0 to about 3.0, from about 2.0 to about 2.8, from about 2.0 to about 2.5, from about 2.5 to about 3.0, from about 2.5 to about 2.8, or from about 2.8 to about 3.0 mole percent neopentane. In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 0.2 to about 2.8 mole percent neopentane.

[0036] In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 99.9 to about 97.0 mole % of E-1,1,1,4,4,4-hexafluoro-2-butene, for example, from about 99.9 to about 97.2, from about 99.9 to about 97.5, from about 99.9 to about 98.0, from about 99.9 to about 98.5, from about 99.9 to about 99.0, from about 99.9 to about 99.8, from about 99.8 to about 97.0, from about 99.8 to about 97.2, from about 99.8 to about 97.5, from about 99.8 to about 98.0, from about 99.8 to about 98.5, from about 99.8 to about 99.0, from about 99.0 to about 97.0, from about 99.0 to about 97.2, from about 99.0 to about 97.5, from about 99.0 to about 98.0, from about 99.0 to about 98.5, from about 98.5 to about 97.0, from about 98.5 to about 97.2, from about 98.5 to about 97.5, from about 98.5 to about 98.0, from about 98.0 to about 97.0, from about 98.0 to about 97.2, from about 98.0 to about 97.5, from about 97.5 to about 97.0, from about 97.5 to about 97.2, or from about 97.2 to about 97.0 mole % of E-1,1,1,4,4,4-hexafluoro-2-butene. In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 99.8 to about 97.2 mole % of E-1,1,1,4,4,4-hexafluoro-2-butene.

[0037] In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 0.2 to about 2.8 mole % of neopentane and from about 99.8 to about 97.2 mole % of E-1,1,1,4,4,4-hexafluoro-2-butene. In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 0.2 to about 2.8 mole % of neopentane and from about 99.8 to about 97.2 mole % of E-1,1,1,4,4,4-hexafluoro-2-butene and has a boiling point of from about 6.3 °C to about 7.4 °C at a pressure of about 1 atmosphere.

[0038] In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene About 99.8 to about 98.2 mol% of neopentane and about 0.2 to about 1.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or About 71.6 to about 47.6 mol% of neopentane and about 28.4 to about 52.4 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or About 1.2 to about 0.2 mol% of neopentane and about 98.8 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or About 99.8 to about 98.4 mol% of neopentane and about 0.2 to about 1.6 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or About 66.6 to about 40.8 mol% of neopentane and about 33.4 to about 59.2 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or About 1.8 to about 0.2 mol% of neopentane and about 98.2 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or About 62.8 to about 35.2 mol% of neopentane and about 37.2 to about 64.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or About 2.6 to about 0.2 mol% of neopentane and about 97.4 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or About 59.8 to about 30.2 mol% of neopentane and about 40.2 to about 69.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or About 3.4 to about 0.2 mol% of neopentane and about 96.6 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or About 58.4 to about 28.2 mol% of neopentane and about 41.6 to about 71.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or About 3.8 to about 0.2 mol% of neopentane and about 96.2 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 57.2 to about 26.4 mol% of neopentane and from about 42.8 to about 73.6 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 4.4 to about 0.2 mol% of neopentane and from about 95.6 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 55.4 to about 23.6 mol% of neopentane and from about 44.6 to about 76.4 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 5.2 to about 99.1 mol% of neopentane and from about 94.8 to about 0.9 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 99.8 to about 98.6 mol% of neopentane and from about 0.2 to about 1.4 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 53.8 to about 23.2 mol% of neopentane and from about 46.2 to about 76.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 5.4 to about 0.2 mol% of neopentane and from about 94.6 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 56 to about 24.4 mol% of neopentane and from about 44.0 to about 75.6 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 4.6 to about 0.2 mol% of neopentane and from about 95.4 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 57.2 to about 3.8 mol% of neopentane and from about 42.8 to about 96.2 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 2.6 to about 0.2 mol% of neopentane and from about 97.4 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene.

[0039] In some embodiments, the composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene About 99.8 to about 98.2 mol% of neopentane and about 0.2 to about 1.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or About 71.6 to about 47.6 mol% of neopentane and about 28.4 to about 52.4 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or About 1.2 to about 0.2 mol% of neopentane and about 98.8 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or About 99.8 to about 98.4 mol% of neopentane and about 0.2 to about 1.6 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or About 66.6 to about 40.8 mol% of neopentane and about 33.4 to about 59.2 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or About 1.8 to about 0.2 mol% of neopentane and about 98.2 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or About 62.8 to about 35.2 mol% of neopentane and about 37.2 to about 64.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or About 2.6 to about 0.2 mol% of neopentane and about 97.4 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or About 59.8 to about 30.2 mol% of neopentane and about 40.2 to about 69.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or About 3.4 to about 0.2 mol% of neopentane and about 96.6 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or About 58.4 to about 28.2 mol% of neopentane and about 41.6 to about 71.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or About 3.8 to about 0.2 mol% of neopentane and about 96.2 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 57.2 to about 26.4 mol% of neopentane and from about 42.8 to about 73.6 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 4.4 to about 0.2 mol% of neopentane and from about 95.6 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 55.4 to about 23.6 mol% of neopentane and from about 44.6 to about 76.4 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 5.2 to about 99.1 mol% of neopentane and from about 94.8 to about 0.9 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 99.8 to about 98.6 mol% of neopentane and from about 0.2 to about 1.4 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 53.8 to about 23.2 mol% of neopentane and from about 46.2 to about 76.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 5.4 to about 0.2 mol% of neopentane and from about 94.6 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 56 to about 24.4 mol% of neopentane and from about 44.0 to about 75.6 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 4.6 to about 0.2 mol% of neopentane and from about 95.4 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 57.2 to about 3.8 mol% of neopentane and from about 42.8 to about 96.2 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 2.6 to about 0.2 mol% of neopentane and from about 97.4 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, and When the composition has a boiling point of about -40°C to about 120°C at a pressure of about 1 atmosphere, for example, about -40°C to about 100°C, about -40°C to about 80°C, about -40°C to about 60°C, about -40°C to about 40°C, about -40°C to about 20°C, about -40°C to about 0°C, about -40°C to about -20°C, about -20°C to about 120°C, about -20°C to about 100°C, about -20°C to about 80°C, about -20°C to about 60°C, about -20°C to about 40°C, about -20°C to about 20°C, about -20°C to about 0°C, about 0°C to about 120°C, about 0°C to about 100°C, about 0°C to about 80°C, about 0°C to about 60°C, about 0°C to about 40°C, about 0°C to about 20°C, about 20°C to about 120°C, about 20°C to about 100°C, about 20°C to about 80°C, about 20°C to about 60°C, about 20°C to about 40°C, about 40°C to about 120°C, about 40°C to about 100°C, about 40°C to about 80°C, about 40°C to about 60°C, about 60°C to about 120°C, about 60°C to about 100°C, about 60°C to about 80°C, about 80°C to about 120°C, about 80°C to about 100°C, or about 100°C to about 120°C.

[0040] In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene has a boiling point of about -40°C at a pressure of about 1 atmosphere.

[0041] In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene has a boiling point of about -20°C at a pressure of about 1 atmosphere.

[0042] In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene has a boiling point of about 0°C at a pressure of about 1 atmosphere.

[0043] In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene has a boiling point of about 20°C at a pressure of about 1 atmosphere.

[0044] In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene has a boiling point of about 30°C at a pressure of about 1 atmosphere.

[0045] In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene has a boiling point of about 40 °C at a pressure of about 1 atmosphere.

[0046] In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene has a boiling point of about 60 °C at a pressure of about 1 atmosphere.

[0047] In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene has a boiling point of about 80 °C at a pressure of about 1 atmosphere.

[0048] In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene has a boiling point of about 100 °C at a pressure of about 1 atmosphere.

[0049] In some embodiments, a composition comprising neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene has a boiling point of about 120 °C at a pressure of about 1 atmosphere.

[0050] In some embodiments, the compositions provided herein comprise neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene, and the Z-1,1,1,4,4,4-hexafluoro-2-butene is present in the composition in an amount effective to form an azeotropic composition or an azeotrope-like composition with neopentane. In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene is an azeotropic mixture composition (i.e., an azeotropic composition). In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene is an azeotrope-like composition.

[0051] In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 60 to about 95 mol% neopentane, such as from about 60 to about 90, from about 60 to about 85, from about 60 to about 80, from about 60 to about 75, from about 60 to about 70, from about 65 to about 95, from about 65 to about 90, from about 65 to about 85, from about 65 to about 80, from about 65 to about 75, from about 70 to about 95, from about 70 to about 90, from about 70 to about 85, from about 70 to about 80, from about 75 to about 95, from about 75 to about 90, from about 75 to about 85, from about 80 to about 95, from about 80 to about 90, or from about 85 to about 95 mol% neopentane. In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 60 to about 93 mol% neopentane.

[0052] In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 40 to about 5 mol% Z-1,1,1,4,4,4-hexafluoro-2-butene, such as from about 40 to about 10, from about 40 to about 15, from about 40 to about 20, from about 40 to about 25, from about 40 to about 30, from about 40 to about 35, from about 35 to about 5, from about 35 to about 10, from about 35 to about 15, from about 35 to about 20, from about 35 to about 25, from about 35 to about 30, from about 30 to about 5, from about 30 to about 10, from about 30 to about 15, from about 30 to about 20, from about 30 to about 25, from about 25 to about 5, from about 25 to about 10, from about 25 to about 15, from about 25 to about 20, from about 20 to about 5, from about 20 to about 10, from about 20 to about 15, from about 15 to about 5, from about 15 to about 10, or from about 10 to about 5 mol% Z-1,1,1,4,4,4-hexafluoro-2-butene. In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 40 to about 7 mol% Z-1,1,1,4,4,4-hexafluoro-2-butene.

[0053] In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 60 to about 93 mole % neopentane and from about 40 to about 7 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene. In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 60 to about 93 mole % neopentane and from about 40 to about 7 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene and has a boiling point of from about -40 °C to about 120 °C at a pressure of from about 1.5 psi to about 310 psi.

[0054] In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 50 to about 85 mole % neopentane, such as from about 50 to about 80, from about 50 to about 75, from about 50 to about 70, from about 50 to about 65, from about 50 to about 60, from about 50 to about 55, from about 55 to about 85, from about 55 to about 80, from about 55 to about 75, from about 55 to about 70, from about 55 to about 65, from about 55 to about 60, from about 60 to about 85, from about 60 to about 80, from about 60 to about 75, from about 60 to about 70, from about 60 to about 65, from about 65 to about 85, from about 65 to about 80, from about 65 to about 75, from about 65 to about 70, from about 70 to about 85, from about 70 to about 80, from about 70 to about 75, from about 75 to about 85, from about 75 to about 80, or from about 80 to about 85 mole % neopentane. In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 56 to about 83 mole % neopentane.

[0055] In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 50 to about 15 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, for example, from about 50 to about 20, from about 50 to about 25, from about 50 to about 30, from about 50 to about 35, from about 50 to about 40, from about 50 to about 45, from about 45 to about 15, from about 45 to about 20, from about 45 to about 25, from about 45 to about 30, from about 45 to about 35, from about 45 to about 40, from about 40 to about 15, from about 40 to about 20, from about 40 to about 25, from about 40 to about 30, from about 40 to about 35, from about 35 to about 15, from about 35 to about 20, from about 35 to about 25, from about 35 to about 30, from about 30 to about 15, from about 30 to about 20, from about 30 to about 25, from about 25 to about 15, from about 25 to about 20, or from about 20 to about 15 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene. In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 44 to about 17 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene.

[0056] In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 56 to about 83 mol% of neopentane and from about 44 to about 17 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene. In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 56 to about 83 mol% of neopentane and from about 44 to about 17 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene and has a boiling point of from about 5°C to about 145°C at a pressure of from about 1 atm to about 30 atm.

[0057] In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 99.9 to about 75.0 mole % neopentane, for example, from about 99.9 to about 80.0, from about 99.9 to about 85.0, from about 99.9 to about 90.0, from about 99.9 to about 95.0, from about 99.9 to about 99.0, from about 99.9 to about 99.6, from about 99.6 to about 80.0, from about 99.6 to about 85.0, from about 99.6 to about 90.0, from about 99.6 to about 95.0, from about 99.6 to about 99.0, from about 99.0 to about 80.0, from about 99.0 to about 85.0, from about 99.0 to about 90.0, from about 99.0 to about 95, from about 95.0 to about 80.0, from about 95.0 to about 85.0, from about 95.0 to about 90.0, from about 90.0 to about 80.0, from about 90.0 to about 85.0, or from about 85.0 to about 80.0 mole % neopentane. In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 99.6 to about 79.2 mole % neopentane.

[0058] In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 0.1 to about 25.0 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene, for example, from about 0.1 to about 20.0, from about 0.1 to about 15.0, from about 0.1 to about 10.0, from about 0.1 to about 5.0, from about 0.1 to about 1.0, from about 0.1 to about 0.4, from about 0.4 to about 25.0, from about 0.4 to about 20.0, from about 0.4 to about 15.0, from about 0.4 to about 10.0, from about 0.4 to about 5.0, from about 0.4 to about 1.0, from about 1.0 to about 25.0, from about 1.0 to about 20.0, from about 1.0 to about 15.0, from about 1.0 to about 10.0, from about 1.0 to about 5.0, from about 5.0 to about 25.0, from about 5.0 to about 20.0, from about 5.0 to about 15.0, from about 5.0 to about 10.0, from about 10.0 to about 25.0, from about 10.0 to about 20.0, from about 10.0 to about 15.0, from about 15.0 to about 25.0, from about 15.0 to about 20.0, or from about 20.0 to about 25.0 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene. In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 0.4 to about 20.8 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene.

[0059] In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 99.6 to about 79.2 mole % neopentane and from about 0.4 to about 20.8 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene. In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 99.6 to about 79.2 mole % neopentane and from about 0.4 to about 20.8 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene and has a boiling point of from about 7.8 °C to about 9.4 °C at a pressure of about 1 atmosphere.

[0060] In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 4.0 to about 1.0 mole % neopentane, such as from about 4.0 to about 1.5, from about 4.0 to about 2.0, from about 4.0 to about 2.5, from about 4.0 to about 3.0, from about 4.0 to about 3.5, from about 3.5 to about 1.0, from about 3.5 to about 1.5, from about 3.5 to about 2.0, from about 3.5 to about 2.5, from about 3.5 to about 3.0, from about 3.0 to about 1.0, from about 3.0 to about 1.5, from about 3.0 to about 2.0, from about 3.0 to about 2.5, from about 2.5 to about 1.0, from about 2.5 to about 1.5, from about 2.5 to about 2.0, from about 2.0 to about 1.0, from about 2.0 to about 1.5, or from about 1.5 to about 1.0 mole % neopentane. In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 3.2 to about 1.6 mole % neopentane.

[0061] In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 96.0 to about 99.0 mole percent of Z-1,1,1,4,4,4-hexafluoro-2-butene, such as from about 96.0 to about 98.5, from about 96.0 to about 98.0, from about 96.0 to about 97.5, from about 96.0 to about 97.0, from about 96.0 to about 96.5, from about 96.5 to about 99.0, from about 96.5 to about 98.5, from about 96.5 to about 98.0, from about 96.5 to about 97.5, from about 96.5 to about 97.0, from about 97.0 to about 99.0, from about 97.0 to about 98.5, from about 97.0 to about 98.0, from about 97.0 to about 97.5, from about 97.5 to about 99.0, from about 97.5 to about 98.5, from about 97.5 to about 98.0, from about 98.0 to about 99.0, from about 98.0 to about 98.5, or from about 98.5 to about 99.0 mole percent of Z-1,1,1,4,4,4-hexafluoro-2-butene. In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 96.8 to about 98.4 mole percent of Z-1,1,1,4,4,4-hexafluoro-2-butene.

[0062] In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 3.2 to about 1.6 mole percent of neopentane and from about 96.8 to about 98.4 mole percent of Z-1,1,1,4,4,4-hexafluoro-2-butene. In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene comprises from about 3.2 to about 1.6 mole percent of neopentane and from about 96.8 to about 98.4 mole percent of Z-1,1,1,4,4,4-hexafluoro-2-butene and has a boiling point of from about 32.6 °C to about 33.0 °C at a pressure of about 1 atmosphere.

[0063] In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene from about 99.8 to about 85.2 mole percent of neopentane and from about 0.2 to about 14.8 mole percent of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 99.8 to about 80.8 mol% of neopentane and about 0.2 to about 19.2 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 99.8 to about 76.2 mol% of neopentane and about 0.2 to about 23.8 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 99.8 to about 61.8 mol% of neopentane and about 0.2 to about 38.2 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 0.4 to about 0.2 mol% of neopentane and about 99.6 to about 99.8 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 99.8 to about 69.8 mol% of neopentane and about 0.2 to about 30.2 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 99.8 to about 67.6 mol% of neopentane and about 0.2 to about 32.4 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 99.8 to about 95.0 mol% of neopentane and about 0.2 to about 5 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 86.4 to about 63.6 mol% of neopentane and about 13.6 to about 36.4 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 0.4 to about 0.2 mol% of neopentane and about 99.6 to about 99.8 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 99.8 to about 96.6 mol% of neopentane and about 0.2 to about 3.4 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 80.6 to about 59.6 mol% of neopentane and about 19.4 to about 40.4 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 99.8 to about 97.6 mol% of neopentane and about 0.2 to about 2.4 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or From about 74.2 to about 56.0 mol% of neopentane and from about 25.8 to about 44.0 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or From about 0.2 to about 0.8 mol% of neopentane and from about 99.2 to about 99.8 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or From about 99.8 to about 98.2 mol% of neopentane and from about 0.2 to about 1.8 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or From about 76.6 to about 50.0 mol% of neopentane and from about 23.4 to about 50.0 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or From about 1.0 to about 0.2 mol% of neopentane and from about 99.0 to about 99.8 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene.

[0064] In some embodiments, the composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene From about 99.8 to about 85.2 mol% of neopentane and from about 0.2 to about 14.8 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or From about 99.8 to about 80.8 mol% of neopentane and from about 0.2 to about 19.2 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or From about 99.8 to about 76.2 mol% of neopentane and from about 0.2 to about 23.8 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or From about 99.8 to about 61.8 mol% of neopentane and from about 0.2 to about 38.2 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or From about 0.4 to about 0.2 mol% of neopentane and from about 99.6 to about 99.8 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or From about 99.8 to about 69.8 mol% of neopentane and from about 0.2 to about 30.2 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 99.8 to about 67.6 mol% of neopentane and about 0.2 to about 32.4 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 99.8 to about 95.0 mol% of neopentane and about 0.2 to about 5 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 86.4 to about 63.6 mol% of neopentane and about 13.6 to about 36.4 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 0.4 to about 0.2 mol% of neopentane and about 99.6 to about 99.8 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 99.8 to about 96.6 mol% of neopentane and about 0.2 to about 3.4 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 80.6 to about 59.6 mol% of neopentane and about 19.4 to about 40.4 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 99.8 to about 97.6 mol% of neopentane and about 0.2 to about 2.4 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 74.2 to about 56.0 mol% of neopentane and about 25.8 to about 44.0 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 0.2 to about 0.8 mol% of neopentane and about 99.2 to about 99.8 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 99.8 to about 98.2 mol% of neopentane and about 0.2 to about 1.8 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 76.6 to about 50.0 mol% of neopentane and about 23.4 to about 50.0 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 1.0 to about 0.2 mol% of neopentane and about 99.0 to about 99.8 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, and The composition has a boiling point of about -40°C to about 120°C at a pressure of about 1 atmosphere. For example, the composition has a boiling point of about -40°C to about 120°C at a pressure of about 1 atmosphere, such as about -40°C to about 100°C, about -40°C to about 80°C, about -40°C to about 60°C, about -40°C to about 40°C, about -40°C to about 20°C, about -40°C to about 0°C, about -40°C to about -20°C, about -20°C to about 120°C, about -20°C to about 100°C, about -20°C to about 80°C, about -20°C to about 60°C, about -20°C to about 40°C, about -20°C to about 20°C, about -20°C to about 0°C, about 0°C to about 120°C, about 0°C to about 100°C, about 0°C to about 80°C, about 0°C to about 60°C, about 0°C to about 40°C, about 0°C to about 20°C, about 20°C to about 120°C, about 20°C to about 100°C, about 20°C to about 80°C, about 20°C to about 60°C, about 20°C to about 40°C, about 40°C to about 120°C, about 40°C to about 100°C, about 40°C to about 80°C, about 40°C to about 60°C, about 60°C to about 120°C, about 60°C to about 100°C, about 60°C to about 80°C, about 80°C to about 120°C, about 80°C to about 100°C, or about 100°C to about 120°C.

[0065] In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene has a boiling point of about -40°C at a pressure of about 1 atmosphere.

[0066] In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene has a boiling point of about -20°C at a pressure of about 1 atmosphere.

[0067] In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene has a boiling point of about 0°C at a pressure of about 1 atmosphere.

[0068] In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene has a boiling point of about 20°C at a pressure of about 1 atmosphere.

[0069] In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene has a boiling point of about 30 °C at a pressure of about 1 atmosphere.

[0070] In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene has a boiling point of about 40 °C at a pressure of about 1 atmosphere.

[0071] In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene has a boiling point of about 60 °C at a pressure of about 1 atmosphere.

[0072] In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene has a boiling point of about 80 °C at a pressure of about 1 atmosphere.

[0073] In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene has a boiling point of about 100 °C at a pressure of about 1 atmosphere.

[0074] In some embodiments, a composition comprising neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene has a boiling point of about 120 °C at a pressure of about 1 atmosphere.

[0075] In some embodiments, the compositions provided herein further comprise one or more additional components (i.e., additives). In some embodiments, each of the one or more additional components is independently selected from the group consisting of a lubricant, a pour point depressant, an antifoaming agent, a thickening agent, an emulsifying agent, a dispersing agent, an antioxidant, an extreme pressure agent, a corrosion inhibitor, a detergent, a catalyst, a surfactant, a flame retardant, a preservative, a colorant, an antioxidant, a reinforcing agent, a filler, an antistatic agent, a solubilizing agent, an IR attenuator, a nucleating agent, a bubble regulator, an extrusion aid, a stabilizer, a heat insulating agent, a plasticizer, a viscosity modifier, an impact resistance improver, a gas barrier resin, a polymer modifier, a rheology modifier, an antibacterial agent, a vapor pressure modifier, a UV absorber, a crosslinking agent, a permeability modifier, a bittering agent, a propellant, an acid scavenger, or any mixture thereof.

[0076] Usage method The composition of the present invention can be used in a wide range of applications including, but not limited to, use as an aerosol propellant, a refrigerant, and a heat transfer medium.

[0077] Use as a heat transfer medium The compositions provided herein can act as a working fluid used to carry heat from a heat source to a heat sink. Such heat transfer compositions can also be useful as a refrigerant in a cycle in which the fluid undergoes a phase transition, i.e., a cycle in which the fluid changes from a liquid to a gas and back to a liquid, or vice versa.

[0078] Exemplary heat transfer systems include, but are not limited to, air conditioners, refrigerators, freezers, heat pumps, chillers, flooded evaporative coolers, direct expansion coolers, walk-in coolers, heat pumps, mobile refrigerators, mobile air conditioning units, and combinations thereof.

[0079] In some embodiments, the compositions provided herein can be useful in mobile heat transfer systems such as refrigeration, air conditioning, or heat pump systems or devices. In some embodiments, the compositions provided herein can be useful in stationary heat transfer systems such as refrigeration, air conditioning, or heat pump systems or devices.

[0080] As used herein, the term "mobile heat transfer system" refers to any refrigeration, air conditioning, or heating device incorporated into a road, rail, sea, or air transportation unit. Further, mobile cooling or air conditioning units are independent of any mobile carrier and include devices known as "intermodal" systems. Such intermodal systems include "containers" (combined sea / land transportation) and "swap bodies" (combined road / rail transportation).

[0081] As used herein, the term "stationary heat transfer system" refers to a system that is fixed in place during operation. A stationary heat transfer system may be located or mounted within a building, or may be an independent unit installed outdoors, such as a soft drink vending machine. These stationary applications may be stationary air conditioning units or heat pumps, including but not limited to chillers, transcritical heat pumps (e.g., those operating at condenser temperatures above 50°C, 70°C, 80°C, 100°C, 120°C, 140°C, 160°C, 180°C, or 200°C), residential, commercial, or industrial air conditioning systems, which may be window-mounted, ductless, ducted, packaged terminal, chillers, and those external to but connected to a building (e.g., rooftop systems). In stationary refrigeration applications, the compositions provided herein may be useful in high-, medium-, and / or low-temperature refrigeration equipment, including commercial, industrial, or residential refrigerators and freezers, ice machines, built-in coolers and freezers, flooded evaporative coolers, direct expansion coolers, walk-in and reach-in coolers and freezers, and combination systems. In some embodiments, the compositions provided herein may be used in supermarket refrigeration systems.

[0082] In some embodiments, the compositions provided herein may be useful in methods for generating cooling, methods for generating heating, and methods for transferring heat.

[0083] In some embodiments, the present application provides a method for generating cooling, comprising evaporating the composition provided herein in the vicinity of an object to be cooled and then condensing the composition.

[0084] In some embodiments, the present application further provides a method for generating heating, comprising condensing the composition provided herein in the vicinity of an object to be heated and then evaporating the composition.

[0085] In some embodiments, the present application provides a method of using the compositions provided herein as heat transfer fluid compositions. In some embodiments, the method includes transporting the composition from a heat source to a heat sink.

[0086] Any of the compositions provided herein may be useful, inter alia, as alternatives to currently used ("in-use") refrigerants, including but not limited to R-123 (or HFC-123, 2,2-dichloro-1,1,1-trifluoroethane), R-11 (or CFC-11, trichlorofluoromethane), R-12 (or CFC-12, dichlorodifluoromethane), R-22 (chlorodifluoromethane), R-245fa (or HFC-245fa, 1,1,1,3,3-pentafluoropropane), R-114 (or CFC-114, 1,2-dichloro-1,1,2,2-tetrafluoroethane), R-236fa (or HFC-236fa, 1,1,1,3,3,3-hexafluoropropane), R-236ea (or HFC-236ea, 1,1,1,2,3,3-hexafluoropropane), and R-124 (or HCFC-124, 2-chloro-1,1,1,2-tetrafluoroethane).

[0087] As used herein, the term "in-use refrigerant" refers to a refrigerant for which a heat transfer system is designed to operate or a refrigerant present within a heat transfer system.

[0088] In some embodiments, the present application provides a method of operating a heat transfer system designed to operate with an in-use refrigerant or a method for transferring heat by filling an empty system with the compositions provided herein or by substantially replacing the in-use refrigerant with the compositions provided herein.

[0089] As used herein, the term "substantially replace" means discharging the existing refrigerant from the system or pumping the existing refrigerant out of the system and then filling the system with the composition of the present invention (i.e., the composition provided herein). The system can be flushed with one or more amounts of alternative refrigerant prior to filling. It is understood that some small amount of the existing refrigerant may remain in the system even after the system is filled with the composition provided herein.

[0090] In some embodiments, the present application provides a method for refilling a heat transfer system containing an existing refrigerant and a lubricant, the method comprising substantially removing the existing refrigerant from the heat transfer system while retaining a substantial portion of the lubricant within the system, and introducing the composition provided herein into the heat transfer system. In some embodiments, the lubricant within the system is partially replaced.

[0091] In some embodiments, the composition provided herein can be used for replenishing the refrigerant in a chiller. For example, if the performance of a chiller using HCFC-123 has decreased due to refrigerant leakage, the composition provided herein can be added to restore the performance to its original specifications.

[0092] In some embodiments, there is provided a heat exchange system comprising the composition herein, the system being selected from the group consisting of an air conditioner, a freezer, a refrigerator, a heat pump, a chiller, a flooded evaporative cooler, a direct expansion cooler, a walk-in cooler, a heat pump, a mobile refrigerator, a mobile air conditioning unit, and systems having combinations thereof. In some embodiments, the composition provided herein can be useful in a secondary loop system where these compositions function as a primary refrigerant to provide cooling of a secondary heat transfer fluid, whereby the secondary heat transfer fluid cools a remote location.

[0093] Vapor compression refrigeration systems, air conditioning systems, and heat pump systems each include an evaporator, a compressor, a condenser, and an expansion device as components. The vapor compression cycle reuses refrigerant in multiple steps, producing a cooling effect in one step and a heating effect in a different step. The above cycle can be briefly described as follows. Liquid refrigerant enters the evaporator through the expansion device, where the liquid refrigerant boils in the evaporator, taking heat from the environment, forming vapor at a low temperature, and causing cooling. The low-pressure vapor enters the compressor, where the vapor is compressed, increasing its pressure and temperature. Next, the high-pressure (compressed) vapor refrigerant enters the condenser, where the refrigerant condenses and releases its heat to the environment. The refrigerant returns to the expansion device, through which the liquid expands from a higher pressure level in the condenser to a lower pressure level in the evaporator, thus repeating the cycle.

[0094] In some embodiments, the present application provides a heat transfer system comprising the compositions provided herein. In some embodiments, the present application provides a refrigeration, air conditioning, or heat pump device comprising the compositions provided herein. In some embodiments, the present application provides a stationary refrigeration or air conditioning device comprising the compositions provided herein. In some embodiments, the present application provides a mobile refrigeration or air conditioning device comprising the compositions provided herein.

[0095] Propellant In some embodiments, the present application provides the compositions described herein for use as a propellant (e.g., in a sprayable composition). In some embodiments, the present application provides a sprayable composition comprising the compositions provided herein. In some embodiments, active ingredients to be sprayed together with inert ingredients, solvents, and other substances may be present in the sprayable composition. In some embodiments, the sprayable composition is an aerosol. Suitable active substances for spraying include, but are not limited to, cosmetic raw materials such as deodorants, fragrances, hairsprays, detergents, and abrasives, and pharmaceuticals such as anti-asthma drugs and anti-bad breath drugs.

[0096] In some embodiments, the present application provides a process for manufacturing an aerosol product. In some embodiments, the process includes adding the compositions provided herein to one or more active ingredients within an aerosol container, and the compositions function as propellants.

Examples

[0097] The present invention will be described in more detail by way of specific examples. The following examples are provided for illustrative purposes and are not intended to limit the present invention in any way. Those skilled in the art will readily recognize various non-essential parameters that can be changed or modified to obtain essentially the same results.

[0098] Example 1. Composition of E-HFO-1336mzz and Neopentane A binary system of E-HFO-1336mzz / neopentane was investigated for potential azeotropic and near-azeotropic behavior. To determine the relative volatility of this binary system, the PTx method described herein was used. The pressure within a known volume PTx cell was measured at a constant temperature of 29.88 °C for various binary compositions. The experimental data collected are shown in Table 1 below, where X2 = liquid mole fraction of E-HFO-1336mzz; Y2 = vapor mole fraction of E-HFO-1336mzz; Pexp = experimentally measured pressure, and Pcalc = pressure calculated by the NRTL model.

[0099]

Table 1

[0100] Figure 1 shows a plot of pressure versus composition data over the composition range of liquid mole fractions of E-HFO-1336mzz from 0 to 1. The upper curve in Figure 1 represents the locus of the bubble point ("BP"), and the lower curve in Figure 1 represents the locus of the dew point ("DP"). Figure 1 shows the formation of an azeotrope at 29.88 °C with a composition of 0.552 mole fraction of E-1,1,1,4,4,4-hexafluoro-2-butene and 0.448 mole fraction of neopentane, as indicated by the maximum in the Px diagram at a pressure of 41.8 psia.

[0101] Based on these VLE data, interaction coefficients were extracted. The NRTL model was run at 10 °C intervals over the temperature range from -40 to 120 °C, and the pressure was varied so that the azeotropic condition (X2 = Y2) was satisfied. The predicted values for the E-HFO-1336mzz / neopentane azeotropic mixture are shown in Table 2.

[0102] [Table 2]

[0103] Using the NRTL model, the azeotropic mixture was predicted at 1 atm intervals over the pressure range from 1 to 30 atm, and the results are shown in Table 3.

[0104] [Table 3]

[0105] For the purpose of comparison with the experimentally measured results, this model was run at 20 °C intervals over the temperature range from -40 to 120 °C and also at 29.88 °C. At each temperature, the model was run at 0.002 intervals over the entire range of E-HFO-1336mzz liquid mole compositions from 0 to 1. Thus, the model was run for a total of 5010 combinations of temperature and E-HFO-1336mzz liquid mole composition (10 temperatures × 501 compositions = 5010). Table 4 shows representative results at 0.10 intervals of the liquid mole composition of E-HFO-1336mzz or the boundaries of near-azeotropic behavior.

[0106]

Table 4-1

[0107]

Table 4-2

[0108]

Table 4-3

[0109]

Table 4-4

[0110]

Table 4-5

[0111]

Table 4-6

[0112] Table 5 shows the near-azeotropic mixture formed between E-HFO-1336mzz and neopentane at 1 atmosphere. Table 5 shows representative data at 0.10 intervals of the liquid molar composition of E-HFO-1336mzz, or the boundaries of the near-azeotropic behavior.

[0113]

Table 5

[0114] The detailed data in Tables 4 to 5 are roughly summarized in Table 6 below. From the results in Table 5, an azeotropic mixture-like composition having a difference of 3% or less between the bubble point pressure and the dew point pressure is (1) At 1 atmosphere, E-1336mzz with a boiling point of 8.31 to 9.31 °C and a molar fraction of 0.002 to 0.016, and neopentane with a molar fraction of 0.984 to 0.998, (2) At 1 atmosphere, E-1336mzz with a boiling point of 0.95 to 1.24 °C and a molar fraction of 0.374 to 0.652, and neopentane with a molar fraction of 0.384 to 0.626, and (3) At 1 atmosphere, E-1336mzz with a boiling point of 6.31 to 7.42 °C and a molar fraction of 0.972 to 0.998, and neopentane with a molar fraction of 0.002 to 0.028, exist.

[0115] Azeotrope-like compositions in the range of 3% ([(BP-VP) / BP]×100≦3) are listed in Table 6.

[0116]

Table 6

[0117] Example 2. Composition of Z-HFO-1336mzz and Neopentane The binary system of Z-HFO-1336mzz / neopentane was investigated for potential azeotropic and near-azeotropic behavior. To determine the relative volatility of this binary system, the PTx method described in this specification was used. The pressure in a known volume of PTx cell was measured at a constant temperature of 29.90 °C for various binary compositions. The experimental data collected are shown in Table 7 below, where X2 = liquid molar fraction of neopentane; Y2 = vapor molar fraction of neopentane; Pexp = experimentally measured pressure, and Pcalc = pressure calculated by the NRTL model.

[0118]

Table 7

[0119] The vapor pressure versus neo-pentane liquid mole fraction data shown in Table 7 are plotted in Figure 2, with the experimental data points shown as solid dots. The solid line shows the prediction of the bubble point using the NRTL equation. The dashed line shows the predicted dew point. Figure 2 shows the formation of an azeotropic mixture at 29.90 °C for a composition containing 0.220 mole fraction of Z-1,1,1,4,4,4-hexafluoro-2-butene and 0.780 mole fraction of neo-pentane, as shown at a pressure of up to 31.8 psia in the Px diagram.

[0120] Based on these VLE data, the interaction coefficients were extracted. The NRTL model was run at 10 °C intervals over the temperature range of -40 to 120 °C, and the pressure was varied so that the azeotropic condition (X2 = Y2) was satisfied. The predicted azeotropic mixtures obtained for the Z-HFO-1336mzz / neo-pentane system and the experimentally determined data at 29.90 °C are shown in Table 8.

[0121]

Table 8

[0122] Using this model, the azeotropic mixtures were predicted at 1 atm intervals over the pressure range of 1 - 30 atm, and the results are shown in Table 9.

[0123]

Table 9

[0124] For the purpose of comparison with the experimentally measured results, this model was run at 20 °C intervals over the temperature range of -40 to 120 °C and also at 29.90 °C. At each temperature, the model was run at 0.002 intervals over the entire range of liquid mole fractions of Z-HFO-1336mzz from 0 to 1. Thus, the model was run for a total of 5010 combinations of temperature and liquid mole fraction of Z-HFO-1336mzz (10 (temperatures) × 501 (compositions) = 5010). Table 10 shows representative results at 0.10 intervals of the liquid mole fraction of Z-HFO-1336mzz or the boundaries of near-azeotropic behavior.

[0125]

Table 10-1

[0126]

Table 10-2

[0127]

Table 10-3

[0128]

Table 10-4

[0129]

Table 10-5

[0130] The near-azeotropic mixture formed between Z-HFO-1336mzz and neopentane at 1 atm is shown in Table 11. Table 11 shows representative data at 0.10 increments of the liquid molar composition of Z-HFO-1336mzz or the boundaries of the near-azeotropic behavior.

[0131]

Table 11

[0132] The data in Tables 10 to 11 are roughly summarized and shown in Table 12 indicating an azeotrope-like composition based on the formula [(BP-VP) / BP]×100≦3.

[0133]

Table 12

[0134] Other Embodiments 1. In some embodiments, the present application is i) Neopentane, and ii) a compound selected from E-1,1,1,4,4,4-hexafluoro-2-butene and Z-1,1,1,4,4,4-hexafluoro-2-butene, a composition comprising: E-1,1,1,4,4,4-hexafluoro-2-butene or Z-1,1,1,4,4,4-hexafluoro-2-butene is present in the composition in an amount effective to form an azeotropic composition or an azeotrope-like composition with neopentane, a composition. 2. The composition according to embodiment 1, wherein the composition comprises neopentane and E-1,1,1,4,4,4-hexafluoro-2-butene, and E-1,1,1,4,4,4-hexafluoro-2-butene is present in the composition in an amount effective to form an azeotropic composition or an azeotrope-like composition with neopentane. 3. The composition according to embodiment 1 or 2, wherein the composition comprises about 40 to about 60 mol% of neopentane and about 60 to about 40 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene. 4. The composition according to any one of embodiments 1 to 3, having a boiling point of about -40°C to about 120°C at a pressure of about 2 psi to about 390 psi. 5. The composition according to any one of embodiments 1 to 4, which is an azeotropic composition. 6. The composition according to embodiment 1 or 2, wherein the composition comprises about 40 to about 50 mol% of neopentane and about 60 to about 50 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene. 7. The composition according to any one of embodiments 1, 2, and 6, having a boiling point of about 0.9°C to about 128°C at a pressure of about 1 atm to about 30 atm. 8. The composition according to any one of embodiments 1 to 7, which is an azeotropic composition. 9. The composition according to embodiment 1 or 2, wherein the composition comprises about 98.4 to about 99.8 mol% of neopentane and about 1.6 to about 0.2 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene. 10. The composition according to any one of embodiments 1, 2, and 9, having a boiling point of about 8.3°C to about 9.3°C at a pressure of about 1 atm. 11. The composition according to embodiment 1 or 2, wherein the composition comprises from about 38.4 to about 62.6 mol% of neopentane and from about 65.2 to about 37.4 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene. 12. The composition according to any one of embodiments 1, 2, and 11, having a boiling point of from about 0.9 °C to about 1.2 °C at a pressure of about 1 atm. 13. The composition according to embodiment 1 or 2, wherein the composition comprises from about 0.2 to about 2.8 mol% of neopentane and from about 99.8 to about 97.2 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene. 14. The composition according to any one of embodiments 1, 2, and 13, having a boiling point of from about 6.3 °C to about 7.4 °C at a pressure of about 1 atm. 15. The composition comprises from about 99.8 to about 98.2 mol% of neopentane and from about 0.2 to about 1.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or from about 71.6 to about 47.6 mol% of neopentane and from about 28.4 to about 52.4 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or from about 1.2 to about 0.2 mol% of neopentane and from about 98.8 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or from about 99.8 to about 98.4 mol% of neopentane and from about 0.2 to about 1.6 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or from about 66.6 to about 40.8 mol% of neopentane and from about 33.4 to about 59.2 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or from about 1.8 to about 0.2 mol% of neopentane and from about 98.2 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or from about 62.8 to about 35.2 mol% of neopentane and from about 37.2 to about 64.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or from about 2.6 to about 0.2 mol% of neopentane and from about 97.4 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 59.8 to about 30.2 mol% of neopentane and from about 40.2 to about 69.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 3.4 to about 0.2 mol% of neopentane and from about 96.6 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 58.4 to about 28.2 mol% of neopentane and from about 41.6 to about 71.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 3.8 to about 0.2 mol% of neopentane and from about 96.2 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 57.2 to about 26.4 mol% of neopentane and from about 42.8 to about 73.6 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 4.4 to about 0.2 mol% of neopentane and from about 95.6 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 55.4 to about 23.6 mol% of neopentane and from about 44.6 to about 76.4 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 5.2 to about 99.1 mol% of neopentane and from about 94.8 to about 0.9 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 99.8 to about 98.6 mol% of neopentane and from about 0.2 to about 1.4 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 53.8 to about 23.2 mol% of neopentane and from about 46.2 to about 76.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 5.4 to about 0.2 mol% of neopentane and from about 94.6 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 56 to about 24.4 mol% of neopentane and from about 44.0 to about 75.6 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 4.6 to about 0.2 mol% of neopentane and from about 95.4 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 57.2 to about 3.8 mol% of neopentane and from about 42.8 to about 96.2 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, or From about 2.6 to about 0.2 mol% of neopentane and from about 97.4 to about 99.8 mol% of E-1,1,1,4,4,4-hexafluoro-2-butene, The composition according to Embodiment 1 or 2, comprising 16. The composition according to any one of Embodiments 1, 2, and 15, having a boiling point of about -20°C to about 120°C at a pressure of about 1 atmosphere. 17. The composition according to any one of Embodiments 1, 2, and 9-16, which is an azeotrope-like composition. 18. The composition according to Embodiment 1, wherein the composition comprises neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene, and Z-1,1,1,4,4,4-hexafluoro-2-butene is present in the composition in an amount effective to form an azeotropic composition or an azeotrope-like composition with neopentane. 19. The composition according to Embodiment 1 or 18, wherein the composition comprises from about 60 to about 93 mol% of neopentane and from about 40 to about 7 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene. 20. The composition according to any one of Embodiments 1, 18, and 19, having a boiling point of about -40°C to about 120°C at a pressure of about 1.5 psi to about 310 psi. 21. The composition according to Embodiment 1 or 18, wherein the composition comprises from about 56 to about 83 mol% of neopentane and from about 44 to about 17 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene. 22. The composition according to any one of Embodiments 1, 18, and 21, having a boiling point of about 5°C to about 145°C at a pressure of about 1 atmosphere to about 30 atmospheres. 23. The composition according to any one of Embodiments 1 and 18-21, which is an azeotropic composition. 24. The composition according to embodiment 1 or 18, wherein the composition comprises from about 99.6 to about 79.2 mol% of neopentane and from about 0.4 to about 20.8 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene. 25. The composition according to any one of embodiments 1, 18, and 24, having a boiling point of from about 7.8 °C to about 9.4 °C at a pressure of about 1 atm. 26. The composition according to embodiment 1 or 18, wherein the composition comprises from about 3.2 to about 1.6 mol% of neopentane and from about 96.8 to about 98.4 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene. 27. The composition according to any one of embodiments 1, 18, and 26, having a boiling point of from about 32.6 °C to about 33.0 °C at a pressure of about 1 atm. 28. A composition, comprising from about 99.8 to about 85.2 mol% of neopentane and from about 0.2 to about 14.8 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or comprising from about 99.8 to about 80.8 mol% of neopentane and from about 0.2 to about 19.2 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or comprising from about 99.8 to about 76.2 mol% of neopentane and from about 0.2 to about 23.8 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or comprising from about 99.8 to about 61.8 mol% of neopentane and from about 0.2 to about 38.2 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or comprising from about 0.4 to about 0.2 mol% of neopentane and from about 99.6 to about 99.8 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or comprising from about 99.8 to about 69.8 mol% of neopentane and from about 0.2 to about 30.2 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or comprising from about 99.8 to about 67.6 mol% of neopentane and from about 0.2 to about 32.4 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 99.8 to about 95.0 mol% of neopentane and about 0.2 to about 5 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 86.4 to about 63.6 mol% of neopentane and about 13.6 to about 36.4 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 0.4 to about 0.2 mol% of neopentane and about 99.6 to about 99.8 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 99.8 to about 96.6 mol% of neopentane and about 0.2 to about 3.4 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 80.6 to about 59.6 mol% of neopentane and about 19.4 to about 40.4 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 99.8 to about 97.6 mol% of neopentane and about 0.2 to about 2.4 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 74.2 to about 56.0 mol% of neopentane and about 25.8 to about 44.0 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 0.2 to about 0.8 mol% of neopentane and about 99.2 to about 99.8 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 99.8 to about 98.2 mol% of neopentane and about 0.2 to about 1.8 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 76.6 to about 50.0 mol% of neopentane and about 23.4 to about 50.0 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, or About 1.0 to about 0.2 mol% of neopentane and about 99.0 to about 99.8 mol% of Z-1,1,1,4,4,4-hexafluoro-2-butene, The composition according to embodiment 1 or 18, comprising 29. The composition according to any one of embodiments 1, 18, and 28, having a boiling point of about -20°C to about 120°C at a pressure of about 1 atmosphere. 30. The composition according to any one of Embodiments 1, 18, and 24 to 29, which is an azeotrope-like composition.

[0135] Although the present invention has been described in conjunction with its detailed description, it should be understood that the foregoing description is intended to illustrate, and not limit, the scope of the present invention as defined by the appended claims. Other aspects, advantages, and modifications are within the scope of the following claims. It should be understood by those skilled in the art related to the present invention that any of the features described herein with respect to 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 aspect and / or embodiment of the present invention described herein, and can be appropriately modified to ensure the compatibility of the combination. Such combinations are considered to be part of the present invention contemplated by this disclosure.

Claims

1. i) neopentane; ii) Z-1,1,1,4,4,4-hexafluoro-2-butene; A composition comprising: The Z-1,1,1,4,4,4-hexafluoro-2-butene is present in the composition in an amount effective to form an azeotrope or azeotrope-like composition with the neopentane.

2. 2. The composition of claim 1, wherein the composition comprises neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene, and the Z-1,1,1,4,4,4-hexafluoro-2-butene is present in the composition in an amount effective to form an azeotrope or azeotrope-like composition with the neopentane.

3. 3. The composition of claim 2, wherein the composition comprises 60 to 93 mole % neopentane and 40 to 7 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene, the mole % being based on the sum of neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene.

4. The composition of claim 3 having a boiling point of from -40°C to 120°C at a pressure of from 1.5 psi to 310 psi.

5. The composition according to claim 4, characterized in that it is an azeotropic composition.

6. 3. The composition of claim 2, wherein the composition comprises 56 to 83 mole % neopentane and 44 to 17 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene, the mole % being based on the sum of neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene.

7. The composition of claim 6 having a boiling point of from 5°C to 145°C at a pressure of from 1 atmosphere to 30 atmospheres.

8. The composition according to claim 7, characterized in that it is an azeotropic composition.

9. 3. The composition of claim 2, wherein the composition comprises 99.6 to 79.2 mole % neopentane and 0.4 to 20.8 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene, the mole % being based on the sum of neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene.

10. 10. The composition of claim 9 having a boiling point of from 7.8°C to 9.4°C at 1 atmosphere pressure.

11. The composition of claim 10, characterized as being an azeotrope-like composition.

12. 3. The composition of claim 2, wherein the composition comprises 3.2 to 1.6 mole % neopentane and 96.8 to 98.4 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene, the mole % being based on the sum of neopentane and Z-1,1,1,4,4,4-hexafluoro-2-butene.

13. 13. The composition of claim 12 having a boiling point of from 32.6°C to 33.0°C at 1 atmosphere pressure.

14. The composition of claim 13, characterized as being an azeotrope-like composition.

15. The composition, 99.8 to 85.2 mole % neopentane and 0.2 to 14.8 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene, or 99.8 to 80.8 mole % neopentane and 0.2 to 19.2 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene, or 99.8 to 76.2 mole % neopentane and 0.2 to 23.8 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene, or 99.8 to 61.8 mole % neopentane and 0.2 to 38.2 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene, or 0.4 to 0.2 mole % neopentane and 99.6 to 99.8 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene, or 99.8 to 69.8 mole % neopentane and 0.2 to 30.2 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene, or 99.8 to 67.6 mole % neopentane and 0.2 to 32.4 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene, or 99.8 to 95.0 mole % neopentane and 0.2 to 5 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene, or 86.4 to 63.6 mole % neopentane and 13.6 to 36.4 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene, or 0.4 to 0.2 mole % neopentane and 99.6 to 99.8 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene, or 99.8 to 96.6 mole % neopentane and 0.2 to 3.4 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene, or 80.6 to 59.6 mole % neopentane and 19.4 to 40.4 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene, or 99.8 to 97.6 mole % neopentane and 0.2 to 2.4 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene, or 74.2 to 56.0 mole % neopentane and 25.8 to 44.0 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene, or 0.2 to 0.8 mole % neopentane and 99.2 to 99.8 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene, or 99.8 to 98.2 mole % neopentane and 0.2 to 1.8 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene, or 76.6 to 50.0 mole % neopentane and 23.4 to 50.0 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene, or 1.0 to 0.2 mole % neopentane and 99.0 to 99.8 mole % Z-1,1,1,4,4,4-hexafluoro-2-butene 3. The composition of claim 2, comprising:

16. 16. The composition of claim 15 having a boiling point of from -20°C to 120°C at 1 atmosphere pressure.

17. 17. The composition of claim 16, characterized as being an azeotrope-like composition.

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