Azeotropic or azeotrope-like compositions containing (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)) and solvent uses thereof

Abstract

Azeotropic or azeotrope-like compositions, particularly azeotropic or azeotrope-like compositions consisting essentially of or consisting of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), ethanol, and each of methanol, as well as azeotropic or azeotrope-like compositions consisting essentially of or consisting of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), ethanol, and 1,2-trans-dichloroethylene (trans-DCE), and azeotropic or azeotrope-like compositions consisting essentially of or consisting of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), methanol, and 1,2-trans-dichloroethylene (trans-DCE), and solvent uses of the aforementioned compositions.

Description

[Technical Field]

[0001] (CROSS-REFERENCE TO RELATED APPLICATIONS) This application is a PCT international application claiming priority to U.S. Patent Application No. 18 / 543,076, filed December 18, 2023, which claims the benefit of U.S. Provisional Application No. 63 / 433,966, filed December 20, 2022, both of which are incorporated by reference in their entireties.

[0002] The present disclosure relates to azeotropic or azeotrope-like compositions, particularly azeotropic or azeotrope-like compositions consisting essentially of or consisting of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), ethanol, and each of methanol, as well as azeotropic or azeotrope-like compositions consisting essentially of or consisting of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), ethanol, and 1,2-trans-dichloroethylene (trans-DCE), and also relates to solvent uses of the aforementioned compositions. [Background technology]

[0003] Fluorocarbon fluids have desirable properties for use as heat transfer media, immersion coolants, liquid or gaseous dielectrics, industrial refrigerants, and other applications. In these applications, the use of single-component fluids or azeotrope-like mixtures, i.e., those that do not substantially fractionate upon boiling and evaporation, is particularly desirable. Unfortunately, the use of certain hydrofluorocarbons (HFCs) in industrial applications is now believed to contribute to global warming, and therefore their use is currently being curtailed. Because the formation of azeotropes is not easily predictable, identifying new, environmentally safe, non-fractionating mixtures containing HFCs is challenging. Therefore, the industry is constantly seeking new HFC-based mixtures that are acceptable and environmentally safer alternatives. Summary of the Invention

[0004] It has been discovered that certain azeotropic and azeotrope-like compositions can be produced from the combination of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)) and additional components, and in particular, the present disclosure provides minimum boiling point binary homogeneous azeotropic or azeotrope-like compositions consisting essentially of or consisting of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)) and each of ethanol and methanol, as well as (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and ethanol-methanol-methanol mixtures. and (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), ethanol, and trans-dichloroethylene (trans-DCE).

[0005] The azeotropic and azeotrope-like mixtures of the present disclosure exhibit properties that make them particularly suitable for several applications, including as solvents for cleaning, vapor degreasing, or aerosol sprays.

[0006] In one form thereof, the present disclosure provides a composition comprising an azeotropic or azeotrope-like composition consisting essentially of effective amounts of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and ethanol.

[0007] In another aspect thereof, the present disclosure provides a composition comprising an azeotropic or azeotrope-like composition consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene, wherein the (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene are arranged on a ternary diagram with the following points as vertices: Point A: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 0.9% by weight / about 8.2% by weight / about 90.9% by weight), Point B: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 0.9% by weight / about 8.2% by weight / about 90.9% by weight), Point C: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 0.9% by weight / about 8.2% by weight / about 90.9% by weight), Point D: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 0.9% by weight / about 8.2% by weight / about 90.9% by weight), Point E: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 0.9% by weight / about 8.2% by weight / about 90.9% by weight), Point F: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 0.9% by weight / about 8.2% by weight / about 90.9% by weight), Point G: ((Z)-1-chloro-2,3,3-trifluoroprop- Point A: (Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene = about 0.9% by weight / about 13.7% by weight / about 85.4% by weight), Point B: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene = about 39.6% by weight / about 8.3% by weight / about 52.1% by weight), and Point C: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene = about 41.1% by weight / about 4.9% by weight / about 54.0% by weight).

[0008] In a further aspect thereof, the present disclosure provides a composition comprising an azeotropic or azeotrope-like composition consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene, wherein the (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene form a ternary diagram with the following vertices: Point M: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 1.0 wt.% / about 1.0 wt.% / about 98.0 wt.%); Point N: ((Z)- The composition is within a quadrilateral region having: point O: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene = about 0.9% by weight / about 9.0% by weight / about 90.1% by weight); point O: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene = about 33.3% by weight / about 6.1% by weight / about 60.6% by weight); and point P: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene = about 35.5% by weight / about 0.6% by weight / about 64.1% by weight).

[0009] In a still further aspect thereof, the present disclosure provides a solvent composition comprising at least one of an effective amount of an azeotropic or azeotrope-like composition consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and methanol; an azeotropic or azeotrope-like composition consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene; and an azeotropic or azeotrope-like composition consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene.

[0010] A solvent composition comprising a binary azeotrope of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)) and ethanol may be referred to herein as solvent composition 1. Solvent composition 1 can consist essentially of a binary azeotrope of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)) and ethanol. Solvent composition 1 can consist of a binary azeotrope of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)) and ethanol.

[0011] A solvent composition comprising a binary azeotrope of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)) and methanol is sometimes referred to herein as solvent composition 2. Solvent composition 2 can consist essentially of a binary azeotrope of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)) and methanol. Solvent composition 2 can consist of a binary azeotrope of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)) and methanol.

[0012] A solvent composition comprising a ternary azeotrope of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), ethanol, and trans-dichloroethylene (trans-DCE) is sometimes referred to herein as solvent composition 3. Solvent composition 3 can consist essentially of a ternary azeotrope of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), ethanol, and trans-dichloroethylene (trans-DCE). Solvent composition 3 can consist of a ternary azeotrope of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), ethanol, and trans-dichloroethylene (trans-DCE).

[0013] A solvent composition comprising a ternary azeotrope of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), methanol, and trans-dichloroethylene (trans-DCE) is sometimes referred to herein as solvent composition 4. Solvent composition 4 can consist essentially of a ternary azeotrope of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), methanol, and trans-dichloroethylene (trans-DCE). Solvent composition 4 can consist of a ternary azeotrope of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), methanol, and trans-dichloroethylene (trans-DCE). [Brief explanation of the drawings]

[0014] [Figure 1] 1 shows the boiling point temperature change of mixtures of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)) and methanol at ambient pressure according to Example 1. [Figure 2] 1 shows the boiling point temperature change of mixtures of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)) and ethanol at ambient pressure according to Example 2. [Figure 3] FIG. 1 shows the evolution of boiling point temperature for mixtures of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), methanol, and trans-dichloroethylene (trans-DCE) at ambient pressure, with a fixed mass ratio of methanol to trans-DCE held at 0.1173, according to Example 3. [Figure 4] FIG. 1 shows the evolution of boiling point temperature for mixtures of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), methanol, and trans-dichloroethylene (trans-DCE) at ambient pressure, keeping the mass ratio of HCFO-1233yd(Z) to trans-DCE fixed at 0.0840, according to Example 3. [Figure 5] FIG. 1 shows the change in boiling point temperature of mixtures of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), ethanol, and trans-dichloroethylene (trans-DCE) at ambient pressure, with the ethanol to trans-DCE mass ratio held fixed at 0.0595, according to Example 4. [Figure 6] FIG. 1 shows the evolution of boiling point temperature for mixtures of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), ethanol, and trans-dichloroethylene (trans-DCE) at ambient pressure, with a fixed mass ratio of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)) to trans-dichloroethylene (trans-DCE) held at 0.3538, according to Example 4. [Figure 7A] FIG. 1 is a ternary composition diagram of an azeotropic or azeotrope-like composition of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), methanol, and trans-dichloroethylene (trans-DCE). [Figure 7B] FIG. 7B is a fragmentary view of a portion of FIG. 7A. [Figure 8A] FIG. 1 is a ternary composition diagram of an azeotropic or azeotrope-like composition of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), ethanol, and trans-dichloroethylene (trans-DCE). [Figure 8B] FIG. 8B is a fragmentary view of a portion of FIG. 8A. DETAILED DESCRIPTION OF THE INVENTION

[0015] I. Definition and Description of Azeotropic or Azeotrope-Like Compositions An "azeotropic" composition is a unique combination of two, three, or more components. Azeotropic compositions can be characterized in various ways. For example, at a given pressure, an azeotropic composition will either boil at a characteristic temperature higher than the higher-boiling component (a maximum boiling point azeotrope) or will boil at a characteristic temperature lower than the lower-boiling component (a minimum boiling point azeotrope). At this characteristic temperature, the same composition exists in both the vapor and liquid phases. Azeotropic compositions do not separate upon boiling or evaporation. Therefore, the components of an azeotropic composition cannot be separated during a phase change.

[0016] Azeotropic compositions are also characterized by a characteristic azeotropic temperature, where the bubble point pressure of the liquid phase is the same as the dew point pressure of the vapor phase.

[0017] The behavior of azeotropic compositions contrasts with that of non-azeotropic compositions, in which the liquid composition changes to a significant extent during boiling or evaporation.

[0018] For purposes of this disclosure, an azeotropic composition is characterized as a composition that boils at a characteristic temperature below the boiling points of two or more components (minimum boiling point azeotrope), thereby having the same composition in both the vapor and liquid phases.

[0019] Those skilled in the art will understand that at different pressures, both the composition and boiling point of an azeotropic composition will vary to some extent. Thus, depending on temperature and / or pressure, an azeotropic composition may have a variable composition. Thus, those skilled in the art will understand that an azeotropic composition can be defined using a composition range rather than a fixed composition. Furthermore, an azeotrope can also be defined in terms of the exact weight percentage of each component of a composition characterized by a fixed boiling point at a particular pressure.

[0020] An "azeotrope-like" composition is a composition of two, three, or more components that behaves substantially as an azeotrope. Thus, for purposes of this disclosure, an azeotrope-like composition is a combination of two, three, or more different components that, when in liquid form at a given pressure, boils at a substantially constant temperature and provides substantially the same gas composition as the boiling liquid composition.

[0021] Azeotropic or azeotrope-like compositions can be identified in a number of different ways.

[0022] For purposes of this disclosure, azeotropic or azeotrope-like compositions are experimentally identified using an ebullometer (Walas, Phase Equilibria in Chemical Engineering, Butterworth-Heinemann, 1985, 533-544). The ebullometer is designed to provide a highly accurate measurement of the boiling point of a liquid by measuring the vapor-liquid equilibrium temperature.

[0023] The boiling points of each of the components alone are measured at a constant pressure. As will be understood by those skilled in the art, for two-component azeotropic or azeotrope-like compositions, the boiling point of one of the components of the composition is first measured. Then, the second component of the composition is added in varying amounts, and the boiling points of each of the resulting compositions are measured using an ebullometer at that constant pressure.

[0024] The measured boiling points are plotted against the composition of the tested composition, e.g., in the case of a binary azeotrope, against the amount of the second component added to the composition (expressed either as mass or weight %, wt. %, or mol %). The presence of an azeotropic composition can be identified by observing a maximum or minimum boiling temperature that is higher or lower than the boiling point of either component alone.

[0025] As will be understood by those skilled in the art, identification of an azeotropic or azeotrope-like composition is made by comparing the change in the boiling point of the composition upon addition of a second component to the first component with the boiling point of the first component. Thus, it is not necessary to calibrate the system to the reported boiling point of a particular component in order to measure the change in boiling point.

[0026] As used herein, the term "(Z)-1-chloro-2,3,3-trifluoroprop-1-ene" refers to HCFO-1233yd(Z), which can be abbreviated as HCFO-1233yd(Z) or R-1233yd(Z).

[0027] As used herein, the term "trans-dichloroethylene" refers to trans-1,2-dichloroethene, which may be abbreviated as trans-DCE.

[0028] As used herein, with respect to components of an azeotropic or azeotrope-like composition or mixture, the term "consisting essentially of" means that the composition contains the indicated components in the azeotropic or azeotrope-like ratio and may contain additional components, provided that the additional components do not form a new azeotropic or azeotrope-like system. For example, an azeotrope consisting essentially of two compounds forms a binary azeotrope and may optionally include one or more additional components, provided that the additional components do not render the mixture non-azeotropic or form azeotropes with either or both of the compounds (e.g., do not form ternary or higher azeotropes). Similarly, an azeotrope consisting essentially of three compounds forms a ternary azeotrope and may optionally include one or more additional components, provided that the additional components do not render the mixture non-azeotropic or form azeotropes with either or both of the compounds (e.g., do not form quaternary or higher azeotropes).

[0029] As used herein, the singular forms "a," "an," and "the" include the plural unless the context clearly dictates otherwise. Furthermore, when an amount, concentration, or other value or parameter is given as either a range, a preferred range, or a list of upper and lower preferred values, this should be understood as specifically disclosing all ranges formed from any pairing of any upper range or upper preferred value with any lower range or lower preferred value, regardless of whether the ranges are separately disclosed. When a range of numerical values ​​is recited herein, unless otherwise specified, the range is intended to include its endpoints, and all integers and fractions within the range. The scope of the present disclosure is not intended to be limited to the specific values ​​recited when defining a range.

[0030] As used herein, the phrase "within any range defined between any two of the preceding values" means that any range may be selected from any two of the values ​​listed before such phrase, regardless of whether those values ​​are in the lower portion of the list or the upper portion of the list. For example, a pair of values ​​may be selected from two lower values, two higher values, or a lower value and an upper value.

[0031] As used herein, the term "effective amount" is the amount of each component that, when combined with the other component, results in the formation of an azeotropic or azeotrope-like mixture.

[0032] As previously mentioned, at a minimum or maximum boiling point, the composition of the vapor phase is the same as the composition of the liquid phase. Thus, an azeotrope-like composition is a composition of components that provides a substantially constant minimum or maximum boiling point, at which the composition of the vapor phase is substantially the same as the composition of the liquid phase.

[0033] II. Azeotropic or azeotrope-like compositions of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and methanol (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)) has been found to form homogeneous minimum boiling point azeotropic and azeotrope-like compositions or mixtures with methanol, and the present disclosure provides a homogeneous azeotropic or azeotrope-like composition comprising (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and methanol. The azeotropic or azeotrope-like composition preferably consists essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and methanol. The azeotropic or azeotrope-like composition may consist of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and methanol.

[0034] The present inventors have experimentally found that (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and methanol form an azeotrope or azeotrope-like composition.

[0035] The present disclosure provides an azeotropic or azeotrope-like composition consisting essentially of effective amounts of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and methanol to form an azeotropic or azeotrope-like composition.

[0036] The present disclosure also provides a method for forming an azeotropic or azeotrope-like composition by combining effective amounts of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and methanol. Any of a wide variety of methods known in the art for combining two or more components to form a composition can be used in this method. For example, (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and methanol can be mixed, blended, or otherwise combined manually and / or mechanically as part of a batch or continuous reaction and / or process, or via a combination of two or more such processes. Both (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and methanol are commercially available and can be obtained from several different vendors. These components can be provided in the required amounts, for example, by weighing and then combining these amounts.

[0037] Preferably, the azeotropic or azeotrope-like composition may comprise about 88% to 98% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, preferably about 89.5% to 93.7% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, or preferably about 90.01% to 92.52% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, and about 12% to 2% by weight of methanol, preferably about 10.5% to 6.3% by weight of methanol, or preferably about 9.99% to 7.48% by weight of methanol. The azeotropic or azeotrope-like composition may also comprise about 91.1% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and 8.9% by weight of methanol. Preferably, the azeotropic or azeotrope-like compositions of the present disclosure have a boiling point of about 49.680°C ± 0.001°C at a pressure of about 14.7 psia ± 0.2 psia.

[0038] In other words, the azeotropic or azeotrope-like composition comprises, consists essentially of, or consists of about 88 wt% to 98 wt% R1233yd(Z) and 12 wt% to 2 wt% methanol, about 89.5 wt% to 93.7 wt% R1233yd(Z) and 10.5 wt% to 6.3 wt% methanol, about 90.01 wt% to 92.52 wt% R1233yd(Z) and 9.99 wt% to 7.48 wt% methanol, or about 91.1 wt% R1233yd(Z) and 8.9 wt% methanol.

[0039] The azeotrope-like composition can comprise about 88% to 94% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, preferably about 90.0% to 92.2% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, or preferably about 90.6% to 91.7% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, and about 12% to 6% by weight of methanol, preferably about 10.0% to 7.8% by weight of methanol, or preferably about 9.4% to 8.3% by weight of methanol.

[0040] A true azeotrope is about 91.1 wt. % (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and 8.9 wt. % methanol, with a boiling point of about 49.66° C.±0.01° C. at a pressure of about 14.7 psia±0.2 psia.

[0041] In other words, the azeotropic or azeotrope-like composition consists essentially of, or consists of, about 88% to 94% by weight HCFO-1233yd(Z) and 12% to 6% by weight methanol, about 90.0% to 92.2% by weight HCFO-1233yd(Z) and 10.0% to 7.8% by weight methanol, about 90.6% to 91.7% by weight HCFO-1233yd(Z) and 9.4% to 8.3% by weight methanol, or about 91.1% by weight HCFO-1233yd(Z) and 8.9% by weight methanol.

[0042] The azeotropic or azeotrope-like composition may preferably consist essentially of, or consist of, the above amounts of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and methanol.

[0043] The present disclosure also provides compositions, preferably solvent compositions, comprising azeotropic or azeotrope-like compositions. For example, compositions, preferably solvent compositions, comprising at least about 5% by weight of azeotropic or azeotrope-like compositions, or at least about 15% by weight of azeotropic or azeotrope-like compositions, or at least about 50% by weight of azeotropic or azeotrope-like compositions, or at least about 70% by weight of azeotropic or azeotrope-like compositions, or at least about 90% by weight of azeotropic or azeotrope-like compositions are provided.

[0044] III. Azeotropic or azeotrope-like compositions of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and ethanol (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)) has also been found to form homogeneous minimum boiling point azeotropic and azeotrope-like compositions or mixtures with ethanol, and the present disclosure provides a homogeneous azeotropic or azeotrope-like composition consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and ethanol. The azeotropic or azeotrope-like composition may preferably consist essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and ethanol, or may consist essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and ethanol, or the azeotropic or azeotrope-like composition may consist of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and ethanol.

[0045] The present inventors have experimentally found that (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and ethanol form an azeotrope or azeotrope-like composition.

[0046] An azeotropic or azeotrope-like composition of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and ethanol is a binary azeotrope that contains only the two aforementioned components and no other components.

[0047] The present disclosure provides an azeotropic or azeotrope-like composition consisting essentially of effective amounts of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and ethanol to form an azeotropic or azeotrope-like composition.

[0048] The present disclosure also provides a method for forming an azeotropic or azeotrope-like composition by mixing, combining, or blending effective amounts of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and ethanol. Any of a wide variety of methods known in the art for combining two or more components to form a composition can be used in this method. For example, (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and methanol can be mixed, blended, or otherwise combined manually and / or mechanically as part of a batch or continuous reaction and / or process, or via a combination of two or more such processes. Both (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and ethanol are commercially available and can be obtained from several different vendors. These components can be provided in the required amounts, for example, by weighing and then combining these amounts.

[0049] Preferably, the azeotropic or azeotrope-like composition comprises about 89.5% to 99.9% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, preferably about 90% to 98.0% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, or preferably about 95.04% to 96.02% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, and about 0.1% to 10.5% by weight of ethanol, preferably about 2% to 10% by weight of ethanol, or preferably about 3.98% to 4.96% by weight of ethanol. The azeotropic or azeotrope-like composition may also comprise about 95.9% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and 4.1% by weight of ethanol. Preferably, the azeotropic or azeotrope-like compositions of the present disclosure have a boiling point of about 53.506°C ± 0.001°C at a pressure of about 14.7 psia ± 0.2 psia.

[0050] In other words, the azeotropic or azeotrope-like composition comprises, consists essentially of, or consists of about 89.5% to 99.9% by weight R1233yd(Z) and 0.1% to 10.5% by weight ethanol, about 90% to 98.0% by weight R1233yd(Z) and 2% to 10% by weight ethanol, about 95.04% to 96.02% by weight R1233yd(Z) and 3.98% to 3.46% by weight ethanol, or about 95.9% by weight R1233yd(Z) and 4.1% by weight ethanol.

[0051] The azeotrope-like composition can comprise about 92.5% to 99.9% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, preferably about 94.8% to 97.5% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, or preferably about 95.3% to 96.4% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, and about 7.5% to 0.1% by weight of ethanol, preferably about 5.2% to 2.5% by weight of ethanol, or preferably about 4.7% to 3.6% by weight of ethanol.

[0052] A true azeotrope is about 95.9 wt. % (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and 4.1 wt. % ethanol, and has a boiling point of about 53.50° C.±0.01° C. at a pressure of about 14.7 psia±0.2 psia.

[0053] In other words, the azeotropic or azeotrope-like composition consists essentially of, or consists of, about 92.5% to 99.9% by weight HCFO-1233yd(Z) and 7.5% to 0.1% by weight ethanol, about 94.8% to 97.5% by weight HCFO-1233yd(Z) and 5.2% to 2.5% by weight ethanol, about 95.3% to 96.4% by weight HCFO-1233yd(Z) and 4.7% to 3.6% by weight ethanol, or about 95.9% by weight HCFO-1233yd(Z) and 4.1% by weight ethanol.

[0054] The azeotropic or azeotrope-like composition can consist essentially of the above amounts of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and ethanol, or can consist of the above amounts of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and ethanol.

[0055] The present disclosure also provides compositions comprising azeotropic or azeotrope-like compositions, such as at least about 5% by weight of azeotropic or azeotrope-like compositions, or at least about 15% by weight of azeotropic or azeotrope-like compositions, or at least about 50% by weight of azeotropic or azeotrope-like compositions, or at least about 70% by weight of azeotropic or azeotrope-like compositions, or at least about 90% by weight of azeotropic or azeotrope-like compositions.

[0056] IV. Ternary azeotrope or azeotrope-like composition of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)) has been found to form homogeneous, minimum boiling point azeotropic and azeotrope-like compositions or mixtures with methanol and trans-dichloroethylene (trans-DCE), and the present disclosure provides a homogeneous azeotropic or azeotrope-like composition, preferably consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene. The azeotropic or azeotrope-like composition may consist of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene.

[0057] It has been experimentally shown that (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene form azeotropic or azeotrope-like compositions.

[0058] An azeotropic or azeotrope-like composition of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene may be a ternary azeotrope containing only the aforementioned three components and no other components.

[0059] The azeotropic or azeotrope-like composition of the present invention may preferably consist essentially of a combination of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene. The azeotropic or azeotrope-like composition of the present invention may consist of a combination of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene.

[0060] The present disclosure also provides a method for forming an azeotropic or azeotrope-like composition by combining effective amounts of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene. Any of a wide variety of methods known in the art for combining two or more components to form a composition can be used in this method. For example, (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene can be mixed, blended, or otherwise combined manually and / or mechanically as part of a batch or continuous reaction and / or process, or via a combination of two or more such processes. Each of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene is commercially available and can be obtained from several different vendors. These components can be provided in the required amounts, for example, by weighing and then combining these amounts.

[0061] 7A and 7B are ternary composition diagrams having (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), methanol, and trans-dichloroethylene (trans-DCE), the total concentration of the foregoing being 100% by weight, with the following points (or compositions) as vertices of the boundary composition of a quadrilateral of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), methanol, and trans-dichloroethylene (trans-DCE):

[0062] As shown in Figures 7A and 7B, the azeotropic or azeotrope-like composition of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), methanol, and trans-dichloroethylene (trans-DCE) may preferably consist essentially of compositions within the area bounded by points (or compositions) "A," "B," "C," and "D," with point "A" representing 0.9 / 8.2 / 90.9 wt.% HCFO-1233yd(Z)." 233yd(Z) / methanol / trans-DCE, point "B" is 0.9 / 13.7 / 85.4 wt% HCFO-1233yd(Z) / methanol / trans-DCE, point "C" is 39.6 / 8.3 / 52.1 wt% HCFO-1233yd(Z) / methanol / trans-DCE, and point "D" is 41.1 / 4.9 / 54.0 wt% HCFO-1233yd(Z) / methanol / trans-DCE.

[0063] More preferably, the azeotropic or azeotrope-like composition of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), methanol, and trans-dichloroethylene (trans-DCE) may consist essentially of compositions within the area bounded by points (or compositions) "E," "F," "G," and "H," where point "E" is 3.9 / 8.7 / 87.4 wt.% HCFO-1233yd(Z)). % HCFO-1233yd(Z) / methanol / trans-DCE, point "F" is 3.8 / 11.8 / 84.4 wt.% HCFO-1233yd(Z) / methanol / trans-DCE, point "G" is 27.4 / 8.9 / 63.7 wt.% HCFO-1233yd(Z) / methanol / trans-DCE, and point "H" is 28.1 / 6.5 / 65.4 wt.% HCFO-1233yd(Z) / methanol / trans-DCE.

[0064] Most preferably, the azeotropic or azeotrope-like composition of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), methanol, and trans-dichloroethylene (trans-DCE) may consist essentially of compositions within the area bounded by points (or compositions) "I," "J," "K," and "L," where point "I" is 6.7 / 9.2 / 84.1 wt. % HCFO-1233yd(Z)." (Z) / methanol / trans-DCE, point "J" is 6.7 / 10.0 / 83.3 wt% HCFO-1233yd(Z) / methanol / trans-DCE, point "K" is 7.4 / 9.9 / 82.7 wt% HCFO-1233yd(Z) / methanol / trans-DCE, and point "L" is 7.5 / 9.2 / 83.3 wt% HCFO-1233yd(Z) / methanol / trans-DCE.

[0065] The azeotropic composition may also consist essentially of about 7.02 weight percent (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, about 9.85 weight percent methanol, and about 83.13 weight percent trans-dichloroethylene.

[0066] Preferably, the azeotropic compositions of the present disclosure have a boiling point of about 41.746°C ± 0.001°C at a pressure of about 14.7 psia ± 0.2 psia.

[0067] V. Ternary azeotropic or azeotrope-like composition of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)) has been found to form homogeneous, minimum boiling point azeotropic and azeotrope-like compositions or mixtures with ethanol and trans-dichloroethylene (trans-DCE), and the present disclosure provides a preferred homogeneous azeotropic or azeotrope-like composition consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene. The azeotropic or azeotrope-like composition may consist of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene.

[0068] (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene were found to form azeotropic or azeotrope-like compositions.

[0069] An azeotropic or azeotrope-like composition of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene may be a ternary azeotrope containing only the aforementioned three components and no other components.

[0070] The azeotropic or azeotrope-like composition of the present invention may preferably consist essentially of a combination of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene. The azeotropic or azeotrope-like composition of the present invention may consist of a combination of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene.

[0071] The present disclosure also provides a method for forming an azeotropic or azeotrope-like composition by combining effective amounts of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene. Any of a wide variety of methods known in the art for combining two or more components to form a composition can be used in this method. For example, (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene can be mixed, blended, or otherwise combined manually and / or mechanically as part of a batch or continuous reaction and / or process, or via a combination of two or more such processes. Each of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene is commercially available and can be obtained from several different vendors. These components can be provided in the required amounts, for example, by weighing and then combining these amounts.

[0072] 8A and 8B are ternary composition diagrams having (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), ethanol, and trans-dichloroethylene (trans-DCE), the total concentration of the foregoing being 100% by weight, with the following points (or compositions) as vertices of the boundary composition of a quadrilateral of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), ethanol, and trans-dichloroethylene (trans-DCE):

[0073] As shown in Figures 8A and 8B, the azeotropic or azeotrope-like composition of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), ethanol, and trans-DCE may preferably consist essentially of compositions within the area bounded by points (or compositions) "M," "N," "O," and "P," where point "M" is 1.0 / 1.0 / 98.0 wt.% HCFO-1233yd(Z). ) / 5 ethanol / trans-DCE, point "N" is 0.9 / 9.0 / 90.1 wt% HCFO-1233yd(Z) / ethanol / trans-DCE, point "O" is 33.3 / 6.1 / 60.6 wt% HCFO-1233yd(Z) / ethanol / trans-DCE, and point "P" is 35.3 / 0.6 / 64.1 wt% HCFO-1233yd(Z) / ethanol / trans-DCE.

[0074] More preferably, the azeotropic or azeotrope-like composition of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), ethanol, and trans-dichloroethylene (trans-DCE) may consist essentially of compositions within the area bounded by points (or compositions) "Q," "R," "S," and "T," where point "Q" is 13.4 / 2.5 / 84.1 wt.% HCFO-1233yd(Z)). % HCFO-1233yd(Z) / enol / trans-DCE, point "R" is 12.9 / 6.5 / 80.6 wt.% HCFO-1233yd(Z) / ethanol / trans-DCE, point "S" is 31.6 / 5.1 / 63.3 wt.% HCFO-1233yd(Z) / ethanol / trans-DCE, and point "T" is 32.7 / 2.0 / 65.3 wt.% HCFO-1233yd(Z) / ethanol / trans-DCE.

[0075] Most preferably, the azeotropic or azeotrope-like composition of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), ethanol, and trans-dichloroethylene (trans-DCE) may consist essentially of compositions within the area bounded by points (or compositions) "U," "V," "W," and "X," where point "U" is 22.2 / 3.7 / 74.1 wt. % HCFO-1233yd(Z) (Z) / enol / trans-DCE, point "V" is 22.1 / 4.4 / 73.5 wt% HCFO-1233yd(Z) / ethanol / trans-DCE, point "W" is 27.4 / 4.1 / 68.5 wt% HCFO-1233yd(Z) / ethanol / trans-DCE, and point "X" is 27.6 / 3.4 / 69.0 wt% HCFO-1233yd(Z) / ethanol / trans-DCE.

[0076] The azeotropic composition may also consist essentially of about 25.04 wt.% (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, about 4.11 wt.% ethanol, and about 70.85 wt.% trans-dichloroethylene.

[0077] Preferably, the azeotropic compositions of the present disclosure have a boiling point of about 45.560°C ± 0.002°C at a pressure of about 14.7 psia ± 0.2 psia.

[0078] VI. Solvent Uses of Azeotropic and Azeotrope-Like Compositions Containing (Z)-1-Chloro-2,3,3-trifluoroprop-1-ene The present disclosure contemplates solvent compositions comprising azeotropic or azeotrope-like compositions of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)) with ethanol, methanol, ethanol and trans-dichloroethylene (trans-DCE), or methanol and trans-dichloroethylene (trans-DCE), and solvent uses thereof, i.e., solvent uses of solvent compositions 1 to 4.

[0079] Each of solvent compositions 1-4 may comprise, consist essentially of, or consist of an azeotropic or azeotrope-like composition in an amount of at least about 5%, preferably at least about 15%, more preferably at least about 30%, more preferably at least about 50%, more preferably at least about 60%, more preferably at least about 70%, more preferably at least about 90%, more preferably at least about 95%, and more preferably at least about 99% by weight of the solvent composition.

[0080] It will be understood that any of the above amounts can be used to provide endpoints for ranges of the amount of azeotropic or azeotrope-like composition in the solvent composition. For example, the azeotropic or azeotrope-like composition may be present in an amount of about 1% to about 99% by weight of the composition, or about 5% to 95% by weight of the composition, or about 10% to about 90% by weight of the composition, or about 15% to about 70% by weight of the composition, or about 30% to about 60% by weight of the composition, or about 40% to 50% by weight of the composition, or about 90% to about 99% by weight of the composition.

[0081] It will be appreciated that solvent compositions 1-4 can consist essentially of azeotropic or azeotrope-like compositions.Solvent compositions 1-4 can consist of azeotropic or azeotrope-like compositions.

[0082] Each of solvent compositions 1-4 may independently contain one or more cosolvents selected from the group consisting of linear, branched, or cyclic hydrocarbons, ketones, esters, ethers, acetals, trans-dichloroethylene (trans-DCE), alcohols (preferably methanol, ethanol, or propanol), HCFO-1233zd(E), HCFO-1233zd(Z), HCFO-1336mzz(E), HCFO-1336mzz(Z), HFE-347, methoxytridecafluoroheptene isomers, and combinations thereof. Preferred cosolvents include trans-DCE, ethanol, and propanol. It will be understood that the propanol may be n-propanol or isopropanol, preferably isopropanol.

[0083] The co-solvent may be present in an amount of at least about 1%, at least about 10%, at least about 30%, at least about 50%, at least about 70%, at least about 90%, or at least about 99% by weight of the composition.

[0084] It will be understood that any of the above amounts can be used to provide endpoints for ranges of the amount of cosolvent in the solvent composition. For example, the cosolvent may be present in an amount of about 1% to about 99% by weight of the composition, or about 10% to about 90% by weight of the composition, or about 30% to about 70% by weight of the composition, or about 40% to about 50% by weight of the composition, or about 1% to about 10% by weight of the composition, or about 40% to about 90% by weight of the composition.

[0085] It will be understood that each of solvent compositions 1-4 may comprise, consist essentially of, or consist of an azeotropic or azeotrope-like composition and one or more specific co-solvents.

[0086] When the co-solvent is an alcohol (preferably ethanol or propanol), it is preferably present in an amount of about 1% to about 10% by weight of the solvent composition. The azeotropic or azeotrope-like composition is present in an amount of about 90% to about 99% by weight of the solvent composition. Solvent compositions 1-4 may consist essentially of the azeotropic or azeotrope-like composition and an alcohol (preferably ethanol or propanol). The solvent composition may consist of the azeotropic or azeotrope-like composition and an alcohol (preferably ethanol or propanol). The propanol may be n-propanol or isopropanol, preferably isopropanol.

[0087] Each of the solvent compositions 1 to 4 preferably has a GWP of about 1000 or less, more preferably about 500 or less, and more preferably about 150 or less.

[0088] Each of Solvent Compositions 1-4 may contain corrosion inhibitors, surfactants, stabilizers, inhibitors, and other adjuvants that aid or enhance the functionality of the composition. Examples of stabilizers include nitroalkanes, epoxyalkanes, and phosphites.

[0089] As an embodiment of the present invention, solvent compositions 1-4 described herein can be used as solvents in cleaning a variety of polar contaminants or stains, such as rosin-based fluxes, water-based machining fluids, fingerprints, lubricants, or in removing coatings, such as paints and adhesives, from a variety of substrates by wiping, vapor degreasing, aerosol, or other means. In certain preferred embodiments, the cleaning compositions can be used in vapor degreasing, wiping, and aerosol-sprayable applications.

[0090] Thus, the present invention relates to the use of a composition comprising the azeotropic or azeotrope-like composition disclosed herein as a solvent, where the composition can optionally include a co-solvent. Preferably, the co-solvent is an alcohol selected from ethanol, n-propanol, or isopropanol. Alternatively, the composition can consist essentially of the azeotropic or azeotrope-like composition disclosed herein.

[0091] When an alcohol is used in solvent compositions 1 to 4, the azeotropic or azeotrope-like composition can effectively remove polar contaminants that are not effectively removed by (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)) alone.

[0092] The present invention provides a method for removing contaminants from an article, comprising contacting the contaminated article with any of solvent compositions 1-4. Preferably, the method involves applying any of solvent compositions 1-4 to the contaminant-containing article by vapor degreasing or solvent cleaning methods. Such methods are particularly preferred for certain applications, particularly intricate parts and applications where soil removal is difficult. As will be appreciated by those skilled in the art, the present methods are applicable to a wide variety of different cleaning and residue removal techniques, all of which are within the broad scope of the present invention.

[0093] Preferred vapor degreasing and solvent cleaning methods involve exposing an article to vapors of a boiling solvent composition, preferably at room temperature (e.g., about 25°C). The vapors that condense on the object have the advantage of providing a relatively clean distilled solvent for washing away grease or other contaminants. Thus, such processes have the added advantage that relatively little residue is left behind by the eventual evaporation of the solvent composition from the object, compared to when the object is simply washed in a liquid solvent.

[0094] In applications where the article contains difficult-to-remove contaminants, the method preferably includes elevating the temperature of solvent compositions 1-4 above ambient temperature (e.g., above about 25°C), or to any other temperature effective to substantially enhance the cleaning action of the solvent in such applications. Such processes are also generally preferred in large-scale assembly line operations where cleaning of articles, particularly metal parts and assemblies, should be performed efficiently and quickly.

[0095] Preferably, the cleaning method of the present invention involves immersing the article to be cleaned in a liquid solvent at an elevated temperature, even more preferably near the boiling point of the solvent composition. In such an operation, this step preferably removes a significant amount, even more preferably a majority, of the target contaminants from the article. This step is then preferably followed by immersion of the article in a solvent, preferably freshly distilled solvent, at a temperature lower than the temperature of the liquid solvent in the previous immersion step, preferably at ambient or near room temperature (e.g., about 25°C). The preferred method also includes a subsequent step of contacting the article with the relatively hot vapors of the present solvent composition, preferably by exposing the article to solvent vapors rising from the hot / boiling solvent in connection with the first-mentioned immersion step. This preferably results in condensation of the solvent vapor on the article. It will be understood that the article may also be sprayed with distilled solvent before the final rinse.

[0096] It is contemplated that many types and styles of vapor degreasing equipment can be used in connection with the present method. One example of such equipment and its operation is disclosed by Sherliker et al. in U.S. Patent No. 3,085,918, which is incorporated herein by reference. The equipment disclosed in Sherliker et al. includes a boiling sump for containing the solvent composition, a clean sump for containing the distillation solvent, a water separator, and other auxiliary equipment.

[0097] The cleaning method may also include low-temperature washing, in which the contaminated article is either immersed in any of the solvent compositions 1-4 under ambient or room temperature conditions (e.g., about 25° C.) or wiped with a solvent-soaked cloth or the like under such conditions. In addition, the method may include applying the solvent composition to the article by spraying the composition onto the article.

[0098] Each of solvent compositions 1-4 can effectively displace water from a wide range of substrates, including, but not limited to, metals such as stainless steel, aluminum alloys, and brass; glass and ceramic surfaces such as glass, borosilicate glass, and matte alumina; silica such as silicon wafers; calcined alumina; etc. Furthermore, solvent compositions 1-4 either do not form significant emulsions with the displaced water or form only minor amounts of such emulsions.

[0099] Each of solvent compositions 1-4 can be used to clean and / or dry non-absorbent substrates and articles composed of materials such as metal, glass, ceramic, etc. Accordingly, the present invention provides a method for drying the surface of a substrate, comprising contacting the substrate with any of solvent compositions 1-4 and then removing the solvent composition from the article.

[0100] The method of contact is not critical and can vary widely. For example, the article can be immersed in a container of the composition, or the article can be sprayed with the composition. Complete immersion of the article is preferred to ensure contact of all exposed surfaces of the article with the composition. Any method capable of providing such contact can be used. Typically, the contact time is up to about 10 minutes, but this time is not critical and longer times can be used if necessary.

[0101] The contacting temperature can also vary widely depending on the boiling point of the solvent composition. Generally, the temperature is equal to or less than about such boiling point. After the contacting step, the article is removed from contact with the composition, and any composition adhering to the exposed surface of the article is removed by any conventional means, such as evaporation.

[0102] Each of solvent compositions 1-4 can be used in aerosol and / or sprayable compositions. Preferably, the aerosol and / or sprayable compositions may have one or more additives designed for this use, such as propellants, propellants, etc.

[0103] Each of the solvent compositions 1 to 4 can be used as a carrier. For example, the solvent composition can be used as a carrier for organic substances such as lubricants, coating materials, release agents, water / oil repellents, oils, or greases. The oil can be mineral oil, cutting oil, or silicone oil.

[0104] It will also be appreciated that each of solvent compositions 1-4 may be used as a carrier for a flavor or fragrance formulation.

[0105] In the manufacture of electronic circuit assemblies, contaminants can accumulate throughout the various steps of the manufacturing process. One of the final steps in the manufacturing process is the application of soldering flux, followed by various soldering operations. The cleanliness of electronic circuit assemblies, such as printed circuit boards, is important for their proper function and reliability. However, in practice, these fluxes have proven difficult to effectively remove. Therefore, each of solvent compositions 1-4 can be used to clean electronic circuit assemblies, such as printed circuit boards, during their manufacture. In this use, the solvent composition can clean solder flux residue from the electronic circuit assemblies. The solder flux may be a rosin or non-rosin (or water-soluble) flux.

[0106] Each of solvent compositions 1-4 can be used to solvate oils, such as mineral oil, cutting oil, or silicone oil.

[0107] Each of solvent compositions 1-4 can also be used as an extractant, for example, to extract organic compounds (e.g., to extract biomass or flavorings from plant material). [Example]

[0108] Ebriometer Test - Dual Method For Examples 1 and 2 below, boiling point temperatures were measured using an isobaric ebullometer consisting of five sections: (1) boiler, (2) equilibrium section, (3) reservoir, (4) Cottrell lift pump, and (5) condenser. The Cottrell lift pump was used to transport liquid and vapor from the boiler area to the equilibrium section. The top of the ebullometer, or reflux condenser, was cooled with a circulating cooling fluid (50 / 50 water / propylene glycol) to reach a temperature of approximately 15°C, which was significantly lower than the normal boiling points of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), 54.106°C, methanol, 64.7°C, ethanol, 78.37°C, and trans-dichloroethylene (trans-DCE), 47.7°C, all at 14.7 psia. In this way, all vapor condensed and flowed back into the equilibrium section, where a calibrated resistance temperature detector (RTD) with a measurement / error accuracy of ±0.001°C was installed, to achieve equilibrium between the liquid and vapor phases.

[0109] An isobaric ebullometer was used to measure the boiling point temperatures of the pure and mixed fluids at ambient pressure, set via a pressure controller maintaining a nitrogen atmosphere of 14.7 psia. Approximately 50 mL of the first fluid was charged to a boiler and heated to reflux, which pumped the vapor / liquid through a Cottrell pump to the reflux condenser and equilibration section. Once the temperature of the condensed fluid reached a constant value, measured increments of the second fluid were added to the boiler. Sufficient delay time was allowed between multiple additions of the second fluid to achieve proper mixing and thermodynamic equilibrium of the two fluids.

[0110] Measurements were performed by first introducing approximately 1 to 5 mL of ethanol or methanol, with a purity greater than 99 area percent as determined by gas chromatography (GC), into the ebullometer via a syringe pump capable of dividing 0.001 mL portions. The liquid was brought to a boil, and the equilibrium temperature of the ethanol or methanol at controlled atmospheric pressure was recorded. Next, (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, with a purity greater than 99.9 area percent as determined by gas chromatography (GC), was metered into the ebullometer in small increments via an automated syringe pump. After adding the required amount of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene to the ebullometer, the system was allowed to reach equilibrium for approximately 5 to 30 minutes, after which the equilibrium temperature of the condensing vapor-liquid mixture was recorded.

[0111] Composition versus boiling point data was obtained for a composition range of 0 to 100 weight percent of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and is shown in Tables 1 and 2 below, which show a temperature minimum indicating that an azeotrope was formed. These data are also shown in Figures 1 and 2.

[0112] Example 1: Ebriometer test with (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and methanol In the temperature vs. weight percent curve for (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (Figure 1), a minimum boiling point temperature was observed for 92.52 wt% (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and 7.48 wt% methanol, indicating a minimum boiling azeotrope. The observed temperature and composition data are shown in Table 1.

[0113] [Table 1]

[0114] Based on the above data, temperature glide and relative volatility were applied to determine azeotropic and azeotrope-like compositions.

[0115] Both the temperature glide and relative volatility of a mixture can be derived from thermodynamic measurements, such as those collected via an isobaric ebullionometer, subject to mass balance and thermodynamic constraints. Some methods for deriving temperature glide and relative volatility from thermodynamic measurements are described in Sandler, SI (2006) Chapter 10: Vapor-Liquid Equilibrium in Mixtures. In Chemical, Biochemical, and Engineering Thermodynamics (4 th ed., pp. 489-574), which involves constraining thermodynamic consistency with the fundamental Gibbs-Duhem relationship and resolving the gas-phase composition from measurements by a combination of mass balance and equilibrium criteria (called the Rachford-Rice equation or algorithm). This derivation establishes the relationship between equilibrium composition, temperature, and pressure, allowing the temperature glide and relative volatility to be estimated.

[0116] For a given composition, temperature glide is, by definition, the difference between the saturated vapor temperature and the saturated liquid temperature at a fixed pressure in thermodynamic equilibrium. Thus, an azeotropic composition has a temperature glide of zero, and an azeotrope-like composition has a temperature glide that is substantially close to zero. It has been determined that a temperature glide of less than 0.5°C is substantially close to zero, and therefore, compositions that meet such a temperature glide are considered azeotrope-like. This is a wide azeotrope-like range.

[0117] Relative volatility, by definition, is the ratio of the vapor composition to the liquid composition of the most volatile component compared to the vapor composition to the liquid composition of the less volatile component at a fixed pressure in thermodynamic equilibrium. Thus, an azeotropic composition has a relative volatility of 1.0, and an azeotrope-like composition has a relative volatility substantially close to 1.0. A relative volatility of 1.1 is substantially close to 1.0, and therefore, compositions meeting such a relative volatility have been identified as being azeotrope-like. This is the mid-azeotrope-like range.

[0118] It was further determined that a relative volatility of 1.05 is substantially close to 1.0, and therefore compositions meeting such a relative volatility are considered azeotrope-like. This is a narrow azeotrope-like range.

[0119] Based on the above, the azeotrope-like composition may comprise about 88% to 94% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, preferably about 90.0% to 92.2% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, or preferably about 90.6% to 91.7% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, and about 12% to 6% by weight of methanol, preferably about 10.0% to 7.8% by weight of methanol, or preferably about 9.4% to 8.3% by weight of methanol.

[0120] A true azeotrope is about 91.1 wt. % (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and 8.9 wt. % methanol, with a boiling point of about 49.66° C.±0.01° C. at a pressure of about 14.7 psia±0.2 psia.

[0121] In other words, the azeotropic or azeotrope-like composition consists essentially of, or consists of, about 88% to 94% by weight HCFO-1233yd(Z) and 12% to 6% by weight methanol, about 90.0% to 92.2% by weight HCFO-1233yd(Z) and 10.0% to 7.8% by weight methanol, about 90.6% to 91.7% by weight HCFO-1233yd(Z) and 9.4% to 8.3% by weight methanol, or about 91.1% by weight HCFO-1233yd(Z) and 8.9% by weight methanol.

[0122] Example 2: Ebriometer test with (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)) and ethanol In the temperature vs. weight percent curve for (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (Figure 2), a minimum boiling point temperature was observed for 96.02 wt% (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and 3.98 wt% ethanol, indicating a minimum boiling azeotrope. The observed temperature and composition data are shown in Table 2.

[0123] [Table 2]

[0124] Based on the above data, temperature glide and relative volatility were applied to determine azeotropic and azeotrope-like compositions.

[0125] Both the temperature glide and relative volatility of a mixture can be derived from thermodynamic measurements, such as those collected via an isobaric ebullionometer, subject to mass balance and thermodynamic constraints. Some methods for deriving temperature glide and relative volatility from thermodynamic measurements are described in Sandler, SI (2006) Chapter 10: Vapor-Liquid Equilibrium in Mixtures. In Chemical, Biochemical, and Engineering Thermodynamics (4 th ed., pp. 489-574), which involves constraining thermodynamic consistency with the fundamental Gibbs-Duhem relationship and resolving the gas-phase composition from measurements by a combination of mass balance and equilibrium criteria (called the Rachford-Rice equation or algorithm). This derivation establishes the relationship between equilibrium composition, temperature, and pressure, allowing the temperature glide and relative volatility to be estimated.

[0126] For a given composition, temperature glide is, by definition, the difference between the saturated vapor temperature and the saturated liquid temperature at a fixed pressure in thermodynamic equilibrium. Thus, an azeotropic composition has a temperature glide of zero, and an azeotrope-like composition has a temperature glide that is substantially close to zero. It has been determined that a temperature glide of less than 0.5°C is substantially close to zero, and therefore, compositions that meet such a temperature glide are considered azeotrope-like. This is a wide azeotrope-like range.

[0127] Relative volatility, by definition, is the ratio of the vapor composition to the liquid composition of the most volatile component compared to the vapor composition to the liquid composition of the less volatile component at a fixed pressure in thermodynamic equilibrium. Thus, an azeotropic composition has a relative volatility of 1.0, and an azeotrope-like composition has a relative volatility substantially close to 1.0. A relative volatility of 1.1 is substantially close to 1.0, and therefore, compositions meeting such a relative volatility have been identified as being azeotrope-like. This is the mid-azeotrope-like range.

[0128] It was further determined that a relative volatility of 1.05 is substantially close to 1.0, and therefore compositions meeting such a relative volatility are considered azeotrope-like. This is a narrow azeotrope-like range.

[0129] Based on the above, the azeotrope-like composition may comprise about 92.5% to 99.9% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, preferably about 94.8% to 97.5% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, or preferably about 95.3% to 96.4% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, and about 7.5% to 0.1% by weight of ethanol, preferably about 5.2% to 2.5% by weight of ethanol, or preferably about 4.7% to 3.6% by weight of ethanol.

[0130] A true azeotrope is about 95.9 wt. % (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and 4.1 wt. % ethanol, and has a boiling point of about 53.50° C.±0.01° C. at a pressure of about 14.7 psia±0.2 psia.

[0131] In other words, the azeotropic or azeotrope-like composition consists essentially of, or consists of, about 92.5% to 99.9% by weight HCFO-1233yd(Z) and 7.5% to 0.1% by weight ethanol, about 94.8% to 97.5% by weight HCFO-1233yd(Z) and 5.2% to 2.5% by weight ethanol, about 95.3% to 96.4% by weight HCFO-1233yd(Z) and 4.7% to 3.6% by weight ethanol, or about 95.9% by weight HCFO-1233yd(Z) and 4.1% by weight ethanol.

[0132] Ebriometer Test - Ternary Method For Examples 3 and 4 below, boiling point temperatures were measured using an isobaric ebullometer and its procedure described by the binary method, with the important difference being that the composition of the initial 50 mL of material added was not a single pure component. Initially, a binary mixture following a line of fixed composition ratio was identified, whereby the addition of a third component resulted in a global minimum temperature compared to the pure components and the binary azeotrope. Along this curve, boiling point temperatures were measured and a global minimum was observed. For example, an initial mixture of methanol and trans-dichloroethylene (trans-DCE) with compositions of 10.5 and 89.5 wt %, respectively, was added to the isobaric ebullometer, whereby the third component, i.e., (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd Z), was added stepwise until a minimum boiling temperature of 41.747°C was detected, as shown in Table 3 of Example 3. As a confirmation, the isobaric ebullionmeter was reinitialized with a separate binary component adjusted stepwise by the remaining third component, and both the overall composition and the global minimum temperature were obtained, which were consistent with the previous test. For example, a separate isobaric ebullionmeter was charged with the initial binary components ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)) and trans-dichloroethylene (trans-DCE) with compositions of 7.75 and 92.25 wt%, respectively, and the third component, namely methanol, was added stepwise until a minimum boiling temperature of 41.746 °C was detected, as shown in Table 4 of Example 3. It was verified that the same overall composition and minimum boiling temperature were observed along either fixed ratio curve.

[0133] Composition versus boiling point data for two lines of fixed binary composition ratios are shown in Tables 3 and 4 and Tables 6 and 7 below, showing the temperature minima that indicate the formation of a ternary azeotrope. These data are also shown graphically in Figures 3-6.

[0134] Example 3 - Ebuliometer Tests Using (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), Methanol, and Trans-Dichloroethylene (Trans-DCE) As shown in Table 3 and FIG. 3, when (Z)-1-chloro-2,3,3-trifluoroprop-1-ene was added to a mixture of methanol and trans-dichloroethylene maintained at a fixed mass ratio of 0.1173 in an isobaric ebullometer at 14.7 psia, a minimum boiling point temperature of 41.747° C. was observed for 7.05 wt % (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, 9.76 wt % methanol, and 83.19 wt % trans-dichloroethylene. Similarly, Table 4 and Figure 4 show that when methanol was added to a mixture of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and trans-dichloroethylene maintained at a fixed mass ratio of 0.0840 in an isobaric ebullometer at 14.7 psia, a minimum boiling point temperature of 41.746°C was observed for 6.98 wt% (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, 9.95 wt% methanol, and 83.08 wt% trans-dichloroethylene. The intersection of these curves was observed to form a global minimum temperature of 41.746°C ± 0.001°C, indicating the formation of a ternary azeotrope with a cross-average composition of 7.02 wt% (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, 9.85 wt% methanol, and 83.18 wt% trans-dichloroethylene. This global minimum temperature was confirmed when the boiling point temperature of the cross-composition was compared with the saturation temperatures of each of the pure and binary azeotropes found in the system, as summarized in Table 5.

[0135] [Table 3]

[0136] [Table 4]

[0137] [Table 5]

[0138] Example 4 - Ebuliometer Tests with HCFO-1233yd(Z), Ethanol, and trans-Dichloroethylene (trans-DCE) As shown in Table 6 and FIG. 5, when (Z)-1-chloro-2,3,3-trifluoroprop-1-ene was added to a mixture of ethanol and trans-dichloroethylene maintained at a fixed mass ratio of 0.0595 in an isobaric ebullometer at 14.7 psia, a minimum boiling point temperature of 45.558° C. was observed for 25.00 wt % (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, 4.21 wt % ethanol, and 70.79 wt % trans-dichloroethylene. Similarly, Table 7 and Figure 6 show that when ethanol was added to a mixture of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and trans-dichloroethylene maintained at a fixed mass ratio of 0.3538 in an isobaric ebullometer at 14.7 psia, a minimum boiling point temperature of 45.561°C was observed for 25.09 wt% (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, 4.00 wt% ethanol, and 70.91 wt% trans-dichloroethylene. The intersection of these curves was observed to form a global minimum temperature of 45.560°C ± 0.002°C, indicating the formation of a ternary azeotrope with a cross-average composition of 25.04 wt% (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, 4.11 wt% ethanol, and 70.85 wt% trans-dichloroethylene. This global minimum temperature was confirmed when the boiling point of the cross-composition was compared with the saturation temperatures of each of the pure and binary azeotropes found in the system, as summarized in Table 8.

[0139] [Table 6]

[0140] [Table 7]

[0141] [Table 8]

[0142] Example 5 Ternary azeotrope or azeotrope-like composition of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), methanol, and trans-dichloroethylene (trans-DCE) Considering the thermodynamic observations of the pure, binary, and ternary compositions described in Examples 1 and 3, ternary compositions of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), methanol, and trans-dichloroethylene (trans-DCE) were found to behave as azeotrope-like compositions. These compositions were found to boil at substantially constant temperatures and to provide vapor and liquid compositions that are substantially identical to one another, as described by considerations of relative volatility and temperature glide derived from thermodynamic measurements performed according to the methods and standards established in Example 1. Ternary azeotrope-like compositions of HCFO-1233yd(Z), methanol, and trans-DCE are found within the compositional region containing ternary azeotropes and are shown in the ternary diagram of FIG. 7A. These compositional regions can be described by points on the ternary diagram that correspond to the vertices of a quadrilateral enclosing the ternary azeotropic and azeotrope-like compositions of HCFO-1233yd(Z), methanol, and trans-DCE; the vertex labels for each compositional region are shown in Figure 7B, with the compositions summarized in Table 9.

[0143] [Table 9]

[0144] Example 6 Ternary azeotrope or azeotrope-like composition of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), ethanol, and trans-dichloroethylene (trans-DCE) Considering the thermodynamic observations of the pure, binary, and ternary compositions described in Examples 2 and 4, ternary compositions of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene (HCFO-1233yd(Z)), ethanol, and trans-dichloroethylene (trans-DCE) were found to behave as azeotrope-like compositions. These compositions were found to boil at substantially constant temperatures and to provide vapor and liquid compositions that are substantially identical to one another, as described by considerations of relative volatility and temperature glide derived from thermodynamic measurements provided by the methods and standards established in Example 2. Ternary azeotrope-like compositions of HCFO-1233yd(Z), ethanol, and trans-DCE are found within the compositional region containing ternary azeotropes and are shown in the ternary diagram of FIG. 8A. These compositional regions can be described by points on the ternary diagram that correspond to the vertices of a quadrilateral enclosing the ternary azeotropic and azeotrope-like compositions of HCFO-1233yd(Z), ethanol, and trans-DCE; the vertex labels for each compositional region are shown in Figure 8B, with the compositions summarized in Table 10.

[0145] [Table 10]

[0146] Example 7 Each of solvent compositions 1-4, including the present azeotrope or azeotrope-like compositions, is filled into an aerosol can. An aerosol valve is crimped into place on each can, and one of solvent compositions 1-4 is added through the valve to achieve an internal can pressure of approximately 20 PSIG. The compositions are then sprayed onto a surface to demonstrate their usefulness as aerosols.

[0147] Additionally, the aerosol composition can be sprayed onto surfaces containing oil, grease, dirt, or solder flux and is effective in solvating and removing such materials.

[0148] Example 8 Solvent compositions 1-4 containing the present azeotrope or azeotrope-like compositions are filled into an aerosol can. The aerosol valve is crimped in place, and one of solvent compositions 1-4 is added through the valve to achieve a pressure inside the can of approximately 20 PSIG. The composition is then sprayed onto a metal coupon contaminated with solder flux. The flux is removed, and the coupon is visually clean.

[0149] Example 9 Example 8 above is repeated, except that the cleaning composition is applied by immersion, vapor degreasing, or wiping instead of spraying. Optionally, the cleaning composition is applied undiluted. Optionally, the material being cleaned is changed from solder flux to mineral oil, silicone oil, or other lubricant. In each case, similar results are demonstrated.

[0150] Example 10 Solvent compositions 1-4 were prepared, along with several stainless steel coupons soiled with mineral oil. These coupons were then immersed in each of solvent compositions 1-4. Each of solvent compositions 1-4 removed the oil in a short period of time. The coupons were visually inspected and appeared clean.

[0151] Example 11 Aerosol solvents containing each of solvent compositions 1-4 were prepared. Kester 1544 Rosin Soldering Flux was placed on a stainless steel coupon and heated to approximately 300-400°F, simulating contact with a jet of solder typically used to solder electronic components in the manufacture of printed circuit boards. The coupon was then sprayed with the solvent and removed after 15 seconds without rinsing. Results indicated that the coupon appeared clean upon visual inspection.

[0152] Example 12 Each of solvent compositions 1-4 is used as a solvating agent for removing paints, coatings, and adhesives from surfaces. The solvating agent is effective in solvating paints, coatings, and adhesives, allowing for their removal from surfaces.

[0153] Example 13 Kester 1544 Rosin Soldering Flux was placed on a stainless steel coupon and heated to approximately 300-400°F to simulate contact with a jet of solder typically used to solder electronic components in the manufacture of printed circuit boards. The coupon was then cleaned with each of Solvent Compositions 1-4 by immersion degreasing or vapor degreasing. The results indicate that the coupons appeared clean upon visual inspection.

[0154] Aspects Embodiment 1 is a composition consisting essentially of about 88% to about 94% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and about 6% to about 12% by weight of methanol.

[0155] Example 2 is the composition of Example 1, consisting essentially of about 90% to 92.2% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and about 7.8% to about 10% by weight of methanol.

[0156] Aspect 3 is the composition of Aspect 1 or Aspect 2, consisting essentially of about 90.6% to about 91.7% by weight of (Z)-1-chloro-2,3,3-tetrafluoroprop-1-ene and about 8.3% to about 9.4% by weight of methanol.

[0157] Example 4 is the composition of any of Examples 1-3, consisting essentially of about 91.1% by weight (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and about 8.9% by weight methanol.

[0158] Aspect 5 is a composition consisting of about 88% to about 94% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and about 6% to about 12% by weight of methanol.

[0159] Aspect 6 is the composition of Aspect 5, consisting of about 90% to 92.2% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and about 7.8% to about 10% by weight of methanol.

[0160] Aspect 7 is the composition of Aspect 5 or Aspect 6, consisting of about 90.6% to about 91.7% by weight of (Z)-1-chloro-2,3,3-tetrafluoroprop-1-ene and about 8.3% to about 9.4% by weight of methanol.

[0161] Example 8 is the composition of any one of Examples 5 to 7, consisting of about 91.1% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and about 8.9% by weight of methanol.

[0162] Embodiment 9 is an azeotropic or azeotrope-like composition consisting essentially of about 88% to about 94% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and about 6% to about 12% by weight of methanol.

[0163] Example 10 is the composition of Example 9, which is an azeotropic or azeotrope-like composition consisting essentially of about 90% to 92.2% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and about 7.8% to about 10% by weight of methanol.

[0164] Example 11 is the composition of Example 9 or Example 10, wherein the composition is an azeotrope or azeotrope-like composition consisting essentially of about 90.6% to about 91.7% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and about 8.3% to about 9.4% by weight of methanol.

[0165] Example 12 is the composition of any of Examples 9-11, wherein the composition is an azeotropic or azeotrope-like composition consisting essentially of about 91.1% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and about 8.9% by weight of methanol.

[0166] Embodiment 13 is an azeotropic or azeotrope-like composition consisting of about 88% to about 94% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and about 6% to about 12% by weight of methanol.

[0167] Example 14 is the composition of Example 13, which is an azeotropic or azeotrope-like composition consisting of about 90% to 92.2% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and about 7.8% to about 10% by weight of methanol.

[0168] Example 15 is the composition of Example 13 or Example 14, wherein the composition is an azeotrope or azeotrope-like composition consisting of about 90.6% to 91.7% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and about 8.3% to about 9.4% by weight of methanol.

[0169] Example 16 is the composition of any of Examples 5-7, which is an azeotropic or azeotrope-like composition consisting of about 91.1% by weight (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and about 8.9% by weight methanol.

[0170] Example 17 is the composition of any of Examples 9-16, wherein the azeotropic or azeotrope-like composition has a boiling point of about 49.66° C.±0.001° C. at a pressure of about 14.7 psia±0.2 psia.

[0171] Aspect 18 is a composition consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene, wherein in a ternary composition diagram, (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene are arranged at the following points as vertices: Point A: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 0.9% by weight / approximately 8.2% by weight / approximately 90.9% by weight), Point B: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 0.9% by weight / approximately 13.7% by weight / approximately 85.4% by weight), Point C: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 39.6% by weight / approximately 8.3% by weight / approximately 52.1% by weight), Point D: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 41.1% by weight / about 4.9% by weight / about 54.0% by weight).

[0172] Aspect 19 is the composition of aspect 18, consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene, wherein the (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene are aligned at the following vertices: Point E: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 3.9% by weight / approximately 8.7% by weight / approximately 87.4% by weight), Point F: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 3.8% by weight / approximately 11.8% by weight / approximately 84.4% by weight), Point G: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 27.4% by weight / approximately 8.9% by weight / approximately 63.7% by weight), Point H: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 28.1% by weight / about 6.5% by weight / about 65.4% by weight).

[0173] Embodiment 20 is a compound of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene, the compound consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene, the compound having the following vertices: Point I: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 6.7% by weight / approximately 9.2% by weight / approximately 84.1% by weight), Point J: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 6.7% by weight / approximately 10.0% by weight / approximately 83.3% by weight), Point K: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 7.4% by weight / approximately 9.9% by weight / approximately 82.7% by weight), Point L: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 7.5% by weight / about 9.2% by weight / about 83.3% by weight).

[0174] Example 21 is the composition of any of Examples 18-20, consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene present in amounts of about 7.02 wt%, about 9.85 wt%, and about 83.13 wt%, respectively.

[0175] Aspect 22 is a composition consisting of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene, and in a ternary composition diagram, (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene are arranged at the following points as vertices: Point A: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 0.9% by weight / approximately 8.2% by weight / approximately 90.9% by weight), Point B: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 0.9% by weight / approximately 13.7% by weight / approximately 85.4% by weight), Point C: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 39.6% by weight / approximately 8.3% by weight / approximately 52.1% by weight), Point D: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 41.1% by weight / about 4.9% by weight / about 54.0% by weight).

[0176] Aspect 23 consists of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene, wherein the (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene are arranged at the following points as vertices: Point E: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 3.9% by weight / approximately 8.7% by weight / approximately 87.4% by weight), Point F: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 3.8% by weight / approximately 11.8% by weight / approximately 84.4% by weight), Point G: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 27.4% by weight / approximately 8.9% by weight / approximately 63.7% by weight), Point H: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 28.1% by weight / about 6.5% by weight / about 65.4% by weight).

[0177] Aspect 24 consists of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene, wherein the (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene are arranged at the following points as vertices: Point I: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 6.7% by weight / approximately 9.2% by weight / approximately 84.1% by weight), Point J: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 6.7% by weight / approximately 10.0% by weight / approximately 83.3% by weight), Point K: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 7.4% by weight / approximately 9.9% by weight / approximately 82.7% by weight), Point L: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 7.5% by weight / about 9.2% by weight / about 83.3% by weight).

[0178] Example 25 is a composition according to any of Examples 22-24, consisting of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene present in amounts of about 7.02 wt%, about 9.85 wt%, and about 83.13 wt%, respectively.

[0179] Aspect 26 is an azeotrope of an azeotrope-like composition consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene, in which in a ternary diagram, (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene form the following points as vertices: Point A: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 0.9% by weight / approximately 8.2% by weight / approximately 90.9% by weight), Point B: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 0.9% by weight / approximately 13.7% by weight / approximately 85.4% by weight), Point C: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 39.6% by weight / approximately 8.3% by weight / approximately 52.1% by weight), Point D: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 41.1% by weight / about 4.9% by weight / about 54.0% by weight).

[0180] Aspect 27 consists essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene, wherein the (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene are positioned at the following vertices: Point E: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 3.9% by weight / approximately 8.7% by weight / approximately 87.4% by weight), Point F: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 3.8% by weight / approximately 11.8% by weight / approximately 84.4% by weight), Point G: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 27.4% by weight / approximately 8.9% by weight / approximately 63.7% by weight), Point H: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 28.1 wt % / about 6.5 wt % / about 65.4 wt %). An azeotrope of the azeotrope-like composition described in embodiment 26 is within a rectangular region having the formula:

[0181] Embodiment 28 consists essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene, wherein the (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene are positioned at the following vertices: Point I: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 6.7% by weight / approximately 9.2% by weight / approximately 84.1% by weight), Point J: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 6.7% by weight / approximately 10.0% by weight / approximately 83.3% by weight), Point K: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 7.4% by weight / approximately 9.9% by weight / approximately 82.7% by weight), Point L: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 7.5% by weight / about 9.2% by weight / about 83.3% by weight), and an azeotrope of the azeotrope-like composition of embodiment 26 or embodiment 27, which is within a quadrilateral region having the formula:

[0182] Example 29 is an azeotrope of an azeotrope-like composition of any of Examples 26-28, wherein (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene are present in amounts of about 7.02 wt%, about 9.85 wt%, and about 83.13 wt%, respectively.

[0183] Aspect 30 is an azeotrope of an azeotrope-like composition consisting of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene, in which in a ternary composition diagram, (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene form the following points as vertices: Point A: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 0.9% by weight / approximately 8.2% by weight / approximately 90.9% by weight), Point B: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 0.9% by weight / approximately 13.7% by weight / approximately 85.4% by weight), Point C: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 39.6% by weight / approximately 8.3% by weight / approximately 52.1% by weight), Point D: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 41.1% by weight / about 4.9% by weight / about 54.0% by weight), which is an azeotrope-like mixture within the quadrilateral region having the formula:

[0184] Aspect 31 consists of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene, wherein the (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene are arranged at the following points as vertices: Point E: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 3.9% by weight / approximately 8.7% by weight / approximately 87.4% by weight), Point F: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 3.8% by weight / approximately 11.8% by weight / approximately 84.4% by weight), Point G: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 27.4% by weight / approximately 8.9% by weight / approximately 63.7% by weight), Point H: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 28.1 wt % / about 6.5 wt % / about 65.4 wt %). An azeotrope of the azeotrope-like composition described in embodiment 30 is within a rectangular region having the formula:

[0185] Aspect 32 consists of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene, wherein the (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene are arranged at the following points as vertices: Point I: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 6.7% by weight / approximately 9.2% by weight / approximately 84.1% by weight), Point J: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 6.7% by weight / approximately 10.0% by weight / approximately 83.3% by weight), Point K: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=approximately 7.4% by weight / approximately 9.9% by weight / approximately 82.7% by weight), Point L: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 7.5% by weight / about 9.2% by weight / about 83.3% by weight), and an azeotrope of the azeotrope-like composition of embodiment 30 or embodiment 31, which is within a rectangular region having the following formula:

[0186] Example 33 is an azeotrope of an azeotrope-like composition according to any of Examples 30-32, consisting of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene in amounts of about 7.02%, about 9.85%, and about 83.13% by weight, respectively.

[0187] Example 34 is an azeotrope of the azeotrope-like composition of any of Examples 26-33, wherein the azeotrope or azeotrope-like composition has a boiling point of about 41.746°C ± 0.001°C at a pressure of about 14.7 psia ± 0.2 psia.

[0188] Aspect 35 is a composition consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene, wherein in a ternary composition diagram, (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene are arranged at the following points as vertices: Point M: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 1.0% by weight / about 1.0% by weight / about 98.0% by weight), Point N: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=approximately 0.9% by weight / approximately 9.0% by weight / approximately 90.1% by weight), Point O: (Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=approximately 33.3% by weight / approximately 6.1% by weight / approximately 60.6% by weight; Point P: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 35.5% by weight / about 0.6% by weight / about 64.1% by weight).

[0189] Embodiment 36 is a compound consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene, wherein the (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene are arranged at the following vertices: Point Q: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=approximately 13.4% by weight / approximately 2.5% by weight / approximately 84.1% by weight), Point R: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 12.9% by weight / about 6.5% by weight / about 80.6% by weight), Point S: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=approximately 31.6% by weight / approximately 5.1% by weight / approximately 63.3% by weight), Point T: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 32.7% by weight / about 2.0% by weight / about 65.3% by weight).

[0190] Aspect 37 consists essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene, wherein the (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene are arranged at the following vertices: Point U: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=approximately 22.2% by weight / approximately 3.7% by weight / approximately 74.1% by weight), Point V: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 22.1% by weight / about 4.4% by weight / about 73.5% by weight), Point W: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=approximately 27.4% by weight / approximately 4.1% by weight / approximately 68.5% by weight), Point X: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 27.6% by weight / about 3.4% by weight / about 69.0% by weight).

[0191] Example 38 is the composition of any of Examples 35-37, consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene present in amounts of about 25.04 wt%, about 4.11 wt%, and about 70.85 wt%, respectively.

[0192] Aspect 39 is a composition consisting of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene, in which in a ternary composition diagram, (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene are arranged at the following points as vertices: Point M: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 1.0% by weight / about 1.0% by weight / about 98.0% by weight), Point N: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=approximately 0.9% by weight / approximately 9.0% by weight / approximately 90.1% by weight), Point O: (Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=approximately 33.3% by weight / approximately 6.1% by weight / approximately 60.6% by weight; Point P: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 35.5% by weight / about 0.6% by weight / about 64.1% by weight).

[0193] Embodiment 40 consists of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene, wherein the (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene are arranged at the following points as vertices: Point Q: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=approximately 13.4% by weight / approximately 2.5% by weight / approximately 84.1% by weight), Point R: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 12.9% by weight / about 6.5% by weight / about 80.6% by weight), Point S: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=approximately 31.6% by weight / approximately 5.1% by weight / approximately 63.3% by weight), Point T: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 32.7% by weight / about 2.0% by weight / about 65.3% by weight).

[0194] Aspect 41 consists of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene, wherein (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene are arranged at the following points as vertices: Point U: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=approximately 22.2% by weight / approximately 3.7% by weight / approximately 74.1% by weight), Point V: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 22.1% by weight / about 4.4% by weight / about 73.5% by weight), Point W: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=approximately 27.4% by weight / approximately 4.1% by weight / approximately 68.5% by weight), Point X: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 27.6% by weight / about 3.4% by weight / about 69.0% by weight).

[0195] Example 42 is a composition of any of Examples 39-41, consisting of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene present in amounts of about 25.04 wt%, about 4.11 wt%, and about 70.85 wt%, respectively.

[0196] Aspect 43 is an azeotropic or azeotrope-like composition consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene, wherein the (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene form a ternary diagram with the following points as vertices: Point M: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 1.0% by weight / about 1.0% by weight / about 98.0% by weight), Point N: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=approximately 0.9% by weight / approximately 9.0% by weight / approximately 90.1% by weight), Point O: (Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=approximately 33.3% by weight / approximately 6.1% by weight / approximately 60.6% by weight; Point P: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 35.5% by weight / about 0.6% by weight / about 64.1% by weight), which is an azeotropic or azeotrope-like composition within the quadrilateral region having the formula:

[0197] Embodiment 44 is an azeotropic or azeotrope-like composition consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene, wherein the (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene are spaced apart by the following points as vertices: Point Q: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=approximately 13.4% by weight / approximately 2.5% by weight / approximately 84.1% by weight), Point R: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 12.9% by weight / about 6.5% by weight / about 80.6% by weight), Point S: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=approximately 31.6% by weight / approximately 5.1% by weight / approximately 63.3% by weight), Point T: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 32.7% by weight / about 2.0% by weight / about 65.3% by weight).

[0198] Embodiment 45 is an azeotropic or azeotrope-like composition consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene, wherein the (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene are spaced apart by the following points as vertices: Point U: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=approximately 22.2% by weight / approximately 3.7% by weight / approximately 74.1% by weight), Point V: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 22.1% by weight / about 4.4% by weight / about 73.5% by weight), Point W: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=approximately 27.4% by weight / approximately 4.1% by weight / approximately 68.5% by weight), Point X: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 27.6% by weight / about 3.4% by weight / about 69.0% by weight).

[0199] Example 46 is the composition of any of Examples 43-45, which is an azeotropic or azeotrope-like composition consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene present in amounts of about 25.04 wt %, about 4.11 wt %, and about 70.85 wt %, respectively.

[0200] Aspect 47 is an azeotropic or azeotrope-like composition consisting of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene, in which in a ternary composition diagram, (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene are arranged at the following points as vertices: Point M: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 1.0% by weight / about 1.0% by weight / about 98.0% by weight), Point N: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=approximately 0.9% by weight / approximately 9.0% by weight / approximately 90.1% by weight), Point O: (Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=approximately 33.3% by weight / approximately 6.1% by weight / approximately 60.6% by weight; Point P: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 35.5% by weight / about 0.6% by weight / about 64.1% by weight), which is an azeotropic or azeotrope-like composition within the quadrilateral region having the formula:

[0201] Aspect 48 is an azeotropic or azeotrope-like composition consisting of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene, wherein the (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene are arranged at the following vertices: Point Q: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=approximately 13.4% by weight / approximately 2.5% by weight / approximately 84.1% by weight), Point R: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 12.9% by weight / about 6.5% by weight / about 80.6% by weight), Point S: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=approximately 31.6% by weight / approximately 5.1% by weight / approximately 63.3% by weight), Point T: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 32.7% by weight / about 2.0% by weight / about 65.3% by weight).

[0202] Aspect 49 consists of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene, wherein the (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene are arranged at the following points as vertices: Point U: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=approximately 22.2% by weight / approximately 3.7% by weight / approximately 74.1% by weight), Point V: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 22.1% by weight / about 4.4% by weight / about 73.5% by weight), Point W: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=approximately 27.4% by weight / approximately 4.1% by weight / approximately 68.5% by weight), Point X: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 27.6% by weight / about 3.4% by weight / about 69.0% by weight).

[0203] Example 50 is a composition of any of Examples 47-49, consisting of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene present in amounts of about 25.04 wt%, about 4.11 wt%, and about 70.85 wt%, respectively.

[0204] Example 51 is the composition of any of Examples 43-50, wherein the azeotropic or azeotrope-like composition has a boiling point of about 41.746° C.±0.001° C. at a pressure of about 14.7 psia±0.2 psia.

[0205] A fifty-second embodiment is a solvent composition comprising the composition according to any one of the first to fifty-first embodiments.

[0206] Aspect 53 is the use of the composition according to any one of Aspects 1 to 52 as a solvent.

[0207] Embodiment 54 is a method for cleaning a substrate comprising contacting the substrate with the composition of any of embodiments 1-52.

[0208] Example 55 is the method of example 54, wherein contacting the substrate comprises contacting the composition with oil, grease, dirt, mineral oil, silicone oil, fluorosilicone oil, fingerprints, or a lubricant.

[0209] Example 56 is the method of example 54, wherein contacting the substrate comprises contacting the composition with a solder flux.

[0210] Aspect 57 is vaporizing the composition of any one of embodiments 1-52; A method for vapor degreasing, comprising contacting a vaporized solvent composition with a surface containing oil, grease, dirt, mineral oil, silicone oil, or lubricant.

[0211] Aspect 58 is: A method for cleaning, comprising dispensing a composition according to any one of embodiments 1 to 52 from a container onto a surface in aerosol form.

[0212] Aspect 59 is A method for liquid solvation, comprising contacting a composition according to any one of embodiments 1-52 with a surface, including a paint, coating, or adhesive.

[0213] Embodiment 60 is a composition including any of embodiments 1-52.

[0214] It should be understood that the foregoing description is merely illustrative of the present disclosure. Various alternatives and modifications may be devised by those skilled in the art without departing from the present disclosure. Accordingly, the present disclosure is intended to embrace all such alternatives, modifications, and variations that fall within the scope of the appended claims.

Claims

1. A composition comprising an azeotropic or azeotrope-like composition consisting essentially of an effective amount of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and methanol.

2. 2. The composition of claim 1, wherein the azeotropic or azeotrope-like composition consists essentially of from about 88% to about 94% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and from about 6% to about 12% by weight of methanol.

3. 2. The composition of claim 1, wherein the azeotropic or azeotrope-like composition consists essentially of from about 90% to about 92.2% by weight of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and from about 7.8% to about 10% by weight of methanol.

4. 4. The composition of any one of claims 1 to 3, wherein the azeotropic or azeotrope-like composition has a boiling point of about 49.66°C ± 0.01°C at a pressure of about 14.7 psia ± 0.2 psia.

5. 1. A composition comprising an azeotropic or azeotrope-like composition consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene; In the ternary composition diagram, the (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene are arranged at the following points as vertices: Point A: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 0.9% by weight / about 8.2% by weight / about 90.9% by weight), Point B: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 0.9% by weight / about 13.7% by weight / about 85.4% by weight), Point C: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 39.6% by weight / about 8.3% by weight / about 52.1% by weight), Point D: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 41.1% by weight / about 4.9% by weight / about 54.0% by weight).

6. The (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene have the following points as vertices: Point E: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 3.9% by weight / about 8.7% by weight / about 87.4% by weight), Point F: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 3.8% by weight / about 11.8% by weight / about 84.4% by weight), Point G: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 27.4% by weight / about 8.9% by weight / about 63.7% by weight), Point H: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 28.1% by weight / about 6.5% by weight / about 65.4% by weight).

7. The (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene have the following points as vertices: Point I: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 6.7% by weight / about 9.2% by weight / about 84.1% by weight), Point J: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 6.7% by weight / about 10.0% by weight / about 83.3% by weight), Point K: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 7.4% by weight / about 9.9% by weight / about 82.7% by weight), 7. The composition according to claim 6, wherein point L is within a quadrilateral region having ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 7.5% by weight / about 9.2% by weight / about 83.3% by weight).

8. 8. The composition of any one of claims 5 to 7, wherein the azeotropic or azeotrope-like composition has a boiling point of about 41.746°C ± 0.001°C at a pressure of about 14.7 psia ± 0.2 psia.

9. 1. A composition comprising an azeotropic or azeotrope-like composition consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene; In the ternary composition diagram, the (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene are positioned at the following points as vertices: Point M: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 1.0% by weight / about 1.0% by weight / about 98.0% by weight), Point N: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 0.9% by weight / about 9.0% by weight / about 90.1% by weight), Point O: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 33.3% by weight / about 6.1% by weight / about 60.6% by weight), Point P: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 35.5% by weight / about 0.6% by weight / about 64.1% by weight).

10. The (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene have the following points as vertices: Point Q: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 13.4% by weight / about 2.5% by weight / about 84.1% by weight), Point R: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 12.9% by weight / about 6.5% by weight / about 80.6% by weight), Point S: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 31.6% by weight / about 5.1% by weight / about 63.3% by weight), 10. The composition according to claim 9, wherein the point T is within a quadrilateral region having ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 32.7% by weight / about 2.0% by weight / about 65.3% by weight).

11. The (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene have the following points as vertices: Point U: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 22.2% by weight / about 3.7% by weight / about 74.1% by weight), Point V: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 22.1% by weight / about 4.4% by weight / about 73.5% by weight), Point W: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 27.4% by weight / about 4.1% by weight / about 68.5% by weight), 10. The composition according to claim 9, wherein point X is within a quadrilateral region having ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / ethanol / trans-dichloroethylene=about 27.6% by weight / about 3.4% by weight / about 69.0% by weight).

12. 12. The composition of any one of claims 9 to 11, wherein the azeotropic or azeotrope-like composition has a boiling point of about 41.746°C ± 0.001°C at a pressure of about 14.7 psia ± 0.2 psia.

13. a composition comprising an effective amount of an azeotropic or azeotrope-like composition consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and methanol; an azeotrope or azeotrope-like composition consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene; and an azeotrope or azeotrope-like composition consisting essentially of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene.

14. 14. The solvent composition of claim 13 consisting essentially of an azeotropic or azeotrope-like composition consisting essentially of effective amounts of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene and methanol.

15. The composition essentially consists of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene, and in a ternary composition diagram, the (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, methanol, and trans-dichloroethylene are located at the following points as vertices: Point A: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 0.9% by weight / about 8.2% by weight / about 90.9% by weight), Point B: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 0.9% by weight / about 13.7% by weight / about 85.4% by weight), Point C: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 39.6% by weight / about 8.3% by weight / about 52.1% by weight), Point D: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 41.1% by weight / about 4.9% by weight / about 54.0% by weight).

16. The composition essentially consists of (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene, and in a ternary composition diagram, the (Z)-1-chloro-2,3,3-trifluoroprop-1-ene, ethanol, and trans-dichloroethylene are located at the following points as vertices: Point E: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 3.9% by weight / about 8.7% by weight / about 87.4% by weight), Point F: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 3.8% by weight / about 11.8% by weight / about 84.4% by weight), Point G: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 27.4% by weight / about 8.9% by weight / about 63.7% by weight), Point H: ((Z)-1-chloro-2,3,3-trifluoroprop-1-ene / methanol / trans-dichloroethylene=about 28.1% by weight / about 6.5% by weight / about 65.4% by weight).

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