Azeotrope or azeotrope-like composition of trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl)

Abstract

The present disclosure provides an azeotrope or azeotrope-like composition comprising trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl), and a method of forming an azeotrope or azeotrope-like composition, the method comprising the step of combining trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) to form an azeotrope or azeotrope-like composition.

Description

Technical Field

[0001] The present disclosure relates to azeotropes or azeotrope-like compositions, and in particular to azeotropes or azeotrope-like compositions comprising trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl). Background Art

[0002] Fluorocarbon-based fluids have been used extensively in industry for many applications, including as refrigerants, aerosol propellants, foam blowing agents, heat transfer media, gaseous dielectrics, and fire extinguishing.

[0003] However, it is suspected that some compounds such as chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs) deplete atmospheric ozone, and are therefore harmful to the environment. In addition, it is believed that some of these compounds contribute to global warming. Therefore, it is desirable to use fluorocarbon fluids with low ozone depletion potential or even zero ozone depletion potential, such as hydrofluorocarbons (HFCs) or those with photodegradable carbon-iodine bonds, which exhibit short atmospheric lifetimes when released at ground level. It is also desirable to use single-component fluids or azeotropic mixtures that do not fractionate when boiling and evaporating.

[0004] Unfortunately, identification of new environmentally safe nonfractionating mixtures is complicated by the difficulty in predicting azeotrope formation.

[0005] Industry is continually seeking new fluorocarbon-based mixtures that offer alternatives and are considered environmentally safer replacements for the CFCs, HCFCs, and HFCs used today. Of particular interest are iodine-containing compounds and other fluorinated compounds that have low ozone depletion potential and low global warming potential. Such mixtures are the subject of the present disclosure.

[0006] Although iodine-containing compounds are of the greatest potential interest, the purification of iodine-containing compounds such as trifluoroiodomethane (CF3I) presents a challenge, and there is a need for techniques for removing impurities such as, for example, trifluoromethane (HFC-23) from trifluoroiodomethane (CF3I). Therefore, separation techniques such as, for example, azeotropic distillation would be highly desirable.

[0007] There is a need for compositions and techniques that can be used to prepare high purity iodine-containing compounds such as trifluoroiodomethane (CF3I). Summary of the invention

[0008] The present disclosure provides azeotrope or azeotrope-like compositions of trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl).

[0009] It is recognized in the art that it is impossible to predict the formation of azeotropes, and the present inventors have unexpectedly discovered that trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl) form an azeotrope or azeotrope-like composition.

[0010] The present disclosure provides a composition comprising an azeotrope or azeotrope-like composition, the azeotrope or azeotrope-like composition consisting essentially of or consisting of effective amounts of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I). The azeotrope or azeotrope-like composition has a boiling point between about -46.0°C and about 90.0°C at a pressure between about 4.9 psia and about 348 psia, and consists essentially of or consisting of about 0.5 wt % to about 99.0 wt % of trifluoroacetyl chloride (CF3COCl) and about 1.0 wt % to about 99.5 wt % of trifluoroiodomethane (CF3I).

[0011] The azeotrope or azeotrope-like composition may consist essentially of or consist of about 0.5 wt % to about 25 wt % trifluoroacetyl chloride (CF3COCl), about 2 wt % to about 21 wt % trifluoroacetyl chloride (CF3COCl), about 14 wt % to about 18 wt % trifluoroacetyl chloride (CF3COCl), and in an azeotrope, about 14.87 wt % trifluoroacetyl chloride (CF3COCl), and about 75 wt % to about 99.5 wt % trifluoroiodomethane (CF3I), about 79 wt % to about 98 wt % trifluoroiodomethane (CF3I), about 82 wt % to about 86 wt % trifluoroiodomethane (CF3I), and in an azeotrope, about 85.13 wt % trifluoroiodomethane (CF3I). The azeotrope or azeotrope-like composition has a boiling point of about -22.50°C ± 0.30°C at a pressure of about 14.41 psia ± 0.30 psia.

[0012] In other words, the azeotrope or azeotrope-like composition may consist essentially of or consist of about 0.5 wt % to about 25 wt % trifluoroacetyl chloride (CF3COCl) and about 75 wt % to about 99.5 wt % trifluoroiodomethane (CF3I), about 2 wt % to about 21 wt % trifluoroacetyl chloride (CF3COCl) and about 79 wt % to about 98 wt % trifluoroiodomethane (CF3I), or about 14 wt % to about 18 wt % trifluoroacetyl chloride (CF3COCl) and about 82 wt % to about 86 wt % trifluoroiodomethane (CF3I), and in one azeotrope, about 14.87 wt % trifluoroacetyl chloride (CF3COCl) and about 85.13 wt % trifluoroiodomethane (CF3I). The azeotrope or azeotrope-like composition has a boiling point of about -22.50°C ± 0.30°C at a pressure of about 14.41 psia ± 0.30 psia.

[0013] The present disclosure also provides an azeotrope or azeotrope-like composition consisting essentially of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) and having a boiling point of about -22.50°C ± 0.30°C at a pressure of about 14.41 psia ± 0.30 psia.

[0014] The present disclosure also provides a method of forming an azeotrope or azeotrope-like composition, the method comprising the step of combining trifluoroacetyl chloride (CF3COCl) with trifluoroiodomethane (CF3I) to form an azeotrope or azeotrope-like composition, the azeotrope or azeotrope-like composition consisting essentially of or consisting of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I), and having a boiling point between about -46.0°C and about 90.0°C at a pressure between about 4.9 psia and about 348 psia. The combining step may include mixing about 0.5 wt % to about 99.0 wt % of trifluoroacetyl chloride (CF3COCl) and about 1.0 wt % to about 99.5 wt % of trifluoroiodomethane (CF3I).

[0015] The present disclosure also provides a method of forming an azeotrope or azeotrope-like composition, the method comprising the step of combining trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) to form an azeotrope or azeotrope-like composition, the azeotrope or azeotrope-like composition consisting essentially of or consisting of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I). The azeotrope or azeotrope-like composition may have a boiling point of about -22.50°C ± 0.30°C at a pressure of about 14.41 psia ± 0.30 psia.

[0016] The present disclosure also provides a method for separating trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) from a primary composition comprising trifluoroacetyl chloride (CF3COCl), trifluoroiodomethane (CF3I) and at least one impurity, the method comprising the following steps: forming a secondary composition in the primary composition, the secondary composition being an azeotrope or azeotrope-like composition consisting essentially of effective amounts of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I); and separating the secondary composition from the primary composition and at least one impurity. The forming step comprises forming a secondary composition in the primary composition, the secondary composition being an azeotrope or azeotrope-like composition consisting essentially of about 0.5 wt % to about 99.0 wt % of trifluoroacetyl chloride (CF3COCl) and about 1.0 wt % to about 99.0 wt % of trifluoroiodomethane (CF3I) and having a boiling point between about -46.0°C and about 90.0°C at a pressure between about 4.9 psia and about 348 psia.

[0017] The present disclosure also provides a method for separating trifluoroacetyl chloride (CF3COCl) or trifluoroiodomethane (CF3I) from at least one impurity, the method comprising the steps of: providing a composition comprising one of trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl) and at least one impurity; adding a sufficient amount of the other of trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl); and subjecting the composition to conditions effective to form a composition that is an azeotrope or azeotrope-like composition consisting essentially of or consisting of effective amounts of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I); and separating the azeotrope or azeotrope-like composition from the impurity by a separation technique such as phase separation, distillation, or fractionation. Conditions effective to form an azeotrope or azeotrope-like composition may include providing about 0.5 wt % to about 99.0 wt % trifluoroacetyl chloride (CF3COCl) and about 1.0 wt % to about 99.0 wt % trifluoroiodomethane (CF3I), and having a boiling point between about -46.0°C and about 90.0°C at a pressure between about 4.9 psia and about 348 psia.

[0018] The present disclosure also provides a method for separating trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) from a primary composition comprising trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I), the method comprising the steps of: conveying a feed stream comprising the primary composition to a low-pressure column; collecting a first bottom product from the low-pressure column, the first bottom product consisting essentially of trifluoroacetyl chloride (CF3COCl); conveying a first distillate from the low-pressure column to a high-pressure column, the first distillate comprising an azeotrope or azeotrope-like composition consisting essentially of an effective amount of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I); and collecting a second bottom product from the high-pressure column, the second bottom product consisting essentially of trifluoroiodomethane (CF3I). The method may also include, after the second collecting step, an additional step of recycling the second distillate from the high-pressure column back to the feed stream comprising the primary composition.

[0019] The present disclosure also provides a method for separating trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) from a primary composition comprising trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I), the method comprising the following steps: conveying a feed stream comprising the primary composition to a high-pressure column; collecting a first bottom product from the high-pressure column, the first bottom product consisting essentially of trifluoroiodomethane (CF3I); conveying a first distillate from the high-pressure column to a low-pressure column, the first distillate comprising an azeotrope or azeotrope-like composition consisting essentially of an effective amount of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I); collecting a second bottom product from the low-pressure column, the second bottom product consisting essentially of trifluoroacetyl chloride (CF3COCl). The method may also include an additional step of recycling the second distillate from the low-pressure column back to the feed stream comprising the primary composition after the second collecting step. BRIEF DESCRIPTION OF THE DRAWINGS

[0020] Figure 1 It is a graph of temperature versus weight percentage of trifluoroiodomethane (CF3I) measured according to Example 1.

[0021] Figure 2 Corresponding to Example 3, it is a graph of temperature versus composition (mass fraction of trifluoroiodomethane (CF-3I)), wherein the two curves are placed at arbitrary low pressure and arbitrary high pressure, respectively.

[0022] Figure 3 An exemplary pressure swing distillation configuration is shown. DETAILED DESCRIPTION

[0023] It has been found that trifluoroacetyl chloride (CF3COCl) forms a homogeneous, minimum boiling azeotrope and azeotrope-like composition or mixture with trifluoroiodomethane (CF3I), and the present disclosure provides a homogeneous azeotrope or azeotrope-like composition comprising trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I). The azeotrope or azeotrope-like composition may consist essentially of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I), or the azeotrope or azeotrope-like composition may consist of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I).

[0024] The present inventors have experimentally discovered that trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) form an azeotrope or azeotrope-like composition.

[0025] An "azeotrope" composition is a unique combination of two or more components. Azeotrope compositions can be characterized in various ways. For example, at a given pressure, an azeotrope composition boils at a constant characteristic temperature that is either higher than the higher boiling component (maximum boiling azeotrope) or lower than the lower boiling component (minimum boiling azeotrope). At this characteristic temperature, the same composition will exist in both the gas phase and the liquid phase. Azeotrope compositions do not fractionate when boiling or evaporating. Therefore, the components of an azeotrope composition cannot be separated during a phase change.

[0026] Azeotrope compositions are also characterized in that, at the characteristic azeotrope temperature, the bubble point pressure of the liquid phase is the same as the dew point pressure of the vapor phase.

[0027] The behavior of azeotropic compositions is in contrast to the behavior of zeotropic compositions, in which the liquid composition changes to a considerable extent during boiling or evaporation.

[0028] For purposes of this disclosure, an azeotrope composition is characterized in that it boils at a constant characteristic temperature that is below the boiling points of two or more components (the minimum boiling azeotrope) and thus has the same composition in both the vapor and liquid phases.

[0029] However, it will be appreciated by those of ordinary skill in the art that the composition and boiling point of an azeotrope composition will vary to some extent at different pressures. Thus, depending on the temperature and / or pressure, an azeotrope composition may have a varying composition. Thus, it will be appreciated by those of ordinary skill in the art that a range of compositions rather than fixed compositions may be used to define an azeotrope composition. Additionally, an azeotrope may be defined based on the exact weight percentage of each component of a composition characterized by a fixed boiling point at a specified pressure.

[0030] An "azeotrope-like" composition is a composition of two or more components that behaves essentially like an azeotrope composition. Thus, for purposes of this disclosure, an azeotrope-like composition is a combination of two or more different components that, when in liquid form at a given pressure, will boil at a substantially constant temperature and which will provide a vapor composition that is substantially the same as the liquid composition undergoing boiling.

[0031] For purposes of this disclosure, an azeotrope-like composition is a composition or range of compositions that boils at a temperature range between about -46.0°C and about 90.0°C at a pressure between about 4.9 psia and about 348 psia, including, for example, a composition or range of compositions that boils at a temperature range of about -22.50°C ± 0.30°C at a pressure of about 14.41 psia ± 0.30 psia.

[0032] Azeotropes or azeotrope-like compositions can be identified in a number of different ways.

[0033] For the purposes of this disclosure, azeotropes or azeotrope-like compositions are identified experimentally using an ebulliometer (Walas, Phase Equilibria in Chemical Engineering, Butterworth-Heinemann, 1985, 533-544). An ebulliometer is designed to measure the boiling point of a liquid very accurately by measuring the temperature of vapor-liquid equilibrium.

[0034] The boiling points of each component alone are measured at a constant pressure. The skilled person will know that for a binary azeotrope or azeotrope-like composition, the boiling point of one of the components of the composition is initially measured. The second component of the composition is then added in varying amounts, and the boiling points of each of the resulting compositions are measured at said constant pressure using an ebulliometer.

[0035] The measured boiling points are plotted against the composition of the composition tested, e.g., for a binary azeotrope, the amount of the second component added to the composition (expressed in weight % or mole %). The presence of an azeotrope composition can be identified by observing a maximum or minimum boiling temperature that is higher or lower than the boiling point of any individual component.

[0036] The skilled artisan will appreciate that azeotropes or azeotrope-like compositions are identified by comparing the change in boiling point of the composition relative to the boiling point of the first component when a second component is added to the first component. Thus, in order to measure the change in boiling point, it is not necessary to calibrate the system to the reported boiling point of a specific component.

[0037] As previously mentioned, at the highest or lowest boiling point, the composition of the vapor phase will be the same as the composition of the liquid phase. Thus, an azeotrope-like composition is a composition that provides a substantially constant lowest or highest boiling point component, i.e., a boiling point between about -46.0°C and about 90.0°C at a pressure between about 4.9 psia and about 348 psia, such as, for example, a boiling point of about -22.50°C ± 0.30°C at a pressure of about 14.41 psia ± 0.30 psia, at which substantially constant boiling point, the composition of the vapor phase will be substantially the same as the composition of the liquid phase.

[0038] The present disclosure provides an azeotrope or azeotrope-like composition, the azeotrope or azeotrope-like composition comprises effective amounts of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) to form an azeotrope or azeotrope-like composition. As used herein, the term "effective amount" is the amount of each component that results in the formation of an azeotrope or azeotrope-like mixture when combined with other components.

[0039] The azeotrope or azeotrope-like composition of the present invention may consist essentially of the combination of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I), or consist of the combination of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I).

[0040] As used herein, with respect to the components of an azeotrope or azeotrope-like composition or mixture, the term "consisting essentially of" means that the composition comprises the indicated components in azeotropic or azeotrope-like ratios, and may comprise additional components, provided that the additional components do not form a new azeotrope or azeotrope-like system. For example, azeotropic mixtures consisting essentially of two compounds are those that form a binary azeotrope, which optionally may comprise one or more additional components, provided that the additional components do not render the mixture non-azeotropic and do not form an azeotrope with either or both compounds (e.g., do not form a ternary or higher azeotrope).

[0041] The present disclosure also provides a method for forming an azeotrope or azeotrope-like composition by mixing, combining or blending effective amounts of trifluoroacetyl chloride (CFCOCl) and trifluoroiodomethane (CFI). Any of the various methods known in the art for combining two or more components to form a composition can be used in the method of the present invention. For example, trifluoroacetyl chloride (CFCOCl) and trifluoroiodomethane (CFI) can be mixed, blended or otherwise combined manually and / or by machine as part of a batch or continuous reaction and / or process, or mixed, blended or otherwise combined via a combination of two or more such steps. Trifluoroacetyl chloride (CFCOCl) and trifluoroiodomethane (CFI) are both commercially available and can be purchased from several different suppliers. The components can be provided in the desired amount, such as by weighing, and then combining these amounts.

[0042] The azeotrope or azeotrope-like composition has a boiling point between about -46.0°C and about 90.0°C at a pressure between about 4.9 psia and about 348 psia, and consists essentially of or consists of about 0.5 wt % to about 99.0 wt % trifluoroacetyl chloride (CF3COCl) and about 1.0 wt % to about 99.5 wt % trifluoroiodomethane (CF3I).

[0043] Azeotrope or azeotrope-like composition having a boiling point between about -46.0°C and about 90.0°C at a pressure between about 4.9 psia and about 348 psia can also consist essentially of or consist of about 4.4 wt%, 10.7 wt%, 16.9 wt%, 23.1 wt%, 29.3 wt%, 35.5 wt%, 41.9 wt%, 48.4 wt%, 55.1 wt%, 62.1 wt%, 69.7 wt%, 77.9 wt%, 87.3 wt%, %, or 99.0 wt % of trifluoroacetyl chloride (CF3COCl), or in any range defined between any two of the foregoing values, and about 95.6 wt %, 89.3 wt %, 83.1 wt %, 76.9 wt %, 70.7 wt %, 64.5 wt %, 58.1 wt %, 51.6 wt %, 44.9 wt %, 37.9 wt %, 30.3 wt %, 22.1 wt % or 12.7 wt % of trifluoroiodomethane (CF3I), or in any range defined between any two of the foregoing values.

[0044] Additional azeotropic compositions include: about 99.5 wt % trifluoroiodomethane (CF3I) and about 0.5 wt % trifluoroacetyl chloride (CF3COCl) at a temperature of -46.0°C and a pressure of about 4.9 psia; about 95.6 wt % trifluoroiodomethane (CF3I) and about 4.4 wt % trifluoroacetyl chloride (CF3COCl) at a temperature of -40.0°C and a pressure of about 6.6 psia; about 89.3 wt % trifluoroiodomethane (CF3I) and about 10.7 wt % trifluoroacetyl chloride (CF3COCl) at a temperature of -30.0°C and a pressure of about 10.5 psia; about 83.1 wt % trifluoroiodomethane (CF3I) and about 10.7 wt % trifluoroacetyl chloride (CF3COCl) at a temperature of -20.0°C and a pressure of about 16.0 psia. % trifluoroiodomethane (CF3I) and about 16.9 wt % trifluoroacetyl chloride (CF3COCl); at a temperature of -10.0°C and a pressure of about 23.5 psia, about 76.9 wt % trifluoroiodomethane (CF3I) and about 23.1 wt % trifluoroacetyl chloride (CF3COCl); at a temperature of 0.0°C and a pressure of about 33.7 psia, about 70.7 wt % trifluoroiodomethane (CF3I) and about 29.3 wt % trifluoroacetyl chloride (CF3COCl); at a temperature of 10.0°C and a pressure of about 46.9 psia, about 64.5 wt % trifluoroiodomethane (CF3I) and about 35.5 wt % trifluoroacetyl chloride (CF3COCl); at a temperature of 2 ... ℃ temperature and about 63.9 psia pressure, about 58.1 wt % trifluoroiodomethane (CF3I) and about 41.9 wt % trifluoroacetyl chloride (CF3COCl); at a temperature of 30.0 ℃ and a pressure of about 85.1 psia, about 51.6 wt % trifluoroiodomethane (CF3I) and about 48.4 wt % trifluoroacetyl chloride (CF3COCl); at a temperature of 40.0 ℃ and a pressure of about 111.4 psia, about 44.9 wt % trifluoroiodomethane (CF3I) and about 55.1 wt % trifluoroacetyl chloride (CF3COCl); at a temperature of 50.0 ℃ and a pressure of about 143.5 psia, about 37.9 wt % trifluoroiodomethane (CF3I) and about % trifluoroacetyl chloride (CF3COCl); about 30.3 wt % trifluoroiodomethane (CF3I) and about 69.7 wt % trifluoroacetyl chloride (CF3COCl) at a temperature of 60.0°C and a pressure of about 182.1 psia; about 22.1 wt % trifluoroiodomethane (CF3I) and about 77.9 wt % trifluoroacetyl chloride (CF3COCl) at a temperature of 70.0°C and a pressure of about 228.2 psia; about 12.7 wt % trifluoroiodomethane (CF3I) and about 87.3 wt % trifluoroacetyl chloride (CF3COCl) at a temperature of 80.0°C and a pressure of about 283.1 psia; and about 90.0°C and a pressure of about 348.About 1.0 wt % trifluoroiodomethane (CF3I) and about 99.0 wt % trifluoroacetyl chloride (CF3COCl) at a pressure of 0 psia.

[0045] The azeotrope or azeotrope-like composition may consist essentially of or consist of about 0.5 wt % to about 25 wt % trifluoroacetyl chloride (CF3COCl), about 2 wt % to about 21 wt % trifluoroacetyl chloride (CF3COCl), about 14 wt % to about 18 wt % trifluoroacetyl chloride (CF3COCl), and in an azeotrope, about 14.87 wt % trifluoroacetyl chloride (CF3COCl), and about 75 wt % to about 99.5 wt % trifluoroiodomethane (CF3I), about 79 wt % to about 98 wt % trifluoroiodomethane (CF3I), about 82 wt % to about 86 wt % trifluoroiodomethane (CF3I), and in an azeotrope, about 85.13 wt % trifluoroiodomethane (CF3I). The azeotrope or azeotrope-like composition has a boiling point of about -22.50°C ± 0.30°C at a pressure of about 14.41 psia ± 0.30 psia.

[0046] In other words, the azeotrope or azeotrope-like composition may consist essentially of or consist of about 0.5 wt % to about 25 wt % trifluoroacetyl chloride (CF3COCl) and about 75 wt % to about 99.5 wt % trifluoroiodomethane (CF3I), about 2 wt % to about 21 wt % trifluoroacetyl chloride (CF3COCl) and about 79 wt % to about 98 wt % trifluoroiodomethane (CF3I), or about 14 wt % to about 18 wt % trifluoroacetyl chloride (CF3COCl) and about 82 wt % to about 86 wt % trifluoroiodomethane (CF3I), and in one azeotrope, about 14.87 wt % trifluoroacetyl chloride (CF3COCl) and about 85.13 wt % trifluoroiodomethane (CF3I). The azeotrope or azeotrope-like composition has a boiling point of about -22.50°C ± 0.30°C at a pressure of about 14.41 psia ± 0.30 psia.

[0047] In other words, the azeotrope or azeotrope-like composition consists essentially of or consists of trifluoroacetyl chloride (CFCOCl) as low as about 0.5%, about 2%, or about 14%, or as high as about 18%, about 21%, or about 25%, by weight, or in any range defined between any two of the foregoing values, and the azeotrope or azeotrope-like composition consists essentially of or consists of trifluoroiodomethane (CFI) as low as about 75%, about 79%, or about 82%, or as high as about 86%, about 98%, or about 99.5%, by weight, or in any range defined between any two of the foregoing values. The azeotrope composition consists essentially of or consists of about 14.87% by weight of trifluoroacetyl chloride (CFCOCl) and about 85.13% by weight of trifluoroiodomethane (CFI). The azeotrope or azeotrope-like compositions of the present disclosure have a boiling point of about -22.50°C ± 0.30°C at a pressure of about 14.41 psia ± 0.30 psia.

[0048] The present disclosure also provides a composition comprising an azeotrope or azeotrope-like composition. For example, a composition is provided, the composition comprising at least about 14% by weight of an azeotrope or azeotrope-like composition, or at least about 21% by weight of an azeotrope or azeotrope-like composition, or at least about 25% by weight of an azeotrope or azeotrope-like composition, or at least about 70% by weight of an azeotrope or azeotrope-like composition, or at least about 90% by weight of an azeotrope or azeotrope-like composition.

[0049] The azeotrope or azeotrope-like compositions disclosed herein comprising, consisting essentially of, or consisting of effective amounts of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) can be used to separate impurities from trifluoroacetyl chloride (CF3COCl) and / or trifluoroiodomethane (CF3I). One impurity that may be present in trifluoroiodomethane (CF3I) is trifluoromethane (HFC-23).

[0050] The preparation of an azeotrope or azeotrope-like composition comprising, consisting essentially of, or consisting of effective amounts of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) allows the use of separation techniques such as, for example, azeotropic distillation to remove impurities from trifluoroiodomethane (CF3I), thereby providing high purity trifluoroiodomethane (CF3I).

[0051] Specifically, an azeotrope or azeotrope-like composition comprising, consisting essentially of, or consisting of effective amounts of trifluoroacetyl chloride (CFCOCl) and trifluoroiodomethane (CFI) can be formed from a composition comprising one or both of trifluoroacetyl chloride (CFCOCl) and trifluoroiodomethane (CFI) together with one or more other compounds other than trifluoroacetyl chloride (CFCOCl) and trifluoroiodomethane (CFI), such as impurities. One such impurity is, for example, trifluoromethane (HFC-23). ​​After the azeotrope or azeotrope-like composition is formed, the azeotrope or azeotrope-like composition can be separated from the other compounds by a suitable method, such as by distillation, phase separation, or fractional distillation.

[0052] In one example, the present disclosure provides a method for separating trifluoroacetyl chloride (CF3COCl) as an impurity from a primary crude composition of trifluoroiodomethane (CF3I), the primary crude composition comprising trifluoroacetyl chloride (CF3COCl) as an impurity and at least one additional impurity, the method comprising the steps of: providing a primary composition of crude trifluoroiodomethane (CF3I), trifluoroacetyl chloride (CF3COCl) as an impurity, and at least one additional impurity; and subjecting the primary composition to conditions effective to form a secondary composition, the secondary composition being an azeotrope or azeotrope-like composition, the azeotrope or azeotrope-like composition consisting essentially of or consisting of an effective amount of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I); and separating the secondary composition from the primary composition by separation techniques such as phase separation, distillation, or fractionation, for example. The secondary composition may then be subjected to further separation or purification steps to obtain purified trifluoroiodomethane (CF3I).

[0053] In another example, a composition comprising one of trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl) and at least one impurity can be provided. A sufficient amount of the other of trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl) is added to the composition, and the composition is subjected to conditions effective to form a composition that is an azeotrope or azeotrope-like composition consisting essentially of or consisting of effective amounts of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I), and then the azeotrope or azeotrope-like composition is separated from the impurities by a separation technique such as phase separation, distillation, or fractionation. The azeotrope or azeotrope-like composition of trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl) can then be subjected to a further separation or purification step to obtain purified trifluoroiodomethane (CF3I).

[0054] In another example, discussed in detail in Example 3 below, the pressure sensitivity of the azeotrope compositions of the present invention allows for the separation of a composition comprising trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) by "pressure swing" distillation to form substantially pure compositions of each of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I).

[0055] A method for separating trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) from a primary composition comprising trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) comprises an initial step of conveying a feed stream comprising the primary composition to a low-pressure column. A bottom product can be collected from the low-pressure column, the bottom product consisting essentially of pure trifluoroacetyl chloride (CF3COCl). A first distillate from the low-pressure column is then conveyed to a high-pressure column, wherein the first distillate is an azeotrope or azeotrope-like composition consisting essentially of an effective amount of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I). A second bottom product can be collected from a high-pressure column consisting essentially of pure trifluoroiodomethane (CF3I). The method may also include, after the second collecting step, an additional step of recycling the second distillate from the high-pressure column back to the feed stream comprising the primary composition.

[0056] Similarly, another method for separating trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) from a primary composition comprising trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) comprises an initial step of conveying a feed stream comprising the primary composition to a high pressure column. The bottom product can be collected from the high pressure column consisting essentially of pure trifluoroiodomethane (CF3I). The first distillate from the high pressure column is then conveyed to a low pressure column, wherein the first distillate is an azeotrope or azeotrope-like composition consisting essentially of an effective amount of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I). A second bottom product can be collected from the low pressure column, the bottom product consisting essentially of trifluoroacetyl chloride (CF3COCl). The method may also include, after the second collecting step, an additional step of recycling the second distillate from the low pressure column back to the feed stream comprising the primary composition.

[0057] The following non-limiting examples serve to illustrate the present disclosure.

[0058] Example

[0059] Example 1 - Ebulliometer Studies

[0060] The azeotrope and azeotrope-like compositions of trifluoroacetyl chloride (CFCOCl) and trifluoroiodomethane (CFI) were measured using an ebulliometer. The ebulliometer consisted of a vacuum jacketed glass container that was sealed at the bottom and open to the atmosphere at the top. The top or condenser jacket of the ebulliometer was filled with a mixture of dry ice and ethanol at a pressure of 14.4 psia to obtain a temperature of about -72°C, which is significantly lower than the saturation temperatures of -20.2°C for trifluoroacetyl chloride (CFCOCl) and -22.4°C for trifluoroiodomethane (CFI). In this way, it was ensured that all vapors in the system were condensed and flowed back into the ebulliometer so that the liquid and vapor phases were in equilibrium. A quartz-platinum thermometer with an accuracy of +0.002°C was inserted into the glass container and used to determine the temperature of the condensed vapor corresponding to the equilibrium boiling point of the mixture. Zeolites were used to help keep the mixture boiling steadily in the ebulliometer.

[0061] Use the following procedure.

[0062] 1. Immerse a quartz thermometer in a long Dewar containing an ice / water slurry and verify that the thermometer reads 0°C. The Dewar is deep enough so that at least 3 / 4 of the length of the thermometer shaft is submerged in the ice / water. Record the thermometer resistance in ohms.

[0063] 2. Fill the condenser jacket to 1 / 4 full with ethanol. Cool the condenser jacket by slowly introducing dry ice to avoid boiling over and / or splashing of the ethanol.

[0064] 3. Add a known amount of trifluoroiodomethane (CF3I) or trifluoroacetyl chloride (CF3COCl) to the ebulliometer and bring to vigorous reflux conditions. Use a barometer with a temperature indicator to record the temperature and atmospheric pressure.

[0065] The measurement is carried out in two steps. In the first step, about 24.15 g of trifluoroiodomethane (CF3I) (measured according to gas chromatography (GC), purity is 99.88 area %) is first introduced into the ebulliometer by using a balance with an accuracy of ± 0.01 g to weigh the container before and after the addition. The liquid is boiled, and the equilibrium temperature of trifluoroiodomethane (CF3I) under the recorded gas pressure is recorded. Then, trifluoroacetyl chloride (CF3COCl) (measured according to gas chromatography (GC), purity is 98 area %) is introduced into the ebulliometer with a small increment, and the equilibrium temperature of the condensed liquid mixture is recorded.

[0066] In the second step, about 15.66 g of trifluoroacetyl chloride (CF3COCl) (98 area % purity according to gas chromatography (GC)) was introduced into the ebulliometer by weighing the container before and after addition using a balance with an accuracy of ±0.01 g. The liquid was boiled and the equilibrium temperature of trifluoroacetyl chloride (CF3COCl) at the recorded pressure was recorded. Then, trifluoroiodomethane (CF3I) (99.88 area % purity according to gas chromatography (GC)) was introduced into the ebulliometer in small increments and the equilibrium temperature of the condensed liquid mixture was recorded.

[0067] The data from the first and second steps described above are combined to complete the composition range data for each of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) given in Table 1 below, which shows the minimum temperature indicating that an azeotrope has been formed, and the data is also shown in graphical form at Figure 1 The bubble point temperature of the mixture remains constant, indicating that the mixture is azeotrope-like over a large composition range.

[0068] Table 1 - Ebulliometer Study of CF3I / Trifluoroacetyl Chloride at P = 14.4 psia

[0069] Temperature(℃) <![CDATA[Weight percentage of CF3I]]> <![CDATA[Weight percentage of CF3COCl]]> -22.36 100.00 0.00 -22.41 97.58 2.42 -22.45 95.80 4.20 -22.50 90.25 9.75 -22.51 85.13 14.87 -22.49 82.28 17.72 -22.47 78.66 21.34 -22.44 74.95 25.05 -22.40 70.68 29.32 -22.34 65.75 34.25 -22.31 63.84 36.16 -22.21 58.36 41.64 -22.13 55.24 44.76 -22.20 58.02 41.98 -22.09 52.73 47.27 -22.03 50.27 49.73 -21.89 44.55 55.45 -21.78 39.65 60.35 -21.67 36.80 63.20 -21.58 33.53 66.47 -21.23 20.95 79.05 -20.90 15.94 84.06 -20.78 12.47 87.53 -20.68 9.53 90.47 -20.54 7.17 92.83 -20.45 4.92 95.08 -20.30 2.06 97.94 -20.23 0.00 100.00

[0070] Example 2 - Azeotrope Trajectory

[0071] In "A Generalized Model for the Thermodynamic Properties of Mixtures" by EW Lemmon et al., International Journal of Thermophysics, Vol. 20, pp. 825-835, 1999, the authors describe a method for accurately characterizing the thermodynamic properties of mixtures. The proposed Helmholtz Energy Equation of State (HEOS) takes into account the pure components and interaction parameters of the mixture components to determine any thermodynamic quantity, including the vapor and liquid equilibrium compositions of the mixture for determining the presence and composition of azeotropes. After reducing the ebulliometer measurements of Example 1 to the HEOS interaction parameters described on page 828 of the aforementioned publication, the pure component thermodynamic properties of both trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl) were incorporated, and the vapor-liquid equilibrium composition was evaluated using the thermodynamic relationships described on pages 830-831 of the aforementioned publication, and it was found that the azeotrope composition was unusually sensitive to system temperature and pressure.

[0072] For example, at the system pressure of the ebulliometer in Example 1 (14.4 psia), the azeotrope composition was determined to be about 85 wt % CF3I. However, at an elevated system pressure of about 47 psia, the azeotrope composition shifted closer to 65 wt % trifluoroiodomethane (CF3I). Without being bound by theory, the sensitivity of the azeotrope to system conditions appears to be a result of the relative volatility between trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl). Examining the VLE of these components as a function of different system conditions yielded the azeotrope trajectory shown in Table 2.

[0073] Table 2 - Azeotrope Trajectories

[0074]

[0075] Example 3 - Pressure Transformation Separation

[0076] A well-known consequence of azeotropic mixtures is that their components cannot be completely separated in a single distillation operation. For example, separation of a 50 / 50 wt % mixture of trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl) by a distillation column maintained at 14.4 psia, exhibiting azeotropic behavior as described in Example 1, will be limited to a composition between the endpoint of pure trifluoroacetyl chloride (CF3COCl) (i.e., 0 wt % trifluoroiodomethane (CF3I)) and the lowest boiling azeotrope composition (about 85 wt % trifluoroiodomethane (CF3I). In other words, distillation of the mixture under these conditions will not produce trifluoroiodomethane (CF3I) with a purity greater than 85 wt %. In order to resolve this fundamental obstacle of the azeotrope and obtain both purer trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl), a different separation strategy must be implemented.

[0077] As described in Example 2, the azeotrope composition of a binary mixture of trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl) was found to be unusually sensitive to system conditions. This sensitivity can be exploited to support better separation by pressure swing distillation. In this system, two distillation columns are used to sequentially separate the pressure sensitive azeotrope, one at an arbitrary relatively low pressure, and one at an arbitrary relatively high pressure. The columns can be arranged so that the lower pressure column is the first in the sequence. Alternatively, the higher pressure column can be the first in the sequence. For the purposes of this example, reference is made to Figure 2 and Figure 3 , the columns are arranged with the lower pressure column being first in the sequence.

[0078] A mixture of trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl) is first subjected to distillation at a relatively low pressure. The specific composition of the mixture can be tailored as desired. For the purposes of this representative example, a mixture containing 50% by weight of trifluoroiodomethane (CF3I) and 50% by weight of trifluoroacetyl chloride (CF3COCl) is used. Now see Figure 2 , designating the mixture as Composition A ("Comp. 'A'"). Figure 3 , mixed stream 10 is fed to distillation column 12 at an arbitrarily low pressure (20 psia for the purposes of this example).

[0079] like Figure 2 As shown, composition A ( Figure 3 The stream 10 in the mixture has not yet reached the azeotropic point. Therefore, the mixture can be separated into a fraction rich in one component of the mixture and an azeotrope or azeotrope-like composition. Here, the fraction rich in the higher boiling component trifluoroacetyl chloride (CF3COCl) is collected as the bottom product and Figure 2 and Figure 3 Designated as Composition C ("Comp. 'C'") in Figure 3 Designated as stream 16 in the present invention. Azeotrope or azeotrope-like composition Figure 2 and Figure 3 is designated as Composition B ("Comp. 'B'") and is derived from Figure 3 The mixture is then added to the distillate of the low pressure column 12 shown in FIG. Figure 3 Stream 14 in is then passed to column 14 at an arbitrarily higher pressure (100 psia for the purposes of this example).

[0080] See now Figure 2 , the point representing composition B in the high pressure curve is now on the other side of the azeotrope composition compared to the low pressure curve. This allows the collection of fractions enriched in the other components of the mixture. In this example, the fraction enriched in trifluoroiodomethane (CF3I) is collected as the bottom product and Figure 2 and Figure 3 Designated as Composition D ("Comp. 'D'") in Figure 3 As with the lower pressure column, the distillate contains an azeotrope or azeotrope-like mixture. This mixture can be recycled back to the Figure 3 The composition A after stream 22 in is mixed.

[0081] In this way, the azeotrope barrier is resolved using the sensitivity of the azeotrope composition to the column conditions to produce two streams enriched in the two components. It is important to note that the details in this example are intended to be illustrative. Depending on the context of the mixture, column conditions and configurations can be designed to support almost any desired purity of trifluoroiodomethane (CF3I) and / or trifluoroacetyl chloride (CF3COCl).

[0082] Example 4 - Separation of impurities

[0083] In this embodiment, a crude composition of trifluoroiodomethane (CF3I) is provided, the crude composition comprising trifluoroacetyl chloride (CF3COCl) as an impurity and one or more other impurities such as trifluoromethane (HFC-23). ​​If necessary, the relative amounts of trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl) are changed to form sufficient relative amounts, and the composition is subjected to distillation under conditions effective to form an azeotrope or azeotrope-like composition of trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl) and separate it from the remainder of the composition. The separated azeotrope or azeotrope-like composition of trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl) is removed as a light component from the remaining crude composition of trifluoroiodomethane (CF3I). The remaining crude composition of trifluoroiodomethane (CF3I) is then subjected to different temperature and pressure conditions, wherein other impurities such as trifluoromethane (HFC-23) can be separated by further distillation to obtain purified trifluoroiodomethane (CF3I).

[0084] Example 5 - Separation of impurities

[0085] In this embodiment, a composition comprising trifluoroiodomethane (CF3I) and at least one impurity such as trifluoromethane (HFC-23), for example, is provided. A sufficient amount of trifluoroacetyl chloride (CF3COCl) is added to the composition, and the composition is subjected to conditions effective to form a composition that is an azeotrope or azeotrope-like composition consisting essentially of or consisting of effective amounts of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I), and then the azeotrope or azeotrope-like composition is separated from the impurities by separation techniques such as phase separation, distillation, or fractionation. The azeotrope or azeotrope-like composition of trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl) can then be subjected to further separation or purification steps to obtain purified trifluoroiodomethane (CF3I).

[0086] Example 6 - Separation of impurities

[0087] In this embodiment, a composition comprising trifluoroacetyl chloride (CF3COCl) and at least one impurity such as trifluoromethane (HFC-23), for example, is provided. A sufficient amount of trifluoroiodomethane (CF3I) is added to the composition, and the composition is subjected to conditions effective to form a composition that is an azeotrope or azeotrope-like composition consisting essentially of or consisting of effective amounts of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I), and then the azeotrope or azeotrope-like composition is separated from the impurities by separation techniques such as phase separation, distillation, or fractionation, for example. The azeotrope or azeotrope-like composition of trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl) can then be subjected to further separation or purification steps to obtain purified trifluoroiodomethane (CF3I).

[0088] aspect

[0089] Aspect 1 is an azeotrope or azeotrope-like composition comprising, consisting essentially of, or consisting of effective amounts of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I).

[0090] Aspect 2 is the azeotrope or azeotrope-like composition according to aspect 1, wherein the azeotrope or azeotrope-like composition has a boiling point between about -46.0°C and about 90.0°C at a pressure between about 4.9 psia and about 348 psia.

[0091] Aspect 3 is an azeotrope or azeotrope-like composition according to aspect 1 or 2, wherein the azeotrope or azeotrope-like composition consists essentially of about 0.5 wt % to about 99.0 wt % of trifluoroacetyl chloride (CF3COCl) and about 1.0 wt % to about 99.5 wt % of trifluoroiodomethane (CF3I).

[0092] Aspect 4 is an azeotrope composition comprising: about 99.5 wt % trifluoroiodomethane (CF3I) and about 0.5 wt % trifluoroacetyl chloride (CF3COCl) at a temperature of -46.0°C and a pressure of about 4.9 psia.

[0093] Aspect 5 is an azeotrope composition comprising: about 95.6 wt % trifluoroiodomethane (CF3I) and about 4.4 wt % trifluoroacetyl chloride (CF3COCl) at a temperature of -40.0°C and a pressure of about 6.6 psia.

[0094] Aspect 6 is an azeotrope composition comprising: about 89.3 wt % trifluoroiodomethane (CF3I) and about 10.7 wt % trifluoroacetyl chloride (CF3COCl) at a temperature of -30.0°C and a pressure of about 10.5 psia.

[0095] Aspect 7 is an azeotrope composition comprising: about 83.1 wt % trifluoroiodomethane (CF3I) and about 16.9 wt % trifluoroacetyl chloride (CF3COCl) at a temperature of -20.0°C and a pressure of about 16.0 psia.

[0096] Aspect 8 is an azeotrope composition comprising: about 76.9 wt % trifluoroiodomethane (CF3I) and about 23.1 wt % trifluoroacetyl chloride (CF3COCl) at a temperature of -10.0°C and a pressure of about 23.5 psia.

[0097] Aspect 9 is an azeotrope composition comprising: about 70.7 wt % trifluoroiodomethane (CF3I) and about 29.3 wt % trifluoroacetyl chloride (CF3COCl) at a temperature of 0.0°C and a pressure of about 33.7 psia.

[0098] Aspect 10 is an azeotrope composition comprising: about 64.5 wt % trifluoroiodomethane (CF3I) and about 35.5 wt % trifluoroacetyl chloride (CF3COCl) at a temperature of 10.0°C and a pressure of about 46.9 psia.

[0099] Aspect 11 is an azeotrope composition comprising: about 58.1 wt % trifluoroiodomethane (CF3I) and about 41.9 wt % trifluoroacetyl chloride (CF3COCl) at a temperature of 20.0°C and a pressure of about 63.9 psia.

[0100] Aspect 12 is an azeotrope composition comprising: about 51.6 wt % trifluoroiodomethane (CF3I) and about 48.4 wt % trifluoroacetyl chloride (CF3COCl) at a temperature of 30.0°C and a pressure of about 85.1 psia.

[0101] Aspect 13 is an azeotrope composition comprising: about 44.9 wt % trifluoroiodomethane (CF3I) and about 55.1 wt % trifluoroacetyl chloride (CF3COCl) at a temperature of 40.0°C and a pressure of about 111.4 psia.

[0102] Aspect 14 is an azeotrope composition comprising: about 37.9 wt % trifluoroiodomethane (CF3I) and about 62.1 wt % trifluoroacetyl chloride (CF3COCl) at a temperature of 50.0°C and a pressure of about 143.5 psia.

[0103] Aspect 15 is an azeotrope composition comprising: about 30.3 wt % trifluoroiodomethane (CF3I) and about 69.7 wt % trifluoroacetyl chloride (CF3COCl) at a temperature of 60.0°C and a pressure of about 182.1 psia.

[0104] Aspect 16 is an azeotrope composition comprising: about 22.1 wt % trifluoroiodomethane (CF3I) and about 77.9 wt % trifluoroacetyl chloride (CF3COCl) at a temperature of 70.0°C and a pressure of about 228.2 psia.

[0105] Aspect 17 is an azeotrope composition comprising: about 12.7 wt % trifluoroiodomethane (CF3I) and about 87.3 wt % trifluoroacetyl chloride (CF3COCl) at a temperature of 80.0°C and a pressure of about 283.1 psia.

[0106] Aspect 18 is an azeotrope composition comprising: about 1.0 wt % trifluoroiodomethane (CF3I) and about 99.0 wt % trifluoroacetyl chloride (CF3COCl) at a temperature of 90.0°C and a pressure of about 348.0 psia.

[0107] Aspect 19 is an azeotrope or azeotrope-like composition according to aspect 1, which comprises, consists essentially of, or consists of about 0.5 wt % to about 25 wt % of trifluoroacetyl chloride (CF3COCl) and about 75 wt % to about 99.5 wt % of trifluoroiodomethane (CF3I).

[0108] Aspect 20 is an azeotrope or azeotrope-like composition according to aspect 19, which comprises, consists essentially of, or consists of about 2 weight percent to about 21 weight percent of trifluoroacetyl chloride (CF3COCl) and about 79 weight percent to about 98 weight percent of trifluoroiodomethane (CF3I).

[0109] Aspect 21 is an azeotrope or azeotrope-like composition according to aspect 20, which comprises, consists essentially of, or consists of about 14 wt % to about 18 wt % of trifluoroacetyl chloride (CF3COCl) and about 82 wt % to about 86 wt % of trifluoroiodomethane (CF3I).

[0110] Aspect 22 is an azeotrope or azeotrope-like composition according to aspect 21, which comprises, consists essentially of, or consists of about 14.87 weight percent trifluoroacetyl chloride (CF3COCl) and about 85.13 weight percent trifluoroiodomethane (CF3I).

[0111] Aspect 23 is an azeotrope or azeotrope-like composition according to any one of aspects 19 to 22, wherein the composition has a boiling point of about -22.50°C ± 0.30°C at a pressure of about 14.41 psia ± 0.30 psia.

[0112] Aspect 24 is an azeotrope or azeotrope-like composition according to any one of aspects 1 to 18, wherein the azeotrope or azeotrope-like composition consists essentially of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I).

[0113] Aspect 25 is an azeotrope or azeotrope-like composition according to any one of aspects 1 to 18, wherein the azeotrope or azeotrope-like composition consists of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I).

[0114] Aspect 26 is a composition comprising, consisting essentially of, or consisting of the azeotrope or azeotrope-like composition according to any one of aspects 1 to 18.

[0115] Aspect 27 is a composition according to aspect 26, comprising, consisting essentially of, or consisting of at least about 5 weight percent of the azeotrope or azeotrope-like composition.

[0116] Aspect 28 is the composition of aspect 27, comprising, consisting essentially of, or consisting of at least about 15 weight percent of the azeotrope or azeotrope-like composition.

[0117] Aspect 29 is the composition of aspect 28, comprising, consisting essentially of, or consisting of at least about 50 weight percent of the azeotrope or azeotrope-like composition.

[0118] Aspect 30 is the composition of aspect 29, comprising, consisting essentially of, or consisting of at least about 70 wt % of the azeotrope or azeotrope-like composition.

[0119] Aspect 31 is a composition according to aspect 30, comprising, consisting essentially of, or consisting of at least about 90 weight percent of the azeotrope or azeotrope-like composition.

[0120] Aspect 32 is a method of forming an azeotrope or azeotrope-like composition, the method comprising the step of combining trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) to form an azeotrope or azeotrope-like composition, the azeotrope or azeotrope-like composition comprising, consisting essentially of, or consisting of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I), and having a boiling point between about -46.0°C and about 90.0°C at a pressure between about 4.9 psia and about 348 psia.

[0121] Aspect 33 is a method according to aspect 32, wherein the combining step comprises combining about 0.5 wt % to about 99.0 wt % of trifluoroacetyl chloride (CF3COCl) and about 1.0 wt % to about 99.5 wt % of trifluoroiodomethane (CF3I).

[0122] Aspect 34 is a method of forming an azeotrope or azeotrope-like composition, the method comprising the step of combining trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) to form the azeotrope or azeotrope-like composition, the azeotrope or azeotrope-like composition comprising effective amounts of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I).

[0123] Aspect 35 is a method according to aspect 34, comprising the step of combining trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) to form an azeotrope or azeotrope-like composition according to any one of aspects 1 to 18.

[0124] Aspect 35 is a method for separating trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) from a primary composition comprising trifluoroacetyl chloride (CF3COCl), trifluoroiodomethane (CF3I), and at least one impurity, the method comprising the steps of: forming a secondary composition within the primary composition, the secondary composition being an azeotrope or azeotrope-like composition, the azeotrope or azeotrope-like composition comprising, consisting essentially of, or consisting of effective amounts of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I), and having a boiling point between about -46.0°C and about 90.0°C at a pressure between about 4.9 psia and about 348 psia; and separating the secondary composition from the primary composition and the at least one impurity.

[0125] Aspect 36 is a method according to aspect 35, wherein the forming step includes forming a secondary composition within the primary composition, the secondary composition being an azeotrope or azeotrope-like composition, the azeotrope or azeotrope-like composition comprising, consisting essentially of, or consisting of about 0.5 wt % to about 99.0 wt % trifluoroacetyl chloride (CF3COCl) and about 1.0 wt % to about 99.5 wt % trifluoroiodomethane (CF3I).

[0126] Aspect 37 is a method according to aspect 35 or aspect 36, wherein the azeotrope or azeotrope-like composition is defined according to any one of aspects 1 to 18.

[0127] Aspect 38 is a method according to aspect 35 or aspect 36, wherein the separation is performed by at least one of phase separation, distillation and fractionation.

[0128] Aspect 39 is a method for separating trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) from a primary composition comprising trifluoroacetyl chloride (CF3COCl), trifluoroiodomethane (CF3I), and at least one impurity, the method comprising the steps of: forming a secondary composition within the primary composition, the secondary composition being an azeotrope or azeotrope-like composition, the azeotrope or azeotrope-like composition comprising, consisting essentially of, or consisting of effective amounts of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I); and separating the secondary azeotrope or azeotrope-like composition from the primary composition and the at least one impurity.

[0129] Aspect 40 is the method according to aspect 39, wherein the azeotrope or azeotrope-like composition is defined as described in any one of aspects 1 to 18.

[0130] Aspect 41 is a method according to aspect 39 or aspect 40, wherein the separation is performed by at least one of phase separation, distillation and fractionation.

[0131] Aspect 42 is a method of separating trifluoroacetyl chloride (CF3COCl) or trifluoroiodomethane (CF3I) from at least one impurity, the method comprising the steps of providing a composition comprising one of trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl) and at least one impurity; adding a sufficient amount of the other of trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl), and subjecting the composition to conditions effective to form a composition that is an azeotrope or azeotrope-like composition consisting essentially of or consisting of effective amounts of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I), and separating the azeotrope or azeotrope-like composition from the impurity.

[0132] Aspect 43 is a method according to aspect 42, wherein the azeotrope or azeotrope-like composition is defined as described in any one of aspects 1 to 18.

[0133] Aspect 44 is a method according to aspect 42 or aspect 43, wherein the separation is performed by at least one of phase separation, distillation and fractionation.

[0134] Aspect 45 is a method for separating trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) from a primary composition comprising trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I), the method comprising the steps of: conveying a feed stream comprising the primary composition to a low-pressure column; collecting a first bottoms product from the low-pressure column, the first bottoms product consisting essentially of trifluoroacetyl chloride (CF3COCl); conveying a first distillate from the low-pressure column to a high-pressure column, the first distillate comprising, consisting essentially of, or consisting of an azeotrope or azeotrope-like composition consisting essentially of effective amounts of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I); and collecting a second bottoms product from the high-pressure column, the second bottoms product consisting essentially of trifluoroiodomethane (CF3I).

[0135] Aspect 46 is a method according to aspect 45, further comprising an additional step of recycling the second distillate from the high-pressure column back to the feed stream comprising the primary composition after the second collecting step.

[0136] Aspect 47 is a method for separating trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) from a primary composition comprising trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I), the method comprising the steps of: conveying a feed stream comprising the primary composition to a high-pressure column; collecting a first bottoms product from the high-pressure column, the first bottoms product consisting essentially of trifluoroiodomethane (CF3I); conveying a first distillate from the high-pressure column to a low-pressure column, the first distillate comprising, consisting essentially of, or consisting of an azeotrope or azeotrope-like composition consisting essentially of effective amounts of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I); and collecting a second bottoms product from the low-pressure column, the second bottoms product consisting essentially of trifluoroacetyl chloride (CF3COCl).

[0137] Aspect 48 is a method according to aspect 47, further comprising an additional step of recycling the second distillate from the low-pressure column back to the feed stream comprising the primary composition after the second collecting step.

[0138] As used herein, the phrase "in any range defined between any two preceding values" literally means that any range can be selected from any two values ​​listed before such phrase, regardless of whether these values ​​are in the lower part of the list or in the upper part of the list. For example, a pair of values ​​can be selected from two lower values, two higher values, or a lower value and an upper value.

[0139] As used herein, the singular forms "a", "an", and "the" include the plural, unless otherwise explicitly indicated in the context. In addition, when an amount, concentration, or other value or parameter is given as a range, a preferred range, or a list of upper preferred values ​​and lower preferred values, it should be understood that all ranges formed by any pair of any upper range or preferred value and any lower range or preferred value are specifically disclosed, regardless of whether these ranges are disclosed individually. When a range of values ​​is listed in this article, unless otherwise specified, the range is intended to include its end value and all integers and fractions within the range. When limiting a range, it is not intended that the scope of the present disclosure be limited to the specific values ​​listed.

[0140] It should be understood that the above description is merely an illustration of the present disclosure. Without departing from the present disclosure, those skilled in the art may design various alternatives and modifications. Therefore, the present disclosure is intended to cover all such alternatives, modifications and variations that fall within the scope of the appended claims.

Claims

1. A composition comprising an azeotrope or azeotrope-like composition, wherein the azeotrope or azeotrope-like composition is composed of effective amounts of 0.5 wt % to 35.5 wt % trifluoroacetyl chloride (CF3COCl) and 64.5 wt % to 99.5 wt % trifluoroiodomethane (CF3I).

2. The composition of claim 1, wherein the azeotrope or azeotrope-like composition has a boiling point between -46.0°C and 90.0°C at a pressure between 4.9 psia and 348 psia.

3. The composition of claim 1, wherein the azeotrope or azeotrope-like composition consists of 0.5 wt % to 10.7 wt % trifluoroacetyl chloride (CF3COCl) and 89.3 wt % to 99.5 wt % trifluoroiodomethane (CF3I).

4. The composition of claim 1, wherein the azeotrope or azeotrope-like composition has a boiling point of -22.50°C ± 0.30°C at a pressure of 14.41 psia ± 0.30 psia.

5. The composition of claim 1, wherein the azeotrope or azeotrope-like composition consists of 0.5 wt % to 25 wt % trifluoroacetyl chloride (CF3COCl) and 75 wt % to 99.5 wt % trifluoroiodomethane (CF3I).

6. The composition of claim 1, wherein the azeotrope or azeotrope-like composition consists of 2 wt % to 21 wt % trifluoroacetyl chloride (CF3COCl) and 79 wt % to 98 wt % trifluoroiodomethane (CF3I).

7. The composition of claim 1, wherein the azeotrope or azeotrope-like composition consists of 14 to 18 wt % trifluoroacetyl chloride (CF3COCl) and 82 to 86 wt % trifluoroiodomethane (CF3I).

8. A method of forming an azeotrope or azeotrope-like composition, the method comprising the step of combining trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) to form an azeotrope or azeotrope-like composition as defined in any one of claims 1 to 7.

9. The method of claim 8, wherein the step of combining trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) comprises combining 0.5 wt % to 10.7 wt % of trifluoroacetyl chloride (CF3COCl) and 89.3 wt % to 99.5 wt % of trifluoroiodomethane (CF3I).

10. A method for separating trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) from a primary composition comprising trifluoroacetyl chloride (CF3COCl), trifluoroiodomethane (CF3I) and at least one impurity, the method comprising the steps of: forming a secondary composition within the primary composition, the secondary composition being an azeotrope or azeotrope-like composition as defined in any one of claims 1 to 7; as well as The secondary composition is separated from the primary composition and the at least one impurity.

11. A method for producing trifluoroiodomethane (CF3I) using the composition defined in any one of claims 1 to 7.

12. A method for producing trifluoroiodomethane (CF3I) comprising the method defined in any one of claims 8 to 10.

Images