Azeotropic and azeotrope-like compositions of trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl)

Abstract

To provide compositions and methods that may be used to prepare iodide-containing compounds, such as trifluoroiodomethane, of high purity.SOLUTION: Provided is a composition comprising an azeotropic or azeotrope-like composition, comprising 0.5 wt.% to 35.5 wt.% of trifluoroacetyl chloride (CF3COCl) and 64.5 wt.% to 99.5 wt.% of trifluoroiodomethane (CF3I).SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present disclosure relates to azeotropic or azeotrope-like compositions, particularly trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl) in azeotropic or azeotrope-like compositions. Regarding. [Background technology]

[0002] Fluorocarbon fluids are used as refrigerants, aerosol propellants, blowing agents, heat transfer media, gaseous It has found widespread use in industry in many applications, including electrical and flame suppressants. are.

[0003] However, chlorofluorocarbons (CFCs) and hydrofluorocarbons Certain compounds such as hydrochlorofluorocarbons (HCFCs) is believed to deplete atmospheric ozone and is therefore harmful to the environment. Some of these compounds are thought to contribute to global warming. Hydrofluorocarbons (HFCs) and other fluorocarbons with low ozone depletion potential Fluorocarbon fluids with low or even zero atmospheric It is desirable to use a substance that has a photodecomposable carbon-iodine bond that exhibits a long life. And the use of single component fluids or azeotropes that do not fractionate upon evaporation is also desirable. Summary of the Invention [Problem to be solved by the invention]

[0004] Unfortunately, the fact that azeotrope formation is unpredictable has led to the development of new environmentally safe non- Identification of fractional mixtures is complex.

[0005] The industry offers alternatives and is committed to the use of CFCs, HCFCs, and HF There is a lack of new fluorocarbon mixtures that are considered environmentally safer alternatives to C. Iodide-containing materials with low ozone depletion potential and low global warming potential are being pursued. Compounds and other fluorinated compounds are of particular interest. Such mixtures are the subject of this disclosure. do.

[0006] Although iodide-containing compounds offer significant potential benefits, Purification of iodide-containing compounds such as trifluoromethyl iodide (CF3I) is difficult. Removal of impurities from trifluoroiodomethane (CF3I) such as trifluoroiodomethane (HFC-23) Therefore, separation techniques such as azeotropic distillation are highly desirable. It is considered to be a good idea.

[0007] To prepare iodide-containing compounds such as highly pure trifluoroiodomethane (CF3I), What is needed are compositions and techniques that can be used to

[0008] The present disclosure relates to the use of trifluoroiodomethane (CF3I) and trifluoroacetyl chloride. The present invention provides azeotropic or azeotrope-like compositions of CF3COCl.

[0009] It is well recognized in the art that the formation of azeotropes is impossible to predict. Furthermore, the present inventors have reported that trifluoroiodomethane (CF3I) and trifluoro It is predicted that acetyl chloride (CF3COCl) will form an azeotropic or azeotrope-like composition. I discovered something unexpected.

[0010] The present disclosure provides a method for treating a pulmonary arthritis with an effective amount of trifluoroacetyl chloride (CF3COCl) and trifluoroacetyl chloride (CF3COCl). Azeotropic or azeotrope-like compounds consisting essentially of or consisting of iodomethane (CF3I) The azeotropic or azeotrope-like composition is provided at a pressure of from about 4.9 psia to about 3. It has a boiling point of about -46.0°C to about 90.0°C at a pressure of 48 psia, and is present in an amount of about 0.5% by weight to about 99.0% by weight of trifluoroacetyl chloride (CF3COCl) and approximately 1.0% by weight consisting essentially of, or about 99.5% by weight of, trifluoroiodomethane (CF3I); It consists of these.

[0011] The azeotropic or azeotrope-like composition may contain from about 0.5% to about 25% by weight of trifluoroacetyl chloride (CF3COCl), about 2% by weight to about 21% by weight of trifluoroacetyl chloride Fluoroacetyl chloride (CF3COCl), about 14% by weight to about 18% by weight CF3COCl), one azeotrope contains about 14.87 wt.% trifluoroacetyl chloride. trifluoroiodomethane (CF3COCl), and about 75% to about 99.5% by weight of trifluoroiodomethane Fluoroisopropyl ether (CF3I), about 79% by weight to about 98% by weight of trifluoroiodomethane (CF3I), ), about 82% to about 86% by weight of trifluoroiodomethane (CF3I), one azeotrope The product consists essentially of about 85.13% by weight of trifluoroiodomethane (CF3I). The azeotropic or azeotrope-like composition may have a viscosity of about 14.41 ps. It has a boiling point of about -22.50°C ± 0.30°C at a pressure of ia ± 0.30 psia.

[0012] In other words, the azeotropic or azeotrope-like composition contains from about 0.5% to about 25% by weight of trifle. Trifluoroacetyl chloride (CF3COCl), about 75% to about 99.5% by weight Oloiodomethane (CF3I), or about 2% to about 21% by weight of trifluoroacetyl chloride (CF3COCl), about 79% to about 98% by weight of trifluoroiodomethane (CF3I), or about 14% to about 18% by weight of trifluoroacetyl chloride (CF 3COCl), and about 82% to about 86% by weight of trifluoroiodomethane (CF3I ), and in one azeotrope, about 14.87 wt. % trifluoroacetyl chloride (C F3COCl) and approximately 85.13% by weight of trifluoroiodomethane (CF3I). Azeotropic or azeotrope-like compositions may be of a molecular weight of about 1400 or more. It has a boiling point of approximately -22.50°C ± 0.30°C at a pressure of 0.41 psia ± 0.30 psia. do.

[0013] The present disclosure also provides a method for producing a 14.41 psia ± 0.30 psia (14.41 psia ± 0.30 psia) 1000 psi (-2200 psi) 1000 psi ... Trifluoroacetyl chloride (CF3COCl) with a boiling point of 0.50°C ± 0.30°C and trifluoroiodomethane (CF3I), to provide.

[0014] The present disclosure also provides a method for forming an azeotropic or azeotrope-like composition, comprising: A combination of methyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) At pressures of about 4.9 psia and 348 psia, the temperature ranges from about -46.0°C to about 90. Trifluoroacetyl chloride (CF3COCl) and trifluoroacetyl chloride (CF3COCl) have a boiling point of 0°C. Azeotropic or azeotrope-like mixtures consisting essentially of or consisting of iodomethane (CF3I) The step of combining provides a composition comprising from about 0.5% to about 99.0% by weight of Trifluoroacetyl chloride (CF3COCl) and about 1.0% by weight to about 99.5% by weight % of trifluoroiodomethane (CF3I).

[0015] The present disclosure also provides trifluoroacetyl chloride (CF3COCl) and trifluoroacetyl chloride (CF3COCl). Iodomethane (CF3I) is combined with trifluoroacetyl chloride (CF3CO consisting essentially of, or consisting of, trifluoroisopropyl ether (CF3Cl) and trifluoroiodomethane (CF3I) 1. A method for forming an azeotrope or azeotrope-like composition, comprising the step of forming an azeotrope or azeotrope-like composition comprising: The azeotropic or azeotrope-like composition is a pressure of about 14.41 psia ± 0.30 psia. It may have a boiling point of about -22.50°C ± 0.30°C at pressure.

[0016] The present disclosure also provides trifluoroacetyl chloride (CF3COCl) and trifluoroacetyl chloride (CF3COCl). Iodomethane (CF3I) is converted to trifluoroacetyl chloride (CF3COCl), ... from a primary composition containing fluoroiodomethane (CF3I) and at least one impurity The present invention provides a method for isolating a compound comprising: Consists essentially of trifluoroiodomethane (CF3COCl) and trifluoroiodomethane (CF3I) forming a secondary composition, which is an azeotropic or azeotrope-like composition; and separating the primary composition from at least one impurity. At pressures of approximately 4.9 psia to 348 psia, the boiling point is approximately -46.0°C to approximately 90.0°C. About 0.5% by weight to about 99.0% by weight of trifluoroacetyl chloride (CF3 COCl) and about 1.0% by weight to about 99.0% by weight of trifluoroiodomethane (CF forming a secondary composition which is an azeotropic or azeotrope-like composition consisting essentially of That's fine too.

[0017] The present disclosure also provides trifluoroacetyl chloride (CF3COCl) or trifluoroacetyl chloride (CF3COCl). A method is provided which comprises separating iodomethane (CF3I) from at least one impurity. This method uses trifluoroiodomethane (CF3I) and trifluoroacetyl chloride. and (CF3COCl) together with at least one impurity. and adding sufficient amounts of other trifluoroiodomethane (CF3I) and trifluoromethyl iodide (TF3I). adding trifluoroacetyl chloride (CF3COCl); and adding the composition to an effective amount of trifluoromethyl ... from trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) to form a composition that is an azeotropic or azeotrope-like composition consisting essentially of, or consisting of, and subjecting the azeotropic or azeotrope-like composition to effective conditions, e.g., phase separation, distillation, or fractionation. and separating the azeotropic or azeotrope-like composition from impurities by a separation technique such as Conditions effective for formation are about -46.0 at pressures of about 4.9 psia to about 348 psia. 0.5% to about 99.0% by weight of a trifluoroacetate having a boiling point of 0.5°C to about 90.0°C Cetyl chloride (CF3COCl) and about 1.0% to about 99.0% by weight of trifluoromethyl methyl acrylate (TFMCMC). The method may include providing diiodomethane (CF3I).

[0018] The present disclosure also provides trifluoroacetyl chloride (CF3COCl) and trifluoroacetyl chloride (CF3COCl). Iodomethane (CF3I) was reacted with trifluoroacetyl chloride (CF3COCl) and trifluoroacetyl chloride (CF3COCl). a method for separating trifluoroiodomethane (CF3I) from a primary composition containing the same, The method includes conveying a feed stream containing a primary composition to a low-pressure column and extracting a first bottoms product (bo Toms product) consists essentially of trifluoroacetyl chloride (CF3COCl) recovering a first bottoms product from the low pressure column; and essentially consisting of trifluoroiodomethane (CF3I) and trifluoroiodomethane (CF3COCl) conveying a first distillate, containing an azeotropic or azeotrope-like composition, from the lower pressure column to the higher pressure column; and a second bottom product consisting essentially of trifluoroiodomethane (CF3I). and recovering the product from the high-pressure column. further comprising the additional step of returning the second distillate from the column to the feed stream containing the primary composition. Good too.

[0019] The present disclosure also provides trifluoroacetyl chloride (CF3COCl) and trifluoroacetyl chloride (CF3COCl). Iodomethane (CF3I) was reacted with trifluoroacetyl chloride (CF3COCl) and trifluoroacetyl chloride (CF3COCl). a method for separating trifluoroiodomethane (CF3I) from a primary composition containing the same, The method includes conveying a feed stream containing a primary composition to a high-pressure column; recovering a first bottoms product from the higher pressure column, the first bottoms product consisting essentially of CF3I. and an effective amount of trifluoroacetyl chloride (CF3COCl) and trifluoroiodine a first distillate comprising an azeotropic or azeotrope-like composition consisting essentially of methane (CF3I); conveying the second bottoms product from the higher pressure column to the lower pressure column; and a second bottoms product from the low pressure column consisting essentially of benzoyl chloride (CF3COCl); and recovering the second distillate from the low-pressure column after the second recovery step. The method may further include the additional step of returning the distillate to the feed stream containing the primary composition. [Brief explanation of the drawings]

[0020] [Figure 1] FIG. 1 is a plot of temperature versus weight percent of trifluoroiodomethane (CF3I) measured according to Example 1.

[0021] [Figure 2] FIG. 2 corresponds to Example 3 and is a plot of temperature versus composition (mass fraction of trifluoroiodomethane (CF3I)) with two curves placed at arbitrary low and arbitrary high pressures, respectively.

[0022] [Figure 3] FIG. 3 shows an exemplary pressure swing distillation configuration. DETAILED DESCRIPTION OF THE INVENTION

[0023] Trifluoroacetyl chloride (CF3COCl) is a fluoroisotope of trifluoroiodomethane ( Measure homogeneous, minimum boiling azeotropic and azeotrope-like compositions or form mixtures with CF3I. It has been found that trifluoroacetyl chloride (CF3COCl) and trifluoroacetyl chloride (CF3COCl) are effective in the synthesis of acetylacetonin. A homogeneous azeotropic or azeotrope-like composition containing trifluoroiodomethane (CF3I) is provided. Azeotropic or azeotrope-like compositions are trifluoroacetyl chloride (CF3COCl) and trifluoroacetyl chloride (CF3COCl). It may consist essentially of fluoroiodomethane (CF3I) or may be azeotropic or azeotrope-like. The composition comprises trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane. It may consist of titanium (CF3I).

[0024] The inventors have used trifluoroacetyl chloride (CF3COCl) and trifluoroacetyl chloride (CF3COCl). Iodomethane (CF3I) has been found experimentally to form azeotropic or azeotrope-like compositions. It was.

[0025] An "azeotropic" composition is a unique combination of two or more components. Azeotropic compositions can be characterized by various techniques. For example, at a given pressure, azeotropic compositions boils at a certain characteristic temperature higher than the higher-boiling component (maximum boiling point azeotrope) or boils at a characteristic temperature lower than the lower boiling point component (minimum boiling point azeotrope). At that temperature, the same composition will exist in both the vapor and liquid phases. The components of an azeotropic composition do not separate during the phase change. This is not possible.

[0026] Azeotropic compositions also have a liquid phase bubble point pressure at their characteristic azeotropic temperature. ) is the same as the dew point pressure of the gas phase.

[0027] The behavior of azeotropic compositions is characterized by non-azeotropic compositions in which the liquid composition changes to a significant extent during boiling or evaporation. This is in contrast to the behavior of effervescent compositions.

[0028] For purposes of this disclosure, an azeotropic composition is one that has certain properties below the boiling points of two or more components. boils at a temperature (minimum boiling point azeotrope), thereby having the same composition in both the vapor and liquid phases The composition is characterized as having:

[0029] However, one skilled in the art will appreciate that at different pressures, both the composition and boiling point of the azeotropic composition will change. It will be understood that the rate of change will vary to some extent depending on temperature and / or pressure. Azeotropic compositions can have variable compositions. Therefore, those skilled in the art can easily distinguish between fixed and variable compositions. It will be appreciated that a composition range rather than a composition can be used to define an azeotropic composition. Furthermore, an azeotrope is any mixture of compositions characterized by a fixed boiling point at a particular pressure. It can also be defined in terms of the exact weight percentage of the ingredients.

[0030] An "azeotrope-like" composition is a composition of two or more components that behaves substantially as an azeotrope. Thus, for purposes of this disclosure, an azeotrope-like composition is one that is in liquid form at a given pressure. a gas that boils at a substantially constant temperature when It is a combination of two or more different ingredients that provides a composition.

[0031] For purposes of this disclosure, an azeotrope-like composition is, for example, a composition having a viscosity of about 14.41 psia ± 0.3 Compositions or compositions that boil in the temperature range of about -22.50°C ± 0.30°C at a pressure of 0 psia is about -46 at pressures from about 4.9 psia to about 348 psia, including a range of compositions. A composition or range of compositions that boils in the temperature range of 0°C to about 90.0°C.

[0032] Azeotropic or azeotrope-like compositions can be identified using a number of different methods.

[0033] For purposes of this disclosure, azeotropic or azeotrope-like compositions are defined as those that are experimentally determined using an ebullometer. (Walas, Phase Equilibria in Chemica l Engineering,Butterworth-Heinemann,1985 ,533-544). The ebullometer measures the boiling point of a liquid by measuring the vapor-liquid equilibrium temperature. It is designed to provide extremely accurate measurements of points.

[0034] The boiling points of each of the components alone are measured at constant pressure. As such, for a two-component azeotropic or azeotrope-like composition, the boiling point of one of the components of the composition is The second component of the composition is then added in varying amounts, and the measured value is then measured at that constant value. The boiling point of each of the resulting compositions is measured using an ebullometer at a pressure of 1000 kJ / min.

[0035] The measured boiling point is relative to the composition of the tested composition, e.g., in the case of a binary azeotrope, The % saturation is plotted against the amount of the second component added to the composition (either by weight or mole percent). The existence of an azeotropic composition is indicated by the presence of a mixture whose boiling point is higher or equal to that of either component alone. can be identified by observing a low maximum or minimum boiling temperature.

[0036] As will be appreciated by those skilled in the art, the identification of an azeotropic or azeotrope-like composition involves the determination of the second component. By comparing the change in boiling point of the composition upon addition to the first component with the boiling point of the first component, Therefore, to measure the change in boiling point, the reported boiling point of a particular component is used. There is no need to calibrate the system.

[0037] As mentioned above, at the maximum or minimum boiling point, the composition of the gas phase is the same as the composition of the liquid phase. Therefore, an azeotrope-like composition is one that has a viscosity of about -4 at a pressure of about 4.9 psia to about 348 psia. Boiling point of 6.0°C to about 90.0°C, e.g., pressure of about 14.41 psia ± 0.30 psia A substantially constant minimum or maximum boiling point, such as a boiling point of about -22.50°C ± 0.30°C at The composition of the components that provide the point at which the vapor phase is at its substantially constant boiling point is the same as that of the liquid phase. The composition is substantially the same.

[0038] The present disclosure provides a method for treating a pulmonary arthritis with an effective amount of trifluoroacetyl chloride (CF3COCl) and trifluoroacetyl chloride (CF3COCl). Forms azeotropic or azeotrope-like compositions with iodomethane (CF3I) As used herein, the term "effective amount" refers to other The amount of each component that, when combined with the components, results in the formation of an azeotropic or azeotrope-like mixture.

[0039] The azeotropic or azeotrope-like composition is composed of trifluoroacetyl chloride (CF3COCl) and and trifluoroiodomethane (CF3I), or may consist essentially of a combination of Trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3 I) may be a combination of

[0040] 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 azeotropic or azeotrope-like ratios. and adding further components, provided that the further components do not form new azeotropic or azeotrope-like systems. For example, an azeotropic mixture consisting essentially of two compounds means that the two The components form an azeotrope, and the additional components do not render the mixture non-azeotropic, and the compounds Does not form an azeotrope with either one or both of them (e.g., does not form an azeotrope with three or more components) ), optionally containing one or more further ingredients.

[0041] The present disclosure also provides an effective amount of trifluoroacetyl chloride (CF3COCl) and trifluoroacetyl chloride (CF3COCl). Fluoroiodomethane (CF3I) can be mixed, combined, or blended The present invention provides a method for forming an azeotropic or azeotrope-like composition by combining two or more components. In addition, among the wide variety of methods known in the art for forming the composition, can be used in the present method, for example as part of a batch reaction. or as part of a continuous reaction and / or process, or of two or more such steps In combination, trifluoroacetyl chloride (CF3COCl) and trifluoroiodide methyl methyl fluoride (CF3I) by mixing, blending, or otherwise manually and / or It can be combined mechanically. Trifluoroacetyl chloride (CF3C OCl) and trifluoroiodomethane (CF3I) are both commercially available and several These components can be purchased from several different suppliers in the required amounts, e.g. The amount can be provided by measuring the amount of each component and then combining these amounts.

[0042] Azeotropic or azeotrope-like compositions have a viscosity of about -46°C at pressures of about 4.9 psia to about 348 psia. 0.0°C to about 90.0°C, and containing from about 0.5% by weight to about 99.0% by weight of trifluoromethylpropional. Acetyl chloride (CF3COCl) and about 1.0% to about 99.5% by weight of triflate consisting essentially of or consisting of iodomethane (CF3I).

[0043] Boiling point of about -46.0℃ to about 90.0℃ at pressure of about 4.9 psia to about 348 psia Azeotropic or azeotrope-like compositions having about 4.4 wt. %, 10.7 wt. %, 16.9 wt. % Amount%, 23.1% by weight, 29.3% by weight, 35.5% by weight, 41.9% by weight, 48.4% by weight Amount%, 55.1% by weight, 62.1% by weight, 69.7% by weight, 77.9% by weight, 87.3% by weight % by weight, or 99.0% by weight, or any range defined between any two of the foregoing values. Trifluoroacetyl chloride (CF3COCl) in the range of 89.5 wt.%, and about 95.6 wt.%. .3wt%, 83.1wt%, 76.9wt%, 70.7wt%, 64.5wt%, 58 .1wt%, 51.6wt%, 44.9wt%, 37.9wt%, 30.3wt%, 22 0.1% by weight, or 12.7% by weight, or any value defined between any two of the aforementioned values. or consisting essentially of any trifluoroiodomethane (CF3I) It may consist of these.

[0044] Further azeotropic compositions include those at a temperature of -46.0°C and a pressure of about 4.9 psia: , about 99.5% by weight trifluoroiodomethane (CF3I) and about 0.5% by weight trifluoroiodomethane (CF3I). Fluoroacetyl chloride (CF3COCl); temperature -40.0°C and pressure approximately 6.6ps ia, about 95.6 wt. % trifluoroiodomethane (CF3I) and about 4.4 % by weight of trifluoroacetyl chloride (CF3COCl); temperature -30.0°C and pressure About 89.3 wt. % trifluoroiodomethane (CF3I) at about 10.5 psia ) and about 10.7 wt. % trifluoroacetyl chloride (CF3COCl); About 83.1 wt. % trifluoroiodine at 0.0°C and a pressure of about 16.0 psia Methane (CF3I) and approximately 16.9 wt% trifluoroacetyl chloride (CF3CO Cl); about 76.9 wt. % of thiamin at a temperature of -10.0°C and a pressure of about 23.5 psia Trifluoroiodomethane (CF3I) and approximately 23.1% by weight of trifluoroacetylchloride Lithium (CF3COCl); at a temperature of 0.0°C and a pressure of about 33.7 psia, it is about 70. 7% by weight of trifluoroiodomethane (CF3I) and about 29.3% by weight of trifluoro Acetyl chloride (CF3COCl); at a temperature of 10.0°C and a pressure of approximately 46.9 psia In the present invention, about 64.5% by weight of trifluoroiodomethane (CF3I) and about 35.5% by weight of of trifluoroacetyl chloride (CF3COCl); at a temperature of 20.0°C and a pressure of about 63. About 58.1% by weight of trifluoroiodomethane (CF3I) at 9 psia and about 41.9% by weight of trifluoroacetyl chloride (CF3COCl); temperature 30.0°C and About 51.6 wt. % trifluoroiodomethane (C F3I) and about 48.4% by weight of trifluoroacetyl chloride (CF3COCl); About 44.9 wt. % trifluoroethylene at 40.0°C and a pressure of about 111.4 psia Iodomethane (CF3I) and approximately 55.1% by weight of trifluoroacetyl chloride (CF 3COCl); about 37.9 wt. at a temperature of 50.0°C and a pressure of about 143.5 psia % trifluoroiodomethane (CF3I) and about 62.1% by weight trifluoroacetyl chloride (CF3COCl); at a temperature of 60.0°C and a pressure of approximately 182.1 psia , about 30.3 wt. % trifluoroiodomethane (CF3I) and about 69.7 wt. % trifluoroiodomethane (CF3I). Trifluoroacetyl chloride (CF3COCl); temperature 70.0°C and pressure about 228.2 About 22.1 wt. % trifluoroiodomethane (CF3I) and about 7 psia 7.9 wt% trifluoroacetyl chloride (CFCOCl); temperature 80.0°C and About 12.7 wt. % trifluoroiodomethane (C F3I) and about 87.3% by weight of trifluoroacetyl chloride (CF3COCl); and about 1.0 wt. % triflate at a temperature of 90.0°C and a pressure of about 348.0 psia. Trifluoroiodomethane (CF3I) and approximately 99.0% by weight of trifluoroacetyl chloride (CF3COCl).

[0045] The azeotropic or azeotrope-like composition may contain from about 0.5% to about 25% by weight of trifluoroacetyl chloride (CF3COCl), about 2% by weight to about 21% by weight of trifluoroacetyl chloride Fluoroacetyl chloride (CF3COCl), about 14% by weight to about 18% by weight CF3COCl), one azeotrope contains about 14.87 wt.% trifluoroacetyl chloride. trifluoroiodomethane (CF3COCl), and about 75% to about 99.5% by weight of trifluoroiodomethane Fluoroisopropyl ether (CF3I), about 79% by weight to about 98% by weight of trifluoroiodomethane (CF3I), ), about 82% to about 86% by weight of trifluoroiodomethane (CF3I), one azeotrope The product consists essentially of about 85.13% by weight of trifluoroiodomethane (CF3I). The azeotropic or azeotrope-like composition may have a viscosity of about 14.41 ps. It has a boiling point of about -22.50°C ± 0.30°C at a pressure of ia ± 0.30 psia.

[0046] In other words, the azeotropic or azeotrope-like composition contains from about 0.5% to about 25% by weight of trifle. Trifluoroacetyl chloride (CF3COCl), about 75% to about 99.5% by weight Oloiodomethane (CF3I), or about 2% to about 21% by weight of trifluoroacetyl chloride (CF3COCl), about 79% to about 98% by weight of trifluoroiodomethane (CF3I), or about 14% to about 18% by weight of trifluoroacetyl chloride (CF 3COCl), and about 82% to about 86% by weight of trifluoroiodomethane (CF3I ), and in one azeotrope, about 14.87 wt. % trifluoroacetyl chloride (C F3COCl) and approximately 85.13% by weight of trifluoroiodomethane (CF3I). Azeotropic or azeotrope-like compositions may be of a molecular weight of about 1400 or more. It has a boiling point of approximately -22.50°C ± 0.30°C at a pressure of 0.41 psia ± 0.30 psia. do.

[0047] In other words, the azeotropic or azeotrope-like composition may be at least about 0.5 wt. %, at least about 2 wt. % , or about 14% by weight, or at most about 18%, about 21%, or about 25% by weight % by weight of trifluoroacetylacetonate, or any range defined between any two of the above values. fluorine chloride (CF3COCl), and at least about 75 wt.%, about 79 wt.%, or about 82% by weight, or at most about 86%, about 98%, or about 99.5% by weight; or trifluoroiodomethane within any range defined between any two of the above values The azeotropic composition consists essentially of, or consists of, about 14.87 wt. % and trifluoroacetyl chloride (CF3COCl) and about 85.13 wt.% trifluoroacetyl chloride (CF3COCl). The present disclosure also provides a method for preparing a catalyst comprising: The ebullient or azeotrope-like composition is approximately -22.5°C at a pressure of approximately 14.41 psia ± 0.30 psia. It has a boiling point of 50°C ± 0.30°C.

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

[0049] As disclosed herein, an effective amount of trifluoroacetyl chloride (CF COCl) and trifluoroiodomethane (CF3I), or an azeotropic or azeotrope-like composition thereof, is preferably trifluoroacetyl chloride (CF 3COCl) and / or trifluoroiodomethane (CF3I) to separate impurities One impurity that can be present in trifluoroiodomethane (CF3I) is The pure product is trifluoromethane (HFC-23).

[0050] Effective amounts of trifluoroacetyl chloride (CF3COCl) and trifluoroiodine Azeotropic or co-evaporative mixtures comprising, consisting essentially of, or consisting of methane (CF3I) Preparation of boiling-like compositions, for example, to remove impurities from trifluoroiodomethane (CF3I) The co-reaction product is used to obtain high-purity trifluoroiodomethane (CF3I) by removing Separation techniques such as boiling distillation become possible.

[0051] In particular, an effective amount of trifluoroacetyl chloride (CF3COCl) and trifluoro Azeotropic compounds comprising, consisting essentially of, or consisting of iodomethane (CF3I) Alternatively, the azeotrope-like composition may be trifluoroacetyl chloride (CF3COCl) and trifluoroacetyl chloride (CF3COCl). One or both of the following compounds are used: trifluoroacetyl chloride ( CF3COCl) and one or more other chemicals other than trifluoroiodomethane (CF3I) The compound may be formed from a composition that includes, for example, impurities. One example is trifluoromethane (HFC-23). ​​Azeotropic or azeotrope-like compositions After formation of the product, the azeotropic or azeotrope-like composition can be separated by a suitable method such as distillation, phase separation, or fractional distillation. Thus, it can be separated from other chemical compounds.

[0052] In one example, the present disclosure provides a method for producing a compound comprising the steps of: Trifluoroiodomethane (CF3I) containing acetyl chloride (CF3COCl) From the crude primary composition, trifluoroacetyl chloride (CF3COCl) as an impurity The method for separating impurities includes crude trifluoroiodomethane (CF3I), trifluoroiodomethane (TFI), and trifluoroacetyl chloride (CF3COCl), and at least one additional impurity Providing a primary composition, and an effective amount of trifluoroacetyl chloride (CF3CO Cl) and trifluoroiodomethane (CF3I), or and exposing the primary composition to conditions effective to form a secondary composition, the secondary composition being an azeotropic or azeotrope-like composition comprising: and separating the primary composition by a separation technique such as, for example, phase separation, distillation, or fractional distillation. The method further comprises the step of separating the secondary composition from the soluble solid. The resulting product may be subjected to an isolation or purification step to obtain purified trifluoroiodomethane (CF3I). stomach.

[0053] In another example, trifluoroiodomethane (CF3I) and trifluoroacetylchloride The present invention provides a composition comprising one of the following compounds: This composition may contain other trifluoroiodomethane (CF3I) and trifluoroisopropyl methyl acrylate (TFM). Fluoroacetyl chloride (CF3COCl) is added in a sufficient amount to form a composition Effective amounts of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) and subjecting the mixture to conditions useful for forming a product, followed by separation, such as, for example, phase separation, distillation, or fractional distillation. The azeotropic or azeotrope-like composition is then separated from the impurities by techniques. Azeotropy or azeotropy of fluoromethane (CF3I) and trifluoroacetyl chloride (CF3COCl) The azeotrope-like composition may be subjected to further separation or purification steps to produce purified trifluoroiodomethane (C F3I) may also be obtained.

[0054] In another example, discussed in detail in Example 3 below, the pressure sensitivity of the present azeotropic compositions is Fluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I ) by "pressure swing" distillation to separate the trifluoroacetyl chloride. Essentially pure trifluoroiodomethane (CF3COCl) and trifluoroiodomethane (CF3I) Such compositions can be formed.

[0055] Trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane ( CF3I) was converted to trifluoroacetyl chloride (CF3COCl) and trifluoroiodide One method for separating fluorinated methane (CF3I) from a primary composition containing fluorinated methane (CF3I) is to The bottom product is pure trifluoroacetyl. It may then be recovered from a low pressure column consisting essentially of chloride (CF3COCl). The first distillate is conveyed from the lower pressure column to the higher pressure column, wherein the first distillate is conveyed in an effective amount of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (C The second bottoms product is an azeotropic or azeotrope-like composition consisting essentially of pure HCl (F3I). It may be recovered from a high pressure column consisting essentially of trifluoroiodomethane (CF3I). The method further comprises, after the second recovery step, separating the second distillate from the high-pressure column from the primary composition. The method may further comprise the additional step of returning the resulting mixture to a feed stream containing the hydroxybenzoates.

[0056] Similarly, trifluoroacetyl chloride (CF3COCl) and trifluoroiodine Methane (CF3I) was reacted with trifluoroacetyl chloride (CF3COCl) and trifluoroacetyl chloride (CF3COCl). Another method for separating the primary composition containing iodomethane (CF3I) is to The first step involves conveying a feed stream containing fluorine-containing fluorine to a high-pressure column. The bottom product is pure trifluoroisopropyl fluorine. The first column may then be separated from the second column, which may then be separated from the first column. The first distillate is conveyed from the higher pressure column to the lower pressure column, where the first distillate is conveyed to the lower pressure column in an effective amount of Trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane (CF3 The second bottoms product is an azeotropic or azeotrope-like composition consisting essentially of trifle I). may be recovered from a low pressure column consisting essentially of chloroacetyl chloride (CF3COCl). The method further comprises, after the second recovery step, separating the second distillate from the low pressure column into a first composition. The method may further comprise the additional step of returning the resulting mixture to a feed stream containing the hydroxybenzoates.

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

[0058] Example 1 - Ebuliometer investigation Trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane ( An ebullometer was used to measure the azeotropic and azeotrope-like compositions of CF3I. The bryometer is a vacuum-jacketed glass vessel sealed at the bottom and open to the air at the top. The top of the ebullometer or the condenser jacket contained dry ice and ethanol. At a pressure of 14.4 psia, trifluoroacetyl chloride -20.2°C for CF3COCl, and -20.2°C for trifluoroiodomethane (CF3I) The temperature obtained was about -72°C, which is significantly lower than the saturation temperature of -22.4°C in the case of In this way, all the vapor in the system is condensed and refluxed to the ebullometer, and the liquid and vapor phases are in equilibrium. A quartz platinum thermometer with an accuracy of ±0.002°C was placed in the glass vessel. Insert a quartz platinum thermometer into the flask and measure the temperature of the condensed vapor corresponding to the equilibrium boiling point of the mixture. Boiling stones were used to help maintain smooth boiling of the mixture in the ebullometer. I helped.

[0059] The following procedure was used:

[0060] 1. Immerse a quartz thermometer in a long dewar containing an ice / water slurry until the thermometer registers 0°C. The dewar should be at least 3 / 4 the length of the thermometer shaft. The thermometer was deep enough that it was immersed in the ice / water. The resistance of the thermometer was recorded in ohms.

[0061] 2. Fill the condenser jacket 1 / 4 full with ethanol. The jacket of the condenser was cooled by introducing a sachet, and the ethanol was boiled and blown out. Avoided release and / or scattering.

[0062] 3. A known amount of trifluoroiodomethane (CF3I) or trifluoroacetyl chloride Lithium (CF3COCl) was added to the ebulliometer and brought to vigorous reflux. A data-equipped barometer was used to record the temperature and atmospheric pressure.

[0063] The measurement was carried out in two steps. First, gas chromatography (GC) Trifluoroiodomethane (C) with a purity of 99.88 area % as determined by Approximately 24.15 g of F3I) was first measured before and after addition using a balance with an accuracy of ±0.01 g. The liquid was brought to a boil and the recorded The equilibrium temperature of trifluoroiodomethane (CF3I) at atmospheric pressure was recorded. Trifluoroacetylacetonate with a purity of 98% area as determined by GC. A small amount of chloroform (CF3COCl) was introduced into the ebullometer, and the condensed liquid The equilibrium temperature of the mixture was recorded.

[0064] In the second step, 98% area purity was obtained as determined by gas chromatography (GC). Approximately 15.66 g of trifluoroacetyl chloride (CF3COCl) having a viscosity of ±0 Ebriometabolism was measured by weighing the container before and after addition using a balance with a precision of 0.01 g. The liquid was boiled and trifluoroacetyl chloride (C The equilibrium temperature of F3COCl was recorded. Trifluoroiodomethane (CF3I) with a purity of 99.88 area % as measured by An increasing amount of water was introduced into the ebulliometer and the equilibrium temperature of the condensed liquid mixture was recorded.

[0065] Combining the data from the first and second steps above, it was determined that an azeotrope was formed. The trifluoroacetyl chloroforms listed in Table 1 below show the minimum temperature at which Fluoride (CF3COCl) and trifluoroiodomethane (CF3I) are each 0 to 100 The composition range data in weight percent was completed and this data is also presented in graphical form in FIG. The bubble point temperature of the mixture remains constant, which means that the The mixture was shown to be azeotrope-like over a large composition range. [Table 1] Example 2 - Azeotropic Locus

[0066] EW Lemmon et al., "A Generalized Model for t he Thermodynamic Properties of Mixtures” , International Journal of Thermophysics, In Vol. 20, pp. 825-835 (1999), the authors accurately calculate the thermodynamic properties of mixtures. The proposed Helmholtz energy equation of state ( The Helmholtz Energy Equation of State (HEOS) is a method for determining the energy density of pure components and phases of a mixture. A mixed vaporizer used to identify the presence and composition of azeotropes, taking into account interaction parameters. Determine any thermodynamic quantity, including vapor and liquid equilibrium compositions. The set value was reduced to the HEOS interaction parameter given on page 828 of the above publication. After reduction, trifluoroiodomethane (CF3I) and trifluoroacetyl chloride ( Incorporating the thermodynamic properties of both pure components (CF3COCl) as well as the above-mentioned publications The vapor-liquid equilibrium composition is evaluated using the thermodynamic relationship described on pages 830-831 of the publication. It has been discovered that azeotropic compositions are generally sensitive to system temperature and pressure. .

[0067] For example, at the system pressure (14.4 psia) of the ebullionometer in Example 1, The composition was identified as about 85 wt. % CF3I. However, an increase of about 47 psia At the system pressure, the azeotropic composition is 65 wt.% trifluoroiodomethane (CF3 Without being bound by theory, the sensitivity of the azeotrope to the system conditions The reaction is carried out using trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3 COCl) as a function of different system conditions. Examination of the VLE of these components yields the azeotrope loci shown in Table 2. [Table 2] Example 3 - Pressure Swing Separation

[0068] The well-known consequence of an azeotrope is that it completely separates its components in a single distillation operation. For example, the azeotropic behavior described in Example 1 is 14.4 ps Trifluoroiodomethane (CF3I) and trifluoromethane (CF3I) by a distillation column supported by ia. Separation of a 50 / 50 wt% mixture of acetyl chloride (CF3COCl) with acetyl chloride (CF3COCl) yielded pure Trifluoroacetyl chloride (CF3COCl) (i.e., 0% by weight of trifluoroacetyl chloride) Iodomethane (CF3I)) end point and the minimum boiling point azeotropic composition (approximately 85 wt.% trifluoroiodine The boundary is defined by the composition between methyl methyl ether (Methyl methyl ether (CF3I)). Distillation of the mixture under these conditions yielded trifluoroiodomethane (C) in a purity of greater than 85% by weight. This fundamental barrier to azeotropy cannot be overcome to produce purer tetrahydrofurans (F3I). Trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COC To achieve both of these, different separation strategies must be implemented.

[0069] As described in Example 2, trifluoroiodomethane (CF3I) and trifluoroazolam were used. The azeotropic composition of the binary mixture with cetyl chloride (CF3COCl) varies with the system conditions. This sensitivity is greater than that achieved by pressure swing distillation. In this system, pressure sensitive azeotropes can be used to support good separation. , two distillations, one at any relatively low pressure and one at any relatively high pressure. The separation is carried out using columns in sequence. The columns are arranged so that the low pressure column is first in the sequence. Alternatively, the high pressure column may be first in the sequence. For purposes of this example, Referring to Figures 2 and 3, the columns are arranged in order with the low pressure column first.

[0070] Trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3C The mixture with HCl (OCl) is first subjected to distillation at low pressure. The specific composition of the mixture can be determined as needed. For purposes of this representative example, 50% by weight of trifluoroiodomethane is used. Fluorocarbon (CF3I) and 50% by weight of trifluoroacetyl chloride (CF3COCl) Referring now to FIG. 2, this mixture is referred to as Composition A ("Composition B"). Referring now to FIG. 3, the mixture flow 10 is fed to an optional low pressure ( For purposes of this example, the distillation column 12 is fed at a pressure of 20 psia.

[0071] As shown in Figure 2, composition A (stream 10 in Figure 3) has not yet reached the azeotropic point. Thus, the mixture may be concentrated in one component of the mixture and in an azeotropic or azeotrope-like composition. Here, the high-boiling component trifluoroacetyl chloride (C The fraction enriched with F3COCl) was collected as the bottom product and is shown in Figures 2 and 3. Composition "C" is referred to as Stream C, and is referred to as Stream 16 in FIG. 3. The composition is designated Composition B ("Composition "B") in Figures 2 and 3 and is shown in Figure 3 as a low pressure This mixture is then passed through stream 14 in Figure 3, followed by any of the distillates from column 12. It is passed through column 14 at high pressure (100 psia for the purposes of this example).

[0072] Referring now to FIG. 2, the point representing composition B on the high pressure curve is This allows the recovery of fractions enriched in other components of the mixture. In this example, trifluoroiodomethane (CF3I) is concentrated. The fraction that was removed was collected as the bottom product and is shown in Figures 2 and 3 as Composition D ("Composition "D" ') and is referred to as stream 20 in Figure 3. As with the low pressure column, the distillate is an azeotrope. This mixture is returned and mixed with composition A following flow 22 in FIG. You may do so.

[0073] In this way, the azeotropic barrier is determined by the sensitivity of its composition to column conditions. This is addressed by generating two streams enriched in both components. It is important to note that the column conditions and structure may vary depending on the context of the mixture. The composition is trifluoroiodomethane (CF3I) and / or trifluoroacetyl chloride. It can be designed to support almost any desired purity of (CF3COCl). Example 4 - Separation of impurities

[0074] In this example, one or more other impurities, such as trifluoromethane (HFC-23), Along with trifluoroacetyl chloride (CF3COCl) as an impurity, A crude composition of fluoroiodomethane (CF3I) is provided. The relative amounts of fluorine (CF3I) and trifluoroacetyl chloride (CF3COCl) were The composition may be modified if necessary to form the desired relative amounts, and the composition may be separated into two or more components from the remainder of the composition. Fluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl ) and are subjected to distillation under conditions useful for separating them. Fluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl ) as a light component, The remaining crude composition is then purified by the addition of trifluoroiodomethane (CF3I). The remaining crude composition of trifluoromethane (CF3I) was subjected to different temperature and pressure conditions. Other impurities such as HFC-23 are separated by further distillation to produce purified trifluoromethyl fluoride. Iodomethane (CF3I) can be obtained. Example 5 - Separation of impurities

[0075] In this example, trifluoroiodomethane (CF3I) and, e.g., trifluoro Compositions are provided that include at least one impurity, such as methane (HFC-23). The composition contains a sufficient amount of trifluoroacetyl chloride (CF3COCl) The composition is then mixed with an effective amount of trifluoroacetyl chloride (CF3COCl) and trifluoroacetyl chloride. Azeotropic or co-evaporative mixtures consisting essentially of or consisting of fluoroiodomethane (CF3I) and subjecting the mixture to conditions useful for forming a composition that is a boiling-like composition, followed by, for example, phase separation, distillation, The azeotropic or azeotrope-like composition is separated from the impurities by separation techniques such as distillation or fractional distillation. Then, trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3 The azeotropic or azeotrope-like composition of (COCl) may be subjected to further separation or purification steps to produce purified triflate Oloiodomethane (CF3I) may also be obtained. Example 6 - Separation of impurities

[0076] In this example, trifluoroacetyl chloride (CF3COCl) and e.g. Compositions containing at least one impurity, such as trifluoromethane (HFC-23), are provided. To this composition, trifluoroiodomethane (CF3I) is added in a sufficient amount, The composition comprises an effective amount of trifluoroacetyl chloride (CF3COCl) and trifluoroacetyl chloride (CF3COCl). Azeotropic or azeotrope-like compounds consisting essentially of or consisting of iodomethane (CF3I) The composition is subjected to conditions useful for forming the composition, followed by, for example, phase separation, distillation, or The azeotropic or azeotrope-like composition is separated from the impurities by a separation technique such as fractional distillation. Trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3CO The azeotropic or azeotrope-like composition of trifluoromethane (Cl) may be subjected to further separation or purification steps to form a purified trifluoromethane (Cl). Iodomethane (CF3I) may be obtained. Aspects

[0077] Aspect 1 comprises an effective amount of trifluoroacetyl chloride (CF3COCl) and trifluoroacetyl chloride (CF3COCl). Co-formulations comprising, consisting essentially of, or consisting of iodomethane (CF3I) It is an azeotropic or azeotrope-like composition.

[0078] In embodiment 2, the azeotropic or azeotrope-like composition is formed at a pressure of about 4.9 psia to 348 psia. 10. The azeotropic or azeotrope-like composition of claim 1, having a boiling point of about −46.0° C. to 90.0° C. be.

[0079] Aspect 3 is a method for preparing an azeotropic or azeotrope-like composition comprising from about 0.5% to about 99.0% by weight of trifluoromethane. Fluoroacetyl chloride (CF3COCl) and about 1.0% to about 99.5% by weight of 3. The azeotropic or azeotropic mixture of claim 1 or 2, consisting essentially of trifluoroiodomethane (CF3I). is an azeotrope-like composition.

[0080] Embodiment 4 is about 99.5 wt. % at a temperature of -46.0°C and a pressure of about 4.9 psia. of trifluoroiodomethane (CF3I) and about 0.5% by weight of trifluoroacetyl chlorine. It is an azeotropic composition containing benzoyl chloride (CF3COCl).

[0081] Embodiment 5 is about 95.6 wt. % at a temperature of -40.0°C and a pressure of about 6.6 psia. of trifluoroiodomethane (CF3I) and about 4.4% by weight of trifluoroacetyl chlorine. It is an azeotropic composition containing benzoyl chloride (CF3COCl).

[0082] Embodiment 6 is a 6000 psi (10.5 psia) 6000 psi (10.5 wt. oz) of 10.5 wt. % cellulose at a temperature of -30.0°C and a pressure of about 10.5 psia. % trifluoroiodomethane (CF3I) and about 10.7% by weight trifluoroacetyl It is an azeotropic composition containing benzoyl chloride (CF3COCl).

[0083] Embodiment 7 is a cellulose acetate solution of about 83.1 wt. % at a temperature of -20.0°C and a pressure of about 16.0 psia. % trifluoroiodomethane (CF3I) and about 16.9% by weight trifluoroacetyl It is an azeotropic composition containing benzoyl chloride (CF3COCl).

[0084] Embodiment 8 is a 76.9 wt. % cellulose ester at a temperature of -10.0°C and a pressure of about 23.5 psia. % trifluoroiodomethane (CF3I) and about 23.1% by weight trifluoroacetyl It is an azeotropic composition containing benzoyl chloride (CF3COCl).

[0085] Aspect 9 is a composition comprising about 70.7 wt. % of a cellulose acetate copolymer at a temperature of 0.0° C. and a pressure of about 33.7 psia. Trifluoroiodomethane (CF3I) and approximately 29.3% by weight of trifluoroacetyl chlorine It is an azeotropic composition containing benzoyl chloride (CF3COCl).

[0086] Embodiment 10 is a 64.5 wt. % cellulose ester at a temperature of 10.0° C. and a pressure of about 46.9 psia. % trifluoroiodomethane (CF3I) and about 35.5% by weight trifluoroacetyl It is an azeotropic composition containing benzoyl chloride (CF3COCl).

[0087] Embodiment 11 is a 58.1 wt. % cellulose ester at a temperature of 20.0° C. and a pressure of about 63.9 psia. % trifluoroiodomethane (CF3I) and about 41.9% by weight trifluoroacetyl It is an azeotropic composition containing benzoyl chloride (CF3COCl).

[0088] Embodiment 12 is a 51.6 wt. % cellulose acetate solution at a temperature of 30.0° C. and a pressure of about 85.1 psia. % trifluoroiodomethane (CF3I) and about 48.4% by weight trifluoroacetyl It is an azeotropic composition containing benzoyl chloride (CF3COCl).

[0089] Embodiment 13 is a 44.9 wt. % cellulose at a temperature of 40.0° C. and a pressure of about 111.4 psia. % by weight of trifluoroiodomethane (CF3I) and about 55.1% by weight of trifluoroacetone. It is an azeotropic composition containing methyl chloride (CF3COCl).

[0090] Embodiment 14 is a 37.9 wt. % cellulose at a temperature of 50.0° C. and a pressure of about 143.5 psia. % by weight of trifluoroiodomethane (CF3I) and about 62.1% by weight of trifluoroacetone. It is an azeotropic composition containing methyl chloride (CF3COCl).

[0091] Embodiment 15 is a 30.3 wt. % olefin copolymer at a temperature of 60.0° C. and a pressure of about 182.1 psia. % by weight of trifluoroiodomethane (CF3I) and about 69.7% by weight of trifluoroacetone. It is an azeotropic composition containing methyl chloride (CF3COCl).

[0092] Embodiment 16 is a 22.1 wt. % cellulose ester at a temperature of 70.0° C. and a pressure of about 228.2 psia. % by weight of trifluoroiodomethane (CF3I) and about 77.9% by weight of trifluoroacetone. It is an azeotropic composition containing methyl chloride (CF3COCl).

[0093] Embodiment 17 is a 12.7 wt. % sintered product at a temperature of 80.0° C. and a pressure of about 283.1 psia. % by weight of trifluoroiodomethane (CF3I) and about 87.3% by weight of trifluoroacetone. It is an azeotropic composition containing methyl chloride (CF3COCl).

[0094] Embodiment 18 is a 1.0 wt. % cellulose ester at a temperature of 90.0° C. and a pressure of about 348.0 psia. % trifluoroiodomethane (CF3I) and approximately 99.0% by weight trifluoroacetyl It is an azeotropic composition containing benzoyl chloride (CF3COCl).

[0095] Embodiment 19 is a method for preparing a fluororesin comprising about 0.5% to about 25% by weight of trifluoroacetyl chloride (CF 3COCl) and about 75% to about 99.5% by weight of trifluoroiodomethane (CF3 10. The azeotropic or azeotropic composition according to claim 1, comprising, consisting essentially of, or consisting of I). is an azeotrope-like composition.

[0096] Embodiment 20 is a method for preparing a fluororesin comprising about 2% to about 21% by weight of trifluoroacetyl chloride (CF3C OCl) and about 79% to about 98% by weight of trifluoroiodomethane (CF3I). 20. The azeotropic or azeotropic composition of claim 19, comprising, consisting essentially of, or consisting of: It is a similar composition.

[0097] Embodiment 21 is a fluoropolymer containing about 14% to about 18% by weight of trifluoroacetyl chloride (CF3 COCl) and about 82% to about 86% by weight of trifluoroiodomethane (CF3I) 21. The azeotropic or co-solvent composition of claim 20, comprising, consisting essentially of, or consisting of: It is a boiling-like composition.

[0098] Embodiment 22 is a fluoropolymer containing about 14.87% by weight of trifluoroacetyl chloride (CFCOCl ) and about 85.13% by weight of trifluoroiodomethane (CF3I), 22. The azeotropic or azeotrope-like composition of claim 21 consisting essentially of, or consisting of, .

[0099] Embodiment 23 is heated to about -22.50°C ± 0.30 psia at a pressure of about 14.41 psia ± 0.30 psia. 23. The azeotropic or azeotrope-like composition of any one of embodiments 19 to 22, having a boiling point of 0.30° C. It is a thing.

[0100] Embodiment 24 is a mixture of trifluoroacetyl chloride (CF3COCl) and trifluoroiodide. 19. The azeotropic composition of any one of aspects 1 to 18, consisting essentially of tetrahydrofuran (CFI). Or an azeotrope-like composition.

[0101] Embodiment 25 is a mixture of trifluoroacetyl chloride (CF3COCl) and trifluoroiodide. 19. The azeotropic or azeotropic composition according to any one of aspects 1 to 18, consisting of tetrahydrofuran (CFU) and tetrahydrofuran (CF3I). It is a similar composition.

[0102] Aspect 26 includes the azeotropic or azeotrope-like composition of any one of Aspects 1-18. A composition consisting essentially of or consisting of these.

[0103] Aspect 27 is directed to a method for preparing a zeotropic or azeotrope-like composition comprising at least about 5% by weight of the azeotropic or azeotrope-like composition. 27. The composition according to claim 26, wherein the composition consists of or consists of:

[0104] Embodiment 28 is directed to a method for preparing a zeotropic or azeotrope-like composition, comprising at least about 15% by weight of the azeotropic or azeotrope-like composition. 28. The composition of embodiment 27, consisting essentially of, or consisting of:

[0105] Aspect 29 is a method for preparing a zeotropic or azeotrope-like composition comprising at least about 50% by weight of the azeotropic or azeotrope-like composition. 29. The composition of embodiment 28, consisting essentially of, or consisting of:

[0106] Aspect 30 comprises at least about 70% by weight of an azeotropic or azeotrope-like composition. 30. The composition of embodiment 29, consisting essentially of, or consisting of:

[0107] Aspect 31 is a method for preparing a zeotropic or azeotrope-like composition comprising at least about 90% by weight of the azeotropic or azeotrope-like composition. A composition according to embodiment 30, consisting essentially of, or consisting of:

[0108] Embodiment 32 is a mixture of trifluoroacetyl chloride (CF3COCl) and trifluoroiodide. and HCl (CF3I) at pressures of approximately 4.9 psia and 348 psia. Trifluoroacetyl chloride having a boiling point of about -46.0°C to about 90.0°C (CF3COCl) and trifluoroiodomethane (CF3I), forming an azeotropic or azeotrope-like composition that is Or a method of forming an azeotrope-like composition.

[0109] Aspect 33 is a method for preparing a fluororesin comprising the steps of: combining a fluororesin containing from about 0.5% to about 99.0% by weight of trifluoroacetate; Trifluoromethane chloride (CF3COCl) and about 1.0% to about 99.5% by weight of trifluoromethane 33. The method of embodiment 32, comprising combining iodomethane (CF3I).

[0110] Embodiment 34 is a mixture of trifluoroacetyl chloride (CF3COCl) and trifluoroiodide. an effective amount of trifluoroacetyl chloride (CF Azeotropic or azeotrope-like compositions containing trifluoroiodomethane (CF3I) and trifluoroiodomethane (CF3I) A method for forming an azeotropic or azeotrope-like composition comprising the steps of:

[0111] Embodiment 35 is a mixture of trifluoroacetyl chloride (CF3COCl) and trifluoroiodide. 18. The azeotropic or azeotrope-like composition of any of the embodiments 1-18 can be prepared by combining tetrahydrofuran (CFU) and tetrahydrofuran (CF3I). 35. The method of embodiment 34, comprising forming an article.

[0112] Embodiment 35 is trifluoroacetyl chloride (CF3COCl), trifluoroiodide trifluoromethane (CF3I) from a primary composition containing trifluoromethane (CF3I), and at least one impurity Separation of acetyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) 1. A method for preparing a primary composition comprising: an effective amount of trifluoroacetyl chloride ( CF3COCl) and trifluoroiodomethane (CF3I), forming a secondary composition which is an azeotropic or azeotrope-like composition consisting of or consisting of the secondary composition; and separating the product from the primary composition and at least one impurity.

[0113] In a thirty-sixth embodiment, the forming step comprises providing from about 0.5% to about 99.0% by weight of the toner in the primary composition. Trifluoroacetyl chloride (CF3COCl) from about 1.0% to about 99.5% by weight trifluoroiodomethane (CF3I) 36. The method of claim 35, further comprising forming a secondary composition, the secondary composition being an azeotropic or azeotrope-like composition comprising: This is the method described above.

[0114] Embodiment 37 is directed to a method for preparing an azeotropic or azeotrope-like composition, wherein the azeotropic or azeotrope-like composition is as defined in any one of embodiments 1-18. The method according to embodiment 35 or 36,

[0115] Embodiment 38 performs the separation by at least one of phase separation, distillation, and fractional distillation. 37. The method according to claim 35 or 36,

[0116] Embodiment 39 is a mixture of trifluoroacetyl chloride (CF3COCl) and trifluoroiodide. Trifluoromethane (CF3I) was reacted with trifluoroacetyl chloride (CF3COCl), trifluoromethane (CF3COCl), A primary composition containing fluoroiodomethane (CF3I) and at least one impurity 1. A method for isolating a compound comprising: Fluoride (CF3COCl) and trifluoroiodomethane (CF3I) from these forming a secondary composition that is an azeotropic or azeotrope-like composition consisting essentially of, or consisting of, and separating the secondary azeotropic or azeotrope-like composition from the primary composition and at least one impurity. and

[0117] Embodiment 40 is directed to a method for preparing an azeotropic or azeotrope-like composition, wherein the azeotropic or azeotrope-like composition is as defined in any one of embodiments 1-18. 39. The method according to claim 39, wherein

[0118] Embodiment 41 performs the separation by at least one of phase separation, distillation, and fractional distillation. 41. The method according to claim 39 or 40,

[0119] Embodiment 42 is trifluoroacetyl chloride (CF3COCl) or trifluoroiodide 1. A method for the preparation of a fluoromethane (CF3I) comprising the steps of: This method uses trifluoroiodomethane (CF3I) and trifluoroacetyl chloride. and (CF3COCl) together with at least one impurity. and other processes using trifluoroiodomethane (CF3I) and trifluoroacetyl chloride. adding a sufficient amount of trifluoroacetate (CF3COCl) to the composition; and essentially from methyl chloride (CF3COCl) and trifluoroiodomethane (CF3I) useful for forming compositions which are azeotropic or azeotrope-like compositions consisting of or and separating the azeotropic or azeotrope-like composition from impurities. It is the law.

[0120] Aspect 43 is a method for preparing an azeotropic or azeotrope-like composition as defined in any one of aspects 1-18. The method according to embodiment 42, wherein

[0121] Embodiment 44 performs the separation by at least one of phase separation, distillation, and fractional distillation. 44. The method according to claim 42 or 43,

[0122] Embodiment 45 is a mixture of trifluoroacetyl chloride (CF3COCl) and trifluoroiodide. Trifluoromethane (CF3I) was reacted with trifluoroacetyl chloride (CF3COCl) and trifluoromethane (CF3COCl). The method includes a method for separating fluoroiodomethane (CF3I) from a primary composition containing fluoroiodomethane (CF3I), The method includes conveying a feed stream containing a primary composition to a low pressure column, and a first bottoms product. A first column from the low pressure column consisting essentially of fluoroacetyl chloride (CF3COCl) recovering a bottoms product; and azeotropic or azeotrope-like compositions consisting essentially of fluoroisopropyl ether (F3I) and trifluoroiodomethane (CF3I) a first distillate comprising, consisting essentially of, or consisting of the above-mentioned compounds from the low pressure column; from the column to a high pressure column, and and recovering a second bottoms product from the high-pressure column.

[0123] Embodiment 46 further comprises, after the second recovery step, separating the second distillate from the high-pressure column into a first composition. 46. ​​The method of embodiment 45, further comprising the additional step of returning the

[0124] Embodiment 47 is a mixture of trifluoroacetyl chloride (CF3COCl) and trifluoroiodide. Trifluoromethane (CF3I) was reacted with trifluoroacetyl chloride (CF3COCl) and trifluoromethane (CF3COCl). The method includes a method for separating fluoroiodomethane (CF3I) from a primary composition containing fluoroiodomethane (CF3I), conveying a feed stream containing a primary composition to a high-pressure column; recovering a first bottoms product from the higher pressure column, the first bottoms product consisting essentially of (CF3I); , an effective amount of trifluoroacetyl chloride (CF3COCl) and trifluoroiodomethane azeotropic or azeotrope-like compositions consisting essentially of tungsten (CF3I), conveying a first distillate consisting of, or consisting of, from the higher pressure column to the lower pressure column; , the second bottom product is essentially trifluoroacetyl chloride (CF3COCl) and recovering a second bottoms product from the lower pressure column.

[0125] Embodiment 48 further comprises, after the second recovery step, separating the second distillate from the low-pressure column into a primary composition. 48. The method of embodiment 47, further comprising the additional step of returning the

[0126] As used herein, "any value defined between any two of the preceding values" means any value between two of the preceding values. The phrase "within the range" means that the values ​​may be in a lower part of the list or in a higher part of the list. Any range, whether in For example, a pair of values ​​can be selected from two lower values, two It may be selected from the higher value, or the lower and higher values.

[0127] As used herein, the singular forms "a," "an," and "the" are used where the context requires. Furthermore, the term "quantity," "concentration," or other value or is a parameter that can be expressed as a range, a preferred range, or a sequence of upper and lower preferred values. When a range is given as one of the following, this does not apply whether the range is separately disclosed. Regardless, any upper range or upper preferred value and any lower range or lower preferred value and .sup.2.2.2.1 are to be understood as specifically disclosing all ranges formed from any pairing of .sup.2.2.1 and .sup.2.3.2.2.1.2.1.2.2.1 ... Where ranges of numerical values ​​are recited herein, unless otherwise stated, the ranges are It is intended to include the endpoints thereof, and all integers and fractions within the range. However, it is not intended to be limited to the specific values ​​recited when defining a range.

[0128] 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. The present invention includes the following aspects. [1] An effective amount of trifluoroacetyl chloride (CF 3 COCl) and trifluoroiodomethane (CF 3 I). [2] 2. The composition of claim 1, wherein the azeotropic or azeotrope-like composition has a boiling point of about −46.0° C. to 90.0° C. at a pressure of about 4.9 psia to 348 psia. [3] The azeotropic or azeotrope-like composition is from about 0.5% to about 99.0% by weight of trifluoroacetyl chloride (CF 3 COCl) and about 1.0% by weight to about 99.5% by weight of trifluoroiodomethane (CF 3 1. The composition of claim 1, consisting essentially of I). [4] 2. The composition of claim 1, wherein the azeotropic 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. [5] The azeotropic or azeotrope-like composition is from about 0.5% to about 25% by weight of trifluoroacetyl chloride (CF 3 COCl) and about 75% to about 99.5% by weight of trifluoroiodomethane (CF 3 1. The composition of claim 1, consisting essentially of I). [6] The azeotropic or azeotrope-like composition is from about 2% to about 21% by weight of trifluoroacetyl chloride (CF 3 COCl) and about 79% to about 98% by weight of trifluoroiodomethane (CF 3 1. The composition of claim 1, consisting essentially of I). [7] The azeotropic or azeotrope-like composition is about 14% to about 18% by weight of trifluoroacetyl chloride (CF 3 COCl) and about 82% to about 86% by weight of trifluoroiodomethane (CF 3 1. The composition of claim 1, consisting essentially of I). [8] A method for forming an azeotropic or azeotrope-like composition comprising the steps of: 3 COCl) and trifluoroiodomethane (CF 3 I) to produce trifluoroacetyl chloride (CF), which has a boiling point of about -46.0°C to 90.0°C at pressures of about 4.9 psia and 348 psia. 3 COCl) and trifluoroiodomethane (CF 3 forming an azeotropic or azeotrope-like composition consisting essentially of I). [9] The combining step comprises about 0.5% by weight to about 99.0% by weight of trifluoroacetyl chloride (CF 3 COCl) and about 1.0% by weight to about 99.5% by weight of trifluoroiodomethane (CF 3 9. The method according to claim 8, comprising combining I).

[10] Trifluoroacetyl chloride (CF 3 COCl), trifluoroiodomethane (CF 3 I), and at least one impurity from a primary composition containing trifluoroacetyl chloride (CF 3 COCl) and trifluoroiodomethane (CF 3 I) A method for separating the compound I, comprising the steps of: Within the primary composition, an effective amount of trifluoroacetyl chloride (CF) having a boiling point of about −46.0° C. to 90.0° C. at a pressure of about 4.9 psia to 348 psia 3 COCl) and trifluoroiodomethane (CF 3 forming a secondary composition, which is an azeotropic or azeotrope-like composition consisting essentially of I); and separating the secondary composition from the primary composition and the at least one impurity.

Claims

1. 0.5% to 35.5% by weight of trifluoroacetyl chloride (CF ３ COCl) and 64.5% to 99.5% by weight of trifluoroiodomethane (CF ３ I). An azeotropic or azeotrope-like composition comprising:

2. 10. The azeotropic or azeotrope-like composition of claim 1 having a boiling point of from -46.0°C to 10.0°C at a pressure of from 4.9 psia to 46.9 psia.

3. 0.5% to 10.7% by weight of trifluoroacetyl chloride (CF ３ COCl) and 89.3% to 99.5% by weight of trifluoroiodomethane (CF ３ 2. The azeotropic or azeotrope-like composition of claim 1, consisting of: I).

4. 10. The azeotropic or azeotrope-like composition of claim 1 having a boiling point of −22.50° C.±0.30° C. at a pressure of 14.41 psia±0.30 psia.

5. 0.5% to 25% by weight of trifluoroacetyl chloride (CF ３ COCl) and 75% to 99.5% by weight of trifluoroiodomethane (CF ３ 2. The azeotropic or azeotrope-like composition of claim 1, comprising: I).

6. 2% to 21% by weight of trifluoroacetyl chloride (CF ３ COCl) and 79% to 98% by weight of trifluoroiodomethane (CF ３ 2. The azeotropic or azeotrope-like composition of claim 1, consisting of: I).

7. 14% to 18% by weight of trifluoroacetyl chloride (CF ３ COCl) and 82% to 86% by weight of trifluoroiodomethane (CF ３ 2. The azeotropic or azeotrope-like composition of claim 1, consisting of: I).

8. A method for forming an azeotropic or azeotrope-like composition comprising the steps of: ３ COCl) and trifluoroiodomethane (CF ３ I) to form the azeotropic or azeotrope-like composition of any of claims 1-7.

9. Trifluoroacetyl chloride (CF ３ COCl), trifluoroiodomethane (CF ３ I), and at least one impurity from a primary composition comprising trifluoroacetyl chloride (CF ３ COCl) and trifluoroiodomethane (CF ３ I) a method for separating the compound I, comprising the steps of: forming a secondary composition within the primary composition, the secondary composition being an azeotropic or azeotrope-like composition according to any one of claims 1 to 7; and separating the secondary composition from the primary composition.

10. The composition according to any one of claims 1 to 7 is used to treat trifluoroiodomethane (CF ３ I).

11. The method according to any one of claims 8 to 9, comprising the step of producing trifluoroiodomethane (CF ３ I).

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