Processing method for producing trifluoroiodomethane and trifluoroacetyl iodide

Abstract

To provide a gas-phase process for producing trifluoroiodomethane.SOLUTION: The process comprises: providing a reactant stream comprising hydrogen iodide and at least one trifluoroacetyl halide selected from the group consisting of trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof; reacting the reactant stream in the presence of a catalyst at a first reaction temperature of 25°C to 180°C to produce an intermediate product stream comprising trifluoroacetyl iodide; and reacting the intermediate product stream at a second reaction temperature of 200°C to 600°C to produce a final product stream comprising the trifluoroiodomethane. In the step of reacting the reactant stream, the reactant stream is in contact with the first catalyst for a contact time of 0.1 seconds to 300 seconds.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present disclosure relates to the use of trifluoroiodomethane (CF3I) and trifluoroacetyl iodine Specifically, the present disclosure relates to a process for producing triflate (CF3COI). Vapor Phase Processing Method for Producing Trifluoroiodomethane and Trifluoroacetyl Iodide - Patent application Regarding. [Background technology]

[0002] Trifluoroacetyl iodide (CF3COI) is a fluoroisotope of trifluoroiodomethane (C It is a compound that can be converted into perfluoromethyl iodide, trifluoromethyl iodide, Trifluoroiodide, also known as iodomethyl iodide or iodotrifluoromethane CHCl (CF3I) is useful in commercial applications, for example, as a refrigerant or fire suppressant. Trifluoroiodomethane is a compound with negligible ozone depletion potential. Trifluoroiodomethane is a molecule with low global warming potential that is more environmentally harmful. Materials can be substituted.

[0003] Methods for preparing trifluoroacetyl iodide are known. eactions of Metallic Salts of Acids with Halogens.Part I.The Reaction of Metal T rifluoroacetates with Iodine,Bromine,and Chlorine”,RNHaszeldine,Journal of the Chemical Society, pp. 584-587 (1951) A method for producing trifluoroacetyl iodide in approximately 62% yield without trifluoroacetyl chloride The batch reaction of water with hydrogen iodide without catalyst at 120°C for 8 hours is described. Low yield and long reaction times make it rather inefficient.

[0004] U.S. Patent No. 7,196,236 (Mukhopadhyay et al.) discloses a method for producing an iodine source, a small amount of which is at least a stoichiometric amount of oxygen, and the reactant CF3R (where R is -COOH, -COX, -CHO, -COOR2, and -SO2X, wherein R2 is an alkyl group; a trifluoromethyl group, and X is chlorine, bromine, or iodine) A catalytic process for producing iodomethane is disclosed. Hydrogen fluoride is oxidized with at least a stoichiometric amount of oxygen and is economically recyclable. It is possible to produce water and iodine.

[0005] U.S. Pat. No. 7,132,578 (Mukhopadhyay et al.) also discloses trifles. A catalytic process for the production of trifluoroiodomethane from iodoacetyl chloride However, the iodine source is iodine fluoride (IF). In contrast to hydrogen fluoride, iodine fluoride is relatively unstable and above 0 °C, it is more stable than I2 and I Iodine fluoride also decomposes into F5 if it is not available in commercially useful quantities. There is.

[0006] Some known methods for preparing trifluoroacetyl iodide include liquid phase processes. Liquid phase processes require a solvent that must be separated and disposed of. The additional steps required for separation and disposal reduce the efficiency of the process.

[0007] Therefore, it is possible to produce commercial quantities of trifluoroiodomethane from relatively inexpensive raw materials. There is a need to develop more efficient processes that can be scaled to accommodate these needs. Summary of the Invention

[0008] The present disclosure relates to the use of trifluoroiodomethane (CF3I) and trifluoroacetyl iodine A vapor-phase process for producing CF3COI is provided.

[0009] In one embodiment, the present invention provides a vapor phase process for producing trifluoroiodomethane. The treatment method involves the use of hydrogen iodide, trifluoroacetyl chloride, trifluoro trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof and at least one trifluoroacetyl halide selected from the group consisting of: and subjecting the reactant stream to a first reaction in the presence of a first catalyst at a temperature of from about 25° C. to about 400° C. reacting at a temperature to produce an intermediate product stream comprising trifluoroacetyl iodide; reacting the intermediate product stream in the presence of a second catalyst at a second reaction temperature of about 200°C to about 600°C; to produce a final product stream comprising trifluoroiodomethane.

[0010] In another embodiment, the present invention provides a vapor phase method for producing trifluoroacetyl iodide. The treatment method is a method for treating iodine containing hydrogen iodide, trifluoroacetyl chloride, trifluoroacetyl chloride, and iodine. Fluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof and at least one trifluoroacetyl halide selected from the group consisting of providing a reactant stream; and reacting the reactant stream at about 25°C to about 400°C in the presence of a first catalyst. reacting at temperature to produce a product stream comprising trifluoroacetyl iodide; include.

[0011] In another embodiment, the present invention provides a method for producing a fluororesin comprising at least 98% by weight of trifluoroacetyl iodine. chlorotrifluoroethane, trifluoroacetyl chloride, iodotrifluoro Methane, trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid a total of about 1 ppm to about 2 ppm selected from the group consisting of chlorotrifluoromethane, and 0,000 ppm (about 2% by weight) of a compound.

[0012] In another embodiment, the present invention provides a method for producing a fluoropolymer comprising at least 99% by weight of trifluoroiodomethane and , 1 ppm to 500 ppm of chlorotrifluoroethane and less than 500 ppm of hexafluoropropane Fluoroethane, less than 500 ppm trifluoromethane, and less than 100 ppm monoxide Carbon, less than 1 ppm hydrogen chloride, trifluoroacetyl fluoride, hexafluoro Propanone, trifluoroacetaldehyde, and trifluoroacetyl chloride and a total of 1 ppm to 500 ppm of compounds selected from the group consisting of: do.

[0013] In another embodiment, the present invention provides a vapor phase process for producing trifluoroiodomethane. The process provides a reactant stream comprising trifluoroacetyl iodide. The reaction stream is reacted in the presence of a catalyst at a reaction temperature of about 200°C to about 600°C. and producing a product stream comprising trifluoroiodomethane.

[0014] By reference to the following description of the embodiments in light of the accompanying drawings, the present invention These and other features of the disclosure, and the manner in which they are achieved, will become more apparent and better understood. It will be understood. [Brief explanation of the drawings]

[0015] [Figure 1] FIG. 1 is a process flow diagram showing a vapor phase process for producing trifluoroacetyl iodide.

[0016] [Figure 2] FIG. 1 is a process flow diagram showing a two-step vapor phase process for producing trifluoroiodomethane.

[0017] [Figure 3] FIG. 1 is a process flow diagram showing a vapor phase process for producing trifluoroiodomethane from trifluoroacetyl iodide. DETAILED DESCRIPTION OF THE INVENTION

[0018] The present disclosure provides a method for producing a compound containing hydrogen, iodine, and trifluoroacetyl halide (trifluoroacetyl Starting from trifluoromethyltrifluoromethyl chloride, etc., the process yields are surprisingly good. The present invention provides a process for producing fluoromethane and trifluoroacetyl iodide. The activating materials are relatively inexpensive and readily available in commercial quantities. , Commercial-scale production of trifluoroiodomethane and trifluoroacetyl iodide The disclosed gas phase processing method does not require a solvent. and further enhance their commercial appeal.

[0019] As disclosed herein, trifluoroiodomethane and trifluoroacetyl Iodides are hydrogen iodide (HI) and trifluoroacetyl halide (CF3COX, X =Cl, Br or F) from a reactant stream containing hydrogen iodide and trifluoroacetate. The trifluoroacetyl halide is anhydrous. Any water in the reactant stream may be added to the trifluoroacetyl halide. Part of the fluorine-containing iodide is hydrolyzed to give the more thermodynamically advantageous fluorine-containing iodide rather than the desired trifluoroacetyl iodide. As little water as possible should be present in the reactant stream, as this can form beneficial trifluoroacetic acid. It is preferable.

[0020] Anhydrous hydrogen iodide is substantially free of water, i.e., any water in anhydrous hydrogen iodide is about 500 parts per million by weight, about 300 ppm, about 200 ppm, about 100 ppm, and about 50 ppm, about 30 ppm, about 20 ppm, about 10 ppm, about 5 ppm, about 3 ppm, about 2 ppm, or less than about 1 ppm, or two or more of any of the preceding values. Preferably, the anhydrous hydrogen iodide is in an amount less than about 100 More preferably, the anhydrous hydrogen iodide contains less than about 10 ppm by weight of water. Most preferably, the anhydrous hydrogen iodide contains less than about 1 ppm by weight of water. Includes.

[0021] The reactant stream is substantially free of oxygen, i.e., any oxygen in the reactant stream is by weight Ratio: about 500 parts per million, about 300 ppm, about 200 ppm, about 100 ppm, about 50 ppm m, approx. 30ppm, approx. 20ppm, approx. 10ppm, approx. 5ppm, approx. 3ppm, approx. 2ppm or less than about 1 ppm, or between any two of the preceding values. Preferably, the amount of oxygen by weight in the reactant stream is less than about 1 More preferably, the amount of oxygen by weight in the reactant stream is less than about 10 ppm. Most preferably, the amount of oxygen by weight in the reactant stream is less than about 1 ppm. Before hydrogen iodide can react to form trifluoroacetyl iodide, the reaction Any oxygen in the stream may oxidize at least a portion of the hydrogen iodide to form iodine and water. Therefore, it is preferable to have as little oxygen as possible in the reaction stream. Even if both are carried out, the water formed will hydrolyze the trifluoroacetyl halide and The more thermodynamically favored trifluoroacetic acid is formed rather than the desired trifluoroiodomethane. This can reduce the efficiency of the process.

[0022] The at least one trifluoroacetyl halide is trifluoroacetyl fluoride. Trifluoroacetyl chloride (CF3COF), trifluoroacetyl chloride (CF3COCl), trifluoro acetyl bromide (CF3COBr), and any combination thereof. Preferably, the at least one trifluoroacetyl halide is selected from the group consisting of trifluoroacetyl halide, ... More preferably, it contains at least one trifluoroacetyl chloride. The amide consists essentially of trifluoroacetyl chloride. Most preferably, the amide consists essentially of at least Another type of trifluoroacetyl halide is trifluoroacetyl chloride.

[0023] For example, trifluoroacetyl chloride can be obtained from, for example, Sigma-Aldrich Corp. (St. Louis, Missouri), Halocarbon Prod. ucts Corporation(Peachtree Corners,George) ia), or commercially available from Solvay SA (Brussels, Belgium). Hydrogen iodide is commercially available or can be prepared by, for example, using elemental iodine. by reacting it with hydrazine, by distillation from a solution of sodium iodide and phosphoric acid, or was achieved by irradiating a mixture of hydrogen and iodine elements with radiation at a wavelength of approximately 578 nanometers. Therefore, it may be manufactured.

[0024] In the reactant stream, the molar ratio of hydrogen iodide to trifluoroacetyl halide is, for example, For example, about 0.1:1, about 0.2:1, about 0.3:1, about 0.4:1, about 0.5:1, about 0. 6:1, approx. 0.7:1, approx. 0.8:1, approx. 0.9:1, approx. 0.95:1, approx. 0.99:1 , or as low as about 1:1, or about 1.01:1, about 1.05:1, about 1.1:1, Approximately 1.2:1, approximately 1.3:1, approximately 1.4:1, approximately 1.5:1, approximately 1.6:1, approximately 1.8: 1, about 2.0:1, about 4.0:1, about 6.0:1, about 8.0:1, or about 10.0: 1 or higher, or about 0.1:1 to 10.0:1, about 0.2:1 to 8.0:1, about 0.3 :1~6.0:1, approx. 0.4:1~4.0:1, 0.5:1~2.0:1, approx. 0.6:1 ~1.2:1, approx. 0.7:1~1.0:1, approx. 0.1:1~2.0:1, approx. 0.5:1~ 1.5:1, approx. 0.6:1 to 1.4:1, approx. 0.7:1 to 1.3:1, approx. 0.8:1 to 1 0.2:1, approx. 0.9:1 to 1.1:1, approx. 0.95:1 to 1.05:1, approx. 0.99:1 ~1.01:1, about 1:1 to 2:1, about 0.8:1 to 1.5:1, or about 0.95: Within any range defined between any two of the preceding values, such as 1 to 1.2:1. Preferably, the molar ratio of hydrogen iodide to trifluoroacetyl halide is about 0. The ratio of hydrogen iodide to trifluoroacetylacetonate may be from about 0.5:1 to about 2.0:1. The molar ratio of iodine to iodine halide may be from about 0.6:1 to about 1.2:1. The molar ratio of hydrogen fluoride to trifluoroacetyl halide is about 0.7:1 to about 1.0:1. could be.

[0025] The trifluoroacetyl halide and hydrogen iodide forming the reactant stream enter the reactor The reactant streams may be preheated individually or together beforehand. ℃, about 30℃, about 40℃, about 50℃, about 60℃, or about 70℃, or At a high temperature of about 80°C, about 90°C, about 100°C, about 110°C, or about 120°C, or at 30℃~approx. 120℃, approx. 40℃~approx. 110℃, approx. 50℃~approx. 100℃, approx. 60℃~approx. 90℃ °C, or between any two of the aforementioned values, such as about 70°C to about 80°C. The reactant stream may be preheated to any temperature within the range. Preferably, the reactant stream is preheated to a temperature between about 40°C and about 120°C. More preferably, the reactant stream is preheated to a temperature of from about 60°C to about 110°C. Most preferably, the reactant stream is preheated to a temperature of about 80° C. to about 100° C. .

[0026] The hydrogen iodide and trifluoroacetyl halide in the reactant stream are reacted in the first reactor. In response, trifluoroacetyl iodide (CF3COI) and at least Both produce an intermediate product stream that includes a hydrogen halide (HX) by-product. Equation 1: HI + CF3COX → CF3COI + HX. The at least one hydrogen halide is hydrogen fluoride (HF), hydrogen chloride (HCl), and and hydrogen bromide (HBr).

[0027] The first reactor may be made of stainless steel, nickel, and / or nickel alloys (nickel-clad). chromium alloy, nickel-molybdenum alloy, nickel-chromium-molybdenum alloy, or nickel The first reactor may be a heated tube reactor including tubes made of a metal such as a copper-copper alloy. The tubes in the reactor may be heated. The first reactor may be any type of packed bed reactor. good.

[0028] The hydrogen iodide and trifluoroacetyl halide in the reactant stream are contained in the first reactor. The reaction occurs in the presence of a first catalyst containing activated carbon, mesocarbon, stainless steel, etc. Stainless steel, nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy, nickel - Copper alloys, copper, alumina, platinum, palladium, or carbides (iron carbide, molybdenum carbide) and metallic carbides such as nickel carbide, and non-metallic carbides such as silicon carbide), or The first catalyst may comprise a mesh, a palladium or a mixture thereof contained within the first reactor. The first catalyst may be in the form of a sphere or a sphere having an average diameter ranging from about 1 mm to about 25 mm. The diameter may be 0.05 mm or less.

[0029] When the first catalyst comprises platinum and / or palladium, the first catalyst is platinum and / or palladium on a support. The support of the first catalyst may be in the form of alumina or carbon. The amount of platinum and / or palladium on the support may be determined by the ratio of the platinum and / or palladium to the support. as a percentage of the total combined weight, for example, about 0.01 weight percent (wt%), about 0.1% by weight, approximately 0.3% by weight, approximately 0.5% by weight, approximately 0.7% by weight, approximately 1% by weight, approximately 2 weight% %, or even as little as about 3% by weight, or about 4%, about 5%, about 6%, about 8% by weight, or as much as about 10% by weight, or from about 0.01% by weight to about 10% by weight, About 0.1% to about 10% by weight, about 0.5% to about 8% by weight, about 1% to about 6% by weight , about 2% to about 5% by weight, about 3% to about 4% by weight, about 2% to about 3% by weight, or about Any range defined between any two of the preceding values, such as 0.5% by weight to about 5% by weight. Preferably, the amount of platinum and / or palladium on the support is about 0.1 % by weight to about 1% by weight of platinum and / or palladium on the support. The amount can be from about 0.3% to about 0.7% by weight. Most preferably, the platinum and / or the amount of palladium may be about 0.5% by weight.

[0030] Preferably, the first catalyst is selected from the group consisting of activated carbon, mesocarbon, stainless steel, platinum on a support, Palladium on a support or carbides (metallic carbides and non-metallic carbides such as silicon carbide) etc.), or a combination thereof. More preferably, the first catalyst comprises a platinum on a support. , palladium on a support, activated carbon, silicon carbide, or combinations thereof. Alternatively, the first catalyst includes activated carbon or silicon carbide.

[0031] Alternatively, the first catalyst may consist of the surface of the first reactor itself that contacts the reactant stream. The surface may provide a catalytic effect without the need for an additional catalyst.

[0032] The reactant flow may be, for example, about 0.1 seconds, 0.5 seconds, about 1 second, about 2 seconds, about 3 seconds, about 5 seconds, about For a short contact time of about 8 seconds, about 10 seconds, about 12 seconds, or about 15, about 18 seconds, or for a short contact time of about 20 seconds seconds, about 25 seconds, about 30 seconds, about 35 seconds, about 40 seconds, about 50 seconds, about 60 seconds, about 80 seconds, for a long contact time of about 300 seconds, or from about 0.1 seconds to about 300 seconds, or from about 0.5 seconds to about 80 seconds , about 1 second to about 60 seconds, about 5 seconds to about 50 seconds, about 8 seconds to about 40 seconds, about 10 seconds to about 35 seconds, about 1 2 seconds to about 30 seconds, about 15 seconds to about 25 seconds, about 18 seconds to about 20 seconds, about 10 seconds to about 40 seconds, or Any range defined between any two of the above values, such as approximately 10 seconds to approximately 30 seconds The reactant stream may be in contact with the first catalyst for any contact time within about 5 minutes. The reactant stream may be contacted with the first catalyst for a contact time of from about 10 seconds to about 60 seconds. The reactants may be contacted with the first catalyst for a contact time of about 10 seconds to about 40 seconds. The stream may be contacted with the first catalyst for a contact time of from about 15 seconds to about 35 seconds.

[0033] The reaction may be carried out at, for example, about atmospheric pressure, about 5 psig (34 kPaG), about 10 psig (69 kPaG), approximately 15 psig (103 kPaG), approximately 20 psig (138 kPaG), Approximately 25 psig (172 kPaG), approximately 30 psig (207 kPaG), approximately 35 psi g (241 kPaG), or about 40 psig (276 kPaG) for the first reaction operation. Operating pressure, or about 50 psig (345 kPaG), about 60 psig (414 kPaG) , approximately 70 psig (483 kPaG), approximately 80 psig (552 kPaG), approximately 100 p sig (689 kPaG), approximately 150 psig (1,034 kPaG), approximately 200 psi g (1,379 kPaG), approximately 250 psig (1,724 kPaG), or approximately 30 0 psig (2,068 kPaG) or from about atmospheric pressure to about 30 0 psig (2,068 kPaG), approximately 5 psig (34 kPaG) to approximately 250 psig (1,724kPaG), approximately 10psig (69kPaG) to approximately 200psig (1,3 79kPaG), approximately 15psig (103kPaG) to approximately 150psig (1,034k PaG), approximately 20 psig (138 kPaG) ~ approximately 100 psig (689 kPaG), Approximately 25 psig (172 kPaG) to approximately 80 psig (552 kPaG), approximately 30 psi g(207kPaG) ~ approx. 70psig (483kPaG), approx. 35psig (241k PaG) ~ approx. 60 psig (414 kPaG), approx. 40 psig (276 kPaG) ~ approx. 50 psig (345 kPaG), or about 140 kPaG to about 200 kPaG, etc. Maintaining the first reaction operating pressure within any range defined between any two of the aforementioned values. Preferably, the first reaction operating pressure is from about 5 psig (34 kPaG) to about More preferably, the first reaction operating pressure is 200 psig (1,379 kPaG). , approximately 10 psig (69 kPaG) to approximately 150 psig (1,034 kPaG). Most preferably, the first reaction operating pressure is from about 20 psig (138 kPaG) to about 100 psig (689 kPaG).

[0034] In addition to trifluoroacetyl iodide and hydrogen halide, the intermediate product stream contains unreacted The intermediate product stream further comprises trifluoroacetyl halide and hydrogen iodide. It may also contain small amounts of other organic compounds, such as trifluoroiodomethane (CF3I). .

[0035] The composition of organic compounds in the intermediate product stream was determined by gas chromatography (GC) analysis and This can be measured by gas chromatography-mass spectrometry (GC-MS) analysis. The peak areas provided by the GC analysis for each of the compounds are those of the organic compounds. The GC area percentage (GC area%) of all organic compounds in the intermediate product stream was calculated based on the GC area percentage (GC area%) of all organic compounds in the intermediate product stream. The GC area % can be combined to provide a measure of the relative concentration of It can be interpreted as being equivalent to weight percent.

[0036] The concentration of unreacted trifluoroacetyl halide in the intermediate product stream is determined by the G C area %, for example, about 1%, about 3%, about 5%, about 10%, about 15%, about 20%, It may be as low as about 25%, about 30%, about 35%, about 40%, or about 45%, or about 5%. 0%, approximately 55%, approximately 60%, approximately 65%, approximately 70%, approximately 75%, approximately 80%, approximately 85%, or It may be as high as about 90%, or from about 1% to about 90%, from about 5% to about 85%, from about 10% to about 80%, approx. 15% to approx. 75%, approx. 20% to approx. 70%, approx. 25% to approx. 65%, approx. 30% to approx. 60%, approximately 35% to approximately 55%, approximately 40% to approximately 50%, approximately 1% to approximately 3%, approximately 5% to approximately 40% or any range defined between any two of the preceding values, such as about 5% to about 60%. Preferably, the unreacted trifluoroacetyl halide in the intermediate product stream is The concentration of unreacted tocopherols in the intermediate product stream can be from about 1% to about 50%. The concentration of trifluoroacetyl halide can be about 1% to about 40%. The concentration of unreacted trifluoroacetyl halide in the intermediate product stream is about 1% to about 30%. It is possible.

[0037] Trifluoroacetyl halides, trifluoroacetyl iodides and trifluoroiodides The concentrations of organic compounds in the intermediate stream, excluding methane, were calculated as GC area % of all organic compounds. Approximately 15%, approximately 14%, approximately 13%, approximately 12%, approximately 11%, approximately 10%, approximately 9%, approximately 8% , about 7%, about 6%, about 5%, about 4%, about 3%, about 2%, about 1%, about 0.5%, or about 0. Preferably, the concentration of all other organic compounds in the intermediate product stream is less than 1%. More preferably, the concentration of all other organic compounds in the intermediate product stream is less than about 8%. The concentration may be less than about 4%. Most preferably, all other organic compounds in the intermediate product stream The concentration may be less than about 2%.

[0038] The reaction stream may be, for example, at about 25°C, about 30°C, about 40°C, about 50°C, about 60°C, or about 70°C. to a low first reaction temperature of about 80°C, about 90°C, about 100°C, or about 120°C; or Approximately 150°C, approximately 180°C, approximately 200°C, approximately 220°C, approximately 230°C, approximately 250°C, approximately 300 a high first reaction temperature of about 25°C to about 400°C, about 360°C, or about 400°C; °C, about 30°C to about 360°C, about 40°C to about 300°C, about 50°C to about 280°C, about 60°C Approximately 250°C, approximately 70°C to approximately 230°C, approximately 80°C to approximately 220°C, approximately 90°C to approximately 200°C, approximately Any of the above values, such as 100°C to about 180°C or about 110°C to about 150°C It may be heated to a first reaction temperature within any range defined between the two.

[0039] In general, the conversion of trifluoroacetyl halides is dependent on the choice of catalyst, the first reaction temperature, The molar ratio of hydrogen fluoride to trifluoroacetyl halide and the contact time can be controlled. This can be done.

[0040] The reaction can be carried out at a first reaction temperature of about 25°C to about 400°C, but preferably at a first reaction temperature of about 120°C. At lower reaction temperatures, such as the first reaction temperature below, the reaction may occur at low concentrations in the intermediate product stream. It has been found that trifluoroiodomethane can be produced. Trifluoroiodomethane may be the desired end product, but trifluoroacetone may be the It can form an azeotrope with trifluoroacetyl halides such as acetyl chloride. Therefore, the presence of trifluoroiodomethane in the intermediate product stream can adversely affect the overall efficiency of the process. The azeotrope can reduce the amount of trifluoroacetyl chloride to trifluoroiodine. This makes it difficult to separate the methane and can result in a loss of trifluoroiodomethane.

[0041] At a first reaction temperature of about 120° C. or less, trifluoroiodomethane is added to the intermediate product stream. The concentration of tungsten may be less than 0.002% (or about 20 ppm) of total organic compounds. It has been found that the GC area percentage of trifluoroiodide in the intermediate product stream is less than about 0.002%. For example, in the case of methylethane, the reaction stream may be heated to a temperature of about 25°C, about 30°C, about 35°C, about 40°C, about 45°C, or a low first reaction temperature of about 50°C, about 55°C, about 60°C, about 65°C, or about 70°C; or about 75°C, about 80°C, about 85°C, about 90°C, about 95°C, about 100°C, about 105°C , at a high temperature of about 110°C, about 115°C, or about 120°C, or at a temperature of about 25°C to about 120°C , about 30℃ to about 115℃, about 35℃ to about 110℃, about 40℃ to about 105℃, about 45℃ to about 100℃, approx. 50℃~approx. 95℃, approx. 55℃~approx. 90℃, approx. 60℃~approx. 85℃, approx. 65℃~ It is defined as a temperature between any two of the aforementioned values, such as about 80°C or about 70°C to about 75°C. The reaction stream may be heated to a first reaction temperature within any range. Preferably, the reaction stream is heated to a temperature of about 40°C. The reaction stream may be heated to a first reaction temperature of about 70° C. to about 120° C. More preferably, the reaction stream is heated to a first reaction temperature of about 70° C. to about 120° C. The reaction stream may be heated to a first reaction temperature of about 100° C. Most preferably, the reaction stream is heated to a first reaction temperature of about 80° C. to about It may be heated to a first reaction temperature of 100°C.

[0042] When the reaction stream has a reaction temperature of about 120°C or less, the trifluoroacetate in the intermediate product stream is The concentration of cetyl iodide is, for example, about 10%, about 2%, or about 1% by GC area % of all organic compounds. 0%, approx. 30%, approx. 35%, approx. 40%, approx. 45%, approx. 50%, approx. 55%, approx. 60%, approx. 6 It may be as low as 5% or about 70%, or about 75%, about 80%, about 85%, about 90%, It may be as high as about 95%, about 97%, about 98%, or about 99%, or it may be from about 10% to about 9 9%, about 10% to about 99%, about 30% to about 99%, about 35% to about 98%, about 40% to about 9 7%, about 45% to about 95%, about 50% to about 90%, about 55% to about 85%, about 60% to about 8 0%, about 65% to about 75%, about 50% to about 60%, about 90% to about 99%, or about 95% Within any range defined between any two of the preceding values, such as ~approximately 99% Preferably, the concentration of trifluoroacetyl iodide in the intermediate product stream is about 50% More preferably, the trifluoroacetyl iodide in the intermediate product stream is about 99%. The concentration of triflate in the intermediate product stream can be from about 60% to about 99%. The concentration of fluoroacetyl iodide can be from about 70% to about 99%.

[0043] When the reaction stream has a reaction temperature of about 120°C or less, the trifluoroiodide in the intermediate product stream The concentration of methane in the GC area percent of all organic compounds was less than about 0.010%, about 0. Less than 0.005%, Less than about 0.002%, Less than about 0.001%, Less than about 0.0005%, Less than about 0 Less than 0.0002%, or less than about 0.0001%, or any two of the preceding values Preferably, the trifle content in the intermediate product stream is less than any value defined between 0.01 and 0.02. The concentration of oroiodomethane may be less than about 0.002%. The concentration of trifluoroiodomethane in the stream can be less than about 0.001%. Alternatively, the concentration of trifluoroiodomethane in the intermediate product stream is less than about 0.0005%. could be.

[0044] In other words, if the reaction stream has a first reaction temperature of about 120° C. or less, the intermediate product stream The organic compounds in the GC area percentage of all organic compounds are trifluoromethanesulfonic acid (TFA)-containing compounds, which account for approximately 10% to 99% of the total. trifluoroacetyl iodide, about 1% to about 90% unreacted trifluoroacetyl halide, about 0 Less than 0.010% of trifluoroiodomethane, trifluoroacetyl iodide, Less than approximately 15% of organic compounds other than trifluoroacetyl halides and trifluoroiodomethane The organic compounds in the intermediate product stream may be from about 50% to about 99% trifluoromethane. about 1% to about 50% unreacted trifluoroacetyl halide, about Less than 0.002% trifluoroiodomethane and trifluoroacetyl iodide, Less than approximately 8% of organic compounds other than trifluoroacetyl halides and trifluoroiodomethane It is also specified that the organic compounds in the intermediate product stream may be about 60% to Approximately 99% trifluoroacetyl iodide, approximately 1% to approximately 40% unreacted trifluoroacetyl iodide Trifluoromethyl iodide, less than about 0.001% of trifluoroiodomethane, and trifluoromethyl iodide Cetyl iodide, trifluoroacetyl halide, and trifluoroiodomethane It is also specified that the intermediate product stream may contain less than about 4% organic compounds. The product is about 70% to about 99% trifluoroacetyl iodide, about 1% to about 30% unreacted Trifluoroacetyl halides, less than about 0.0005% trifluoroiodomethane, and and trifluoroacetyl iodide, trifluoroacetyl halide, and trifluoro It is also specified that it may contain less than about 2% of organic compounds other than iodomethane.

[0045] In other words, if the reaction stream has a first reaction temperature of about 120° C. or less, the intermediate product stream The organic compounds in the GC area percentage of all organic compounds are trifluoromethanesulfonic acid (TFA)-containing compounds, which account for approximately 10% to 99% of the total. trifluoroacetyl iodide, about 1% to about 90% unreacted trifluoroacetyl halide, about 0 Less than 0.010% of trifluoroiodomethane, trifluoroacetyl iodide, Less than approximately 15% of organic compounds other than trifluoroacetyl halides and trifluoroiodomethane Alternatively, the organic compounds in the intermediate product stream may consist essentially of from about 50% to about 99% organic compounds. % trifluoroacetyl iodide, about 1% to about 50% unreacted trifluoroacetyl halides lide, less than about 0.002% trifluoroiodomethane, and trifluoroacetyl Approximately 8% other than iodide, trifluoroacetyl halide, and trifluoroiodomethane It is also specified that the intermediate product stream may consist essentially of less than 10 ... The compound is about 60% to about 99% trifluoroacetyl iodide, about 1% to about 40% unsaturated fatty acid iodide, and Reaction trifluoroacetyl halide, less than about 0.001% trifluoroiodomethane, and trifluoroacetyl iodide, trifluoroacetyl halide, and trifluoroacetyl It is also provided that the composition may consist essentially of less than about 4% organic compounds other than diiodomethane. In addition, the organic compounds in the intermediate product stream are approximately 70% to approximately 99% trifluoroacetyl iodide. dihydrochloride, about 1% to about 30% unreacted trifluoroacetyl halide, less than about 0.0005% trifluoroiodomethane, as well as trifluoroacetyl iodide, trifluoroacetate Consisting essentially of less than about 2% organic compounds other than methyl halides and trifluoroiodomethane It is also stipulated that it can be.

[0046] In other words, if the reaction stream has a first reaction temperature of about 120° C. or less, the intermediate product stream The organic compounds in the GC area percentage of all organic compounds are trifluoromethanesulfonic acid (TFA)-containing compounds, which account for approximately 10% to 99% of the total. trifluoroacetyl iodide, about 1% to about 90% unreacted trifluoroacetyl halide, about 0 Less than 0.010% of trifluoroiodomethane, trifluoroacetyl iodide, Less than approximately 15% of organic compounds other than trifluoroacetyl halides and trifluoroiodomethane The organic compounds in the intermediate product stream may be from about 50% to about 99% tri- fluoroacetyl iodide, about 1% to about 50% unreacted trifluoroacetyl halide, Less than about 0.002% trifluoroiodomethane and trifluoroacetyl iodide , trifluoroacetyl halide, and trifluoroiodomethane. It is also specified that the organic compounds in the intermediate product stream may be about 60 % to about 99% trifluoroacetyl iodide, about 1% to about 40% unreacted trifluoroacetyl iodide Acetyl halides, less than about 0.001% trifluoroiodomethane, and trifluoro trifluoroacetyl iodide, trifluoroacetyl halide, and trifluoroiodomethane It is also specified that the intermediate product stream may consist of less than about 4% of other organic compounds. The organic compound is about 70% to about 99% trifluoroacetyl iodide, about 1% to about 30% Unreacted trifluoroacetyl halide, less than about 0.0005% trifluoroiodine and trifluoroacetyl iodide, trifluoroacetyl halide, and trifluoroacetyl iodide. It is also specified that the composition may consist of less than about 2% organic compounds other than fluoroiodomethane.

[0047] The intermediate product stream may proceed directly to the first distillation column. Alternatively, the intermediate product stream may proceed to the intermediate distillation column. The intermediate product stream passes through a heat exchanger that cools the intermediate product stream before being fed to the first distillation column. You may do so.

[0048] The first distillation column separates the by-products, reactants, and a portion of the organic compounds into trifluoromethane. and configured to separate the product from acetyl iodide to produce a purified intermediate product stream. The first distillation column separates unreacted hydrogen iodide and returns it to the reactant stream, and It may be configured to separate the reacted trifluoroacetyl halide and return it to the reactant stream. The distillation column in step 1 also extracts hydrogen halide for sale, reuse elsewhere, or disposal. The first distillation column may be configured to separate the halogenated hydrocarbon into a halogenated hydrogen stream. Hydrogen halide column for removing hydrogen and light organics, unreacted trifluoroacetyl before sending them to a recycle column to separate the iodide from unreacted hydrogen iodide. Lightweight column to remove unreacted trifluoroacetyl halide and unreacted hydrogen iodide and a heavy column to purge heavy organics and produce a purified intermediate product stream. The distillation column may comprise a series of distillation columns, such as a

[0049] The concentration of trifluoroacetyl iodide in the purified intermediate product stream was about 98 parts by weight. Preferably, the trifluoromethane content in the purified intermediate product stream is greater than 100 percent by weight. The concentration of acetyl iodide may be greater than about 99% by weight. The concentration of trifluoroacetyl iodide in the product stream may exceed about 99.5% by weight. Most preferably, the concentration of trifluoroacetyl iodide in the purified intermediate product stream is about It can exceed 99.7% by weight.

[0050] The concentrations of some impurities in the purified intermediate product stream are Therefore, the use of trifluoroacetyl halide in the reactant stream may be impaired. If the intermediate product stream contains trifluoroacetyl chloride, the purified intermediate product stream may contain chlorotrifluoroacetyl chloride. Fluoroethane, trifluoroacetyl chloride, iodotrifluoromethane, trifluoro difluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid, and chloroform a total of about 1 ppm (parts per million by weight) to about 2 ppm selected from the group consisting of fluoromethane, chloro ... Preferably, the purified intermediate product stream contains 0,000 ppm (approximately 2% by weight) of the compound. are chlorotrifluoroethane, trifluoroacetyl chloride, iodotrifluoroethane Tannin, trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid and chlorotrifluoromethane, More preferably, the purified intermediate product contains 000 ppm (about 1% by weight) of the compound. The stream is composed of chlorotrifluoroethane, trifluoroacetyl chloride, iodotrifluoroethane, Methane, trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid a total of about 1 ppm to about 5 ppm selected from the group consisting of chlorotrifluoromethane, Most preferably, the purified intermediate product stream contains chloroform. Trifluoroethane, trifluoroacetyl chloride, iodotrifluoromethane, trifluoro fluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid, and chloro trifluoromethane, in a total amount of about 1 ppm to about 3,000 ppm This includes compounds of the formula:

[0051] In other words, the purified intermediate product stream contains at least 98% by weight of trifluoroacetate. Trifluoroacetyl iodide, chlorotrifluoroethane, trifluoroacetyl chloride, iodine Trifluoromethane, trifluoroacetyl fluoride, hexafluoropropanone, trifluoromethane fluoroacetic acid, and chlorotrifluoromethane, The purified product may contain about 20,000 ppm to about 20,000 ppm (about 2% by weight) of the compound. The intermediate product stream is at least 99% by weight of trifluoroacetyl iodide and chlorotrifluoroacetyl iodide. Fluoroethane, trifluoroacetyl chloride, iodotrifluoromethane, trifluoro difluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid, and chloroform fluoromethane, and a total concentration of 1 ppm to 10,000 ppm (1 % by weight of the compound. At least 99.5% by weight of trifluoroacetyl iodide and chlorotrifluoroethanol Trifluoroacetyl chloride, iodotrifluoromethane, trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid, and chlorotrifluoromethyl and a total of 1 ppm to 5,000 ppm of compounds selected from the group consisting of ammonium nitrate, ... It is also specified that the purified intermediate product stream has at least 99.7 wt. Trifluoroacetyl iodide, chlorotrifluoroethane, trifluoroacetyl chlorine chloride, iodotrifluoromethane, trifluoroacetyl fluoride, hexafluoro propanone, trifluoroacetic acid, and chlorotrifluoromethane. It is also stipulated that the composition may contain a total of 1 ppm to 3,000 ppm of compounds.

[0052] In other words, the purified intermediate product stream contains at least 98% by weight of trifluoroacetate. Trifluoroacetyl iodide, chlorotrifluoroethane, trifluoroacetyl chloride, iodine Trifluoromethane, trifluoroacetyl fluoride, hexafluoropropanone, trifluoromethane fluoroacetic acid, and chlorotrifluoromethane, pm to about 20,000 ppm (about 2% by weight) of compounds. the purified intermediate product stream being at least 99% by weight trifluoroacetyl iodide; Chlorotrifluoroethane, trifluoroacetyl chloride, iodotrifluoromethane , trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid, and and chlorotrifluoromethane, and ppm (1% by weight) of the compound. The intermediate product stream is at least 99.5 wt. % trifluoroacetyl iodide and Iodotrifluoroethane, trifluoroacetyl chloride, iodotrifluoromethane, Trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid, and chlorotrifluoromethane, in a total concentration of 1 ppm to 5,000 pp and m. At least 99.7% by weight of trifluoroacetyl iodide and chlorotrifluoro Ethane, trifluoroacetyl chloride, iodotrifluoromethane, trifluoroacetone thyl fluoride, hexafluoropropanone, trifluoroacetic acid, and chlorotrifluoride a total of 1 ppm to 3,000 ppm of compounds selected from the group consisting of fluoromethane, It also provides that the term may essentially be a product of a product.

[0053] In other words, the purified intermediate product stream contains at least 98% by weight of trifluoroacetate. Trifluoroacetyl iodide, chlorotrifluoroethane, trifluoroacetyl chloride, iodine Trifluoromethane, trifluoroacetyl fluoride, hexafluoropropanone, trifluoromethane fluoroacetic acid, and chlorotrifluoromethane, The purified product may consist of about 20,000 ppm to about 20,000 ppm (about 2% by weight) of the compound. The intermediate product stream is at least 99% by weight of trifluoroacetyl iodide and chloroacetyl iodide. Trifluoroethane, trifluoroacetyl chloride, iodotrifluoromethane, trifluoro fluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid, and chloro trifluoromethane, and % by weight of the compound. At least 99.5% by weight of trifluoroacetyl iodide and chlorotrifluoro Ethane, trifluoroacetyl chloride, iodotrifluoromethane, trifluoroacetone thyl fluoride, hexafluoropropanone, trifluoroacetic acid, and chlorotrifluoride a total of 1 ppm to 5,000 ppm of compounds selected from the group consisting of fluoromethane, It is also provided that the purified intermediate product stream may consist of at least 99.7% by weight. % trifluoroacetyl iodide, chlorotrifluoroethane, trifluoroacetone Trifluoromethane, Iodotrifluoromethane, Trifluoroacetyl fluoride, Hexafluoro a compound selected from the group consisting of chloropropanone, trifluoroacetic acid, and chlorotrifluoromethane; It is also specified that the compound may consist of a total of 1 ppm to 3,000 ppm of selected compounds. do.

[0054] The purified intermediate product stream may be stored or converted to trifluoroiodomethane. The purified product containing trifluoroacetyl iodide may be fed to a second reactor for conversion. The intermediate product stream produced may be fed directly to the second reactor. Alternatively, or additionally, The purified intermediate product stream may be subjected to a second reactor prior to the purified intermediate product stream being fed to the second reactor. The purified intermediate product stream may be passed through a preheater where it is heated.

[0055] The trifluoroacetyl iodide in the purified intermediate product stream is reacted in a second reactor. In response, trifluoroiodomethane and the reaction by-product carbon monoxide ( CO. Formula 2: CF3COI→CF3I+CO.

[0056] The second reactor may be made of stainless steel, nickel, and / or nickel alloys (nickel-clad). chromium alloy, nickel-molybdenum alloy, nickel-chromium-molybdenum alloy, or nickel The second reactor may be a heated tube reactor including a tube made of a metal such as a copper-copper alloy. The tubes in the reactor may be heated. The second reactor may be any type of packed bed reactor. good.

[0057] The purified intermediate product stream may be heated to, for example, about 200°C, about 250°C, about 300°C, about 31°C, or 0°C, about 320°C, about 325°C, about 330°C, about 340°C, about 350°C, or about 36 a second reaction temperature as low as 0°C, or at about 370°C, about 380°C, about 390°C, about 400°C, Approximately 425°C, approximately 450°C, approximately 475°C, approximately 500°C, approximately 525°C, approximately 550°C, approximately 575 a high second reaction temperature of about 200°C to about 600°C, or about 25°C to about 600°C; 0℃ to approximately 600℃, approximately 300℃ to approximately 600℃, approximately 320℃ to approximately 450℃, approximately 325℃ to approximately 400℃, approx. 330℃ to approx. 390℃, approx. 340℃ to approx. 380℃, approx. 350℃ to approx. 370℃ or between any two of the aforementioned values, such as about 340°C to about 360°C. Preferably, the second catalyst is heated to a temperature between about 250°C and about 500°C. More preferably, the second catalyst may be heated to a second reaction temperature of about 300°C to about 40°C. The second catalyst may be heated to a second reaction temperature of about 300° C. to about 500° C. Most preferably, the second catalyst is heated to a second reaction temperature of about 300° C. to about 500° C. It may be heated to a second reaction temperature of 350°C.

[0058] The trifluoroacetyl iodide in the purified intermediate product stream is contained in the second reactor. The reaction may occur in the presence of a second catalyst containing a second catalyst such as stainless steel, nickel, or Kel-chromium alloy, nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, aluminum Na, silicon carbide, platinum, palladium, rhenium, activated carbon (Norit-PK35, Cal gon or Shirasagi carbon, or a combination thereof. The catalyst may be in the form of a mesh, pellets, or spheres contained within the second reactor. The two catalysts may have an average diameter ranging from about 1 mm to about 25 mm.

[0059] When the second catalyst comprises platinum, palladium, and / or rhenium, the second catalyst is supported. The second catalyst may be in the form of platinum, palladium, and / or rhenium on a support. The amount of platinum, palladium, and / or rhenium on the support may include alumina or carbon. is expressed as a percentage of the total combined weight of platinum, palladium, and / or rhenium and the support. For example, about 0.01 weight percent (wt%), about 0.1 wt%, about 0.3 wt%, As little as about 0.5 wt%, about 0.7 wt%, about 1 wt%, about 2 wt%, or about 3 wt% or about 4 wt.%, about 5 wt.%, about 6 wt.%, about 8 wt.%, or about 10 wt.% or about 0.01% by weight to about 10% by weight, 0.1% by weight to about 10% by weight, or about 0.5% to about 8% by weight, about 1% to about 6% by weight, about 2% to about 5% by weight, about 3 weights % to about 4% by weight, about 2% to about 3% by weight, or about 0.5% to about 5% by weight, The range may be within any range defined between any two of the aforementioned values. The amount of platinum, palladium, and / or rhenium on the support is about 0.1% by weight to about 1% by weight. More preferably, the amount of platinum, palladium, and / or rhenium on the support is about It may be 0.3% by weight to about 0.7% by weight. Most preferably, platinum, palladium, etc., are present on a support. and / or the amount of rhenium may be about 0.5 wt.%.

[0060] Preferably, the second catalyst comprises activated carbon, about 0.1% to about 1% by weight of platinum on a support; About 0.1 wt. % to about 1 wt. % palladium on the support, about 0.1 wt. % to about 1 wt. % rhenium, or a combination thereof. More preferably, the second catalyst comprises activated carbon. or about 0.3% to about 0.7% by weight of palladium on the support. Most preferably, The second catalyst comprises activated carbon.

[0061] The second catalyst may be, for example, Norit-PK35, Calgon, or Shirasag. The activated carbon may be in the form of activated carbon pellets or spheres. The activated carbon may be, for example, about 500 grams per Square meters (m 2 / g), approx. 800m 2 / g, approx. 850m 2 / g, approx. 900m 2 / g, Approximately 950m 2 / g, or approximately 1,000m 2 / g, or approximately 1,100 m 2 / g, approx. 1,200m 2 / g, approx. 1,300m 2 / g, approx. 1,400m 2 / g, about 1, 600m 2 / g, approx. 1,800m 2 / g, approx. 2,000m 2 / g, or approximately 3,000 m 2 / g, or approximately 500m 2 / g ~ approx. 3,000m 2 / g, approx. 800m 2 / g ~ approx. 2,000m 2 / g, approx. 850m 2 / g ~ approx. 1,800m 2 / g, approx. 900m 2 / g ~ approx. 1,600m 2 / g, approx. 950m 2 / g ~ approx. 1,400m 2 / g, approx. 1,000 m 2 / g ~ approx. 1,200m 2 / g, or approximately 850m 2 / g ~ approx. 1,300m 2 / gna The surface area may be within any range defined between any two of the aforementioned values, such as .

[0062] Activated carbon can be, for example, about 0.2 nanometers (nm), about 0.5 nm, about 1 nm, about 1 Small average pore diameters of about 0.5 nm, about 2 nm, or about 2.5 nm, or about 3 nm, about 5 nm m, a large average pore size of about 10 nm, about 15 nm, about 20 nm, or about 25 nm, or is about 0.2 nm to about 25 nm, about 0.2 nm to about 20 nm, about 1.0 nm to about 15 nm, Approximately 1.5 nm to approximately 10 nm, approximately 2 nm to approximately 5 nm, or approximately 2.5 nm to approximately 3 nm, etc. The porous porous material may have an average pore size within any range defined between any two of the aforementioned values. stomach.

[0063] Alternatively, the second catalyst may be present on the surface of the second reactor itself, which contacts the purified intermediate product stream. The surface may consist of: The catalytic effect may be provided without the need for an additional solid catalyst.

[0064] The purified intermediate product stream may be purified for, for example, about 0.1 seconds, 1 second, about 2 seconds, about 3 seconds, about 5 seconds, For a short contact time of about 8 seconds, about 10 seconds, about 12 seconds, or about 15 seconds, or for a short contact time of about 18 seconds, 2 0 seconds, about 25 seconds, about 30 seconds, about 35 seconds, about 40 seconds, about 50 seconds, about 60 seconds, or about 30 For a long contact time of 0 seconds, or from about 0.1 seconds to about 300 seconds, from about 1 second to about 60 seconds, or from about 3 seconds to about 50 seconds, about 5 seconds to about 40 seconds, about 8 seconds to about 35 seconds, about 10 seconds to about 30 seconds, about 12 seconds to about 25 seconds seconds, about 15 seconds to about 20 seconds, about 20 seconds to about 25 seconds, about 10 seconds to about 40 seconds, or about 10 seconds Any connection within any range defined between any two of the preceding values, such as ~approximately 30 seconds The purified intermediate product stream may be contacted with a second catalyst for a contact time of about The purified cellulose may be contacted with the second catalyst for a contact time of from 1 second to about 60 seconds. The intermediate product stream may be contacted with the second catalyst for a contact time of from about 2 seconds to about 50 seconds. Alternatively, the purified intermediate product stream is contacted with a second catalyst for a contact time of from about 3 seconds to about 30 seconds. Can be touched.

[0065] The reaction may be carried out at, for example, about atmospheric pressure, about 5 psig (34 kPaG), about 10 psig (69 kPaG), approximately 15 psig (103 kPaG), approximately 20 psig (138 kPaG), Approximately 25 psig (172 kPaG), approximately 30 psig (207 kPaG), approximately 35 psi g (241 kPaG), approximately 40 psig (276 kPaG) or approximately 50 psig (3 to a low second reactor operating pressure of about 60 psig (414 kPaG), Approximately 70 psig (483 kPaG), approximately 80 psig (552 kPaG), approximately 100 ps ig (689kPaG), approximately 120psig (827kPaG), approximately 150psig (1 ,034kPaG), approximately 200psig (1,379kPaG), approximately 250psig (1 ,724kPaG), or a high second reaction of about 300 psig (2,068kPaG) Operating pressure: about atmospheric pressure to about 300 psig (2,068 kPaG), about 5 psig (34kPaG) to approximately 300 psig (2,068 kPaG), approximately 5 psig (34kP aG) ~ approx. 250 psig (1,724 kPaG), approx. 10 psig (69 kPaG) Approximately 200 psig (1,379 kPaG), approximately 15 psig (103 kPaG) to approximately 15 0 psig (1,034 kPaG), approximately 20 psig (138 kPaG) to approximately 120 psig ig (827kPaG), approx. 25psig (172kPaG) ~ approx. 100psig (68 9kPaG), approximately 30psig (207kPaG) to approximately 80psig (552kPaG) , about 35 psig (241 kPaG) to about 70 psig (483 kPaG), about 40 ps ig (276kPaG) ~ approx. 70psig (483kPaG), approx. 50psig (345 kPaG) ~ approx. 60 psig (414 kPaG), 50 psig (345 kPaG) ~ approx. 250 psig (1,724 kPaG), approximately 100 psig (689 kPaG) to approximately 20 0 psig (1,379 kPaG), or approximately 150 psig (1,034 kPaG) ~ approximately 200 psig (1,379 kPaG), or between any two of the preceding values. The second reaction operating pressure may be maintained within any range defined above.

[0066] The conversion of trifluoroacetyl iodide was significantly higher than that at atmospheric pressure even in the absence of a second catalyst. It has been found that significant improvements can be achieved by operating at higher pressures than

[0067] The final product stream may proceed directly to a second distillation column. Alternatively, the final product stream may proceed directly to a second distillation column. Passing through a heat exchanger that cools the final product stream before it is fed to the second distillation column You may do so.

[0068] The final product stream is trifluoroiodomethane and carbon monoxide by-product, as shown in Equation 2. and unreacted trifluoroacetyl iodide. The final product stream composition is trifluoroacetyl chloride (CF3COCl), and Residual impurities from purified intermediate product streams, such as trifluoroethane (C2H2ClF3), Pure, as well as trifluoromethane (CHF3), hexafluoroethane (C2F6), Trifluoroacetyl fluoride (CF3COF), hexafluoropropanone (CF3C OCF3), trifluoroacetaldehyde (CF3COH), trifluorochloromethane Fluorocarbon (CF3Cl), pentafluoroiodoethane (C2F5I), difluoroiodomethane (CHF2I), pentafluoropropanone (CF3COCHF2), trifluoroacetic acid Acid anhydride (CF3COOCOCF3), heptafluoroiodopropane (C3F7I), Iodomethane (CH3I), difluorochloroiodomethane (CClF2I), and / or may further contain by-products such as trifluoroacetic acid (CF3COOH).

[0069] The second distillation column removes unreacted trifluoroacetyl iodide and by-products (carbon monoxide). Separation of fluorocarbons (e.g., nitrogen, trifluoromethane, and hexafluoroethane) from the final product stream composition The second distillation column is configured to separate unreacted trifluoroacetyl iodide. and returning it to the purified intermediate product stream. It also separates the carbon monoxide into a carbon monoxide stream for sale, reuse elsewhere, or disposal. The device may be configured to:

[0070] In addition to trifluoroiodomethane, the final product stream composition may contain chlorotrifluoroethane. The third distillate contains ethane and may also contain residual carbon monoxide and hydrogen halides. The distillation column separates a portion of the chlorotrifluoroethane from the trifluoroiodomethane. The third distillation column also separates residual carbon monoxide and hydrogen chloride into a trifle. and separating the fluoroiodomethane from the fluoroisopropyl methyl ether to produce a purified final product composition. The second distillation column and the third distillation column may be , pentafluoroiodoethane, difluoroiodomethane, pentafluoropropanone, Trifluoroacetic anhydride, heptafluoroiodopropane, iodomethane, difluorooctadecane By-products such as iodomethane and / or trifluoroacetic acid, as well as trifluoro Acetyl fluoride, hexafluoropropanone, trifluoroacetaldehyde, and A series of distillation columns configured to additionally remove a portion of the trifluoroacetyl chloride. The purified final product composition may be directed to a storage tank.

[0071] The purified final product composition has a trifluoroiodomethane concentration of greater than 99% by weight. Preferably, the concentration of trifluoroiodomethane in the purified final product composition is The concentration may be greater than 99.5% by weight. More preferably, the concentration of thiamin in the purified final product composition is The concentration of trifluoroiodomethane may be greater than 99.7% by weight. Most preferably, the purified trifluoroiodomethane The concentration of trifluoroiodomethane in the final product composition may exceed 99.9% by weight. do.

[0072] The concentrations of some impurities in the purified final product stream are This can impair the performance of the reactant and its intended purpose as an environmentally safe, non-toxic gas. If the trifluoroacetyl halide in the stream contains trifluoroacetyl chloride, The final product composition contains 1 ppm (parts per million by weight) to 500 ppm of chlorotrifluoride. Oroethane, less than 500 ppm of hexafluoroethane, less than 500 ppm of trifluoroethane Contains less than 100 ppm of methyl methyl ether, less than 100 ppm of carbon monoxide, and less than 1 ppm of hydrogen chloride. The final product stream contained 1 ppm to 250 ppm chlorotrifluoroethane, 250 ppm Hexafluoroethane less than 250 ppm, trifluoromethane less than 50 ppm Preferably, the purified effluent contains less than 0.5 ppm of carbon monoxide and less than 0.5 ppm of hydrogen chloride. The final product stream contains 1 ppm to 100 ppm of chlorotrifluoroethane and less than 10 ppm of Hexafluoroethane, less than 100 ppm trifluoromethane, less than 10 ppm monocarboxylic acids More preferably, the mixture contains less than 0.2 ppm of hydrogen chloride.

[0073] The purified final product composition contains trifluoroacetyl fluoride, hexafluoroacetyl fluoride, Propanone, trifluoroacetaldehyde, and trifluoroacetyl chloride The composition may further contain a compound selected from the group consisting of the following compounds in a total amount of 1 ppm to 500 ppm: The final product composition was trifluoroacetyl fluoride, hexafluoropropane from the group consisting of acetaldehyde, trifluoroacetaldehyde, and trifluoroacetyl chloride It is preferable that the composition further contains selected compounds in a total amount of 1 ppm to 250 ppm. The final product composition prepared contains trifluoroacetyl fluoride, hexafluoropropane, From the group consisting of acetaldehyde, trifluoroacetaldehyde, and trifluoroacetyl chloride It is more preferable that the composition further contains a compound selected from the following in an amount of 1 ppm to 100 ppm in total. stomach.

[0074] In other words, the trifluoroacetyl halide in the reactant stream is converted to trifluoroacetyl chloride. When trifluoride is included, the purified final product composition will be at least 99% by weight of trifluoride. Iodomethane, 1 ppm to 500 ppm of chlorotrifluoroethane, and 500 ppm Less than m of hexafluoroethane, less than 500 ppm of trifluoromethane, and 100 ppm of Less than pm of carbon monoxide, less than 1 ppm of hydrogen chloride, and less than 1 ppm of trifluoroacetyl fluoride , hexafluoropropanone, trifluoroacetaldehyde, and trifluoroacetyl and a total of 1 ppm to 500 ppm of compounds selected from the group consisting of benzophenone-4, benzotriazole ... It is also possible that the purified final product composition contains at least 99.5% by weight of trifluoromethyl ... Iodomethane, 1 ppm to 250 ppm of chlorotrifluoroethane, and 250 ppm Less than m of hexafluoroethane, less than 250 ppm of trifluoromethane, and less than 50 ppm of less than 0.5 ppm of carbon monoxide, less than 0.5 ppm of hydrogen chloride, and less than 0.5 ppm of trifluoroacetylfluoride. hexafluoropropanone, trifluoroacetaldehyde, and trifluoroacetone a total of 1 ppm to 250 ppm of a compound selected from the group consisting of methyl methyl chloride, methyl methyl methacrylate, ... It is also specified that the purified final product composition may contain at least 99.7% of the total amount of cellulose. % by weight of trifluoroiodomethane and 1 ppm to 100 ppm of chlorotrifluoroethane and less than 100 ppm of hexafluoroethane and less than 100 ppm of trifluoroethane. Methane, less than 20 ppm of carbon monoxide, less than 0.2 ppm of hydrogen chloride, and trifluoromethane. Trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetaldehyde, and and trifluoroacetyl chloride, in a total amount of 1 ppm to 100 ppm It is also provided that the purified final product composition may comprise compounds of the formula: At least 99.9% by weight of trifluoroiodomethane and 1 ppm to 100 ppm of chlorine. Trifluoroethane and less than 100 ppm of hexafluoroethane and 100 ppm of Less than 20 ppm trifluoromethane, less than 20 ppm carbon monoxide, and less than 0.2 ppm chloride Hydrogen and trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetyl acetaldehyde, and trifluoroacetyl chloride, It is also specified that the compound may be contained in an amount of 1 ppm to 100 ppm.

[0075] In other words, the trifluoroacetyl halide in the reactant stream is converted to trifluoroacetyl chloride. When trifluoride is included, the purified final product composition will be at least 99% by weight of trifluoride. Iodomethane, 1 ppm to 500 ppm of chlorotrifluoroethane, and 500 ppm Less than m of hexafluoroethane, less than 500 ppm of trifluoromethane, and 100 ppm of Less than pm of carbon monoxide, less than 1 ppm of hydrogen chloride, and less than 1 ppm of trifluoroacetyl fluoride , hexafluoropropanone, trifluoroacetaldehyde, and trifluoroacetyl and the remainder of a compound selected from the group consisting of methyl methyl chloride. The final product composition produced contains at least 99.5% by weight of trifluoroiodomethane. , 1 ppm to 250 ppm of chlorotrifluoroethane and less than 250 ppm of hexafluoropropane Fluoroethane, less than 250 ppm of trifluoromethane, and less than 50 ppm of carbon monoxide and hydrogen chloride less than 0.5 ppm, trifluoroacetyl fluoride, hexafluoroacetyl fluoride, From propanone, trifluoroacetaldehyde, and trifluoroacetyl chloride and the remainder of the compound selected from the group consisting of: The purified final product composition is at least 99.7% by weight trifluoroiodomethane and 1 ppm to 100 ppm of chlorotrifluoroethane and less than 100 ppm of hexafluoroisothiazolinone. Fluoroethane, less than 100 ppm trifluoromethane, and less than 20 ppm monoxide Carbon, less than 0.2 ppm hydrogen chloride, trifluoroacetyl fluoride, hexafluoro from isopropanone, trifluoroacetaldehyde, and trifluoroacetyl chloride and the remainder of the compound selected from the group consisting of: and the purified final product composition is at least 99.9% by weight of trifluoroiodine. chlorotrifluoroethane at 1 ppm to 100 ppm and hexane at less than 100 ppm. trifluoroethane and less than 100 ppm trifluoromethane and less than 100 ppm Carbon dioxide, less than 0.2 ppm of hydrogen chloride, trifluoroacetyl fluoride, hexafluoropropanediol Fluoropropanone, trifluoroacetaldehyde, and trifluoroacetyl chloride and the remainder of a compound selected from the group consisting of:

[0076] In other words, the trifluoroacetyl halide in the reactant stream is converted to trifluoroacetyl chloride. When trifluoride is included, the purified final product composition will be at least 99% by weight of trifluoride. Iodomethane, 1 ppm to 500 ppm of chlorotrifluoroethane, and 500 ppm Less than m of hexafluoroethane, less than 500 ppm of trifluoromethane, and 100 ppm of Less than pm of carbon monoxide, less than 1 ppm of hydrogen chloride, and less than 1 ppm of trifluoroacetyl fluoride , hexafluoropropanone, trifluoroacetaldehyde, and trifluoroacetyl and the remainder of a compound selected from the group consisting of benzoyl chloride and benzoyl chloride. The final product composition is at least 99.5% by weight of trifluoroiodomethane and 1 pp chlorotrifluoroethane at 250 ppm to 250 ppm and hexafluoroethane at less than 250 ppm ethane, less than 250 ppm trifluoromethane, less than 50 ppm carbon monoxide, and 0 Less than 0.5 ppm of hydrogen chloride, trifluoroacetyl fluoride, hexafluoropropane From the group consisting of acetaldehyde, trifluoroacetaldehyde, and trifluoroacetyl chloride and the remainder of the compound selected from the group consisting of: The composition comprises at least 99.7% by weight of trifluoroiodomethane and 1 ppm to 1 00 ppm of chlorotrifluoroethane and less than 100 ppm of hexafluoroethane , less than 100 ppm trifluoromethane, less than 20 ppm carbon monoxide, and 0.2 ppm Less than pm of hydrogen chloride, trifluoroacetyl fluoride, hexafluoropropanone, Selected from the group consisting of trifluoroacetaldehyde and trifluoroacetyl chloride and the remainder of the compound to be purified. The composition contains at least 99.9% by weight of trifluoroiodomethane and 1 ppm to 100 ppm of pm of chlorotrifluoroethane, less than 100 ppm of hexafluoroethane, and 10 Less than 0 ppm of trifluoromethane, less than 100 ppm of carbon monoxide, and 0.2 ppm Less than 100% hydrogen chloride and trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetyl fluoride, fluoroacetaldehyde, and trifluoroacetyl chloride. and the remainder of the compound.

[0077] The purified final product stream of the above two-step gas phase processing process is High purity trifluoroiodomethane can be obtained from high purity trifluoroacetyl iodide. The two-step gas phase process has been found to produce a surprisingly good product. The results are suitable for commercial-scale production of trifluoroiodomethane, providing a high yield.

[0078] Alternatively, or additionally, the reactant stream containing trifluoroacetyl iodide is The resulting mixture may be fed to a second reactor for conversion to trifluoroiodomethane, such as The reactant stream containing trifluoroacetyl iodide may be prepared by a process other than the process described above. It can be generated by

[0079] FIG. 1 shows a vapor phase process 10 for producing trifluoroacetyl iodide. As shown in FIG. 1, the process 10 is a process for the synthesis of hydrogen iodide (HI) 12 and , at least one trifluoroacetyl halide, trifluoroacetyl chloride (C Trifluoroacetyl chloride can be prepared by the processes shown in Figures 1 to 3. Although trifluoroacetyl halide is used to exemplify The methyl halide may alternatively or additionally be trifluoroacetyl bromide or trifluoroacetyl bromide. It is understood that the hydrogen iodide 12 may be trifluoroacetyl fluoride. The flows of fluoroacetyl chloride 14 are combined at mixing valve 16 to form reactant stream 18. The reactant stream 18 can be fed directly to the reactor 20. Alternatively, the reactant stream 18 can be fed directly to the reactor 20. The reactant stream 18 passes through a preheater 22 which heats the reactant stream 18 before it is fed to the reactor 20. That's fine.

[0080] The trifluoroacetyl chloride and hydrogen iodide in reactant stream 18 are introduced into reactor 20. Catalyst 24 is reacted in the presence of the catalyst 24 to produce trifluoroacetyl iodine according to formula 1 above. The catalyst produces a product stream 26 containing fluoride (CFCOI) and hydrogen chloride (HCl) by-product.

[0081] In addition to trifluoroacetyl iodide and hydrogen chloride, product stream 26 contains unreacted trifluoroacetyl iodide. Product stream 26 further contains fluoroacetyl chloride and hydrogen iodide. It may also contain small amounts of other organic compounds, such as tetrachloromethane (CF3I).

[0082] Product stream 26 may proceed directly to distillation column 28. Alternatively, product stream 26 may proceed directly to distillation column 28. As shown in FIG. 1, product stream 26 passes through heat exchanger 30 before being fed to distillation column 28. Heat exchanger 30 may be used to cool product stream 26 before it enters distillation column 28. It is composed of:

[0083] Distillation column 28 separates the by-products, reactants, and a portion of the organic compounds into trifluoromethyl ... and configured to separate the acetyl iodide from the purified product stream 32. As shown in FIG. 1, distillation column 28 separates reactant stream 1 from hydrogen iodide flow 36. 8 to separate unreacted hydrogen iodide and return it to the flow of hydrogen iodide 12. and in trifluoroacetyl chloride flow 34 for use in reactant stream 18 The unreacted trifluoroacetyl chloride was separated, and the trifluoroacetyl chloride 14 was obtained. configured to return to low.

[0084] Distillation column 28 also converts hydrogen chloride into salts for sale, reuse elsewhere, or disposal. The process may be configured to separate trifluoroacetyl iodide into a hydrogen chloride waste stream 38. The purified product stream 32 containing the olefins is directed to a storage tank 40 .

[0085] At the above temperature, hydrogen iodide and trifluoroacetyl chloride are reacted in the presence of catalyst 24. Reacting the iodide with trifluoroacetyl iodide yields a highly selective iodide. It has been found to result in high conversions of hydrogen fluoride and trifluoroacetyl chloride. The gas phase process described above with reference to Equation 1 provides surprisingly good process yields, Suitable for the production of trifluoroacetyl iodide on a commercial scale.

[0086] FIG. 2 shows a two-step gas phase process 110 for producing trifluoroiodomethane. As shown in FIG. 2, process 110 is a process flow diagram of a hydrogen iodide (HI) 112 and at least one trifluoroacetyl chloride (CF3COCl) 114 The flow of hydrogen iodide 112 and the flow of trifluoroacetyl chloride 114 are , are combined at a mixing valve 116 to form a reactant stream 118. The reactant stream 118 is Alternatively, the reactant stream 118 may be fed directly to the reactor 120. The reactant stream 118 may pass through a preheater 122 that heats the reactant stream 118 before it is fed to the reactor 120. .

[0087] The trifluoroacetyl chloride and hydrogen iodide in reactant stream 118 are passed through the first reactor 120 reacts in the presence of a first catalyst 124 contained within the catalyst to produce triflate 126 according to Equation 1 above. Intermediate formation involving oroacetyl iodide (CF3COI) and hydrogen chloride (HCl) by-products Generate logistics 126.

[0088] In addition to trifluoroacetyl iodide and hydrogen chloride, intermediate product stream 126 contains unreacted The intermediate product stream 126 further comprises trifluoroacetyl chloride and hydrogen iodide. It may also contain small amounts of other organic compounds, such as trifluoroiodomethane (CF3I). That's fine.

[0089] The intermediate product stream 126 may proceed directly to the first distillation column 128. Alternatively, the intermediate product stream The intermediate product stream 126 is passed through a first distillation column 128 as shown in FIG. The effluent may pass through a heat exchanger 130 before being fed to the first distillation column. The intermediate product stream 126 is configured to cool before entering the ram 128 .

[0090] The first distillation column 128 distills a portion of the by-products, reactants, and organic compounds into trichloroethylene. to separate the fluoroacetyl iodide to produce a purified intermediate product stream 132. As shown in FIG. 2, the first distillation column 128 may be configured to receive the hydrogen iodide flow 13 In step 4, unreacted hydrogen iodide is separated for use in reactant stream 118 and hydrogen iodide 1 It is configured to return to flow 12.

[0091] The first distillation column 128 divides the trifluoroacetyl chloride flow 136 into Separate unreacted trifluoroacetyl chloride for use in reactant stream 118 and The first distillation column is configured to return the distillate to the flow of fluoroacetyl chloride 114. 128 also converts hydrogen chloride into hydrogen chloride stream 13 for sale, reuse elsewhere, or disposal. It is also configured to separate into 8.

[0092] The purified intermediate product stream 132 is fed directly to a second reactor 140, as shown in FIG. Alternatively, purified intermediate product stream 132 may be fed to purified intermediate product stream 13 The purified intermediate product stream 132 is preheated before being fed to the second reactor 140. It may be passed through a heater (not shown).

[0093] The trifluoroacetyl iodide in the purified intermediate product stream 132 is passed through a second reactor 140 in the presence of a second catalyst 142 to produce triflate according to Equation 2 above. producing a product stream 144 containing iodomethane and the reaction by-product carbon monoxide (CO). do.

[0094] Product stream 144 may proceed directly to second distillation column 146, as shown in FIG. Alternatively, product stream 144 may be further treated by distillation before product stream 144 is fed to second distillation column 146. The effluent may pass through a heat exchanger (not shown) which then passes into the second distillation column 146. The cooling system is configured to cool the product stream 144 before

[0095] In addition to trifluoroiodomethane and carbon monoxide, product stream 144 contains unreacted trifluoroisopropyl ether. Fluoroacetyl iodide, trifluoromethane (CHF3), and hexafluoroethane (C2F6), and other by-products such as chlorotrifluoroethane (C2H2ClF3) The second distillation column 146 is a distillation column for separating unreacted trifluoroacetyl iodide and by-products. trifluoromethane and hexafluoroethane) a purified product stream 14 containing trifluoroiodomethane separated from iodomethane; 2, the second distillation column 146 is configured to produce 8. In the reaction trifluoroacetyl iodide flow 150, unreacted trifluoroacetyl The iodide may be separated and returned to the purified intermediate product stream 132. The distillation column 146 also extracts carbon monoxide for sale, reuse elsewhere, or disposal. The carbon monoxide stream 152 may be configured to separate the carbon monoxide from the gas.

[0096] As shown in FIG. 2, the purified product stream 148 containing trifluoroiodomethane is The trifluoroiodine is then directed to a third distillation column 154 for further purification. In addition to chlorotrifluoroethane, the purified product stream 148 contains chlorotrifluoroethane and It may also contain residual carbon monoxide and hydrogen chloride. Trifluoroiodomethane is obtained by separating chlorotrifluoroethane from iodomethane. 2. As shown in FIG. The third distillation column 154 then distills the chloroformate for sale, reuse elsewhere, or disposal. The system may be configured to separate trifluoroethane into chlorotrifluoroethane stream 158. The third distillation column 154 also extracts carbon monoxide and hydrogen chloride into waste stream 16 for disposal. 0. The purified final product containing trifluoroiodomethane may be separated into The product stream 156 may be directed to a storage tank 162 .

[0097] FIG. 3 shows the reaction for producing trifluoroiodomethane from trifluoroacetyl iodide. 2 is a process flow diagram showing a process 210 for the production of purified intermediates. 2, except that product stream 132 is replaced by reactant stream 232. The reactant stream 232 may be the same as the second step of the two-step process described above. Trifluoroacetyl iodide includes the trifluoroacetyl iodide described herein. The reactant stream 232 may be produced by a process other than the process described herein. It may further include trifluoroacetyl iodide produced by the process.

[0098] Although the present invention has been described with respect to exemplary designs, the present invention is not limited to the spirit and scope of this disclosure. Furthermore, this application is not intended to be a substitute for the disclosure of the present invention. It is intended to cover such departures from the present disclosure as come within known or customary practice in the art. It has been done.

[0099] As used herein, "any range defined between any two of the preceding values" means any range defined between any two of the preceding values. The phrase "within a range" means that the values ​​are in a lower part of the list or in a higher part of the list. Any range, whether or not there is one, may be any two of the values ​​listed before such a clause. For example, a pair of values ​​may be selected from two lower values, two higher values, It may be selected from a high value, or a lower and a higher value. [Example]

[0100] Example 1: Preparation of trifluoroacetyl iodide according to formula 1 at higher reaction temperatures Construction In this example, as described above, hydrogen iodide and thiazolinone are reacted according to Equation 1 at higher temperatures. The preparation of trifluoroacetyl iodide from trifluoroacetyl chloride is demonstrated. In a series of 23 experiments, equimolar amounts of trifluoroacetyl chloride and anhydrous iodide were The mixture was passed through a preheater and heated to a temperature of approximately 100° C. The heated reaction mixture was placed in a 3 / 8 inch diameter tube. (9.5 mm) and a 6-inch (152 mm) long stainless steel tube. Depending on the experiment, the temperature was heated to a range of 200 °C to 350 °C and filled with nitrogen at least twice before each experiment. The tube was purged for 1 hour to drive off the moisture. In 21 experiments, the tube was In the remaining two experiments, the tube contained no catalyst. The temperature was varied from 10 seconds to 30 seconds. All exit vapors from each experiment were analyzed by GC and GC-MS. The results are shown in Tables 1, 2, and 3.

[0101] Table 1 shows the reaction conditions (temperature, contact time, etc.) used for each of the 23 experiments. Table 2 lists the main organic compounds of interest corresponding to each of the 23 experiments. Table 3 lists the GC area % of the products corresponding to each of the 23 experiments. and trifluoroiodomethane, trifluoroacetyl iodide, and trifluoroiodide The selectivity percentages for the combination of methyl iodide and trifluoroacetyl iodide are listed in the table. Percent conversion and selectivity are based on GC area % data.

[0102] As shown in Tables 1, 2, and 3, the process described above with reference to Equation 1 yields a conversion percentage of The yield of trifluoroacetyl iodide is over 90% and the selectivity is over 99%. Therefore, Tables 1, 2, and 3 show a surprisingly good result. A process according to the present disclosure for the production of trifluoroacetyl iodide is demonstrated. [Table 1] [Table 2] [Table 3] Example 2: Preparation of trifluoroacetyl iodide according to formula 1 at higher reaction temperatures Construction

[0103] In this example, hydrogen iodide and HCl were prepared according to Equation 1 at higher reaction temperatures, as described above. Demonstrate the preparation of trifluoroacetyl iodide from trifluoroacetyl chloride Trifluoroacetyl chloride at a flow rate of 8.34 g / hour and iodine at a flow rate of 14.08 g / hour Hydrogen chloride was poured into a 3 / 8 inch (9.5 mm) diameter and 6 inch (152 mm) long stainless steel tube. The tube was heated to a temperature of approximately 300°C and filled with nitrogen for at least 1 minute before the experiment. The tube was purged with Pro-Pak (registered trademark) for a contact time of approximately 10 seconds. The catalyst contained a stainless steel catalyst. The process was run continuously for 6.25 hours. The reactor output was set to two dry ice traps, one at about 0℃ to -5℃ and the other at about - Harvested at 78°C.

[0104] A total of 99.8 g of material was recovered, and a portion was analyzed by GC and GC-MS. The compound is a 60% mixture of trifluoroacetyl iodide and trifluoroacetyl chloride. It was found to contain a mixture of trifluoroacetyl iodide in a ratio of 1:40. ranged from 88% to 97% based on GC area %. Example 3: Preparation of trifluoroacetyl iodide according to formula 1 at higher reaction temperatures Construction

[0105] In this example, hydrogen iodide and HCl were prepared according to Equation 1 at higher reaction temperatures, as described above. Demonstrate the preparation of trifluoroacetyl iodide from trifluoroacetyl chloride Trifluoroacetyl chloride at a flow rate of 5.75 g / h and iodide at a flow rate of 13.9 g / h Hydrogen was poured into a 1 / 2 inch (12.7 mm) diameter and 6 inch (152 mm) long stainless steel tube. The tube was heated to a temperature of approximately 250°C and filled with nitrogen for at least 1 minute before the experiment. The tube was purged for 1 hour to drive off moisture. The tube was then heated to 0.5°C on an alumina support for a contact time of approximately 15 seconds. The catalyst contained 5% palladium (3.2 mm pellets). The reactor was run for 5 hours. The reactor output was placed in two dry ice traps, one of which was at about 0°C to - One was collected at 5°C and the other at approximately -78°C.

[0106] A total of 89 g of material was recovered, and a portion was analyzed by GC-MS. A mixture of trifluoroacetyl iodide and trifluoroacetyl chloride in a 70:30 ratio It was found that the compound contained trifluoroacetate to trifluoroiodomethane. The selectivity for methyl iodide ranged from 92% to 98% based on GC area %. The example was repeated with a silicon carbide catalyst (3 mm pellets) with similar results. Example 4: Preparation of trifluoroacetyl iodide according to formula 1 at lower reaction temperatures Construction

[0107] In this example, as described above, hydrogen iodide and thiazolinone are reacted according to Equation 1 at lower temperatures. The production of trifluoroacetyl iodide from trifluoroacetyl chloride is demonstrated. A certain molar ratio of trifluoroacetyl chloride and anhydrous hydrogen iodide was added to a 3 / 4 inch diameter tube. The reactor was passed through a metal tube (19.05 mm). The pressure transducer and control valve at the reactor outlet were The pressure was controlled using a pressure regulator. The tube was heated to temperatures ranging from 40°C to 210°C depending on the experiment. In 26 of the 28 experiments, the tube contained one of several catalysts. In the remaining two experiments, the tube contained no catalyst. Contact times ranged from 6.1 seconds to 7 seconds. The reactor effluent for each experiment was passed through a heat-traced line. Prevent condensation of trifluoroacetyl iodide and direct it to the dry ice trap to remove the crude product. The non-condensable vapors escaping from the dry ice trap were collected in a water scrubber and a caustic separator. The reactor effluent was sampled for GC and GC-MS analysis. Based on the combined feed of trifluoroacetyl chloride and hydrogen iodide The contact time in the reactor for each experiment was calculated. Run times ranged from 8 to 49 hours. At the end of the reaction run time for each experiment, the system was stopped and all vessels were weighed. The crude product collected in the dry ice trap was also weighted for balancing purposes. Samples were taken and analyzed for GC and GC-MS analysis, and the results are shown in Tables 4 and 5.

[0108] Table 4 shows the reaction conditions (temperature, molar ratios, and contact angle) used for each of the 28 experiments. Table 5 lists the experimental conditions (contact time, reactor type, pressure, and catalyst) for each of the 28 runs. The corresponding GC area percentages of the main organic compounds of interest, as well as the area percentages of trifluoroacetyl chloride The percent conversion and selectivity to trifluoroacetyl iodide are listed. The percent selectivity and selectivity are based on GC area % data.

[0109] As shown in Tables 4 and 5, the reaction temperature is about 120° C. or less. The process described is designed to reduce the concentration of trifluoroiodomethane to 0.002% (or less) of total organic compounds. is less than about 20 ppm), and the conversion percentage is greater than 80% (with catalyst and trifluoro The ratio of acetyl chloride to hydrogen is approximately 1), and the selectivity for trifluoroacetyl iodide is It is possible to produce trifluoroacetyl iodide with a purity of 99 mol% or more. Thus, Tables 4 and 5 show that trifluoroacetyl iodide gives surprisingly good results. 1 demonstrates a process according to the present disclosure for the production of [Table 4] [Table 5] Example 5: Preparation of trifluoroacetyl iodide according to formula 1 at lower reaction temperatures Evaluation of SiC catalyst life in a structure

[0110] In this example, the lifetime of a silicon carbide catalyst (SiC1-E3-M) was measured at 90°C. Trifluoroacetyl iodide from hydrogen iodide and trifluoroacetyl chloride according to Equation 1 In this example, 20 mL of silicon carbide catalyst was placed in a 3 / 4 in diameter tube. The pressure change at the reactor outlet was measured. The pressure was controlled at 20 psig (138 kPaG) using a diverter and control valve. The system was then stopped, the mass balance was checked, and the crude product was collected for analysis. was repeated for a series of five runs over a total run time of over 455 hours. Shown in Table 6.

[0111] Table 6 shows the reaction conditions (molar ratio, contact time, flow rate) for each of the five consecutive runs. Table 6 also lists the time (time, and cumulative distribution time) for each of the five consecutive runs. The conversion percentage of trifluoroacetyl chloride and trifluoroacetyl iodide The selectivity and GC area % of trifluoroiodomethane are also listed. Percent activity is based on GC area % data.

[0112] The process described above with reference to Equation 1, operating at a reaction temperature of 90° C., as shown in Table 6. trifluoroacetyl iodine without detectable formation of trifluoroiodomethane. During operation for over 455 hours, the deactivation of the silicon carbide catalyst was Not observed. [Table 6] Example 6: Preparation of trifluoroacetyl iodide according to formula 1 at lower reaction temperatures Evaluation of activated carbon catalyst life in a manufacturing process

[0113] In this example, the life of an activated carbon catalyst (Norit ROX0.8) was measured at 90°C. Trifluoroacetyl chloride from hydrogen iodide and trifluoroacetyl chloride according to scheme 1 In this example, 20 mL of activated carbon catalyst was placed in a 3 / 4 inch diameter container. The reactor was loaded into a 19.05 mm Inconel 600 tube. The pressure was controlled using a pressure regulator and control valve. Periodically, the system was shut down and a mass balance The crude product was collected for analysis, and this was followed by a total run time of over 2,000 hours. The results are shown in Table 7.

[0114] Table 7 shows the reaction conditions (pressure, molar ratio, contact time) for each of the 29 consecutive runs. Table 7 also lists the results of 29 consecutive runs (interval, flow time, and cumulative flow time). The percentage of trifluoroacetyl chloride conversion and trifluoroacetyl iodide conversion were The selectivity for the dihydrogenated iodide and the GC area % of trifluoroiodomethane are also listed. The yield and selectivity percentages are based on GC area % data.

[0115] The process described above with reference to Equation 1, operating at a reaction temperature of 90° C., as shown in Table 7. trifluoroacetyl iodine without detectable formation of trifluoroiodomethane. During over 2,051 hours of operation, the deactivation of the activated carbon catalyst was Not observed. [Table 7] Example 7: Isolation of trifluoroacetyl iodide

[0116] This example describes the isolation of trifluoroacetyl iodide. Trifluoroacetyl iodide, about 10% by weight of trifluoroacetyl chloride, about 5 times A mixture containing about 5% by weight of hydrogen iodide and about 5% by weight of hydrogen chloride is charged to the distillation column. The distillation column is equipped with a 10 gallon reboiler, a Cannon Instrument ent Company (State College, PA) 2-inch inner diameter 10 ft. Pro-Pak® column and approximately 30 theoretical plates. The distillation column can be equipped with temperature, absolute pressure, and differential pressure transmitters. The distillation can be performed in about 3 minutes. The column can be operated at a pressure of 0.00 kPaG and a temperature of about 55°C, and hydrogen chloride is released from the top of the column. and product is removed from the bottom of the column. Example 8: Trifluoroacetyl iodide synthesis according to formula 2 with activated carbon catalyst at atmospheric pressure Production of trifluoroiodomethane from iodine

[0117] In this example, trifluoroacetyl iodide according to Equation 2 above at atmospheric pressure was used. This paper demonstrates the production of trifluoroiodomethane from 55 GC area % trifluoroacetyl A mixture of iodide and 45 GC area % trifluoroacetyl chloride was passed through a preheater. The heated reaction mixture was placed in a 3 / 8 inch (9.5 mm) diameter, The tube was heated to approximately 350°C. The tube was heated and purged with nitrogen for at least 1 hour before the experiment to drive off any moisture. The catalyst was Norit-PK35 activated carbon with a contact time of 0 to 15 seconds. was collected in a sample bag for GC analysis and GC-MS analysis.

[0118] Nearly complete conversion of trifluoroacetyl iodide to trifluoroiodomethane was observed. The ratio of trifluoroiodomethane to unreacted trifluoroacetyl iodide was Based on GC area % measurements, less than 0.5% unreacted trifluoroacetyl iodide The ratio was 54:0.22. Example 9: Trifluoroacetyl iodide synthesis according to Equation 2 without catalyst at above atmospheric pressure Preparation of trifluoroiodomethane from

[0119] In this example, the reaction is carried out according to Equation 2 above at pressures above atmospheric pressure without a separate catalyst. This paper demonstrates the production of trifluoroiodomethane from trifluoroacetyl iodide. A feed stream of trifluoroacetyl iodide having at least 99.22 GC area percent was passed through a heated tube. The heating tube was a 0.5 inch (12.7 mm) diameter tube with a 120 mm long heating zone. The tube was made of commercially available pure (>99%) nickel. The flow rate was controlled with a contact time of approximately 10 seconds. The tube contained no catalyst. The feed had a contact time of approximately 10 seconds. The pressure was controlled using a pressure transducer and a control valve at the reactor outlet. The reactor output was measured by GC. The samples were collected in sample bags for analysis and GC-MS analysis. The results are shown in Table 8.

[0120] Table 8 lists the reaction conditions (temperature, pressure) for each of the 20 experiments. 8 also shows the percent conversion of trifluoroacetyl iodide for each of the 20 experiments. The percent conversion and selectivity for trifluoroiodomethane are also listed. are based on GC area % data. Table 8 also shows the results for some of the 28 experiments. The corresponding GC area % of the major organic compounds of interest is also listed.

[0121] Considering the results of Experiments 1 to 10 shown in Table 8, it is clear that operating at higher reaction pressures The process described above with reference to Equation 2 provides high conversion of trifluoroacetyl iodide. , with high selectivity for the formation of trifluoroiodomethane. Iodomethane can be produced. This effect is provided by the nickel reactor itself. This was observed without the use of a catalyst, excluding any catalytic effect that may be present. This may result in improved results at lower reaction temperatures, but the catalyst may need to be regenerated or replaced. Not having to do this can provide for a more efficient process overall.

[0122] Considering the results of experiments 11 to 20 shown in Table 8, the improved results are comparable to those without a catalyst. This has been shown to be particularly pronounced at higher pressures combined with higher temperatures. The operating pressure was 200 psig (experiment 16-20) compared to atmospheric pressure operation. Improved results have been shown at temperatures above 300°C in experiments 11-15). [Table 8] Example 10: Separation of trifluoroiodomethane

[0123] This example describes the separation of trifluoroiodomethane. fluoroiodomethane, about 10% by weight trifluoroacetyl iodide, and about 5% by weight The distillation column can be charged with a mixture containing about 10 gallon reboiler at 25°C, Cannon Instrument Com 10-foot, 2-inch inner diameter pipe manufactured by PG Company (State College, PA) The distillation column may comprise an o-Pak column and about 30 theoretical plates. The distillation can be carried out at a pressure of approximately 275 kPaG. The condenser was run at a temperature of about -13°C to recover trifluoroiodomethane. It is possible. Aspects

[0124] Aspect 1 is a vapor phase process for producing trifluoroiodomethane, The process involves the use of hydrogen iodide, trifluoroacetyl chloride, trifluoroacetyl fluoride, and trifluoroacetyl bromide, trifluoroacetyl bromide, and combinations thereof. and at least one trifluoroacetyl halide comprising: reacting the reactant stream in the presence of a first catalyst at a first reaction temperature of from about 25°C to about 400°C generating an intermediate product stream comprising trifluoroacetyl iodide; and reacting in the presence of a second catalyst at a second reaction temperature of about 200°C to about 600°C to produce triflate and producing a final product stream comprising oroiodomethane.

[0125] In the second aspect, in the step of reacting the reactant stream, the first reaction temperature is about 40° C. to about 12° C. 0° C.

[0126] In a third aspect, in the step of reacting the reactant stream, the first reaction temperature is about 70° C. to about 10° C. 0° C.

[0127] In a fourth aspect, in the step of reacting the reactant stream, the first reaction temperature is about 80° C. to about 10° C. 0° C.

[0128] Embodiment 5 provides a process wherein the reactant stream comprises less than about 500 ppm by weight of oxygen. The process is according to any one of aspects 1 to 4.

[0129] Embodiment 6 provides a process wherein the reactant stream comprises less than about 100 ppm by weight of oxygen. The process is according to any one of aspects 1 to 4.

[0130] Embodiment 7 provides a process, wherein the reactant stream comprises less than about 10 ppm by weight of oxygen. The process according to any one of aspects 1 to 4.

[0131] Embodiment 8 provides a process in which the reactant stream comprises less than about 1 ppm by weight of oxygen. The process is described in any one of methods 1 to 4.

[0132] A 9th aspect of the present invention relates to a process for preparing a hydrogen iodide solution, the process comprising the steps of: providing a hydrogen iodide solution containing less than about 500 ppm by weight of water; The process is according to any one of aspects 1 to 8.

[0133] Embodiment 10 is directed to a method for preparing a hydrogen iodide solution, the method comprising the steps of: providing a hydrogen iodide solution containing less than about 100 ppm by weight of water; The process according to any one of aspects 1 to 8 includes:

[0134] Embodiment 11 is directed to a method for preparing a hydrogen iodide solution, the method comprising the steps of: providing a hydrogen iodide solution containing less than about 10 ppm by weight of water; The process is according to any one of aspects 1 to 8.

[0135] Embodiment 12 is directed to a method for preparing a hydrogen iodide solution, the method comprising the steps of: providing a solution containing hydrogen iodide; and determining whether the hydrogen iodide contains less than about 1 ppm by weight of water. The process according to any one of the first to eighth aspects.

[0136] Aspect 13 is a method for preparing a fluororesin comprising the steps of: reacting hydrogen iodide with a trifluoroacetyl halide; is from about 0.1:1 to about 10:1 is.

[0137] A fourteenth aspect of the present invention relates to a method for preparing a fluororesin comprising the steps of: 13. The process according to any one of aspects 1 to 12, wherein the molar ratio of It is.

[0138] Embodiment 15 is directed to a method for preparing a fluororesin comprising the steps of: reacting hydrogen iodide with a trifluoroacetyl halide; 13. The process according to any one of aspects 1 to 12, wherein the molar ratio of It is.

[0139] Aspect 16 is a method for preparing a fluororesin comprising the steps of: reacting hydrogen iodide with a trifluoroacetyl halide; 13. The process according to any one of aspects 1 to 12, wherein the molar ratio of It is.

[0140] Aspect 17 is directed to a method for reacting a reactant stream, the method comprising the steps of: Bon, stainless steel, nickel, nickel-chromium alloy, nickel-chromium-molybdenum Alloys, nickel-copper alloys, copper, alumina, platinum, palladium, metal carbides, non-metal carbides or a combination thereof.

[0141] Embodiment 18 is directed to a method for preparing a catalyst, wherein the first catalyst is selected from the group consisting of activated carbon, mesocarbon, stainless steel, platinum on a support, Any of embodiments 1-16, including palladium on a support, silicon carbide, or a combination thereof. The process described in any one of the above is

[0142] Aspect 19 is a method for preparing a catalyst comprising the steps of: a) preparing a catalyst having a first catalyst; b) preparing a catalyst having a second catalyst; c) preparing a catalyst having a second catalyst; d) preparing a catalyst having a second catalyst; e) preparing a catalyst having a second catalyst; f ... 17. The process according to any one of aspects 1 to 16, comprising:

[0143] Example 20 is any of Examples 1-16, wherein the first catalyst comprises activated carbon or silicon carbide. The process is described in

[0144] In a twenty-first aspect, in the step of reacting the reactant flow, the reactant flow is reacted for about 0.1 seconds to about 30 seconds. 21. The process of any one of aspects 1 to 20, wherein the first catalyst may be contacted with the first catalyst for a contact time of 0 seconds. It is.

[0145] In the embodiment 22, in the step of reacting the reactant flow, the reactant flow is reacted for about 5 seconds to about 60 seconds. 21. The process of any one of aspects 1 to 20, wherein the first catalyst may be contacted with the first catalyst for a contact time. do.

[0146] In the embodiment 23, in the step of reacting the reactant flow, the reactant flow is reacted for about 10 seconds to about 40 seconds. 21. The process of any one of aspects 1 to 20, wherein the first catalyst may be contacted with the first catalyst for a contact time of be.

[0147] In a twenty-fourth embodiment, in the step of reacting the reactant flow, the reactant flow is reacted for about 15 seconds to about 35 seconds. 21. The process of any one of aspects 1 to 20, wherein the first catalyst may be contacted with the first catalyst for a contact time of be.

[0148] In a twenty-fifth aspect, in the reacting step, the reactant stream is heated to a pressure of from about atmospheric pressure to about 300 psig ( 25. The process of any one of aspects 1 to 24, wherein the pressure is at a pressure of 2,068 kPaG.

[0149] Embodiment 26 relates to a method for reacting a reactant stream at a pressure of about 5 psig (34 kPaG). 25. The method of any one of claims 1 to 24, wherein the pressure is about 200 psig (1,379 kPaG). This is the process described above.

[0150] Embodiment 27 relates to a method for reacting a reactant stream at a pressure of about 10 psig (69 kPaG 25. Any of embodiments 1 to 24, wherein the pressure is between about 150 psig (1,034 kPaG) and about 150 psig (1,034 kPaG). The process described is as follows:

[0151] Embodiment 28 relates to a method for reacting a reactant stream at a pressure of about 20 psig (138 kPa). 25. The method of any one of embodiments 1 to 24, wherein the pressure is between about 100 psig (689 kPaG) and about 100 psig (689 kPaG). This is the process described above.

[0152] Aspect 29 relates to a process for producing a cyclohexane- ... 29. The process of any one of aspects 1 to 28, wherein the temperature is from about 100°C to about 500°C.

[0153] Embodiment 30 further comprises reacting the intermediate product stream, wherein the second reaction temperature is about 300° C. 29. The process of any one of aspects 1 to 28, wherein the temperature is from about 100°C to about 400°C.

[0154] Aspect 31 is directed to a method for producing a cyclohexane- ... 29. The process of any one of aspects 1 to 28, wherein the heating temperature is from about 300°C to about 350°C.

[0155] Aspect 32 further relates to a method for reacting an intermediate product stream, the method comprising: reacting the intermediate product stream for about 0.1 seconds; 32. The method of any one of embodiments 1 to 31, wherein the second catalyst is contacted for a contact time of about 300 seconds. This is the process.

[0156] In a third aspect, in the step of reacting the intermediate product stream, the intermediate product stream is reacted for about 1 second to about 32. The process of any one of aspects 1 to 31, which may be contacted with a second catalyst for a contact time of 60 seconds. It's Seth.

[0157] In a thirty-fourth embodiment, in the step of reacting the intermediate product stream, the intermediate product stream is reacted for about 2 seconds to about 32. The process of any one of embodiments 1 to 31, which may be contacted with a second catalyst for a contact time of 50 seconds. It's Seth.

[0158] In a third aspect, in the step of reacting the intermediate product, the intermediate product flow is 32. The process of any one of embodiments 1 to 31, wherein the first catalyst is contacted with the second catalyst for a contact time of 0 seconds. It is.

[0159] Embodiment 36 describes a method for reacting an intermediate product stream, the method comprising: , nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy, nickel-copper Alloys, copper, alumina, silicon carbide, platinum, palladium, rhenium, activated carbon, mesocarbon or a combination thereof.

[0160] Aspect 37 is directed to a method for reacting an intermediate product stream, the method comprising the step of: about 0.1 wt % to about 1 wt % platinum on the support, and about 0.1 wt % to about 1 wt % palladium on the support. rhenium, about 0.1 wt. % to about 1 wt. % rhenium on a support, or a combination thereof. The process according to any one of embodiments 1 to 35.

[0161] Aspect 38 relates to a process for reacting an intermediate product stream, wherein the second catalyst is activated carbon, or Any of embodiments 1-35, comprising about 0.3% to about 0.7% by weight palladium on the support. The process is described in

[0162] Aspect 39 is directed to a process comprising reacting the intermediate product stream, wherein the second catalyst comprises activated carbon. The process according to any one of embodiments 1 to 35.

[0163] Embodiment 40 relates to a method for producing a catalyst comprising the steps of: reacting an intermediate product stream; 36. The process of any one of embodiments 1 to 35, wherein the reactor surface contacts the

[0164] Embodiment 41 is directed to a method for preparing a refrigerant containing an intermediate product stream, the method comprising: reacting the intermediate product stream at a pressure of from about 5 psig (34 kPaG) to about 41. The method of any one of embodiments 1 to 40, wherein the pressure is 300 psig (2,068 kPaG). It's a process.

[0165] Embodiment 42 is a vapor phase process for producing trifluoroiodomethane, The process involves the reaction of hydrogen iodide with trifluoroacetyl chloride and trifluoroacetyl fluoride. fluoride, trifluoroacetyl bromide, and combinations thereof. and at least one trifluoroacetyl halide, and subjecting the reactant stream to a first reaction at a first reaction temperature of about 25°C to about 400°C in the presence of a first catalyst. Pressure from atmospheric pressure to approximately 300 psig (2,068 kPaG), for approximately 0.1 seconds to approximately 300 seconds reacting for a contact time of 1 to produce an intermediate product stream containing trifluoroacetyl iodide. and subjecting the intermediate product stream to a second reaction at a temperature of about 200°C to about 600°C in the presence of a second catalyst. reacting at the reaction temperature for a second contact time of about 0.1 seconds to about 300 seconds to form a trifluoromethyl group; and producing a final product stream comprising iodomethane, wherein the hydrogen iodide and trifluoromethane are reacted with each other to form a final product stream comprising iodomethane. The molar ratio of the first catalyst to the acetyl halide is about 0.1:1 to about 10:1, and the second catalyst is activated carbon. , mesocarbon, stainless steel, nickel, nickel-chromium alloy, nickel-chromium- Molybdenum alloy, nickel-copper alloy, copper, alumina, platinum, palladium, metal carbide, non a metal carbide, or a combination thereof, and the second catalyst comprises stainless steel, nickel, Nickel-chromium alloy, nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, aluminum Lumina, silicon carbide, platinum, palladium, rhenium, activated carbon, mesocarbon, or any of these Includes a combination of:

[0166] Embodiment 43 is a vapor phase process for producing trifluoroiodomethane, The process involves the reaction of hydrogen iodide with trifluoroacetyl chloride and trifluoroacetyl fluoride. fluoride, trifluoroacetyl bromide, and combinations thereof. and at least one trifluoroacetyl halide, and reacting the reactant stream in the presence of a first catalyst at a first reaction temperature of about 40°C to about 120°C for about 5 minutes. psig (34kPaG) to approximately 200psig (1,379kPaG) for approximately 5 seconds reacting for a first contact time of about 60 seconds to form a medium containing trifluoroacetyl iodide; generating an intermediate product stream; and heating the intermediate product stream in the presence of a second catalyst at about 250°C to about 5 and reacting at a second reaction temperature of about 100° C. for a second contact time of about 1 second to about 60 seconds. and producing a final product stream comprising fluoroiodomethane, The molar ratio of the first catalyst to the fluoroacetyl halide is about 0.5:1 to about 2:1, and the second catalyst is Activated carbon, mesocarbon, stainless steel, platinum on a support, palladium on a support, silicon carbide or a combination thereof, wherein the second catalyst comprises activated carbon, about 0.1 wt. % to about 10 wt. % on a support. 1% by weight platinum, about 0.1% to about 1% by weight palladium on a support, about 0.1% to about 1% by weight palladium on a support % to about 1% by weight of rhenium, or a combination thereof.

[0167] Embodiment 44 is a vapor phase process for producing trifluoroiodomethane, The process involves the reaction of hydrogen iodide with trifluoroacetyl chloride and trifluoroacetyl fluoride. fluoride, trifluoroacetyl bromide, and combinations thereof. and at least one trifluoroacetyl halide, and subjecting the reactant stream to a first reaction at a first reaction temperature of about 70°C to about 100°C in the presence of a first catalyst. At a pressure of 0 psig (69 kPaG) to approximately 150 psig (1,034 kPaG), reacting for a first contact time of from about 0 seconds to about 40 seconds to produce a mixture containing trifluoroacetyl iodide; and heating the intermediate product stream in the presence of a second catalyst at about 300°C to reacting at a second reaction temperature of about 400°C for a second contact time of about 2 seconds to about 50 seconds; and producing a final product stream comprising trifluoroiodomethane, The molar ratio of the first trifluoroacetyl halide to the second trifluoroacetyl halide is about 0.6:1 to about 1.2:1. The catalyst may be platinum on a support, palladium on a support, activated carbon, silicon carbide, or a combination thereof. The second catalyst comprises about 0.3% to about 0.7% by weight of activated carbon or a carrier. Contains radium.

[0168] Embodiment 45 is a vapor phase process for producing trifluoroiodomethane, The process involves the reaction of hydrogen iodide with trifluoroacetyl chloride and trifluoroacetyl fluoride. fluoride, trifluoroacetyl bromide, and combinations thereof. and at least one trifluoroacetyl halide, and reacting the reactant stream in the presence of a first catalyst at a first reaction temperature of about 80°C to about 100°C for about 1 hour. At a pressure of 0 psig (69 kPaG) to approximately 150 psig (1,034 kPaG), The reaction is carried out for a first contact time of 5 seconds to about 35 seconds to produce a mixture containing trifluoroacetyl iodide. and heating the intermediate product stream in the presence of a second catalyst at about 300°C to reacting at a second reaction temperature of about 350°C for a second contact time of about 3 seconds to about 30 seconds; and producing a final product stream comprising trifluoroiodomethane, The molar ratio of the first trifluoroacetyl halide to the second trifluoroacetyl halide is about 0.7:1 to about 1.0:1. The catalyst may comprise platinum on a support, palladium on a support, silicon carbide, or a combination thereof. The second catalyst comprises activated carbon.

[0169] Embodiment 46 provides a process, wherein the reactant stream contains less than about 500 ppm by weight of oxygen. 48. The method of any one of embodiments 42-47, wherein the hydrogen iodide contains less than about 500 ppm by weight of water. This is the process.

[0170] Embodiment 47 provides a process wherein the reactant stream contains less than about 100 ppm by weight of oxygen. 48. The method of any one of embodiments 42-47, wherein the hydrogen iodide contains less than about 100 ppm by weight of water. This is the process.

[0171] Embodiment 48 provides a process wherein the reactant stream contains less than about 10 ppm by weight of oxygen. 48. The process of any one of embodiments 42 to 47, wherein the hydrogen iodide contains less than about 10 ppm by weight of water. It is a process.

[0172] Embodiment 49 is directed to a process comprising: a reactant stream comprising less than about 1 ppm by weight of oxygen; 48. The process of any one of embodiments 42 to 47, wherein the hydrogen iodide contains less than about 1 ppm by weight of water. It is.

[0173] Embodiment 50 is directed to a method for preparing a compound comprising the steps of: providing a compound in which the trifluoroacetyl halide is a trifluoroacetyl halide; The process of any one of embodiments 1 to 49, comprising acetyl chloride.

[0174] Aspect 51 is directed to a method for determining whether the organic compounds in the intermediate product stream are, in terms of GC area % of total organic compounds, About 10% to about 99% trifluoroacetyl iodide, about 1% to about 90% unreacted trifluoroacetyl iodide Fluoroacetyl halides, less than about 0.010% trifluoroiodomethane, and trifluoroisopropyl methyl ether. Fluoroacetyl iodide, trifluoroacetyl halide, and trifluoroiodomethane 51. The process of any one of aspects 1 to 50, comprising less than about 15% organic compounds other than tungsten. is.

[0175] Aspect 52 is directed to a method for determining whether the organic compounds in the intermediate product stream are, in terms of GC area % of total organic compounds, About 50% to about 99% trifluoroacetyl iodide, about 1% to about 50% unreacted trifluoroacetyl iodide Fluoroacetyl halides, less than about 0.002% trifluoroiodomethane, and trifluoroisopropyl methyl ether. Fluoroacetyl iodide, trifluoroacetyl halide, and trifluoroiodomethane 51. The process of any one of aspects 1 to 50, wherein the organic compound is less than about 8% other than ethanol. be.

[0176] Aspect 53 is directed to a method for determining whether the organic compounds in the intermediate product stream are, in terms of GC area % of total organic compounds, About 60% to about 99% trifluoroacetyl iodide, about 1% to about 40% unreacted trifluoroacetyl iodide Fluoroacetyl halides, less than about 0.001% trifluoroiodomethane, and trifluoroisopropyl methyl ether. Fluoroacetyl iodide, trifluoroacetyl halide, and trifluoroiodomethane 51. The process of any one of aspects 1 to 50, wherein the process comprises less than about 4% organic compounds other than tungsten. be.

[0177] Aspect 54 is directed to a method for determining whether the organic compounds in the intermediate product stream are, in terms of GC area % of total organic compounds, About 70% to about 99% trifluoroacetyl iodide, about 1% to about 30% unreacted trifluoroacetyl iodide less than about 0.0005% of trifluoroiodomethane, and Trifluoroacetyl iodide, trifluoroacetyl halide, and trifluoroiodine 51. The process of any one of aspects 1 to 50, comprising less than about 2% organic compounds other than methane. is.

[0178] Embodiment 55 provides an additional method for separating unreacted trifluoroacetyl halide from the intermediate product stream. and an additional step of returning the separated trifluoroacetyl halide to the reaction stream. An additional step of separating the reacted hydrogen iodide from the intermediate product stream and separating unreacted hydrogen iodide into the reactant stream. and an additional step of separating unreacted trifluoroacetyl iodide from the final product stream. and an additional step of returning the separated unreacted trifluoroacetyl iodide to the intermediate product stream. The process of any one of aspects 1 to 54, further comprising the steps of:

[0179] Embodiment 56 is a vapor phase process for producing trifluoroacetyl iodide, This process involves the use of hydrogen iodide and trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof. and at least one trifluoroacetyl halide selected from the group consisting of hydroxybenzoates, ... reacting the reactant stream in the presence of a first catalyst at a reaction temperature of about 25°C to about 400°C. and producing a product stream comprising trifluoroacetyl iodide.

[0180] In embodiment 57, in the step of reacting the reactant stream, the reaction temperature is about 40° C. to about 120° C. 57. The process of embodiment 56, wherein

[0181] In embodiment 58, in the step of reacting the reactant stream, the reaction temperature is about 70° C. to about 100° C. 57. The process of embodiment 56, wherein

[0182] In embodiment 59, in the step of reacting the reactant stream, the reaction temperature is about 80° C. to about 100° C. 57. The process of embodiment 56, wherein

[0183] Embodiment 60 provides a process wherein the reactant stream contains less than about 500 ppm by weight of oxygen. The process according to any one of embodiments 56 to 59 includes:

[0184] Embodiment 61 provides a process in which the reactant stream contains less than about 100 ppm by weight of oxygen. The process according to any one of embodiments 56 to 59 includes:

[0185] Embodiment 62 provides a process, wherein the reactant stream comprises less than about 10 ppm by weight of oxygen. 59. The process according to any one of embodiments 56 to 59.

[0186] Embodiment 63 provides a process, wherein the reactant stream comprises less than about 1 ppm by weight of oxygen. The process according to any one of embodiments 56 to 59.

[0187] Embodiment 64 relates to a method for preparing a hydrogen iodide solution, the method comprising the steps of: providing a hydrogen iodide solution containing less than about 500 ppm by weight of water; The process according to any one of embodiments 56 to 63 includes:

[0188] Embodiment 65 relates to a method for preparing a hydrogen iodide solution, the method comprising the steps of: providing a hydrogen iodide solution containing less than about 100 ppm by weight of water; The process according to any one of embodiments 56 to 63 includes:

[0189] Embodiment 66 relates to a method for preparing a hydrogen iodide solution, the method comprising the steps of: providing a hydrogen iodide solution containing less than about 10 ppm by weight of water; 64. The process according to any one of embodiments 56 to 63.

[0190] Embodiment 67 is directed to a method for preparing a hydrogen iodide solution, the method comprising the steps of: providing a solution containing hydrogen iodide; and The process according to any one of embodiments 56 to 63.

[0191] Embodiment 68 relates to a method for preparing a fluororesin comprising the steps of: reacting hydrogen iodide with a trifluoroacetyl halide; 68. The process according to any one of embodiments 56 to 67, wherein the molar ratio of It is.

[0192] Embodiment 69 relates to a method for preparing a fluororesin comprising the steps of: 68. The process according to any one of embodiments 56 to 67, wherein the molar ratio of It's Seth.

[0193] Embodiment 70 relates to a method for preparing a fluororesin comprising the steps of: 68. The process according to any one of embodiments 56 to 67, wherein the molar ratio of It's Seth.

[0194] Embodiment 71 is directed to a method for preparing a fluororesin comprising the steps of: reacting hydrogen iodide with a trifluoroacetyl halide; 68. The process according to any one of embodiments 56 to 67, wherein the molar ratio of It's Seth.

[0195] Embodiment 72 is directed to a method for reacting a reactant stream, the method comprising the steps of: Stainless steel, nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy, Nickel-copper alloy, copper, alumina, platinum, palladium, metal carbide, non-metal carbide, or The process according to any one of aspects 56 to 71 includes a combination thereof.

[0196] Embodiment 73 is directed to a method for preparing a catalyst comprising the steps of: activated carbon, mesocarbon, stainless steel, platinum on a support, or a catalyst on a support. Any of embodiments 56-71, comprising palladium, silicon carbide, or a combination thereof. The process is described in

[0197] Embodiment 74 is directed to a method for preparing a catalyst comprising the steps of: platinum on a support; palladium on a support; activated carbon; silicon carbide; or The process according to any one of aspects 56 to 71 includes a combination thereof.

[0198] Example 75 is the method of any one of Examples 56 to 71, wherein the catalyst comprises activated carbon or silicon carbide. This is the process described above.

[0199] In a seventeenth aspect, in the step of reacting the reactant stream, the reactant stream is reacted for about 0.1 seconds to about 30 seconds. 76. The process of any one of embodiments 56 to 75, wherein the catalyst may be contacted for a contact time of 0 seconds. be.

[0200] In a seventeenth aspect, in the step of reacting the reactant stream, the reactant stream is reacted for about 5 seconds to about 60 seconds. The process of any of embodiments 56 to 75, wherein the catalyst may be contacted for a contact time.

[0201] In embodiment 78, in the step of reacting the reactant stream, the reactant stream is reacted for about 10 seconds to about 40 seconds. 76. The process of any one of aspects 56 to 75, wherein the catalyst may be contacted for a contact time of .

[0202] In a seventy-ninth embodiment, in the step of reacting the reactant stream, the reactant stream is reacted for about 15 seconds to about 35 seconds. 76. The process of any one of aspects 56 to 75, wherein the catalyst may be contacted for a contact time of .

[0203] In embodiment 80, in the reacting step, the reactant stream is at a pressure of from about atmospheric pressure to about 300 psig ( 80. The process of any one of aspects 56 to 79, wherein the pressure is 2,068 kPaG. .

[0204] Embodiment 81 is directed to a method for reacting a reactant stream at a pressure of about 5 psig (34 kPaG). 79. Any of aspects 56 to 79, wherein the pressure is about 200 psig (1,379 kPaG). The process described is as follows:

[0205] Embodiment 82 is directed to a method for reacting a reactant stream at a pressure of about 10 psig (69 kPaG 79. Any of embodiments 56-79, wherein the pressure is between about 150 psig (1,034 kPaG) and about 150 psig (1,034 kPaG). The process is described in

[0206] Embodiment 83 relates to a method for reacting a reactant stream at a pressure of about 20 psig (138 kPa). 79. Any of aspects 56 to 79, wherein the pressure is from about 100 psig (689 kPaG) to about 100 psig (689 kPaG). The process described is as follows:

[0207] Embodiment 84 is a vapor phase process for producing trifluoroacetyl iodide, This process involves the use of hydrogen iodide and trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof. and at least one trifluoroacetyl halide selected from the group consisting of hydroxybenzoates, ... and subjecting the reactant stream to a reaction in the presence of a catalyst at a reaction temperature of about 25°C to about 400°C and at a pressure of about atmospheric to about At a pressure of 300 psig (2,068 kPaG), the contact time is approximately 0.1 seconds to approximately 300 seconds. reacting the mixture for a period of time to produce a product stream comprising trifluoroacetyl iodide. The molar ratio of hydrogen iodide to trifluoroacetyl halide is about 0.1:1 to about 10:1. The catalysts are activated carbon, mesocarbon, stainless steel, nickel, nickel-chromium alloy. Gold, nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, alumina, platinum, para The alloy may comprise a metal, a metal carbide, a non-metal carbide, or a combination thereof.

[0208] Embodiment 85 is a vapor phase process for producing trifluoroacetyl iodide, This process involves the use of hydrogen iodide and trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof. and at least one trifluoroacetyl halide selected from the group consisting of hydroxybenzoates, ... and subjecting the reactant stream to a pressure of about 5 psig at a reaction temperature of about 40°C to about 120°C in the presence of a catalyst. (34kPaG) to about 200 psig (1,379kPaG), for about 5 seconds to about 60 seconds reacting for a contact time of 1000 s to produce a product stream containing trifluoroacetyl iodide. and b. adding hydrogen iodide to trifluoroacetyl halide in a molar ratio of about 0.5: The ratio is 1 to about 2:1, and the catalyst is activated carbon, mesocarbon, stainless steel, platinum on a support, The material may comprise palladium, silicon carbide, or a combination thereof on a body.

[0209] Embodiment 86 is a vapor phase process for producing trifluoroacetyl iodide, This process involves the use of hydrogen iodide and trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof. and at least one trifluoroacetyl halide selected from the group consisting of hydroxybenzoates, ... and subjecting the reactant stream to a pressure of about 10 psi at a reaction temperature of about 70° C. to about 100° C. in the presence of a catalyst. g (69 kPaG) to approximately 150 psig (1,034 kPaG), for approximately 10 seconds to approximately The reaction was carried out for a contact time of 40 seconds to produce a product stream containing trifluoroacetyl iodide. and forming a trifluoroacetyl halide solution in a molar ratio of about 0. 6:1 to about 1.2:1, and the catalyst is platinum on a support, palladium on a support, activated carbon, carbon silicon dioxide, ...

[0210] Embodiment 87 is a vapor phase process for producing trifluoroacetyl iodide, This process involves the use of hydrogen iodide and trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof. and at least one trifluoroacetyl halide selected from the group consisting of hydroxybenzoates, ... and subjecting the reactant stream to a pressure of about 10 psi at a reaction temperature of about 80° C. to about 100° C. in the presence of a catalyst. g (69 kPaG) to approximately 150 psig (1,034 kPaG) for approximately 15 seconds to approximately The reaction was allowed to proceed for a contact time of 35 seconds to produce a product stream containing trifluoroacetyl iodide. and forming a trifluoroacetyl halide solution in a molar ratio of about 0. 7:1 to about 1.0:1, and the catalyst is platinum on a support, palladium on a support, silicon carbide, , or a combination thereof.

[0211] Embodiment 88 provides a process, wherein the reactant stream contains less than about 500 ppm by weight of oxygen. 88. The method of any one of embodiments 84-87, wherein the hydrogen iodide contains less than about 500 ppm by weight of water. This is the process.

[0212] Embodiment 89 provides a process, wherein the reactant stream contains less than about 100 ppm by weight of oxygen. 88. The method of any one of embodiments 84-87, wherein the hydrogen iodide contains less than about 100 ppm by weight of water. This is the process.

[0213] Embodiment 90 provides a process wherein the reactant stream comprises less than about 10 ppm by weight of oxygen. 88. The process of any one of embodiments 84 to 87, wherein the hydrogen iodide contains less than about 10 ppm by weight of water. It is a process.

[0214] Embodiment 91 provides a process wherein the reactant stream comprises less than about 1 ppm by weight of oxygen; 88. The process of any one of embodiments 84 to 87, wherein the hydrogen iodide contains less than about 1 ppm by weight of water. It is.

[0215] Embodiment 92 is directed to a method for preparing a compound comprising the steps of: The process of any one of embodiments 56 to 91, comprising acetyl chloride.

[0216] Embodiment 93 is a method for producing a fluoropolymer comprising at least 98% by weight of trifluoroacetyl iodide and chlorotrifluoroacetyl iodide. Fluoroethane, trifluoroacetyl chloride, iodotrifluoromethane, trifluoro difluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid, and chloroform A total of about 1 ppm to about 20,000 ppm of fluoromethane and fluoroisothiazolinone (about 2% by weight) of a compound.

[0217] Embodiment 94 is a method for producing a fluoropolymer comprising at least 99% by weight of trifluoroacetyl iodide and chlorotrifluoroacetyl iodide. Fluoroethane, trifluoroacetyl chloride, iodotrifluoromethane, trifluoro difluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid, and chloroform fluoromethane, and a total concentration of 1 ppm to 10,000 ppm (1 % by weight of a compound.

[0218] Embodiment 95 is a method for producing a fluoropolymer comprising at least 99.5% by weight of trifluoroacetyl iodide and chloroacetyl iodide. Trifluoroethane, trifluoroacetyl chloride, iodotrifluoromethane, trifluoromethane Fluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid, and chloro A total of 1 ppm to 5,000 ppm of a compound selected from the group consisting of fluorotrifluoromethane and fluoroisothiazolinone. and a compound.

[0219] Embodiment 96 is directed to a method for preparing a fluoropolymer comprising at least 99.7% by weight of trifluoroacetyl iodide and chloroacetyl iodide. Trifluoroethane, trifluoroacetyl chloride, iodotrifluoromethane, trifluoromethane Fluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid, and chloro a total of 1 ppm to 3,000 ppm selected from the group consisting of fluorotrifluoromethane, and a compound.

[0220] Embodiment 97 is a method for producing a fluoropolymer comprising at least 98% by weight of trifluoroacetyl iodide and chlorotrifluoroacetyl iodide. Fluoroethane, trifluoroacetyl chloride, iodotrifluoromethane, trifluoro difluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid, and chloroform A total of about 1 ppm to about 20,000 ppm of fluoromethane and fluoroisothiazolinone (about 2% by weight) of the compound.

[0221] Embodiment 98 is a method for producing a fluoropolymer comprising at least 99% by weight of trifluoroacetyl iodide and chlorotrifluoroacetyl iodide. Fluoroethane, trifluoroacetyl chloride, iodotrifluoromethane, trifluoro difluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid, and chloroform fluoromethane, and a total concentration of 1 ppm to 10,000 ppm (1 % by weight of a compound.

[0222] Embodiment 99 is a method for producing a fluoropolymer comprising at least 99.5% by weight of trifluoroacetyl iodide and chloroacetyl iodide. Trifluoroethane, trifluoroacetyl chloride, iodotrifluoromethane, trifluoromethane Fluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid, and chloro A total of 1 ppm to 5,000 ppm of a compound selected from the group consisting of fluorotrifluoromethane and fluoroisothiazolinone. and a composition consisting essentially of a compound.

[0223] Embodiment 100 is a method for producing a fluoropolymer comprising at least 99.7% by weight of trifluoroacetyl iodide and chloroacetyl iodide. Iodotrifluoroethane, trifluoroacetyl chloride, iodotrifluoromethane, trifluoromethane Trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid, and A total of 1 ppm to 3,000 ppm of fluoroisothiazolinone, selected from the group consisting of chlorotrifluoromethane and chlorotrifluoromethane. and a composition consisting essentially of the compound:

[0224] Embodiment 101 is a method for preparing a fluoropolymer comprising at least 98% by weight of trifluoroacetyl iodide and chloroacetyl iodide. Trifluoroethane, trifluoroacetyl chloride, iodotrifluoromethane, trifluoro fluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid, and chloro trifluoromethane, and a total of about 1 ppm to about 20,000 ppm m (about 2% by weight) of the compound.

[0225] Embodiment 102 is a method for preparing a fluoropolymer comprising at least 99% by weight of trifluoroacetyl iodide and chloroacetyl iodide. Trifluoroethane, trifluoroacetyl chloride, iodotrifluoromethane, trifluoro fluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid, and chloro trifluoromethane, and 1% by weight of the compound.

[0226] Embodiment 103 is a method for producing a fluoropolymer comprising at least 99.5% by weight trifluoroacetyl iodide and chloroacetyl iodide. Iodotrifluoroethane, trifluoroacetyl chloride, iodotrifluoromethane, trifluoromethane Trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid, and A total of 1 ppm to 5,000 ppm of fluoroisothiazolinone, selected from the group consisting of chlorotrifluoromethane and chlorotrifluoromethane. and a composition comprising the compound:

[0227] Embodiment 104 is a method for producing a fluoropolymer comprising at least 99.7% by weight trifluoroacetyl iodide and chloroacetyl iodide. Iodotrifluoroethane, trifluoroacetyl chloride, iodotrifluoromethane, trifluoromethane Trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid, and A total of 1 ppm to 3,000 ppm of fluoroisothiazolinone, selected from the group consisting of chlorotrifluoromethane and chlorotrifluoromethane. and a composition comprising the compound:

[0228] Embodiment 105 is a method for preparing a fluororesin comprising at least 99% by weight trifluoroiodomethane and 1 ppm to 5 ppm trifluoroiodomethane. 00 ppm of chlorotrifluoroethane and less than 500 ppm of hexafluoroethane , less than 500 ppm trifluoromethane, less than 100 ppm carbon monoxide, and 1 pp Less than m of hydrogen chloride and trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetaldehyde, and trifluoroacetyl chloride and a total of 1 ppm to 500 ppm of compounds that are contained in the composition.

[0229] Embodiment 106 is directed to a method for preparing a fluororesin comprising at least 99.5% by weight trifluoroiodomethane and 1 ppm ~250 ppm chlorotrifluoroethane and less than 250 ppm hexafluoroethane fluorine, less than 250 ppm trifluoromethane, less than 50 ppm carbon monoxide, and 0. Less than 5 ppm of hydrogen chloride, trifluoroacetyl fluoride, hexafluoropropanoic acid from the group consisting of acetaldehyde, trifluoroacetaldehyde, and trifluoroacetyl chloride and a total of 1 ppm to 250 ppm of the selected compounds.

[0230] Embodiment 107 is directed to a method for preparing a fluororesin comprising at least 99.7% by weight trifluoroiodomethane and 1 ppm ~100 ppm chlorotrifluoroethane and less than 100 ppm hexafluoroethane fluorine, less than 100 ppm trifluoromethane, less than 20 ppm carbon monoxide, and 0. Less than 2 ppm of hydrogen chloride, trifluoroacetyl fluoride, hexafluoropropanoic acid from the group consisting of acetaldehyde, trifluoroacetaldehyde, and trifluoroacetyl chloride and a total of 1 ppm to 100 ppm of the selected compounds.

[0231] Embodiment 108 is directed to a method for preparing a fluororesin comprising at least 99.9% by weight trifluoroiodomethane and 1 ppm ~100 ppm chlorotrifluoroethane and less than 100 ppm hexafluoroethane fluorine, less than 100 ppm trifluoromethane, less than 20 ppm carbon monoxide, and 0. Less than 2 ppm of hydrogen chloride, trifluoroacetyl fluoride, hexafluoropropanoic acid from the group consisting of acetaldehyde, trifluoroacetaldehyde, and trifluoroacetyl chloride and a total of 1 ppm to 100 ppm of the selected compounds.

[0232] Embodiment 109 is a method for preparing a fluororesin comprising at least 99% by weight trifluoroiodomethane and 1 ppm to 5 ppm trifluoroiodomethane. 00 ppm of chlorotrifluoroethane and less than 500 ppm of hexafluoroethane , less than 500 ppm trifluoromethane, less than 100 ppm carbon monoxide, and 1 pp Less than m of hydrogen chloride and trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetaldehyde, and trifluoroacetyl chloride The composition essentially consists of compounds that are present in an amount of 1 ppm to 500 ppm in total.

[0233] Embodiment 110 is a method for preparing a fluororesin comprising at least 99.5% by weight trifluoroiodomethane and 1 ppm ~250 ppm chlorotrifluoroethane and less than 250 ppm hexafluoroethane fluorine, less than 250 ppm trifluoromethane, less than 50 ppm carbon monoxide, and 0. Less than 5 ppm of hydrogen chloride, trifluoroacetyl fluoride, hexafluoropropanoic acid from the group consisting of acetaldehyde, trifluoroacetaldehyde, and trifluoroacetyl chloride and a total of 1 ppm to 250 ppm of a compound selected from the group consisting of: .

[0234] Embodiment 111 is a method for preparing a fluororesin comprising at least 99.7% by weight trifluoroiodomethane and 1 ppm ~100 ppm chlorotrifluoroethane and less than 100 ppm hexafluoroethane fluorine, less than 100 ppm trifluoromethane, less than 20 ppm carbon monoxide, and 0. Less than 2 ppm of hydrogen chloride, trifluoroacetyl fluoride, hexafluoropropanoic acid from the group consisting of acetaldehyde, trifluoroacetaldehyde, and trifluoroacetyl chloride and a total of 1 ppm to 100 ppm of a compound selected from the group consisting of: .

[0235] Embodiment 112 is directed to a method for preparing a fluororesin comprising at least 99.9% by weight trifluoroiodomethane and 1 ppm ~100 ppm chlorotrifluoroethane and less than 100 ppm hexafluoroethane fluorine, less than 100 ppm trifluoromethane, less than 20 ppm carbon monoxide, and 0. Less than 2 ppm of hydrogen chloride, trifluoroacetyl fluoride, hexafluoropropanoic acid from the group consisting of acetaldehyde, trifluoroacetaldehyde, and trifluoroacetyl chloride and a total of 1 ppm to 100 ppm of a compound selected from the group consisting of: .

[0236] Embodiment 109 is a method for preparing a fluororesin comprising at least 99% by weight trifluoroiodomethane and 1 ppm to 5 ppm trifluoroiodomethane. 00 ppm of chlorotrifluoroethane and less than 500 ppm of hexafluoroethane , less than 500 ppm trifluoromethane, less than 100 ppm carbon monoxide, and 1 pp Less than m of hydrogen chloride and trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetaldehyde, and trifluoroacetyl chloride The composition is composed of a total of 1 ppm to 500 ppm of compounds.

[0237] Embodiment 110 is a method for preparing a fluororesin comprising at least 99.5% by weight trifluoroiodomethane and 1 ppm ~250 ppm chlorotrifluoroethane and less than 250 ppm hexafluoroethane fluorine, less than 250 ppm trifluoromethane, less than 50 ppm carbon monoxide, and 0. Less than 5 ppm of hydrogen chloride, trifluoroacetyl fluoride, hexafluoropropanoic acid from the group consisting of acetaldehyde, trifluoroacetaldehyde, and trifluoroacetyl chloride and a total of 1 ppm to 250 ppm of selected compounds.

[0238] Embodiment 111 is a method for preparing a fluororesin comprising at least 99.7% by weight trifluoroiodomethane and 1 ppm ~100 ppm chlorotrifluoroethane and less than 100 ppm hexafluoroethane fluorine, less than 100 ppm trifluoromethane, less than 20 ppm carbon monoxide, and 0. Less than 2 ppm of hydrogen chloride, trifluoroacetyl fluoride, hexafluoropropanoic acid from the group consisting of acetaldehyde, trifluoroacetaldehyde, and trifluoroacetyl chloride and a total of 1 ppm to 100 ppm of selected compounds.

[0239] Embodiment 112 is directed to a method for preparing a fluororesin comprising at least 99.9% by weight trifluoroiodomethane and 1 ppm ~100 ppm chlorotrifluoroethane and less than 100 ppm hexafluoroethane fluorine, less than 100 ppm trifluoromethane, less than 20 ppm carbon monoxide, and 0. Less than 2 ppm of hydrogen chloride, trifluoroacetyl fluoride, hexafluoropropanoic acid from the group consisting of acetaldehyde, trifluoroacetaldehyde, and trifluoroacetyl chloride and a total of 1 ppm to 100 ppm of selected compounds.

[0240] Embodiment 113 is a vapor phase process for producing trifluoroiodomethane, The process comprises the steps of providing a reactant stream comprising trifluoroacetyl iodide; The stream is reacted in the presence of a catalyst at a reaction temperature of about 200°C to about 600°C to form trifluoroiodo. and producing a product stream comprising methyl methane.

[0241] In embodiment 114, in the step of reacting the reactant stream, the reaction temperature is from about 250° C. to about 50° C. 114. The process of claim 113, wherein the temperature is 0° C.

[0242] In embodiment 115, in the step of reacting the reactant stream, the reaction temperature is about 300° C. to about 40° C. 114. The process of claim 113, wherein the temperature is 0° C.

[0243] In embodiment 116, in the step of reacting the reactant stream, the reaction temperature is from about 300° C. to about 35° C. 114. The process of claim 113, wherein the temperature is 0° C.

[0244] In embodiment 117, in the step of reacting the reactant stream, the reactant stream is reacted for about 0.1 seconds to about 3 seconds. 117. The process according to any one of embodiments 113 to 116, wherein the process may be contacted with the catalyst for a contact time of 0.5 seconds. It's Seth.

[0245] In embodiment 118, in the step of reacting the reactant stream, the reactant stream is reacted for about 1 second to about 60 seconds. 117. The process of any one of embodiments 113 to 116, wherein the catalyst may be contacted for a contact time of be.

[0246] In embodiment 119, in the step of reacting the reactant stream, the reactant stream is reacted for about 2 seconds to about 50 seconds. 117. The process of any one of embodiments 113 to 116, wherein the catalyst may be contacted for a contact time of be.

[0247] In embodiment 120, in the step of reacting the reactant stream, the reactant stream is reacted for about 3 seconds to about 30 seconds. 117. The process of any one of embodiments 113 to 116, wherein the catalyst may be contacted for a contact time of be.

[0248] Embodiment 121 describes a method for reacting a reactant stream, the method comprising the steps of: Nickel-chromium alloy, nickel-chromium-molybdenum alloy, nickel-copper alloy, copper , alumina, silicon carbide, platinum, palladium, rhenium, activated carbon, mesocarbon, or The process according to any one of embodiments 113 to 120 includes a combination of these.

[0249] Embodiment 122 describes a method for reacting a reactant stream, the method comprising the steps of: (a) reacting a reactant stream with a catalyst; (b) reacting a reactant stream with a catalyst; and (c) reacting a reactant stream with a catalyst. 0.1% to about 1% by weight of platinum, about 0.1% to about 1% by weight of palladium on a support, 1. A method for treating a skin condition comprising administering to a subject a composition comprising: administering to a subject a composition comprising: about 0.1% to about 1% by weight of rhenium on a body surface; 13 to 120.

[0250] Embodiment 123 relates to a method for reacting a reactant stream, the method comprising the steps of: (a) reacting a reactant stream with a catalyst; (b) reacting a reactant stream with a catalyst; and (c) reacting a reactant stream with a catalyst. Any of embodiments 113-120, comprising about 0.3 wt.% to about 0.7 wt.% palladium. The process described is as follows:

[0251] Embodiment 124 is the process of embodiment 11, wherein in the step of reacting the reactant stream, the catalyst comprises activated carbon. 3 to 120.

[0252] Embodiment 125 is directed to a process for reacting a reactant stream, wherein a catalyst is present in a reaction zone contacting the reactant stream. 121. The process of any one of embodiments 113 to 120, wherein the surface of the reactor is

[0253] Embodiment 126 relates to a method for reacting a reactant stream, the method comprising: reacting a reactant stream at a pressure of from about 5 psig (34 kPaG) to about 3 125. The method of claim 113, wherein the pressure is 0.00 psig (2,068 kPaG). This is the process described above.

[0254] Embodiment 127 is a vapor phase process for producing trifluoroiodomethane, The process comprises the steps of providing a reactant stream comprising trifluoroacetyl iodide; The flow is heated in the presence of a catalyst at a reaction temperature of about 200°C to about 600°C for about 0.1 seconds to about 300 seconds. reacting for a contact time to produce a product stream comprising trifluoroiodomethane; and , and the catalyst is stainless steel, nickel, nickel-chromium alloy, nickel-chromium -Molybdenum alloy, nickel-copper alloy, copper, alumina, silicon carbide, platinum, palladium, The material may include rhenium, activated carbon, mesocarbon, or a combination thereof.

[0255] Embodiment 128 is a vapor phase process for producing trifluoroiodomethane, The process comprises the steps of providing a reactant stream comprising trifluoroacetyl iodide; The flow is contacted in the presence of a catalyst at a reaction temperature of about 250°C to about 500°C for about 1 second to about 60 seconds. reacting the mixture for a period of time to produce a product stream comprising trifluoroiodomethane. The catalyst comprises activated carbon, about 0.1% to about 1% by weight of platinum on a support, and about 0.1% by weight of platinum on a support. % to about 1% by weight of palladium, about 0.1% to about 1% by weight of rhenium on a support, or This includes combinations of these.

[0256] Embodiment 129 is a vapor phase process for producing trifluoroiodomethane, The process comprises the steps of providing a reactant stream comprising trifluoroacetyl iodide; The flow is contacted in the presence of a catalyst at a reaction temperature of about 300°C to about 400°C for about 2 seconds to about 50 seconds. reacting the mixture for a period of time to produce a product stream comprising trifluoroiodomethane. The catalyst comprises about 0.3% to about 0.7% by weight of palladium on an activated carbon or support. .

[0257] Embodiment 130 is a vapor phase process for producing trifluoroiodomethane, the process including: providing a reactant stream comprising trifluoroacetyl iodide; and reacting the reactant stream in the presence of a catalyst at a reaction temperature of about 300° C. to about 350° C. for a contact time of about 3 seconds to about 30 seconds to produce a product stream comprising trifluoroiodomethane, wherein the catalyst comprises activated carbon. The present specification includes the following aspects of the invention. [1] 1. A vapor phase process for producing trifluoroiodomethane, comprising: providing a reactant stream comprising hydrogen iodide and at least one trifluoroacetyl halide selected from the group consisting of trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof; reacting the reactant stream in the presence of a first catalyst at a first reaction temperature of about 25°C to about 400°C to produce an intermediate product stream comprising trifluoroacetyl iodide; reacting the intermediate product stream in the presence of a second catalyst at a second reaction temperature of from about 200°C to about 600°C to produce a final product stream comprising trifluoroiodomethane. [2] The treatment method according to [1], wherein in the step of reacting the reactant flow, the first reaction temperature is about 40°C to about 120°C. [3] 10. The method of claim 1, wherein in the providing step, the reactant stream contains less than about 500 ppm by weight of oxygen, and the hydrogen iodide contains less than about 500 ppm by weight of water. [4] 10. The process of claim 1, wherein in the step of reacting the reactant stream, the first catalyst comprises activated carbon, mesocarbon, stainless steel, nickel, a nickel-chromium alloy, a nickel-chromium-molybdenum alloy, a nickel-copper alloy, copper, alumina, platinum, palladium, a metal carbide, a non-metal carbide, or a combination thereof. [5] 10. The method of claim 1, wherein in the step of reacting the intermediate product stream, the second catalyst comprises stainless steel, nickel, a nickel-chromium alloy, a nickel-chromium-molybdenum alloy, a nickel-copper alloy, copper, alumina, silicon carbide, platinum, palladium, rhenium, activated carbon, mesocarbon, or a combination thereof. [6] The processing method according to [1], wherein in the step of reacting the intermediate product stream, the second reaction temperature is about 250°C to about 500°C. [7] The treatment method according to [1], wherein the organic compounds in the intermediate product stream contain, in GC area % of all organic compounds, about 10% to about 99% trifluoroacetyl iodide, about 1% to about 90% unreacted trifluoroacetyl halide, less than about 0.010% trifluoroiodomethane, and less than about 15% organic compounds other than trifluoroacetyl iodide, trifluoroacetyl halide, and trifluoroiodomethane. [8] the additional step of separating unreacted trifluoroacetyl halide from said intermediate product stream; the additional step of returning said separated trifluoroacetyl halide to said reactant stream; the additional step of separating unreacted hydrogen iodide from said intermediate product stream; the additional step of returning said unreacted hydrogen iodide to said reactant stream; an additional step of separating unreacted trifluoroacetyl iodide from said final product stream; The method of claim 1, further comprising the additional step of returning the separated unreacted trifluoroacetyl iodide to the intermediate product stream. [9] 1. A composition comprising: At least 99% by weight of trifluoroiodomethane 1 ppm to 500 ppm of chlorotrifluoroethane, less than 500 ppm of hexafluoroethane; Less than 500 ppm of trifluoromethane; Less than 100 ppm of carbon monoxide, and less than 1 ppm hydrogen chloride.

[10] The composition according to [9], further comprising a compound selected from the group consisting of trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetaldehyde, and trifluoroacetyl chloride in a total amount of 1 ppm to 500 ppm.

Claims

1. 1. A vapor phase manufacturing process for producing trifluoroiodomethane, comprising: providing a reactant stream comprising hydrogen iodide and trifluoroacetyl chloride; reacting the reactant stream in the presence of a first catalyst at a first reaction temperature of from 25°C to 120°C to produce an intermediate product stream comprising trifluoroacetyl iodide; reacting the intermediate product stream at a second reaction temperature of from 200°C to 600°C to produce a final product stream comprising trifluoroiodomethane; The method of manufacturing, wherein in the step of reacting the reactant stream, the first catalyst comprises activated carbon or silicon carbide, and the reactant stream contacts the first catalyst for a contact time of from 0.1 seconds to 300 seconds.

2. Trifluoroacetyl iodide (CF ３ 1. A vapor phase manufacturing method for producing COI, comprising: providing a reactant stream comprising hydrogen iodide and trifluoroacetyl chloride; reacting the reactant stream in the presence of a catalyst at a reaction temperature of 25°C to 120°C to produce a product stream comprising the trifluoroacetyl iodide; The method of manufacturing, wherein in the step of reacting the reactant stream, the catalyst comprises activated carbon or silicon carbide, and the reactant stream contacts the catalyst for a contact time of from 0.1 seconds to 300 seconds.

3. 2. The process of claim 1, wherein in said providing step, said reactant stream contains less than 500 ppm by weight of oxygen and said hydrogen iodide contains less than 500 ppm by weight of water.

4. 2. The method according to claim 1, wherein in the providing step, the molar ratio of hydrogen iodide to trifluoroacetyl chloride is 0.1:1 to 10:

1.

5. 10. The process of claim 1, wherein in the reacting step, the reactant stream is at a pressure from atmospheric to 300 psig (2,068 kPaG).

6. 10. The process of claim 1, wherein in the step of reacting the intermediate product stream, the intermediate product stream is contacted with the second catalyst for a contact time of from 0.1 seconds to 300 seconds.

7. 7. The process of claim 6, wherein in the step of reacting the intermediate product stream, the second catalyst comprises stainless steel, nickel, a nickel-chromium alloy, a nickel-chromium-molybdenum alloy, a nickel-copper alloy, copper, alumina, silicon carbide, platinum, palladium, rhenium, activated carbon, mesocarbon, or a combination thereof.

8. 2. The process of claim 1, wherein in the step of reacting the intermediate product stream, the second reaction temperature is from 250°C to 500°C.

9. The method of claim 1, wherein the organic compounds in the intermediate product stream comprise, in GC area % of all organic compounds, 65.66% to 87.22% trifluoroacetyl iodide, 9.01% to 31.57% unreacted trifluoroacetyl chloride, and 0.0014% or less trifluoroiodomethane.

10. 3. The process of claim 2, wherein in the step of reacting the reactant streams, the reaction temperature is from 40°C to 120°C.

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