Process for producing trifluoroiodomethane and trifluoroacetyl iodide

Abstract

The present application relates to a process for the production of trifluoroiodomethane and trifluoroacetyl iodide. The present disclosure provides a process for the production of trifluoroiodomethane, the process 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 at a first reaction temperature from about 25 DEG C to about 400 DEG C in the presence of a first catalyst to produce an intermediate product stream comprising trifluoroacetyl iodide; and reacting the intermediate product stream at a second reaction temperature of about 200 DEG C to about 600 DEG C in the presence of a second catalyst to produce a final product stream comprising the trifluoroiodomethane.

Description

[0001] This application is a divisional application of the invention patent application with the application date of August 23, 2019, application number 201980061993.4, and name “Method for Producing Trifluoroiodomethane and Trifluoroacetyl Iodide”. Technical Field

[0002] The present disclosure relates to a method for producing trifluoroiodomethane (CF3I) and trifluoroacetyl iodide (CF3COI). Specifically, the present disclosure relates to a gas phase method for producing trifluoroiodomethane and trifluoroacetyl iodide. Background Art

[0003] Trifluoroacetyl iodide (CF3COI) is a compound that can be converted to trifluoroiodomethane (CF3I). Trifluoroiodomethane (CF3I), also known as perfluoromethyl iodide, trifluoromethyl iodide or iodotrifluoromethane, is a compound that can be used in commercial applications as, for example, a refrigerant or fire extinguishing agent. Trifluoroiodomethane is a low global warming potential molecule with negligible ozone depletion potential. Trifluoroiodomethane can replace more environmentally harmful substances.

[0004] Methods for preparing trifluoroacetyl iodide are known. For example, the article "The Reactions of Metallic Salts of Acids with Halogens. Part I. The Reaction of Metal Trifluoroacetates with Iodine, Bromine, and Chlorine," RN Haszeldine, Journal of the Chemical Society, pp. 584-587 (1951) describes the batch reaction of trifluoroacetyl chloride and anhydrous hydrogen iodide at 120° C. for 8 hours without a catalyst to produce trifluoroacetyl iodide in a yield of about 62%. The low yield and long reaction time make it very inefficient.

[0005] U.S. Pat. No. 7,196,236 (Mukhopadhyay et al.) discloses a catalytic process for producing trifluoroiodomethane using reactants comprising an iodine source, at least a stoichiometric amount of oxygen, and a reactant CF3R (wherein R is selected from: -COOH, -COX, -CHO, -COOR2, and -SO2X, where R2 is an alkyl group, and X is chlorine, bromine, or iodine. The hydrogen iodide that may be produced by the reaction may be oxidized by at least a stoichiometric amount of oxygen to produce water and iodine for economical recycling.

[0006] U.S. Pat. No. 7,132,578 (Mukhopadhyay et al.) also discloses a one-step catalytic process for producing trifluoroiodomethane from trifluoroacetyl chloride. However, the source of iodine is iodine fluoride (IF). Compared with hydrogen iodide, iodine fluoride is relatively unstable and decomposes into I2 and IF5 above 0°C. Iodine fluoride may also not be available in commercially available quantities.

[0007] Some known methods for preparing trifluoroacetyl iodide include liquid phase processes. Liquid phase processes may require that the solvent must be separated and disposed of. The additional steps required for separation and disposal make the process less efficient.

[0008] Therefore, there is a need to develop a more efficient process that can be scaled up to produce commercial quantities of trifluoroiodomethane from relatively inexpensive starting materials. Summary of the invention

[0009] The present disclosure provides a gas phase process for producing trifluoroiodomethane (CF3I) and trifluoroacetyl iodide (CF3COI).

[0010] In one embodiment, the present invention provides a gas phase method for producing trifluoroiodomethane. The method comprises: providing a reactant stream comprising hydrogen iodide and at least one trifluoroacetyl halide, wherein the trifluoroacetyl halide is selected from the group consisting of trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof; reacting the reactant stream at a first reaction temperature of about 25°C to about 400°C in the presence of a first catalyst to produce an intermediate product stream comprising trifluoroacetyl iodide; and reacting the intermediate product stream at a second reaction temperature of about 200°C to about 600°C in the presence of a second catalyst to produce a final product stream comprising the trifluoroiodomethane.

[0011] In another embodiment, the present invention provides a gas phase method for producing trifluoroacetyl iodide. The method comprises: providing a reactant stream comprising hydrogen iodide and at least one trifluoroacetyl halide, the trifluoroacetyl halide being selected from the group consisting of trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof; and reacting the reactant stream at a reaction temperature of about 25° C. to about 400° C. in the presence of a first catalyst to produce a product stream comprising trifluoroacetyl iodide.

[0012] In another embodiment, the present invention provides a composition comprising at least 98 weight percent trifluoroacetyl iodide and a total of about 1 ppm to about 20,000 ppm (about 2 weight percent) of a compound selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane.

[0013] In another embodiment, the present invention provides a composition comprising at least 99 wt % 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, less than 1 ppm of hydrogen chloride, and a total of 1 ppm to 500 ppm of a compound selected from the group consisting of trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde, and trifluoroacetyl chloride.

[0014] In another embodiment, the present invention provides a gas phase method for producing trifluoroiodomethane. The method comprises: providing a reactant stream comprising trifluoroacetyl iodide; and reacting the reactant stream at a reaction temperature of about 200° C. to about 600° C. in the presence of a catalyst to produce a product stream comprising the trifluoroiodomethane.

[0015] This application may include the following technical solutions.

[0016] Scheme 1. A gas phase method for producing trifluoroiodomethane, the method comprising:

[0017] 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;

[0018] reacting the reactant stream at a first reaction temperature of about 25° C. to about 400° C. in the presence of a first catalyst to produce an intermediate product stream comprising trifluoroacetyl iodide; and

[0019] The intermediate product stream is reacted at a second reaction temperature of about 200°C to about 600°C in the presence of a second catalyst to produce a final product stream comprising the trifluoroiodomethane.

[0020] Scheme 2. The method according to Scheme 1, wherein in the step of reacting the reactant stream, the first reaction temperature is about 40°C to about 120°C.

[0021] Option 3. A method according to Option 1, wherein in the providing step, the reactant flow contains less than about 500 ppm by weight of oxygen, and the hydrogen iodide contains less than about 500 ppm by weight of water.

[0022] Option 4. A method according to Option 1, wherein in the step of reacting the reactant flow, the first catalyst comprises activated carbon, mesophase carbon, stainless steel, nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, alumina, platinum, palladium, metal carbide, non-metal carbide or a combination thereof.

[0023] Option 5. A method according to Option 1, wherein in the step of reacting the intermediate product stream, the second catalyst comprises stainless steel, nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, alumina, silicon carbide, platinum, palladium, rhenium, activated carbon, mesophase carbon or a combination thereof.

[0024] Option 6. The method according to Option 1, wherein in the step of reacting the intermediate product stream, the second reaction temperature is about 250°C to about 500°C.

[0025] Scheme 7. A method according to Scheme 1, wherein the organic compounds in the intermediate product stream contain, based on the GC area % of total organic compounds, about 10% to about 99% of trifluoroacetyl iodide, about 1% to about 90% of unreacted trifluoroacetyl halide, less than about 0.010% of trifluoroiodomethane, and less than about 15% of organic compounds other than trifluoroacetyl iodide, trifluoroacetyl halide and trifluoroiodomethane.

[0026] Scheme 8. The method according to Scheme 1 further comprises the following additional steps:

[0027] separating unreacted trifluoroacetyl halide from the intermediate product stream;

[0028] returning the separated trifluoroacetyl halide to the reaction stream;

[0029] separating unreacted hydrogen iodide from the intermediate product stream;

[0030] returning the unreacted hydrogen iodide to the reactant stream;

[0031] separating unreacted trifluoroacetyl iodide from the final product stream; and

[0032] The separated unreacted trifluoroacetyl iodide is returned to the intermediate product stream.

[0033] Embodiment 9. A composition comprising:

[0034] at least 99% by weight of trifluoroiodomethane;

[0035] 1 ppm to 500 ppm of chlorotrifluoroethane;

[0036] Less than 500 ppm of hexafluoroethane;

[0037] Less than 500 ppm of trifluoromethane;

[0038] Less than 100 ppm carbon monoxide; and

[0039] Less than 1ppm of hydrogen chloride.

[0040] Embodiment 10. The composition according to embodiment 9 further comprises:

[0041] 1 ppm to 500 ppm in total of a compound selected from the group consisting of trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde and trifluoroacetyl chloride.

[0042] The above and other features of the present disclosure and the manner of achieving the same will become more apparent and will be better understood by referring to the following description of the embodiments in conjunction with the accompanying drawings. BRIEF DESCRIPTION OF THE DRAWINGS

[0043] Figure 1 FIG. 1 is a process flow diagram showing a gas phase method for producing trifluoroacetyl iodide.

[0044] Figure 2 is a process flow diagram showing a two-step gas phase process for making trifluoroiodomethane.

[0045] Figure 3 The following is a process flow chart showing a gas phase method for producing trifluoroiodomethane from trifluoroacetyl iodide. DETAILED DESCRIPTION

[0046] The disclosure provides a method for making trifluoroiodomethane and trifluoroacetyl iodide, which produces surprisingly good process yields starting from hydrogen, iodine and trifluoroacetyl halide (such as trifluoroacetyl chloride). Such starting materials are relatively cheap and easy to obtain in commercial quantities. The disclosed method can be a high-yield gas phase method suitable for making trifluoroiodomethane and trifluoroacetyl iodide on a commercial scale. The disclosed gas phase method does not require a solvent, thereby further enhancing their commercial appeal.

[0047] As disclosed herein, trifluoroiodomethane and trifluoroacetyl iodide are produced from a reactant stream comprising hydrogen iodide (HI) and trifluoroacetyl halide (CFCOX, X=Cl, Br or F). The hydrogen iodide and trifluoroacetyl halide are anhydrous. It is preferred that the amount of water in the reactant stream be as small as possible, because any water in the reactant stream can hydrolyze some of the trifluoroacetyl halide and form the thermodynamically more favorable trifluoroacetic acid rather than the desired trifluoroacetyl iodide.

[0048] Anhydrous hydrogen iodide is substantially free of water. That is, the amount of any water in anhydrous hydrogen iodide is less than about 500ppm, about 300ppm, about 200ppm, about 100ppm, about 50ppm, about 30ppm, about 20ppm, about 10ppm, about 5ppm, about 3ppm, about 2ppm or about 1ppm by weight, or less than any value limited between any two aforementioned values. Preferably, anhydrous hydrogen iodide comprises water less than about 100ppm by weight. More preferably, anhydrous hydrogen iodide comprises water less than about 10ppm by weight. Most preferably, anhydrous hydrogen iodide comprises water less than about 1ppm by weight.

[0049] The reaction stream is substantially free of oxygen. That is, the amount of any oxygen in the reaction stream is less than about 500ppm, about 300ppm, about 200ppm, about 100ppm, about 50ppm, about 30ppm, about 20ppm, about 10ppm, about 5ppm, about 3ppm, about 2ppm or about 1ppm by weight, or less than any value limited between any two aforementioned values. Preferably, the amount of oxygen in the reaction stream is less than about 100ppm by weight. More preferably, the amount of oxygen in the reaction stream is less than about 10ppm by weight. Most preferably, the amount of oxygen in the reaction stream is less than about 1ppm by weight. Preferably, the oxygen in the reaction stream is as little as possible, because before hydrogen iodide can react to form trifluoroacetyl iodide, any oxygen in the reaction stream can oxidize at least some hydrogen iodide to form iodine and water. Even if it is operated together with excess hydrogen iodide, the formed water can also hydrolyze trifluoroacetyl halide and form thermodynamically more favorable trifluoroacetic acid, rather than required trifluoroiodomethane, thereby reducing process efficiency.

[0050] At least one trifluoroacetyl halide is selected from: trifluoroacetyl fluoride (CF3COF), trifluoroacetyl chloride (CF3COCl), trifluoroacetyl bromide (CF3COBr) and any combination thereof. Preferably, at least one trifluoroacetyl halide comprises trifluoroacetyl chloride. More preferably, at least one trifluoroacetyl halide consists essentially of trifluoroacetyl chloride. Most preferably, at least one trifluoroacetyl halide consists of trifluoroacetyl chloride.

[0051] For example, trifluoroacetyl chloride is readily available in commercial quantities from Sigma-Aldrich Corp., St. Louis, Missouri, Halocarbon Products Corporation, Peachtree Corners, Georgia, or Solvay SA, Brussels, Belgium. Hydrogen iodide is commercially available or can be made by, for example, reacting elemental iodine with hydrazine, distilling it from a solution of sodium iodide and phosphoric acid, or irradiating a mixture of hydrogen and elemental iodine at a wavelength of about 578 nanometers.

[0052] The molar ratio of hydrogen iodide to trifluoroacetyl halide in the reactant stream can be as low as about 0.1:1, about 0.2:1, about 0.3:1, about 0.4:1, about 0.5:1, about 0.6:1, about 0.7:1, about 0.8:1, about 0.9:1, about 0.95:1, about 0.99:1, or about 1:1, or as high as about 1.01:1, about 1.05:1, about 1.1:1, about 1.2:1, about 1.3:1, about 1.4:1, about 1.5:1, about 1.6:1, about 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 in any range defined between any two of the foregoing values, such as, for example, about 0.1:1 to about The invention relates to a method for preparing an aqueous solution of at least one embodiment of the present invention, wherein the aqueous solution comprises at least one amine and at least one amine group. The aqueous solution comprises at least one amine group, wherein the aqueous solution comprises at least one amine group, wherein the aqueous solution comprises at least one amine group, wherein the aqueous solution comprises at least one amine group, wherein the aqueous solution comprises at least one amine group, and wherein the aqueous solution comprises at least one amine group. Preferably, the molar ratio of hydrogen iodide to trifluoroacetyl halide may be about 0.5: 1 to about 2.0: 1. More preferably, the molar ratio of hydrogen iodide to trifluoroacetyl halide may be about 0.6: 1 to about 1.2: 1. Most preferably, the molar ratio of hydrogen iodide to trifluoroacetyl halide may be about 0.7: 1 to about 1.0: 1.

[0053] The trifluoroacetyl halide and hydrogen iodide forming the reaction stream can be preheated separately or together before entering the reactor. The reaction stream can be preheated to a temperature as low as about 20°C, about 30°C, about 40°C, about 50°C, about 60°C or about 70°C, or preheated to a temperature as high as about 80°C, about 90°C, about 100°C, about 110°C or about 120°C, or preheated to a temperature in any range defined between any two of the aforementioned values, such as, for example, about 30°C to about 120°C, about 40°C to about 110°C, about 50°C to about 100°C, about 60°C to about 90°C or about 70°C to about 80°C. Preferably, the reaction stream can be preheated to a temperature of about 40°C to about 120°C. More preferably, the reaction stream can be preheated to a temperature of about 60°C to about 110°C. Most preferably, the reaction stream can be preheated to a temperature of about 80°C to about 100°C.

[0054] The hydrogen iodide and trifluoroacetyl halide in the reactant stream react in the first reactor to produce an intermediate product stream comprising trifluoroacetyl iodide (CFCOI) and at least one hydrogen halide (HX) by-product according to the following equation 1:

[0055] Equation 1: HI + CF3COX → CF3COI + HX.

[0056] The at least one hydrogen halide is selected from the group consisting of hydrogen fluoride (HF), hydrogen chloride (HCl) and hydrogen bromide (HBr).

[0057] The first reactor may be a heated tube reactor comprising tubes made of a metal such as stainless steel, nickel and / or a nickel alloy such as a nickel-chromium alloy, a nickel-molybdenum alloy, a nickel-chromium-molybdenum alloy, or a nickel-copper alloy. The tubes within the first reactor may be heated. The first reactor may be any type of packed bed reactor.

[0058] The hydrogen iodide and trifluoroacetyl halide in the reactant stream react in the presence of a first catalyst contained in the first reactor. The first catalyst may comprise activated carbon, mesophase carbon, stainless steel, nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, aluminum oxide, platinum, palladium or carbide (such as metal carbide (such as iron carbide, molybdenum carbide and nickel carbide) and non-metallic carbide (such as silicon carbide)) or a combination thereof. The first catalyst may be in the form of a mesh, pellet or sphere contained in the first reactor. The first catalyst may have an average diameter in the range of about 1 mm to about 25 mm.

[0059] If the first catalyst comprises platinum and / or palladium, the first catalyst may be in the form of carrier-supported platinum and / or palladium. The carrier for the first catalyst may include aluminum oxide or carbon. The amount of carrier-supported platinum and / or palladium (as a percentage of the total weight of platinum and / or palladium and the carrier) may be as low as about 0.01 weight percent (wt%), about 0.1 wt%, about 0.3 wt%, about 0.5 wt%, about 0.7 wt%, about 1 wt%, about 2 wt% or about 3 wt%, or up to about 4 wt%, about 5 wt%, about 6 wt%, about 8 wt% or about 10 wt%, or in any range defined between any two of the aforementioned values, such as, for example, about 0.01 wt% to about 10 wt%, about 0.1 wt% to about 10 wt%, about 0.5 wt% to about 8 wt%, about 1 wt% to about 6 wt%, about 2 wt% to about 5 wt%, about 3 wt% to about 4 wt%, about 2 wt% to about 3 wt% or about 0.5 wt% to about 5 wt%. Preferably, the amount of platinum and / or palladium on the carrier may be about 0.1 wt % to about 1 wt %. More preferably, the amount of platinum and / or palladium on the carrier may be about 0.3 wt % to about 0.7 wt %. Most preferably, the amount of platinum and / or palladium on the carrier may be about 0.5 wt %.

[0060] Preferably, the first catalyst comprises activated carbon, mesophase carbon, stainless steel, platinum on a carrier, palladium on a carrier, or carbides (such as metal carbides and non-metallic carbides (such as silicon carbide)) or a combination thereof. More preferably, the first catalyst comprises platinum on a carrier, palladium on a carrier, activated carbon, silicon carbide, or a combination thereof. Most preferably, the first catalyst comprises activated carbon or silicon carbide.

[0061] Alternatively, the first catalyst may consist of a surface of the first reactor itself that is in contact with the reactant stream. The surface may provide a catalytic effect without the need for an additional catalyst.

[0062] The reactant stream can be contacted with the first catalyst for a contact time as short as about 0.1 second, 0.5 second, about 1 second, about 2 seconds, about 3 seconds, about 5 seconds, about 8 seconds, about 10 seconds, about 12 seconds, or about 15 seconds, about 18 seconds, or as long as about 20 seconds, about 25 seconds, about 30 seconds, about 35 seconds, about 40 seconds, about 50 seconds, about 60 seconds, about 80 seconds, or about 300 seconds, or any contact time within any range defined between any two of the foregoing values, such as, for example, about 0.1 second to about 300 seconds, about 0.5 second 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 12 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 about 10 seconds to about 30 seconds. Preferably, the reactant stream may be contacted with the first catalyst for a contact time of about 5 seconds to about 60 seconds. More preferably, the reactant stream may be contacted with the first catalyst for a contact time of about 10 seconds to about 40 seconds. Most preferably, the reactant stream may be contacted with the first catalyst for a contact time of about 15 seconds to about 35 seconds.

[0063] The reaction can be maintained at a first reaction operating pressure as low as about atmospheric pressure, about 5 psig (34 kPaG), about 10 psig (69 kPaG), about 15 psig (103 kPaG), about 20 psig (138 kPaG), about 25 psig (172 kPaG), about 30 psig (207 kPaG), about 35 psig (241 kPaG), or about 40 psig (276 kPaG), or as high as about 50 psig. g (345 kPaG), about 60 psig (414 kPaG), about 70 psig (483 kPaG), about 80 psig (552 kPaG), about 100 psig (689 kPaG), about 150 psig (1,034 kPaG), about 200 psig (1,379 kPaG), about 250 psig (1,724 kPaG) or about 300 psig (2,068 kPaG), or any two of the foregoing values psig (1,034 kPaG), about 20 psig (138 kPaG) to about 10 psig (69 kPaG) to about 200 psig (1,379 kPaG), about 15 psig (103 kPaG) to about 150 psig (1,034 kPaG), about 20 psig (138 kPaG) to about 10 The first reaction operating pressure is preferably about 5 psig (34 kPaG) to about 200 psig (1,379 kPaG). More preferably, the first reaction operating pressure is about 10 psig (69 kPaG) to about 150 psig (1,034 kPaG). Most preferably, the first reaction operating pressure is about 20 psig (138 kPaG) to about 100 psig (689 kPaG).

[0064] In addition to trifluoroacetyl iodide and hydrogen halide, the intermediate product stream also contains unreacted trifluoroacetyl halide and hydrogen iodide. The intermediate product stream may also contain small amounts of other organic compounds, such as, for example, trifluoroiodomethane (CF3I).

[0065] The composition of the organic compounds in the intermediate product stream can be measured by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS) analysis. The peak areas of each organic compound provided by the GC analysis can be combined to provide the GC area percentage (GC area %) of the total organic compound of each organic compound as a measure of the relative concentration of the organic compound in the intermediate product stream. The GC area % can be interpreted as equivalent to weight %.

[0066] The concentration of unreacted trifluoroacetyl halide in the intermediate product stream may be as low as about 1%, about 3%, about 5%, about 10%, about 15%, about 20%, about 25%, about 30%, about 35%, about 40%, or about 45%, or may be as high as about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, or about 90%, or in any range defined between any two of the foregoing values, such as, for example, about 1% to about 90%, about 5% to about 85%, about 10% to about 80%, about 15% to about 75%, about 20% to about 70%, about 25% to about 65%, about 30% to about 60%, about 35% to about 55%, about 40% to about 50%, about 1% to about 3%, about 5% to about 40%, or about 5% to about 60%. Preferably, the concentration of unreacted trifluoroacetyl halide in the intermediate product stream may be from about 1% to about 50%. More preferably, the concentration of unreacted trifluoroacetyl halide in the intermediate product stream may be from about 1% to about 40%. Most preferably, the concentration of unreacted trifluoroacetyl halide in the intermediate product stream may be from about 1% to about 30%.

[0067] The concentration of organic compounds excluding trifluoroacetyl halide, trifluoroacetyl iodide and trifluoroiodomethane in the intermediate product stream can be less than about 15%, about 14%, about 13%, about 12%, about 11%, about 10%, about 9%, about 8%, about 7%, about 6%, about 5%, about 4%, about 3%, about 2%, about 1%, about 0.5% or about 0.1% based on the GC area % of the total organic compounds. Preferably, the concentration of all other organic compounds in the intermediate product stream can be less than about 8%. More preferably, the concentration of all other organic compounds in the intermediate product stream can be less than about 4%. Most preferably, the concentration of all other organic compounds in the intermediate product stream can be less than about 2%.

[0068] The reaction stream can be heated to a first reaction temperature as low as about 25°C, about 30°C, about 40°C, about 50°C, about 60°C, about 70°C, about 80°C, about 90°C, about 100°C, or about 120°C, or as high as about 150°C, about 180°C, about 200°C, about 220°C, about 230°C, about 250°C, about 300°C, about 360°C, or about 400°C, or to a first reaction temperature within any range defined between any two of the foregoing values, such as, for example, about 25°C to about 400°C, about 30°C to about 360°C, about 40°C to about 300°C, for example, about 50°C to about 280°C, about 60°C to about 250°C, about 70°C to about 230°C, about 80°C to about 220°C, about 90°C to about 200°C, about 100°C to about 180°C, or about 110°C to about 150°C.

[0069] Generally, the conversion rate of trifluoroacetyl halide can be controlled by selecting the catalyst, the first reaction temperature, the molar ratio of hydrogen iodide to trifluoroacetyl halide, and the contact time.

[0070] Although the reaction can be carried out at a first reaction temperature of about 25° C. to about 400° C., it has been found that at lower reaction temperatures (such as a first reaction temperature equal to or less than about 120° C.), the reaction can produce low concentrations of trifluoroiodomethane in the intermediate product stream. Although trifluoroiodomethane may be a desired end product, the presence of trifluoroiodomethane in the intermediate product stream can reduce overall process efficiency because trifluoroiodomethane can form an azeotrope with a trifluoroacetyl halide (such as, for example, trifluoroacetyl chloride). The azeotrope can make it difficult to separate trifluoroiodomethane from trifluoroacetyl chloride, resulting in the loss of trifluoroiodomethane.

[0071] It has been found that at a first reaction temperature of about 120°C or less, the concentration of trifluoroiodomethane in the intermediate product stream can be less than 0.002% or about 20 ppm of the total organic compounds. GC area % of trifluoroiodomethane, the reaction stream can be heated to a first reaction temperature as low as about 25°C, about 30°C, about 35°C, about 40°C, about 45°C, about 50°C, about 55°C, about 60°C, about 65°C, or about 70°C, or as high as about 75°C, about 80°C, about 85°C, about 90°C, about 95°C, about 100°C, about 105°C, about 110°C, about 115°C, or about 120°C, or to a first reaction temperature within any range defined between any two of the foregoing values, such as, for example, about 25°C to about 120°C, about 30°C to about 115°C, about 35°C to about 110°C, about 40°C to about 105°C, about 45°C to about 100°C, about 50°C to about 95°C, about 55°C to about 90°C, about 60°C to about 85°C, about 65°C to about 80°C, or about 70°C to about 75°C. Preferably, the reaction stream may be heated to a first reaction temperature of about 40° C. to about 120° C. More preferably, the reaction stream may be heated to a first reaction temperature of about 70° C. to about 100° C. Most preferably, the reaction stream may be heated to a first reaction temperature of about 80° C. to about 100° C.

[0072] The concentration of trifluoroacetyl iodide in the intermediate product stream (based on GC area % of total organic compounds, where the reaction stream has a reaction temperature equal to or less than about 120° C.) can be as low as about 10%, about 20%, about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, or about 70%, or can be as high as about 75%, about 80%, about 85%, about 90%, about 95%, about 97%, about 98%, or about 99%. , or in any range defined between any two of the foregoing values, such as, for example, about 10% to about 99%, about 10% to about 99%, about 30% to about 99%, about 35% to about 98%, about 40% to about 97%, about 45% to about 95%, about 50% to about 90%, about 55% to about 85%, about 60% to about 80%, about 65% to about 75%, about 50% to about 60%, about 90% to about 99% or about 95% to about 99%. Preferably, the concentration of trifluoroacetyl iodide in the intermediate product stream may be about 50% to about 99%. More preferably, the concentration of trifluoroacetyl iodide in the intermediate product stream may be about 60% to about 99%. Most preferably, the concentration of trifluoroacetyl iodide in the intermediate product stream may be about 70% to about 99%.

[0073] The concentration of trifluoroiodomethane in the intermediate product stream (in terms of GC area % of total organic compounds, where the reaction stream has a reaction temperature equal to or less than about 120° C.) may be less than about 0.010%, less than about 0.005%, less than about 0.002%, less than about 0.001%, less than about 0.0005%, less than about 0.0002%, or less than about 0.0001%, or less than any value defined between any two of the foregoing values. Preferably, the concentration of trifluoroiodomethane in the intermediate product stream may be less than about 0.002%. More preferably, the concentration of trifluoroiodomethane in the intermediate product stream may be less than about 0.001%. Most preferably, the concentration of trifluoroiodomethane in the intermediate product stream may be less than about 0.0005%.

[0074] In other words, the organic compounds in the intermediate product stream (where the reaction stream has a first reaction temperature equal to or lower than about 120° C.) may contain, based on the GC area % of the total 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. It is also provided that the organic compounds in the intermediate product stream may contain about 50% to about 99% trifluoroacetyl iodide, about 1% to about 50% unreacted trifluoroacetyl halide, less than about 0.002% trifluoroiodomethane, and less than about 8% organic compounds other than trifluoroacetyl iodide, trifluoroacetyl halide, and trifluoroiodomethane. It is also provided that the organic compounds in the intermediate product stream may contain about 60% to about 99% trifluoroacetyl iodide, about 1% to about 40% unreacted trifluoroacetyl halide, less than about 0.001% trifluoroiodomethane, and less than about 4% of organic compounds other than trifluoroacetyl iodide, trifluoroacetyl halide, and trifluoroiodomethane. It is also provided that the organic compounds in the intermediate product stream may contain about 70% to about 99% trifluoroacetyl iodide, about 1% to about 30% unreacted trifluoroacetyl halide, less than about 0.0005% trifluoroiodomethane, and less than about 2% of organic compounds other than trifluoroacetyl iodide, trifluoroacetyl halide, and trifluoroiodomethane.

[0075] In other words, the organic compounds in the intermediate product stream (wherein the reaction stream has a first reaction temperature equal to or less than about 120° C.) can consist essentially of 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, based on GC area % of total organic compounds. It is also provided that the organic compounds in the intermediate product stream can consist essentially of about 50% to about 99% trifluoroacetyl iodide, about 1% to about 50% unreacted trifluoroacetyl halide, less than about 0.002% trifluoroiodomethane, and less than about 8% organic compounds other than trifluoroacetyl iodide, trifluoroacetyl halide, and trifluoroiodomethane. It is also provided that the organic compounds in the intermediate product stream may consist essentially of about 60% to about 99% trifluoroacetyl iodide, about 1% to about 40% unreacted trifluoroacetyl halide, less than about 0.001% trifluoroiodomethane, and less than about 4% of organic compounds other than trifluoroacetyl iodide, trifluoroacetyl halide, and trifluoroiodomethane. It is also provided that the organic compounds in the intermediate product stream may consist essentially of about 70% to about 99% trifluoroacetyl iodide, about 1% to about 30% unreacted trifluoroacetyl halide, less than about 0.0005% trifluoroiodomethane, and less than about 2% of organic compounds other than trifluoroacetyl iodide, trifluoroacetyl halide, and trifluoroiodomethane.

[0076] In other words, the organic compounds in the intermediate product stream (wherein the reaction stream has a first reaction temperature equal to or less than about 120° C.) can be composed of 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, based on the GC area % of the total organic compounds. It is also provided that the organic compounds in the intermediate product stream can be composed of about 50% to about 99% trifluoroacetyl iodide, about 1% to about 50% unreacted trifluoroacetyl halide, less than about 0.002% trifluoroiodomethane, and less than about 8% organic compounds other than trifluoroacetyl iodide, trifluoroacetyl halide, and trifluoroiodomethane. It is also provided that the organic compound in the intermediate product stream may consist of about 60% to about 99% trifluoroacetyl iodide, about 1% to about 40% unreacted trifluoroacetyl halide, less than about 0.001% trifluoroiodomethane, and less than about 4% of organic compounds other than trifluoroacetyl iodide, trifluoroacetyl halide, and trifluoroiodomethane. It is also provided that the organic compound in the intermediate product stream may consist of about 70% to about 99% trifluoroacetyl iodide, about 1% to about 30% unreacted trifluoroacetyl halide, less than about 0.0005% trifluoroiodomethane, and less than about 2% of organic compounds other than trifluoroacetyl iodide, trifluoroacetyl halide, and trifluoroiodomethane.

[0077] The intermediate product stream may directly enter the first distillation column. Alternatively, the intermediate product stream may pass through a heat exchanger to cool the intermediate product stream before providing the intermediate product stream to the first distillation column.

[0078] The first distillation tower is configured to separate some of the above-mentioned by-products, reactants and organic compounds from trifluoroacetyl iodide to produce a purified intermediate product stream. The first distillation tower can be configured to separate unreacted hydrogen iodide and return it to the reactant stream, and to separate unreacted trifluoroacetyl halide and return it to the reactant stream. The first distillation tower can also be configured to separate the hydrogen halide into a hydrogen halide stream for sale, reuse or treatment elsewhere. The first distillation tower may include a series of distillation towers, such as a hydrogen halide tower for removing hydrogen halide and light organics; a light tower for removing unreacted trifluoroacetyl halide and unreacted hydrogen iodide, which are then sent to a circulation tower to separate unreacted trifluoroacetyl halide from unreacted hydrogen iodide; and a heavy tower for purging heavy organics and producing a purified intermediate product stream.

[0079] The concentration of trifluoroacetyl iodide in the purified intermediate product stream may be greater than about 98 weight percent (wt%). Preferably, the concentration of trifluoroacetyl iodide in the purified intermediate product stream may be greater than about 99 weight %. More preferably, the concentration of trifluoroacetyl iodide in the purified intermediate product stream may be greater than about 99.5 weight %. Most preferably, the concentration of trifluoroacetyl iodide in the purified intermediate product stream may be greater than about 99.7 weight %.

[0080] The concentration of some impurities in the purified intermediate product stream can detract from further use of trifluoroacetyl iodide. Thus, if the trifluoroacetyl halide in the reactant stream includes trifluoroacetyl chloride, the purified intermediate product stream contains a total of about 1 ppm (parts per million by weight) to about 20,000 ppm (about 2 weight %) of compounds selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane. Preferably, the purified intermediate product stream contains a total of about 1 ppm to about 10,000 ppm (about 1 weight %) of compounds selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane. More preferably, the purified intermediate product stream comprises a total of about 1 ppm to about 5,000 ppm of a compound selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane. Most preferably, the purified intermediate product stream comprises a total of about 1 ppm to about 3,000 ppm of a compound selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane.

[0081] In other words, the purified intermediate product stream may contain at least 98% by weight of trifluoroacetyl iodide and a total of about 1 ppm to about 20,000 ppm (about 2% by weight) of compounds selected from the following: chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane. It is also provided that the purified intermediate product stream may contain at least 99% by weight of trifluoroacetyl iodide and a total of 1 ppm to 10,000 ppm (1% by weight) of compounds selected from the following: chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane. It is also provided that the purified intermediate product stream may contain at least 99.5% by weight of trifluoroacetyl iodide and a total of 1 ppm to 5,000 ppm of compounds selected from the following: chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane. It is further provided that the purified intermediate product stream may comprise at least 99.7 wt % trifluoroacetyl iodide and a total of 1 ppm to 3,000 ppm of a compound selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid and chlorotrifluoromethane.

[0082] In other words, the purified intermediate product stream can consist essentially of at least 98% by weight of trifluoroacetyl iodide and a total of about 1 ppm to about 20,000 ppm (about 2% by weight) of a compound selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane. It is also provided that the purified intermediate product stream can consist essentially of at least 99% by weight of trifluoroacetyl iodide and a total of 1 ppm to 10,000 ppm (1% by weight) of a compound selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane. It is also provided that the purified intermediate product stream may consist essentially of at least 99.5% by weight of trifluoroacetyl iodide and a total of 1 ppm to 5,000 ppm of a compound selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane. It is also provided that the purified intermediate product stream may consist essentially of at least 99.7% by weight of trifluoroacetyl iodide and a total of 1 ppm to 3,000 ppm of a compound selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane.

[0083] In other words, the purified intermediate product stream can be composed of at least 98% by weight of trifluoroacetyl iodide and a total of about 1 ppm to about 20,000 ppm (about 2% by weight) of a compound selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane. It is also provided that the purified intermediate product stream can be composed of at least 99% by weight of trifluoroacetyl iodide and a total of 1 ppm to 10,000 ppm (1% by weight) of a compound selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane. It is also provided that the purified intermediate product stream can be composed of at least 99.5% by weight of trifluoroacetyl iodide and a total of 1 ppm to 5,000 ppm of a compound selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane. It is also provided that the purified intermediate product stream may consist of at least 99.7 wt % trifluoroacetyl iodide and a total of 1 ppm to 3,000 ppm of a compound selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid and chlorotrifluoromethane.

[0084] The purified intermediate product stream can be stored, or it can be provided to the second reactor to be converted into trifluoroiodomethane. The purified intermediate product stream comprising trifluoroacetyl iodide can be directly provided to the second reactor. Alternatively or in addition, before the purified intermediate product stream is provided to the second reactor, the purified intermediate product stream can be passed through a preheater to heat the purified intermediate product stream.

[0085] The trifluoroacetyl iodide in the purified intermediate product stream is reacted in the second reactor to produce a final product stream comprising trifluoroiodomethane and reaction byproduct carbon monoxide (CO) according to the following Equation 2:

[0086] Equation 2: CF3COI→CF3I+CO.

[0087] The second reactor may be a heated tube reactor comprising tubes made of a metal such as stainless steel, nickel and / or a nickel alloy such as a nickel-chromium alloy, a nickel-molybdenum alloy, a nickel-chromium-molybdenum alloy, or a nickel-copper alloy. The tubes within the second reactor may be heated. The second reactor may be any type of packed bed reactor.

[0088] The purified intermediate product stream can be heated to a second reaction temperature as low as about 200°C, about 250°C, about 300°C, about 310°C, about 320°C, about 325°C, about 330°C, about 340°C, about 350°C, or about 360°C, or to a second reaction temperature as high as about 370°C, about 380°C, about 390°C, about 400°C, about 425°C, about 450°C, about 475°C, about 500°C, about 525°C, or about 540°C. ℃, about 550℃, about 575℃ or about 600℃, or in any range defined between any two of the foregoing values, such as, for example, about 200℃ to about 600℃, about 250℃ to about 600℃, about 300℃ to about 600℃, about 320℃ to about 450℃, about 325℃ to about 400℃, about 330℃ to about 390℃, about 340℃ to about 380℃, about 350℃ to about 370℃ or about 340℃ to about 360℃. Preferably, the second catalyst can be heated to a second reaction temperature of about 250℃ to about 500℃. More preferably, the second catalyst can be heated to a second reaction temperature of about 300℃ to about 400℃. Most preferably, the second catalyst can be heated to a second reaction temperature of about 300℃ to about 350℃.

[0089] The trifluoroacetyl iodide in the purified intermediate product stream can be reacted in the presence of a second catalyst contained in the second reactor. The second catalyst can include stainless steel, nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, aluminum oxide, silicon carbide, platinum, palladium, rhenium, activated carbon (such as Norit-PK35, Calgon or Shirasagi carbon) or a combination thereof. The second catalyst can be in the form of a mesh, pellet or sphere contained in the second reactor. The second catalyst can have an average diameter in the range of about 1 mm to about 25 mm.

[0090] If the second catalyst comprises platinum, palladium and / or rhenium, the second catalyst may be in the form of platinum, palladium and / or rhenium on a carrier. The carrier for the second catalyst may include alumina or carbon. The amount of platinum, palladium and / or rhenium on the carrier (as a percentage of the total weight of platinum, palladium and / or rhenium and the carrier) can be as low as about 0.01 weight percent (wt%), about 0.1 wt%, about 0.3 wt%, about 0.5 wt%, about 0.7 wt%, about 1 wt%, about 2 wt%, or about 3 wt%, or up to about 4 wt%, about 5 wt%, about 6 wt%, about 8 wt%, or about 10 wt%, or in any range defined between any two of the foregoing values, such as, for example, about 0.01 wt% to about 10 wt%, 0.1 wt% to about 10 wt%, about 0.5 wt% to about 8 wt%, about 1 wt% to about 6 wt%, about 2 wt% to about 5 wt%, about 3 wt% to about 4 wt%, about 2 wt% to about 3 wt%, or about 0.5 wt% to about 5 wt%. Preferably, the amount of platinum, palladium and / or rhenium on the carrier can be about 0.1 wt% to about 1 wt%. More preferably, the amount of platinum, palladium and / or rhenium on the carrier may be about 0.3 wt % to about 0.7 wt %.Most preferably, the amount of platinum, palladium and / or rhenium on the carrier may be about 0.5 wt %.

[0091] Preferably, the second catalyst comprises activated carbon, about 0.1 wt % to about 1 wt % of platinum on a carrier, about 0.1 wt % to about 1 wt % of palladium on a carrier, about 0.1 wt % to about 1 wt % of rhenium on a carrier, or a combination thereof. More preferably, the second catalyst comprises activated carbon or about 0.3 wt % to about 0.7 wt % of palladium on a carrier. Most preferably, the second catalyst comprises activated carbon.

[0092] The second catalyst may be activated carbon, such as, for example, Norit-PK35, Calgon, or Shirasagi carbon pellets or spheres. The activated carbon may have a surface area as small as about 500 square meters per gram (m 2 / g), about 800m 2 / g, about 850m 2 / g, about 900m 2 / g, about 950m 2 / g or about 1,000m 2 / g, or up to about 1,100m 2 / g, about 1,200m 2 / g, about 1,300m 2 / g, about 1,400m 2 / g, about 1,600m 2 / g, about 1,800m 2 / g, about 2,000m 2 / g or about 3,000m 2 / g, or having a surface area within any range defined between any two of the foregoing values, such as, for example, about 500 m 2 / g to about 3,000m 2 / g, about 800m 2 / g to about 2,000m 2 / g, about 850m 2 / g to about 1,800m 2 / g, about 900m 2 / g to about 1,600m 2 / g, about 950m 2 / g to about 1,400m 2 / g, about 1,000m 2 / g to about 1,200m 2 / g or about 850m 2 / g to about 1,300m 2 / g.

[0093] The activated carbon can have an average pore size as small as about 0.2 nanometers (nm), about 0.5 nm, about 1 nm, about 1.5 nm, about 2 nm, or about 2.5 nm, or as large as about 3 nm, about 5 nm, about 10 nm, about 15 nm, about 20 nm, or about 25 nm, or an average pore size within any range defined between any two of the foregoing values, such as, for example, about 0.2 nm to about 25 nm, about 0.2 nm to about 20 nm, about 1.0 nm to about 15 nm, about 1.5 nm to about 10 nm, about 2 nm to about 5 nm, or about 2.5 nm to about 3 nm.

[0094] Alternatively, the second catalyst may consist of the surface of the second reactor itself (ie, an otherwise empty reactor) that is in contact with the purified intermediate product stream. The surface may provide a catalytic effect without the need for an additional solid catalyst.

[0095] The purified intermediate product stream can be contacted with the second catalyst for a contact time as short as about 0.1 seconds, 1 second, about 2 seconds, about 3 seconds, about 5 seconds, about 8 seconds, about 10 seconds, about 12 seconds, or about 15 seconds, or as long as about 18 seconds, 20 seconds, about 25 seconds, about 30 seconds, about 35 seconds, about 40 seconds, about 50 seconds, about 60 seconds, or about 300 seconds, or any contact time as follows: in any range defined between any two of the aforementioned values, such as, for example, about 0.1 seconds to about 300 seconds, about 1 second to about 60 seconds, 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, 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 to about 30 seconds. Preferably, the purified intermediate product stream can be contacted with the second catalyst for a contact time of about 1 second to about 60 seconds. More preferably, the purified intermediate product stream may be contacted with the second catalyst for a contact time of about 2 seconds to about 50 seconds. Most preferably, the purified intermediate product stream may be contacted with the second catalyst for a contact time of about 3 seconds to about 30 seconds.

[0096] The reaction can be maintained at a second reaction operating pressure as low as about atmospheric pressure, about 5 psig (34 kPaG), about 10 psig (69 kPaG), about 15 psig (103 kPaG), about 20 psig (138 kPaG), about 25 psig (172 kPaG), about 30 psig (207 kPaG), about 35 psig (241 kPaG), about 40 psig (276 kPaG), or about 50 psig (345 kPaG), or as high as about 60 psig (414 kPaG), about 70 psig (483 kPaG), about 80 psig (552 kPaG), about 100 psig (689 kPaG), about 120 psig (827 kPaG), about 150 psig (1,034 kPaG), about 200 psig (1,379 kPaG), about 250 psig (1,724 kPaG) or about 300 psig (2,068 KPaG), or in any range defined between any two of the foregoing values, such as, for example, about atmospheric pressure to about 300 psig (2,068 KPaG), about 5 psig (34 kPaG) to about 300 psig (2,068 KPaG) , about 5 psig (34 kPaG) to about 250 psig (1,724 kPaG), about 10 psig (69 kPaG) to about 200 psig (1,379 kPaG), about 15 psig (103 kPaG) to about 150 psig (1,034 kPaG), about 20 psig (138 kPaG) to about 120 psig (827 kPaG), about 25 psig (172 kPaG) to about 100 psig (689 kPaG), about 30 psig (207 kPaG) to about 80 psig (552 kPaG), about 35 psig (241 kPaG) to about 70 psig (483 kPaG), about 40 psig (276 kPaG) to about 70 psig (483 kPaG), about 50 psig (345 kPaG) to about 60 psig (414 kPaG), 50 psig (345 kPaG) to about 250 psig (1,724 kPaG), about 100 psig (689 kPaG) to about 200 psig (1,379 kPaG), or about 150 psig (1,034 kPaG) to about 200 psig (1,379 kPaG).

[0097] It has been discovered that even in the absence of a second catalyst, the conversion of trifluoroacetyl iodide can be significantly improved by operating at pressures greater than atmospheric pressure.

[0098] The final product stream may directly enter the second distillation column. Alternatively, the final product stream may pass through a heat exchanger to cool the final product stream before providing the final product stream to the second distillation column.

[0099] The final product stream comprises a composition containing trifluoroiodomethane and carbon monoxide byproducts and unreacted trifluoroacetyl iodide, as shown in Equation 2. The final product stream composition may also comprise residual impurities from the purified intermediate product stream, such as trifluoroacetyl chloride (CF3COCl) and chlorotrifluoroethane (C2H2ClF3) and byproducts, such as trifluoromethane (CHF3), hexafluoroethane (C2F6), trifluoroacetyl fluoride (CF3COF), hexafluoroacetone (CF3COCF3), trifluoroacetaldehyde (CF3COH), trifluorochloromethane (CF3Cl), pentafluoroiodoethane (C2F5I), difluoroiodomethane (CHF2I), pentafluoroacetone (CF3COCHF2), trifluoroacetic anhydride (CF3COOCOCF3), heptafluoroiodopropane (C3F7I), iodomethane (CH3I), difluorochloroiodomethane (CClF2I) and / or trifluoroacetic acid (CF3COOH)).

[0100] The second distillation column is configured to separate unreacted trifluoroacetyl iodide and byproducts, such as carbon monoxide, trifluoromethane and hexafluoroethane, from the final product stream composition. The second distillation column can be configured to separate unreacted trifluoroacetyl iodide and return it to the purified intermediate product stream. The second distillation column can also be configured to separate carbon monoxide into a carbon monoxide stream for sale, reuse elsewhere or disposal.

[0101] The final product stream composition also comprises chlorotrifluoroethane except trifluoroiodomethane, and may also comprise residual carbon monoxide and hydrogen halide.The third distillation column is configured to separate some chlorotrifluoroethane from trifluoroiodomethane.The third distillation column may also be configured to separate residual carbon monoxide and hydrogen chloride from trifluoroiodomethane to produce a purified final product composition.The second distillation column and the third distillation column may comprise a series of distillation columns configured to remove by-products such as trifluorochloromethane, pentafluoro iodoethane, difluoro iodomethane, pentafluoroacetone, trifluoroacetic anhydride, heptafluoro iodopropane, methyl iodide, difluoro chloroiodomethane and / or trifluoroacetic acid, and some in trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde and trifluoroacetyl chloride in addition.The purified final product composition may be directed to a storage tank.

[0102] The purified final product composition has a trifluoroiodomethane concentration greater than 99% by weight. Preferably, the concentration of trifluoroiodomethane in the purified final product composition may be greater than 99.5% by weight. More preferably, the concentration of trifluoroiodomethane in the purified final product composition may be greater than 99.7% by weight. Most preferably, the concentration of trifluoroiodomethane in the purified final product composition may be greater than 99.9% by weight.

[0103] The concentration of some impurities in the purified final product stream can detract from the performance of trifluoroiodomethane and its intended purpose as an environmentally safe, non-toxic gas. If the trifluoroacetyl halide in the reactant stream includes trifluoroacetyl chloride, the purified final product composition comprises 1 ppm (parts per million by weight) 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 of hydrogen chloride. Preferably, the purified final product stream comprises 1 ppm to 250 ppm of chlorotrifluoroethane, less than 250 ppm of hexafluoroethane, less than 250 ppm of trifluoromethane, less than 50 ppm of carbon monoxide, and less than 0.5 ppm of hydrogen chloride. More preferably, the purified final product stream comprises 1 ppm to 100 ppm of chlorotrifluoroethane, less than 10 ppm of hexafluoroethane, less than 100 ppm of trifluoromethane, less than 10 ppm of carbon monoxide, and less than 0.2 ppm of hydrogen chloride.

[0104] The purified final product composition may also contain a compound selected from the following in an amount of 1 ppm to 500 ppm in total: trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde and trifluoroacetyl chloride. Preferably, the purified final product composition also contains a compound selected from the following in an amount of 1 ppm to 250 ppm in total: trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde and trifluoroacetyl chloride. More preferably, the purified final product composition also contains a compound selected from the following in an amount of 1 ppm to 100 ppm in total: trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde and trifluoroacetyl chloride.

[0105] In other words, if the trifluoroacetyl halide in the reactant stream includes trifluoroacetyl chloride, the purified final product composition may contain 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, less than 1 ppm of hydrogen chloride, and a total of 1 ppm to 500 ppm of a compound selected from the group consisting of trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde, and trifluoroacetyl chloride. It is also provided that the purified final product composition may contain at least 99.5% by weight of trifluoroiodomethane, 1 ppm to 250 ppm of chlorotrifluoroethane, less than 250 ppm of hexafluoroethane, less than 250 ppm of trifluoromethane, less than 50 ppm of carbon monoxide, less than 0.5 ppm of hydrogen chloride, and a total of 1 ppm to 250 ppm of a compound selected from the group consisting of trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde, and trifluoroacetyl chloride. It is also provided that the purified final product composition may contain at least 99.7% by weight of trifluoroiodomethane, 1 ppm to 100 ppm of chlorotrifluoroethane, less than 100 ppm of hexafluoroethane, less than 100 ppm of trifluoromethane, less than 20 ppm of carbon monoxide, less than 0.2 ppm of hydrogen chloride, and a total of 1 ppm to 100 ppm of a compound selected from the group consisting of trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde, and trifluoroacetyl chloride. It is also provided that the purified final product composition may contain at least 99.9% by weight of trifluoroiodomethane, 1 ppm to 100 ppm of chlorotrifluoroethane, less than 100 ppm of hexafluoroethane, less than 100 ppm of trifluoromethane, less than 20 ppm of carbon monoxide, less than 0.2 ppm of hydrogen chloride, and a total of 1 ppm to 100 ppm of a compound selected from the group consisting of trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde, and trifluoroacetyl chloride.

[0106] In other words, if the trifluoroacetyl halide in the reactant stream includes trifluoroacetyl chloride, the purified final product composition can be essentially composed of 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, less than 1 ppm of hydrogen chloride, and the balance is selected from the following compounds: trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde and trifluoroacetyl chloride. It is also provided that the purified final product composition can be essentially composed of at least 99.5% by weight of trifluoroiodomethane, 1 ppm to 250 ppm of chlorotrifluoroethane, less than 250 ppm of hexafluoroethane, less than 250 ppm of trifluoromethane, less than 50 ppm of carbon monoxide, less than 0.5 ppm of hydrogen chloride, and the balance is selected from the following compounds: trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde and trifluoroacetyl chloride. It is also provided that the purified final product composition can be essentially composed of at least 99.7% by weight of trifluoroiodomethane, 1 ppm to 100 ppm of chlorotrifluoroethane, less than 100 ppm of hexafluoroethane, less than 100 ppm of trifluoromethane, less than 20 ppm of carbon monoxide, less than 0.2 ppm of hydrogen chloride, and the balance is selected from the following compounds: trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde and trifluoroacetyl chloride. It is also provided that the purified final product composition can be essentially composed of at least 99.9% by weight of trifluoroiodomethane, 1 ppm to 100 ppm of chlorotrifluoroethane, less than 100 ppm of hexafluoroethane, less than 100 ppm of trifluoromethane, less than 100 ppm of carbon monoxide, less than 0.2 ppm of hydrogen chloride, and the balance is selected from the following compounds: trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde and trifluoroacetyl chloride.

[0107] In other words, if the trifluoroacetyl halide in the reactant stream includes trifluoroacetyl chloride, the purified final product composition can be composed of 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, less than 1 ppm of hydrogen chloride, and the balance is selected from the following compounds: trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde and trifluoroacetyl chloride. It is also provided that the purified final product composition can be composed of at least 99.5% by weight of trifluoroiodomethane, 1 ppm to 250 ppm of chlorotrifluoroethane, less than 250 ppm of hexafluoroethane, less than 250 ppm of trifluoromethane, less than 50 ppm of carbon monoxide, less than 0.5 ppm of hydrogen chloride, and the balance is selected from the following compounds: trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde and trifluoroacetyl chloride. It is also provided that the purified final product composition can be composed of at least 99.7% by weight of trifluoroiodomethane, 1 ppm to 100 ppm of chlorotrifluoroethane, less than 100 ppm of hexafluoroethane, less than 100 ppm of trifluoromethane, less than 20 ppm of carbon monoxide, less than 0.2 ppm of hydrogen chloride, and the balance is selected from the following compounds: trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde and trifluoroacetyl chloride. It is also provided that the purified final product composition can be composed of at least 99.9% by weight of trifluoroiodomethane, 1 ppm to 100 ppm of chlorotrifluoroethane, less than 100 ppm of hexafluoroethane, less than 100 ppm of trifluoromethane, less than 100 ppm of carbon monoxide, less than 0.2 ppm of hydrogen chloride, and the balance is selected from the following compounds: trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde and trifluoroacetyl chloride.

[0108] It has been found that the purified final product stream of the above two-step gas phase process produces a high purity trifluoroiodomethane product due to the high purity of trifluoroacetyl iodide in the purified intermediate product stream. The two-step gas phase process produces surprisingly good process yields and is suitable for the production of trifluoroiodomethane on a commercial scale.

[0109] Alternatively or additionally, the reactant stream comprising trifluoroacetyl iodide may be provided to a second reactor for conversion to trifluoroiodomethane as described above.The reactant stream comprising trifluoroacetyl iodide may be produced by methods other than those described above.

[0110] Figure 1 FIG. 1 is a process flow diagram showing a gas phase method 10 for producing trifluoroacetyl iodide. Figure 1 As shown, process 10 includes a material stream of hydrogen iodide (HI) 12 and at least one trifluoroacetyl halide, namely trifluoroacetyl chloride (CF3COCl) 14. Although trifluoroacetyl chloride is used for illustration Figures 1 to 3The method of the present invention is to provide a trifluoroacetyl halide, but it should be understood that, alternatively or in addition, the trifluoroacetyl halide can be trifluoroacetyl bromide or trifluoroacetyl fluoride. The hydrogen iodide stream 12 and the trifluoroacetyl chloride stream 14 are combined in a mixer valve 16 to form a reaction stream 18. The reaction stream 18 can be provided directly to the reactor 20. Alternatively, before the reaction stream 18 is provided to the reactor 20, the reaction stream 18 can pass through a preheater 22 to heat the reaction stream 18.

[0111] Trifluoroacetyl chloride and hydrogen iodide in reactant stream 18 react in the presence of catalyst 24 contained in reactor 20 to produce product stream 26 comprising trifluoroacetyl iodide (CF3COI) and hydrogen chloride (HCl) byproduct according to Equation 1 above.

[0112] In addition to trifluoroacetyl iodide and hydrogen chloride, product stream 26 also contains unreacted trifluoroacetyl chloride and hydrogen iodide. Product stream 26 may even contain small amounts of other organic compounds, such as trifluoroiodomethane (CF3I).

[0113] Product stream 26 may be fed directly to distillation column 28. Alternatively, product stream 26 may be passed through heat exchanger 30, such as Figure 1 Heat exchanger 30 is configured to cool product stream 26 before it enters distillation column 28.

[0114] The distillation column 28 is configured to separate some of the above-mentioned by-products, reactants and organic compounds from the trifluoroacetyl iodide to produce a purified product stream 32. Figure 1 As shown, distillation column 28 is configured to separate unreacted hydrogen iodide in hydrogen iodide stream 36 and return it to hydrogen iodide stream 12 for use in reactant stream 18 , and to separate unreacted trifluoroacetyl chloride in trifluoroacetyl chloride stream 34 and return it to trifluoroacetyl chloride stream 14 for use in reactant stream 18 .

[0115] The distillation column 28 is also configured to separate the hydrogen chloride into a hydrogen chloride waste stream 38 for sale, reuse elsewhere, or disposal. The purified product stream 32 comprising trifluoroacetyl iodide is directed to a storage tank 40 .

[0116] It has been found that reacting hydrogen iodide and trifluoroacetyl chloride at the above temperature in the presence of catalyst 24 results in high selectivity in favor of trifluoroacetyl iodide and high conversion of hydrogen iodide and trifluoroacetyl chloride. The gas phase process described above with reference to Equation 1 produces surprisingly good process yields and is suitable for commercial-scale production of trifluoroacetyl iodide.

[0117] Figure 2 FIG. 1 is a process flow diagram showing a two-step gas phase process 110 for producing trifluoroiodomethane. Figure 2As shown, the process 110 includes material flows of hydrogen iodide (HI) 112 and at least one trifluoroacetyl chloride (CF3COCl) 114. The hydrogen iodide flow 112 and the trifluoroacetyl chloride flow 114 are combined in a mixer valve 116 to form a reactant stream 118. The reactant stream 118 may be provided directly to a first reactor 120. Alternatively, the reactant stream 118 may pass through a preheater 122 to heat the reactant stream 118 before providing the reactant stream 118 to the first reactor 120.

[0118] Trifluoroacetyl chloride and hydrogen iodide in reactant stream 118 react in the presence of first catalyst 124 contained in first reactor 120 to produce an intermediate product stream 126 comprising trifluoroacetyl iodide (CF3COI) and hydrogen chloride (HCl) byproducts according to Equation 1 above.

[0119] In addition to trifluoroacetyl iodide and hydrogen chloride, the intermediate product stream 126 also contains unreacted trifluoroacetyl chloride and hydrogen iodide. The intermediate product stream 126 may even contain small amounts of other organic compounds, such as, for example, trifluoroiodomethane (CF3I).

[0120] The intermediate product stream 126 may be directly fed into the first distillation column 128. Alternatively, the intermediate product stream 126 may be passed through a heat exchanger 130, such as Figure 2 The heat exchanger 130 is configured to cool the intermediate product stream 126 before it enters the first distillation column 128 .

[0121] The first distillation column 128 can be configured to separate some of the above-mentioned byproducts, reactants, and organic compounds from trifluoroacetyl iodide to produce a purified intermediate product stream 132. Figure 2 As shown, first distillation column 128 is configured to separate unreacted hydrogen iodide in hydrogen iodide stream 134 and return it to hydrogen iodide stream 112 for use in reactant stream 118 .

[0122] First distillation column 128 is configured to separate unreacted trifluoroacetyl chloride in trifluoroacetyl chloride stream 136 and return it to trifluoroacetyl chloride stream 114 for use in reactant stream 118. First distillation column 128 is also configured to separate hydrogen chloride into hydrogen chloride stream 138 for sale, reuse elsewhere, or disposal.

[0123] The purified intermediate product stream 132 may be provided directly to the second reactor 140, such as Figure 2 Alternatively, before providing the purified intermediate product stream 132 to the second reactor 140 , the purified intermediate product stream 132 may pass through a preheater (not shown) to heat the purified intermediate product stream 132 .

[0124] The trifluoroacetyl iodide in the purified intermediate product stream 132 reacts in the presence of a second catalyst 142 contained within the second reactor 140 to produce a product stream 144 comprising trifluoroiodomethane and a reaction byproduct, carbon monoxide (CO), according to Equation 2 above.

[0125] Product stream 144 may be directly fed into a second distillation column 146 such as Figure 2 Alternatively, the product stream 144 may pass through a heat exchanger (not shown) before providing the product stream 144 to the second distillation column 146. The heat exchanger is configured to cool the product stream 144 before it enters the second distillation column 146.

[0126] In addition to trifluoroiodomethane and carbon monoxide, product stream 144 also contains unreacted trifluoroacetyl iodide and other byproducts, such as trifluoromethane (CHF3), hexafluoroethane (C2F6), and chlorotrifluoroethane (C2H2ClF3). Second distillation column 146 is configured to separate unreacted trifluoroacetyl iodide and byproducts (such as carbon monoxide, trifluoromethane, and hexafluoroethane) from trifluoroiodomethane to produce a purified product stream 148 containing trifluoroiodomethane. Figure 2 As shown, the second distillation column 146 can be configured to separate unreacted trifluoroacetyl iodide in an unreacted trifluoroacetyl iodide stream 150 and return it to the purified intermediate product stream 132. The second distillation column 146 can also be configured to separate carbon monoxide into a carbon monoxide stream 152 for sale, reuse elsewhere, or disposal.

[0127] like Figure 2 As shown, the purified product stream 148 comprising trifluoroiodomethane is directed to a third distillation column 154 for additional purification. In addition to trifluoroiodomethane, the purified product stream 148 also comprises chlorotrifluoroethane, and may also comprise residual carbon monoxide and hydrogen chloride. The third distillation column 154 is configured to separate chlorotrifluoroethane from trifluoroiodomethane to produce a purified final product stream 156 comprising trifluoroiodomethane. Figure 2 As shown, the third distillation column 154 can be configured to separate the chlorotrifluoroethane into a chlorotrifluoroethane stream 158 for sale, reuse elsewhere, or disposal. The third distillation column 154 can also be configured to separate carbon monoxide and hydrogen chloride into a waste stream 160 for disposal. The purified final product stream 156 containing trifluoroiodomethane can be directed to a storage tank 162.

[0128] Figure 3 2 is a process flow diagram showing a method 210 for producing trifluoroiodomethane from trifluoroacetyl iodide. The method 210 may be similar to that described above and with reference to Figure 2The second step in the two-step method of is the same as that of the first step, except that the purified intermediate product stream 132 is replaced by the reaction stream 232. The reaction stream 232 contains trifluoroacetyl iodide. The trifluoroacetyl iodide can be produced by methods other than those described herein. The reaction stream 232 can also contain trifluoroacetyl iodide produced by the methods described herein.

[0129] Although the present invention has been described with respect to exemplary designs, the present invention may be further modified within the spirit and scope of the present disclosure. Further, this application is intended to cover such departures from the present disclosure as come within known or customary practice in the art to which the invention pertains.

[0130] As used herein, the phrase "in any range defined between any two preceding values" literally means that any range can be selected from any two values ​​listed before such phrase, regardless of whether these values ​​are in the lower part of the list or in the upper part of the list. For example, a pair of values ​​can be selected from two lower values, two higher values, or a lower value and an upper value.

[0131] Example

[0132] Example 1: Preparation of trifluoroacetyl iodide at a higher reaction temperature according to equation 1

[0133] In this embodiment, it is demonstrated that trifluoroacetyl iodide is made by hydrogen iodide and trifluoroacetyl chloride at a higher temperature according to equation 1 as described above. In twenty-three series of experiments, equimolar amounts of trifluoroacetyl chloride and anhydrous hydrogen iodide are passed through a preheater and heated to a temperature of about 100°C. The heated reactants are passed through a stainless steel tube having a diameter of 3 / 8 inch (9.5mm) and a length of 6 inches (152mm). According to the experiment, the tube is heated to a temperature within the range of 200°C to 350°C, and is purged with nitrogen for at least one hour before each experiment to remove any water. In twenty-one experiments, the tube contains one of several catalysts. In the remaining two experiments, the tube does not contain a catalyst. The contact time varies from 10 seconds to 30 seconds. All exhaust vapors of each experiment are collected in a sample bag for GC and GC-MS analysis. The results are shown in Table 1, Table 2 and Table 3.

[0134] Table 1 lists the reaction conditions (temperature, contact time, and catalyst used) for each of the twenty-three experiments. Table 2 lists the GC area % of the major organic compounds of interest corresponding to each of the twenty-three experiments. Table 3 lists the conversion percentages and selectivity percentages for trifluoroiodomethane, trifluoroacetyl iodide, and the combination of trifluoroiodomethane and trifluoroacetyl iodide corresponding to each of the twenty-three experiments. The conversion percentages and selectivity percentages are based on the GC area % data.

[0135] As shown in Tables 1, 2 and 3, the method described above with reference to Equation 1 can produce trifluoroacetyl iodide with a conversion percentage of over 90% and a selectivity percentage of over 99%. Therefore, Tables 1, 2 and 3 demonstrate methods for producing trifluoroacetyl iodide according to the present disclosure, which produce surprisingly good results.

[0136] Table 1

[0137]

[0138]

[0139] Table 2

[0140]

[0141]

[0142] Table 3

[0143]

[0144]

[0145] Example 2: Preparation of trifluoroacetyl iodide at a higher reaction temperature according to equation 1

[0146] In this example, the production of trifluoroacetyl iodide from hydrogen iodide and trifluoroacetyl chloride at elevated reaction temperatures according to Equation 1 as described above is demonstrated. Trifluoroacetyl chloride at a flow rate of 8.34 g / hr and hydrogen iodide at a flow rate of 14.08 g / hr were passed through a stainless steel tube having a diameter of 3 / 8 inch (9.5 mm) and a length of 6 inches (152 mm). The tube was heated to approximately 300°C and purged with nitrogen for at least one hour prior to the experiment to remove any water. The tube contained Stainless steel catalyst, contact time was about 10 seconds. The process was run continuously for 6.25 hours. The output of the reactor was collected in two dry ice traps, one at about 0°C to -5°C, and the other at about -78°C.

[0147] A total of 99.8 g of material was collected and a portion was analyzed by GC and GC-MS. The collected material was found to contain a mixture of trifluoroacetyl iodide and trifluoroacetyl chloride in a ratio of 60:40. The selectivity for trifluoroacetyl iodide was in the range of 88% to 97% based on GC area %.

[0148] Example 3: Preparation of trifluoroacetyl iodide at a higher reaction temperature according to equation 1

[0149] In this example, the manufacture of trifluoroacetyl iodide from hydrogen iodide and trifluoroacetyl chloride at a higher reaction temperature according to equation 1 as described above is demonstrated. Trifluoroacetyl chloride at a flow rate of 5.75 g / hour and hydrogen iodide at a flow rate of 13.9 g / hour were passed through a stainless steel tube having a diameter of 1 / 2 inch (12.7 mm) and a length of 6 inches (152 mm). The tube was heated to about 250°C and purged with nitrogen for at least one hour before the experiment to remove any water. The tube contained a 0.5% alumina carrier supported palladium (3.2 mm pellets) catalyst with a contact time of about 15 seconds. The process was run continuously for 5.25 hours. The output of the reactor was collected in two dry ice traps, one about 0°C to -5°C, and the other about -78°C.

[0150] A total of 89 g of material was collected and a portion was analyzed by GC-MS. The collected material was found to contain a mixture of trifluoroacetyl iodide and trifluoroacetyl chloride in a ratio of 70:30. The selectivity of trifluoroacetyl iodide to trifluoroiodomethane was in the range of 92% to 98% based on GC area %. This example was repeated with a silicon carbide (3 mm pellet) catalyst with similar results.

[0151] Example 4: Preparation of trifluoroacetyl iodide at a lower reaction temperature according to equation 1

[0152] In this embodiment, trifluoroacetyl iodide is produced from hydrogen iodide and trifluoroacetyl chloride at a relatively low temperature according to equation 1 as described above. Trifluoroacetyl chloride and anhydrous hydrogen iodide in a specific molar ratio are passed through a metal tube having a diameter of 3 / 4 inch (19.05 mm). The pressure is controlled using a pressure transducer and a control valve at the reactor outlet. According to the experiment, the tube is heated to a temperature in the range of 40°C to 210°C. In twenty-six of the twenty-eight experiments, the tube contained one of several catalysts. In the remaining two experiments, the tube did not contain a catalyst. The contact time varied from 6.1 seconds to 71.7 seconds. The reactor effluent of each experiment was passed through a heat tracer line to prevent condensation of trifluoroacetyl iodine, and was directed to a dry ice trap to capture the crude product. The uncondensed vapor escaping from the dry ice trap was directed to a water scrubber and an alkali scrubber. Samples were taken from the reactor effluent for GC and GC-MS analysis. The contact time in the reactor for each experiment was calculated based on the combined feed rate of trifluoroacetyl chloride and hydrogen iodide. The run time ranged from 8 hours to 49 hours. At the end of the reaction run time of each experiment, the system was shut down and the weights of all containers were weighed to achieve the purpose of mass balance. The crude product collected in the dry ice trap was also sampled and analyzed by GC and GC-MS. The results are shown in Tables 4 and 5.

[0153] Table 4 lists the reaction conditions (temperature, molar ratio, contact time, reactor type, pressure and catalyst used) for each of the twenty-eight experiments. Table 5 lists the GC area % of the major organic compounds of interest, as well as the conversion percentage of trifluoroacetyl chloride and the selectivity to trifluoroacetyl iodide corresponding to each of the twenty-eight experiments. The conversion percentage and selectivity percentage are based on the GC area % data.

[0154] As shown in Tables 4 and 5, the process described above with reference to Equation 1, operating at a reaction temperature equal to or less than about 120° C., can produce trifluoroacetyl iodide and trifluoroiodomethane at a concentration of less than 0.002% of the total organic compounds or about 20 ppm, with a conversion percentage exceeding 80% (using a catalyst and a ratio of trifluoroacetyl chloride to hydrogen of about one), and a selectivity to trifluoroacetyl iodide of 99 mole % or more. Thus, Tables 4 and 5 demonstrate a process for producing trifluoroacetyl iodide according to the present disclosure that produces surprisingly good results.

[0155] Table 4

[0156]

[0157]

[0158] Table 5

[0159]

[0160]

[0161] Example 5: Effect of Trifluoroacetyl Iodide on the Life of SiC Catalyst at a Lower Reaction Temperature According to Equation 1 Evaluate

[0162] In this embodiment, the life of silicon carbide catalyst (SiC1-E3-M) is evaluated when trifluoroacetyl iodide is manufactured by hydrogen iodide and trifluoroacetyl chloride at 90 ° C according to equation 1. In this embodiment, 20mL silicon carbide catalyst is loaded into an Inconel 600 tube with a diameter of 3 / 4 inch (19.05mm). The pressure transducer and control valve at the reactor outlet are used to control the pressure to 20psig (138kPaG). The system is closed regularly to check whether mass balance is reached and crude product is collected for analysis. The process is repeated for five extended series runs in a total operating time of more than 455 hours. The results are shown in Table 6.

[0163] Table 6 lists the reaction conditions (molar ratio, contact time, run time, and cumulative run time) for each of the five consecutive runs. Table 6 also lists the percent conversion of trifluoroacetyl chloride, the selectivity to trifluoroacetyl iodide, and the GC area % of trifluoroiodomethane for each of the five consecutive runs. The percent conversion and selectivity are based on the GC area % data.

[0164] As shown in Table 6, the process described above with reference to Equation 1, operating at a reaction temperature of 90°C, was able to produce trifluoroacetyl iodide without the formation of detectable trifluoroiodomethane. No deactivation of the silicon carbide catalyst was observed over the 455 hours of operation.

[0165] Table 6

[0166]

[0167]

[0168] Example 6: Effect of the life of activated carbon catalyst on the production of trifluoroacetyl iodide at a lower reaction temperature according to Equation 1 Evaluation

[0169] In this embodiment, the life of an activated carbon catalyst (Norit ROX0.8) is evaluated at 90°C when trifluoroacetyl iodide is produced from hydrogen iodide and trifluoroacetyl chloride according to equation 1. In this embodiment, 20 mL of activated carbon catalyst is loaded into an Inconel 600 tube having a diameter of 3 / 4 inch (19.05 mm). The pressure is controlled using a pressure transducer and a control valve at the reactor outlet. The system is shut down periodically to check whether mass balance is reached and to collect the crude product for analysis. The process is repeated for an extended twenty-nine series of runs over a total operating time of more than 2,000 hours. The results are shown in Table 7.

[0170] Table 7 lists the reaction conditions (pressure, molar ratio, contact time, run time, and cumulative run time) for each of the twenty-nine consecutive runs. Table 7 also lists the percent conversion of trifluoroacetyl chloride, the selectivity to trifluoroacetyl iodide, and the GC area % of trifluoroiodomethane for each of the twenty-nine consecutive runs. The percent conversion and selectivity are based on the GC area % data.

[0171] As shown in Table 7, the process described above with reference to Equation 1, operating at a reaction temperature of 90°C, was able to produce trifluoroacetyl iodide without the formation of detectable trifluoroiodomethane. No deactivation of the activated carbon catalyst was observed over the 2,051 hours of operation.

[0172] Table 7

[0173]

[0174]

[0175]

[0176] Example 7: Separation of trifluoroacetyl iodide

[0177] In this example, the separation of trifluoroacetyl iodide is described. A mixture comprising about 80 weight percent trifluoroacetyl iodide, about 10 weight percent trifluoroacetyl chloride, about 5 weight percent hydrogen iodide, and about 5 weight percent hydrogen chloride can be added to a distillation column. The distillation column can include a 10-gallon reboiler, a 2-inch inner diameter 10-foot The distillation column can be equipped with temperature, absolute pressure and differential pressure transmitters. The distillation can be carried out at a pressure of about 300 kPaG and a temperature of about 55°C, wherein hydrogen chloride is discharged from the top of the column and the product is discharged from the bottom of the column.

[0178] Example 8: Preparation of trifluoroiodomethane from trifluoroacetyl iodide using activated carbon catalyst at atmospheric pressure according to equation 2

[0179] In this embodiment, it is demonstrated that trifluoroiodomethane is made by trifluoroacetyl iodide at atmospheric pressure according to the above equation 2. A mixture of 55 GC area % of trifluoroacetyl iodide and 45 GC area % of trifluoroacetyl chloride is passed through a preheater and heated to a temperature of about 100 ° C. The heated reactants are passed through a stainless steel tube having a diameter of 3 / 8 inch (9.5 mm) and a length of 6 inches (152 mm). The tube is heated to about 350 ° C and purged with nitrogen for at least one hour before the experiment to remove any water. The tube contains a Norit-PK35 activated carbon catalyst with a contact time of about 10-15 seconds. The output of the reactor is collected in a sample bag for GC and GC-MS analysis.

[0180] Almost complete conversion of trifluoroacetyl iodide to trifluoroiodomethane was observed. The ratio of trifluoroiodomethane to unreacted trifluoroacetyl iodide was 54:0.22 based on GC area % measurement, with less than 0.5% unreacted trifluoroacetyl iodide.

[0181] Example 9: Preparation of trifluoroacetyl iodide from trifluoroacetyl iodide at above atmospheric pressure without catalyst according to Equation 2 Fluoroiodomethane

[0182] In this embodiment, trifluoroiodomethane is produced by trifluoroacetyl iodide at a pressure higher than atmospheric pressure and in the absence of a separate catalyst according to the above equation 2. A feed stream of at least 99.22 GC area % of trifluoroacetyl iodide is passed through a heating tube. The heating tube is a commercially pure (>99%) wrought nickel tube with a diameter of 0.5 inches (12.7 mm), wherein the length of the heating zone is 120 mm. The flow rate through produces a contact time of about 10 seconds. The tube does not contain a catalyst. The feed has a contact time of about 10 seconds. The pressure is controlled using a pressure transducer and a control valve at the reactor outlet. The output of the reactor is collected in a sample bag for GC and GC-MS analysis. The results are shown in Table 8.

[0183] Table 8 lists the reaction conditions (temperature, pressure) for each of the twenty experiments. Table 8 also lists the conversion percentage of trifluoroacetyl iodide and the selectivity to trifluoroiodomethane for each of the twenty experiments. The conversion and selectivity percentages are based on GC area % data. Table 8 also lists the GC area % of the major organic compounds of interest corresponding to some of the twenty-eight experiments.

[0184] Considering the results of Experiments 1-10 as shown in Table 8, the process described above with reference to Equation 2 operating at a higher reaction pressure is capable of producing trifluoroiodomethane with high conversion of trifluoroacetyl iodide and high selectivity to form trifluoroiodomethane. This effect is observed without the use of a catalyst (other than any catalytic effect provided by the nickel reactor itself). While the use of a catalyst may provide improved results, especially at lower reaction temperatures, not having to regenerate or replace the catalyst may provide a more efficient process overall.

[0185] Considering the results of Experiments 11-20 as shown in Table 8, it is shown that in the absence of a catalyst, the improved results are particularly significant at higher pressures and higher temperatures, with improved results shown at temperatures of 300°C or higher and an operating pressure of 200 psig (Experiments 11-15) compared to operating at atmospheric pressure (Experiments 16-20).

[0186] Table 8

[0187]

[0188]

[0189] Example 10: Separation of trifluoroiodomethane

[0190] In this example, the separation of trifluoroiodomethane is described. A mixture comprising about 85 weight percent trifluoroiodomethane, about 10 weight percent trifluoroacetyl iodide, and about 5 weight percent carbon monoxide can be fed to a distillation column. The distillation column can include a 10-gallon reboiler at a temperature of about 25° C., a 2-inch inner diameter 10-foot diaphragm from Cannon Instrument Company, State College, PA, and a 10-gallon reboiler. The distillation column can be equipped with temperature, absolute pressure and differential pressure transmitters. The distillation can be operated at a pressure of about 275 kPaG, and the condenser can be operated at a temperature of about -13°C to collect trifluoroiodomethane.

[0191] aspect

[0192] Aspect 1 is a gas-phase method for producing trifluoroiodomethane, the method comprising: providing a reactant stream comprising hydrogen iodide and at least one trifluoroacetyl halide, the trifluoroacetyl halide being selected from: trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof; reacting the reactant stream at a first reaction temperature of about 25°C to about 400°C in the presence of a first catalyst to produce an intermediate product stream comprising trifluoroacetyl iodide; and reacting the intermediate product stream at a second reaction temperature of about 200°C to about 600°C in the presence of a second catalyst to produce a final product stream comprising the trifluoroiodomethane.

[0193] Aspect 2 is the method of aspect 1, wherein in the step of reacting the reactant stream, the first reaction temperature is from about 40°C to about 120°C.

[0194] Aspect 3 is the method of aspect 1, wherein in the step of reacting the reactant stream, the first reaction temperature is from about 70°C to about 100°C.

[0195] Aspect 4 is the method of aspect 1, wherein in the step of reacting the reactant stream, the first reaction temperature is from about 80°C to about 100°C.

[0196] Aspect 5 is the method of any one of aspects 1-4, wherein in the providing step, the reactant stream comprises less than about 500 ppm by weight of oxygen.

[0197] Aspect 6 is the method of any one of aspects 1-4, wherein in the providing step, the reactant stream comprises less than about 100 ppm by weight of oxygen.

[0198] Aspect 7 is the method of any one of aspects 1-4, wherein in the providing step, the reactant stream comprises less than about 10 ppm by weight of oxygen.

[0199] Aspect 8 is the method of any one of aspects 1-4, wherein in the providing step, the reactant stream comprises less than about 1 ppm by weight of oxygen.

[0200] Aspect 9 is the method of any one of aspects 1-8, wherein in the providing step, the hydrogen iodide comprises less than about 500 ppm by weight of water.

[0201] Aspect 10 is the method of any one of aspects 1-8, wherein in the providing step, the hydrogen iodide comprises less than about 100 ppm by weight of water.

[0202] Aspect 11 is the method of any one of aspects 1-8, wherein in the providing step, the hydrogen iodide comprises less than about 10 ppm by weight of water.

[0203] Aspect 12 is the method of any one of aspects 1-8, wherein in the providing step, the hydrogen iodide comprises less than about 1 ppm by weight of water.

[0204] Aspect 13 is the method of any one of aspects 1-12, wherein in the providing step, the molar ratio of the hydrogen iodide to the trifluoroacetyl halide is from about 0.1:1 to about 10:1.

[0205] Aspect 14 is the method of any one of aspects 1-12, wherein in the providing step, the molar ratio of the hydrogen iodide to the trifluoroacetyl halide is from about 0.5:1 to about 2.0:1.

[0206] Aspect 15 is the method of any one of aspects 1-12, wherein in the providing step, the molar ratio of the hydrogen iodide to the trifluoroacetyl halide is from about 0.6:1 to about 1.2:1.

[0207] Aspect 16 is the method of any one of aspects 1-12, wherein in the providing step, the molar ratio of the hydrogen iodide to the trifluoroacetyl halide is from about 0.7:1 to about 1.0:1.

[0208] Aspect 17 is a method according to any one of Aspects 1 to 16, wherein in the step of reacting the reactant flow, the first catalyst comprises activated carbon, mesophase carbon, stainless steel, nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, alumina, platinum, palladium, metal carbide, non-metal carbide or a combination thereof.

[0209] Aspect 18 is the method of any one of aspects 1-16, wherein the first catalyst comprises activated carbon, mesophase carbon, stainless steel, platinum on a carrier, palladium on a carrier, silicon carbide, or a combination thereof.

[0210] Aspect 19 is the method of any one of aspects 1-16, wherein the first catalyst comprises platinum on a carrier, palladium on a carrier, activated carbon, silicon carbide, or a combination thereof.

[0211] Aspect 20 is the method of any one of aspects 1-16, wherein the first catalyst comprises activated carbon or silicon carbide.

[0212] Aspect 21 is the method of any one of aspects 1-20, wherein in the step of reacting the reactant stream, the reactant stream may be contacted with the first catalyst for a contact time of about 0.1 seconds to about 300 seconds.

[0213] Aspect 22 is the method of any one of aspects 1-20, wherein in the step of reacting the reactant stream, the reactant stream may be contacted with the first catalyst for a contact time of about 5 seconds to about 60 seconds.

[0214] Aspect 23 is the method of any one of aspects 1-20, wherein in the step of reacting the reactant stream, the reactant stream may be contacted with the first catalyst for a contact time of about 10 seconds to about 40 seconds.

[0215] Aspect 24 is the method of any one of aspects 1-20, wherein in the step of reacting the reactant stream, the reactant stream may be contacted with the first catalyst for a contact time of about 15 seconds to about 35 seconds.

[0216] Aspect 25 is the method of any of aspects 1-24, wherein the step of reacting the reactant stream is performed at a pressure of about atmospheric pressure to about 300 psig (2,068 kPaG).

[0217] Aspect 26 is the method of any of aspects 1-24, wherein the step of reacting the reactant stream is carried out at a pressure of about 5 psig (34 kPaG) to about 200 psig (1,379 kPaG).

[0218] Aspect 27 is the method of any of aspects 1-24, wherein the step of reacting the reactant stream is carried out at a pressure of about 10 psig (69 kPaG) to about 150 psig (1,034 kPaG).

[0219] Aspect 28 is the method of any of aspects 1-24, wherein the step of reacting the reactant stream is carried out at a pressure of about 20 psig (138 kPaG) to about 100 psig (689 kPaG).

[0220] Aspect 29 is the method of any one of aspects 1-28, wherein in the step of reacting the intermediate product stream, the second reaction temperature is from about 250°C to about 500°C.

[0221] Aspect 30 is the method of any one of aspects 1-28, wherein in the step of reacting the intermediate product stream, the second reaction temperature is from about 300°C to about 400°C.

[0222] Aspect 31 is the method of any one of aspects 1-28, wherein in the step of reacting the intermediate product stream, the second reaction temperature is from about 300°C to about 350°C.

[0223] Aspect 32 is the method of any one of aspects 1-31, wherein in the step of reacting the intermediate product stream, the intermediate product stream may be contacted with the second catalyst for a contact time of about 0.1 seconds to about 300 seconds.

[0224] Aspect 33 is the method of any one of aspects 1-31, wherein in the step of reacting the intermediate product stream, the intermediate product stream may be contacted with the second catalyst for a contact time of about 1 second to about 60 seconds.

[0225] Aspect 34 is the method of any one of aspects 1-31, wherein in the step of reacting the intermediate product stream, the intermediate product stream may be contacted with the second catalyst for a contact time of about 2 seconds to about 50 seconds.

[0226] Aspect 35 is the method of any one of aspects 1-31, wherein in the step of reacting the intermediate product, the intermediate product stream may be contacted with the second catalyst for a contact time of about 3 seconds to about 30 seconds.

[0227] Aspect 36 is a method according to any one of Aspects 1 to 35, wherein in the step of reacting the intermediate product stream, the second catalyst comprises stainless steel, nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, aluminum oxide, silicon carbide, platinum, palladium, rhenium, activated carbon, mesophase carbon, or a combination thereof.

[0228] Aspect 37 is a method of any one of Aspects 1-35, wherein in the step of reacting the intermediate product stream, the second catalyst comprises activated carbon, about 0.1 weight % to about 1 weight % of supported platinum, about 0.1 weight % to about 1 weight % of supported palladium, about 0.1 weight % to about 1 weight % of supported rhenium, or a combination thereof.

[0229] Aspect 38 is the method of any one of aspects 1-35, wherein in the step of reacting the intermediate product stream, the second catalyst comprises activated carbon or about 0.3 wt % to about 0.7 wt % palladium on a support.

[0230] Aspect 39 is the method of any one of aspects 1-35, wherein in the step of reacting the intermediate product stream, the second catalyst comprises activated carbon.

[0231] Aspect 40 is the method of any one of aspects 1-35, wherein in the step of reacting the intermediate product stream, the second catalyst consists of a reactor surface in contact with the intermediate product stream.

[0232] Aspect 41 is the method of any of aspects 1-40, wherein the step of reacting the intermediate product stream is carried out at a pressure of about 5 psig (34 kPaG) to about 300 psig (2,068 kPaG).

[0233] Aspect 42 is a gas phase method for producing trifluoroiodomethane, the method 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 at a first reaction temperature of about 25° C. to about 400° C. and a pressure of about atmospheric pressure to about 300 psig (2,068 kPaG) for a first contact time of about 0.1 second to about 300 seconds in the presence of a first catalyst to produce an intermediate product stream comprising trifluoroacetyl iodide; and reacting the intermediate product stream at a temperature of about 100° C. to about 200° C. in the presence of a second catalyst. The method comprises reacting the catalyst at a second reaction temperature of 200° C. to about 600° C. for a second contact time of about 0.1 second to about 300 seconds to produce a final product stream comprising trifluoroiodomethane, wherein the molar ratio of the hydrogen iodide to the trifluoroacetyl halide is from about 0.1:1 to about 10:1, and the first catalyst comprises activated carbon, mesophase carbon, stainless steel, nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, alumina, platinum, palladium, metal carbide, non-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, alumina, silicon carbide, platinum, palladium, rhenium, activated carbon, mesophase carbon or a combination thereof.

[0234] Aspect 43 is a gas phase method for producing trifluoroiodomethane, the method 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 at a first reaction temperature of about 40° C. to about 120° C. and a pressure of about 5 psig (34 kPaG) to about 200 psig (1,379 kPaG) for a first contact time of about 5 seconds to about 60 seconds in the presence of a first catalyst to produce an intermediate product stream comprising trifluoroacetyl iodide; and reacting the reactant stream at a first reaction temperature of about 40° C. to about 120° C. and a pressure of about 5 psig (34 kPaG) to about 200 psig (1,379 kPaG) in the presence of a second catalyst for a first contact time of about 5 seconds to about 60 seconds ... in the presence of a second catalyst. , reacting the intermediate product stream at a second reaction temperature of about 250° C. to about 500° C. for a second contact time of about 1 second to about 60 seconds to produce a final product stream comprising the trifluoroiodomethane, wherein the molar ratio of the hydrogen iodide to the trifluoroacetyl halide is about 0.5:1 to about 2:1, the first catalyst comprises activated carbon, mesophase carbon, stainless steel, platinum on a carrier, palladium on a carrier, silicon carbide, or a combination thereof, and the second catalyst comprises activated carbon, about 0.1 wt % to about 1 wt % of platinum on a carrier, about 0.1 wt % to about 1 wt % of palladium on a carrier, about 0.1 wt % to about 1 wt % of rhenium on a carrier, or a combination thereof.

[0235] Aspect 44 is a gas phase method for producing trifluoroiodomethane, the method 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 at a first reaction temperature of about 70° C. to about 100° C. and a pressure of about 10 psig (69 kPaG) to about 150 psig (1,034 kPaG) for a first contact time of about 10 seconds to about 40 seconds in the presence of a first catalyst to produce trifluoroiodomethane. An intermediate product stream of trifluoroacetyl iodide; and reacting the intermediate product stream at a second reaction temperature of about 300° C. to about 400° C. for a second contact time of about 2 seconds to about 50 seconds in the presence of a second catalyst to produce a final product stream comprising trifluoroiodomethane, wherein the molar ratio of hydrogen iodide to the trifluoroacetyl halide is about 0.6:1 to about 1.2:1, wherein the first catalyst comprises platinum on a carrier, palladium on a carrier, activated carbon, silicon carbide or a combination thereof, and the second catalyst comprises activated carbon or about 0.3 wt % to about 0.7 wt % palladium on a carrier.

[0236] Aspect 45 is a gas phase method for producing trifluoroiodomethane, the method 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 at a first reaction temperature of about 80° C. to about 100° C. and a pressure of about 10 psig (69 kPaG) to about 150 psig (1,034 kPaG) for about 15 seconds to about 35 seconds in the presence of a first catalyst; A first contact time to produce an intermediate product stream comprising trifluoroacetyl iodide; and in the presence of a second catalyst, reacting the intermediate product stream at a second reaction temperature of about 300° C. to about 350° C. for a second contact time of about 3 seconds to about 30 seconds to produce a final product stream comprising trifluoroiodomethane, wherein the molar ratio of hydrogen iodide to the trifluoroacetyl halide is about 0.7:1 to about 1.0:1, wherein the first catalyst comprises platinum on a carrier, palladium on a carrier, silicon carbide or a combination thereof, and the second catalyst comprises activated carbon.

[0237] Aspect 46 is the method of any one of aspects 42-47, wherein in the providing step, the reactant stream comprises less than about 500 ppm by weight of oxygen and the hydrogen iodide comprises less than about 500 ppm by weight of water.

[0238] Aspect 47 is the method of any one of aspects 42-47, wherein in the providing step, the reactant stream comprises less than about 100 ppm by weight of oxygen and the hydrogen iodide comprises less than about 100 ppm by weight of water.

[0239] Aspect 48 is the method of any one of aspects 42-47, wherein in the providing step, the reactant stream comprises less than about 10 ppm by weight of oxygen and the hydrogen iodide comprises less than about 10 ppm by weight of water.

[0240] Aspect 49 is the method of any one of aspects 42-47, wherein in the providing step, the reactant stream comprises less than about 1 ppm by weight of oxygen and the hydrogen iodide comprises less than about 1 ppm by weight of water.

[0241] Aspect 50 is the method of any one of aspects 1-49, wherein in the providing step, the trifluoroacetyl halide comprises trifluoroacetyl chloride.

[0242] Aspect 51 is a method according to any one of Aspects 1 to 50, wherein the organic compounds in the intermediate product stream comprise, based on the GC area % of total organic compounds, about 10% to about 99% of trifluoroacetyl iodide, about 1% to about 90% of unreacted trifluoroacetyl halide, less than about 0.010% of trifluoroiodomethane, and less than about 15% of organic compounds other than trifluoroacetyl iodide, trifluoroacetyl halide, and trifluoroiodomethane.

[0243] Aspect 52 is a method according to any one of Aspects 1 to 50, wherein the organic compounds in the intermediate product stream comprise, based on the GC area % of total organic compounds, about 50% to about 99% of trifluoroacetyl iodide, about 1% to about 50% of unreacted trifluoroacetyl halide, less than about 0.002% of trifluoroiodomethane, and less than about 8% of organic compounds other than trifluoroacetyl iodide, trifluoroacetyl halide, and trifluoroiodomethane.

[0244] Aspect 53 is a method according to any one of Aspects 1 to 50, wherein the organic compounds in the intermediate product stream comprise, based on the GC area % of total organic compounds, about 60% to about 99% of trifluoroacetyl iodide, about 1% to about 40% of unreacted trifluoroacetyl halide, less than about 0.001% of trifluoroiodomethane, and less than about 4% of organic compounds other than trifluoroacetyl iodide, trifluoroacetyl halide, and trifluoroiodomethane.

[0245] Aspect 54 is a method according to any one of aspects 1 to 50, wherein the organic compounds in the intermediate product stream comprise, based on the GC area % of total organic compounds, about 70% to about 99% of trifluoroacetyl iodide, about 1% to about 30% of unreacted trifluoroacetyl halide, less than about 0.0005% of trifluoroiodomethane, and less than about 2% of organic compounds other than trifluoroacetyl iodide, trifluoroacetyl halide, and trifluoroiodomethane.

[0246] Aspect 55 is the method of any one of Aspects 1-54, further comprising the following additional steps: separating unreacted trifluoroacetyl halide from the intermediate product stream, returning the separated trifluoroacetyl halide to the reaction stream, separating unreacted hydrogen iodide from the intermediate product stream, returning the unreacted hydrogen iodide to the reaction stream, separating unreacted trifluoroacetyl iodide from the final product stream, and returning the separated unreacted trifluoroacetyl iodide to the intermediate product stream.

[0247] Aspect 56 is a gas-phase method for producing trifluoroacetyl iodide, the method comprising: providing a reactant stream comprising hydrogen iodide and at least one trifluoroacetyl halide, the trifluoroacetyl halide being selected from: trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof; and reacting the reactant stream at a reaction temperature of about 25°C to about 400°C in the presence of a first catalyst to produce a product stream comprising trifluoroacetyl iodide.

[0248] Aspect 57 is the method of aspect 56, wherein in the step of reacting the reactant stream, the reaction temperature is from about 40°C to about 120°C.

[0249] Aspect 58 is the method of aspect 56, wherein in the step of reacting the reactant stream, the reaction temperature is from about 70°C to about 100°C.

[0250] Aspect 59 is the method of aspect 56, wherein in the step of reacting the reactant stream, the reaction temperature is from about 80°C to about 100°C.

[0251] Aspect 60 is the method of any of aspects 56-59, wherein in the providing step, the reactant stream comprises less than about 500 ppm by weight of oxygen.

[0252] Aspect 61 is the method of any of aspects 56-59, wherein in the providing step, the reactant stream comprises less than about 100 ppm by weight of oxygen.

[0253] Aspect 62 is the method of any of aspects 56-59, wherein in the providing step, the reactant stream comprises less than about 10 ppm by weight of oxygen.

[0254] Aspect 63 is the method of any of aspects 56-59, wherein in the providing step, the reactant stream comprises less than about 1 ppm by weight of oxygen.

[0255] Aspect 64 is the method of any one of aspects 56-63, wherein in the providing step, the hydrogen iodide comprises less than about 500 ppm by weight of water.

[0256] Aspect 65 is the method of any one of aspects 56-63, wherein in the providing step, the hydrogen iodide comprises less than about 100 ppm by weight of water.

[0257] Aspect 66 is the method of any one of aspects 56-63, wherein in the providing step, the hydrogen iodide comprises less than about 10 ppm by weight of water.

[0258] Aspect 67 is the method of any one of aspects 56-63, wherein in the providing step, the hydrogen iodide comprises less than about 1 ppm by weight of water.

[0259] Aspect 68 is the method of any one of aspects 56-67, wherein in the providing step, the molar ratio of the hydrogen iodide to the trifluoroacetyl halide is from about 0.1:1 to about 10:1.

[0260] Aspect 69 is the method of any one of aspects 56-67, wherein in the providing step, the molar ratio of the hydrogen iodide to the trifluoroacetyl halide is from about 0.5:1 to about 2.0:1.

[0261] Aspect 70 is the method of any one of aspects 56-67, wherein in the providing step, the molar ratio of the hydrogen iodide to the trifluoroacetyl halide is from about 0.6:1 to about 1.2:1.

[0262] Aspect 71 is the method of any one of aspects 56-67, wherein in the providing step, the molar ratio of the hydrogen iodide to the trifluoroacetyl halide is from about 0.7:1 to about 1.0:1.

[0263] Aspect 72 is a method according to any one of Aspects 56 to 71, wherein in the step of reacting the reactant flow, the catalyst comprises activated carbon, mesophase carbon, stainless steel, nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, alumina, platinum, palladium, metal carbide, non-metal carbide or a combination thereof.

[0264] Aspect 73 is the method of any one of aspects 56-71, wherein the catalyst comprises activated carbon, mesophase carbon, stainless steel, platinum on a carrier, palladium on a carrier, silicon carbide, or a combination thereof.

[0265] Aspect 74 is the method of any one of aspects 56-71, wherein the catalyst comprises platinum on a support, palladium on a support, activated carbon, silicon carbide, or a combination thereof.

[0266] Aspect 75 is the method of any one of aspects 56-71, wherein the catalyst comprises activated carbon or silicon carbide.

[0267] Aspect 75 is the method of any one of aspects 56-75, wherein in the step of reacting the reactant stream, the reactant stream may be contacted with the catalyst for a contact time of about 0.1 seconds to about 300 seconds.

[0268] Aspect 77 is the method of any one of aspects 56-75, wherein in the step of reacting the reactant stream, the reactant stream may be contacted with the catalyst for a contact time of about 5 seconds to about 60 seconds.

[0269] Aspect 78 is the method of any one of aspects 56-75, wherein in the step of reacting the reactant stream, the reactant stream may be contacted with the catalyst for a contact time of about 10 seconds to about 40 seconds.

[0270] Aspect 79 is the method of any one of aspects 56-75, wherein in the step of reacting the reactant stream, the reactant stream may be contacted with the catalyst for a contact time of about 15 seconds to about 35 seconds.

[0271] Aspect 80 is the method of any of aspects 56-79, wherein the step of reacting the reactant stream is performed at a pressure of about atmospheric pressure to about 300 psig (2,068 kPaG).

[0272] Aspect 81 is the method of any of aspects 56-79, wherein the step of reacting the reactant stream is carried out at a pressure of about 5 psig (34 kPaG) to about 200 psig (1,379 kPaG).

[0273] Aspect 82 is the method of any of aspects 56-79, wherein the step of reacting the reactant stream is carried out at a pressure of about 10 psig (69 kPaG) to about 150 psig (1,034 kPaG).

[0274] Aspect 83 is the method of any of aspects 56-79, wherein the step of reacting the reactant stream is carried out at a pressure of about 20 psig (138 kPaG) to about 100 psig (689 kPaG).

[0275] Aspect 84 is a gas-phase method for producing trifluoroacetyl iodide, the method comprising: providing a reactant stream comprising hydrogen iodide and at least one trifluoroacetyl halide, the trifluoroacetyl halide selected from: trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof; reacting the reactant stream at a reaction temperature of about 25° C. to about 400° C. and a pressure of about atmospheric pressure to about 300 psig (2,068 kPaG) in the presence of a catalyst for a contact time of about 0.1 second to about 300 seconds to produce a product stream comprising the trifluoroacetyl iodide, wherein the molar ratio of hydrogen iodide to the trifluoroacetyl halide is from about 0.1:1 to about 10:1, and the catalyst comprises activated carbon, mesophase carbon, stainless steel, nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, alumina, platinum, palladium, metal carbide, non-metal carbide, or combinations thereof.

[0276] Aspect 85 is a gas-phase method for producing trifluoroacetyl iodide, the method comprising: providing a reactant stream comprising hydrogen iodide and at least one trifluoroacetyl halide, the trifluoroacetyl halide being selected from: trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof; reacting the reactant stream at a reaction temperature of about 40° C. to about 120° C. and a pressure of about 5 psig (34 kPaG) to about 200 psig (1,379 kPaG) for a contact time of about 5 seconds to about 60 seconds in the presence of a catalyst to produce a product stream comprising trifluoroacetyl iodide, wherein the molar ratio of hydrogen iodide to the trifluoroacetyl halide is about 0.5:1 to about 2:1, and the catalyst comprises activated carbon, mesophase carbon, stainless steel, platinum on a support, palladium on a support, silicon carbide, or combinations thereof.

[0277] Aspect 86 is a gas-phase method for producing trifluoroacetyl iodide, the method comprising: providing a reactant stream comprising hydrogen iodide and at least one trifluoroacetyl halide, the trifluoroacetyl halide being selected from: trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof; reacting the reactant stream at a reaction temperature of about 70° C. to about 100° C. and a pressure of about 10 psig (69 kPaG) to about 150 psig (1,034 kPaG) for a contact time of about 10 seconds to about 40 seconds in the presence of a catalyst to produce a product stream comprising trifluoroacetyl iodide, wherein the molar ratio of hydrogen iodide to the trifluoroacetyl halide is about 0.6:1 to about 1.2:1, and the catalyst comprises platinum on a support, palladium on a support, activated carbon, silicon carbide, or a combination thereof.

[0278] Aspect 87 is a gas-phase method for producing trifluoroacetyl iodide, the method comprising: providing a reactant stream comprising hydrogen iodide and at least one trifluoroacetyl halide, the trifluoroacetyl halide being selected from: trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof; reacting the reactant stream at a reaction temperature of about 80°C to about 100°C and a pressure of about 10 psig (69 kPaG) to about 150 psig (1,034 kPaG) for a contact time of about 15 seconds to about 35 seconds in the presence of a catalyst to produce a product stream comprising trifluoroacetyl iodide, wherein the molar ratio of hydrogen iodide to the trifluoroacetyl halide is about 0.7:1 to about 1.0:1, and the catalyst comprises platinum on a support, palladium on a support, silicon carbide, or a combination thereof.

[0279] Aspect 88 is the method of any one of aspects 84-87, wherein in the providing step, the reactant stream comprises less than about 500 ppm by weight of oxygen and the hydrogen iodide comprises less than about 500 ppm by weight of water.

[0280] Aspect 89 is the method of any one of aspects 84-87, wherein in the providing step, the reactant stream comprises less than about 100 ppm by weight of oxygen and the hydrogen iodide comprises less than about 100 ppm by weight of water.

[0281] Aspect 90 is the method of any one of aspects 84-87, wherein in the providing step, the reactant stream comprises less than about 10 ppm by weight of oxygen and the hydrogen iodide comprises less than about 10 ppm by weight of water.

[0282] Aspect 91 is the method of any one of aspects 84-87, wherein in the providing step, the reactant stream comprises less than about 1 ppm by weight of oxygen and the hydrogen iodide comprises less than about 1 ppm by weight of water.

[0283] Aspect 92 is the method of any one of aspects 56-91, wherein in the providing step, the trifluoroacetyl halide comprises trifluoroacetyl chloride.

[0284] Aspect 93 is a composition comprising at least 98 wt % trifluoroacetyl iodide and a total of about 1 ppm to about 20,000 ppm (about 2 wt %) of a compound selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane.

[0285] Aspect 94 is a composition comprising at least 99 wt% trifluoroacetyl iodide and a total of 1 ppm to 10,000 ppm (1 wt%) of a compound selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane.

[0286] Aspect 95 is a composition comprising at least 99.5 wt% trifluoroacetyl iodide and 1 ppm to 5,000 ppm total of a compound selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane.

[0287] Aspect 96 is a composition comprising at least 99.7 wt % trifluoroacetyl iodide and 1 ppm to 3,000 ppm total of a compound selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane.

[0288] Aspect 97 is a composition consisting essentially of at least 98 wt % trifluoroacetyl iodide and a total of about 1 ppm to about 20,000 ppm (about 2 wt %) of a compound selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane.

[0289] Aspect 98 is a composition consisting essentially of at least 99 wt % trifluoroacetyl iodide and a total of 1 ppm to 10,000 ppm (1 wt %) of a compound selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane.

[0290] Aspect 99 is a composition consisting essentially of at least 99.5 wt% trifluoroacetyl iodide and 1 ppm to 5,000 ppm total of a compound selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane.

[0291] Aspect 100 is a composition consisting essentially of at least 99.7 wt % trifluoroacetyl iodide and 1 ppm to 3,000 ppm total of a compound selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane.

[0292] Aspect 101 is a composition consisting of at least 98 wt % trifluoroacetyl iodide and a total of about 1 ppm to about 20,000 ppm (about 2 wt %) of a compound selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane.

[0293] Aspect 102 is a composition consisting of at least 99 wt% trifluoroacetyl iodide and a total of 1 ppm to 10,000 ppm (1 wt%) of a compound selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane.

[0294] Aspect 103 is a composition consisting of at least 99.5 wt% trifluoroacetyl iodide and 1 ppm to 5,000 ppm total of a compound selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane.

[0295] Aspect 104 is a composition consisting of at least 99.7 wt % trifluoroacetyl iodide and 1 ppm to 3,000 ppm total of a compound selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, trifluoroiodomethane, trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetic acid, and chlorotrifluoromethane.

[0296] Aspect 105 is a composition comprising at least 99 wt% 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, less than 1 ppm of hydrogen chloride, and a total of 1 ppm to 500 ppm of a compound selected from the group consisting of trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde, and trifluoroacetyl chloride.

[0297] Aspect 106 is a composition comprising at least 99.5 wt% of trifluoroiodomethane, 1 ppm to 250 ppm of chlorotrifluoroethane, less than 250 ppm of hexafluoroethane, less than 250 ppm of trifluoromethane, less than 50 ppm of carbon monoxide, less than 0.5 ppm of hydrogen chloride, and a total of 1 ppm to 250 ppm of a compound selected from the group consisting of trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde, and trifluoroacetyl chloride.

[0298] Aspect 107 is a composition comprising at least 99.7 wt % of trifluoroiodomethane, 1 ppm to 100 ppm of chlorotrifluoroethane, less than 100 ppm of hexafluoroethane, less than 100 ppm of trifluoromethane, less than 20 ppm of carbon monoxide, less than 0.2 ppm of hydrogen chloride, and a total of 1 ppm to 100 ppm of a compound selected from the group consisting of trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde, and trifluoroacetyl chloride.

[0299] Aspect 108 is a composition comprising at least 99.9 wt % of trifluoroiodomethane, 1 ppm to 100 ppm of chlorotrifluoroethane, less than 100 ppm of hexafluoroethane, less than 100 ppm of trifluoromethane, less than 20 ppm of carbon monoxide, less than 0.2 ppm of hydrogen chloride, and a total of 1 ppm to 100 ppm of a compound selected from the group consisting of trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde, and trifluoroacetyl chloride.

[0300] Aspect 109 is a composition consisting essentially of at least 99 wt% trifluoroiodomethane, 1 ppm to 500 ppm chlorotrifluoroethane, less than 500 ppm hexafluoroethane, less than 500 ppm trifluoromethane, less than 100 ppm carbon monoxide, less than 1 ppm hydrogen chloride, and a total of 1 ppm to 500 ppm of a compound selected from the group consisting of trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde, and trifluoroacetyl chloride.

[0301] Aspect 110 is a composition consisting essentially of at least 99.5 wt. % trifluoroiodomethane, 1 ppm to 250 ppm chlorotrifluoroethane, less than 250 ppm hexafluoroethane, less than 250 ppm trifluoromethane, less than 50 ppm carbon monoxide, less than 0.5 ppm hydrogen chloride, and a total of 1 ppm to 250 ppm of a compound selected from the group consisting of trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde, and trifluoroacetyl chloride.

[0302] Aspect 111 is a composition consisting essentially of at least 99.7 wt % of trifluoroiodomethane, 1 ppm to 100 ppm of chlorotrifluoroethane, less than 100 ppm of hexafluoroethane, less than 100 ppm of trifluoromethane, less than 20 ppm of carbon monoxide, less than 0.2 ppm of hydrogen chloride, and a total of 1 ppm to 100 ppm of a compound selected from the group consisting of trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde, and trifluoroacetyl chloride.

[0303] Aspect 112 is a composition consisting essentially of at least 99.9 wt % of trifluoroiodomethane, 1 ppm to 100 ppm of chlorotrifluoroethane, less than 100 ppm of hexafluoroethane, less than 100 ppm of trifluoromethane, less than 20 ppm of carbon monoxide, less than 0.2 ppm of hydrogen chloride, and a total of 1 ppm to 100 ppm of a compound selected from the group consisting of trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde, and trifluoroacetyl chloride.

[0304] Aspect 109 is a composition consisting of at least 99 wt% trifluoroiodomethane, 1 ppm to 500 ppm chlorotrifluoroethane, less than 500 ppm hexafluoroethane, less than 500 ppm trifluoromethane, less than 100 ppm carbon monoxide, less than 1 ppm hydrogen chloride, and a total of 1 ppm to 500 ppm of a compound selected from the group consisting of trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde, and trifluoroacetyl chloride.

[0305] Aspect 110 is a composition consisting of at least 99.5 wt % of trifluoroiodomethane, 1 ppm to 250 ppm of chlorotrifluoroethane, less than 250 ppm of hexafluoroethane, less than 250 ppm of trifluoromethane, less than 50 ppm of carbon monoxide, less than 0.5 ppm of hydrogen chloride, and a total of 1 ppm to 250 ppm of a compound selected from the group consisting of trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde, and trifluoroacetyl chloride.

[0306] Aspect 111 is a composition consisting of at least 99.7 wt % of trifluoroiodomethane, 1 ppm to 100 ppm of chlorotrifluoroethane, less than 100 ppm of hexafluoroethane, less than 100 ppm of trifluoromethane, less than 20 ppm of carbon monoxide, less than 0.2 ppm of hydrogen chloride, and a total of 1 ppm to 100 ppm of a compound selected from the group consisting of trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde, and trifluoroacetyl chloride.

[0307] Aspect 112 is a composition consisting of at least 99.9 wt % of trifluoroiodomethane, 1 ppm to 100 ppm of chlorotrifluoroethane, less than 100 ppm of hexafluoroethane, less than 100 ppm of trifluoromethane, less than 20 ppm of carbon monoxide, less than 0.2 ppm of hydrogen chloride, and a total of 1 ppm to 100 ppm of a compound selected from the group consisting of trifluoroacetyl fluoride, hexafluoroacetone, trifluoroacetaldehyde, and trifluoroacetyl chloride.

[0308] Aspect 113 is a gas phase method for producing trifluoroiodomethane, the method comprising: providing a reactant stream comprising trifluoroacetyl iodide; and reacting the reactant stream at a reaction temperature of about 200° C. to about 600° C. in the presence of a catalyst to produce a product stream comprising the trifluoroiodomethane.

[0309] Aspect 114 is the method of aspect 113, wherein in the step of reacting the reactant stream, the reaction temperature is from about 250°C to about 500°C.

[0310] Aspect 115 is the method of aspect 113, wherein in the step of reacting the reactant stream, the reaction temperature is from about 300°C to about 400°C.

[0311] Aspect 116 is the method of aspect 113, wherein in the step of reacting the reactant stream, the reaction temperature is from about 300°C to about 350°C.

[0312] Aspect 117 is the method of any one of aspects 113-116, wherein in the step of reacting the reactant stream, the reactant stream may be contacted with the catalyst for a contact time of about 0.1 seconds to about 300 seconds.

[0313] Aspect 118 is the method of any one of aspects 113-116, wherein in the step of reacting the reactant stream, the reactant stream may be contacted with the catalyst for a contact time of about 1 second to about 60 seconds.

[0314] Aspect 119 is the method of any one of aspects 113-116, wherein in the step of reacting the reactant stream, the reactant stream may be contacted with the catalyst for a contact time of about 2 seconds to about 50 seconds.

[0315] Aspect 120 is the method of any one of aspects 113-116, wherein in the step of reacting the reactant stream, the reactant stream may be contacted with the catalyst for a contact time of about 3 seconds to about 30 seconds.

[0316] Aspect 121 is a method according to any one of Aspects 113 to 120, wherein in the step of reacting the reactant flow, the catalyst comprises stainless steel, nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, aluminum oxide, silicon carbide, platinum, palladium, rhenium, activated carbon, mesophase carbon, or a combination thereof.

[0317] Aspect 122 is a method of any one of Aspects 113-120, wherein in the step of reacting the reactant flow, the catalyst comprises activated carbon, about 0.1 weight % to about 1 weight % of supported platinum, about 0.1 weight % to about 1 weight % of supported palladium, about 0.1 weight % to about 1 weight % of supported rhenium, or a combination thereof.

[0318] Aspect 123 is the method of any one of aspects 113-120, wherein in the step of reacting the reactant stream, the catalyst comprises activated carbon or about 0.3 wt % to about 0.7 wt % palladium on a support.

[0319] Aspect 124 is the method of any one of aspects 113-120, wherein in the step of reacting the reactant stream, the catalyst comprises activated carbon.

[0320] Aspect 125 is the method of any one of aspects 113-120, wherein in the step of reacting the reactant stream, the catalyst consists of a reactor surface in contact with the reactant stream.

[0321] Aspect 126 is the method of any of aspects 113-125, wherein the step of reacting the reactant stream is carried out at a pressure of about 5 psig (34 kPaG) to about 300 psig (2,068 kPaG).

[0322] Aspect 127 is a gas phase method for producing trifluoroiodomethane, the method comprising: providing a reactant stream comprising trifluoroacetyl iodide; and reacting the reactant stream at a reaction temperature of about 200° C. to about 600° C. for a contact time of about 0.1 second to about 300 seconds in the presence of a catalyst to produce a product stream comprising the trifluoroiodomethane, wherein the catalyst comprises stainless steel, nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, aluminum oxide, silicon carbide, platinum, palladium, rhenium, activated carbon, mesophase carbon, or a combination thereof.

[0323] Aspect 128 is a gas phase method for producing trifluoroiodomethane, the method comprising: providing a reactant stream comprising trifluoroacetyl iodide; and reacting the reactant stream at a reaction temperature of about 250° C. to about 500° C. for a contact time of about 1 second to about 60 seconds in the presence of a catalyst to produce a product stream comprising the trifluoroiodomethane, wherein the catalyst comprises activated carbon, about 0.1 wt % to about 1 wt % of platinum on a carrier, about 0.1 wt % to about 1 wt % of palladium on a carrier, about 0.1 wt % to about 1 wt % of rhenium on a carrier, or a combination thereof.

[0324] Aspect 129 is a gas phase method for producing trifluoroiodomethane, the method comprising: providing a reactant stream comprising trifluoroacetyl iodide; and reacting the reactant stream at a reaction temperature of about 300° C. to about 400° C. for a contact time of about 2 seconds to about 50 seconds in the presence of a catalyst to produce a product stream comprising the trifluoroiodomethane, wherein the catalyst comprises activated carbon or about 0.3 wt % to about 0.7 wt % of palladium on a carrier.

[0325] Aspect 130 is a gas phase method for producing trifluoroiodomethane, the method comprising: providing a reactant stream comprising trifluoroacetyl iodide; and reacting the reactant stream at a reaction temperature of about 300° C. to about 350° C. for a contact time of about 3 seconds to about 30 seconds in the presence of a catalyst to produce a product stream comprising the trifluoroiodomethane, wherein the catalyst comprises activated carbon.

Claims

1. A gas phase method for producing trifluoroiodomethane, the method 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 at a first reaction temperature of 25° C. to 180° C. in the presence of a first catalyst to produce an intermediate product stream comprising trifluoroacetyl iodide; as well as The intermediate product stream is reacted at a second reaction temperature of 200°C to 600°C to produce a final product stream comprising the trifluoroiodomethane.

2. The method of claim 1, wherein in the providing step, the reactant stream comprises less than 500 ppm by weight of oxygen and the hydrogen iodide comprises less than 500 ppm by weight of water.

3. The method of claim 1, wherein in the step of reacting the reactant stream, the first catalyst comprises activated carbon, mesophase carbon, stainless steel, nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, alumina, platinum, palladium, metal carbide, non-metal carbide, or a combination thereof.

4. The method of claim 1, wherein in the step of reacting the intermediate product stream, the second catalyst comprises stainless steel, nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, alumina, silicon carbide, platinum, palladium, rhenium, activated carbon, mesophase carbon, or a combination thereof.

5. The process of claim 1 , wherein the organic compounds in the intermediate product stream comprise, based on GC area % of total organic compounds, 10% to 99% of trifluoroacetyl iodide, 1% to 90% of unreacted trifluoroacetyl halide, less than 0.010% of trifluoroiodomethane, and less than 15% of organic compounds other than trifluoroacetyl iodide, trifluoroacetyl halide, and trifluoroiodomethane.

6. The method according to claim 1, further comprising at least the following additional steps: separating unreacted trifluoroacetyl halide from the intermediate product stream; returning the separated trifluoroacetyl halide to the reaction stream; separating unreacted hydrogen iodide from the intermediate product stream; returning the unreacted hydrogen iodide to the reactant stream; separating unreacted trifluoroacetyl iodide from the final product stream; and The separated unreacted trifluoroacetyl iodide is returned to the intermediate product stream.

7. A gas phase process for producing trifluoroacetyl iodide (CFCOI), the process 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; and The reactant stream is reacted at a reaction temperature of 25°C to 180°C in the presence of a first catalyst to produce a product stream comprising trifluoroacetyl iodide.

8. The method of claim 7, wherein in the step of reacting the reactant stream, the catalyst comprises activated carbon, mesophase carbon, stainless steel, nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, alumina, platinum, palladium, metal carbide, non-metal carbide, or a combination thereof.

9. A gas phase method for producing trifluoroiodomethane, the method comprising: providing a reactant stream comprising hydrogen iodide and trifluoroacetyl chloride; reacting the reactant stream at a first reaction temperature of 25° C. to 120° C. and a pressure of atmospheric pressure to 300 psig in the presence of a first catalyst to produce an intermediate product stream comprising trifluoroacetyl iodide; as well as The intermediate product stream is reacted at a second reaction temperature of 200°C to 600°C to produce a final product stream comprising trifluoroiodomethane.

10. The method of claim 9, wherein in the step of reacting the reactant stream, the first catalyst comprises activated carbon, mesophase carbon, stainless steel, nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, alumina, platinum, palladium, metal carbide, non-metal carbide, or a combination thereof.

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