One-step process for producing trifluoroiodomethane from trifluoroacetyl halide, hydrogen, and iodine

Abstract

To provide a one-step process for producing trifluoroiodomethane (CF3I).SOLUTION: The present disclosure provides a process for producing trifluoroiodomethane (CF3I). The process includes providing vapor-phase reactants including trifluoroacetyl halide, hydrogen, and iodine, heating the vapor-phase reactants, and reacting the heated vapor-phase reactants in the presence of a catalyst including a transition metal to produce trifluoroiodomethane. The transition metal includes at least one selected from the group of nickel, platinum, and palladium.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present disclosure relates to a process for producing trifluoroiodomethane (CF3I). Specifically, the present disclosure relates to a catalyst and integrated process for producing trifluoroiodomethane. Regarding the process. [Background technology]

[0002] Trifluoroiodomethane (CF3I) is commercially used, for example, as a refrigerant or fire suppressant. Trifluoroiodomethane is a compound that is useful in applications. It is an environmentally acceptable compound with a low ozone depletion potential. can replace more environmentally harmful materials.

[0003] Methods for preparing trifluoroiodomethane are known, see, for example, U.S. Pat. No. 7,132, ,578 (Mukhopadhyay et al.) also reported the synthesis of methyltrifluoroacetyl chloride from trifluoroacetyl chloride. A catalytic one-step process for producing trifluoroiodomethane is disclosed. However, the source of iodine is iodine fluoride (IF). Iodine is relatively unstable. It is constant and decomposes to I2 and IF5 above 0°C. Iodine fluoride is also commercially available It may not be available in sufficient quantities.

[0004] In another example, U.S. Pat. No. 7,196,236 (Mukhopadhyay et al.) A reaction mixture containing an iodine source such as hydrogen iodide, at least a stoichiometric amount of oxygen, and the reactant CF3R is prepared. discloses a catalytic process for producing trifluoroiodomethane using a reactant where R is selected from the group consisting of -COOH, -COX, -CHO, -COOR2, and -SO2X. wherein R2 is an alkyl group and X is selected from the group consisting of chlorine, bromine, or iodine. The hydrogen iodide that can be produced by the reaction is obtained by reacting it with at least a stoichiometric amount of oxygen. It can be oxidized to produce water and iodine for economical recovery. Summary of the Invention [Problem to be solved by the invention]

[0005] Several other processes are known to convert trifluoroacetyl chloride to iodine in a gas phase reaction. There are references in the literature to making CF3I using hydrogen fluoride. The generation of CF3I from fluoroacetyl chloride and hydrogen iodide is The present disclosure provides a method for the preparation of trifluoroacetyl halides, hydrogen ions, and the like. and iodine are co-fed into a reactor in the presence of a catalyst to produce CF3I. Introduce a one-step process for

[0006] The present disclosure relates to hydrogen (H), elemental iodine (I), and trifluoroacetylhalogen. A process for producing trifluoroiodomethane from CF3C(O)X is provided.

[0007] In one embodiment, the present invention provides a method for producing trifluoroiodomethane (CF3I). The process comprises reacting a trifluoroacetyl halide, hydrogen, and iodide. providing a gas phase reactant containing uran; heating the gas phase reactant; and heating in the presence of a catalyst. and reacting the reacted vapor phase reactants to produce trifluoroiodomethane. The catalyst comprises a transition metal.

[0008] In another embodiment, the present invention provides a method for producing trifluoroiodomethane (CF3I). The process comprises the steps of: reacting trifluoroacetyl halide, hydrogen, and iodide; The reaction is carried out in the gas phase with trifluoroiodine at a temperature of about 200°C to about 600°C in the presence of a catalyst. methyl ether, unreacted trifluoroacetyl halide, unreacted hydrogen, unreacted iodine, and and hydrogen iodide. The catalyst comprises a transition metal. The process removes unreacted iodine from the product stream by cooling the product stream and condensing the iodine from the vapor phase. and recovering the condensed iodine in the reaction stage. and

[0009] These and other features of the present disclosure, and the manner in which they are achieved, will become more apparent and will be described hereinafter. This will be better understood by reference to the description of the embodiments of DETAILED DESCRIPTION OF THE INVENTION

[0010] The present disclosure provides a method for the synthesis of trifluoroacetyl halides (CF3C( O)X), hydrogen (H), and iodine (I) to produce trifluoroiodomethane (CF3I The present invention provides a one-step process for producing a hydroxybenzoate of about 200 ppm in the presence of a transition metal catalyst. By reacting at temperatures between 100°C and approximately 600°C, trifluoromethane was obtained from these readily available reactants. It has been found that the reaction can provide an efficient production of difluoroiodomethane. Recovery further improves efficiency.

[0011] As disclosed herein, trifluoroiodomethane is a reactant trifluoroa Cetyl halide, hydrogen (H2), and iodine (I2) react at temperatures between approximately 200°C and approximately 600°C. All reactions are produced in a one-step process where the catalyst is co-fed to the reactor. The product is anhydrous. Any water in the reaction favors secondary reaction pathways, and trifluoromethane reactants because they can form undesirable by-products such as fluoromethane (CF3H4). It is preferable to use as little water as possible.

[0012] Trifluoroacetyl halides are substantially free of water. Any water in the cetyl halide is about 500 parts per million (ppm) by weight, about 30 0ppm, approx. 200ppm, approx. 100ppm, approx. 50ppm, approx. 30ppm, approx. 20ppm m, or less than about 10 ppm, or any value defined between any two of the preceding values. Preferably, any water in the trifluoroacetyl halide is in an amount less than about 1 More preferably, any of the trifluoroacetyl halides is present in an amount of less than 0.00 ppm by weight. The optional water is in an amount of less than about 30 ppm by weight. Any water in the ride is in an amount less than about 10 ppm by weight.

[0013] Iodine is substantially free of water, i.e., any water in iodine is less than about 500% by weight. ppm, approx. 300ppm, approx. 200ppm, approx. 100ppm, approx. 50ppm, approx. 30pp m, about 20 ppm, or less than about 10 ppm, or a value between any two of the foregoing values. Preferably, any water in the iodine is less than about 100 wt. p More preferably, any water in the iodine is less than about 30 ppm by weight. Most preferably, any water in the iodine is in an amount less than about 10 ppm by weight.

[0014] Hydrogen is substantially free of water, i.e., any water in the hydrogen is less than about 500 parts per million by weight. m, about 300ppm, about 200ppm, about 100ppm, about 50ppm, about 30ppm, Defined as about 20 ppm, or less than about 10 ppm, or between any two of the foregoing values. Preferably, any water in the hydrogen is less than about 100 ppm by weight. More preferably, any water in the hydrogen is in an amount less than about 30 ppm by weight. Most preferably, any water in the hydrogen is in an amount less than about 10 ppm by weight.

[0015] Trifluoroacetyl halide is trifluoroacetyl fluoride (CF3C(O )F), trifluoroacetyl chloride (CF3C(O)Cl), trifluoroacetyl bromide (CF3C(O)Br), and any combination thereof. Preferably, the trifluoroacetyl halide is trifluoroacetyl chloride. More preferably, the trifluoroacetyl halide is trifluoroacetyl chloride. Most preferably, the trifluoroacetyl halide consists essentially of trifluoroacetyl halide. It consists of acetyl chloride.

[0016] For example, trifluoroacetyl chloride is a halocarbon product. s Corporation, Peachtree Corners, Georgia? or Solvay SA, Brussels, Belgium. Hydrogen is readily available in quantities suitable for use in gasoline and diesel engines. Solid iodine is commercially available from SQM, Santiago, Chile. e, or Kanto Natural Gas Development Co.,Lt. d, Chiba, Japan.

[0017] The reactants are mixed in a ratio of 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, or as low as about 1:1 or 1.1:1, 1.2:1, 1.5:1, 2:1, 2.5:1, 3:1, 4:1, or as high as 5:1, or any range defined between any two of the preceding values. Within this range, for example, about 0.1:1 to about 5:1, about 0.2:1 to about 4:1, or about 0.3:1 to about 3 :1, about 0.4:1 to about 2.5:1, about 0.5:1 to about 2:1, about 0.5:1 to about 1.5 :1, about 0.7:1 to about 1.2:1, about 0.8:1 to about 1.1:1, or about 0.9:1 to A low hydrogen to iodine molar ratio of about 1:1 may be provided for the reaction. The molar ratio of hydrogen to iodine is about 0.1:1 to about 1:1. The molar ratio of hydrogen to iodine is about 0.3:1 to about 0.8:1. Most preferably, the molar ratio of hydrogen to iodine is When the molar ratio of hydrogen to iodine is less than 1, the molar ratio is from about 0.5:1 to about 0.7:1. It has been found that this provides a significant improvement in yield over the case where the hydroxyl group is substituted with hydroxyl group. However, when the molar ratio of hydrogen to iodine is less than 1, Which competing side reactions form undesired by-products from trifluoroacetyl halides? It is thought that there is very little hydrogen available for use.

[0018] The reactants were about 0.002:1, about 0.004:1, about 0.006:1, about 0.008 :1, approximately 0.01:1, approximately 0.02:1, approximately 0.03:1, and as low as approximately 0.04:1. or about 0.05:1, about 0.07:1, about 0.09:1, about 0.1:1, about 0.2:1, As high as about 0.3:1, about 0.4:1, about 0.5:1, or about 1:1, or any of the foregoing values Within any range defined between any two of the above, for example, from about 0.002:1 to about 1: 1, about 0.004:1 to about 0.5:1, about 0.006:1 to about 0.4:1, or about 0.0 For the reaction, the molar ratio of hydrogen to trifluoroacetyl halide is 1:1 to 0.1:1. Preferably, the molar ratio of hydrogen to iodine is from about 0.01:1 to about 0.05: It is 1.

[0019] The reactants react in the presence of a catalyst contained within the reactor to form trimethylsilyl methyl ether according to Equation 1 below: Fluoroiodomethane and its reaction by-products carbon monoxide (CO) and hydrogen halides (HX ) to produce a product stream comprising: Equation 1:2CF3C(O)X+H2+I2→2CF3I+2HX+2CO where X can be a fluoride, a salt, or a mixture thereof depending on the trifluoroacetyl halide reactant selected. Therefore, hydrogen halides include hydrogen fluoride (HF), hydrogen chloride, and Hydrogen fluoride (HCl) and / or hydrogen fluoride (HBr).

[0020] In the reactor, hydrogen and iodine react to form hydrogen iodide (HI) in situ, which Reacts almost immediately with trifluoroacetyl halides to form trifluoroiodomethane Competing side reactions, such as trifluoromethane (CF3H ), iodomethane (CH3I), and trifluoroacetyl iodide (TFAI). The reactor may be a fixed-bed tubular reactor or other reactor containing tubes containing a catalyst. The reactor may be a hot tube reactor. The tubes may be made of stainless steel, nickel, and / or nickel alloys, e.g. For example, nickel-molybdenum alloy, nickel-chromium-molybdenum alloy, or nickel The catalyst may be made of a metal such as a copper alloy. By heating the tube reactor, the catalyst is also heated. Alternatively, the reactor may be any type of packed reactor.

[0021] The reaction is carried out substantially free of oxygen (O2). That is, any oxygen in the reaction is Approximately 500 parts per million by weight, approximately 300 ppm, approximately 200 ppm, approximately 100 ppm , about 50 ppm, about 30 ppm, about 20 ppm, about 10 ppm, about 5 ppm, about 3 ppm , about 2 ppm, or less than about 1 ppm, or between any two of the foregoing values. Preferably, any oxygen in the reaction is less than about 100 wt pp More preferably, any oxygen in the reaction is present in an amount of less than about 10 ppm by weight. Most preferably, any oxygen in the reaction is in an amount less than about 3 ppm by weight. At least one of the hydrogen iodide is reacted to form trifluoroiodomethane. It can oxidize the iodine moiety to form iodine and water, thereby reducing the efficiency of the process. Therefore, it is preferable to keep the amount of oxygen in the reaction as low as possible.

[0022] The catalyst comprises a transition metal. Preferably, the transition metal is a non-noble transition metal such as nickel, copper, or the like. Baltic, or iron, or precious metals; transition metals; rhodium, iridium, platinum, palladium, or other More preferably, the transition metal is nickel, platinum, palladium, or any combination thereof. Most preferably, the transition metal consists essentially of palladium, palladium, or a combination thereof. It basically comes from Um.

[0023] The catalyst comprises a support for the fibrous metal. Preferably, the support is carbon, aluminum oxide, or the like. Al2O3, silica gel (SiO2), silicon carbide (SiC), or a combination thereof Most preferably, the support consists essentially of aluminum oxide.

[0024] The transition metal on the surface of the catalyst as a percentage of the total combined weight of the transition metal and support. The amount of transition metal may be about 0.01 weight percent (wt%), about 0.02 wt%, about 0.1 wt%, %, about 0.3% by weight, about 0.5% by weight, about 0.7% by weight, about 1% by weight, about 2% by weight, or As little as about 4% by weight, or at most about 6%, about 8%, about 10%, about 15% by weight about 20% by weight, about 21% by weight, about 25% by weight, about 30% by weight, or about 40% by weight or within any range defined between any two of the preceding values, e.g., Approximately 0.01% by weight ~ approximately 40% by weight, approximately 0.02% by weight ~ approximately 30% by weight, approximately 0.1% by weight ~ About 25% by weight, about 0.3% to about 20% by weight, about 0.5% to about 15% by weight, about 0. 7% to about 10% by weight, about 1% to about 8% by weight, about 2% to about 6% by weight, about 1% by weight % to about 4% by weight, or about 0.3% to about 0.7% by weight, etc. The amount of non-noble transition metal on the surface of the catalyst is about 5% by weight to about 35% by weight. In general, the amount of non-noble transition metal on the surface of the catalyst is about 10% by weight to about 30% by weight. Preferably, the amount of non-noble transition metal on the surface of the catalyst is about 20% to about 30% by weight. Preferably, the amount of the noble transition metal on the surface of the catalyst is about 0.1% by weight to about 5% by weight. More preferably, the amount of the noble transition metal on the surface of the catalyst is from about 0.3 wt % to about 1 wt %. Most preferably, the amount of noble transition metal on the surface of the catalyst is about 0.3 wt. % to It is about 0.7% by weight.

[0025] The reaction is carried out at about 0.1 seconds, 1 second, about 2 seconds, about 4 seconds, about 6 seconds, about 8 seconds, about 10 seconds, about 15 seconds. seconds, about 20 seconds, about 25 seconds, or as short as about 30 seconds, or about 40 seconds, about 50 seconds, or about 60 seconds , about 70 seconds, about 80 seconds, about 100 seconds, about 120 seconds, or about 1,200 seconds, or Within any range defined between any two of the preceding values, for example, from about 0.1 seconds to about 1,200 seconds, about 2 seconds to about 120 seconds, about 4 seconds to about 100 seconds, about 6 seconds to about 80 seconds, about 8 seconds to Approximately 70 seconds, approximately 10 seconds to approximately 60 seconds, approximately 15 seconds to approximately 50 seconds, approximately 20 seconds to approximately 40 seconds, approximately 20 seconds to For a contact time of about 30 seconds, about 10 seconds to about 20 seconds, or about 100 seconds to about 120 seconds, the catalyst Preferably, the reactants are contacted with the catalyst for a contact time of from about 1 second to about 100 seconds. More preferably, the reactants are in contact with the catalyst for a contact time of from about 2 seconds to about 50 seconds. Most preferably, the reactants are contacted with for a contact time of from about 10 seconds to about 30 seconds. In contact with the catalyst.

[0026] The reaction proceeds at temperatures of about 200°C, about 250°C, about 300°C, about 320°C, about 330°C, and about 340°C. From a temperature as low as about 350°C, or about 360°C, about 370°C, about 380°C, about 39 0°C, about 400°C, 500°C, or as high as about 600°C, or any of the aforementioned values. Within any range defined between any two of the above, for example, about 200°C to about 600°C, about 2 50℃~approx. 500℃, approx. 300℃~approx. 400℃, approx. 320℃~approx. 390℃, approx. 340℃~ The reaction is preferably carried out at about 380°C, about 350°C to about 370°C, or about 340°C to about 360°C. Preferably, the reactants are heated to a temperature of about 300°C to about 400°C. The reactants are heated to a temperature of about 320°C to about 360°C. Most preferably, the reactants are heated to a temperature of about 340°C to about 360°C. It is heated to a temperature of about 360°C.

[0027] The pressure is not critical. Convenient operating pressures are from about 10 kPa to about 4,000 kPa, preferably The pressure is preferably in the range of about 100 kPa to about 350 kPa.

[0028] The composition of organic compounds in the product stream leaving the reactor was determined by gas chromatography (GC). and can be measured by gas chromatography-mass spectrometry (GC-MS). The graphical areas provided by the GC analysis of each organic compound are combined to determine the active compounds in the product stream. The GC area of ​​all organic compounds relative to each of the organic compounds as a measure of their relative concentration. The percentage (GC region %) can be provided.

[0029] The concentration of trifluoroiodomethane in the product stream exiting the reactor is determined by the halogenated trifluoroiodomethane. The GC area percentage of all organic compounds not containing oroacetyl was approximately 10%, 15%, and 2%. 0%, about 25%, about 30%, about 35%, about 40%, about 45%, about 50%, about 55% or about It may be as low as 60%, or about 65%, about 70%, about 75%, about 80%, about 85%, It may be as high as about 90%, about 95%, about or 99%, or any of the aforementioned values. Within any range defined between the two, for example, about 10% to about 99%, about 20% to about 95% , about 30% to about 90%, about 40% to about 85%, about 45% to about 80%, about 50% to about 75% , about 55% to about 70%, about 60% to about 65%, about 90% to about 99%, or about 95% to about 9 9%, etc. Preferably, the concentration of trifluoroiodomethane in the product stream is about More preferably, the concentration of trifluoroiodomethane in the product stream is from 30% to about 99%. The concentration is from about 70% to about 99%. Most preferably, the trifluoroiodomethane concentration in the product stream is The concentration of the tan is about 90% to about 99%.

[0030] The product stream is directed from the reactor to one or more iodine removal vessels where the product stream is cooled. The unreacted iodine is condensed and at least a portion of the iodine is removed from the product stream. The product stream is recycled as a product at a temperature lower than the boiling point of iodine but higher than the melting point of iodine. Alternatively, the solution may be cooled to a higher temperature to condense the iodine in liquid form. In addition, the product stream exiting the reactor is subjected to iodine extraction to recover the iodine in solid form. The product stream may be cooled to a temperature below the melting point. The product stream may be separated from the iodine removal vessel by one or more additional iodine removal vessels. It may proceed to an iodine removal tank to remove additional unreacted iodine for recycle.

[0031] The product stream is directed from one or more iodine removal tanks to a heavy distillation column to produce methyl iodide (C High-boiling by-products such as trifluoroacetyl iodide (TFAI) and trifluoroacetyl iodide (H3I) were removed by trifluoroacetyl iodide. Fluoroiodomethane (CF3I), unreacted trifluoroacetyl halide (CF3C( O)X), as well as trifluoromethane (CF3H), hydrohalic acid (HX), iodide It can be separated from other by-products such as hydrogen (HI) and carbon monoxide (CO). From a heavy distillation column containing CF3I, CF3C(O)X, CF3H, HX, HI, H2, and CO These overhead streams are separated into CF3H, HX, CO, and H2 from low boiling compounds. Directed to a light distillation column to separate high boiling compounds such as 3C(O)X, HI and CF3I The overhead stream from the light distillation column containing CF3H, HX, CO, and H2 can be The high boiling point compounds can be sent to a scrubber to remove HX and then to a thermal oxidizer. The products CF3C(O)X, HI, and CF3I are sent downstream of the light distillation column to one or more distillation columns. CF3C(O)X and HI can be separated from CF3I. The 3C(O)X and HI may be recycled to the reactor. The separated CF3I is The F3I product may be directed to one or more product distillation columns to separate the CF3I product. can be collected from the overhead stream of the final product distillation column. Iodine, CF3 Recycling of C(O)X and HI provides an efficient process for producing CF3I. Obtained.

[0032] The diagram shows an integrated process 10 for producing trifluoroiodomethane. As shown in the figure, the process 10 involves the reaction of solid iodine 12, hydrogen 14, and thiazolinone. Trifluoroacetyl halide, trifluoroacetyl chloride (TFAC) 16 materials Solid iodine 12 may be added to the solid storage tank 18 continuously or intermittently. A constant flow of solid iodine is delivered by a solid transport system (not shown) to a solid storage tank. From 18, the solid iodine is delivered to an iodine liquefaction unit 20, where the solid iodine is liquefied while still above its melting point. , heated below its boiling point to maintain the level of liquid iodine in the iodine liquefaction unit 20. Liquid iodine flows from the iodine liquefaction device 20 to the iodine vaporization device 22. 20 may be pressurized with an inert gas to drive the flow of liquid iodine. The gas may be, for example, nitrogen, argon, or helium, or a mixture thereof. The flow rate of the liquid iodine may be controlled by a liquid flow controller 24. In the iodine vaporizer 22, the iodine is heated above its boiling point to form a stream of iodine vapor. .

[0033] The hydrogen 14 is provided to a hydrogen preheater 26 where the hydrogen 14 is heated to a selected reaction temperature. The flow rate of the heated hydrogen may be controlled by a gas flow controller 28.

[0034] The TFAC 16 is connected to a TFAC preheater 30 where the TFAC is heated to a selected reaction temperature. The flow rate of the heated TFAC may be controlled by a gas flow controller 32. The heated hydrogen stream and the heated TFAC stream may be mixed in a mixing valve 34. The iodine vapor stream can then be combined with another stream of iodine vapor in a mixing valve 36. Alternatively, a flow of heated hydrogen, a flow of heated TFAC, and a flow of iodine may be combined in a single mixing valve. Iodine vapor, hydrogen and TFAC heating The resulting mixture is provided to reactor 38.

[0035] The heated mixture of iodine vapor, hydrogen, and TFAC is heated by the catalyst contained within reactor 38. The catalyst 40 reacts in the presence of a catalyst 40 to produce a crude product stream. The crude product stream may be, for example, trifluoroiodomethane, unreacted water, unreacted iodine, unreacted TFAC, and HI, CO, CF3H, TFAI, HCl, and and CH3I.

[0036] The crude product stream is provided to the iodine removal vessel 44. The crude product stream is The mixture is cooled to a temperature below the boiling point of iodine to condense at least a portion of the iodine and then coarsely The iodine collected in iodine removal vessel 44 is separated from the product stream. 6. Iodine recycle stream 46 may be passed through iodine liquefaction unit 20 to recover iodine. will be provided to.

[0037] The crude product stream is further cooled in iodine removal vessel 44 to a temperature below the melting point of iodine. iodine from the crude product stream and remove at least part of the iodine in iodine removal vessel 44. A portion of the iodine can be deposited as a solid. Then, the iodine removal tank 44 is sampled offline. Alternatively, the iodine may be heated to liquefy the iodine into the iodine recycle stream 46.

[0038] Although a single iodine removal vessel 44 is shown, the iodine removal vessels 44 may be operated in a parallel configuration. two or more iodine removal tanks 44 operating in a series configuration; and It is understood that the iodine removal bath 44 may include any combination thereof. To provide continuous operation while collecting the iodine, a separate trough was used for the removal of solid iodine. Iodine to ensure that at least one train is operating while the other is offline It is also understood that multiple trains of removal vessels 44 may be included.

[0039] The crude product stream is provided from iodine removal vessel 44 to a heavy distillation column 48. Heavy distillation column 48 comprises: Heavy organic substances such as CH3I and TFAI are separated from light organic substances such as CF3I and unreacted TFAC. and from by-products such as HI, CO, CF3H, and HCl. The bottoms stream 50 containing organic heavies obtained from the heavy distillation column 48 may be provided to a vessel. The organic heavy materials in the vessel may be disposed of to recover the components for further use or sale. It may be well or further distilled.

[0040] 48 from a heavy distillation column containing CF3I, TFAC, CF3H, HCl, HI, H2 and CO The overhead stream 52 containing these organic lights is directed to a lights distillation column 54 to produce CF3H, From low boiling point compounds such as HCl, CO, and H2 to TFAC, HI, and CF3I, Separating high boiling compounds. Light distillation column 54 contains CF3H, HCl, CO, and H2. The bar head stream 56 is provided to a scrubber (not shown) for removal of HCl and then The CF3H, CO, and H2 may be provided to a thermal oxidizer (not shown) for oxidation.

[0041] The bottoms stream 58 containing CF3I, TFAC, and HI from the light distillation column 54 is recycled. The recycle column 60 separates CF3I from TFAC and HI. The overhead stream 62 of the recycle column 60 containing TFAC and HI can be configured as follows: , forming a TFAC / HI recycle stream. The TFAC / HI recycle stream 62 is C and HI are provided to the TFAC preheater 30 for recycling. Although column 60 is shown, recycle column 60 may be used in series to achieve the desired separation efficiency. The recycle tower may include two or more recycle towers operating in parallel, in parallel, or any combination thereof. It is understood that:

[0042] A bottoms stream 64 containing CF3I and traces of organic light and heavy materials from the recycle column 60. is provided to a first product column 66. The first product column 66 separates trace organic light materials to C The first one, which contains organic light materials and some CF3I, is configured to separate F3I. The overhead stream 68 of the product column 66 is recycled to recover additional CF3I. a bottoms stream 70 comprising CF3I, and The organic heavy materials from the first product column 66 are provided to the second product column 72. Product CF3I can be collected from the bottoms stream 74 of the second product column 72. Bottoms stream 76 containing CF3I and organic heavies from second product column 72 is used to recover additional CF3I. The bottoms stream 58 may be provided to a recycle column 60 for collection.

[0043] Although the present invention has been described with respect to exemplary designs, the present invention is not limited to the spirit and scope of this disclosure. Furthermore, this application is not intended to be a substitute for the disclosure of the present invention. It is intended to cover such departures from the present disclosure as come within known or customary practice in the art. It has been done.

[0044] As used herein, "any value defined between any two of the preceding values" means any value between two of the preceding values. The phrase "within the range" means that the values ​​may be in a lower part of the list or in a higher part of the list. Any range, whether in For example, a pair of values ​​may be selected from two lower values, two The value may be selected from a higher value, or a lower value and a higher value. [Brief explanation of the drawings]

[0045] [Figure 1] FIG. 1 is a process flow diagram illustrating an integrated process 10 for producing trifluoroiodomethane. [Example]

[0046] Examples 1-4: Trifluoroacetyl chloride (TFAC), hydrogen, and elemental iodide Production of CF3I from elements In the following examples, the trifluoromethyl iodine (TFAC) from TFAC, hydrogen, and iodine according to Scheme 1 above is synthesized. The production of iodomethane has been demonstrated. An el600 tube was used as the reactor, and Johnson Matthey 0.1 wt% P % Pd / Al2O3 catalyst or BASF's 0.5 wt% Pd / Al2O3 catalyst for 11 The reactor was preheated to 350°C. A certain amount of TFAC was added as shown in the table below. and H2 were co-fed to a TFAC / H2 preheater, and then 1000 grams of solid iodine was added first. The temperature of the I2 vaporizer was controlled at 150 to 165°C. Next, a mixture of I2 vapor, TFAC vapor, and H2 vapor was heated in a catalytic atmosphere. The reactor effluent was fed into a heated fixed-bed tubular reactor charged with a catalyst. 2 collector to capture the unreacted I2 in solid form and then into a deionized water scrubber. It was fed to capture unreacted TFAC and the HCl and HI produced during the reaction.

[0047] Periodically, samples were taken from the wastewater of the deionized water scrubber and the organic compounds in the samples were analyzed. The composition of the substance was measured by gas chromatography (GC). The graph regions provided are combined to generate the GC region of all organic compounds for each of the organic compounds. The region percentage (GC region %) was provided.

[0048] At the end of the reaction run time, stop the system and measure the weight loss of the iodine vaporizer and the iodine The weight increase of the removal tank was measured to determine the iodine supply rate. The average molar ratio of H2:I2 fed to the reactor was determined by comparing the feed rates. The residence time was calculated based on the combined feed rates of hydrogen, iodine, and TFAC. .

[0049] The results for each example are shown in Table 1. For each example, Table 1 lists the aluminum oxide used. The amount of palladium on the catalyst, the TFAC feed rate, the H2 feed rate, and the average H2 vs. I2 molar feed ratio, average molar feed ratio of TFAC to HI, residence time, and CF3I at the end of the run; The GC area percentages of CF3H and CH3I are shown. Examples 1, 3, and 4 were run for 24 hours. Example 2 was run for 20 hours. As shown in Table 1, the average molar feed ratio of H2 to I2 was In embodiments where the average molar feed ratio of H2 to TFAC is less than 1:1 and less than 0.05:1, CF The selectivity for 3I was significantly improved. In addition, the average molar feed ratio of H2 to I2 was less than 1:1. When the average molar feed ratio of H2 to TFAC is less than 0.05:1, the amount of palladium on the support More appears to improve the selectivity of CF3I. [Table 1]

[0050] Aspects Aspect 1 is a process for producing trifluoroiodomethane (CF3I) This process involves the use of gas phase reactants containing trifluoroacetyl halide, hydrogen, and iodine. and heating the gas phase reactants; and reacting the heated gas phase reactants in the presence of a catalyst. and reacting the catalyst to produce trifluoroiodomethane, the catalyst comprising a transition metal. This includes generating.

[0051] Embodiment 2 is the process of embodiment 1, wherein the trifluoroacetyl halide is about 500 times as heavy as the trifluoroacetyl halide. Contains less than ppm of water.

[0052] Embodiment 3 is the process of embodiment 1, wherein the trifluoroacetyl halide is about 100 times Contains less than ppm of water.

[0053] Embodiment 4 is the process of embodiment 1, wherein the trifluoroacetyl halide is about 30 wt. Contains less than ppm of water.

[0054] Embodiment 5 is the process of embodiment 1, wherein the trifluoroacetyl halide is about 10 wt. Contains less than ppm of water.

[0055] Aspect 6 is the process of any of Aspects 1-5, wherein the hydrogen is less than about 500 ppm by weight. Contains full of water.

[0056] Aspect 7 is the process of any of Aspects 1-5, wherein the hydrogen is less than about 100 ppm by weight. Contains full of water.

[0057] Example 8 is the process of any of Examples 1-5, wherein the hydrogen is less than about 30 ppm by weight. Contains water.

[0058] Aspect 9 is the process of any of Aspects 1-5, wherein the hydrogen is less than about 10 ppm by weight. Contains water.

[0059] Example 10 is the process of any of Examples 1-9, wherein the iodine is about 500 ppbw Contains less than m of water.

[0060] Example 11 is the process of any of Examples 1-9, wherein the iodine is about 100 ppbw Contains less than m of water.

[0061] Example 12 is the process of any of Examples 1-9, wherein the iodine is about 30 ppm by weight. Contains less than 100% water.

[0062] Example 13 is the process of any of Examples 1-9, wherein the iodine is about 10 ppm by weight. Contains less than 100% water.

[0063] Aspect 14 is the process of any one of Aspects 1 to 13, wherein the providing step The molar ratio of hydrogen to iodine is about 0.1:1 to about 5:1.

[0064] Aspect 15 is the process of any one of Aspects 1 to 13, wherein the providing step The molar ratio of hydrogen to iodine is about 0.1:1 to about 1:1.

[0065] Aspect 16 is the process of any one of Aspects 1 to 13, wherein the providing step The molar ratio of hydrogen to iodine is about 0.3:1 to about 0.8:1.

[0066] Aspect 17 is the process of any one of Aspects 1 to 13, wherein the providing step The molar ratio of hydrogen to iodine is about 0.5:1 to about 0.7:1.

[0067]

[0023] Aspect 18 is the process of any one of Aspects 1 to 17, wherein the providing step The molar ratio of hydrogen to trifluoroacetyl halide is about 0.002:1 to about 1:1. .

[0068] Aspect 19 is the process of any one of Aspects 1 to 17, wherein the providing step The molar ratio of hydrogen to trifluoroacetyl halide is about 0.01:1 to about 0.05:1. be.

[0069] Aspect 20 is the process of any one of Aspects 1 to 19, wherein the providing step The gas phase reactants contain less than about 500 ppm by weight of oxygen.

[0070] Aspect 21 is the process of any one of Aspects 1 to 19, wherein the providing step The gas phase reactants contain less than about 100 ppm by weight of oxygen.

[0071] Aspect 22 is the process of any one of Aspects 1 to 19, wherein the providing step The gas phase reactants contain less than about 10 ppm by weight of oxygen.

[0072] Aspect 23 is the process of any one of Aspects 1 to 19, wherein the providing step The gas phase reactants contain less than about 3 ppm by weight of oxygen.

[0073] Example 24 is the process of any of Examples 1 to 23, wherein the transition metal is nickel, copper, or the like. At least one metal selected from the group consisting of ballast, iron, rhodium, iridium, platinum, and palladium Also includes one.

[0074] Example 25 is the process of any of Examples 1-23, wherein the transition metal is nickel, platinum, or the like. It consists essentially of gold, palladium, or a combination thereof.

[0075] Example 26 is the process of any of Examples 1-23, wherein the transition metal is nickel, platinum, or the like. It consists essentially of gold, palladium, or a combination thereof.

[0076] Example 27 is the process of any of Examples 1-23, wherein the transition metal is selected from the group consisting of palladium and arsenic. It becomes basic.

[0077] Example 28 is the process of any of Examples 1-27, wherein the catalyst is aluminum oxide. At least one selected from the group consisting of a support, a carbon support, a silica gel support, and a silicon carbide support. The carrier further comprises one of the following:

[0078] Example 29 is the process of any of Examples 1-27, wherein the catalyst is aluminum oxide. Further included is a carrier consisting essentially of a carrier.

[0079] Example 30 is the process of any of Examples 28 or 29, further comprising: The transition metal is about 0.01% by weight to about 40% by weight of the total weight of the transition metal and the support.

[0080] Example 31 is the process of Example 30, wherein the transition metal is nickel, cobalt, iron, or bromine. at least one selected from the group consisting of tungsten, iridium, platinum, palladium, and combinations thereof; and the amount of transition metal on the surface of the catalyst is about 5 times the total weight of the transition metal and the support. % to about 35% by weight.

[0081] Example 32 is the process of Example 30, wherein the transition metal is nickel, cobalt, iron, or bromine. at least one selected from the group consisting of tungsten, iridium, platinum, palladium, and combinations thereof; and the amount of transition metal on the surface of the catalyst is about 10% of the total weight of the transition metal and the support. % by weight to about 30% by weight.

[0082] Example 33 is the process of Example 30, wherein the transition metal is nickel, cobalt, iron, or bromine. at least one selected from the group consisting of tungsten, iridium, platinum, palladium, and combinations thereof; and the amount of transition metal on the surface of the catalyst is about 20% of the total weight of the transition metal and the support. % by weight to about 30% by weight.

[0083] Example 34 is the process of Example 30, wherein the transition metal comprises nickel and the support is an acid. The nickel comprises about 21 parts by weight of the total weight of the nickel and aluminum oxide. % by volume.

[0084] Example 35 is the process of Example 30, wherein the transition metal is rhodium, iridium, platinum. , palladium, or a combination thereof, The amount of the transition metal on the surface is about 0.1% by weight to about 5% by weight of the total weight of the transition metal and the support. do.

[0085] Example 36 is the process of Example 30, wherein the transition metal is rhodium, iridium, platinum, or , palladium, or a combination thereof, The amount of the transition metal on the surface is about 0.3% by weight to about 1% by weight of the total weight of the transition metal and the support. do.

[0086] Example 37 is the process of Example 30, wherein the transition metal is rhodium, iridium, platinum. , palladium, or a combination thereof; The amount of transition metal on the surface of the catalyst is about 0.3% by weight to about 1% by weight of the total weight of the transition metal and the support. is.

[0087] Example 38 is the process of Example 30, wherein the transition metal comprises palladium and the support is The palladium content is about 100% by weight of the total of the palladium and aluminum oxide. It is 0.5% by weight.

[0088] Example 39 is the process of any of Examples 1-38, wherein the vapor phase reactants are heated to about 200° C. It is heated to a temperature of about 600°C.

[0089] Example 40 is the process of any of Examples 1-38, wherein the vapor phase reactants are heated to about 300° C. It is heated to a temperature of about 400°C.

[0090] Example 41 is the process of any of Examples 1-38, wherein the vapor-phase reactants are heated to about 320° C. It is heated to a temperature of about 360°C.

[0091] Example 42 is the process of any of Examples 1-38, wherein the vapor phase reactants are heated to about 340° C. It is heated to a temperature of about 360°C.

[0092] Aspect 43 is the process of any one of Aspects 1 to 42, wherein the reacting step comprises The contact time of the reactants with the catalyst is from about 0.1 seconds to about 1,200 seconds.

[0093] Example 44 is the process of any of Examples 1 to 42, wherein the reacting step comprises The contact time of the reactants with the catalyst is from about 1 second to about 100 seconds.

[0094] Embodiment 45 is the process of any of Embodiments 1 to 42, wherein in the reacting step, The contact time of the reactants with the catalyst is from about 2 seconds to about 50 seconds.

[0095] Aspect 46 is the process of any of Aspects 1 to 42, wherein the reacting step comprises The contact time of the reactants with the catalyst is from about 10 seconds to about 30 seconds.

[0096] Example 47 is the process of any of Examples 1-46, wherein the process comprises removing unreacted iodide. Separating the iodine from trifluoroiodomethane and providing unreacted iodine. and returning the data to the group.

[0097] Example 48 is the process of any of Examples 1-47, wherein the process is a continuous process. is.

[0098] Example 49 is the process of any of Examples 1 to 47, wherein the process is a batch process. It is.

[0099] Example 51 is the process of any of Examples 1 to 49, wherein the trifluoroacetyl halides The amides are trifluoroacetyl fluoride, trifluoroacetyl chloride, trifluoroacetyl diacetyl bromide, and any combination thereof.

[0100] Example 52 is the process of any of Examples 1 to 49, wherein the trifluoroacetyl halides The amides include trifluoroacetyl chloride.

[0101] Example 53 is the process of any of Examples 1 to 49, wherein the trifluoroacetyl halides The amide consists essentially of trifluoroacetyl chloride.

[0102] Example 54 is the process of any of Examples 1 to 49, wherein the trifluoroacetyl halides The amide consists essentially of trifluoroacetyl chloride.

[0103] Embodiment 55 is a process for producing trifluoroiodomethane (CF3I), The process involves the following steps: trifluoroacetyl halide, hydrogen, and iodine are reacted in the vapor phase. and reacting the resulting mixture with trifluoroiodomethane at a temperature of about 200°C to about 600°C in the presence of a catalyst. Unreacted trifluoroacetyl halide, unreacted hydrogen, unreacted iodine, and iodine water producing a product stream comprising a catalyst, the catalyst comprising a transition metal; Removing unreacted iodine from the product stream by cooling the product stream to condense the iodine from the vapor phase and recycling the condensed iodine to the reaction step. Includes and.

[0104] Embodiment 56 is the process of embodiment 55, wherein the trifluoroacetyl halide is from about 50 Contains less than 0 ppm water by weight.

[0105] Embodiment 57 is the process of embodiment 55, wherein the trifluoroacetyl halide is from about 10 Contains less than 0 ppm water by weight.

[0106] Embodiment 58 is the process of embodiment 55, wherein the trifluoroacetyl halide is from about 30 Contains less than ppm water by weight.

[0107] Embodiment 59 is the process of embodiment 55, wherein the trifluoroacetyl halide is from about 10 Contains less than ppm water by weight.

[0108] Embodiment 60 is the process of any of embodiments 55-59, wherein the hydrogen is about 500 wt. p Contains less than pm of water.

[0109] Example 61 is the process of any of Examples 55-59, wherein the hydrogen is about 100 wt. p Contains less than pm of water.

[0110] Example 62 is the process of any of Examples 55-59, wherein the hydrogen is about 30 wt pp Contains less than m of water.

[0111] Example 63 is the process of any of Examples 55-59, wherein the hydrogen is about 10 wt pp Contains less than m of water.

[0112] Example 64 is the process of any of Examples 55-63, wherein the iodine is about 500 wt. Contains less than ppm of water.

[0113] Example 65 is the process of any of Examples 55-63, wherein the iodine is about 100 wt. Contains less than ppm of water.

[0114] Example 66 is the process of any of Examples 55-63, wherein the iodine is about 30 parts by weight. Contains less than pm of water.

[0115] Example 67 is the process of any of Examples 55-63, wherein the iodine is about 10 parts by weight Contains less than pm of water.

[0116] Example 68 is the process of any of Examples 55-67, wherein the molar ratio of hydrogen to iodine is , about 0.1:1 to about 5:1.

[0117] Example 69 is the process of any of Examples 55-67, wherein the molar ratio of hydrogen to iodine is , about 0.1:1 to about 1:1.

[0118] Example 70 is the process of any of Examples 55-67, wherein the molar ratio of hydrogen to iodine is , about 0.3:1 to about 0.8:1.

[0119] Example 71 is the process of any of Examples 55-67, wherein the molar ratio of hydrogen to iodine is , about 0.5:1 to about 0.7:1.

[0120] Example 72 is the process of any of Examples 55 to 71, wherein hydrogen and trifluoroacetone are The molar ratio of methyl halide is about 0.002:1 to about 1:1.

[0121] Example 73 is the process of any of Examples 55 to 71, wherein hydrogen and trifluoroacetone are The molar ratio of methyl halide is about 0.01:1 to about 0.05:1.

[0122] Example 74 is the process of any of Examples 55-73, wherein the vapor phase reactants are about 500 Contains less than ppm by weight of oxygen.

[0123] Example 75 is the process of any of Examples 55-73, wherein the gas phase reactants are about 100 Contains less than ppm by weight of oxygen.

[0124] Example 76 is the process of any of Examples 55-73, wherein the vapor phase reactants are about 10 times Contains less than ppm of oxygen.

[0125] Example 77 is the process of any of Examples 55-73, wherein the vapor phase reactants are about 3 wt. Contains less than ppm of oxygen.

[0126] Example 78 is the process of any of Examples 55-77, wherein the transition metal is nickel, At least one metal selected from the group consisting of cobalt, iron, rhodium, iridium, platinum, and palladium Also includes one.

[0127] Example 79 is the process of any of Examples 55-77, wherein the transition metal is nickel, It consists essentially of platinum, palladium, or a combination thereof.

[0128] Example 80 is the process of any of Examples 55-77, wherein the transition metal is nickel, It consists essentially of platinum, palladium, or a combination thereof.

[0129] Example 81 is the process of any of Examples 55-77, wherein the transition metal is palladium. Basically it consists of:

[0130] Example 82 is the process of any of Examples 55-81, wherein the catalyst is an aluminum oxide. At least one selected from the group consisting of a rubber support, a carbon support, a silica gel support, and a silicon carbide support. It further comprises a carrier comprising one.

[0131] Example 83 is the process of any of Examples 55-81, wherein the catalyst is an aluminum oxide. The carrier further includes a carrier consisting essentially of a rubber carrier.

[0132] Example 84 is the process of any of Examples 82 or 83, further comprising: The transition metal is about 0.01% by weight to about 40% by weight of the total weight of the transition metal and the support.

[0133] Example 85 is the process of Example 84, wherein the transition metal is nickel, cobalt, iron, or bromine. at least one selected from the group consisting of tungsten, iridium, platinum, palladium, and combinations thereof; and the amount of transition metal on the surface of the catalyst is about 5 times the total weight of the transition metal and the support. % to about 35% by weight.

[0134] Example 86 is the process of Example 84, wherein the transition metal is nickel, cobalt, iron, or bromine. at least one selected from the group consisting of tungsten, iridium, platinum, palladium, and combinations thereof; and the amount of transition metal on the surface of the catalyst is about 10% of the total weight of the transition metal and the support. % by weight to about 30% by weight.

[0135] Example 87 is the process of Example 84, wherein the transition metal is nickel, cobalt, iron, or bromine. at least one selected from the group consisting of tungsten, iridium, platinum, palladium, and combinations thereof; and the amount of transition metal on the surface of the catalyst is about 20% of the total weight of the transition metal and the support. % by weight to about 30% by weight.

[0136] Example 88 is the process of Example 84, wherein the transition metal comprises nickel and the support is an acid. The nickel comprises about 21 parts by weight of the total weight of the nickel and aluminum oxide. % by volume.

[0137] Example 89 is the process of Example 84, wherein the transition metal is rhodium, iridium, platinum. , palladium, or a combination thereof, The amount of the transition metal on the surface is about 0.1% by weight to about 5% by weight of the total weight of the transition metal and the support. do.

[0138] Embodiment 90 is the process of embodiment 84, wherein the transition metal is rhodium, iridium, platinum. , palladium, or a combination thereof, The amount of the transition metal on the surface is about 0.3% by weight to about 1% by weight of the total weight of the transition metal and the support. do.

[0139] Example 91 is the process of Example 84, wherein the transition metal is rhodium, iridium, platinum. , palladium, or a combination thereof, The amount of transition metal on the surface is about 0.3 wt % to about 0.7 wt % of the total weight of the transition metal and the support. is.

[0140] Example 92 is the process of Example 84, wherein the transition metal comprises palladium and the support is The palladium content is about 100% by weight of the total of the palladium and aluminum oxide. It is 0.5% by weight.

[0141] Example 93 is the process of any of Examples 55-92, wherein the vapor phase reactants are about 300 It is heated to a temperature of 100°C to about 400°C.

[0142] Example 94 is the process of any of Examples 55-92, wherein the vapor phase reactants are about 320 It is heated to a temperature of about 360°C.

[0143] Example 95 is the process of any of Examples 55-92, wherein the vapor phase reactants are about 340 It is heated to a temperature of about 360°C.

[0144] Embodiment 96 is the process of any of embodiments 55-95, wherein in the reacting step: The contact time of the gas phase reactants with the catalyst is from about 0.1 seconds to about 1,200 seconds.

[0145] Embodiment 97 is the process of any of embodiments 55-95, wherein in the reacting step: The contact time of the gas phase reactants with the catalyst is from about 1 second to about 100 seconds.

[0146] Embodiment 98 is the process of any of embodiments 55-95, wherein in the reacting step: The contact time of the gas phase reactant with the catalyst is from about 2 seconds to about 50 seconds.

[0147] Embodiment 99 is the process of any of embodiments 55-95, wherein in the reacting step: The contact time of the gas phase reactant with the catalyst is about 10 seconds to about 30 seconds.

[0148] Embodiment 100 is the process of any of embodiments 55-99, wherein the process comprises: The trifluoroacetyl halide is separated from the product stream and the separated trifluoroacetyl halide is The method further includes the additional step of recycling the residue to the reaction step.

[0149] Embodiment 101 is the process of any of embodiments 55-100, wherein the process comprises adding unreacted Separating hydrogen iodide from the product stream and recycling the separated hydrogen iodide to the reaction step. The method further includes the additional step of:

[0150] Embodiment 102 is the process of any one of embodiments 55 to 101, wherein the process is a continuous process. It is a process.

[0151] Embodiment 103 is the process of any of embodiments 55-101, wherein the process is a batch It is a process.

[0152] Embodiment 104 is the process of any of Embodiments 55 to 103, wherein the trifluoroacetyl The fluoride is trifluoroacetyl fluoride, trifluoroacetyl chloride, ... fluoroacetyl bromide, and any combination thereof.

[0153] Embodiment 105 is the process of any of embodiments 55 to 103, wherein the trifluoroacetyl The fluorine halide includes trifluoroacetyl chloride.

[0154] Embodiment 106 is the process of any of embodiments 55 to 103, wherein the trifluoroacetyl The fluorine halide consists essentially of trifluoroacetyl chloride.

[0155] Example 107 is the process of any of Examples 55-103, wherein the trifluoroacetyl halide consists essentially of trifluoroacetyl chloride. The present invention includes the following aspects. [1] Trifluoroiodomethane (CF 3 I), a process for producing providing a gas phase reactant comprising trifluoroacetyl halide, hydrogen, and iodine; heating the gas phase reactants; reacting the heated vapor phase reactants in the presence of a catalyst comprising a transition metal to produce trifluoroiodomethane. [2] 2. The process of claim 1, wherein in the providing step, the trifluoroacetyl halide, the iodine, and the hydrogen each contain less than about 500 ppm by weight of water. [3] 3. The process according to claim 1 or 2, wherein in the providing step, the molar ratio of the hydrogen to the iodine is from about 0.1:1 to about 5:1. [4] 4. The process of any one of 1 to 3, wherein the transition metal comprises at least one selected from the group of nickel, cobalt, iron, rhodium, iridium, platinum, and palladium. [5] 5. The process of claim 4, wherein the catalyst further comprises a support comprising at least one selected from the group consisting of an aluminum oxide support, a carbon support, a silica gel support, and a silicon carbide support. [6] 6. The process of claim 5, wherein the transition metal is about 0.01 wt % to about 40 wt % of the total weight of the transition metal and the support. [7] 7. The process of claim 6, wherein the transition metal comprises palladium, the support comprises aluminum oxide, and the palladium is about 0.5 wt. % of the total weight of the palladium and the aluminum oxide. [8] 7. The process of claim 6, wherein the transition metal comprises nickel, the support comprises aluminum oxide, and the nickel is about 21 wt. % of the total weight of the nickel and the aluminum oxide. [9] 9. The process of any one of 1 to 8, wherein the vapor phase reactants are heated to a temperature of from about 200°C to about 600°C.

[10] The process comprises: the additional step of separating unreacted iodine from the trifluoroiodomethane; 10. The process of any one of 1 to 9, further comprising the additional step of returning the unreacted iodine to the providing step.

Claims

1. Trifluoroiodomethane (CF ３ I), a method for producing the compound providing a gas phase reactant comprising trifluoroacetyl halide, hydrogen, and iodine; heating the gas phase reactants; reacting the heated vapor phase reactants in the presence of a transition metal-containing catalyst to produce trifluoroiodomethane; the transition metal comprises at least one selected from the group consisting of nickel, platinum, and palladium; the molar ratio of the hydrogen to the iodine is 0.1:1 to 5:1; and the molar ratio of the hydrogen to the trifluoroacetyl halide is 0.01:1 to 0.05:

1.

2. 2. The method of claim 1, wherein in the providing step, the trifluoroacetyl halide, the iodine, and the hydrogen each contain less than 500 ppm by weight of water.

3. 3. The method of claim 1, wherein in the providing step, the molar ratio of the hydrogen to the iodine is from 0.1:1 to 1:

1.

4. The method of any one of claims 1 to 3, wherein the transition metal comprises palladium.

5. 5. The method of claim 4, wherein the catalyst comprises a support comprising at least one selected from the group consisting of an aluminum oxide support, a carbon support, a silica gel support, and a silicon carbide support.

6. 6. The method of claim 5, wherein the transition metal is 0.01% to 40% by weight of the total weight of the transition metal and the support.

7. 7. The method of claim 6, wherein the transition metal comprises palladium, the support comprises aluminum oxide, and the palladium is 0.5 wt. % of the total weight of the palladium and the aluminum oxide.

8. 7. The method of claim 6, wherein the transition metal comprises nickel, the support comprises aluminum oxide, and the nickel is 21 wt. % of the total weight of the nickel and the aluminum oxide.

9. A method according to any one of claims 1 to 8, wherein the gas phase reactants are heated to a temperature of from 200°C to 600°C.

10. The method comprises: the additional step of separating unreacted iodine from the trifluoroiodomethane; The method of any one of claims 1 to 9, further comprising the additional step of returning the unreacted iodine to the providing step.

11. Trifluoroiodomethane (CF ３ I), a method for producing the compound reacting trifluoroacetyl halide, hydrogen, and iodine in the vapor phase at a temperature between 200°C and 600°C in the presence of a catalyst comprising a transition metal comprising at least one selected from the group of nickel, platinum, and palladium and less than 500 ppm by weight of oxygen to produce a product stream comprising trifluoroiodomethane, unreacted trifluoroacetyl halide, unreacted hydrogen, unreacted iodine, and hydrogen iodide; removing at least a portion of the unreacted iodine from the product stream by cooling the product stream to condense the iodine from the vapor phase; recycling the condensed iodine to the reacting step; wherein the molar ratio of said hydrogen to said iodine is from 0.1:1 to 5:1, and the molar ratio of said hydrogen to said trifluoroacetyl halide is from 0.01:1 to 0.05:

1.

12. 12. The method of claim 11, wherein the molar ratio of the hydrogen to the iodine is from 0.1:1 to 1:

1.

13. The method of claim 11 , wherein the transition metal comprises palladium.

14. 12. The method of claim 11, wherein the catalyst further comprises a support comprising at least one selected from the group consisting of an aluminum oxide support and a carbon support, and the transition metal is 0.01 wt % to 40 wt % of the total weight of the transition metal and the support.

15. The method of claim 11 , wherein the trifluoroacetyl halide comprises trifluoroacetyl chloride.

16. 12. The method of claim 11 further comprising the additional step of separating unreacted trifluoroacetyl halide from the product stream and recycling the separated trifluoroacetyl halide to the reacting step.

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