Synthesis of trifluoroacetyl iodide (TFAI) from trifluoroacetyl chloride (TFAC) and hydrogen iodide (HI) in a liquid phase reaction

Abstract

The present disclosure provides a process for making trifluoroacetyl iodide (TFAI) in a liquid phase reaction. Specifically, the present disclosure provides a liquid phase reaction of trifluoroacetyl chloride (TFAC) and hydrogen iodide (HI) to form trifluoroacetyl iodide (TFAI), with or without a catalyst. The reaction can be carried out at ambient or elevated temperatures.

Description

[Technical Field]

[0001] (CROSS-REFERENCE TO RELATED APPLICATIONS) This application claims priority to U.S. Patent Application No. 17 / 219,390, filed March 31, 2021, and claims the benefit of U.S. Provisional Patent Application No. 63 / 007,220, filed April 8, 2020, which are incorporated herein by reference in their entireties.

[0002] FIELD OF THE INVENTION The present disclosure provides a process for producing trifluoroacetyl iodide (TFAI) in a liquid phase reaction from trifluoroacetyl chloride (TFAC) and hydrogen iodide (HI), with or without a catalyst. [Background technology]

[0003] Trifluoroiodomethane (CF3I) is an iodofluorocarbon (IFC). IFCs consist primarily of carbon, fluorine, and iodine and have been identified as attractive potential substitutes for chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs). Broadly speaking, IFCs, especially those containing only one iodine atom, are nonflammable and have low boiling points, high volatility, low viscosity, and low surface tension, making them attractive alternative candidates as nonaqueous solvents for replacing CFCs and HCFCs. Iodine-containing organic compounds tend to be toxic, reactive, and chemically unstable, but the presence of a fluorine atom attached to the iodinated carbon atom provides a significant improvement in stability and greatly reduces toxicity. CF3I is nonflammable and has very low acute toxicity, a very low Global Warming Potential (GWP), and a negligible Ozone Depleting Potential (ODP). Additionally, CF3I readily undergoes photolysis when exposed to UV radiation in the aspherical layers of the atmosphere, and therefore never reaches the stratosphere. CF3I's short atmospheric life cycle explains its extremely low GWP and negligible ODP. These properties, along with its compatibility with mineral oils and refrigeration system materials, make it an acceptable, environmentally friendly candidate for applications in refrigeration, fire suppression, aerosol propellants, foam expansion, air conditioning, heat transfer media, and gaseous electrolytes.

[0004] With increasing mandates requiring the gradual reduction of high GWP products, an important objective of the Heating, Ventilation and Air Conditioning (HVAC) industry has been to develop a replacement for the industry-standard refrigerant R410A, a near-azeotropic blend of difluoromethane (HFC-32) and pentafluoroethane (HFC-125), which is flammable, does not contribute to ozone depletion, and has a high GWP.

[0005] A preferred process for making CF3I is to use trifluoroacetyl chloride (TFAC) and hydrogen iodide (HI) as starting materials to make the intermediate product trifluoroacetyl iodide (TFAI), which can be used in the next step reaction to make CF3I.

[0006] The present disclosure provides a process for producing trifluoroacetyl iodide (TFAI) from trifluoroacetyl chloride (TFAC) and hydrogen iodide (HI) in a liquid phase reaction, with or without a catalyst, at ambient or elevated temperatures. Summary of the Invention

[0007] The present disclosure provides a process for making trifluoroacetyl iodide (TFAI) in a liquid phase reaction. Specifically, the present disclosure provides a liquid phase reaction of trifluoroacetyl chloride (TFAC) and hydrogen iodide (HI) to form trifluoroacetyl iodide (TFAI), with or without a catalyst. The reaction can be carried out at ambient or elevated temperatures.

[0008] The present disclosure provides a process for producing trifluoroacetyl iodide (TFAI) in a liquid phase reaction, the process including providing trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst, and reacting the trifluoroacetyl chloride and hydrogen iodide in a liquid phase reactor to produce trifluoroacetyl iodide (TFAI).

[0009] The molar ratio of trifluoroacetyl chloride to hydrogen iodide can be from about 1:10 to about 10:1.

[0010] Preferably, the weight ratio of catalyst to trifluoroacetyl chloride may be from about 0.001:1 to about 0.5:1.

[0011] The catalyst may be selected from the group consisting of silicon carbide, activated carbon, carbon molecular sieves, and combinations thereof.

[0012] The liquid phase reaction of trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst can be carried out at a temperature from about 0°C to about 200°C.

[0013] The present disclosure further provides a process for producing trifluoroacetyl iodide (TFAI) in a liquid phase reaction, the process including combining trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst, and reacting the trifluoroacetyl chloride, hydrogen iodide, and the optional catalyst in a liquid phase reactor to produce trifluoroacetyl iodide and hydrogen chloride.

[0014] The process may further include separating the trifluoroacetyl iodide from the hydrogen chloride.

[0015] The process provided by the present disclosure can be a continuous process.

[0016] The process provided by the present disclosure can be a batch process. [Brief explanation of the drawings]

[0017] [Figure 1] 1 corresponds to Example 1 and shows reactor pressure versus time for the liquid phase synthesis of trifluoroacetyl iodide (TFAI) at ambient temperature. [Figure 2] 1 corresponds to Example 2 and shows the conversion of TFAC and selectivity to TFAI versus reaction time at ambient temperature. [Figure 3] 1 corresponds to Example 3 and shows the conversion of TFAC and selectivity to TFAI versus reaction time at ambient temperature. [Figure 4] 1 corresponds to Example 4 and shows the conversion of TFAC and selectivity to TFAI versus reaction time at 90° C. [Figure 5] 1 corresponds to Example 5 and shows the conversion of TFAC and selectivity to TFAI versus reaction time at 90° C. [Figure 6]1 corresponds to Example 6 and shows the conversion of TFAC and selectivity to TFAI versus reaction time at 60° C. [Figure 7] 1 corresponds to Example 7 and shows the conversion of TFAC and selectivity to TFAI versus reaction time at 60° C. [Figure 8] 1 corresponds to Example 8 and shows the conversion of TFAC and selectivity to TFAI versus reaction time at 60° C. [Figure 9] 1 corresponds to Example 9 and shows the conversion of TFAC and selectivity to TFAI versus reaction time at 120° C. [Figure 10] 10 corresponds to Example 10 and shows the conversion of TFAC and the selectivity to both TFAI and CF3I versus reaction time at 120°C. [Figure 11] 1 corresponds to Example 11 and shows the conversion of TFAC and selectivity to TFAI versus reaction time at 60° C. in the presence of a catalyst. [Figure 12] 1 corresponds to Example 12 and shows the conversion of TFAC and selectivity to TFAI versus reaction time at 60° C. in the presence of a catalyst. [Figure 13] 1 corresponds to Example 13 and shows the conversion of TFAC and selectivity to TFAI versus reaction time at 90° C. in the presence of a catalyst. DETAILED DESCRIPTION OF THE INVENTION

[0018] The present disclosure provides a liquid phase process for producing trifluoroacetyl iodide (TFAI) via the reaction shown in Equation 1 below. Formula 1: CF3COCl+HI→CF3COI+HCl

[0019] The liquid phase process can be carried out in a liquid phase reactor with or without stirring. Preferably, the reactor is equipped with a stirrer and can be constructed in whole or in part from materials including Hastelloy C276, Inconel 600, Inconel 625, Monel 400, SS316, SS316L, PFA processed, PTFE processed, glass processed, and the like.

[0020] The reaction can be carried out under conditions effective to form trifluoroacetyl iodide (TFAI) rather than CF3I, avoiding the difficulties arising from the separation of trifluoroacetyl chloride (TFAC) from CF3I.

[0021] The reaction temperature can be as low as about 0°C, about 25°C, about 35°C, about 40°C, about 50°C, or as high as about 60°C, about 90°C, about 120°C, about 150°C, or about 200°C, or within any range defined between any two of the foregoing values.

[0022] The pressure can be as low as about 5 psig, about 25 psig, about 50 psig, about 100 psig, about 150 psig, about 200 psig, about 250 psig, or as high as about 300 psig, about 350 psig, about 400 psig, about 450 psig, about 500 psig, or within any range defined between any two of the foregoing values.

[0023] The TFAC:HI (trifluoroacetyl chloride:hydrogen iodide) ratio can be as low as about 1:10, about 2:1, about 3:1, or about 4:1, or as high as about 5:1, about 6:1, about 7:1, about 8:1, about 9:1, or about 10:1, or within any range defined between any two of the foregoing values. Preferably, the TFAC:HI ratio is 1:2 to 2:1, e.g., 1:1, 1:1.5, 1:1.9, 1.1:1, 1.5:1, 1.9:1, etc. More preferably, the TFAC / HI ratio is 1:1 to 2:1.

[0024] A catalyst can be added to the reactants. The catalyst can be silicon carbide, activated carbon, carbon molecular sieves, or a combination thereof. The weight ratio of catalyst to TFAC can be as low as about 0.001:1, about 0.01:1, about 0.02:1, about 0.03:1, about 0.04:1, or as high as about 0.05:1, about 0.06:1, about 0.07:1, about 0.08:1, about 0.09:1, about 0.1:1, about 0.2:1, about 0.5:1, or any range defined between any two of the foregoing values.

[0025] The residence time can be a minimum of about 0.1 hours, about 0.5 hours, about 1 hour, about 5 hours, about 10 hours, about 15 hours, or a maximum of about 20 hours, about 30 hours, about 40 hours, about 50 hours, or any range defined between any two of the foregoing values.

[0026] The reaction can be carried out batchwise or continuously. Preferably, the reaction is carried out continuously.

[0027] The reactor may be equipped with a distillation column to remove low-boiling by-products such as HCl. As the reaction progresses, the TFAI concentration increases within the reactor, and a liquid stream can be continuously or intermittently withdrawn for product separation. The isolated TFAI can be sent to a storage tank for use as a feedstock in the next step reaction to make CF3I, while the separated TFAC and / or HI can be recycled to the reactor. [Example]

[0028] The following example demonstrates the production of TFAI from TFAC and HI in a liquid phase process.

[0029] Example 1 Liquid-phase synthesis of trifluoroacetyl iodide (TFAI) at ambient temperature At ambient temperature, 19.94 grams of HI and 22.97 grams of TFAC (TFAC / HI molar ratio of 1.11:1.00) were charged to a 100 mL 316 L reactor equipped with a pressure gauge without stirring. The cylinder pressure was monitored to follow the progress of the reaction with the pressure profile, as shown in Figure 1. After 5.3 hours, the reactor pressure stabilized at 168 psig. After 17.5 hours, the reactor was drained and a liquid sample was analyzed by gas chromatography (GC). The results show a 76.04% conversion of TFAC and a 99.99% selectivity to TFAI. No CF3I formation was observed.

[0030] Example 2 Liquid-phase synthesis of trifluoroacetyl iodide (TFAI) at ambient temperature At ambient temperature, 19.48 grams of HI and 21.21 grams of TFAC (TFAC / HI molar ratio of 1.05:1.00) were charged to a 100 mL 316 L reactor equipped with a pressure gauge and no stirring. Periodically, small liquid samples were drained and analyzed by gas chromatography (GC) to track the progress of the reaction, along with TFAC conversion and TFAI selectivity, as shown in Figure 2. The results show that during the first 12 hours, increasing the reaction time increased TFAC conversion, reaching approximately 85.4% after 14 hours. Nearly 100% selectivity to TFAI was observed throughout the run. No CF3I formation was observed.

[0031] Example 3 Liquid-phase synthesis of trifluoroacetyl iodide (TFAI) at ambient temperature At ambient temperature, 47.71 grams of HI and 70.30 grams of TFAC (TFAC / HI molar ratio of 1.42:1.00) were charged to a 300 mL Teflon-lined PARR reactor equipped with a stirrer. The reactor was agitated for the duration of the test. Periodically, small liquid samples were drained and analyzed by gas chromatography (GC) to track the progress of the reaction, along with TFAC conversion and TFAI selectivity, as shown in Figure 3. After 14 hours, the reactor was drained, and a liquid sample was analyzed by GC. Analysis of the final liquid sample showed 65-66% conversion of TFAC and greater than 99.9% selectivity to TFAI. No CF3I formation was observed.

[0032] Example 4 Liquid-phase synthesis of trifluoroacetyl iodide (TFAI) at 90°C A 300 mL Teflon-lined PARR reactor equipped with a stirrer was charged with 64.33 grams of TFAC. The reactor was stirred and heated to 70°C, and then 56.67 grams of HI (TFAC / HI molar ratio 1.10:1.00) was charged to the reactor. The reactor temperature controller was set to 90°C, and a peak temperature of 98°C was observed due to the exothermic reaction. Periodically, small liquid samples were drained and analyzed by gas chromatography (GC) to track the progress of the reaction, along with TFAC conversion and TFAI selectivity, as shown in Figure 4. After 4 hours, the reactor was drained, and a liquid sample was analyzed by GC. Analysis of the final liquid sample showed approximately 84% conversion of TFAC and greater than 99.9% selectivity to TFAI. No CF3I formation was observed.

[0033] Example 5 Liquid-phase synthesis of trifluoroacetyl iodide (TFAI) at 90°C A 300 mL Teflon-lined PARR reactor equipped with a stirrer was charged with 65.49 grams of TFAC. The reactor was stirred and heated to 70°C, and then 51.08 grams of HI (TFAC / HI molar ratio 1.24:1.00) was charged to the reactor. The reactor temperature controller was set to 90°C, and a peak temperature of 97.7°C was observed due to the exothermic reaction. Periodically, small liquid samples were drained and analyzed by gas chromatography (GC) to track the progress of the reaction, along with TFAC conversion and TFAI selectivity, as shown in Figure 5. After 6 hours, the reactor was drained, and a liquid sample was analyzed by GC. Analysis of the final liquid sample showed 77-78% conversion of TFAC and greater than 99.9% selectivity to TFAI. No CF3I formation was observed.

[0034] Example 6 Liquid-phase synthesis of trifluoroacetyl iodide (TFAI) at 60°C A 300 mL Teflon-lined PARR reactor equipped with a stirrer was charged with 70.63 grams of TFAC. The reactor was stirred and heated to 35°C, and then 61.34 grams of HI (TFAC / HI molar ratio 1.11:1.00) was charged to the reactor. The reactor temperature controller was set to 60°C, and a peak temperature of 61.5°C was observed due to the exothermic reaction. Periodically, small liquid samples were drained and analyzed by gas chromatography (GC) to track the progress of the reaction, along with TFAC conversion and TFAI selectivity, as shown in Figure 6. After 6 hours, the reactor was drained, and a liquid sample was analyzed by GC. Analysis of the final liquid sample showed approximately 85% conversion of TFAC and greater than 99.9% selectivity to TFAI. No CF3I formation was observed.

[0035] Example 7 Liquid-phase synthesis of trifluoroacetyl iodide (TFAI) at 60°C A 300 mL Teflon-lined PARR reactor equipped with a stirrer was charged with 74.18 grams of TFAC. The reactor was stirred and heated to 35°C, and then 42.58 grams of HI (TFAC / HI molar ratio 1.68:1.00) was charged to the reactor. The reactor temperature controller was set to 60°C, and a peak temperature of 65°C was observed due to the exothermic reaction. Periodically, small liquid samples were drained and analyzed by gas chromatography (GC) to track the progress of the reaction, along with TFAC conversion and TFAI selectivity, as shown in Figure 7. After 10.5 hours, the reactor was drained, and a liquid sample was analyzed by GC. Analysis from the final liquid sample indicated approximately 60% conversion of TFAC and nearly 100% selectivity to TFAI. No CF3I formation was observed.

[0036] Example 8 Liquid-phase synthesis of trifluoroacetyl iodide (TFAI) at 60°C A 300 mL Teflon-lined PARR reactor equipped with a stirrer was charged with 75.10 grams of TFAC. The reactor was stirred and heated to 35°C, and then 38.77 grams of HI (TFAC / HI molar ratio 1.87:1.00) was charged to the reactor. The reactor temperature controller was set to 60°C, and a peak temperature of 66.3°C was observed due to the exothermic reaction. Periodically, small liquid samples were drained and analyzed by gas chromatography (GC) to track the progress of the reaction, along with the TFAC conversion and TFAI selectivity shown in Figure 8. After 6 hours, the reactor was drained, and a liquid sample was analyzed by GC. Analysis of the final liquid sample showed 51-52% conversion of TFAC and nearly 100% selectivity to TFAI. No CF3I formation was observed.

[0037] Example 9 Liquid-phase synthesis of trifluoroacetyl iodide (TFAI) at 120°C A 300 mL Teflon-lined PARR reactor equipped with a stirrer was charged with 65.60 grams of TFAC. The reactor was stirred and heated to 85°C, and then 56.12 grams of HI (TFAC / HI molar ratio 1.13:1.00) was charged to the reactor. The reactor temperature controller was set to 120°C, and a peak temperature of 121.3°C was observed due to the exothermic reaction. Periodically, small liquid samples were drained and analyzed by gas chromatography (GC) to track the progress of the reaction, along with TFAC conversion and TFAI selectivity, as shown in Figure 9. After 5 hours, the reactor was drained, and a liquid sample was analyzed by GC. Analysis of the final liquid sample showed 80-81% conversion of TFAC, 99.79% selectivity to TFAI, and 0.10% selectivity to CF3I.

[0038] Example 10 Liquid-phase synthesis of trifluoroacetyl iodide (TFAI) at 120°C A 300 mL Teflon-lined PARR reactor equipped with a stirrer was charged with 61.08 grams of TFAC. The reactor was stirred and heated to 85°C, and then 40.99 grams of HI (TFAC / HI molar ratio 1.44:1.00) was charged to the reactor. The reactor temperature controller was set to 120°C, and a peak temperature of 120.9°C was observed due to the exothermic reaction. Periodically, small liquid samples were drained and analyzed by gas chromatography (GC) to track the progress of the reaction, along with TFAC conversion and TFAI selectivity, as shown in Figure 10. After 3 hours, the reactor was drained, and a liquid sample was analyzed by GC. Analysis of the final liquid sample showed 72-73% conversion of TFAC, 99.82% selectivity to TFAI, and 0.13% selectivity to CF3I.

[0039] Example 11 Liquid-phase synthesis of trifluoroacetyl iodide (TFAI) with catalysts 1.13 grams of silicon carbide (SiC) catalyst and 71.44 grams of TFAC were loaded into a 300 mL Teflon-lined PARR reactor equipped with a stirrer. The weight ratio of catalyst to TFAC was 0.016:1.00. The reactor was stirred and heated to 35°C, and then 65.39 grams of HI were loaded into the reactor (TFAC / HI molar ratio 1.05:1.00). The reactor temperature controller was set to 60°C, and a peak temperature of 60.2°C was observed due to the exothermic reaction. Periodically, small liquid samples were drained and analyzed by gas chromatography (GC) to track the progress of the reaction, along with the TFAC conversion and TFAI selectivity shown in Figure 11. After 5 hours, the reactor was drained, and the liquid samples were analyzed by GC. Analysis of the final liquid sample showed 85-86% conversion of TFAC and 99.9% selectivity for TFAI. No CF3I formation was observed.

[0040] Example 12 Liquid-phase synthesis of trifluoroacetyl iodide (TFAI) with catalysts 1.09 grams of silicon carbide (SiC) catalyst and 74.95 grams of TFAC were loaded into a 300 mL Teflon-lined PARR reactor equipped with a stirrer. The weight ratio of catalyst to TFAC was 0.014:1.00. The reactor was stirred and heated to 35°C, and then 53.80 grams of HI were loaded into the reactor (TFAC / HI molar ratio 1.35:1.00). The reactor temperature controller was set to 60°C, and a peak temperature of 60.9°C was observed due to the exothermic reaction. Periodically, small liquid samples were drained and analyzed by gas chromatography (GC) to track the progress of the reaction, along with the TFAC conversion and TFAI selectivity shown in Figure 12. After 5 hours, the reactor was drained, and a liquid sample was analyzed by GC. Analysis of the final liquid sample indicated 72-73% conversion of TFAC and greater than 99.9% selectivity to TFAI. No CF3I formation was observed.

[0041] Example 13 Liquid-phase synthesis of trifluoroacetyl iodide (TFAI) with catalysts 1.10 grams of silicon carbide (SiC) catalyst and 76.26 grams of TFAC were loaded into a 300 mL Teflon-lined PARR reactor equipped with a stirrer. The weight ratio of catalyst to TFAC was 0.014:1.00. The reactor was stirred and heated to 75°C, and then 57.12 grams of HI were loaded into the reactor (TFAC / HI molar ratio 1.29:1.00). The reactor temperature controller was set to 90°C, and a peak temperature of 107.3°C was observed due to the exothermic reaction. Periodically, small liquid samples were drained and analyzed by gas chromatography (GC) to track the progress of the reaction, along with the TFAC conversion and TFAI selectivity shown in Figure 13. After 6 hours, the reactor was drained, and the liquid samples were analyzed by GC. Analysis of the final liquid sample showed 74-75% conversion of TFAC and greater than 99.9% selectivity for TFAI. No CF3I formation was observed.

[0042] Example 14 Liquid-phase synthesis of trifluoroacetyl iodide (TFAI) Hydrogen iodide (172.7 grams) and 20.0 grams of TFAC (TFAC / HI molar ratio of 1.0:9.0) are charged to a 100 mL 316 L reactor equipped with a pressure gauge and no stirring. Periodically, small liquid samples are drained and analyzed by gas chromatography (GC) to monitor the progress of the reaction, along with TFAC conversion and TFAI selectivity. After a period of time, the reactor is drained and a liquid sample is analyzed by GC.

[0043] Example 15 Liquid-phase synthesis of trifluoroacetyl iodide (TFAI) Hydrogen iodide (20.0 grams) and 165.6 grams of TFAC (TFAC / HI molar ratio of 8.0:1.0) are charged to a 100 mL 316 L reactor equipped with a pressure gauge and no stirring. Periodically, small liquid samples are drained and analyzed by gas chromatography (GC) to monitor the progress of the reaction, along with TFAC conversion and TFAI selectivity. After a period of time, the reactor is drained and a liquid sample is analyzed by GC.

[0044] Example 16 Liquid-phase synthesis of trifluoroacetyl iodide (TFAI) at 200°C A 300 mL Teflon-lined PARR reactor equipped with a stirrer is charged with 61.08 grams of TFAC. The reactor is stirred and heated to 180°C, and then 40.99 grams of HI are charged to the reactor (TFAC / HI molar ratio 1.44:1.00). The reactor temperature controller is set at 200°C. Periodically, small liquid samples are drained and analyzed by gas chromatography (GC) to track the progress of the reaction, along with TFAC conversion and TFAI selectivity. After a period of time, the reactor is drained and the liquid samples are analyzed by GC.

[0045] It should be understood that the foregoing description is merely illustrative of the present disclosure. Various alternatives and modifications may be devised by those skilled in the art without departing from the present disclosure. Accordingly, the present disclosure is intended to embrace all such alternatives, modifications, and variations that fall within the scope of the appended claims.

[0046] Aspects Aspect 1 is a process for producing trifluoroacetyl iodide (TFAI), comprising providing trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst, and reacting the trifluoroacetyl chloride and hydrogen iodide to provide trifluoroacetyl iodide.

[0047] Aspect 2 is the process of Aspect 1, wherein in the providing step, the molar ratio of trifluoroacetyl chloride to hydrogen iodide is from about 1:10 to about 10:1.

[0048] Example 3 is the process of Example 1 or 2, wherein in the providing step, the weight ratio of catalyst to trifluoroacetyl chloride is from about 0.001:1 to about 0.5:1.

[0049] Example 4 is the process of any one of Examples 1 to 3, wherein the catalyst is selected from the group consisting of silicon carbide, activated carbon, carbon molecular sieves, and combinations thereof.

[0050] Aspect 5 is the process of any one of aspects 1 to 4, wherein in the reacting step, trifluoroacetyl iodide, hydrogen iodide, and optional catalyst are at a temperature of 0°C to 200°C.

[0051] A sixth aspect is a process for producing trifluoroacetyl iodide (TFAI) in a liquid phase reaction, comprising combining trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst; and heating the trifluoroacetyl chloride, hydrogen iodide, and optional catalyst to produce trifluoroacetyl iodide and hydrogen chloride.

[0052] Example 7 is the process of Example 6, further comprising separating trifluoroacetyl iodide from hydrogen chloride, trifluoroacetyl chloride, and hydrogen iodide.

[0053] Example 8 is the process of example 6 or example 7, wherein the process is a continuous process.

[0054] Aspect 9 is the process of aspect 6 or 7, wherein the process is a batch process.

[0055] Example 10 is the process of any one of Examples 6 to 9, wherein the catalyst is selected from the group consisting of silicon carbide, activated carbon, carbon molecular sieves, and combinations thereof.

[0056] Example 11 is the process of any one of Examples 6 to 10, wherein in the reacting step, the trifluoroacetyl iodide, hydrogen iodide, and optional catalyst are at a temperature from 0°C to 200°C.

[0057] Example 12 is the process of any one of Examples 6 to 11, wherein in the reacting step, the trifluoroacetyl chloride, hydrogen iodide, and optional catalyst are at a pressure of 5 psig to 500 psig. The present invention includes the following aspects. [1] 1. A process for producing trifluoroacetyl iodide (TFAI) in a liquid phase reaction, comprising: providing trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst; reacting said trifluoroacetyl chloride and hydrogen iodide to provide trifluoroacetyl iodide. [2] 2. The process according to 1, wherein in the providing step, the molar ratio of the trifluoroacetyl chloride to the hydrogen iodide is from about 1:10 to about 10:1. [3] 3. The process according to claim 1 or 2, wherein in the providing step, the weight ratio of the catalyst to the trifluoroacetyl chloride can be from about 0.001:1 to about 0.5:1. [4] 4. The process of any one of 1 to 3, wherein the catalyst is selected from the group consisting of silicon carbide, activated carbon, carbon molecular sieves, and combinations thereof. [5] 1. A process for producing trifluoroacetyl iodide (TFAI) in a liquid phase reaction, comprising: combining trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst; heating said trifluoroacetyl chloride, hydrogen iodide, and optional catalyst to produce trifluoroacetyl iodide and hydrogen chloride. [6] 6. The process of claim 5, further comprising separating the trifluoroacetyl iodide from the hydrogen chloride, trifluoroacetyl chloride, and hydrogen iodide. [7] 7. The process of claim 5 or 6, wherein the process is one of a continuous process and a batch process. [8] 8. The process of any one of claims 5 to 7, wherein the catalyst is selected from the group consisting of silicon carbide, activated carbon, carbon molecular sieves, and combinations thereof. [9] 9. The process of any one of claims 5 to 8, wherein in the reacting step, the trifluoroacetyl iodide, the hydrogen iodide, and the optional catalyst are at a temperature of 0°C to 200°C.

[10] 10. The process of any one of claims 5 to 9, wherein in the reacting step, the trifluoroacetyl chloride, the hydrogen iodide, and the optional catalyst are at a pressure of 5 psig to 500 psig.

Claims

1. 1. A continuous process for producing trifluoroacetyl iodide (TFAI) in a liquid phase reaction, comprising: providing trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst; reacting said trifluoroacetyl chloride and hydrogen iodide in a liquid phase in a reactor at a temperature of 0°C to 90°C for a residence time of 0.1 hours to 5 hours to provide trifluoroacetyl iodide.

2. 2. The process of claim 1, wherein in said providing step, the molar ratio of said trifluoroacetyl chloride to said hydrogen iodide is from 1:10 to 10:

1.

3. The process of any one of claims 1 to 2, wherein the catalyst is selected from the group consisting of silicon carbide, activated carbon, carbon molecular sieves, and combinations thereof.

4. 4. The process of any one of claims 1 to 3, wherein in the reacting step, the trifluoroacetyl chloride, the hydrogen iodide, and the optional catalyst are at a temperature of from 25°C to 90°C.

5. 1. A continuous process for producing trifluoroacetyl iodide (TFAI) in a liquid phase reaction, comprising: combining trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst; reacting said trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst in a liquid phase in a reactor at a temperature between 0°C and 90°C to produce trifluoroacetyl iodide and hydrogen chloride.

6. 6. The process of claim 5, further comprising separating the trifluoroacetyl iodide from the hydrogen chloride, trifluoroacetyl chloride, and hydrogen iodide.

7. 7. The process of any one of claims 5 to 6, wherein the catalyst is selected from the group consisting of silicon carbide, activated carbon, carbon molecular sieves, and combinations thereof.

8. 8. The process of any one of claims 5 to 7, wherein the reacting of the trifluoroacetyl chloride, the hydrogen iodide, and the optional catalyst is at a temperature of from 25°C to 90°C.

9. 9. The process of any one of claims 5 to 8, wherein the trifluoroacetyl chloride, the hydrogen iodide, and the optional catalyst in the reaction are at a pressure of from 5 psig to 500 psig.

10. The process of claim 1, further comprising: separating the trifluoroacetyl iodide from the trifluoroacetyl chloride and the hydrogen iodide; recycling said trifluoroacetyl chloride and said hydrogen iodide to the reactor; The process of any one of claims 1 to 4, further comprising:

11. The process of claim 10, further comprising: separating the trifluoroacetyl iodide from the hydrogen chloride, the trifluoroacetyl chloride, and the hydrogen iodide; recycling said trifluoroacetyl chloride and said hydrogen iodide to the reactor; The process of any one of claims 5 to 9, further comprising:

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