Trifluoroacetyl iodide composition useful for the production of trifluoroiodomethane
Patent Information
- Application Number
- JP2026099802
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2021-10-06
- Filing Date
- 2026-06-16
- Publication Date
- 2026-09-08
Smart Images
Figure 2026143770000001_ABST
Abstract
Description
[[TECHNICAL FIELD]]
[0001] (CROSS-REFERENCE TO RELATED APPLICATIONS) This application claims priority to U.S. Provisional Patent Application No. 63 / 091,7 25, filed October 14, 2020, and claims priority to U.S. Patent Application No. 1 7 / 495,506, filed October 6, 2021, both of which are incorporated herein by reference in their entireties.
[0002] (Field of the Invention) The present disclosure relates to trifluoroacetyl iodide compositions. Specifically, the present disclosure relates to trifluoroacetyl iodide compositions useful for producing trifluoroiodomethane . [[BACKGROUND ART]]
[0003] Trifluoroiodomethane (CF3I), also known as perfluoromethyl iodide, triflu oromethyl iodide, or iodotrifluoromethane, is a compound useful in commercial applications such as, for example, as a refrigerant or a fire extinguishing agent. Trifluoroiodomethane is a molecule with negligible ozone depletion potential and low global warming potential . Trifluoroiodomethane can replace more environmentally harmful materials.
[0004] Methods for preparing trifluoroacetyl iodide are already known. For example, in the paper "Th e Reactions of Metallic Salts of Acids w ith Halogens.Part I.The Reaction of Meta l Trifluoroacetates with Iodine,Bromine, and Chlorine,”RNHaszeldine,Journal of The Chemical Society, pp. 584-587 (1951) states: Trifluoroacetyl chloride and hydrogen iodide anhydrous were heated without a catalyst at 120°C for 8 hours. By carrying out batch reactions, trifluoroacetyl iodide is produced in a yield of approximately 62%. The instructions are listed.
[0005] U.S. Patent No. 7,196,236 (Mukhopadhyay et al.) is a trifluoro A catalytic process for producing iodomethane is disclosed, and this process requires an iodine source and a small amount of At least a stoichiometric amount of oxygen and reactant CF3R (wherein R is -COOH, -COX,X, -COOH, -COX, -COX, -COX, -COX, -COX, -COX, -COX, -COX, The group consists of CHO, -COOR2, and -SO2X, where R2 is alkyl. This method uses a reactant containing a group (where X is chlorine, bromine, or iodine). The hydrogen iodide that can be produced by the reaction is oxidized by at least a stoichiometric amount of oxygen, It can produce water and iodine, and is eligible for economical recycling.
[0006] U.S. Patent No. 7,132,578 (Mukhopadhyay et al.) also uses a catalyst. The company has disclosed a one-step process in which trifluoroacetylchloroform is used. Trifluoroiodomethane is produced from lyde. However, the iodine source is iodine fluoride. (IF) In contrast to hydrogen iodide, iodine fluoride is relatively unstable, and at 0°C If the amount exceeds a certain limit, it decomposes into I2 and IF5. Iodine fluoride is also commercially useful in useful quantities. It may not be usable in all cases.
[0007] Trifluoroacetyl iodide (CF3COI) to trifluoroiodomethane (C Commercial methods for preparing F3I) are already known. For example, concurrently pending U.S. patent applications. Issue No. 16 / 549,412 is about trifluoroacetyl iodide to trifluoroiodom The process for producing tan and the process for producing trifluoroacetyl iodide The disclosed process is a high-yield gas-phase process and is relatively inexpensive. This method uses inexpensive starting materials that are readily available in commercial quantities.
[0008] The production of trifluoroiodomethane from trifluoroacetyl iodide is desirable. Because there is a risk of adverse reactions, trifluoroacetyl is used to enable more economical operation. A ruyozid composition is required. [Overview of the project]
[0009] This disclosure relates to trifluoroacetyl iodide (CF3COI) and at least one [unclear] A composition comprising an organic impurity and at least one inorganic impurity, wherein trifluoroiodine This invention provides a composition suitable for the production of methane (CF3I).
[0010] In one embodiment, the present invention comprises trifluoroacetyl iodide and at least one The present invention provides a composition comprising an organic impurity and at least one inorganic impurity, and the above at least Another organic impurity is difluoroiodomethane, pentafluoroiodoethane, iodine Methane, iodopropane, dichlorotetrafluoroethane, dichlorotrifluoroethane Trichlorotrifluoroethane, methyltrifluoroacetate, anhydrous trifluorovinegar It comprises at least one of acid, difluorobutane, and methylpropane, and the at least one inorganic impurity is selected from the group consisting of hydrogen iodide, hydrogen chloride, iodine, and trihydrogen iodide and comprises at least one of the foregoing .
[0011] The above and other features of the present disclosure, and modes for implementing them, will become more apparent and better understood by reference to the following description of embodiments herein. BRIEF DESCRIPTION OF THE DRAWINGS
[0012] [Figure 1] It is a process flow diagram showing a gas phase process for producing a trifluoroacetyl iodide composition. [Figure 2] It is a process flow diagram showing a gas phase process for producing trifluoroiodomethane from a trifluoroacetyl iodide composition. MODE FOR CARRYING OUT THE INVENTION
[0013] The present disclosure describes a trifluoroacetyl iodide composition comprising at least one organic impurity and at least one inorganic impurity . It has been found that even with the presence of impurities, the composition is suitable for the production of trifluoroiodomethane .
[0014] The production of trifluoroiodomethane ( CF3I) from trifluoroacetyl iodide (CF3COI) can be carried out in a gas phase reactor according to Formula 1 below: Formula 1: CF3COI → CF3I + CO.
[0015] In the production of trifluoroiodomethane according to Formula 1, trifluoroacetyl iodide is provided as a composition comprising organic impurities and inorganic impurities, since pure trifluoro Luoroacetyliodide makes the production of trifluoroiodomethane economically efficient. This is because it could be too costly. Some impurities are better than others. It was found that this could have a more detrimental impact on the overall efficiency of the process. For example, some hydrogen-containing impurities in the trifluoroacetyl iodide composition and Some halogen-containing impurities include by-products such as methyl trifluoride (CF3H) and iodine (I2). This is thought to lead to an increase in the formation of these by-products. The formation of the desired trifluoroiodomethane product is sacrificed. Hydrogen-containing impurities Examples include trifluoroacetic acid (TFA), hydrogen iodide (HI), and hydrogen chloride (HCl). Examples of halogen-containing impurities include trifluor. Oroacetyl fluoride (CF3COF), trifluoroacetyl chloride (CF3COF) Cl), difluoroiodomethane (CF2HI), pentafluoroiodoethane (CF3) CF2I), iodomethane (CH3I), iodine (I2), iodopropane (C3H7I) Examples include ), and trifluoroiodomethane (CF3I). While n is the desired product, in the trifluoroacetyl iodide composition supplied to the reaction... The trifluoroiodomethane may react with the trifluoroiodomethane to produce undesirable byproducts. .
[0016] Furthermore, certain iodine-containing impurities such as iodine (I2) and hydrogen triiodide (HI3) It is thought that as the concentration increases, corrosion of the processing equipment may increase. If corrosion increases, the processing equipment The effective lifespan of the device may be shortened.
[0017] In contrast, some other organic impurities in the trifluoroacetyl iodide composition are pro It has been found that it has a relatively small impact on Seth's efficiency. These impurities generally pass through the reactor without reacting, thus requiring the processing equipment to be removed. It does not corrode. An example of such an organic impurity is dichlorotetrafluoroethylene (C2Cl2F4), dichlorotrifluoroethane (C2HCl2F3), chlorotri Fluoroethane (C2H2ClF3), Trichlorotrifluoroethane (C2Cl3F3) ), methyl trifluoroacetate (CF3COOCH3), trifluoroacetic anhydride ((CF3 CO)2O), difluorobutane (C4H8F2), and methylpropane (CH3CH( CH3)CH3) is one example.
[0018] A feedstock for producing trifluoroiodomethane according to the process of Formula 1 above. A trifluoroacetyl iodide composition useful as a material is trifluoroacetyl iodide The above comprises a sid, at least one organic impurity, and at least one inorganic impurity. At least one organic impurity is: difluoroiodomethane, pentafluoroiodoethanol Iodomethane, iodopropane, dichlorotetrafluoroethane, dichlorotriflu Oroethane, trichlorotrifluoroethane, methyltrifluoroacetate, anhydrous tri It comprises at least one of fluoroacetic acid, difluorobutane, and methylpropane, The above-mentioned at least one inorganic impurity is: hydrogen iodide, hydrogen chloride, iodine, and water triiodide. It contains at least one of the primes.
[0019] The organic compounds in the trifluoroacetyl iodide composition were analyzed by gas chromatography ( It can be measured by GC analysis and gas chromatography-mass spectroscopy (GC-MS) analysis. The peak areas provided by GC analysis for each organic compound are combined. Then, the GC area percentage (GC area %) relative to the total organic compounds is calculated for each organic compound. Therefore, it can be provided as a measure of the relative concentration of organic compounds in the composition. GC area The percentage can be interpreted as equivalent to weight percentage.
[0020] The concentration of organic impurities in the trifluoroacetyl iodide composition is determined by the GC of all organic compounds. These are relatively low concentrations, such as approximately 0.05%, 0.1%, 0.5%, or 1% per area. It may be, or it may be at a relatively high concentration such as about 2%, about 3%, about 4%, or about 5%. It is also acceptable to do so. Alternatively, the concentration of organic impurities in the trifluoroacetyl iodide composition may be: Any range defined between any two of the aforementioned values, for example, approximately 0.05% to approximately 5%. Approximately 0.1% to 4%, approximately 0.5% to 3%, approximately 1% to 2%, approximately 0.05% to 2%, approximately It may also be 0.5% to approximately 2%, approximately 2% to approximately 5%, or approximately 0.05% to approximately 1%, etc. In other words, the concentration of inorganic impurities in the trifluoroacetyl iodide composition is the same as the total organic compound The GC area percentage may be approximately 0.05% to approximately 3%. More preferably, trifluoro The concentration of inorganic impurities in the cetyl iodide composition is approximately 0.0% in terms of the total organic compound GC area. It may be 5% to about 2%. Most preferably, in the trifluoroacetyl iodide composition The concentration of inorganic impurities may be approximately 0.05% to 1% in terms of the total GC area percentage of the organic compounds. .
[0021] Difluoroiodomethane and iodopropane in trifluoroacetyliodide compositions dichlorotetrafluoroethane, dichlorotrifluoroethane, difluorobutane, The total concentration of methylpropane is, for example, approximately 0.00 in terms of the GC area percentage of the total organic compounds. 0.1%, approximately 0.001%, approximately 0.005%, approximately 0.01%, approximately 0.02%, or approximately 0 A relatively low concentration of around 0.03% is acceptable, or approximately 0.05%, approximately 0.1%, approximately 0.2%, approximately A relatively high concentration of 0.3%, or about 0.5%, is also acceptable. Alternatively, this total concentration is , within any range defined between any two of the aforementioned values, for example, approximately 0.0001% to approximately 0.5%, approximately 0.001% to approximately 0.3%, approximately 0.005% to approximately 0.2%, approximately 0.01% to Approximately 0.1%, approximately 0.001% to approximately 0.2%, approximately 0.001% to approximately 0.03%, approximately 0.05 It may be approximately 0.5%, or approximately 0.1% to 0.3%.
[0022] If trifluoroacetic anhydride is present in the trifluoroacetyl iodide composition, The concentrations are approximately 0.001%, 0.005%, and 0.0% of the total organic compound GC area. It may be a relatively low concentration of 1%, approximately 0.02%, or approximately 0.03%, or approximately 0. 0.5%, approximately 0.1%, approximately 0.2%, approximately 0.3%, approximately 0.5%, or approximately 1% are relatively high. It is not necessary. Alternatively, it can be any range defined between any two of the aforementioned values, for example, Approximately 0.001% to approximately 1%, approximately 0.005% to approximately 0.5%, approximately 0.01% to approximately 0.3%, approximately 0.02% to approximately 0.2%, approximately 0.03% to approximately 0.1%, approximately 0.01% to approximately 0.05%, approximately It may be 0.1% to approximately 1%, or approximately 0.01% to approximately 0.3%.
[0023] Pentafluoroiodoethane is present in the trifluoroacetyl iodide composition. In that case, the concentration is approximately 0.0001% of the total organic compound's GC area percentage, approximately 0.001%. Relatively low concentrations such as approximately 0.005%, 0.01%, 0.02%, or 0.03%. It can be any degree, or approximately 0.05%, 0.1%, 0.2%, 0.3%, or 0. A relatively high concentration, such as 5%, is also acceptable. Alternatively, any value defined between any two of the aforementioned values. Within the range of intent, for example, approximately 0.0001% to approximately 0.5%, approximately 0.001% to approximately 0.3%, approximately 0.005% to approximately 0.2%, approximately 0.01% to approximately 0.1%, approximately 0.001% to approximately 0.2%, Approximately 0.001% to approximately 0.03%, approximately 0.05% to approximately 0.5%, or approximately 0.1% to approximately 0 It may be 0.3% or the like. Preferably, pen in the trifluoroacetyl iodide composition. The concentration of tafluoroiodoethane is approximately 0.0001% to approximately 0% of the total organic compound GC area. It is 0.2%. More preferably, pentafyl in the trifluoroacetyl iodide composition. The concentration of oroiodoethane is approximately 0.0001% to 0.1% in terms of the GC area percentage of all organic compounds. It is %. Most preferably, pentafluoro iodide in the trifluoroacetyl iodide composition. The concentration of ethanol is approximately 0.0001% to 0.05% in terms of the GC area percentage of all organic compounds. be.
[0024] If iodomethane is present in the trifluoroacetyl iodide composition, its concentration These represent the GC area percentage of all organic compounds, approximately 0.0001%, approximately 0.001%, and approximately 0.005%. It is also acceptable to use relatively low concentrations such as approximately 0.01%, approximately 0.02%, or approximately 0.03%, and Comparisons such as approximately 0.05%, approximately 0.1%, approximately 0.2%, approximately 0.3%, or approximately 0.5%. High concentrations are also acceptable. Alternatively, any range defined between any two of the aforementioned values, for example. For example, approximately 0.0001% to approximately 0.5%, approximately 0.001% to approximately 0.3%, approximately 0.005% to Approximately 0.2%, approximately 0.01% to approximately 0.1%, approximately 0.001% to approximately 0.2%, approximately 0.001% ~0.03%, ~0.05%~0.5%, or ~0.1%~0.3%, etc. This may be done. Preferably, the concentration of iodomethane in the trifluoroacetyl iodide composition. This is approximately 0.0001% to approximately 0.2% of the total organic compound GC area. More preferably The concentration of iodomethane in the trifluoroacetyl iodide composition is the G of all organic compounds. The area percentage of C is approximately 0.0001% to approximately 0.1%. Most preferably, trifluoroacetate is used. The concentration of iodomethane in the chilliodide composition is approximately 0.0% in terms of the total organic compound GC area. It is approximately 0.05% to 0.01%.
[0025] Methyltrifluoroacetate is present in the trifluoroacetyliodide composition. In that case, the concentration is approximately 0.001% and approximately 0.005% in terms of the GC area percentage of the total organic compounds. Relatively low concentrations such as approximately 0.01%, 0.02%, 0.03%, or 0.05% This is fine, or approximately 0.1%, approximately 0.2%, approximately 0.3%, approximately 0.5%, approximately 1%, or approximately 2%. Relatively high concentrations such as % are also acceptable. Alternatively, any value defined between any two of the aforementioned values. Within this range, for example, approximately 0.001% to approximately 2%, approximately 0.005% to approximately 1%, approximately 0.01% to Approximately 0.5%, approximately 0.02% to approximately 0.3%, approximately 0.03% to approximately 0.2%, approximately 0.05% to approximately It may also be 0.1%, approximately 0.1% to approximately 1%, or approximately 0.02% to approximately 0.1%, etc.
[0026] Any of the above-mentioned trifluoroacetyl iodide compositions may be trifluoroacetic acid, Lifluoroacetyl fluoride, trifluoroacetyl chloride, trifluoroiodine At least one additive containing at least one of tan and chlorotrifluoroethane It may also contain additional organic impurities.
[0027] If trifluoroacetic acid is present in the trifluoroacetyl iodide composition, The concentrations are approximately 0.001%, 0.005%, and 0.01% of the total organic compound's GC area. It is sufficient to use relatively low concentrations such as approximately 0.02%, approximately 0.03%, or approximately 0.05%, or Comparisons such as approximately 0.1%, 0.2%, 0.3%, 0.5%, 1%, or 2%. High concentrations are also acceptable. Alternatively, any range defined between any two of the aforementioned values, for example. For example, approximately 0.001% to 2%, approximately 0.005% to 1%, approximately 0.01% to 0.5%, Approximately 0.02% to approximately 0.3%, approximately 0.03% to approximately 0.2%, approximately 0.05% to approximately 0.1%, approximately It may be 0.1% to about 1%, or about 0.02% to about 0.1%, etc. Preferably, The concentration of trifluoroacetic acid in the difluoroacetyl iodide composition is determined by the GC of all organic compounds. The area percentage is approximately 0.001% to approximately 1%. More preferably, trifluoroacetyl yogurt. The concentration of trifluoroacetic acid in the zide composition is approximately 0.001% in terms of the GC area of the total organic compounds. The concentration is approximately 0.5%. Most preferably, the trifluoroacetyl iodide in the tri The concentration of fluoroacetic acid is approximately 0.001% to 0.2% in terms of the GC area percentage of the total organic compounds. ru.
[0028] Trifluoroacetyl fluoride is present in the trifluoroacetyl iodide composition. In that case, the concentration would be approximately 0.0001% of the total organic compound's GC area percentage, or approximately 0.000 At relatively low concentrations such as 5%, approximately 0.001%, approximately 0.002%, or approximately 0.003% Often, or approximately 0.005%, approximately 0.01%, approximately 0.02%, approximately 0.03%, or A relatively high concentration, such as approximately 0.05%, is also acceptable. Alternatively, any two values between the aforementioned values may be used. Within any range defined by, for example, approximately 0.0001% to approximately 0.05%, approximately 0.0005 %~approximately 0.03%, approximately 0.001%~approximately 0.02%, approximately 0.002%~approximately 0.01%, approximately 0.003% to approximately 0.005%, approximately 0.0005% to approximately 0.02%, approximately 0.005% to approximately It may be 0.05%, or about 0.001% to about 0.01%. Preferably, The concentration of trifluoroacetyl fluoride in the fluoroacetyl iodide composition is total organic The GC area percentage of the compound is approximately 0.0001% to approximately 0.02%. More preferably, The concentration of trifluoroacetyl fluoride in the fluoroacetyl iodide composition is total organic The GC area percentage of the compound is approximately 0.0001% to approximately 0.01%. Most preferably, The concentration of trifluoroacetyl fluoride in the fluoroacetyl iodide composition is total organic The GC area percentage of the compound is approximately 0.0001% to 0.005%.
[0029] Trifluoroacetyl chloride is present in the trifluoroacetyl iodide composition. In that case, the concentration is approximately 0.001% and approximately 0.005% in terms of the GC area percentage of the total organic compounds. Relatively low concentrations such as approximately 0.01%, 0.02%, 0.03%, or 0.05% This is fine, or approximately 0.1%, approximately 0.2%, approximately 0.3%, approximately 0.5%, approximately 1%, or approximately 2%. Relatively high concentrations such as % are also acceptable. Alternatively, any value defined between any two of the aforementioned values. Within this range, for example, approximately 0.001% to approximately 2%, approximately 0.005% to approximately 1%, approximately 0.01% to Approximately 0.5%, approximately 0.02% to approximately 0.3%, approximately 0.03% to approximately 0.2%, approximately 0.05% to approximately It could be 0.1%, approximately 0.1% to approximately 1%, or approximately 0.02% to approximately 0.1%, etc. Furthermore, the concentration of trifluoroacetyl chloride in the trifluoroacetyl iodide composition The degree is approximately 0.001% to approximately 1% in terms of the GC area % of the total organic compounds. More preferably, The concentration of trifluoroacetyl chloride in the trifluoroacetyl iodide composition is total The GC area percentage of the compound is approximately 0.001% to approximately 0.5%. Most preferably, truffle The concentration of trifluoroacetyl chloride in the oeroacetyl iodide composition is the total organic compound The percentage of the material's GC area is approximately 0.001% to 0.2%.
[0030] In the trifluoroacetyl iodide composition, the presence of trifluoroiodomethane In total, the concentration is approximately 0.0001% of the total organic compound's GC area percentage, approximately 0.001%, approximately The concentration may be relatively low, such as 0.01%, approximately 0.02%, or approximately 0.05%, and It may be a relatively high concentration, such as approximately 0.1%, 0.5%, 1%, or 2%. Alternatively, within any range defined between any two of the aforementioned values, for example, approximately 0.00 0.01% to approximately 2%, approximately 0.001% to approximately 1%, approximately 0.01% to approximately 0.5%, approximately 0.02% to Approximately 0.1%, approximately 0.001% to approximately 0.05%, approximately 0.1% to approximately 0.5%, approximately 0.05% to It may be approximately 0.3%, or approximately 0.001% to approximately 0.03%, etc. Preferably, The concentration of trifluoroiodomethane in the trifluoroacetyliodide composition is determined by the total organic composition. The GC area percentage of the compound is approximately 0.0001% to approximately 1%. More preferably, trifluoro The concentration of trifluoroiodomethane in the acetyl iodide composition is determined by the GC plane of all organic compounds. The product percentage is approximately 0.0001% to approximately 0.5%. Most preferably, trifluoroacetyl The concentration of trifluoroiodomethane in the iodide composition is expressed in GC area % of the total organic compounds. It is approximately 0.0001% to 0.1%.
[0031] In the trifluoroacetyl iodide composition, the presence of chlorotrifluoroethane In total, the concentration is approximately 0.0001% of the total organic compound's GC area percentage, approximately 0.001%, approximately Relatively low concentrations such as 0.005%, approximately 0.01%, approximately 0.02%, or approximately 0.03% However, often, or approximately 0.05%, approximately 0.1%, approximately 0.2%, approximately 0.3%, or approximately 0.5% Relatively high concentrations such as % are also acceptable. Alternatively, any value defined between any two of the aforementioned values. Within this range, for example, approximately 0.0001% to approximately 0.5%, approximately 0.001% to approximately 0.3%, approximately 0 0.005% to approximately 0.2%, approximately 0.01% to approximately 0.1%, approximately 0.001% to approximately 0.2%, approximately 0.001% to approximately 0.03%, approximately 0.05% to approximately 0.5%, or approximately 0.1% to approximately 0.3% You can also use these.
[0032] The concentration of iodine (I2) in a trifluoroacetyl iodide composition is not known in the art. As shown, it can be measured by titration. Hydrogen iodide, hydrogen chloride, triiodide The concentrations of hydrogen ion and other hydrogen-containing inorganic compounds are, as is known in the art, H- It can be measured by NMR.
[0033] The concentration of inorganic impurities in the trifluoroacetyl iodide composition is approximately 0.01 parts by weight. Cent (weight %), approximately 0.02% by weight, approximately 0.03% by weight, or approximately 0.05% by weight Any relatively low concentration is acceptable, or approximately 0.1% by weight, approximately 0.2% by weight, approximately 0.3% by weight Even at relatively high concentrations such as approximately 0.5% by weight, approximately 1% by weight, or approximately 1.5% by weight Good. Or, within any range defined between any two of the aforementioned values, for example, Approximately 0.01% to approximately 1.5% by weight, approximately 0.02% to approximately 1% by weight, approximately 0.03% by weight ~0.5% by weight, approximately 0.05% by weight ~ 0.3% by weight, approximately 0.02% by weight ~ 0.2% by weight Volume%, approximately 0.01% by weight to approximately 0.05% by weight, approximately 0.1% by weight to approximately 1% by weight, or approximately 0. The amount may be 1% to about 0.5% by weight. Preferably, trifluoroacetyl yogurt. The concentration of inorganic impurities in the zide composition is approximately 0.01% to approximately 0.5% by weight. Furthermore, the concentration of inorganic impurities in the trifluoroacetyl iodide composition is approximately 0.01 times. The amount is % to about 0.1% by weight. Most preferably, in the trifluoroacetyl iodide composition. The concentration of inorganic impurities is approximately 0.01% by weight to approximately 0.05% by weight.
[0034] If hydrogen iodide is present in the trifluoroacetyl iodide composition, its concentration is , about 0.0001% by weight, 0.001% by weight, about 0.005% by weight, about 0.01% by weight, The concentration may be relatively low, such as about 0.02% by weight, or about 0.03% by weight, or about 0.05% by weight, approximately 0.1% by weight, approximately 0.2% by weight, approximately 0.3% by weight, or approximately 0.5% by weight It may be a relatively high concentration, such as a percentage of a certain amount. Alternatively, it may be defined between any two of the aforementioned values. Within any range, for example, approximately 0.0001% by weight to approximately 0.5% by weight, approximately 0.001% by weight ~0.5% by weight, approximately 0.005% by weight ~ 0.3% by weight, approximately 0.01% by weight ~ 0.2% by weight Weight%, approx. 0.02% to approx. 0.1%, approx. 0.03% to approx. 0.05%, approx. 0.01% by weight ~ approx. 0.3% by weight, approx. 0.005% by weight ~ approx. 0.03% by weight, approx. 0.05 It can be around 0.5% by weight, or even around 0.05% by weight to 0.3% by weight. Preferably, the concentration of hydrogen iodide in the trifluoroacetyl iodide composition is about 0. The amount is 0.001% by weight to approximately 0.3% by weight. More preferably, trifluoroacetyl iodine The concentration of hydrogen iodide in the composition is approximately 0.0001% by weight to approximately 0.1% by weight. Preferably, the concentration of hydrogen iodide in the trifluoroacetyl iodide composition is about 0.00 It is approximately 0.05% by weight.
[0035] If iodine (I2) is present in the trifluoroacetyl iodide composition, its concentration... The degree is, for example, approximately 0.001% by weight, approximately 0.005% by weight, approximately 0.01% by weight, approximately 0.0 The concentration may be relatively low, such as 2% by weight, or about 0.03% by weight, or about 0.05% by weight. Comparisons such as %, approximately 0.1% by weight, approximately 0.2% by weight, approximately 0.3% by weight, or approximately 0.5% by weight. It may be a very high concentration. Alternatively, any value defined between any two of the aforementioned values. Within the range of intent, for example, approximately 0.001% by weight to approximately 0.5% by weight, approximately 0.005% by weight to approximately 0 .3% by weight, approximately 0.01% by weight to approximately 0.2% by weight, approximately 0.02% by weight to approximately 0.1% by weight, approximately 0.03% to approx. 0.05% by weight, approx. 0.01% to approx. 0.3% by weight, approx. 0.005 Weight % ~ approximately 0.03 weight%, approximately 0.05 weight% ~ approximately 0.5 weight%, or approximately 0.05 weight% It may be approximately 0.3% by weight. Preferably, a trifluoroacetyl iodide composition. The concentration of iodine in the material is approximately 0.001% by weight to approximately 0.3% by weight. More preferably, The iodine concentration in the trifluoroacetyl iodide composition is approximately 0.001% by weight to approximately 0. The concentration of iodine in the trifluoroacetyl iodide composition is 1% by weight. Most preferably, the concentration of iodine in the trifluoroacetyl iodide composition is The degree ranges from approximately 0.001% by weight to approximately 0.05% by weight.
[0036] If hydrogen triiodide is present in the trifluoroacetyl iodide composition, its concentration This is approximately 0.0001% by weight, approximately 0.001% by weight, approximately 0.005% by weight, and approximately 0.01% by weight. The concentration may be relatively low, such as %, approximately 0.02% by weight, or approximately 0.03% by weight. Approximately 0.05% by weight, approximately 0.1% by weight, approximately 0.2% by weight, approximately 0.3% by weight, or approximately 0. It may be a relatively high concentration, such as 5% by weight. Alternatively, it may be defined between any two of the aforementioned values. Within any range, for example, approximately 0.0001% by weight to approximately 0.05% by weight, approximately 0.001 Weight % ~ approx. 0.5 weight %, approx. 0.005 weight % ~ approx. 0.3 weight %, approx. 0.01 weight % ~ approx. 0.2% by weight, about 0.02% to about 0.1% by weight, about 0.03% to about 0.05% by weight %, about 0.01% to about 0.3% by weight, about 0.005% to about 0.03% by weight, about 0 This ranges from 0.05% by weight to approximately 0.5% by weight, or from approximately 0.05% by weight to approximately 0.3% by weight. This may also be the case. Preferably, the concentration of hydrogen triiodide in the trifluoroacetyl iodide composition is The amount is approximately 0.0001% by weight to approximately 0.3% by weight. More preferably, trifluoroacetyl The concentration of hydrogen triiodide in the iodide composition is approximately 0.0001% by weight to approximately 0.1% by weight. Yes. Most preferably, the concentration of hydrogen triiodide in the trifluoroacetyl iodide composition is This ranges from approximately 0.0001% by weight to approximately 0.05% by weight.
[0037] Figure 1 shows an exemplary gas-phase process 10 for producing trifluoroacetyl iodide. This is a process flow diagram. Trifluoroacetyl iodide is a process described below. It may be generated by a process other than Seth. As shown in Figure 1, process 10 is Yo It contains hydrogen citrate (HI) 12 and trifluoroacetyl chloride (CF3COCl) 14. This includes the flow of materials. To illustrate the process in Figure 1, trifluoroacetyl chloride Although is used, trifluoroacetyl bromide or trifluoroacetyl fluoride It is understood that it may be used as a substitute for trifluoroacetyl chloride. The flow of hydrogen citrate 12 and the flow of trifluoroacetyl chloride 14 are combined by the mixing valve 16. This forms the reaction logistics 18. The reaction logistics 18 can be supplied directly to the reactor 20. Alternatively, the reaction logistics 18 is added before the reaction logistics 18 is supplied to the reactor 20. It may pass through the preheating preheater 22.
[0038] Trifluoroacetyl chloride and hydrogen iodide in reaction logistics 18 enter reactor 20 In the presence of catalyst 24, it reacts to produce trifluoroacetyl iodide (CF3COI). This includes various organic and inorganic compounds, including unreacted trifluoroacetyl chloride and hydrogen iodide. This generates a product stream 26 containing impurities.
[0039] The product stream 26 can proceed directly to the distillation column 28. Alternatively, the product stream 26 can proceed as shown in Figure 1. As shown, the product stream 26 passes through the heat exchanger 30 before being supplied to the distillation column 28. It may be overdone. The heat exchanger 30 removes the product before the product stream 26 enters the distillation column 28. The flow 26 is configured to cool. The distillation column 28 contains by-products, reactants, and A portion of the compound was separated from trifluoroacetyl iodide, and the purified product was obtained as flow 3. It is configured to produce 2. As shown in Figure 1, the distillation column 28 is configured to produce hydrogen iodide. In flow 36, unreacted hydrogen iodide is separated for use in reaction flow 18, and hydrogen iodide Return to flow 12, and in trifluoroacetyl chloride flow 34, reaction logistics Unreacted trifluoroacetyl chloride was separated for use in step 18, and trifluoroacetyl chloride It can also be configured to return the flow of tyl chloride 14. The distillation column 28 is also for sale To separate hydrogen chloride into hydrogen chloride stream 38 for sale, reuse elsewhere, or disposal. It can also be configured as follows. The purified product stream 32 sent to the storage tank 40 is as described above. It contains a trifluoroacetyl iodide composition. The purified product flow 32 is stored in a container. It may be further purified before being sent to rink 40.
[0040] Figure 2 shows the trifluoroacetyl iodide composition from any of the above-mentioned trifluoroacetyl iodide compositions. This is a process flow diagram showing process 110 for producing iodomethane. The feed stream 132 containing any of the trifluoroacetyl iodide compositions is as shown in Figure 2. It is supplied to the gas-phase reactor 140. Trifluoroacetyl iodide is supplied to the reactor 140. Then, it reacts at the reaction temperature to produce product stream 144. Product stream 144 is trifluoro It contains iodomethane and carbon monoxide, which is a byproduct of the reaction according to formula 1 above.
[0041] The reaction temperatures are, for example, approximately 200°C, 250°C, 300°C, 310°C, and 320°C. Comparisons of temperatures such as °C, approximately 325°C, approximately 330°C, approximately 340°C, approximately 350°C, or approximately 360°C. It may be a very low temperature, or approximately 370°C, approximately 380°C, approximately 390°C, approximately 400°C, approximately 4 25℃, approximately 450℃, approximately 475℃, approximately 500℃, approximately 525℃, approximately 550℃, approximately 575℃, Relatively high temperatures such as approximately 600°C, 700°C, or 800°C are also acceptable. This is any range defined between any two of the aforementioned values, for example, approximately 200°C~ Approximately 800°C, approximately 250°C to 600°C, approximately 300°C to 500°C, approximately 320°C to 450°C °C, approximately 325°C to approximately 400°C, approximately 330°C to approximately 390°C, approximately 340°C to approximately 380°C, approximately 3 The temperature can be 50°C to approximately 370°C, or approximately 350°C to approximately 450°C, etc. Preferably, The operating temperature is approximately 300°C to 500°C. More preferably, the reaction temperature is approximately 350°C to The temperature is approximately 450°C. Most preferably, the reaction temperature is approximately 375°C to 425°C.
[0042] The reaction may be carried out in the presence of catalyst 142 contained in reactor 140. Catalyst 14 2 is stainless steel, nickel, nickel-chromium alloy, nickel-chromium-molybdenum Alloys, nickel-copper alloys, copper, alumina, silicon carbide, platinum, palladium, rhenium, Carbon (such as Norit-PK35, Calgon, or Shirasagi carbon), or These combinations may include, alternatively or additionally, trifluoroacetyl iodide compositions. The surface of the reactor 140 that comes into contact with the material may itself provide a catalytic effect. Additionally, the reaction proceeds by pyrolysis, or thermal decomposition, of trifluoroacetyl iodide. It can proceed in that way.
[0043] The reaction occurs, for example, at approximately atmospheric pressure, approximately 5 psig (34 kPaG), and approximately 10 psig (69 kPaG). kPaG), approximately 15 psig (103 kPaG), approximately 20 psig (138 kPaG), Approximately 25 psig (172 kPaG), approximately 30 psig (207 kPaG), approximately 35 psi g (241 kPaG), approximately 40 psig (276 kPaG), or approximately 50 psig (3 The reaction is carried out at a relatively low operating pressure, such as 45 kPaG, or at approximately 60 psig (414 kPaG). kPaG), approximately 70 psig (483 kPaG), approximately 80 psig (552 kPaG), Approximately 100 psig (689 kPaG), approximately 120 psig (827 kPaG), approximately 150 psig (1,034 kPaG), approximately 200 psig (1,379 kPaG), approximately 225 psig (1551kPaG), approx. 250psig (1,724kPaG), approx. 275p sig (1,896 kPaG), or approximately 300 psig (2,068 kPaG), etc. The reaction may be carried out at a relatively high reaction operating pressure. Alternatively, the reaction may be carried out at any of the aforementioned values. Any range defined between the two, for example, approximately atmospheric pressure to approximately 300 psig (2,068 psig). kPaG), approx. 5 psig (34 kPaG) ~ approx. 300 psig (2,068 kPaG) Approximately 5 psig (34 kPaG) to approximately 250 psig (1,724 kPaG), approximately 10p sig (69kPaG) to approximately 200psig (1,379kPaG), approximately 15psig ( 103kPaG) to approximately 150psig (1,034kPaG), approximately 20psig (138 kPaG) ~ approx. 120 psig (827 kPaG), approx. 25 psig (172 kPaG) ~Approximately 100 psig (689 kPaG), approximately 30 psig (207 kPaG) ~Approximately 80 p sig (552kPaG), approximately 35psig (241kPaG) to approximately 70psig (48 3 kPaG), approximately 40 psig (276 kPaG) to approximately 70 psig (483 kPaG) Approximately 50 psig (345 kPaG) to approximately 60 psig (414 kPaG), 50 psi g(345kPaG) ~ approx. 250psig (1,724kPaG), approx. 100psig ( 689kPaG) to approximately 200psig (1,379kPaG), or approximately 150psi Reaction working pressures such as g (1,034 kPaG) to approximately 200 psig (1,379 kPaG) The reaction may be carried out at approximately 5 psig (34 kPaG) to approximately 275 ps. The reaction is carried out at a reaction operating pressure of ig (1896 kPaG). More preferably, the reaction is carried out at approximately 10p The reaction is performed at a working pressure of sig (69 kPaG) to approximately 250 psig (1,724 kPaG). The reaction is most preferably carried out at approximately 20 psig (138 kPaG) to approximately 225 psig. The reaction is performed at a reaction operating pressure of (1551 kPaG).
[0044] The trifluoroacetyl iodide composition is the catalyst 142 (and / or the table of reactor 140). (surface) and, for example, approximately 0.01 seconds, approximately 0.05 seconds, approximately 0.1 seconds, approximately 1 second, approximately 2 seconds, approximately 3 seconds, Relatively short contact times, such as approximately 5 seconds, 8 seconds, 10 seconds, 12 seconds, or 15 seconds. over a period of approximately 18 seconds, 20 seconds, 25 seconds, 30 seconds, 35 seconds, 40 seconds, and 50 seconds. Over relatively long contact periods such as seconds, approximately 60 seconds, approximately 300 seconds, or approximately 600 seconds. They may be in contact, or any range defined between any two of the aforementioned values. Over any contact time within the range, for example, from approximately 0.01 seconds to approximately 600 seconds, from approximately 0.1 seconds to approximately 600 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 , and the contact time is approximately 10 seconds to 40 seconds, or approximately 10 seconds to 30 seconds. Good. Preferably, the trifluoroacetyl iodide composition contains catalyst 142 (and / or antagonist). It is in contact with the surface of the device 140 for a contact time of approximately 0.1 seconds to approximately 100 seconds. More preferably, the trifluoroacetyl iodide composition is catalyst 142 (and / or reactor) It is in contact with the surface (140) for a contact time of approximately 0.1 seconds to approximately 60 seconds. Most preferred Alternatively, the trifluoroacetyl iodide composition is catalyst 142 (and / or reactor 140 It is in contact with the surface of the object for a contact time of approximately 0.1 seconds to approximately 10 seconds.
[0045] The product stream 144 can proceed directly to the distillation column 146, as shown in Figure 2. In addition to oroiodomethane and carbon monoxide, product stream 144 contains unreacted trifluoroacetate. It contains chilliodide and other by-products, the latter of which is, for example, trifluoromethane (CHF). 3) Hexafluoroethane (C2F6), and hexafluoroacetone ((CF3)2 These include CO). Distillation column 146 contains unreacted trifluoroacetyl iodide and by-products. Products (such as carbon monoxide, trifluoromethane, and hexafluoroethane) are converted to trifluoro A purified product stream 14 containing trifluoroiodomethane, separated from iodomethane. It is configured to produce 8. As shown in Figure 2, the distillation column 146 is unreacted In trifluoroacetyl iodide stream 150, unreacted trifluoroacetyl iodide It may be configured to separate and return to the feed stream 132. The distillation column 146 is also for sale. To separate carbon monoxide into carbon monoxide stream 152 for reuse elsewhere or disposal. It may be configured as follows.
[0046] Although the present invention has been described as relating to an exemplary design, the present invention is intended to be in accordance with the spirit of this disclosure. Further modifications may be made to the gist and scope of the invention. Furthermore, this application relates to the relevant technical fields. Including such deviations from this disclosure that belong to known or customary practices in It is intended.
[0047] As used herein, "any two of the aforementioned values defined as any The phrase "within the range" means that the values are either in the lower part of the enumeration or in the higher part of the enumeration. Regardless of whether it is located in such a clause, any range is any of the values listed before it. It means that there can be two choices. For example, a pair of values could be two lower values, or two lower values. A higher value, or a choice between a lower value and a higher value, may be made.
[0048] When used herein, the modifier "about" as used in relation to quantity is described as It includes a value and has a meaning determined by the context (for example, it is a measurement of a particular quantity). (including at least the degree of the associated error). When used in a range of contexts, it is equivalent to "approximately". The modifier can also be thought to disclose a range defined by the absolute values of the two endpoints. . [Examples]
[0049] Trifluoroiodomethane from a trifluoroacetyliodide composition according to Formula 1 Manufacturing. In this example, the trifluoroacetyl iodide composition according to the present disclosure is used to obtain trifluoroacetyl iodide from the present disclosure. The success of the production of luoroiodomethane is demonstrated. Figure 2 shows the unit including the operation described above. It was operated for 1,894 hours. Trifluoroacetate was used to supply the reactor. Seven samples of chilliodide compositions were obtained and analyzed for both organic and inorganic compositions. The results are shown in Tables 1 and 2 below. Table 1 shows the organic composition of each sample in GC area %. Table 2 shows the inorganic composition of each sample, relative to the trifluoroacetyl iodide composition by weight (100%). Expressed as a fraction. Each of the trifluoroacetyl iodide compositions is an acceptable trifluoro iodide. Domethane products were produced.
[0050] [Table 1] 1 "Other" includes dichlorotetrafluoroethane, difluoroiodomethane, and dichlorotetrafluoroethane. Lorotrifluoroethane, difluorobutane, and iodopropane, as well as other organic impurities. It contains objects.
[0051] [Table 2] 2 The "Other" category includes hydrogen chloride, but it has not been measured.
[0052] manner Embodiment 1 comprises trifluoroacetyl iodide, at least one organic impurity, and a small amount The composition contains at least one inorganic impurity. At least one organic impurity is a jif Luoroiodomethane, pentafluoroiodoethane, iodomethane, iodopropane, di Chlorotetrafluoroethane, dichlorotrifluoroethane, trichlorotrifluoroethane Tan, methyltrifluoroacetate, trifluoroacetic anhydride, difluorobutane, and It contains at least one of the methylpropane compounds. At least one inorganic impurity is iodide. It contains at least one of hydrogen, hydrogen chloride, iodine, and hydrogen triiodide.
[0053] Embodiment 2 is characterized by at least one organic impurity having a GC area percentage of the total organic compound of approximately 0.0 The composition according to Embodiment 1 is present in an amount of 5 GC area% to approximately 5.0 GC area%.
[0054] Embodiment 3 is characterized by at least one organic impurity having a GC area percentage of the total organic compound of approximately 0.0 The composition according to Embodiment 1 is present in an amount of 5 GC area% to approximately 2.0 GC area%.
[0055] Embodiment 4 is characterized by at least one organic impurity having a GC area percentage of the total organic compound of approximately 0.0 The composition according to Embodiment 1 is present in an amount of 5 GC area% to approximately 1.0 GC area%.
[0056] Embodiment 5 contains at least one organic impurity, with a GC area percentage of the total organic compound of approximately 0.0 A form containing trifluoroacetic anhydride present in an amount of 0.1 GC area% to approximately 1.0 GC area% It is one of the compositions 1 to 4.
[0057] Embodiment 6 contains at least one organic impurity, with a GC area percentage of the total organic compound of approximately 0.0 It contains pentafluoroiodoethane present in an amount of 0.01 GC area % to approximately 0.5 GC area %. The composition is one of the embodiments 1 to 5.
[0058] Embodiment 7 contains at least one organic impurity, with a GC area percentage of the total organic compound of approximately 0.0 Appearances 1 to 6 include iodomethane present in an amount of 0.01 GC area% to approximately 0.5 GC area%. It is one of the following compositions.
[0059] Embodiment 8 contains at least one organic impurity, with a GC area percentage of the total organic compound of approximately 0.0 Contains methyl trifluoroacetate present in an amount of 0.1 GC area % to approximately 2.0 GC area %. The composition is one of the embodiments 1 to 7.
[0060] Embodiment 9 is a state in which at least one organic impurity is present in a total of approximately GC area % of the total organic compound. Difluoroiodomethane is present in amounts ranging from 0.0001 GC area% to approximately 0.5 GC area%. , dichlorotetrafluoroethane, dichlorotrifluoroethane, trichlorotrifluoro at least one of roethane, iodopropane, difluorobutane, and methylpropane A composition according to any of embodiments 1 to 8, including one of the above.
[0061] Embodiment 10 is trifluoroacetic acid, trifluoroacetyl fluoride, trifluoro A small amount of cetyl chloride, trifluoroiodomethane, and chlorotrifluoroethane. Any of embodiments 1 to 9 further comprises at least one additional organic impurity, including at least one of the above. That is the composition.
[0062] Embodiment 11 is characterized by at least one additional organic impurity, in terms of the GC area % of the total organic compound. It contains trifluoroacetic acid present in an amount of approximately 0.001 GC area% to approximately 2.0 GC area%. This is a composition according to embodiment 10.
[0063] Embodiment 12 is characterized by at least one additional organic impurity, in terms of the GC area % of the total organic compound. Trifluoroacetyl is present in amounts ranging from approximately 0.0001 GC area% to approximately 0.05 GC area%. The composition according to embodiment 10 or embodiment 11 contains fluoride.
[0064] Embodiment 13 is characterized by at least one additional organic impurity, in terms of the GC area % of the total organic compound. Trifluoroacetylchloroform is present in amounts ranging from approximately 0.001 GC area% to approximately 2.0 GC area%. The composition is one of embodiments 10 to 12 and contains lidocaine.
[0065] Embodiment 14 is characterized by at least one additional organic impurity, in terms of the GC area % of the total organic compound. Trifluoroiodine meta is present in amounts ranging from approximately 0.0001 GC area % to approximately 2.0 GC area %. The composition is one of embodiments 10 to 13 and contains n.
[0066] Embodiment 15 is characterized by at least one additional organic impurity, in terms of the GC area % of the total organic compound. Chlorotrifluoroethylene is present in amounts of approximately 0.0001 GC area% to approximately 0.5 GC area%. The composition is one of embodiments 10 to 14 and contains n.
[0067] Embodiment 16 contains at least one inorganic impurity in an amount of about 0.01% to about 1.5% by weight of the composition. It is a composition according to any of embodiments 1 to 15, present in an amount of weight percent.
[0068] Embodiment 17 contains at least one inorganic impurity in an amount of about 0.01% to about 0.5% by weight of the composition. It is a composition according to any of embodiments 1 to 15, present in an amount of weight percent.
[0069] Embodiment 18 is a composition in which at least one inorganic impurity is present in an amount of about 0.001% by weight to about 0. The composition is one of embodiments 1 to 17 and contains 5% by weight of iodine.
[0070] Embodiment 19 is a composition in which at least one inorganic impurity is present in an amount of about 0.0001% by weight to about 0% The composition is one of embodiments 1 to 18, containing 0.5% by weight of hydrogen iodide.
[0071] Embodiment 20 is a composition in which at least one inorganic impurity is present in an amount of about 0.0001% by weight to about 0% The composition is one of embodiments 1 to 18, containing 0.5% by weight of hydrogen triiodide.
[0072] Embodiment 21 is characterized by at least one organic impurity present in a GC area percentage of the total organic compound of approximately 0. It is present in an amount of 0.5 GC area % to approximately 5.0 GC area %, and at least one type of inorganic impurity is present in combination. A combination of any of embodiments 1 to 19 present in the product in an amount of approximately 0.01% to approximately 0.5% by weight. It is a finished product.
Claims
1. Trifluoroacetyl iodide and Difluoroiodomethane, pentafluoroiodoethane, iodomethane, iodpro Pan, dichlorotetrafluoroethane, dichlorotrifluoroethane, trichlorotriph Luoroethane, methyltrifluoroacetate, trifluoroacetic anhydride, difluorobutane At least one organic impurity containing at least one of n and methylpropane, A small amount containing at least one of hydrogen iodide, hydrogen chloride, iodine, and triiodide At most one type of inorganic impurity, A composition containing the following:
2. The aforementioned at least one organic impurity accounts for approximately 0.05 GC in terms of GC area percentage of the total organic compound. The composition according to claim 1, present in an amount of area % to about 5.0 GC area %.
3. The aforementioned at least one organic impurity accounts for approximately 0.05 GC in terms of GC area percentage of the total organic compound. The composition according to claim 1, present in an amount ranging from area % to approximately 1.0 GC area %.
4. The aforementioned at least one organic impurity is present in an amount of approximately 0.001 g in terms of GC area % of the total organic compound. Claim 1 comprises trifluoroacetic anhydride present in an amount of C area% to about 1.0 GC area%. The composition described.
5. The aforementioned at least one organic impurity is present in an amount of approximately 0.0001% of the total organic compound's GC area. It contains pentafluoroiodoethane present in an amount of GC area % to approximately 0.5 GC area %, The composition described in item 1. Any one of claims 1 to 5
6. The aforementioned at least one organic impurity is present in an amount of approximately 0.0001% of the total organic compound's GC area. The claim 1 includes iodomethane present in an amount of GC area% to about 0.5 GC area%. composition.
7. The aforementioned at least one organic impurity is present in a GC area percentage of the total organic compound of approximately 0.001 G Contains methyl trifluoroacetate present in an amount of C area % to approximately 2.0 GC area %. The composition described in item 1.
8. The aforementioned at least one organic impurity accounts for approximately 0.0% of the total GC area of the organic compounds. Difluoroiodomethane, dic, is present in amounts ranging from 0.01 GC area% to approximately 0.5 GC area%. Lorotetrafluoroethane, dichlorotrifluoroethane, trichlorotrifluoroethane At least one of iodopropane, difluorobutane, and methylpropane The composition according to claim 1, including
9. Trifluoroacetic acid, trifluoroacetyl fluoride, trifluoroacetyl chloride At least one of the following: dihydroiodomethane, trifluoroiodomethane, and chlorotrifluoroethane The composition according to claim 1, further comprising at least one additional organic impurity containing the above.
10. The aforementioned at least one additional organic impurity is approximately 0.0% in terms of GC area % of the total organic compound. Claim 9, which contains trifluoroacetic acid present in an amount of 0.1 GC area% to about 2.0 GC area%. The composition described above.