Method for producing fluorine-containing aromatic compounds

Abstract

To provide a novel method for efficiently producing fluorine-containing aromatic compounds.SOLUTION: A production method of fluorine-containing aromatic compounds comprises a step of causing a reaction between a compound represented by a general formula (2) and a metal fluoride to fluorinate two or more X1 in the case where n is an integer of 2 or more, in a solvent containing a nitrogen-containing organic compound, in the presence of a phosphonium salt having one or more alkyl groups, wherein R1 represents a hydrogen atom, a hydroxy group, a fluorine atom, a cyano group, a nitro group, a hydrocarbon group, or a perfluoroalkyl group; and X1 may be the same or different and represents a halogen atom other than a fluorine atom.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present disclosure relates to a method for producing a fluorine-containing aromatic compound. [Background technology]

[0002] As a method for producing a fluorine-containing aromatic compound represented by perfluorotoluene, which is expected to be used as a next-generation etching gas, etc., it is known to fluorinate a halogenated aromatic compound with 1.2 to 1.4 equivalents of an alkali metal or alkaline earth metal fluoride using, for example, 1 to 5 mass % of a tetrakis(diethylamino)phosphonium salt as a catalyst (see Patent Document 1). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Russian Patent Publication No. 2157800 Summary of the Invention [Problem to be solved by the invention]

[0004] An object of the present disclosure is to provide a novel method capable of efficiently producing a fluorine-containing aromatic compound. [Means for solving the problem]

[0005] The present disclosure encompasses the following configurations.

[0006] Term 1. General formula (1):

[0007] [ka]

[0008] [In the formula, R 1 represents a hydrogen atom, a hydroxyl group, a fluorine atom, a cyano group, a nitro group, a hydrocarbon group, or a perfluoroalkyl group. 1are the same or different and represent a halogen atom other than a fluorine atom. n represents an integer of 1 to 6. n1 represents an integer of 1 to 6. However, when n≧n1 and n is an integer of 2 to 6, n1 represents an integer of 2 to 6.] A method for producing a compound represented by the following formula: In a solvent containing a nitrogen-containing organic compound, In the presence of a phosphonium salt having one or more alkyl groups, General formula (2):

[0009] [ka]

[0010] [In the formula, R 1 , X 1 and n is the same as above.] A compound represented by the formula: When n is an integer of 2 or more, two or more X are reacted with the metal fluoride. 1 to produce a compound represented by the general formula (1). A manufacturing method comprising:

[0011] Item 2. The method according to Item 1, wherein the fluorination is carried out in a system having a water content of 700 ppm by mass or less.

[0012] Item 3. The method according to item 1 or 2, wherein n is an integer of 3 to 6.

[0013] Item 4. The method according to any one of Items 1 to 3, wherein the metal fluoride is a fluoride of an alkali metal or an alkaline earth metal.

[0014] Item 5. A composition comprising difluorobenzotrifluoride and at least one halogenated fluorobenzotrifluoride selected from the group consisting of chlorofluorobenzotrifluoride, bromofluorobenzotrifluoride and iodofluorobenzotrifluoride.

[0015] Item 6. The composition according to Item 5, wherein the content of the difluorobenzotrifluoride is 60.0 to 99.9 mol % and the content of the halogenated fluorobenzotrifluoride is 0.1 to 40.0 mol %, based on 100 mol % of the total amount of the composition.

[0016] Item 7. The composition according to item 5 or 6, which is used as a solvent for organic synthesis, an intermediate for agricultural chemicals, or an intermediate for pharmaceuticals.

[0017] Item 8. A composition containing pentafluorobenzotrifluoride and at least one halogenated fluorobenzotrifluoride selected from the group consisting of chlorotetrafluorobenzotrifluoride, bromotetrafluorobenzotrifluoride, iodotetrafluorobenzotrifluoride, dichlorotrifluorobenzotrifluoride, dibromotrifluorobenzotrifluoride, diiodotrifluorobenzotrifluoride, trichlorodifluorobenzotrifluoride, tribromodifluorobenzotrifluoride, triiododifluorobenzotrifluoride, tetrachlorofluorobenzotrifluoride, tetrabromofluorobenzotrifluoride, and tetraiodofluorobenzotrifluoride.

[0018] Item 9. The composition according to item 8, wherein the content of the pentafluorobenzotrifluoride is 60.0 to 99.9 mol % and the content of the halogenated fluorobenzotrifluoride is 0.1 to 40.0 mol %, based on 100 mol % of the total amount of the composition.

[0019] Item 10. The gas according to item 8 or 9, which is used as an etching gas or a cleaning gas. composition. Effect of the Invention

[0020] According to the present disclosure, a novel method for efficiently producing a fluorine-containing aromatic compound can be provided. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0021] In this specification, the term "containing" is a concept that encompasses all of "comprise," "consist essentially of," and "consist only of."

[0022] In this specification, when a numerical range is indicated as "A to B," it means A or more and B or less.

[0023] In the present disclosure, "selectivity" means the ratio (mol %) of the total molar amount of the target compound contained in the effluent gas from the reactor outlet to the total molar amount of compounds other than the raw material compound in the effluent gas.

[0024] In the present disclosure, the term "conversion rate" means the ratio (mol %) of the total molar amount of compounds other than the raw material compounds contained in the effluent gas from the reactor outlet to the molar amount of the raw material compounds supplied to the reactor.

[0025] In the present disclosure, the term "yield" refers to the ratio (mol %) of the total molar amount of the target compound contained in the effluent gas from the reactor outlet to the molar amount of the raw material compounds supplied to the reactor.

[0026] Patent Document 1 describes the use of 1 to 5 mass % of tetrakis(diethylamino)phosphonium salt as a catalyst to fluorinate a halogenated aromatic compound with 1.2 to 1.4 equivalents of an alkali metal or alkaline earth metal fluoride (particularly potassium fluoride). However, among these, tetrakis(diethylamino)phosphonium salt is not commercially available, and the synthesis cost is high, making this method impractical. Therefore, a new method for producing a fluorine-containing aromatic compound is desired.

[0027] According to the present disclosure, in a method of reacting a specific halogenated aromatic compound with a metal fluoride in the presence of a phosphonium salt having one or more alkyl groups, by setting desired reaction conditions (using a specific solvent, adjusting the amount of water in the system to a specific range, employing a specific substrate, or employing a specific phosphonium salt), all halogen atoms other than fluorine in the halogenated aromatic compound can be fluorinated to efficiently produce a fluorine-containing aromatic compound, and in particular, the fluorine-containing aromatic compound can be produced with high conversion, high selectivity, and high yield.

[0028] 1. Method for producing fluorine-containing aromatic compounds (part 1) The manufacturing method according to the first aspect of the present disclosure includes: General formula (1):

[0029] [ka]

[0030] [In the formula, R 1 represents a hydrogen atom, a hydroxyl group, a fluorine atom, a cyano group, a nitro group, a hydrocarbon group, or a perfluoroalkyl group. 1 are the same or different and represent a halogen atom other than a fluorine atom. n represents an integer of 1 to 6. n1 represents an integer of 1 to 6. However, when n≧n1 and n is an integer of 2 to 6, n1 represents an integer of 2 to 6.] A method for producing a compound represented by the following formula: In a solvent containing a nitrogen-containing organic compound, In the presence of a phosphonium salt having one or more alkyl groups, General formula (2):

[0031] [ka]

[0032] [In the formula, R 1 , X 1 and n is the same as above.] A compound represented by the formula: When n is an integer of 2 or more, two or more X are reacted with the metal fluoride. 1 to produce a compound represented by the general formula (1). Equipped with.

[0033] (1-1) Starting compound (general formula (2)) In the production method of the first embodiment of the present disclosure, the compound represented by general formula (2) is a compound represented by general formula (2):

[0034] [ka]

[0035] [In the formula, R 1 represents a hydrogen atom, a hydroxyl group, a fluorine atom, a cyano group, a nitro group, a hydrocarbon group, or a perfluoroalkyl group. 1 are the same or different and represent a halogen atom other than a fluorine atom. n represents an integer of 1 to 6. It is a compound represented by the formula:

[0036] In the general formula (2), R 1 The hydrocarbon group represented by the formula (I) is not particularly limited, and examples thereof include alkyl groups, aryl groups, and groups formed by any combination thereof (for example, aralkyl groups, alkylaryl groups, and alkylaralkyl groups).

[0037] In the general formula (2), R 1The alkyl group as the hydrocarbon group represented by the formula (I) includes any of linear, branched, or cyclic (preferably linear or branched, more preferably linear). The number of carbon atoms in the alkyl group (in the case of linear or branched) is not particularly limited, and from the viewpoints of the conversion rate of the reaction, the selectivity of the compound represented by the general formula (1), the yield of the compound represented by the general formula (1), etc., it is preferably, for example, 1 to 20, more preferably 3 to 15, and even more preferably 5 to 10. The number of carbon atoms in the alkyl group (in the case of cyclic) is not particularly limited, and from the viewpoints of the conversion rate of the reaction, the selectivity of the compound represented by the general formula (1), the yield of the compound represented by the general formula (1), etc., it is preferably, for example, 3 to 8, and more preferably 4 to 7.

[0038] Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, a neopentyl group, an n-hexyl group, a 3-methylpentyl group, an n-heptyl group, an n-octyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.

[0039] In the general formula (2), R 1 The aryl group as the hydrocarbon group represented by is not particularly limited, but from the viewpoints of the conversion rate of the reaction, the selectivity of the compound represented by general formula (1), the yield of the compound represented by general formula (1), etc., it is preferable that the number of carbon atoms is 6 to 20, more preferably 6 to 12, and further preferably 6 to 10. The aryl group may be either monocyclic or polycyclic (e.g., bicyclic, tricyclic, etc.), but is preferably monocyclic.

[0040] Specific examples of the aryl group include a phenyl group, a naphthyl group, a biphenyl group, a pentalenyl group, an indenyl group, an anthranyl group, a tetracenyl group, a pentacenyl group, a pyrenyl group, a perylenyl group, a fluorenyl group, and a phenanthryl group.

[0041] In the general formula (2), R 1The aralkyl group as the hydrocarbon group represented by the formula (I) is not particularly limited, but from the viewpoint of the conversion rate of the reaction, the selectivity of the compound represented by the general formula (1), the yield of the compound represented by the general formula (1), etc., examples thereof include aralkyl groups in which hydrogen atoms (e.g., 1 to 3, preferably 1 hydrogen atom) of a linear or branched alkyl group having 1 to 6 carbon atoms (preferably 1 to 3) are substituted with the above-mentioned aryl group.

[0042] Specific examples of the aralkyl group include a benzyl group and a phenethyl group.

[0043] In the general formula (2), R 1 The alkylaryl group as the hydrocarbon group represented by the formula (I) is not particularly limited, but from the viewpoint of the conversion rate of the reaction, the selectivity of the compound represented by the general formula (1), the yield of the compound represented by the general formula (1), etc., examples thereof include alkylaryl groups in which hydrogen atoms (e.g., 1 to 3, preferably 1 hydrogen atom) of the aryl group are substituted with linear or branched alkyl groups having 1 to 6 carbon atoms (preferably 1 to 2).

[0044] Specific examples of the alkylaryl group include a tolyl group and a xylyl group. can be done.

[0045] In the general formula (2), R 1 The alkylaralkyl group as the hydrocarbon group represented by the formula: From the viewpoints of the conversion rate of the reaction, the selectivity of the compound represented by the general formula (1), the yield of the compound represented by the general formula (1), and the like, examples of the aralkyl group include alkylaralkyl groups in which a hydrogen atom (for example, 1 to 3, preferably 1 hydrogen atom) on the aromatic ring of the aralkyl group is substituted with a linear or branched alkyl group having 1 to 6 carbon atoms (preferably 1 to 2).

[0046] In the general formula (2), R 1Examples of the substituent of the hydrocarbon group represented by the formula include an alkoxy group, a halogen atom, etc. The number of the substituents is not particularly limited, and is, for example, preferably 0 to 6, more preferably 0 to 3, and further preferably 0 to 1.

[0047] The alkoxy group as the substituent of the hydrocarbon group is not particularly limited and may be a linear or branched (preferably linear) alkoxy group having 1 to 8 carbon atoms, preferably 1 to 5, and more preferably 1 to 3 carbon atoms, which may be substituted with a halogen atom (such as a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.). The number of substituents is not particularly limited and is, for example, preferably 0 to 6, more preferably 0 to 3, and even more preferably 0 to 1.

[0048] Examples of such an optionally substituted alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a perfluoromethoxy group, and a perfluoroethoxy group.

[0049] The halogen atom as a substituent of the above-mentioned hydrocarbon group is not particularly limited, and examples thereof include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0050] In the general formula (2), R 1 The perfluoroalkyl group represented by the formula (I) means an alkyl group in which all hydrogen atoms are substituted with fluorine atoms.

[0051] The perfluoroalkyl group may be any of linear, branched and cyclic. Among them, linear perfluoroalkyl groups are preferred from the viewpoints of the conversion rate of the reaction, the selectivity of the compound represented by the general formula (1), the yield of the compound represented by the general formula (1), etc.

[0052] The number of carbon atoms in this perfluoroalkyl group is not particularly limited, but from the viewpoints of the conversion rate of the reaction, the selectivity of the compound represented by general formula (1), the yield of the compound represented by general formula (1), etc., it is preferably 1 to 5, more preferably 1 to 4, and even more preferably 1 to 3.

[0053] Specific examples of such perfluoroalkyl groups include a trifluoromethyl group, a pentafluoroethyl group, and a heptafluoropropyl group.

[0054] In the general formula (2), X 1 The halogen atom other than a fluorine atom represented by the formula (I) is not particularly limited, and examples thereof include a chlorine atom, a bromine atom, and an iodine atom.

[0055] In the general formula (2), X 1 The number of substitutions, n, is not particularly limited, and is preferably 1 to 6 from the viewpoints of the conversion rate of the reaction, the selectivity of the compound represented by general formula (1), the yield of the compound represented by general formula (1), etc., and may also be 2 to 6, 3 to 6, 4 to 6, 5 to 6, etc.

[0056] When n, which is the number of substitutions of X, is 3 to 6, the compound represented by general formula (2) is represented by general formula (2A):

[0057] [ka]

[0058] [In the formula, R 1 and X 1 is the same as above. n represents an integer of 3 to 6. It is a compound represented by the formula:

[0059] Specific examples of the compound represented by the general formula (2) that satisfies the above conditions include

[0060] [ka]

[0061] [ka]

[0062] [ka]

[0063] etc.

[0064] The compound represented by the above general formula (2) may be a known or commercially available product. The compound represented by the above general formula (2) may be used alone or in combination of two or more kinds.

[0065] (1-2) Reaction In the reaction of the present disclosure, in the compound represented by the above general formula (2), X which is a halogen atom other than fluorine 1 However, in the presence of a specific phosphonium salt, these are fluorinated with a metal fluoride to replace the fluorine atom, thereby producing the compound represented by the above general formula (1).

[0066] In this case, X, which is a halogen atom other than fluorine, 1 When there are a plurality of fluorinated groups, that is, when n in general formula (2) is an integer of 2 or more, a compound in which two or more of the fluorinated groups (particularly all of the fluorinated groups) are fluorinated is selectively synthesized.

[0067] On the other hand, in the compound represented by the above general formula (2), R 1 remains unreacted even upon fluorination with a metal fluoride in the presence of a specific phosphonium salt.

[0068] As a result, a compound represented by general formula (1) is obtained.

[0069] The reaction of the first aspect of the present disclosure can be carried out in either a batch system in which the raw materials are charged into a reactor all at once, or a flow system in which the raw materials are continuously fed into a reactor while the product is withdrawn from the reactor. Since the reaction of the present disclosure is not a very fast reaction, it is preferable to use a batch system.

[0070] (1-3) Phosphonium salts The phosphonium salt used in the production method of the first embodiment of the present disclosure is a phosphonium salt having one or more alkyl groups.

[0071] The phosphonium salt is, for example, a compound represented by the general formula (3):

[0072] [ka]

[0073] [In the formula, R 3 , R 4 , R 5 and R 6 are the same or different and represent a hydrocarbon group. 3 , R 4 , R 5 and R 6 At least one of the groups is an alkyl group. Y represents a counter anion. Examples of the phosphonium salt include those represented by the following formula:

[0074] In the general formula (3), R 3 , R 4 , R 5 and R 6 The hydrocarbon group represented by R may be any of those mentioned above. The types and numbers of the substituents are also the same. 3 , R 4 , R 5 and R 6 is preferably the site at which a carbon atom bonds to the central phosphorus atom.

[0075] However, from the viewpoint of the conversion rate of the reaction, the selectivity of the compound represented by the general formula (1), the yield of the compound represented by the general formula (1), etc., R3 , R 4 , R 5 and R 6 At least one (one, two, three or four) of the is an alkyl group.

[0076] In addition, the selectivity of the compound represented by the general formula (1), the yield of the compound represented by the general formula (1) From the viewpoint of R 3 , R 4 , R 5 and R 6 As the alkyl group, an alkyl group is preferable. 3 , R 4 , R 5 and R 6 At least one (one, two, three or four) of the above is an alkyl group having 1 to 20 carbon atoms, preferably 3 to 15, more preferably 4 to 12, and even more preferably 5 to 10. In particular, by increasing the number of carbon atoms in the alkyl group of the phosphonium salt, it is possible to particularly improve the selectivity of the compound represented by general formula (1), the yield of the compound represented by general formula (1), and the like, and also to particularly reduce the amount of impurities produced.

[0077] In the general formula (3), the counter anion represented by Y is not particularly limited and various anions can be used. For example, a halide ion (fluoride ion (F - ), chloride ion (Cl - ), bromide ion (Br - ), iodide ion (I - ) etc.), tetrafluoroborate ion (BF4 - ), hydrogen sulfate ion (HSO4 - ), acetate ion (CHCOO - ), hexafluorophosphate ion (PF6 - ) etc.

[0078] Specific examples of the compound represented by the general formula (3) that satisfies the above conditions include

[0079] [ka]

[0080] [ka]

[0081] etc.

[0082] These phosphonium salts may be known or commercially available products. The above phosphonium salts may be used alone or in combination of two or more.

[0083] In the reaction in the production method according to the first embodiment of the present disclosure, the amount of the phosphonium salt used is not particularly limited, but from the viewpoints of the conversion rate of the reaction, the selectivity of the compound represented by general formula (1), the yield of the compound represented by general formula (1), etc., the amount is preferably 0.01 to 10 mol, more preferably 0.1 to 5 mol, and even more preferably 1 to 2.5 mol, relative to 1 mol of the compound represented by general formula (2). When multiple phosphonium salts are used, the total amount thereof should be within the above range. It is preferable to adjust so that

[0084] (1-4) Metal fluorides There are no particular limitations on the metal fluoride as long as it can fluorinate halogen atoms other than fluorine in the compound represented by the general formula (2). From the viewpoints of the conversion rate of the reaction, the selectivity of the compound represented by the general formula (1), the yield of the compound represented by the general formula (1), etc., an alkali metal or alkaline earth metal fluoride is preferred, and an alkali metal fluoride is more preferred. Therefore, examples of metals constituting metal fluorides include alkali metals such as lithium, sodium, potassium, cesium, etc., and alkaline earth metals such as magnesium, calcium, barium, etc. These metals can be used alone or in combination of two or more.

[0085] Specific examples of metal fluorides that satisfy such conditions include alkali metal fluorides such as lithium fluoride, sodium fluoride, potassium fluoride, and cesium fluoride; and alkaline earth metal fluorides such as magnesium fluoride, calcium fluoride, and barium fluoride. Among these, from the viewpoints of the conversion rate of the reaction, the selectivity of the compound represented by the general formula (1), and the yield of the compound represented by the general formula (1), alkali metal fluorides such as lithium fluoride, sodium fluoride, potassium fluoride, and cesium fluoride are preferred, and potassium fluoride is more preferred.

[0086] These metal fluorides may be publicly known or commercially available products. The above metal fluorides may be used alone or in combination of two or more kinds.

[0087] In the reaction in the production method according to the first embodiment of the present disclosure, the amount of metal fluoride used is not particularly limited, but is preferably 0.01 to 30 mol, more preferably 0.1 to 20 mol, and even more preferably 1 to 15 mol, relative to 1 mol of the compound represented by general formula (2) from the viewpoints of the conversion rate of the reaction, the selectivity of the compound represented by general formula (1), the yield of the compound represented by general formula (1), etc. When a plurality of metal fluorides are used, it is preferable to adjust the total amount thereof to be within the above range.

[0088] (1-5) Solvent The solvent used in the production method in the production method of the first aspect of the present disclosure is a solvent containing a nitrogen-containing organic compound, preferably a nitrogen-containing polar solvent, from the viewpoint of dissolving the compound represented by the general formula (2), phosphonium salt, metal fluoride, etc., and also being excellent in the conversion rate of the reaction, the selectivity of the compound represented by the general formula (1), the yield of the compound represented by the general formula (1), etc. Examples of such solvents include amide compounds (N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, N,N-diisopropylformamide, N-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, 1,3-dimethyl-3,4,5,6-tetrahydropyrimidinone, hexamethylphosphoric acid triamide, etc.), amine compounds (triethylamine, 1-methylpyrrolidine, etc.), pyridine compounds (pyridine, methylpyridine, etc.), quinoline compounds (quinoline, methylquinoline, etc.), etc. Among these, from the viewpoints of the conversion rate of the reaction, the selectivity of the compound represented by the general formula (1), the yield of the compound represented by the general formula (1), and the like, amide compounds, pyridine compounds, and the like are preferred, with N,N-dimethylformamide, N,N-diethylformamide, N,N-diisopropylformamide, N-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, 1,3-dimethyl-3,4,5,6-tetrahydropyrimidinone, hexamethylphosphoric acid triamide, pyridine, methylpyridine, and the like being more preferred, with N,N-dimethylformamide, N,N-diethylformamide, N,N-diisopropylformamide, N-methyl-2-pyrrolidone, pyridine, and the like being even more preferred, with N,N-dimethylformamide, N-methyl-2-pyrrolidone, pyridine, and the like being particularly preferred.

[0089] These solvents may be known or commercially available products. These solvents may be used alone or in combination of two or more.

[0090] The amount of the solvent used is not particularly limited as long as it is a solvent amount, and can be an excess amount. From the viewpoints of the conversion rate of the reaction, the selectivity of the compound represented by general formula (1), the yield of the compound represented by general formula (1), and the like, the amount is preferably 80 to 10,000 parts by mass, more preferably 100 to 1,000 parts by mass, and even more preferably 150 to 800 parts by mass, relative to 100 parts by mass of the compound represented by general formula (2).

[0091] (1-6) Reaction temperature In the reaction of the first aspect of the present disclosure, the reaction temperature can be set under mild conditions, and from the viewpoints of easily improving the conversion rate of the reaction, the yield and selectivity of the compound represented by general formula (1), and easily reducing by-products, the reaction temperature is usually preferably 0 to 400°C, more preferably 25 to 300°C, and even more preferably 50 to 200°C.

[0092] (1-7)Reaction time The reaction time (maintenance time at the maximum temperature) of the reaction of the first embodiment of the present disclosure can be set to a time during which the reaction can proceed sufficiently, and from the viewpoints of the conversion rate of the reaction, the selectivity of the compound represented by general formula (1), the yield of the compound represented by general formula (1), etc., the reaction time is preferably 1 minute to 48 hours, and more preferably 5 minutes to 24 hours.

[0093] (1-8) Reaction pressure The reaction pressure of the reaction in the first aspect of the present disclosure is preferably -2 to 2 MPa, more preferably -1 to 1 MPa, and even more preferably -0.5 to 0.5 MPa, from the viewpoints of the conversion rate of the reaction, the selectivity of the compound represented by general formula (1), the yield of the compound represented by general formula (1), etc. In the present disclosure, the pressure is a gauge pressure unless otherwise specified.

[0094] In the reaction of the first aspect of the present disclosure, the reactor in which the compound represented by the general formula (2) and the metal fluoride are reacted is not particularly limited in shape and structure as long as it can withstand the above-mentioned temperature and pressure. Examples of the reactor include a vertical reactor, a horizontal reactor, and a multi-tube reactor. Examples of the material of the reactor include glass, stainless steel, iron, nickel, and iron-nickel alloys.

[0095] (1-9) Reaction examples The atmosphere in which the reaction in the first embodiment of the present disclosure is carried out is preferably an inert gas atmosphere in order to prevent deterioration of the compound represented by general formula (2), the phosphonium salt, and the metal fluoride.

[0096] Examples of the inert gas include nitrogen, helium, argon, etc. Among these inert gases, nitrogen is preferred from the viewpoint of reducing costs.

[0097] In the production method according to the first embodiment of the present disclosure, the amount of water in the system is preferably 700 mass ppm or less, more preferably 0.1 to 650 mass ppm, further preferably 1 to 600 mass ppm, and particularly preferably 10 to 500 mass ppm, from the viewpoints of the conversion rate of the reaction, the selectivity of the compound represented by the general formula (1), the yield of the compound represented by the general formula (1), and the like. The amount of water in the system means the total amount of water contained in the reaction system, with the total amount of the reagents (the compound represented by the general formula (2), the phosphonium salt, the metal fluoride, the solvent, etc.) used in the reaction being taken as 100 mass%. In addition, water can be added to the reaction system to adjust the amount of water in the system. In the present disclosure, the amount of water in the system is measured by a Karl Fischer moisture meter.

[0098] After completion of the reaction, purification treatment can be carried out according to a conventional method, if necessary, to obtain the compound represented by the general formula (1).

[0099] (1-10) Target compound (general formula (1)) The target compound thus produced has the general formula (1):

[0100] [ka]

[0101] [In the formula, R 1 represents a hydrogen atom, a hydroxyl group, a fluorine atom, a cyano group, a nitro group, a hydrocarbon group, or a perfluoroalkyl group. 1are the same or different and represent a halogen atom other than a fluorine atom. n represents an integer of 1 to 6. n1 represents an integer of 1 to 6. However, when n≧n1 and n is an integer of 2 to 6, n1 represents an integer of 2 to 6.] It is a compound represented by the formula:

[0102] In the general formula (1), R 1 , X 1 and n are as defined above. However, X in the general formula (1) 1 Since the number of is n-n1, n ≥ n1. Also, if n is an integer of 2 or more, there are 2 or more X 1 is preferably fluorinated, and therefore when n is an integer of 2 to 6, n1 is an integer of 2 to 6.

[0103] That is, the target compound produced in the present disclosure, which is represented by the general formula (1), is specifically:

[0104] [ka]

[0105] [ka]

[0106] [ka]

[0107] etc.

[0108] 2. Method for producing fluorine-containing aromatic compounds (part 2) The production method according to the second embodiment of the present disclosure includes a method for producing a compound represented by general formula (1A):

[0109] [ka]

[0110] [In the formula, R 1represents a hydrogen atom, a hydroxyl group, a fluorine atom, a cyano group, a nitro group, a hydrocarbon group, or a perfluoroalkyl group. 1 are the same or different and are halogen atoms other than fluorine atoms. n is an integer from 3 to 6. n1 is an integer from 2 to 6, provided that n ≧ n1. A method for producing a compound represented by the following formula: In the presence of a phosphonium salt having one or more alkyl groups, General formula (2):

[0111] [ka]

[0112] [In the formula, R 1 , X 1 and n is the same as above.] A compound represented by the formula: React with metal fluoride to produce two or more X 1 to produce a compound represented by the general formula (1A). Equipped with.

[0113] (2-1) Starting compound (general formula (2A)) In a second aspect of the present disclosure, the compound represented by general formula (2A) is represented by the general formula (2A):

[0114] [ka]

[0115] [In the formula, R 1 represents a hydrogen atom, a hydroxyl group, a fluorine atom, a cyano group, a nitro group, a hydrocarbon group, or a perfluoroalkyl group. 1 are the same or different and represent a halogen atom other than a fluorine atom. n represents an integer of 3 to 6. It is a compound represented by the formula:

[0116] In general formula (2A), R 1Hydrocarbon groups and perfluoroalkyl groups represented by the following formula: X 1 Examples of halogen atoms other than fluorine atoms represented by the formula (1-1) include R 1 Hydrocarbon groups and perfluoroalkyl groups represented by the following formula: X 1 The preferred types and specific examples of halogen atoms other than fluorine atoms can be adopted.

[0117] In the general formula (2A), X 1 The substitution number n is 3 to 6, and can also be 4 to 6, 5 to 6, etc., from the viewpoints of the conversion rate of the reaction, the selectivity of the compound represented by general formula (1A), the yield of the compound represented by general formula (1A), etc.

[0118] Specific examples of the compound represented by the general formula (2A) that satisfies the above conditions include

[0119] [ka]

[0120] [ka]

[0121] etc.

[0122] (2-2) Reaction, phosphonium salt, metal fluoride, solvent, reaction temperature, reaction time, reaction pressure and reaction examples For the reaction in the second embodiment of the present disclosure, the explanation for "Reaction (1-2)" above can be adopted.

[0123] In the second embodiment of the present disclosure, the phosphonium salt may adopt the above description of "(1-3) phosphonium salt". The preferred types and specific examples are also the same.

[0124] In the second embodiment of the present disclosure, the metal fluoride may adopt the explanation of "(1-4) Metal fluoride" above. The preferred types and specific examples are also the same.

[0125] In the second aspect of the present disclosure, the solvent may be the same as that described above in "(2-2) Solvent." The same also applies to preferred types and specific examples.

[0126] In the second embodiment of the present disclosure, the reaction temperature may be the same as that described above in "(1-6) Reaction temperature." The preferred range is also the same.

[0127] In the second embodiment of the present disclosure, the reaction time may be the same as that described above in "(1-7) Reaction time." The preferred range is also the same.

[0128] In the second embodiment of the present disclosure, the reaction pressure may be the same as that described in the above "(1-8) Reaction Pressure." The preferred types and specific examples are also the same.

[0129] In the second aspect of the present disclosure, examples of the reaction may be those described in the above "(1-9) Examples of the reaction". The same also applies to preferred types and specific examples.

[0130] (2-3) Solvent The solvent used in the production method in the second aspect of the present disclosure is not particularly limited, but is preferably a polar organic solvent, which dissolves the compound represented by general formula (2A), phosphonium salt, metal fluoride, etc., and is excellent in the conversion rate of the reaction, the selectivity of the compound represented by general formula (1A), the yield of the compound represented by general formula (1A), etc. Furthermore, a solvent containing a nitrogen-containing organic compound, preferably a nitrogen-containing polar solvent, is more preferable, from the viewpoint of dissolving the compound represented by general formula (2A), phosphonium salt, metal fluoride, etc., and is excellent in the conversion rate of the reaction, the selectivity of the compound represented by general formula (1A), the yield of the compound represented by general formula (1A), etc. Examples of such solvents include amide compounds (N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, N,N-diisopropylformamide, N-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, 1,3-dimethyl-3,4,5,6-tetrahydropyrimidinone, hexamethylphosphoric acid triamide, etc.), amine compounds (triethylamine, 1-methylpyrrolidine, etc.), pyridine compounds (pyridine, methylpyridine, etc.), quinoline compounds (quinoline, methylquinoline, etc.), and the like. Among these, from the viewpoints of the conversion rate of the reaction, the selectivity of the compound represented by general formula (1A), the yield of the compound represented by general formula (1A), and the like, amide compounds, pyridine compounds, and the like are preferred, and N,N-dimethylformamide, N,N-diethylformamide, N,N-diisopropylformamide, N-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, 1,3-dimethyl-3,4,5,6-tetrahydropyrimidinone, hexamethylphosphoric acid triamide, pyridine, methylpyridine, and the like are more preferred, and N,N-dimethylformamide, N,N-diethylformamide, N,N-diisopropylformamide, N-methyl-2-pyrrolidone, pyridine, and the like are further preferred, and N,N-dimethylformamide, N-methyl-2-pyrrolidone, pyridine, and the like are particularly preferred.

[0131] These solvents may be known or commercially available products. These solvents may be used alone or in combination of two or more.

[0132] The amount of the solvent used is not particularly limited as long as it is a solvent amount, and can be an excess amount. From the viewpoints of the conversion rate of the reaction, the selectivity of the compound represented by general formula (1A), the yield of the compound represented by general formula (1A), and the like, the amount is preferably 80 to 10,000 parts by mass, more preferably 100 to 1,000 parts by mass, and even more preferably 150 to 800 parts by mass, relative to 100 parts by mass of the compound represented by general formula (2A).

[0133] (2-4) Target compound (general formula (1A)) The target compound thus produced has the general formula (1A):

[0134] [ka]

[0135] [In the formula, R 1 represents a hydrogen atom, a hydroxyl group, a fluorine atom, a cyano group, a nitro group, a hydrocarbon group, or a perfluoroalkyl group. 1 are the same or different and represent a halogen atom other than a fluorine atom. n represents an integer of 3 to 6. n1 represents an integer of 2 to 6, with the proviso that n ≧ n1. It is a compound represented by the formula:

[0136] In general formula (1A), R 1 , X 1 and n1 are as described above. However, X in the general formula (1) 1 Since the number of elements is n-n1, it follows that n≧n1.

[0137] That is, the target compound produced in the present disclosure, which is represented by general formula (1A), is specifically:

[0138] [ka]

[0139] [ka]

[0140] etc.

[0141] 3. Method for producing fluorine-containing aromatic compounds (part 3) The production method according to the third aspect of the present disclosure includes a method for producing a compound represented by general formula (1):

[0142] [ka]

[0143] [In the formula, R 1 represents a hydrogen atom, a hydroxyl group, a fluorine atom, a cyano group, a nitro group, a hydrocarbon group, or a perfluoroalkyl group. 1 are the same or different and represent a halogen atom other than a fluorine atom. n represents an integer of 1 to 6. n1 represents an integer of 1 to 6. However, when n≧n1 and n is an integer of 2 to 6, n1 represents an integer of 2 to 6.] A method for producing a compound represented by the following formula: In the presence of a phosphonium salt having one or more alkyl groups having 3 or more carbon atoms, General formula (2):

[0144] [ka]

[0145] [In the formula, R 1 , X 1 and n is the same as above.] A compound represented by the formula: When n is an integer of 2 or more, two or more X are reacted with the metal fluoride. 1 to produce a compound represented by the general formula (1). Equipped with.

[0146] (3-1) Starting compound (general formula (2)), reaction, metal fluoride, solvent, reaction temperature, reaction time, reaction pressure and target compound In the third aspect of the present disclosure, the compound represented by general formula (2) which is the starting compound can adopt the explanation of "(1-1) Starting compound (general formula (2))" above. The preferred types and specific examples are also the same.

[0147] For the reaction in the third embodiment of the present disclosure, the explanation for "Reaction (1-2)" above can be adopted.

[0148] In the third embodiment of the present disclosure, the metal fluoride may adopt the explanation of "(1-4) Metal fluoride" above. The preferred types and specific examples are also the same.

[0149] In the third aspect of the present disclosure, the solvent may be the same as that described above in "(2-3) Solvent." The same also applies to preferred types and specific examples.

[0150] In the third embodiment of the present disclosure, the reaction temperature may be the same as that described above in "(1-6) Reaction temperature." The preferred range is also the same.

[0151] In the third aspect of the present disclosure, the reaction time may be the same as that described above in "(1-7) Reaction time." The preferred range is also the same.

[0152] In the third aspect of the present disclosure, the reaction pressure may be the same as that described in the above "(1-8) Reaction Pressure." The preferred types and specific examples are also the same.

[0153] In the third aspect of the present disclosure, examples of the reaction may be those described in the above "(1-9) Examples of the reaction". The same also applies to preferred types and specific examples.

[0154] In the third aspect of the present disclosure, the compound represented by general formula (1) which is the target compound can adopt the explanation of "(1-10) Target compound (general formula (1))" above. The preferred types and specific examples are also the same.

[0155] (3-2) Phosphonium salts The phosphonium salt used in the third embodiment of the present disclosure is a phosphonium salt having one or more alkyl groups having 3 or more carbon atoms.

[0156] The phosphonium salt can be, for example, a compound represented by the general formula (3A):

[0157] [ka]

[0158] [In the formula, R 3a , R 4a , R 5a and R 6a are the same or different and represent a hydrocarbon group. 3a , R 4a , R 5a and R 6a At least one of the groups is an alkyl group having 3 or more carbon atoms. Y represents a counter anion. Examples of the phosphonium salt include those represented by the following formula:

[0159] In general formula (3A), R 3a , R 4a , R 5a and R 6a The hydrocarbon group represented by R may be any of those mentioned above. The types and numbers of the substituents are also the same. 3a , R 4a , R 5a and R 6a is preferably the site at which a carbon atom bonds to the central phosphorus atom.

[0160] However, from the viewpoint of the conversion rate of the reaction, the selectivity of the compound represented by the general formula (1), the yield of the compound represented by the general formula (1), etc., R 3a , R 4a , R 5a and R 6a At least one (one, two, three or four) of these is an alkyl group having three or more carbon atoms.

[0161] In addition, from the viewpoint of the selectivity of the compound represented by the general formula (1), the yield of the compound represented by the general formula (1), etc., R3a , R 4a , R 5a and R 6a As the alkyl group, an alkyl group is preferable. 3a , R 4a , R 5a and R 6a At least one (one, two, three, or four) of the above is an alkyl group having 3 or more carbon atoms, preferably 4 to 20, and more preferably 5 to 15. In particular, by increasing the number of carbon atoms in the alkyl group of the phosphonium salt, the selectivity of the compound represented by general formula (1), the yield of the compound represented by general formula (1), and the like can be particularly improved, and the amount of impurities produced can be particularly reduced.

[0162] In the general formula (3A), as the counter anion represented by Y, those mentioned above can be used.

[0163] Specific examples of the compound represented by the general formula (3A) that satisfies the above conditions include

[0164] [ka]

[0165] etc.

[0166] These phosphonium salts may be known or commercially available products. The above phosphonium salts may be used alone or in combination of two or more.

[0167] In the reaction in the third aspect of the present disclosure, the amount of the phosphonium salt used is not particularly limited, but from the viewpoints of the conversion rate of the reaction, the selectivity of the compound represented by general formula (1), the yield of the compound represented by general formula (1), and the like, the amount is preferably 0.01 to 10 mol, more preferably 0.1 to 5 mol, and even more preferably 1 to 2.5 mol, relative to 1 mol of the compound represented by general formula (2). When a plurality of phosphonium salts are used, it is preferable to adjust the total amount thereof to be within the above range.

[0168] 4. Composition (part 1) In the manner described above, the compound represented by the general formula (1) can be obtained. The compound represented by the general formula (1) can be obtained by using difluorobenzotrifluoride and X in the general formula (2). 1 and at least one halogenated fluorobenzotrifluoride selected from the group consisting of chlorofluorobenzotrifluoride, bromofluorobenzotrifluoride and iodofluorobenzotrifluoride as a compound in which only a portion of the above is fluorinated.

[0169] The difluorobenzotrifluoride as the compound represented by the general formula (1) is not particularly limited, and examples thereof include 2,3-difluorobenzotrifluoride, 2,4-difluorobenzotrifluoride, 2,6-difluorobenzotrifluoride, etc. These difluorobenzotrifluorides can be used alone or in combination of two or more kinds.

[0170] X in general formula (2) 1As a compound in which only a part of the above is fluorinated, the halogenated fluorobenzotrifluoride is not particularly limited, and examples thereof include 2-chloro-3-fluorobenzotrifluoride, 2-chloro-4-fluorobenzotrifluoride, 2-chloro-6-fluorobenzotrifluoride, 3-chloro-2-fluorobenzotrifluoride, 4-chloro-2-fluorobenzotrifluoride, 6-chloro-2-fluorobenzotrifluoride, 2-bromo-3-fluorobenzotrifluoride, 2-bromo-4-fluorobenzotrifluoride, Examples of the halogenated fluorobenzotrifluoride include 2-bromo-6-fluorobenzotrifluoride, 3-bromo-2-fluorobenzotrifluoride, 4-bromo-2-fluorobenzotrifluoride, 6-bromo-2-fluorobenzotrifluoride, 2-iodo-3-fluorobenzotrifluoride, 2-iodo-4-fluorobenzotrifluoride, 2-iodo-6-fluorobenzotrifluoride, 3-iodo-2-fluorobenzotrifluoride, 4-iodo-2-fluorobenzotrifluoride, and 6-iodo-2-fluorobenzotrifluoride. These halogenated fluorobenzotrifluorides can be used alone or in combination of two or more.

[0171] With the total amount of the composition of the present disclosure related to the first aspect being 100 mol%, the content of difluorobenzotrifluoride is 60.0 to 99.9 mol%, and can also be 65.0 to 99.5 mol%, 70.0 to 99.0 mol%, 75.0 to 98.5 mol%, 80.0 to 98.0 mol%, 85.0 to 97.5 mol%, 90.0 to 97.0 mol%, etc.

[0172] Furthermore, with the total amount of the composition of the present disclosure relating to the first aspect being 100 mol %, the amount of halogenated fluorobenzotrifluoride is 0.1 to 40.0 mol %, and it can also be 0.5 to 35.0 mol %, 1.0 to 30.0 mol %, 1.5 to 25.0 mol %, 2.0 to 20.0 mol %, 2.5 to 15.0 mol %, 3.0 to 10.0 mol %, etc.

[0173] The composition of the present disclosure according to the first aspect can be effectively used for various applications such as a solvent for organic synthesis, an intermediate for agricultural chemicals, and an intermediate for pharmaceuticals.

[0174] 5. Composition (part 2) In the manner described above, the compound represented by the general formula (1) can be obtained. The compound represented by the general formula (1) is pentafluorobenzotrifluoride, and the compound represented by the general formula (2) is X 1 The partially fluorinated compounds are chlorotetrafluorobenzotrifluoride, bromotetrafluorobenzotrifluoride, and iodotetrafluorobenzotrifluoride. and at least one halogenated fluorobenzotrifluoride selected from the group consisting of dichlorotrifluorobenzotrifluoride, dibromotrifluorobenzotrifluoride, diiodotrifluorobenzotrifluoride, trichlorodifluorobenzotrifluoride, tribromodifluorobenzotrifluoride, triiododifluorobenzotrifluoride, tetrachlorofluorobenzotrifluoride, tetrabromofluorobenzotrifluoride, and tetraiodofluorobenzotrifluoride.

[0175] The pentafluorobenzotrifluoride represented by the general formula (1) is not particularly limited, and may be 2,3,4,5,6-pentafluorobenzotrifluoride. Pentafluorobenzotrifluorides may be used alone or in combination of two or more.

[0176] X in general formula (2) 1 As the halogenated fluorobenzotrifluoride, which is a compound in which only a portion of the above is fluorinated, any of the isotopes can be used. The halogenated fluorobenzotrifluorides can be used alone or in combination of two or more kinds.

[0177] With the total amount of the composition of the present disclosure relating to the second embodiment being 100 mol %, the content of pentafluorobenzotrifluoride is 60.0 to 99.9 mol %, and can also be 65.0 to 99.5 mol %, 70.0 to 99.0 mol %, 75.0 to 98.5 mol %, 80.0 to 98.0 mol %, 85.0 to 97.5 mol %, 90.0 to 97.0 mol %, etc.

[0178] Furthermore, with the total amount of the composition of the present disclosure relating to the second aspect being 100 mol %, the amount of halogenated fluorobenzotrifluoride is 0.1 to 40.0 mol %, and it can also be 0.5 to 35.0 mol %, 1.0 to 30.0 mol %, 1.5 to 25.0 mol %, 2.0 to 20.0 mol %, 2.5 to 15.0 mol %, 3.0 to 10.0 mol %, etc.

[0179] The composition according to the second aspect of the present disclosure can be effectively used in various applications such as etching gas and cleaning gas.

[0180] Although the embodiment of the present disclosure has been described above, various changes in form and details are possible without departing from the spirit and scope of the claims. EXAMPLES

[0181] The following examples will clarify the features of the present disclosure, but the present disclosure is not limited to these examples.

[0182] In each of the Examples and Comparative Examples, the water content was measured with a Karl Fischer moisture meter at the start of the reaction.

[0183] Examples 1 to 7 and Comparative Examples 1 to 3 2,4-Dichlorobenzotrifluoride (1 g, 0.005 mol), potassium fluoride (0.8 g, 0.014 mol), 4.5 mL of a solvent (N-methyl-2-pyrrolidone (NMP) or sulfolane), and a phosphonium salt (0.0014 mol) shown in Table 1 were added to an autoclave, which was then covered and heated to 200° C. to allow the reaction to proceed for 24 hours.

[0184] After the reaction was completed, mass analysis was performed by gas chromatography and GCMS (gas chromatography mass spectrometry), and structural analysis was performed by NMR (nuclear magnetic resonance).

[0185] The results of mass spectrometry and structural analysis confirmed that 2,4-difluorobenzotrifluoride was produced as the target compound.

[0186] The results are shown in Table 1.

[0187] In Table 1, the phosphonium salts used are as follows:

[0188] [ka]

[0189] In Table 1, the product 2,4-2F-BTF means 2,4-difluorobenzotrifluoride, and 2,4-Cl-F-BTF means 2-chloro-4-fluorobenzotrifluoride. In Table 1, the selectivity of 2,4-Cl-F-BTF means the total selectivity of 2-chloro-4-fluorobenzotrifluoride and 4-chloro-2-fluorobenzotrifluoride.

[0190] [Table 1]

[0191] Examples 8 to 13 Reactions were carried out in the same manner as in Examples 1 to 7, except that the substrates (0.005 mol) shown in Tables 2 to 4 and the phosphonium salts (0.0014 mol) shown in Tables 2 to 4 were used instead of 2,4-dichlorobenzotrifluoride.

[0192] From the results of mass spectrometry and structural analysis, it was confirmed that difluorobenzotrifluoride or pentafluorobenzotrifluoride was produced as the target substance.

[0193] The results are shown in Tables 2 to 4.

[0194] In addition, in Tables 2 to 4, the substrate 2,3-2Cl-BTF means 2,3-dichlorobenzotrifluoride, 2,6-2Cl-BTF means 2,6-dichlorobenzotrifluoride, and 5Cl-BTF means 2,3,4,5,6-pentachlorobenzotrifluoride.

[0195] In addition, the phosphonium salts used in Tables 2 to 4 are as follows.

[0196] [ka]

[0197] In addition, in Tables 2 to 4, the product 2,3-2F-BTF means 2,3-difluorobenzotrifluoride, 2,3-Cl-F-BTF means 2-chloro-3-fluorobenzotrifluoride and / or 3-chloro-2-fluorobenzotrifluoride, 2,6-2F-BTF means 2,6-difluorobenzotrifluoride, 2,6-Cl-F-BTF means 2-chloro-6-fluorobenzotrifluoride, and 5F-BTF means 2,3,4,5,6-pentafluorobenzotrifluoride. 4F,1Cl-BTF means chlorotetrafluorobenzotrifluoride (including all isotopes), 3F,2Cl-BTF means dichlorotrifluorobenzotrifluoride (including all isotopes), 2F,3Cl-BTF means trichlorodifluorobenzotrifluoride (including all isotopes), and 1F,4Cl-BTF means tetrachlorofluorobenzotrifluoride (including all isotopes). In addition, in Tables 2 to 4, the selectivity of 2,3-Cl-F-BTF means the total selectivity of 2-chloro-3-fluorobenzotrifluoride and 3-chloro-2-fluorobenzotrifluoride, the selectivity of 4F,1Cl-BTF means the total selectivity of isotopes of chlorotetrafluorobenzotrifluoride, the selectivity of 3F,2Cl-BTF means the total selectivity of isotopes of dichlorotrifluorobenzotrifluoride, the selectivity of 2F,3Cl-BTF means the total selectivity of trichlorodifluorobenzotrifluoride, and the selectivity of 1F,4Cl-BTF means the total selectivity of tetrachlorofluorobenzotrifluoride.

[0198] [Table 2]

[0199] [Table 3]

[0200] [Table 4]

Claims

1. A composition comprising 2,4-difluorobenzotrifluoride and / or 2,6-difluorobenzotrifluoride and at least one halogenated fluorobenzotrifluoride selected from the group consisting of chlorofluorobenzotrifluoride, bromofluorobenzotrifluoride and iodofluorobenzotrifluoride, The composition, wherein the content of the 2,4-difluorobenzotrifluoride and / or 2,6-difluorobenzotrifluoride is 80.0 to 99.9 mol % and the content of the halogenated fluorobenzotrifluoride is 0.1 to 20.0 mol %, based on the total amount of the composition being 100 mol %.

2. The composition according to claim 1, which is used as a solvent for organic synthesis, an agricultural chemical intermediate, or a pharmaceutical intermediate.

3. A composition comprising pentafluorobenzotrifluoride and at least one halogenated fluorobenzotrifluoride selected from the group consisting of chlorotetrafluorobenzotrifluoride, bromotetrafluorobenzotrifluoride, iodotetrafluorobenzotrifluoride, dichlorotrifluorobenzotrifluoride, dibromotrifluorobenzotrifluoride, diiodotrifluorobenzotrifluoride, trichlorodifluorobenzotrifluoride, tribromodifluorobenzotrifluoride, triiododifluorobenzotrifluoride, tetrachlorofluorobenzotrifluoride, tetrabromofluorobenzotrifluoride, and tetraiodofluorobenzotrifluoride, The content of the pentafluorobenzotrifluoride is 93.7 to 99.9 mol % based on the total amount of the composition being 100 mol %.

4. The composition according to claim 3, wherein the content of the halogenated fluorobenzotrifluoride is 0.1 to 6.0 mol % based on the total amount of the composition being 100 mol %.

5. The composition according to claim 3 or 4, which is used as an etching gas or a cleaning gas.

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