Method for producing imidic acid or imidic acid salt

Abstract

A novel method for producing an imidic acid or an imidic acid salt having a phosphoryl group is provided by a method for producing an imidic acid or an imidic acid salt represented by general formula [1], said method comprising a reaction step for reacting a phosphoryl isocyanate represented by general formula [2] with a compound represented by general formula [3]. # imgabs0 #

Description

Technical Field

[0001] The present disclosure relates to a method for producing various imidic acids or imidic acid salts having a phosphoryl group. Background Art

[0002] In recent years, various imide acids having a phosphoryl group, such as bis(phosphoryl)imide (HN(POX2)2), asymmetric phosphoryl imide (HN(POX2)(SO2X), and their metal salts and onium salts are known to be useful substances as ion conductive materials, anion sources for ionic liquids, electrolytes for non-aqueous electrolyte batteries such as lithium ion batteries, lithium batteries, lithium ion capacitors, sodium ion batteries, and additives.

[0003] Regarding the method for producing a bis(phosphoryl)imidic acid compound, Patent Document 1 describes a method for obtaining a bis(halogenated phosphoryl)imidic acid compound by reacting a phosphoryl halide with ammonia in the presence of an organic base (the following reaction formula: (1)).

[0004] [Chemistry 1]

[0005] (1)

[0006] In addition, Non-Patent Document 1 describes a method for obtaining lithium bis(difluorophosphoryl)imide by reacting LiN(SiMe3)2 as a silazane metal compound with phosphorus oxyfluoride (POF3) (the following reaction formula: (2)).

[0007] [Chemistry 2]

[0008] (2)2 POF2+LiN(SiMe3)2→LiN(POF2)2+2 Me3SiF

[0009] Patent Document 2 describes a method for obtaining an asymmetric phosphoryl imide by reacting a silazane derivative containing a sulfonyl group with phosphorus oxychloride (the following reaction formula: (3)).

[0010] [Chemistry 3]

[0011] (3)K[CF3SO2NSiMe3]POCl3→K[CF3SO2NPOCl2]+Me3SiCl

[0012] Prior art literature

[0013] Patent Literature

[0014] Patent Document 1: Japanese Patent Application Publication No. 2010-254554

[0015] Patent document 2: Chinese patent publication number CN102617414A

[0016] Non-patent literature

[0017] Non-patent document 1: Z. Anorg. Allg. Chem. 412 (1), 65-70 (1975) Summary of the invention

[0018] Problem that the invention aims to solve

[0019] The present disclosure aims to provide a novel method for producing an imidic acid or an imidic acid salt having a phosphoryl group.

[0020] Solutions for solving problems

[0021] The present inventors have found a novel production method for obtaining an imidic acid or an imidic acid salt having a phosphoryl group represented by the general formula [1] or [4] described below, and have completed the present disclosure. [1]

[0023] A method for producing an imidic acid or an imidic acid salt represented by the following general formula [1] comprises the following reaction steps:

[0024] The phosphoryl isocyanate represented by the following general formula [2] is reacted with the compound represented by the following general formula [3].

[0025] (Hereinafter, this production method may be referred to as "Invention 1".)

[0026] [Chemistry 4]

[0027]

[0028] In the general formula [1], X 1 , X 2 Each is independently a chlorine atom, a fluorine atom, an organic group selected from a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms and an aryloxy group having 6 to 10 carbon atoms, and at least one selected from a fluorine atom, an oxygen atom, a nitrogen atom and an unsaturated bond may also be present in the organic group.

[0029] Z is -P(=O)-, -S(=O)2- or -C(=O)-. When Z is -P(=O)-, a is 1, and when Z is -S(=O)2- or -C(=O)-, a is 0.

[0030] R 1 , R 2Each of them is independently a chlorine atom, a fluorine atom, an organic group selected from a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkyloxy group having 3 to 10 carbon atoms, a cycloalkenyl group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms and an aryloxy group having 6 to 10 carbon atoms, and at least one selected from a fluorine atom, an oxygen atom and an unsaturated bond may be present in the organic group.

[0031] M is a proton, an alkali metal cation, an alkaline earth metal cation or an onium cation, and m represents an integer having the same valence as the corresponding cation.]

[0032] [Chemistry 5]

[0033]

[0034] [In general formula [2], X 1 , X 2 Same as general formula [1].

[0035] [Chemistry 6]

[0036]

[0037] [In the general formula [3], Z is -P(=O)-, -S(=O)2- or -C(=O)-.

[0038] When Z is -P(=O)-, a is 1.

[0039] When Z is -S(=O)2-, a is 0.

[0040] When Z is -C(=O)-, a is 0.

[0041] R 1 , R 2 Each of them is independently a chlorine atom, a fluorine atom, an organic group selected from a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkyloxy group having 3 to 10 carbon atoms, a cycloalkenyl group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms and an aryloxy group having 6 to 10 carbon atoms, and at least one selected from a fluorine atom, an oxygen atom and an unsaturated bond may be present in the organic group.

[0042] M is a proton, an alkali metal cation, an alkaline earth metal cation or an onium cation, and m represents an integer having the same valence as the corresponding cation.] [2]

[0044] A method for producing an imidic acid or an imidic acid salt according to [1], wherein the amount of the phosphoryl isocyanate represented by the general formula [2] used is 0.1 to 10 mol relative to 1 mol of the compound represented by the general formula [3] (hereinafter, sometimes described as "[2] / [3] molar ratio is 0.1 to 10" etc.). [3]

[0046] The method for producing an imidic acid or an imidic acid salt according to [1] or [2], wherein the reaction temperature in the reaction step is -20 to 200°C. [4]

[0048] The method for producing an imidic acid or an imidic acid salt according to any one of [1] to [3], wherein the reaction step is performed in a reaction solvent. [5]

[0050] The method for producing an imidic acid or an imidic acid salt according to [4], wherein the reaction solvent is at least one solvent selected from the group consisting of nitriles, chain ethers, cyclic ethers, chain esters, cyclic esters, chain carbonates, cyclic carbonates and sulfur-containing solvents. [6]

[0052] The method for producing an imidic acid or an imidic acid salt according to any one of [1] to [5], wherein the M m+ It is a proton, a lithium ion, a sodium ion, a potassium ion, a trialkylammonium ion or a tetraalkylammonium ion. [7]

[0054] The method for producing an imidic acid or an imidic acid salt according to any one of [1] to [6], wherein the X 1 , X 2 Each is independently a group selected from a chlorine atom, a fluorine atom, a methyl group, a trifluoromethyl group, a phenyl group, a fluorophenyl group, a vinyl group, a thienyl group and a pyridyl group. [8]

[0056] The method for producing an imidic acid or an imidic acid salt according to any one of [1] to [7], wherein the reaction liquid after the reaction step is degassed and concentrated.

[0057] It should be noted that "degassing and concentrating" refers to the following method: the gas phase containing the volatile components from the above-mentioned reaction solution is depressurized, or a carrier gas substantially free of water such as nitrogen, argon, or dry air is circulated, so that the volatile components are discharged outside the system, thereby increasing the concentration of the solute in the reaction solution. The lower limit temperature during degassing and concentrating can be set to -20°C or 10°C. The upper limit temperature during degassing and concentrating can be set to 90°C or 60°C. If the temperature during degassing and concentrating is above -20°C, the concentration efficiency is high. In addition, if it is below 90°C, the reaction solution is not easy to color.

[0058] The "degassing and concentration" of the invention 2 described later is also the same as described above. [9]

[0060] A method for producing an imidic acid or an imidic acid salt represented by the following general formula [4] comprises the following reaction steps:

[0061] A sulfonyl isocyanate represented by the following general formula [5] is reacted with a compound represented by the following general formula [6].

[0062] (Hereinafter, this production method may be referred to as "Invention 2".)

[0063] [Chemistry 7]

[0064]

[0065] [In general formula [4], X 1 , X 2 Each is independently a chlorine atom, a fluorine atom, an organic group selected from a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms and an aryloxy group having 6 to 10 carbon atoms, and at least one selected from a fluorine atom, an oxygen atom, a nitrogen atom and an unsaturated bond may also be present in the organic group.

[0066] R 1 The organic group is a chlorine atom, a fluorine atom, an organic group selected from a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkyloxy group having 3 to 10 carbon atoms, a cycloalkenyl group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms and an aryloxy group having 6 to 10 carbon atoms, and at least one selected from a fluorine atom, an oxygen atom and an unsaturated bond may be present in the organic group.

[0067] M is a proton, an alkali metal cation, an alkaline earth metal cation or an onium cation, and m represents an integer having the same valence as the corresponding cation.]

[0068] [Chemistry 8]

[0069]

[0070] [In general formula [5], R 1 is a chlorine atom, a fluorine atom, an organic group selected from a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkyloxy group having 3 to 10 carbon atoms, a cycloalkenyl group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms, and at least one selected from a fluorine atom, an oxygen atom, and an unsaturated bond may also be present in the organic group.]

[0071] [Chemistry 9]

[0072]

[0073] [In general formula [6], X 1 , X 2 Each is independently a chlorine atom, a fluorine atom, an organic group selected from a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms and an aryloxy group having 6 to 10 carbon atoms, and at least one selected from a fluorine atom, an oxygen atom, a nitrogen atom and an unsaturated bond may also be present in the organic group.

[0074] M is a proton, an alkali metal cation, an alkaline earth metal cation or an onium cation, and m represents an integer having the same valence as the corresponding cation.]

[10]

[0076] A method for producing an imidic acid or an imidic acid salt according to [9], wherein the amount of the sulfonyl isocyanate represented by the general formula [5] used is 0.1 to 10 mol relative to 1 mol of the compound represented by the general formula [6] (hereinafter, sometimes described as "[5] / [6] molar ratio is 0.1 to 10" etc.).

[11]

[0078] The method for producing an imidic acid or an imidic acid salt according to [9] or

[10] , wherein the reaction temperature in the reaction step is 0 to 150°C.

[12]

[0080] The method for producing an imidic acid or an imidic acid salt according to any one of [9] to

[11] , wherein the reaction step is performed in a reaction solvent.

[13]

[0082] The method for producing an imidic acid or an imidic acid salt according to

[12] , wherein the reaction solvent is at least one solvent selected from the group consisting of nitriles, chain ethers, cyclic ethers, chain esters, cyclic esters, chain carbonates, cyclic carbonates and sulfur-containing solvents.

[14]

[0084] The method for producing an imidic acid or an imidic acid salt according to any one of [9] to

[13] , wherein the M m+ It is a proton, a lithium ion, a sodium ion, a potassium ion, a trialkylammonium ion or a tetraalkylammonium ion.

[15]

[0086] The method for producing an imidic acid or an imidic acid salt according to any one of [9] to

[14] , wherein the X 1 , X 2 Each is independently a group selected from a chlorine atom, a fluorine atom, a methyl group, a trifluoromethyl group, a phenyl group, a fluorophenyl group, a vinyl group, a thienyl group and a pyridyl group.

[16]

[0088] The method for producing an imidic acid or an imidic acid salt according to any one of [9] to

[15] , wherein the reaction liquid after the reaction step is degassed and concentrated.

[0089] In the production method disclosed herein, when obtaining the imidic acid or imidic acid salt having a phosphoryl group represented by the general formula [1] or [4], solid byproducts are not easily generated, and carbon dioxide is produced as a byproduct. Carbon dioxide is a gas at normal temperature and pressure, and is easily separated from the reaction solution. In addition, no special treatment is required for the separated carbon dioxide. Therefore, the production method disclosed herein is suitable in industry.

[0090] Effects of the Invention

[0091] According to the present disclosure, a new method for producing an imidic acid or an imidic acid salt having a phosphoryl group can be provided. DETAILED DESCRIPTION

[0092] Hereinafter, the present disclosure will be described in detail, but the description of the technical features described below is an example of the embodiment of the present disclosure and is not limited to these specific contents. Various modifications can be made within the scope of the gist of the present disclosure.

[0093] In the invention 1 and the invention 2, the water content in the compound represented by the general formula [3] or [6] used as a raw material in the reaction step can be set to 1000 mass ppm or less. If the water content is 1000 mass ppm or less, the compound represented by the general formula [2] or [5] as the reaction object is not easily hydrolyzed. From the above viewpoint, the smaller the water content, the more preferable it is.

[0094] In addition, in invention 1 and invention 2, from the viewpoint of suppressing the solvolysis and hydrolysis of the compound shown in the above-mentioned general formula [2] or [5] as the raw material of the reaction process, the above-mentioned reaction solvent that can also be used in the above-mentioned reaction process is optionally an aprotic solvent such as nitrile, chain ether, cyclic ether, chain ester, cyclic ester, chain carbonate, cyclic carbonate, sulfur-containing solvent. In addition, the water content in the aprotic solvent can be set to below 1000 mass ppm, or can be set to below 100 mass ppm. From the viewpoint of suppressing the hydrolysis of the compound shown in the above-mentioned general formula [2] or [5], the less the water content, the more preferably.

[0095] Specific examples of the above-mentioned aprotic solvents include nitriles such as acetonitrile, propionitrile, and valeronitrile, chain ethers such as diethyl ether, diisopropyl ether, and 1,2-dimethoxyethane, cyclic ethers such as tetrahydrofuran, 2-methyltetrahydrofuran, and tetrahydropyran, chain esters such as ethyl acetate, butyl acetate, and isopropyl acetate, cyclic esters such as γ-butyrolactone and γ-valerolactone, chain carbonates such as diethyl carbonate, dimethyl carbonate, and ethyl methyl carbonate, cyclic carbonates such as propylene carbonate, ethylene carbonate, and butylene carbonate, sulfur-containing solvents such as sulfolane, 3-methylsulfolane, and dimethyl sulfoxide. These aprotic solvents can also be used after dehydration. The dehydration method is not particularly limited, and for example, a method of adsorbing water by synthetic zeolite or the like can be used.

[0096] The above-mentioned aprotic solvents may be used alone or as a mixture of two or more thereof in any combination and at any ratio depending on the intended use.

[0097] In addition, the amount of the reaction solvent may be in the range of 0.1 to 100 parts by mass relative to 1 part by mass of the compound represented by the general formula [3] or [6]. If it is 0.1 parts by mass or more, it is easy to suppress the increase in viscosity caused by the imidic acid or imidic acid salt having a phosphoryl group represented by the general formula [1] generated by the reaction, and the subsequent reaction is easy to proceed smoothly. In addition, if it is 100 parts by mass or less, there is no problem with the reaction itself and it is economical. From the above viewpoints, the amount of the reaction solvent may be in the range of 0.1 to 20 parts by mass, or may be in the range of 1 to 10 parts by mass relative to 1 part by mass of the compound represented by the general formula [3] or [6].

[0098] The amount of the isocyanate compound represented by the general formula [2] or [5] used in the reaction step of the invention 1 and the invention 2 can be 0.1 to 10 moles relative to 1 mole of the compound represented by the general formula [3] or [6] as the respective reaction object. If it is 0.1 molar equivalent or more, more imidic acid or imidic acid salt having a phosphoryl group is obtained, which is economical. On the other hand, if it is 10 molar equivalents or less, less excess isocyanate compound is produced, which is economical. From the above viewpoint, the amount of the isocyanate compound represented by the general formula [2] or [5] can be 0.5 to 2 moles relative to 1 mole of the compound represented by the general formula [3] or [6].

[0099] Furthermore, if the compound represented by the general formula [3] or [6] is excessive, a step of filtering and removing the excess component from the reaction solution is required. Therefore, from the viewpoint of simplifying the process, the isocyanate compound that can be removed by degassing and concentration may be excessive. In this case, the amount of the isocyanate compound represented by the general formula [2] or [5] used can be 1.01 to 2 mol per 1 mol of the compound represented by the general formula [3] or [6].

[0100] The temperature of the reaction process of Invention 1 and Invention 2 can be appropriately adjusted in consideration of the thermal stability of the raw material compound, the generated imidic acid or imidic acid salt, etc., and can be set to, for example, a range of -20 to 200°C. If the reaction temperature is above -20°C, there is a tendency for the reaction time to be shortened. If it is below 200°C, decomposition of the raw material compound, the generated imidic acid or imidic acid salt is less likely to occur. The reaction temperature can be set to a range of 0 to 150°C, or to a range of 10 to 120°C.

[0101] There is no particular restriction on the reaction time of the reaction steps of Invention 1 and Invention 2, and the reaction time can be terminated after confirming that the raw material is fully consumed and the reaction is no longer proceeding by methods such as NMR, gas chromatography, and high performance liquid chromatography, and can be appropriately adjusted by those skilled in the art.

[0102] In the invention 1 and the invention 2, the isocyanate compound as a raw material and the reaction product thereof are easily hydrolyzed by moisture, and therefore, the reaction can be carried out in an atmosphere not containing moisture. For example, the reaction can be carried out in an atmosphere of an inert gas such as nitrogen.

[0103] The reactor used in the reaction process of Invention 1 and Invention 2 is not particularly limited in terms of material as long as it is not invaded by raw materials or reaction products, and a reactor or glass container lined with tetrafluoroethylene resin, chlorotrifluoroethylene resin, vinylidene fluoride resin, PFA resin, glass, etc. can be used. Metal containers such as stainless steel, Hastelloy, and monel can also be used. In addition, in order to suppress the foaming caused by the by-product CO2, defoaming blades can be provided on the inner wall of the reactor used, on the stirrer, or on both of them.

[0104] In the reaction process of Invention 1 and Invention 2, there is no particular restriction on the order of adding the reaction raw materials. Since there is a concern about the rapid generation of carbon dioxide gas as a by-product and foaming, the following order can be adopted: after the reaction solvent and the compound represented by the general formula [3] or [6] are added in sequence, stirring is performed, and the isocyanate compound represented by the general formula [2] or [5] as the corresponding reaction object is slowly added. There is no particular restriction on the addition time, and it can be set to any time, and the isocyanate compound can be added in 0.5 to 10 hours. If the addition time exceeds 10 hours, a long time is required, and therefore it is not economical. After the isocyanate compound represented by the general formula [2] or [5] is added as described above, stirring can be continued for about 1 to 15 hours to carry out the reaction.

[0105] In addition, the reaction liquid after the reaction process of Invention 1 and Invention 2 can be degassed and concentrated. It should be noted that degassing and concentration refers to the following method: the gas phase containing the volatile components from the above-mentioned reaction liquid is depressurized, or a carrier gas substantially free of water such as nitrogen, argon, and dry air is circulated, so that the volatile components are discharged outside the system, thereby increasing the concentration of the solute in the reaction liquid. In addition, by this operation, carbon dioxide dissolved as a by-product can be removed. The lower limit temperature during degassing and concentration can be set to -20°C, or 10°C. The upper limit temperature during degassing and concentration can be set to 90°C, or 60°C. If the temperature during degassing and concentration is above -20°C, the concentration efficiency is high. In addition, if it is below 90°C, the reaction liquid is not easy to color.

[0106] The reaction solution containing the imidic acid, imidic acid salt and solvent obtained by the manufacturing method disclosed herein can be used as, for example, an anion raw material of an ionic liquid, an electrolyte or additive for a nonaqueous electrolyte, an antistatic agent, etc. For the above-mentioned reaction solution, it can also be used for the above-mentioned purposes in a state of further filtering, concentrating, and diluting. In addition, the imidic acid or imidic acid salt can also be precipitated and separated by concentrating the above-mentioned reaction solution.

[0107] It should be noted that the reaction yield in the invention 1 is calculated based on the molar amount of the compound with the smaller input amount among the phosphoryl isocyanate represented by the general formula [2] and the compound represented by the general formula [3].

[0108] The reaction yield in Invention 2 is calculated based on the molar amount of the compound with the smaller input amount among the sulfonyl isocyanate represented by the general formula [5] and the compound represented by the general formula [6].

[0109] Example

[0110] Hereinafter, the present disclosure will be specifically described based on Examples, but the present disclosure is not limited to these Examples.

[0111] [Example 1]

[0112] [Chemistry 10]

[0113]

[0114] In a 50 mL glass reactor equipped with a stirrer and a thermometer, 20.00 g of propionitrile (water content: 40 mass ppm) as a reaction solvent were added under a nitrogen atmosphere.

[0115] 0.44 g (3.7 mmol) of lithium trifluoroacetate (water content: 90 mass ppm) as a compound represented by the general formula [3] was stirred at a liquid temperature of 23°C.

[0116] While maintaining the liquid temperature at 23°C, 0.70 g (4.4 mmol) of dichlorophosphoryl isocyanate, which is a phosphoryl isocyanate represented by the general formula [2], was added dropwise over 10 minutes. After the addition was completed, the liquid temperature was adjusted to 60°C and the reaction was continued by stirring for 8 hours. 19 The reaction solution was analyzed / quantified by F-NMR, and the reaction yield of [(dichlorophosphoryl)(trifluoromethanecarbonyl)imide] lithium salt was 98% based on lithium trifluoroacetate. The reaction solution was concentrated under reduced pressure to remove dissolved carbon dioxide and dichlorophosphoryl isocyanate, and [(dichlorophosphoryl)(trifluoromethanecarbonyl)imide] lithium salt was obtained. The results are shown in Table 1.

[0117] [Table 1]

[0118]

[0119] [Example 2]

[0120] [Chemistry 11]

[0121]

[0122] In a 50 mL glass reactor equipped with a stirrer and a thermometer, 20.00 g of ethyl acetate (water content: 30 mass ppm) and 0.60 g (8.7 mmol) of methacrylic acid (water content: 400 mass ppm) were added as a reaction solvent under a nitrogen atmosphere, and 0.07 g (8.8 mmol) of lithium hydride was added thereto, and the mixture was stirred at a liquid temperature of 20° C. to prepare lithium methacrylate as a compound represented by the general formula [3] (water content estimated to be less than 100 mass ppm).

[0123] While maintaining the liquid temperature at 20°C, 1.80 g (10.0 mmol) of diethyl phosphoryl isocyanate, which is a phosphoryl isocyanate represented by the general formula [2], was added dropwise over 30 minutes. After the addition was completed, stirring was continued for another 2 hours to allow the reaction to proceed. 19 The reaction solution was analyzed and quantified by F-NMR, and the reaction yield of [(diethylphosphoryl) (methacrylic acid) imide] lithium salt was 88% based on methacrylic acid. The reaction solution was concentrated under reduced pressure to remove dissolved carbon dioxide and diethylphosphoryl isocyanate, and [(diethylphosphoryl) (methacrylic acid) imide] lithium salt was obtained. The results are shown in Table 1.

[0124] [Example 3]

[0125] [Chemistry 12]

[0126]

[0127] In a 100 mL glass reactor equipped with a stirrer and a thermometer, 50 g of ethyl methyl carbonate (water content: 20 mass ppm) as a reaction solvent and 3.5 g (27.0 mmol) of lithium 2-picolinate (water content: 60 mass ppm) as a compound represented by the general formula [3] were added under a nitrogen atmosphere, and the mixture was stirred at a liquid temperature of 20°C.

[0128] While maintaining the liquid temperature at 20°C, 2.9 g (23.0 mmol) of difluorophosphoryl isocyanate, which is a phosphoryl isocyanate represented by the general formula [2], was added dropwise over 30 minutes. After the addition was completed, stirring was continued for another 4 hours to allow the reaction to proceed. 19 F-NMR was used to analyze / quantify the reaction solution, and the reaction yield of [(difluorophosphoryl) (2-picolinic acid) imide] lithium salt was 98% based on difluorophosphoryl isocyanate. The reaction solution was filtered to remove the residual 2-picolinic acid lithium, thereby obtaining a methyl ethyl carbonate solution of [(difluorophosphoryl) (2-picolinic acid) imide] lithium salt. The results are shown in Table 1.

[0129] [Example 4]

[0130] [Chemistry 13]

[0131]

[0132] In a 50 mL glass reactor equipped with a stirrer and a thermometer, 25 g of ethyl acetate (water content: 30 mass ppm) as a reaction solvent and 0.50 g (2.8 mmol) of sodium benzenesulfonate (water content: 200 mass ppm) as a compound represented by the general formula [3] were added under a nitrogen atmosphere, and stirred at a liquid temperature of 20°C.

[0133] While maintaining the liquid temperature at 20°C, 0.63 g (5.0 mmol) of difluorophosphoryl isocyanate, which is a phosphoryl isocyanate represented by the general formula [2], was added dropwise over 10 minutes. After the addition was completed, the liquid temperature was adjusted to 50°C and the reaction was continued by stirring for 8 hours. 19 F-NMR was used to analyze / quantify the reaction solution, and the reaction yield of [(difluorophosphoryl) (benzenesulfonyl) imide] sodium salt was 91% based on sodium benzenesulfonate. The reaction solution was concentrated under reduced pressure to remove dissolved carbon dioxide and difluorophosphoryl isocyanate, and [(difluorophosphoryl) (benzenesulfonyl) imide] sodium salt was obtained. In addition, during the concentration operation, the solvent ethyl acetate and difluorophosphoryl isocyanate were basically recovered as fractions. The results are shown in Table 1.

[0134] [Example 5]

[0135] [Chemistry 14]

[0136]

[0137] In a 50 mL glass reactor equipped with a stirrer and a thermometer, 30 g of ethylene carbonate (water content: 20 mass ppm) as a reaction solvent and 2.80 g (14.0 mmol) of triethylammonium difluorophosphate (water content: 80 mass ppm) as a compound represented by the general formula [3] were added under a nitrogen atmosphere, and stirred at a liquid temperature of 40°C.

[0138] While maintaining the liquid temperature at 40°C, 2.50 g (20 mmol) of difluorophosphoryl isocyanate, which is a phosphoryl isocyanate represented by the general formula [2], was added dropwise over 30 minutes. After the addition was completed, the liquid temperature was adjusted to 60°C and the reaction was continued by stirring for 8 hours. 19F-NMR analyzes / quantitatively the reaction solution, and the reaction yield of [bis (difluorophosphoryl) imide] triethylammonium salt is 98% based on the difluorophosphoryl triethylammonium salt benchmark as a result. The reaction solution is concentrated under reduced pressure, thereby removing dissolved carbonic acid gas and difluorophosphoryl isocyanate, obtaining the ethylene carbonate solution of [bis (difluorophosphoryl) imide] triethylammonium salt. In addition, in the concentrated under reduced pressure operation, difluorophosphoryl isocyanate is all recovered as a cut substantially. The results are shown in Table 1.

[0139] [Example 6]

[0140] [Chemistry 15]

[0141]

[0142] In a 50 mL glass reactor equipped with a stirrer and a thermometer, 10 g of tetrahydrofuran (water content: 50 mass ppm) as a reaction solvent and 1.46 g (9.8 mmol) of sodium dimethyl phosphate (water content: 120 mass ppm) as a compound represented by the general formula [3] were added under a nitrogen atmosphere, and stirred at a liquid temperature of 23°C.

[0143] While maintaining the liquid temperature at 23°C, 2.48 g (19.6 mmol) of difluorophosphoryl isocyanate, which is a phosphoryl isocyanate represented by the general formula [2], was added dropwise over 10 minutes. After the addition was completed, the liquid temperature was adjusted to 60°C and stirring was continued for another 5 hours to allow the reaction to proceed. 19 F-NMR was used to analyze / quantify the reaction solution, and the reaction yield of [(difluorophosphoryl) (dimethylphosphoryl) imide] sodium salt was 95% based on sodium dimethyl phosphate. The reaction solution was concentrated under reduced pressure to remove dissolved carbon dioxide and difluorophosphoryl isocyanate, and [(difluorophosphoryl) (dimethylphosphoryl) imide] sodium salt was obtained. In addition, in the reduced pressure concentration operation, tetrahydrofuran and difluorophosphoryl isocyanate were basically recovered as fractions. The results are shown in Table 1.

[0144] [Example 7]

[0145] [Chemistry 16]

[0146]

[0147] In a 100 mL stainless steel reactor equipped with a stirrer and a thermometer, under a nitrogen atmosphere,

[0148] 20 g of tetrahydrofuran (water content: 50 mass ppm) as a reaction solvent and 0.73 g (4.9 mmol) of sodium dimethyl phosphate (water content: 50 mass ppm) as a compound represented by the general formula [6] were added, and the mixture was stirred at a liquid temperature of 20°C.

[0149] While maintaining the liquid temperature at 20°C, 0.84 g (4.8 mmol) of trifluoromethanesulfonyl isocyanate, which is a sulfonyl isocyanate represented by the general formula [5], was added dropwise over 5 minutes. After the addition was completed, the liquid temperature was adjusted to 50°C and stirring was continued for another 4 hours to allow the reaction to proceed. 19 The reaction solution was analyzed and quantified by F-NMR, and the reaction yield of [(trifluoromethanesulfonyl)(dimethylphosphoryl)imide] sodium salt was 95% based on trifluoromethanesulfonyl isocyanate. The reaction solution was filtered to remove the residual sodium dimethyl phosphate, and then concentrated under reduced pressure to obtain [(trifluoromethanesulfonyl)(dimethylphosphoryl)imide] sodium salt. The results are shown in Table 2.

[0150] [Table 2]

[0151]

[0152] [Example 8]

[0153] [Chemistry 17]

[0154]

[0155] In a 50 mL glass reactor equipped with a stirrer and a thermometer, 25 g of ethyl methyl carbonate (water content: 20 mass ppm) as a reaction solvent were added under a nitrogen atmosphere.

[0156] 1.30 g (12.0 mmol) of lithium difluorophosphate (water content: 100 mass ppm) as a compound represented by the general formula [6] was stirred at a liquid temperature of 23°C.

[0157] While maintaining the liquid temperature at 23°C, 1.46 g (11.0 mmol) of vinylsulfonyl isocyanate, which is a sulfonyl isocyanate represented by the general formula [5], was added dropwise over 30 minutes. After the addition was completed, the liquid temperature was adjusted to 50°C and stirring was continued for another 12 hours to allow the reaction to proceed. 19 The reaction solution was analyzed and quantified by F-NMR, and the reaction yield of [(vinylsulfonyl)(difluorophosphoryl)imide] lithium salt was 96% based on vinylsulfonyl isocyanate. The reaction solution was filtered to remove the residual lithium difluorophosphate, and then concentrated under reduced pressure to obtain [(vinylsulfonyl)(difluorophosphoryl)imide] lithium salt. The results are shown in Table 2.

[0158] [Example 9]

[0159] [Chemistry 18]

[0160]

[0161] In a 50 mL glass reactor equipped with a stirrer and a thermometer, 25 g of ethylene carbonate (water content: 20 mass ppm) as a reaction solvent and 2.50 g (23.0 mmol) of lithium difluorophosphate (water content: 100 mass ppm) as a compound represented by the general formula [6] were added under a nitrogen atmosphere and stirred at a liquid temperature of 50°C.

[0162] While maintaining the liquid temperature at 50°C, 3.10 g (25.0 mmol) of fluorosulfonyl isocyanate, which is a sulfonyl isocyanate represented by the general formula [5], was added dropwise over 30 minutes. After the addition was completed, stirring was continued at the liquid temperature of 50°C for another 4 hours to allow the reaction to proceed. 19 F-NMR was used to analyze / quantify the reaction solution, and the reaction yield of [(fluorosulfonyl) (difluorophosphoryl) imide] lithium salt was 98% based on lithium difluorophosphate. The reaction solution was concentrated under reduced pressure to remove dissolved carbon dioxide and fluorosulfonyl isocyanate, thereby obtaining an ethylene carbonate solution of [(fluorosulfonyl) (difluorophosphoryl) imide] lithium salt. The results are shown in Table 2.

[0163] [Example 10]

[0164] [Chemistry 19]

[0165]

[0166] In a 50 mL glass reactor equipped with a stirrer and a thermometer, 25 g of ethyl acetate (water content: 30 mass ppm) as a reaction solvent and 1.74 g (13.0 mmol) of lithium monoethyl (fluoro)phosphate (water content: 120 mass ppm) as a compound represented by the general formula [6] were added under a nitrogen atmosphere, and the mixture was stirred at a liquid temperature of 50°C.

[0167] While maintaining the liquid temperature at 50°C, 1.46 g (11.0 mmol) of fluorosulfonyl isocyanate, which is a sulfonyl isocyanate represented by the general formula [5], was added dropwise over 30 minutes. After the addition was completed, stirring was continued at the liquid temperature of 50°C for further 5 hours to allow the reaction to proceed. 19 The reaction solution was analyzed / quantified by F-NMR, and the reaction yield of {[fluorosulfonyl][(fluoro)(ethyl)phosphoryl)]imide} lithium salt was 96% based on fluorosulfonyl isocyanate. The reaction solution was concentrated under reduced pressure to remove dissolved carbon dioxide and fluorosulfonyl isocyanate, and the insoluble matter was further filtered to remove, thereby obtaining an ethyl acetate solution of {[fluorosulfonyl][(fluoro)(ethyl)phosphoryl)]imide} lithium salt. The results are shown in Table 2.

[0168] [Example 11]

[0169] [Chemistry 20]

[0170]

[0171] In a 50 mL glass reactor equipped with a stirrer and a thermometer, 25 g of propylene carbonate (water content: 20 mass ppm) as a reaction solvent and 1.20 g (4.9 mmol) of sodium difluorophosphate (water content: 100 mass ppm) as a compound represented by the general formula [6] were added under a nitrogen atmosphere and stirred at a liquid temperature of 20°C.

[0172] While maintaining the liquid temperature at 20°C, 6.90 g (49.0 mmol) of chlorosulfonyl isocyanate, which is a sulfonyl isocyanate represented by the general formula [5], was added dropwise over 5 minutes. After the addition was completed, the liquid temperature was adjusted to 50°C and stirring was continued for another 8 hours to allow the reaction to proceed. 19 F-NMR was used to analyze / quantify the reaction solution, and the reaction yield of [(chlorosulfonyl) (difluorophosphoryl) imide] sodium salt was 90% based on sodium difluorophosphate. The reaction solution was concentrated under reduced pressure to remove dissolved carbon dioxide and chlorosulfonyl isocyanate to obtain a propylene carbonate solution of [(chlorosulfonyl) (difluorophosphoryl) imide] sodium salt. The results are shown in Table 2.

[0173] [Examples 1-1 to 1-2]

[0174] The reaction solution was obtained in the same manner as in Example 1 except that the water content of the compound represented by the general formula [3] used in Example 1 was changed as shown in Table 3. As shown in Table 3, it was confirmed that the lower the water content of the compound represented by the general formula [3] (particularly 1000 mass ppm or less), the higher the reaction yield could be achieved. It should be noted that it is speculated that the reason why the reaction yield is slightly reduced when the water content of the compound represented by the general formula [3] is relatively large (for example, exceeding 1000 mass ppm) is that a part of the compound represented by the general formula [2] as the reaction object is hydrolyzed. The results are shown in Table 3.

[0175] [Table 3]

[0176]

[0177] [Examples 7-1 to 7-2]

[0178] The reaction solution was obtained in the same manner as in Example 7 except that the water content of the compound represented by the general formula [6] used in Example 7 was changed as shown in Table 4. As shown in Table 4, it was confirmed that the lower the water content of the compound represented by the general formula [6] (particularly 1000 mass ppm or less), the higher the reaction yield could be achieved. It should be noted that it is speculated that the reason why the reaction yield is slightly reduced when the water content of the compound represented by the general formula [6] is large (for example, more than 1000 mass ppm) is that a part of the compound represented by the general formula [5] as the reaction object is hydrolyzed. The results are shown in Table 4.

[0179] [Table 4]

[0180]

[0181] [Examples 2-1 to 2-2]

[0182] The reaction solution was obtained in the same manner as in Example 2 except that the water content of the reaction solvent used in Example 2 was changed as shown in Table 5. As shown in Table 5, it was confirmed that the lower the water content of the reaction solvent (particularly below 100 mass ppm), the higher the reaction yield can be achieved. It should be noted that it is speculated that the slight decrease in the reaction yield when the water content of the reaction solvent is large (for example, exceeding 100 mass ppm) is due to the fact that a part of the compound represented by the general formula [2] is hydrolyzed. The results are shown in Table 5.

[0183] [Table 5]

[0184]

[0185] [Examples 8-1 to 8-2]

[0186] The reaction solution was obtained in the same manner as in Example 8 except that the water content of the reaction solvent used in Example 8 was changed as shown in Table 6. As shown in Table 6, it was confirmed that the lower the water content of the reaction solvent (particularly 100 mass ppm or less), the higher the reaction yield could be achieved. It should be noted that it is speculated that the slight decrease in the reaction yield when the water content of the reaction solvent is large (for example, more than 100 mass ppm) is due to the fact that a part of the compound represented by the general formula [5] is hydrolyzed. The results are shown in Table 6.

[0187] [Table 6]

[0188]

[0189] [Examples 3-1 to 3-4]

[0190] As shown in Table 7, the molar ratio [2] / [3] in Example 3 was changed, and a reaction solution was obtained in the same manner as in Example 3. As shown in Table 7, it was confirmed that by setting the molar ratio [2] / [3] to a range of 0.1 to 10, a high reaction yield can be achieved efficiently (economically). If [2] / [3] is 0.1 or more, more target products are obtained, which is an economically advantageous tendency. In addition, the amount of residual lithium 2-pyridinecarboxylate is small and it is easy to filter and remove it. On the other hand, if [2] / [3] is 10 or less, there is less excess isocyanate compound, which is an economically advantageous tendency. In addition, there is a tendency that the reaction yield is also high. It is speculated that this is because it is not easy to cause a reaction between the target imide compound and the slightly excess isocyanate compound. The results are shown in Table 7.

[0191] [Table 7]

[0192]

[0193] [Examples 9-1 to 9-4]

[0194] The reaction solution was obtained in the same manner as in Example 9 except that the molar ratio [5] / [6] in Example 9 was changed as shown in Table 8. As shown in Table 8, it was confirmed that a high reaction yield can be achieved efficiently (economically) by setting the molar ratio [5] / [6] to a range of 0.1 to 10. If [5] / [6] is 0.1 or more, more target products are obtained, which is an economically advantageous tendency. In addition, the amount of residual lithium difluorophosphate is small and it is easy to filter and remove it. On the other hand, if [5] / [6] is 10 or less, less excess isocyanate compounds are present, which is an economically advantageous tendency. In addition, the reaction yield tends to be high. It is speculated that this is because it is not easy to cause a reaction between the target imide compound and the slightly excess isocyanate compound. The results are shown in Table 8.

[0195] [Table 8]

[0196]

[0197] [Examples 5-1 to 5-4]

[0198] As shown in Table 9, the reaction temperature in Example 5 was changed. In addition, a reaction solution was obtained in the same manner as in Example 5. As shown in Table 9, if the reaction temperature is below 120°C, a particularly high tendency in the reaction yield can be seen. In addition, if it is set to above 10°C, a particularly large tendency in the reaction speed can be seen. Since the reaction time is the same as in Example 5, the reaction yield of Example 5-1 decreases, but a good reaction yield can be achieved if sufficient reaction time is spent. However, from the viewpoint of productivity, it can be said that this situation is an unfavorable tendency. The results are shown in Table 9.

[0199] [Table 9]

[0200]

[0201] [Examples 11-1 to 11-4]

[0202] As shown in Table 10, the reaction temperature in Example 11 was changed. In addition, a reaction solution was obtained in the same manner as in Example 11. As shown in Table 10, if the reaction temperature is below 120°C, a particularly high tendency in the reaction yield can be seen. In addition, if it is set to above 10°C, a particularly large tendency in the reaction rate can be seen. Since the reaction time is the same as in Example 11, the reaction yield of Example 11-1 becomes low, but a good reaction yield can be achieved if sufficient reaction time is spent. However, from the viewpoint of productivity, it can be said that this situation is an unfavorable tendency. The results are shown in Table 10.

[0203] [Table 10]

[0204]

[0205] [Examples 6-1 to 6-6]

[0206] As shown in Table 11, the amount of the reaction solvent relative to 1 mass part of the compound represented by the general formula [3] in Example 6 was changed. In addition, a reaction solution was obtained in the same manner as in Example 6. As shown in Table 11, if the amount of the reaction solvent is more than 1 mass part, it can be seen that the reaction speed tends to be particularly large. Since the reaction time is the same as in Example 6, the reaction yield of Example 6-1 decreases, but if sufficient reaction time is spent, a good reaction yield can be achieved. However, from the viewpoint of productivity, it can be said that this situation is an unfavorable tendency. The results are shown in Table 11.

[0207] [Table 11]

[0208]

[0209] [Examples 9-1 to 9-7]

[0210] As shown in Table 12, the amount of the reaction solvent relative to 1 part by mass of the compound represented by the general formula [6] in Example 9 was changed. In addition, a reaction solution was obtained in the same manner as in Example 9. As shown in Table 12, if the amount of the reaction solvent is 1 part by mass or more, it can be seen that the reaction speed tends to be particularly large. Since the reaction time is the same as in Example 9, the reaction yield of Example 9-1 is reduced, but a good reaction yield can be achieved if sufficient reaction time is spent. However, from the viewpoint of productivity, it can be said that this situation is an unfavorable tendency. The results are shown in Table 12.

[0211] [Table 12]

[0212]

[0213] As described above, even when various conditions are changed, the imidic acid or imidic acid salt having a phosphoryl group can be produced by using the production method disclosed herein.

[0214] Industrial Applicability

[0215] According to the present disclosure, a new method for producing an imidic acid or an imidic acid salt having a phosphoryl group can be provided.

[0216] While the present disclosure has been described in detail and with reference to specific embodiments, it will be apparent to one skilled in the art that various changes and modifications can be made therein without departing from the spirit and scope of the present disclosure.

[0217] This application is based on the Japanese patent application (Japanese Patent Application No. 2022-162214) filed on October 7, 2022, the contents of which are incorporated herein by reference.

Claims

1. A method for producing an imidic acid or an imidic acid salt represented by the following general formula [1], comprising the following reaction steps: The phosphoryl isocyanate represented by the following general formula [2] is reacted with the compound represented by the following general formula [3], [Chemistry 1] In the general formula [1], X 1 , X 2 each independently represents a chlorine atom, a fluorine atom, an organic group selected from a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms, and at least one selected from a fluorine atom, an oxygen atom, a nitrogen atom and an unsaturated bond may also exist in the organic group, Z is -P(=O)-, -S(=O)2- or -C(=O)-. When Z is -P(=O)-, a is 1. When Z is -S(=O)2- or -C(=O)-, a is 0. R 1 , R 2 each independently represents a chlorine atom, a fluorine atom, an organic group selected from a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkyloxy group having 3 to 10 carbon atoms, a cycloalkenyl group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms, and at least one selected from a fluorine atom, an oxygen atom and an unsaturated bond may also be present in the organic group, M is a proton, an alkali metal cation, an alkaline earth metal cation or an onium cation, and m represents an integer having the same valence as the corresponding cation. [Chemistry 2] In the general formula [2], X 1 , X 2 each independently represents a chlorine atom, a fluorine atom, an organic group selected from a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms, and at least one selected from a fluorine atom, an oxygen atom, a nitrogen atom and an unsaturated bond may also exist in the organic group, [Chemistry 3] In the general formula [3], Z is -P(=O)-, -S(=O)2- or -C(=O)-, When Z is -P(=O)-, a is 1, When Z is -S(=O)2-, a is 0, When Z is -C(=O)-, a is 0, R 1 , R 2 each independently represents a chlorine atom, a fluorine atom, an organic group selected from a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkyloxy group having 3 to 10 carbon atoms, a cycloalkenyl group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms, and at least one selected from a fluorine atom, an oxygen atom and an unsaturated bond may also be present in the organic group, M is a proton, an alkali metal cation, an alkaline earth metal cation or an onium cation, and m represents an integer which is the same as the valence number of the corresponding cation.

2. The method for producing an imidic acid or an imidic acid salt according to claim 1, wherein The amount of the phosphoryl isocyanate represented by the general formula [2] used is 0.1 to 10 mol per 1 mol of the compound represented by the general formula [3].

3. The method for producing an imidic acid or an imidic acid salt according to claim 1 or 2, wherein: The reaction temperature in the reaction step is -20 to 200°C.

4. The method for producing an imidic acid or an imidic acid salt according to claim 1 or 2, wherein: The reaction process is carried out in a reaction solvent.

5. The method for producing an imidic acid or an imidic acid salt according to claim 4, wherein: The reaction solvent is at least one solvent selected from the group consisting of nitriles, chain ethers, cyclic ethers, chain esters, cyclic esters, chain carbonates, cyclic carbonates and sulfur-containing solvents.

6. The method for producing an imidic acid or an imidic acid salt according to claim 1 or 2, wherein: The M m+ It is a proton, a lithium ion, a sodium ion, a potassium ion, a trialkylammonium ion or a tetraalkylammonium ion.

7. The method for producing an imidic acid or an imidic acid salt according to claim 1 or 2, wherein: The X 1 , X 2 Each is independently a group selected from a chlorine atom, a fluorine atom, a methyl group, a trifluoromethyl group, a phenyl group, a fluorophenyl group, a vinyl group, a thienyl group and a pyridyl group.

8. The method for producing an imidic acid or an imidic acid salt according to claim 1 or 2, wherein: The reaction solution after the reaction step is degassed and concentrated.

9. A method for producing an imidic acid or an imidic acid salt represented by the following general formula [4], comprising the following reaction steps: A sulfonyl isocyanate represented by the following general formula [5] is reacted with a compound represented by the following general formula [6], [Chemistry 4] In the general formula [4], X 1 , X 2 each independently represents a chlorine atom, a fluorine atom, an organic group selected from a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms, and at least one selected from a fluorine atom, an oxygen atom, a nitrogen atom and an unsaturated bond may also exist in the organic group, R 1 is a chlorine atom, a fluorine atom, an organic group selected from a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkyloxy group having 3 to 10 carbon atoms, a cycloalkenyl group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms, and at least one selected from a fluorine atom, an oxygen atom and an unsaturated bond may further be present in the organic group, M is a proton, an alkali metal cation, an alkaline earth metal cation or an onium cation, and m represents an integer having the same valence as the corresponding cation. [Chemistry 5] In the general formula [5], R 1 is a chlorine atom, a fluorine atom, an organic group selected from a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkyloxy group having 3 to 10 carbon atoms, a cycloalkenyl group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms, and at least one selected from a fluorine atom, an oxygen atom and an unsaturated bond may further be present in the organic group, [Chemistry 6] In the general formula [6], X 1 , X 2 each independently represents a chlorine atom, a fluorine atom, an organic group selected from a linear or branched alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms, and at least one selected from a fluorine atom, an oxygen atom, a nitrogen atom and an unsaturated bond may also exist in the organic group, M is a proton, an alkali metal cation, an alkaline earth metal cation or an onium cation, and m represents an integer which is the same as the valence number of the corresponding cation.

10. The method for producing an imidic acid or an imidic acid salt according to claim 9, wherein: The amount of the sulfonyl isocyanate represented by the general formula [5] used is 0.1 to 10 mol per 1 mol of the compound represented by the general formula [6].

11. The method for producing an imidic acid or an imidic acid salt according to claim 9 or 10, wherein: The reaction temperature in the reaction step is 0 to 150°C.

12. The method for producing an imidic acid or an imidic acid salt according to claim 9 or 10, wherein: The reaction process is carried out in a reaction solvent.

13. The method for producing an imidic acid or an imidic acid salt according to claim 12, wherein: The reaction solvent is at least one solvent selected from the group consisting of nitriles, chain ethers, cyclic ethers, chain esters, cyclic esters, chain carbonates, cyclic carbonates and sulfur-containing solvents.

14. The method for producing an imidic acid or an imidic acid salt according to claim 9 or 10, wherein: The M m+ It is a proton, a lithium ion, a sodium ion, a potassium ion, a trialkylammonium ion or a tetraalkylammonium ion.

15. The method for producing an imidic acid or an imidic acid salt according to claim 9 or 10, wherein: The X 1 , X 2 Each is independently a group selected from a chlorine atom, a fluorine atom, a methyl group, a trifluoromethyl group, a phenyl group, a fluorophenyl group, a vinyl group, a thienyl group and a pyridyl group.

16. The method for producing an imidic acid or an imidic acid salt according to claim 9 or 10, wherein: The reaction solution after the reaction step is degassed and concentrated.

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