WO2010113835A1 - イミド酸化合物の製造方法 - Google Patents
イミド酸化合物の製造方法 Download PDFInfo
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- WO2010113835A1 WO2010113835A1 PCT/JP2010/055508 JP2010055508W WO2010113835A1 WO 2010113835 A1 WO2010113835 A1 WO 2010113835A1 JP 2010055508 W JP2010055508 W JP 2010055508W WO 2010113835 A1 WO2010113835 A1 WO 2010113835A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/34—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfuric acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/26—Amides of acids of phosphorus containing P-halide groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0252—Nitrogen containing compounds with a metal-nitrogen link, e.g. metal amides, metal guanidides
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
- C01B21/086—Compounds containing nitrogen and non-metals and optionally metals containing one or more sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
- C01B21/087—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms
- C01B21/093—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms containing also one or more sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
- C01B21/097—Compounds containing nitrogen and non-metals and optionally metals containing phosphorus atoms
- C01B21/0975—Compounds containing nitrogen and non-metals and optionally metals containing phosphorus atoms containing also one or more sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/12—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of quaternary ammonium compounds
Definitions
- the present invention relates to an imidic acid compound useful as a pharmaceutical, an agrochemical intermediate, a battery electrolyte, and an acid catalyst, specifically, a method for producing a bis (halogenated sulfonyl) imide or a bis (dihalogenated phosphonyl) imidic acid compound.
- a bis (halogenated sulfonyl) imide or a bis (dihalogenated phosphonyl) imidic acid compound is about.
- the bis (halogenated sulfonyl) imide and bis (dihalogenated phosphonyl) imidic acid compounds that have been widely known are useful substances as battery electrolyte solvents, acid catalysts, ionic liquids, and antistatic agents.
- Patent Document 1 discloses a method for producing bis (fluorosulfonyl) imide acid by reacting urea (NH 2 —CO—NH 2 ) with fluorosulfonic acid
- non-patent Document 1 discloses a production method for obtaining bis (fluorosulfonyl) imidic acid by reacting bis (chlorosulfonyl) imidic acid with a metal fluoride.
- Patent Document 2 discloses a method in which chloro (sulfonic acid) (ClSO 3 H) and chlorosulfonyl isocyanate (ClSO 2 NCO) are reacted to obtain bis (chlorosulfonyl) imidic acid.
- Non-Patent Document 3 discloses a method of reacting chlorosulfonic acid (ClSO 3 H) and N-sulfonyltrichlorophosphazene (ClSO 2 NPCl 3 ) to obtain bis (chlorosulfonyl) imidic acid.
- Non-Patent Document 4 discloses reacting LiN (SiMe 3 ) 2 which is a silazane metal compound with phosphoryl trifluoride (POF 3 ) to produce bis (difluorophosphonyl).
- LiN (SiMe 3 ) 2 which is a silazane metal compound with phosphoryl trifluoride (POF 3 ) to produce bis (difluorophosphonyl).
- PPF 3 phosphoryl trifluoride
- Non-patent documents 5 and 6 are reacted with sulfuryl chloride or sulfuryl fluoride and anhydrous ammonia to obtain sulfamide (H 2 NSO 2 NH 2 ).
- Patent Document 3 discloses a production method in which a tertiary amine such as a silazane derivative and a halogenated sulfuryl are reacted to obtain a bis (halogenated sulfonyl) imidic acid derivative.
- Patent Document 1 In the method of Patent Document 1, it is difficult to separate bis (fluorosulfonyl) imidic acid and fluorosulfonic acid obtained by this reaction using fluorosulfonic acid having high toxicity and corrosivity, and low yield. Therefore, it is difficult to adopt as an industrial manufacturing method.
- the methods of Non-Patent Documents 1 and 2 are disadvantageous for industrial mass production because they use arsenic trifluoride and antimony trifluoride, which are highly toxic and expensive.
- Patent Document 2 and Non-Patent Document 3 are disadvantageous in that relatively expensive chlorosulfonyl isocyanate (ClSO 2 NCO) or N-sulfonyltrichlorophosphazene (ClSO 2 NPCl 3 ) is used.
- chlorosulfonyl isocyanate ClSO 2 NCO
- N-sulfonyltrichlorophosphazene ClSO 2 NPCl 3
- R is a halosulfonyl group (—SO 2 X 1 ; X 1 is a halogen (fluorine, chlorine, bromine, iodine)) or a dihalophosphoryl group (—POX 2 X 3 ; X 2 , X 3 represents the same or different halogen (fluorine, chlorine, bromine, iodine)).
- B represents an organic base.
- X 6 X 7 X 8 : X 6 , X 7 , X 8 represent the same or different halogen (fluorine, chlorine, bromine, iodine) And the same or different from the above-mentioned X 2 and X 3 ), and by reacting with ammonia, the “salt or complex comprising imide acid and organic base” represented by the formula [1] is highly selective. And the knowledge which can be manufactured with a high yield was acquired, and this invention was completed.
- [Invention 1] A process for producing a “salt or complex comprising an imide acid and an organic base” represented by the formula [1], characterized by reacting sulfuryl halide or phosphoryl halide with ammonia in the presence of an organic base.
- the organic base is a tertiary amine represented by the formula [2]
- R 1 , R 2 , and R 3 are the same or different and each represents a linear or branched alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, or an aryl group (aryl A part or all of the hydrogen atoms of the group are halogen (fluorine, chlorine, bromine, iodine), an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, And may be substituted with an amino group, a nitro group, an acetyl group, a cyano group, or a hydroxyl group. ], Nitrogen-containing aromatic heterocyclic compound, or the following imine skeleton —C ⁇ N—C— The method according to any one of
- Invention 5 The method according to any one of Inventions 1 to 4, wherein the organic base is trimethylamine, triethylamine, diisopropylethylamine, tri-n-propylamine, tributylamine, or pyridine.
- invention 6 6. The method according to any one of inventions 1 to 5, wherein the amount of the organic base is 1 to 50 mol with respect to 1 mol of ammonia.
- invention 7 The method according to any one of inventions 1 to 3, wherein the amount of the sulfuryl halide or phosphoryl halide used is 1 mol to 10 mol with respect to 1 mol of ammonia.
- the “salt or complex comprising imide acid and organic base” obtained by the method according to any one of Inventions 1 to 8 includes an alkali metal hydroxide or carbonate, or an alkaline earth metal hydroxide.
- a metal imidate represented by the formula [3], characterized by reacting with a carbonate [In the formula [3], R is the same as defined above.
- M represents an alkali metal or an alkaline earth metal.
- n represents an integer equal to the valence of the corresponding metal. ] Manufacturing method.
- the present invention is characterized by “reacting halogenated sulfuryl or halogenated phosphoryl and ammonia in the presence of an organic base”.
- a compound called “sulfamide” is produced.
- This document also discloses that a large amount of by-products are produced in addition to sulfamide (see Scheme 1).
- Patent Document 3 discloses that a corresponding imide compound can be produced by reacting a sulfuryl halide with an amine such as a silazane derivative.
- the method of Patent Document 3 is applied to the present invention.
- SO 2 F 2 sulfuryl fluoride
- the target product “salt or complex composed of bisfluorosulfonylimide acid and organic base” is hardly obtained, and by-products such as sulfamide are obtained. (See scheme 2 below).
- the present inventors coexisted with an organic base in addition to ammonia in the reaction system, so that almost no sulfamide was produced, and a high conversion rate and high selectivity were obtained with a “salt comprising imidic acid and an organic base or It was found that a “complex” was obtained (see Scheme 3 below).
- the present invention has found preferable conditions for the method of introducing the reagent into the reaction system in carrying out the present invention.
- the order of addition into the reaction system that is, by adding an organic base and sulfuryl fluoride into the system, and then introducing ammonia into the reaction system, high selectivity and high yield can be obtained.
- the present inventors have found extremely useful knowledge that the object can be obtained.
- the “salt or complex comprising bis (halogenated sulfonyl) imidic acid and an organic base” can be easily expressed by reacting an alkali metal hydroxide or an alkaline earth metal hydroxide with the formula [3]. It was also found that a bis (halogenated sulfonyl) imidic acid metal salt represented by
- the present invention is capable of producing a target imidic acid derivative in a high yield while significantly suppressing the production of by-products, using sulfuryl halide or phosphoryl halide that is inexpensive and suitable for handling a large amount. There is an effect.
- the present invention is a process for producing a “salt or complex comprising an imidic acid and an organic base” represented by the formula [1], wherein sulfuryl halide or phosphoryl halide and ammonia are reacted in the presence of an organic base. It is the manufacturing method of "the salt or complex which consists of an imide acid and an organic base” characterized by the above-mentioned.
- halogenated sulfuryl examples include sulfuryl fluoride, sulfuryl chloride, sulfuryl bromide and sulfuryl iodide
- halogenated phosphoryl examples include phosphoryl fluoride, phosphoryl chloride, phosphoryl bromide and phosphoryl iodide.
- sulfuryl fluoride, sulfuryl chloride, phosphoryl fluoride, and phosphoryl chloride are particularly preferred.
- the amount of sulfuryl halide or phosphoryl halide is usually 1 to 10 mol, preferably 1 to 8 mol, more preferably 1 to 5 mol per mol of ammonia.
- the organic base used in the present invention is a tertiary amine represented by the formula [2], a nitrogen-containing aromatic heterocyclic compound, or the following imine skeleton —C ⁇ N—C— Specific examples of each compound will be described below.
- (A) Tertiary amine trimethylamine, triethylamine, N-ethyldiisopropylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, trioctylamine, tridecylamine, triphenylamine, tribenzylamine, Tris (2-ethylhexyl) amine, N, N-dimethyldecylamine, N-benzyldimethylamine, N-butyldimethylamine, N, N-dimethylcyclohexylamine, N, N, N ′, N′-tetramethyl Ethylenediamine, N, N-dimethylaniline, N, N-diethylaniline, 1,4-diazabicyclo [2.2.2] octane, N-methylpyrrolidine, N-methylpiperidine, N-methylmorpholine, N-ethylmorpholine, N, N'-dimethyl
- Nitrogen-containing aromatic heterocyclic compounds pyridine, 2,4,6-trimethylpyridine, 4-dimethylaminopyridine, lutidine, pyrimidine, pyridazine, pyrazine, oxazole, isoxazole, thiazole, isothiazole, imidazole, 1 , 2-dimethylimidazole, 3- (dimethylamino) propylimidazole, pyrazole, furazane, pyrazine, quinoline, isoquinoline, purine, 1H-indazole, quinazoline, cinnoline, quinoxaline, phthalazine, pteridine, phenanthridine, 2,6-di -T-butylpyridine, 2,2'-bipyridine, 4,4'-dimethyl-2,2'-bipyridyl, 4,4'-dimethyl-2,2'-bipyridyl, 5,5'
- tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine, tripropylamine, tributylamine, secondary amines such as diisopropylamine, pyridine, 2,3-lutidine, 2,4-lutidine, 2,6-lutidine, Nitrogen-containing aromatic heterocyclic compounds such as 3,4-lutidine, 3,5-lutidine, 2,4,6-collidine, 3,5,6-collidine and the like are preferable, trimethylamine, triethylamine, diisopropylethylamine, tripropylamine , Tributylamine, pyridine and the like are more preferable.
- the amount of organic base used is stoichiometrically 3 moles per mole of ammonia and 1.5 moles per mole of sulfuryl halide or phosphoryl halide. As shown, it is preferable to use more than the stoichiometric amount in order to allow the reaction to proceed smoothly.
- the organic base is used in an amount of 1 to 50 moles (preferably 1 to 10 moles) per mole of ammonia, and 1.5 to 10 moles (preferably 1 mole of the sulfuryl or phosphoryl). Is 2 to 5 mol).
- the reaction can be carried out in the presence of an organic solvent or water.
- the organic solvent means an inert organic compound that does not directly participate in the reaction of the present invention.
- Reaction solvents include aliphatic hydrocarbons such as n-hexane, cyclohexane and n-heptane, aromatic hydrocarbons such as benzene, toluene, xylene and mesitylene, halogens such as methylene chloride, chloroform and 1,2-dichloroethane.
- Hydrocarbons such as diethyl ether, tetrahydrofuran and tert-butyl methyl ether, esters such as ethyl acetate and butyl acetate, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and the like
- esters such as ethyl acetate and butyl acetate, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and the like
- Examples include amides, nitriles such as acetonitrile and propionitrile, and dimethyl sulfoxide.
- esters such as ethyl acetate and butyl acetate, amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidone, nitriles such as acetonitrile and propionitrile, and dimethyl sulfoxide are preferable. Nitriles such as acetonitrile and propionitrile are more preferable.
- the amount of the organic solvent or water used is not particularly limited, but it is sufficient to use 0.1 L (liter) or more with respect to 1 mol of ammonia, usually 0.1 to 20 L is preferable, particularly 0.1 to 10L is more preferable.
- organic base when the above-mentioned organic base is a liquid, since these organic bases (for example, triethylamine etc.) also serve as a solvent, they can be used in excess to function as a solvent.
- organic bases for example, triethylamine etc.
- the temperature condition is not particularly limited, but may be in the range of ⁇ 50 to 150 ° C. Usually, ⁇ 20 to 100 ° C. is preferable, and ⁇ 10 to 70 ° C. is more preferable. If the temperature is lower than ⁇ 50 ° C., the reaction rate is slow, and if the temperature exceeds 150 ° C., decomposition of the product may occur.
- the pressure condition is not particularly limited, and can be performed under normal pressure conditions (0.1 MPa (absolute pressure; the same applies hereinafter)) or under reduced pressure conditions or pressurized conditions using a reactor that can withstand the pressure. . That is, it may be performed in the range of 0.01 MPa to 2 MPa, but is preferably 0.01 MPa to 1.5 MPa, more preferably 0.1 MPa to 1 MPa.
- reaction vessel used in the reaction examples include a pressure-resistant reaction vessel lined with Monel, Hastelloy, nickel, or a fluorine resin such as these metals, polytetrafluoroethylene, or perfluoropolyether resin.
- the reaction time is not particularly limited, but may be in the range of 0.1 to 48 hours. Since the reaction time varies depending on the substrate and reaction conditions, the progress of the reaction can be performed by analytical means such as gas chromatography, liquid chromatography, and NMR. It is preferable that the end point is the time when the raw material is almost disappeared by tracking the situation.
- a “salt or complex consisting of an imidic acid and an organic base” represented by the formula [1] is obtained.
- an organic solvent, an organic base, a halogenated sulfuryl or a halogenated phosphoryl is added to a pressure-resistant reaction vessel such as an autoclave, and then add ammonia, and then close the vessel for reaction.
- the reaction is preferably performed with 2 to 5 mol of sulfuryl halide or phosphoryl halide and 3 to 10 mol of organic base with respect to 1 mol of ammonia.
- the amount of the organic solvent used is preferably 0.1 to 20 L with respect to 1 mol of ammonia, and the temperature condition is preferably 0 to 100 ° C.
- the pressure condition is preferably 0.1 MPa to 1.5 MPa.
- the “salt or complex consisting of imido acid and an organic base”, which is the target product is itself a compound insoluble in water, but the following by-product in the reaction system, XSO 2 NHSO 2 NHSO 2 X May be produced in trace amounts.
- by-products can be removed by a simple operation (such as washing with water).
- the operation of adding water and washing is one of the preferred embodiments from the viewpoint of improving the chemical purity of the “salt or complex comprising imide acid and organic base” which is the target product.
- alkali metal hydroxide examples include lithium hydroxide (LiOH), potassium hydroxide (KOH), rubidium hydroxide (RbOH), and cesium hydroxide (CsOH).
- alkali metal carbonate examples include lithium carbonate (Li 2).
- alkali metal hydroxides or carbonates, or alkaline earth metal hydroxides or carbonates may be used alone or in combination of two or more.
- a combination of the same alkali metal hydroxide and carbonate for example, potassium hydroxide and potassium carbonate
- the same alkaline earth metal hydroxide and carbonate for example, hydroxide
- the amount of alkali metal hydroxide or carbonate, or alkaline earth metal hydroxide or carbonate used is preferably 1 to 5 moles per mole of “salt or complex comprising imide acid and organic base” More preferably, it is 1 mol to 3 mol.
- an amount exceeding 5 mol that is, an excessive amount of base is reacted, the reaction proceeds, but the “salt or complex composed of imido acid and organic base” is decomposed, and the yield may be reduced. For this reason, it is not preferable to use an excessive amount of base.
- the amount is less than 1 mol, the conversion rate decreases, which is not preferable.
- a solvent When reacting an alkali metal hydroxide or carbonate or an alkaline earth metal hydroxide or carbonate, a solvent can be used.
- water when water is used as a solvent, water is added so that the base concentration is usually 10% by mass to 70% by mass, preferably 20% by mass to 60% by mass, more preferably 30% by mass to 60% by mass. And good. If the amount of water is too small, stirring in the reaction system becomes difficult, and if it is too large, processing after the reaction becomes complicated and a reaction container larger than usual is required.
- An organic solvent other than water can also be used.
- Solvents such as ethers such as diethyl ether, dioxane, tetrahydrofuran and ethylene glycol dimethyl ether can be used. It can also be used in combination with water.
- the amount of the solvent to be used is appropriately selected from the range of usually 0.5 to 10 times, preferably 1 to 7 times the volume of “a salt or complex comprising imide acid and organic base”. However, since the reaction proceeds sufficiently even if water is used, there is little merit in using an organic solvent other than water.
- the reaction temperature is not particularly limited, but is usually ⁇ 10 ° C. to 110 ° C., preferably 25 to 80 ° C. If the temperature is lower than ⁇ 10 ° C., the reaction does not proceed sufficiently and causes a decrease in yield, which is economically disadvantageous, or causes a problem that the reaction rate decreases and it takes a long time to complete the reaction. There is a case. On the other hand, when the temperature exceeds 110 ° C., by-products are likely to be generated, and excessive heating is not energy efficient.
- the reaction time is not particularly limited, but it may usually be within a range of 24 hours.
- the progress of the reaction is traced by an analytical means such as ion chromatography or NMR, and the end point when the raw material substrate has almost disappeared. Is preferable.
- the reactor used in this process is made of metal containers such as stainless steel, Hastelloy, Monel, tetrafluoroethylene resin, chlorotrifluoroethylene resin, vinylidene fluoride resin, PFA resin, polypropylene resin, polyethylene resin, and glass.
- a reactor capable of sufficiently performing a reaction under normal pressure or pressure can be used, such as one lined inside.
- a liter autoclave was charged with 184 g of acetonitrile and 184 g (1.82 mol) of triethylamine, cooled to 5 ° C. with ice water, and 153 g (1.50 mol) of sulfuryl fluoride was introduced. After introducing sulfuryl fluoride, 9.1 g (0.53 mol) of anhydrous ammonia was subsequently introduced over 1 hour. The reactor was warmed to room temperature and stirred for 48 hours. The production ratio of this reaction was 99.2%, and 0.8% of FSO 2 NHSO 2 NHSO 2 F was produced. The solvent of this reaction solution was distilled off, and ether and water were added to the residue, followed by extraction and washing with water.
- a 1 L autoclave was charged with 384 g of acetonitrile and 158 g (2.00 mol) of pyridine, cooled to 5 ° C. with ice water, and 132 g (1.29 mol) of sulfuryl fluoride was introduced. After introducing sulfuryl fluoride, 9.8 g (0.58 mol) of anhydrous ammonia was introduced over 1 hour. The reactor was warmed to room temperature and stirred for 48 hours. The production ratio of this reaction was 99.0%, and 1.0% of FSO 2 NHSO 2 NHSO 2 F was produced. The solvent of this reaction solution was distilled off, and ether and water were added to the residue, followed by extraction and washing with water. Next, the organic layer was separated and the solvent was distilled off to obtain 127 g of bisfluorosulfonylimide pyridine salt (note that the pyridine salt was used in the next reaction as it was without isolation and purification). .
- a 200 mL autoclave was charged with 105 g of acetonitrile and 21.2 g (210 mmol) of triethylamine, cooled to 5 ° C. with ice water, and 1.2 g (70 mmol) of anhydrous ammonia was added. Next, 15.5 g (152 mmol) of sulfuryl fluoride was introduced. The reactor was warmed to room temperature and stirred for 12 hours. The production ratio of this reaction was 82.3%, and 17.7% of FSO 2 NHSO 2 NHSO 2 F was produced. The solvent of this reaction solution was distilled off, and ether and water were added to the residue, followed by extraction and washing with water.
- a 1 L autoclave was charged with 200 g of acetonitrile and 72 g (0.71 mol) of triethylamine, cooled to 5 ° C. with ice water, and 57.4 g (0.374 mol) of phosphoryl chloride was introduced. Subsequently, anhydrous ammonia (3.0 g, 0.176 mol) was introduced over 1 hour. The reactor was warmed to room temperature and stirred for 48 hours. The production ratio of this reaction was 98% for the production of bis (dichlorophosphoryl) imide, and 2% of the intermediate chlorophosphorylamide remained.
- this white solid was sulfamide (H 2 NSO 2 NH 2 ), and this white solid contained 3 wt% of fluorosulfonylamide (FSO 2 NH 2 ), and the bisfluorosulfonylimide ammonium salt was It contained only 0.3 wt%. (Yield 0.1%) Thus, it can be seen that when the organic base is not present, the target ammonium salt is hardly obtained.
Abstract
Description
の製造方法であって、有機塩基存在下、ハロゲン化スルフリル(SO2X4X5、:X4、X5は同一、又は異なるハロゲン(フッ素、塩素、臭素、ヨウ素)を表し、前述のX1と同一、又は異なる。)もしくはハロゲン化ホスホリル(P(=O)X6X7X8:X6、X7、X8は同一、又は異なるハロゲン(フッ素、塩素、臭素、ヨウ素)を表し、前述のX2、X3と同一、又は異なる。)、及びアンモニアを反応させることにより、式[1]で表される、「イミド酸と有機塩基からなる塩又は錯体」を、高選択率かつ高収率で製造できる知見を得、本発明を完成した。
式[1]で表される、「イミド酸と有機塩基からなる塩又は錯体」の製造方法であって、有機塩基存在下、ハロゲン化スルフリルもしくはハロゲン化ホスホリル、及びアンモニアを反応させることを特徴とする、式[1]で表される、「イミド酸と有機塩基からなる塩又は錯体」の製造方法。
式[1]で表される、「イミド酸と有機塩基からなる塩又は錯体」の製造方法であって、有機塩基存在下、ハロゲン化スルフリル、及びアンモニアを反応させることを特徴とする、式[1]で表される、「イミド酸と有機塩基からなる塩又は錯体」の製造方法。
有機塩基、及びハロゲン化スルフリルもしくはハロゲン化ホスホリルを反応系内に共存させた後、続けてアンモニアを反応させることにより行うことを特徴とする、発明1又は2に記載の方法。
有機塩基が、式[2]で表される3級アミン
-C=N-C-
を有する化合物である、発明1乃至3の何れか1つに記載の方法。
有機塩基がトリメチルアミン、トリエチルアミン、ジイソプロピルエチルアミン、トリn-プロピルアミン、トリブチルアミン、又はピリジンである、発明1乃至4の何れか1つに記載の方法。
有機塩基の量が、アンモニア1モルに対して、1モル~50モルであることを特徴とする、発明1乃至5の何れか1つに記載の方法。
ハロゲン化スルフリルもしくはハロゲン化ホスホリルの使用量が、アンモニア1モルに対して、1モル~10モルであることを特徴とする、発明1乃至3の何れか1つに記載の方法。
有機塩基存在下、ハロゲン化スルフリルもしくはハロゲン化ホスホリル、及びアンモニアを反応させる際、反応温度が、-50℃~150℃であることを特徴とする、発明1乃至7の何れか1つに記載の方法。
発明1乃至8の何れか1つに記載の方法で得られた「イミド酸と有機塩基からなる塩又は錯体」に、アルカリ金属の水酸化物もしくは炭酸塩、又はアルカリ土類金属の水酸化物もしくは炭酸塩を反応させることを特徴とする、式[3]で表されるイミド酸金属塩
の製造方法。
FSO2NHSO2NHSO2F
が微量得られることもあるが、簡便な水洗操作により完全に除去することが可能である。
-C=N-C-
を有する化合物であるが、それぞれの化合物の具体的な例を、以下、明示する。
XSO2NHSO2NHSO2X
が微量、生成することがある。その際、簡便な操作(水洗など)により副生成物を除去することが可能である。例えば、本実施例に示すように、水を加えて洗浄する操作は、該目的物である「イミド酸と有機塩基からなる塩又は錯体」の化学純度を向上させるという点でも、好ましい態様の一つである。
以下、実施例により本発明を詳細に説明するが、本発明はこれらの実施例に限定されるものではない。ここで、組成分析値の「%」とは、特に記述のない場合、反応混合物を核磁気共鳴スペクトル(NMR)によって得られた組成の「モル%」を表す。
このように、有機溶媒を実施例3より多く加えることで、収率をより向上させることが可能である。
200mLオートクレーブにアセトニトリルを50g仕込み、氷水で5℃に冷却し、無水アンモニアを12.4g(729 mol)導入した。続いて、フッ化スルフリルを23.3g(228 mmol)導入した。反応器を室温まで昇温させ、48時間攪拌した。この反応液を濾過し、溶媒を留去して、白色固体を10.1 g得た。この白色固体の主成分はスルファミド(H2NSO2NH2)であることを確認し、この白色固体にフルオロスルホニルアミド(FSO2NH2)が3wt%含まれ、ビスフルオロスルホニルイミドアンモニウム塩は、0.3wt%しか含有していなかった。(収率0.1%)
このように、有機塩基を共存させない場合、目的物である該アンモニウム塩が殆ど得られないことがわかる。
200mLオートクレーブにアセトニトリルを50g仕込み、氷水で5℃に冷却し、塩化スルフリルを27.0g(200 mmol)導入した。続いて、無水アンモニアを12.0g(705 mmol)導入した。反応器を室温まで昇温させ、48時間攪拌した。この反応液を濾過し、溶媒を留去して、白色固体を9.8 g得た。この白色固体の主成分はスルファミド(H2NSO2NH2)であることを確認し、この白色固体に、ビス(クロロスルホニル)イミドアンモニウム塩は、含有していなかった。
このように、有機塩基を共存させない場合、目的物である該アンモニウム塩が得られないことがわかる。
Claims (9)
- 式[1]で表される、「イミド酸と有機塩基からなる塩又は錯体」
の製造方法において、有機塩基存在下、ハロゲン化スルフリル(SO2X4X5、:X4、X5は同一、又は異なるハロゲン(フッ素、塩素、臭素、ヨウ素)を表し、前述のX1と同一、又は異なる。)もしくはハロゲン化ホスホリル(P(=O)X6X7X8:X6、X7、X8は同一、又は異なるハロゲン(フッ素、塩素、臭素、ヨウ素)を表し、前述のX2、X3と同一、又は異なる。)と、アンモニアとを反応させることを特徴とする、式[1]で表される、「イミド酸と有機塩基からなる塩又は錯体」の製造方法。 - 有機塩基、及びハロゲン化スルフリルもしくはハロゲン化ホスホリルを反応系内に共存させた後、続けてアンモニアを反応させることにより行うことを特徴とする、請求項1又は2に記載の方法。
- 有機塩基がトリメチルアミン、トリエチルアミン、ジイソプロピルエチルアミン、トリn-プロピルアミン、トリブチルアミン、又はピリジンである、請求項1乃至4の何れか1項に記載の方法。
- 有機塩基の量が、アンモニア1モルに対して、1モル~50モルであることを特徴とする、請求項1乃至5の何れか1項に記載の方法。
- ハロゲン化スルフリルもしくはハロゲン化ホスホリルの使用量が、アンモニア1モルに対して、1モル~10モルであることを特徴とする、請求項1乃至3の何れか1項に記載の方法。
- 有機塩基存在下、ハロゲン化スルフリルもしくはハロゲン化ホスホリル、及びアンモニアを反応させる際、反応温度が、-50℃~150℃であることを特徴とする、請求項1乃至7の何れか1項に記載の方法。
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KR20220135281A (ko) | 2021-03-29 | 2022-10-07 | 주식회사 천보 | 나트륨 비스(플루오로설포닐)이미드의 제조방법 |
CN115140716A (zh) * | 2022-06-17 | 2022-10-04 | 九江天赐高新材料有限公司 | 双(氟磺酰)亚胺化合物的制备方法、双(氟磺酰)亚胺离子液体和双(氟磺酰)亚胺锂 |
CN115140716B (zh) * | 2022-06-17 | 2023-08-29 | 九江天赐高新材料有限公司 | 双(氟磺酰)亚胺化合物的制备方法、双(氟磺酰)亚胺离子液体和双(氟磺酰)亚胺锂 |
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EP2415757A4 (en) | 2013-04-10 |
CN102378755A (zh) | 2012-03-14 |
JP5630048B2 (ja) | 2014-11-26 |
EP2415757B1 (en) | 2014-07-23 |
US8815199B2 (en) | 2014-08-26 |
EP2415757A1 (en) | 2012-02-08 |
KR101317294B1 (ko) | 2013-10-14 |
JP2010254554A (ja) | 2010-11-11 |
US20120020867A1 (en) | 2012-01-26 |
CN102378755B (zh) | 2014-04-16 |
KR20110130505A (ko) | 2011-12-05 |
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