WO2011148971A1 - Procédé pour la préparation de composés sulfonylimide contenant du fluor - Google Patents

Procédé pour la préparation de composés sulfonylimide contenant du fluor Download PDF

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Publication number
WO2011148971A1
WO2011148971A1 PCT/JP2011/061964 JP2011061964W WO2011148971A1 WO 2011148971 A1 WO2011148971 A1 WO 2011148971A1 JP 2011061964 W JP2011061964 W JP 2011061964W WO 2011148971 A1 WO2011148971 A1 WO 2011148971A1
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Prior art keywords
fluorine
compound
sulfonic acid
formula
mixture
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PCT/JP2011/061964
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English (en)
Japanese (ja)
Inventor
博之 八柳
武志 神谷
常俊 本田
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三菱マテリアル株式会社
三菱マテリアル電子化成株式会社
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Publication of WO2011148971A1 publication Critical patent/WO2011148971A1/fr

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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
    • C07C303/42—Separation; Purification; Stabilisation; Use of additives
    • C07C303/44—Separation; Purification

Definitions

  • the present invention relates to an improvement in a method for producing a fluorine-containing sulfonylimide compound, and particularly relates to purification of a fluorine-containing sulfonylimide compound.
  • Fluorine-containing sulfonylimide compounds are known to be useful substances as ion conducting materials and anion sources for ionic liquids.
  • Ionic liquids are particularly expected as electrolytes for batteries and capacitors, reaction solvents, catalysts, and the like.
  • a salt of a fluorine-containing sulfonylimide acid that is a fluorinated imide compound
  • a halide salt of a quaternary amine such as an imidazolium bromide salt.
  • Patent Documents 1 and 2 are known as a method for producing such a fluorinated sulfonylimide compound. Specifically, in Patent Document 1, as shown in the following formula (A), perfluoroalkylsulfonamide (Rf a SO 2 NH 2 ), perfluoroalkyl sulfonyl halide (Rf b SO 2 X), and potassium fluoride And a fluorine compound (MF) such as acetonitrile are reacted in an organic solvent such as acetonitrile to produce a perfluoroalkylsulfonimide salt ((Rf a SO 2 ) (Rf b SO 2 ) N ⁇ M). ing.
  • A perfluoroalkylsulfonamide
  • Rf b SO 2 X perfluoroalkyl sulfonyl halide
  • MF perfluorine compound
  • MF perfluorine compound
  • Rf a and Rf b represent a perfluoroalkyl group or the like
  • M represents an alkali metal or the like
  • X represents fluorine or chlorine, respectively.
  • Patent Document 2 in the following formula (B), in the presence of a tertiary amine or a heterocyclic amine (NR 1 R 2 R 3 ), a perfluoroalkylsulfonamide, a perfluoroalkylsulfonyl halide, Is reacted to produce a perfluoroalkylsulfonimide salt ((Rf c SO 2 ) (Rf d SO 2 ) N ⁇ M).
  • Rf c and Rf d represent a perfluoroalkyl group or the like, and R 1 to R 3 represent an alkyl group or the like.
  • Patent Document 3 discloses that a sulfonic acid compound is by-produced as an impurity in the process of producing a fluorine-containing sulfonylimide compound.
  • Patent Document 6 discloses that in the process of producing a fluorine-containing sulfonylimide salt, if a small amount of water is present, a sulfonate is by-produced.
  • the by-product of the sulfonic acid compound is inevitable. is the current situation.
  • a fluorine-containing sulfonylimide compound is produced by reacting a sulfonamide compound and a sulfonyl halide
  • the sulfonic acid compound by-produced during the production of the sulfonamide compound may be brought into the imidization reaction together with the sulfonamide compound. is there.
  • Patent Documents 4 to 6 are known as methods for purifying such a fluorinated sulfonylimide compound.
  • Patent Document 4 discloses a purification method in which 1,4-dioxane is added to a sulfonimide lithium salt and recrystallization is performed.
  • Patent Document 5 discloses a method of recrystallizing or washing a sulfonimide ammonium salt with an aqueous sodium hydroxide solution.
  • Patent Document 6 discloses a method in which a sulfonimide salt is mixed with a mixed solvent of a hydrophobic organic solvent and water and stirred, then the aqueous layer is separated, and the organic layer is concentrated and dried.
  • Patent Document 4 is not an industrially advantageous method because a large amount of solvent (1,4-dioxane) is used and recrystallization needs to be repeated. .
  • solvent (1,4-dioxane)
  • Patent Document 5 since ammonia is liberated, it is necessary to control the concentration of the aqueous sodium hydroxide solution.
  • the recrystallization needs to be repeated and the operation is complicated.
  • the amount of the target sulfonimide salt dissolved in the aqueous layer is large and the loss is large. Therefore, it has been necessary to repeatedly extract using a hydrophobic organic solvent.
  • the present invention has been made in view of the above circumstances, and an object of the present invention is to provide a method for producing a fluorine-containing sulfonylimide compound that can be purified in a high yield by a simple operation.
  • the present inventors have intensively studied. As a result, when water is added to a mixture of a fluorine-containing sulfonylimide acid and a sulfonic acid, the sulfonic acid forms a hydrate and the boiling point increases greatly. On the other hand, it was confirmed that the fluorine-containing sulfonylimide acid did not form a hydrate. And it discovered that the fluorine-containing sulfonyl imide acid and sulfonic acid could be efficiently isolate
  • a method for producing a fluorine-containing sulfonylimide compound according to one embodiment of the present invention comprises a mixture of a fluorine-containing sulfonylimide compound represented by the following formula (1) and a sulfonic acid compound represented by the following formula (2). Distill in the presence of water. (Rf 1 SO 2 ) (Rf 2 SO 2 ) NH (1) RfSO 3 H (2) However, in the above formula (1), Rf 1 and Rf 2 are fluorine or a linear or branched perfluoroalkyl group having 1 to 4 carbon atoms, and a combination in which Rf 1 and Rf 2 are both fluorine. except for. In the above formula (2), Rf is a linear or branched perfluoroalkyl group having 1 to 4 carbon atoms.
  • water may be added to the mixture so that a molar ratio of the water to the sulfonic acid compound is 1 or more.
  • Rf 1 and Rf 2 are fluorine or a linear or branched perfluoroalkyl group having 1 to 4 carbon atoms, and a combination in which Rf 1 and Rf 2 are both fluorine. except for.
  • Rf is a linear or branched perfluoroalkyl group having 1 to 4 carbon atoms.
  • M is at least one selected from alkali metal elements, alkaline earth metal elements, and onium ions.
  • the acidic solution may be an aqueous sulfuric acid solution.
  • the fluorine-containing sulfonylimide acid and the sulfonic acid are obtained by distilling the fluorine-containing sulfonylimide compound and the sulfonic acid compound in the presence of water. It becomes possible to separate and purify efficiently. Therefore, it is possible to provide a method for producing a fluorine-containing sulfonylimide compound that can be purified with high yield by a simple operation.
  • Rf 1 SO 2 (Rf 1 SO 2 ) (Rf 2 SO 2 ) NH (5)
  • Rf 1 and Rf 2 are fluorine or a linear or branched perfluoroalkyl group having 1 to 4 carbon atoms
  • Rf 1 and Rf 2 are both fluorine.
  • Rf is a linear or branched perfluoroalkyl group having 1 to 4 carbon atoms.
  • perfluoroalkylsulfonimides which are fluorine-containing sulfonylimide compounds represented by the formula (5)
  • Rf 1 and Rf 2 are the same (symmetric structure)
  • bis (trifluoromethanesulfonyl) imide [(CF 3 SO 2) 2 NH]
  • bis (pentafluoroethane sulfonyl) imide [(C 2 F 5 SO 2 ) 2 NH]
  • bis (heptafluoropropanesulfonyl) imide (C 3 F 7 SO 2 ) 2 NH]
  • perfluoroalkylsulfonimides such as bis (nonafluorobutanesulfonyl) imide [(C 4 F 9 SO 2 ) 2 NH].
  • Rf 1 and Rf 2 of the present embodiment when the number of carbon atoms is 3 or 4, branched structural isomers are included in addition to the straight chain (in Rf 1 and Rf 2 described below) Is the same).
  • fluorine-containing sulfonylimide compounds represented by the formula (5) perfluoroalkylsulfonimide
  • Rf 1 and Rf 2 are different (asymmetric structure) is trifluoro-N- (fluorosulfonyl) methanesulfonyl Amide [(FSO 2 ) (CF 3 SO 2 ) NH]
  • pentafluoro-N- (fluorosulfonyl) ethanesulfonylamide [(FSO 2 ) (C 2 F 5 SO 2 ) NH]
  • nonafluoro-N- (fluorosulfonyl) butanesulfonylamide [(FSO 2 ) (C 4 F 9 SO 2 ) NH]
  • perfluoroalkylsulfonic acids that are sulfonic acid compounds represented by formula (6) include trifluoromethylsulfonic acid (CF 3 SO 3 H), pentafluoroethylsulfonic acid (C 2 F 5 SO 3 H), heptafluoro Examples thereof include propyl sulfonic acid (C 3 F 7 SO 3 H) and nonafluorobutyl sulfonic acid (C 4 F 9 SO 3 H).
  • a fluorine-containing sulfonylimide compound salt represented by the following formula (7) is produced. Specifically, perfluoroalkylsulfonyl fluoride (one of Rf 1 SO 2 F and Rf 2 SO 2 F) is dropped into an aqueous ammonia solution, and perfluoroalkylsulfonamide (Rf 1 SO 2 NH 2 and Rf 2 is added). One of SO 2 NH 2 is synthesized.
  • an alkali metal or alkaline earth metal hydroxide aqueous solution or an aqueous solution containing an onium compound is added to the reaction solution of perfluoroalkylsulfonamide ( one of Rf 1 SO 2 NH 2 and Rf 2 SO 2 NH 2 ). And concentrate to make a concentrate.
  • the concentrate is reacted with perfluoroalkylsulfonyl fluoride (the other of Rf 1 SO 2 F and Rf 2 SO 2 F) in a solvent such as acetonitrile to produce a perfluoroalkylsulfonylimide compound salt (fluorinated sulfonylimide).
  • Compound salt is synthesized.
  • a sulfonic acid compound salt represented by the following formula (8) is by-produced as an impurity.
  • Rf 1 SO 2 (Rf 2 SO 2 ) N ⁇ M (7)
  • Rf 1 and Rf 2 are fluorine or a linear or branched perfluoroalkyl group having 1 to 4 carbon atoms
  • Rf 1 and Rf 2 are both fluorine.
  • Rf is a linear or branched perfluoroalkyl group having 1 to 4 carbon atoms.
  • M is one or more selected from alkali metal elements, alkaline earth metal elements, and onium ions.
  • the alkali metal element include lithium (Li), sodium (Na), potassium (K), and the like.
  • the alkaline earth metal element include calcium (Ca), strontium (Sr), barium (Ba), and the like.
  • an onium ion for example, a compound containing a lone electron pair such as nitrogen, sulfur, oxygen, phosphorus, selenium, tin, iodine, and antimony is obtained by coordination of a cation type atomic group, Any cation having at least one organic group may be used without particular limitation.
  • perfluoroalkylsulfonimide salts which are fluorine-containing sulfonylimide compound salts represented by the formula (7)
  • bis (trifluoromethanesulfonyl) Imide salt [(CF 3 SO 2 ) 2 N ⁇ M]
  • bis (pentafluoroethanesulfonyl) imide salt [(C 2 F 5 SO 2 ) 2 N ⁇ M]
  • bis (heptafluoropropanesulfonyl) imide salt [( C 3 F 7 SO 2 ) 2 N ⁇ M]
  • bis (nonafluorobutanesulfonyl) imide salt [(C 4 F 9 SO 2 ) 2 N ⁇ M]
  • other perfluoroalkylsulfonimide salts represented by the formula (7)
  • Rf 1 and Rf 2 of the present embodiment when the number of carbon atoms is 3 or 4, branched structural isomers are included in addition to the straight chain (in Rf 1 and Rf 2 described below) Is the same).
  • fluorine-containing sulfonylimide compound salts represented by the formula (7)
  • Rf 1 and Rf 2 are different (asymmetric structure)
  • trifluoro-N- (fluorosulfonyl) methane Sulfonylamide salts [(FSO 2 ) (CF 3 SO 2 ) N ⁇ M]
  • pentafluoro-N- (fluorosulfonyl) ethanesulfonylamide salts [(FSO 2 ) (C 2 F 5 SO 2 ) N ⁇ M]
  • Heptafluoro-N- (fluorosulfonyl) propanesulfonylamide salt [(FSO 2 ) (C 3 F 7 SO 2 ) N ⁇ M]
  • nonafluoro-N- (fluorosulfonyl) butanesulfonylamide salt [(FSO 2 ) (C 4 F 9 SO 2) N ⁇ M]
  • perfluoroalkyl sulfonates that are sulfonic acid compound salts represented by formula (8) include trifluoromethyl sulfonate (CF 3 SO 3 ⁇ M), pentafluoroethyl sulfonate (C 2 F 5 SO 3). ⁇ M), heptafluoropropyl sulfonate (C 3 F 7 SO 3 ⁇ M), nonafluorobutyl sulfonate (C 4 F 9 SO 3 ⁇ M) and the like.
  • an acidic solution is added to a mixture of the fluorinated sulfonylimide compound salt represented by the formula (7) and the sulfonic acid compound salt represented by the formula (8), and the mixture is adjusted (prepared). .
  • an acidic solution from the fluorine-containing sulfonylimide compound salt represented by the formula (7) and the sulfonic acid compound salt represented by the formula (8), the fluorine-containing sulfonylimide compound represented by the formula (5) and the formula The sulfonic acid compound shown in (6) is produced.
  • the molar ratio of the acidic solution to the fluorine-containing sulfonylimide compound salt and the sulfonic acid compound salt is preferably 1 or more, and more preferably 1 to 10.
  • the stirring temperature of the mixed liquid is not particularly limited, but is preferably room temperature or higher, and more preferably 50 to 200 ° C. Thereby, reaction can be advanced in a short time.
  • Examples of the acidic solution include a fluorine-containing sulfonylimide compound represented by the formula (7) and a sulfonic acid compound salt represented by the formula (8). If it can produce
  • Examples of such an acidic solution include a hydrochloric acid aqueous solution, a nitric acid aqueous solution, and a sulfuric acid aqueous solution, and a sulfuric acid aqueous solution, and a sulfuric acid aqueous solution is particularly preferable.
  • the amount of water in which the molar ratio of water to the sulfonic acid compound represented by formula (6) is 1 or more in the adjusted mixed solution It is preferable to adjust the addition amount of the acidic solution so as to exist. Thereby, the whole quantity of the sulfonic acid compound in a liquid mixture can be hydrated.
  • the molar ratio of water to sulfonic acid compound is preferably 10 to 1000.
  • the mixed solution is distilled in a state where the mixed solution contains water. Since the mixed solution contains water, the mixture of the fluorine-containing sulfonylimide compound represented by the formula (5) and the sulfonic acid compound represented by the formula (6) is distilled in the presence of water. . It is preferable to distill the mixed solution in a state where water is contained in an amount such that the molar ratio of water to the sulfonic acid compound is 1 or more. For this reason, it is preferable to add water to a liquid mixture so that the molar ratio of the water with respect to a sulfonic acid compound may be 1 or more in a liquid mixture.
  • the whole quantity of the sulfonic acid compound in a liquid mixture can be hydrated.
  • the molar ratio of water to sulfonic acid compound is preferably 10 to 1000.
  • the optimum distillation method, temperature conditions, etc. are appropriately determined according to the mixture of the fluorine-containing sulfonylimide compound represented by the formula (5) and the sulfonic acid compound represented by the formula (6), which is the separation target. select. Specifically, when a mixture of the fluorine-containing sulfonylimide compound represented by the formula (5) and the sulfonic acid compound represented by the formula (6) is distilled in the presence of water, the sulfone represented by the formula (6) is represented. The acid compound forms a hydrate and the boiling point rises greatly. In consideration of this, a distillation method (for example, vacuum distillation or the like) and temperature conditions are determined.
  • a distillation method for example, vacuum distillation or the like
  • distillation temperature is in the range of 50 ° C. to 200 ° C. and the degree of vacuum is in the range of 1 to 200 torr (0.13 to 27 kPa)
  • distillation can be performed for all the specific examples of the fluorine-containing sulfonylimide compound described above. Can be separated.
  • the fluorinated sulfonylimide compound represented by the formula (5) is bis (trifluoromethanesulfonyl) imide [(CF 3 SO 2 ) 2 NH], and the sulfonic acid of the formula (6) contained as an impurity
  • the compounds are trifluoromethylsulfonic acid (CF 3 SO 3 H)
  • the boiling points of the respective compounds are 163 ° C.
  • the fluorinated sulfonylimide compound represented by the formula (5) is bis (trifluoromethanesulfonyl) imide [(CF 3 SO 2 ) 2 NH], and the sulfonic acid of the formula (6) contained as an impurity
  • the compound is trifluoromethyl sulfonic acid (CF 3 SO 3 H)
  • the sulfonic acid compound becomes a hydrate and its boiling point rises to about 260 ° C. Since the difference in boiling point between the fluorine-containing sulfonylimide compound and the hydrate of the sulfonic acid compound is large, a high-purity fluorine-containing sulfonylimide compound can be purified.
  • the fluorine-containing sulfonylimide acid and the sulfone compound are distilled by distilling the fluorine-containing sulfonylimide compound and the sulfonic acid compound in the presence of water. It is possible to efficiently separate and purify the acid. Therefore, it is possible to provide a method for producing a fluorine-containing sulfonylimide compound that can be purified with high yield by a simple operation.
  • Example 1 ⁇ Synthesis of (C 3 F 7 SO 2 ) 2 NK> A 1 L flask is charged with 500 g of 20% aqueous ammonia, 300 g of heptafluoropropanesulfonyl fluoride (C 3 F 7 SO 2 F) is added dropwise at 40 ° C., and heptafluoropropane sulfonamide (C 3 F 7 SO 2 NH) is added. 2 ) was synthesized. Thereafter, 280 g of 48% potassium hydroxide (KOH) aqueous solution was added to the reaction solution, and the mixture was concentrated.
  • KOH potassium hydroxide
  • the white crystals were obtained from 86 g of bis (heptafluoropropanesulfonyl) imide potassium salt ((C 3 F 7 SO 2 ) 2 NK) and heptafluoropropanesulfonic acid. It was found to be a mixture of 17 g of potassium salt (C 3 F 7 SO 3 K).
  • Table 1 shows the addition amount and generation amount of each compound of Example 1, the amount of water in the sulfuric acid aqueous solution, and the molar ratio of water to the sulfonic acid compound.
  • Example 2 According to the same production method as in Example 1, except that trifluoromethanesulfonyl fluoride (CF 3 SO 2 F) was used instead of heptafluoropropanesulfonyl fluoride (C 3 F 7 SO 2 F) as a raw material, 60 g of a mixture of (romethanesulfonyl) imide potassium salt ((CF 3 SO 2 ) 2 NK) and potassium trifluoromethanesulfonate (CF 3 SO 3 K) was obtained. The content of potassium trifluoromethanesulfonate (CF 3 SO 3 K) in this mixture was 10% by weight.
  • a high-purity fluorine-containing sulfonylimide compound can be produced (purified) with high yield by a simple operation.
  • the manufacturing method of the fluorine-containing sulfonylimide compound which concerns on 1 aspect of this invention can be applied suitably to the manufacturing process of a fluorine-containing sulfonylimide compound useful as an anion source of an ion conductive material or an ionic liquid.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé pour la préparation de composés sulfonylimide contenant du fluor, qui comprend la soumission d'un mélange d'un composé sulfonylimide contenant du fluor représenté par (Rf1SO2)(Rf2SO2)NH (1) et un composé acide sulfonique représenté par RfSO3H (2) à une distillation en présence d'eau. Dans la formule (1), Rf1 et Rf2 représentent, chacun, fluor ou C1-4-perfluoroalkyle linéaire ou ramifié, à condition que le cas dans lequel Rf1 et Rf2 représentent tous les deux fluor soit exclus. Dans la formule (2), Rf représente C1-4 perfluoroalkyle linéaire ou ramifié.
PCT/JP2011/061964 2010-05-26 2011-05-25 Procédé pour la préparation de composés sulfonylimide contenant du fluor WO2011148971A1 (fr)

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JP2010120658A JP2011246385A (ja) 2010-05-26 2010-05-26 含フッ素スルホニルイミド化合物の製造方法
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140012881A (ko) * 2012-07-23 2014-02-04 로디아 오퍼레이션스 설폰이미드 화합물 및 그 염들의 제조 방법
CN108147981A (zh) * 2016-12-06 2018-06-12 中国科学院宁波材料技术与工程研究所 一种逆相转移催化制备磺酰亚胺类化合物的方法
US11267707B2 (en) 2019-04-16 2022-03-08 Honeywell International Inc Purification of bis(fluorosulfonyl) imide

Families Citing this family (1)

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Publication number Priority date Publication date Assignee Title
JP6703256B2 (ja) * 2016-03-15 2020-06-03 セントラル硝子株式会社 撥水性保護膜形成剤、撥水性保護膜形成用薬液、及びウェハの洗浄方法

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JPH1017541A (ja) * 1996-07-04 1998-01-20 Asahi Chem Ind Co Ltd ビスパーフルオロアルキルスルホニルイミドおよびその製造方法
JP2004059533A (ja) * 2002-07-31 2004-02-26 Asahi Kasei Corp ビススルホニルイミド基含有モノマーの製造方法

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140012881A (ko) * 2012-07-23 2014-02-04 로디아 오퍼레이션스 설폰이미드 화합물 및 그 염들의 제조 방법
JP2015528806A (ja) * 2012-07-23 2015-10-01 ローディア オペレーションズ スルホンイミド化合物およびその塩の製造方法
KR101961779B1 (ko) 2012-07-23 2019-03-25 로디아 오퍼레이션스 설폰이미드 화합물 및 그 염들의 제조 방법
CN108147981A (zh) * 2016-12-06 2018-06-12 中国科学院宁波材料技术与工程研究所 一种逆相转移催化制备磺酰亚胺类化合物的方法
US11267707B2 (en) 2019-04-16 2022-03-08 Honeywell International Inc Purification of bis(fluorosulfonyl) imide

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