WO2014024682A1 - ビス(ハロスルホニル)アミンの製造方法 - Google Patents
ビス(ハロスルホニル)アミンの製造方法 Download PDFInfo
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- WO2014024682A1 WO2014024682A1 PCT/JP2013/070029 JP2013070029W WO2014024682A1 WO 2014024682 A1 WO2014024682 A1 WO 2014024682A1 JP 2013070029 W JP2013070029 W JP 2013070029W WO 2014024682 A1 WO2014024682 A1 WO 2014024682A1
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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
- C01B21/087—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
- C01B21/086—Compounds containing nitrogen and non-metals and optionally metals containing one or more sulfur atoms
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0566—Liquid materials
- H01M10/0567—Liquid materials characterised by the additives
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0566—Liquid materials
- H01M10/0568—Liquid materials characterised by the solutes
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Definitions
- the present invention relates to a method for producing bis (halosulfonyl) amine. More specifically, the present invention controls the reaction rate of sulfamic acid, halogenating agent, and halosulfonic acid to be almost constant from the beginning of the reaction to the end of the reaction, thereby suppressing the rapid generation of gas and the amount of the halogenating agent used.
- the present invention relates to a process for producing bis (halosulfonyl) amine, which is advantageous for industrial production. This application claims priority on August 6, 2012 based on Japanese Patent Application No. 2012-174209 for which it applied to Japan, and uses the content here.
- Bis (fluorosulfonyl) amine salts are useful compounds in various fields such as battery electrolytes, additives to battery electrolytes, and conductive coating materials (Patent Document 1, Patent Document 2, and Patent Document 3).
- Bis (chlorosulfonyl) amine can be converted into various bis (fluorosulfonyl) amine salts by reacting with a fluorinating agent or by performing a cation exchange reaction after reacting with a fluorinating agent. Therefore, it is a useful compound (Patent Document 4, Patent Document 5, Non-Patent Document 1).
- Patent Document 3 Patent Document 4, Patent Document. 6, Non-Patent Document 2, Non-Patent Document 3).
- An object of the present invention is to control the reaction rate of sulfamic acid, halogenating agent, and halosulfonic acid to be almost constant from the beginning of the reaction to the end of the reaction, thereby suppressing rapid gas generation and reducing the amount of halogenating agent used. It is to provide a process for producing bis (halosulfonyl) amine which is advantageous for industrial production.
- the present invention includes the following.
- a method for producing bis (halosulfonyl) amine which comprises heating a mixture containing sulfamic acid and halosulfonic acid to a temperature higher than room temperature and then adding a halogenating agent thereto.
- the production method according to (1) wherein the temperature higher than room temperature is 50 ° C. to 140 ° C.
- the reaction rate of the sulfamic acid, the halogenating agent and the halosulfonic acid is controlled to be substantially constant from the initial reaction to the final reaction, thereby suppressing the rapid generation of gas and reducing the amount of the halogenating agent used. Since it can be reduced, it is advantageous for industrial production of bis (halosulfonyl) amine. Moreover, according to the production method of the present invention, bis (halosulfonyl) amine can be produced in a high yield, which is advantageous for industrial production.
- a method for producing bis (halosulfonyl) amine according to an embodiment of the present invention includes heating a mixture containing sulfamic acid and halosulfonic acid to a temperature higher than room temperature, and then adding a halogenating agent thereto. .
- bis (halosulfonyl) amine is a compound represented by Formula (3).
- X in Formula (3) shows a halogen atom. X may be the same or different.
- Specific examples of bis (halosulfonyl) amine include N- (fluorosulfonyl) -N- (chlorosulfonyl) amine and bis (chlorosulfonyl) amine.
- the sulfamic acid used in the present invention is a known substance represented by the formula (1).
- a commercially available sulfamic acid may be used.
- the sulfamic acid is preferably one that is dried before being subjected to the reaction to remove contained water.
- the method of a drying process is not specifically limited, Generally used methods, such as heat drying and reduced pressure drying, can be mentioned.
- the halosulfonic acid used in the present invention is a known substance represented by the formula (2).
- X in Formula (2) shows a halogen atom.
- a commercially available halosulfonic acid may be used.
- the halosulfonic acid is preferably one that is dried before being subjected to the reaction to remove the contained water. Although the method of a drying process is not specifically limited, Generally used methods, such as heat drying and reduced pressure drying, can be mentioned.
- As the halosulfonic acid fluorosulfonic acid and chlorosulfonic acid are preferable, and chlorosulfonic acid is more preferable.
- the halogenating agent used in the present invention is not particularly limited, and commercially available products can be used.
- the halogenating agent is preferably one that is dried before being subjected to the reaction to remove the contained water.
- the method of a drying process is not specifically limited, Generally used methods, such as heat drying and reduced pressure drying, can be mentioned.
- the halogenating agent include phosphorus trichloride, phosphorus pentachloride, thionyl chloride, thionyl fluoride, and the like. From the viewpoint of easy purification after completion of the reaction, thionyl chloride is preferable.
- the molar ratio of halosulfonic acid to sulfamic acid is preferably 0.9 to 1.2, more preferably 0.95 to 1.05.
- the mixture may optionally contain a solvent for dissolving or dispersing them.
- the solvent is not particularly limited as long as it does not inhibit the reaction of sulfamic acid, halogenating agent and halosulfonic acid, but is preferably a compound having no aromatic proton.
- the mixture containing sulfamic acid and halosulfonic acid is heated before adding the halogenating agent.
- the heated mixture has a temperature at the time of adding the halogenating agent higher than room temperature, preferably 50 to 140 ° C., more preferably 60 to 80 ° C. By adjusting to such a temperature, it is possible to prevent gas from being generated abruptly.
- the addition amount of the halogenating agent is not particularly limited.
- the addition amount of the halogenating agent with respect to 1 mol of sulfamic acid is preferably 2 to 4 mol, more preferably 2 to 3 mol.
- the addition amount of the halogenating agent is less than 2 mol, the yield and purity tend to decrease.
- the method of adding the halogenating agent is not particularly limited, but it may be added gradually gradually, may be added gradually, or may be added in several steps at intervals. Also good. In the case of continuous or intermittent addition, it is preferable to keep the addition rate low in order to prevent a rapid increase in the reaction rate.
- the addition rate can be appropriately set depending on the scale of the reactor and the set reaction temperature. When adding in several times, in order to prevent a rapid increase in reaction rate, it is preferable to keep the amount added at a time low. The amount to be added at a time can be appropriately set depending on the scale of the reactor and the set reaction temperature.
- the temperature of the mixture after adding the halogenating agent can be variously set in order to control the scale of the reactor and the desired reaction rate, and is usually higher than room temperature, preferably 50 to 140 ° C., more preferably 60 ° C. ⁇ 80 ° C.
- the temperature of the mixture after adding the halogenating agent can be set to, for example, 50 ° C. to 85 ° C., 86 ° C. to 105 ° C., or 106 ° C. to 140 ° C. Can do.
- reaction time is not specifically limited, Usually, it is 48 hours or less, Preferably it is 24 hours or less.
- the reaction can be performed in the presence of a catalyst.
- the catalyst is preferably a basic catalyst.
- Base catalysts include aliphatic tertiary amine compounds such as trimethylamine, triethylamine, tripropylamine, tributylamine, tri (hydroxyethyl) amine, methylpiperidine, dimethylpiperazine, diazabicyclooctane; trimethylphosphine, triethylphosphine, etc. Of trialkylphosphine.
- the amount of the catalyst used is preferably 0.0001 to 0.1 mol with respect to 1 mol of sulfamic acid.
- the catalyst may be added to the mixture before the halogenating agent is added, may be added simultaneously with the addition of the halogenating agent, or may be added after the halogenating agent is added. Of these, the method of charging the mixture before adding the halogenating agent is preferred.
- Non-Patent Document 3 for example, sulfamic acid, halogenating agent, and halosulfonic acid seem to cause a reaction represented by the reaction formula (A) or (B).
- the reaction rate of sulfamic acid, halogenating agent, and halosulfonic acid can be controlled to be almost constant from the initial reaction stage to the final reaction stage, thereby suppressing the rapid generation of gas.
- Example 1 A 500 ml reaction vessel equipped with a stirrer, a thermometer and a reflux tube was charged with 97.1 g (1.00 mol) of sulfamic acid and 121.2 g (1.04 mol) of chlorosulfonic acid to obtain a mixed solution. The mixture was heated to 70 ° C. with stirring. Next, 237.9 g (2.00 mol) of thionyl chloride was added dropwise thereto over 1 hour. Subsequently, the reaction was carried out at 70 ° C. for 6 hours. The temperature was then raised to 80 ° C. over 0.5 hours. Thereafter, 119.0 g (1.00 mol) of thionyl chloride was added dropwise over 1 hour.
- Example 2 In a 2000 ml reaction vessel equipped with a stirrer, a thermometer and a reflux tube, 268.0 g (2.76 mol) of sulfamic acid and 334.5 g (2.87 mol) of chlorosulfonic acid were added and stirred to obtain a mixed solution. The mixture was heated to 70 ° C. with stirring. Next, 656.7 g (5.52 mol) of thionyl chloride was added dropwise thereto over 1.5 hours. Subsequently, the reaction was carried out at 70 ° C. for 6 hours. Thereafter, 131.3 g (1.10 mol) of thionyl chloride was added dropwise over 0.2 hours. Next, the temperature was raised to 90 ° C.
- Comparative Example 1 In a 500 ml reaction vessel equipped with a stirrer, thermometer and reflux tube, 9.71 g (0.10 mol) sulfamic acid, 12.12 g (0.104 mol) chlorosulfonic acid, and 29.74 g (0.25 mol) thionyl chloride. ) And stirred to obtain a mixed solution. The mixture was heated with stirring to raise the temperature to 70 ° C. and then reacted at 70 ° C. for 4 hours. The temperature was raised to 130 ° C. over 2 hours and reacted at 130 ° C. for 2 hours. Gas was rapidly generated while the temperature was raised to 130 ° C. The resulting reaction solution was distilled under reduced pressure.
- the reaction rate of the sulfamic acid, the halogenating agent and the halosulfonic acid is controlled to be substantially constant from the initial reaction to the final reaction, thereby suppressing the rapid generation of gas and reducing the amount of the halogenating agent used. Since it can be reduced, it is advantageous for industrial production of bis (halosulfonyl) amine.
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
本願は、2012年8月6日に、日本に出願された特願2012-174209号に基づき優先権を主張し、その内容をここに援用する。
すなわち、本発明は、以下のものを包含する。
(1)スルファミン酸とハロスルホン酸を含む混合物を加熱して室温より高い温度にし、次いでこれにハロゲン化剤を添加することを含む、ビス(ハロスルホニル)アミンの製造方法。
(2)室温より高い温度が50℃~140℃である(1)に記載の製造方法。
(3)ハロゲン化剤を複数回に分けて添加する(1)または(2)に記載の製造方法。
(4)ハロゲン化剤が塩化チオニルである(1)~(3)いずれか1項に記載の製造方法。
(5)スルファミン酸1モルに対し、塩化チオニル2~3モルを用いる(4)に記載の製造方法。
(6)ハロゲン化剤を添加した後、混合物の温度を50℃~85℃にて反応させることをさらに含む(1)~(5)いずれか1項に記載の製造方法。
(7)ハロゲン化剤を添加した後、混合物の温度を86℃~105℃にて反応させることをさらに含む(1)~(5)いずれか1項に記載の製造方法。
(8)ハロゲン化剤を添加した後、混合物の温度を106℃~140℃にて反応させることをさらに含む(1)~(5)いずれか1項に記載の製造方法。
該混合物はスルファミン酸およびハロスルホン酸以外にそれらを溶解または分散するための溶剤を必要に応じて含んでいてもよい。溶剤はスルファミン酸とハロゲン化剤とハロスルホン酸との反応を阻害しないものであれば特に制限されないが、好ましくは芳香族プロトンを持たない化合物である。
連続的または断続的に添加する場合には、急激な反応速度の増大を防ぐために、添加速度を低く抑えることが好ましい。添加速度は、反応器の規模、設定した反応温度により、適宜設定することができる。複数回に分けて添加する場合は、急激な反応速度の増大を防ぐために、1度に添加する量を低く抑えることが好ましい。1度に添加する量は、反応器の規模、設定した反応温度により、適宜設定することができる。
反応時間は特に限定されないが、通常、48時間以下であり、好ましくは24時間以下である。
触媒は、ハロゲン化剤を添加する前に混合物に仕込んでもよいし、ハロゲン化剤の添加と同時に添加してもよいし、ハロゲン化剤を添加した後に添加してもよい。これらのうち、ハロゲン化剤を添加する前に混合物に仕込んでおく方法が好ましい。
これに対して、本発明の方法によると、スルファミン酸とハロゲン化剤とハロスルホン酸との反応速度を反応初期から反応終期までほぼ一定に制御して、ガスの急激な発生を抑えることができる。
攪拌器、温度計および還流管を取り付けた500mlの反応容器に、スルファミン酸97.1g(1.00mol)およびクロロスルホン酸121.2g(1.04mol)を入れ撹拌して混合液を得た。この混合液を撹拌下に加熱して70℃にした。次いで、これに塩化チオニル237.9g(2.00mol)を1時間かけて滴下した。引き続き70℃にて6時間反応させた。 次いで0.5時間かけて温度を80℃に上げた。その後、塩化チオニル119.0g(1.00mol)を1時間かけて滴下した。次いで1.9時間かけて温度を90℃に上げ、引き続き90℃にて4時間反応させた。
その後、温度を130℃に上げ、130℃にて2時間反応させた。このときに未反応の塩化チオニルが蒸発し系外に排出された。
上記の反応中にガスの急激な発生はなかった。
得られた反応液を減圧蒸留した。105℃以上/7torrの留分として無色透明の液状物〔ビス(クロロスルホニル)アミン〕206.6g(0.97mol、スルファミン酸基準の収率97%、塩化チオニル基準の収率32%)を得た。
攪拌器、温度計および還流管を取り付けた2000mlの反応容器に、スルファミン酸268.0g(2.76mol)およびクロロスルホン酸334.5g(2.87mol)を入れ撹拌して混合液を得た。この混合液を撹拌下に加熱して70℃にした。次いで、これに塩化チオニル656.7g(5.52mol)を1.5時間かけて滴下した。引き続き70℃にて6時間反応させた。 その後、塩化チオニル131.3g(1.10mol)を0.2時間かけて滴下した。次いで3時間かけて温度を90℃に上げ、引き続き90℃にて4時間反応させた。
その後、温度を130℃に上げ、130℃にて2時間反応させた。このときに未反応の塩化チオニルが蒸発し系外に排出された。
上記の反応中にガスの急激な発生はなかった。
得られた反応液を減圧蒸留した。100℃以上/7.5torrの留分として無色透明の液状物〔ビス(クロロスルホニル)アミン〕553.6g(2.59mol、スルファミン酸基準の収率94%、塩化チオニル基準の収率39.1%)を得た。
攪拌器、温度計および還流管を取り付けた500mlの反応容器に、スルファミン酸9.71g(0.10mol)、クロロスルホン酸12.12g(0.104mol)、および塩化チオニル29.74g(0.25mol)を入れ撹拌して混合液を得た。この混合液を撹拌下に加熱して温度を70℃に上げ、引き続き70℃で4時間反応させた。
2時間かけて温度を130℃に上げ、130℃にて2時間反応させた。130℃に温度を上げている最中にガスが急激に発生した。
得られた反応液を減圧蒸留した。110℃以上/7torrの留分として無色透明の液状物〔ビス(クロロスルホニル)アミン〕7.74g(0.036mol、スルファミン酸基準の収率36%、塩化チオニル基準の収率14.4%)を得た。
Claims (8)
- スルファミン酸とハロスルホン酸を含む混合物を加熱して室温より高い温度にし、次いでこれにハロゲン化剤を添加することを含む、ビス(ハロスルホニル)アミンの製造方法。
- 室温より高い温度が50℃~140℃である請求項1に記載の製造方法。
- ハロゲン化剤を複数回に分けて添加する請求項1または2に記載の製造方法。
- ハロゲン化剤が塩化チオニルである請求項1~3のいずれか1項に記載の製造方法。
- スルファミン酸1モルに対し、塩化チオニル2~3モルを用いる請求項4に記載の製造方法。
- ハロゲン化剤を添加した後、混合物の温度を50℃~85℃にて反応させることをさらに含む請求項1~5のいずれか1項に記載の製造方法。
- ハロゲン化剤を添加した後、混合物の温度を86℃~105℃にて反応させることをさらに含む請求項1~5のいずれか1項に記載の製造方法。
- ハロゲン化剤を添加した後、混合物の温度を106℃~140℃にて反応させることをさらに含む請求項1~5のいずれか1項に記載の製造方法。
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES13828591T ES2707633T3 (es) | 2012-08-06 | 2013-07-24 | Método para producir bis(halosulfonil)amina |
KR1020157001555A KR101738789B1 (ko) | 2012-08-06 | 2013-07-24 | 비스(할로술포닐)아민의 제조 방법 |
CA2880723A CA2880723C (en) | 2012-08-06 | 2013-07-24 | Method for producing bis(halosulfonyl)amine |
JP2014529417A JPWO2014024682A1 (ja) | 2012-08-06 | 2013-07-24 | ビス(ハロスルホニル)アミンの製造方法 |
US14/416,495 US9650250B2 (en) | 2012-08-06 | 2013-07-24 | Method for producing bis(halosulfonyl)amine |
CN201380040804.8A CN104507855B (zh) | 2012-08-06 | 2013-07-24 | 双(卤代磺酰基)胺的制造方法 |
EP13828591.1A EP2881365B1 (en) | 2012-08-06 | 2013-07-24 | Method for producing bis(halosulfonyl)amine |
SG11201500611RA SG11201500611RA (en) | 2012-08-06 | 2013-07-24 | Method for producing bis(halosulfonyl)amine |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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JP2012-174209 | 2012-08-06 | ||
JP2012174209 | 2012-08-06 |
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WO2014024682A1 true WO2014024682A1 (ja) | 2014-02-13 |
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PCT/JP2013/070029 WO2014024682A1 (ja) | 2012-08-06 | 2013-07-24 | ビス(ハロスルホニル)アミンの製造方法 |
Country Status (9)
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US (1) | US9650250B2 (ja) |
EP (1) | EP2881365B1 (ja) |
JP (2) | JPWO2014024682A1 (ja) |
KR (1) | KR101738789B1 (ja) |
CN (1) | CN104507855B (ja) |
CA (1) | CA2880723C (ja) |
ES (1) | ES2707633T3 (ja) |
SG (1) | SG11201500611RA (ja) |
WO (1) | WO2014024682A1 (ja) |
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KR20160146796A (ko) * | 2014-04-18 | 2016-12-21 | 아르끄마 프랑스 | 플루오로설포닐 기를 함유하는 이미드의 제조 방법 |
JP2021525207A (ja) * | 2018-05-23 | 2021-09-24 | アルケマ フランス | フルオロスルホニル基を含有するイミド塩を調製するための方法 |
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WO2018132087A1 (en) * | 2017-01-10 | 2018-07-19 | Kuwait Institute For Scientific Research | Combination multi-effect distillation and multi-stage flash evaporation system |
FR3081457B1 (fr) * | 2018-05-23 | 2020-05-08 | Arkema France | Procede de preparation du sel de lithium du bis(fluorosulfonyl)imide |
FR3088931B1 (fr) * | 2018-11-28 | 2021-01-22 | Arkema France | Procédé de préparation du sel de lithium de bis(fluorosulfonyl)imide |
KR102516462B1 (ko) | 2020-12-23 | 2023-04-03 | 주식회사 천보신소재 | 비스(클로로술포닐)이미드의 제조 방법 |
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KR102537359B1 (ko) * | 2014-04-18 | 2023-05-25 | 아르끄마 프랑스 | 플루오로설포닐 기를 함유하는 이미드의 제조 방법 |
JP2021525207A (ja) * | 2018-05-23 | 2021-09-24 | アルケマ フランス | フルオロスルホニル基を含有するイミド塩を調製するための方法 |
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US9650250B2 (en) | 2017-05-16 |
CA2880723A1 (en) | 2014-02-13 |
KR20150031307A (ko) | 2015-03-23 |
CN104507855B (zh) | 2017-10-20 |
EP2881365B1 (en) | 2018-11-28 |
KR101738789B1 (ko) | 2017-05-22 |
JP2017226597A (ja) | 2017-12-28 |
SG11201500611RA (en) | 2015-03-30 |
CN104507855A (zh) | 2015-04-08 |
EP2881365A1 (en) | 2015-06-10 |
ES2707633T3 (es) | 2019-04-04 |
CA2880723C (en) | 2017-09-05 |
JP6497419B2 (ja) | 2019-04-10 |
JPWO2014024682A1 (ja) | 2016-07-25 |
EP2881365A4 (en) | 2016-04-20 |
US20150175422A1 (en) | 2015-06-25 |
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