WO2010047257A1 - スルホン化合物 - Google Patents
スルホン化合物 Download PDFInfo
- Publication number
- WO2010047257A1 WO2010047257A1 PCT/JP2009/067791 JP2009067791W WO2010047257A1 WO 2010047257 A1 WO2010047257 A1 WO 2010047257A1 JP 2009067791 W JP2009067791 W JP 2009067791W WO 2010047257 A1 WO2010047257 A1 WO 2010047257A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- sulfone
- butyl
- formula
- solvent
- compound
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/02—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms
- C07C317/04—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
-
- 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
- H01M10/0569—Liquid materials characterised by the solvents
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M6/00—Primary cells; Manufacture thereof
- H01M6/14—Cells with non-aqueous electrolyte
- H01M6/16—Cells with non-aqueous electrolyte with organic electrolyte
- H01M6/162—Cells with non-aqueous electrolyte with organic electrolyte characterised by the electrolyte
- H01M6/164—Cells with non-aqueous electrolyte with organic electrolyte characterised by the electrolyte by the solvent
-
- 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 sulfone compound. More specifically, the present invention relates to a sulfone compound that is mainly useful as a solvent for electrochemical devices.
- Sulfone compounds are used as extraction solvents and various reaction solvents, while those having a high dielectric constant are also used as aprotic polar solvents and as solvents for electrochemical devices.
- an electric double layer capacitor using a sulfolane derivative such as sulfolane or 3-methylsulfolane as an electrolyte Patent Document 1
- Patent Document 2 using a solvent as an electrolytic solution has been proposed.
- An aprotic polar solvent used as a solvent for electrochemical devices or the like is generally desired to have a low melting point, excellent thermal stability, and low viscosity.
- a solvent having low water solubility is preferably used.
- Patent Document 1 and Patent Document 2 have a relatively high melting point, there are problems such as a decrease in function in a low-temperature environment. Moreover, the propylene carbonate used together with these has problems such as poor thermal stability and relatively high solubility in water.
- JP-A-62-237715 Japanese Unexamined Patent Publication No. Sho 63-12122
- An object of the present invention is to provide an aprotic polar solvent having a relatively low melting point and excellent thermal stability.
- the present invention relates to a sulfone compound represented by the following formula (1).
- R 1 and R 2 represent an alkyl group having 3 to 6 carbon atoms. However, R 1 and R 2 are different groups.
- alkyl group having 3 to 6 carbon atoms represented by R 1 a chain alkyl group having 3 to 4 carbon atoms is preferable, and a propyl group, isopropyl group, butyl group or s-butyl group is more preferable.
- alkyl group having 3 to 6 carbon atoms represented by R 2 a branched alkyl group having 4 carbon atoms is preferable, and isobutyl group or s-butyl group is more preferable.
- sulfone compound of the present invention represented by the formula (1) include, for example, propylisopropylsulfone, propylisobutylsulfone, propyl s-butylsulfone, propyl t-butylsulfone, isopropylbutylsulfone, isopropylisobutylsulfone, isopropyl s-butyl sulfone, isopropyl t-butyl sulfone, butyl isobutyl sulfone, butyl s-butyl sulfone, butyl t-butyl sulfone, isobutyl s-butyl sulfone, isobutyl t-butyl sulfone, s-butyl t-butyl sulfone, propyl isopentyl Examples include sulfone, isopropylis
- propyl isobutyl sulfone, propyl s-butyl sulfone, isopropyl butyl sulfone, isopropyl isobutyl sulfone, isopropyl s-butyl sulfone, butyl isobutyl sulfone, butyl s-butyl sulfone, and s-butyl isobutyl sulfone are preferably used.
- the sulfone compound represented by the formula (1) is, for example, a sulfide represented by the formula (4) obtained by reacting a thiol represented by the formula (2) with an organic halogen compound represented by the formula (3).
- the compound can be prepared by oxidizing the sulfide compound using an oxidizing agent.
- R 1 represents an alkyl group having 3 to 6 carbon atoms.
- R 2 represents an alkyl group having 3 to 6 carbon atoms, and is a group different from R 1 in the formula (2).
- X represents a halogen atom.
- R 1 represents the same group as R 1 in the formula (2)
- R 2 represents the same group as R 2 in the formula (3).
- thiol examples include propyl thiol, isopropyl thiol, butyl thiol, and s-butyl thiol.
- organic halogen compound examples include 2-bromobutane and 1-bromoisobutane.
- the ratio of thiol used is 0.5 to 10 mol with respect to 1 mol of the organic halogen compound. It is preferably 0.5 to 5 mol.
- the solvent may not be used, but may be used as necessary, for example, when the raw material is a solid or the viscosity of the reaction solution is high and stirring is insufficient.
- the solvent to be used is not particularly limited, but for example, methanol, ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, tetradecanol, cyclohexanol, Alcohols such as ethylene glycol and propylene glycol, diethyl ether, dipropyl ether, dibutyl ether, dipentyl ether, dihexyl ether, diheptyl ether, dioctyl ether, THF, tetrahydropyran, ethers such as 1,4-dioxane, acetonitrile, Nitriles such as acrylonitrile and propionitrile, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone
- the amount of the solvent used is not particularly limited, but is preferably 100 to 5000 parts by weight with respect to 100 parts by weight of the organic halogen compound.
- the reaction temperature is preferably 0 to 200 ° C, more preferably 10 to 150 ° C.
- the reaction time is usually 1 to 30 hours.
- oxidizing agent used for the oxidation of the sulfide compound represented by the formula (3) are not particularly limited.
- potassium permanganate, chromium Examples include acids, oxygen, aqueous hydrogen peroxide, and organic oxides such as 3-chloroperbenzoic acid.
- hydrogen peroxide water is preferably used.
- the ratio of the oxidizing agent used is preferably 1.8 to 10 moles, more preferably 2 to 5 moles per mole of the sulfide compound.
- the solvent may not be used, but may be used as necessary, for example, when the raw material is solid or the reaction solution has a high viscosity and stirring is insufficient.
- the solvent to be used is not particularly limited.
- halogenation such as carbon tetrachloride, chloroform, dichloromethane, bromopropane, bromobutane, bromopentane, bromohexane, methyl iodide, ethyl iodide, propyl iodide and the like.
- Alkenes such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, pentane, hexane, heptane, octane, nonane, decane, undecane, dodecane, cyclohexane, petroleum ether, benzine, kerosene, toluene, xylene, mesitylene, benzene, etc. And hydrocarbons, and water. Of these, alkyl halides and water are preferably used. These solvents may be used alone or in combination of two or more.
- the amount of the solvent used is not particularly limited, but is preferably 100 to 5000 parts by weight with respect to 100 parts by weight of the sulfide compound.
- the reaction temperature is preferably 0 to 200 ° C, more preferably 10 to 150 ° C.
- the reaction time is usually 1 to 30 hours.
- the sulfone compound thus obtained can be isolated by distillation after water washing and liquid separation as necessary.
- the sulfone compound of the present invention can be suitably used, for example, as a solvent for electrochemical devices such as an electrolyte solvent.
- electrochemical devices such as an electrolyte solvent.
- the electrochemical device include a lithium primary battery, a lithium secondary battery, a lithium ion battery, a fuel cell, a solar cell, and an electric double layer capacitor.
- the sulfone compound of the present invention is characterized by low water solubility. Thereby, when it uses for the said solvent for electrochemical devices, mixing of water can be suppressed and generation
- the sulfone compound of the present invention has a relatively low melting point and excellent thermal stability, it can be safely used in a wide temperature range from a low temperature to a high temperature.
- the sulfone compound of the present invention has a low viscosity, the ionic conductivity of the electrolyte can be greatly increased, and high electrical characteristics can be realized.
- the sulfone compound of the present invention is an aprotic polar solvent having a relatively low melting point, excellent thermal stability, low viscosity, and low water solubility. It is useful as a solvent for devices.
- Example 1 [Synthesis of butyl isobutyl sulfone (BIBS)] A 200 mL four-necked flask equipped with a stirrer, a thermometer and a condenser was charged with 60 g (0.15 mol) of a 10% aqueous sodium hydroxide solution in a nitrogen atmosphere and maintained at room temperature. After gradually adding 5 g (0.15 mol), the mixture was stirred for 1 hour. Next, 13.7 g (0.10 mol) of 1-bromo-2-methylpropane was charged into a 200 mL four-necked flask equipped with a stirrer, a thermometer and a condenser, and the above 1-butanethiol sodium hydroxide was charged.
- BIBS butyl isobutyl sulfone
- the melting point and exothermic start temperature of the obtained butyl isobutyl sulfone were measured using a differential scanning calorimeter in a nitrogen atmosphere.
- the viscosity was measured using a rotational viscometer (trade name “DISITAL VISCOMETER”, manufactured by Tokimec Co., Ltd.).
- the solubility of water was determined by measuring the water content of the sulfone compound in which water was saturated and dissolved, using a Karl Fischer coulometric titrator.
- butyl isobutyl sulfone could be identified from the following physical properties.
- Example 2 [Synthesis of Propylisobutylsulfone (PIBS)] A 200 mL four-necked flask equipped with a stirrer, a thermometer and a condenser was charged with 60 g (0.15 mol) of a 10% aqueous sodium hydroxide solution in a nitrogen atmosphere and maintained at room temperature. After gradually adding 4 g (0.15 mol), the mixture was stirred for 1 hour. Next, 13.7 g (0.10 mol) of 1-bromo-2-methylpropane was charged into a 200 mL four-necked flask equipped with a stirrer, a thermometer, and a condenser, and the above 1-propanethiol sodium hydroxide was charged.
- PIBS Propylisobutylsulfone
- the whole amount of the aqueous solution was added and stirred at 60 ° C. for 2 hours. This was cooled to room temperature, 50 ml of dichloromethane was added and stirred for 10 minutes, and then the dichloromethane layer was separated and washed once with 30 ml of ultrapure water. To the obtained dichloromethane layer, 19.2 g (0.20 mol) of 35% hydrogen peroxide was added and stirred at 30 ° C. for 2 hours, and the dichloromethane layer was distilled to obtain 14.5 g of propylisobutylsulfone as a colorless transparent liquid. Obtained. The yield of the obtained propylisobutylsulfone was 88% with respect to 1-bromo-2-methylpropane.
- propyl isobutyl sulfone was able to be identified from having the following physical properties.
- Example 3 Synthesis of Isopropylisobutylsulfone (IPIBS)] In a 200 mL four-necked flask equipped with a stirrer, a thermometer and a condenser, 60 g (0.15 mol) of a 10% aqueous sodium hydroxide solution was charged in a nitrogen atmosphere and maintained at room temperature. After gradually adding 4 g (0.15 mol), the mixture was stirred for 1 hour.
- IPIBS Isopropylisobutylsulfone
- Table 1 shows the measurement results of melting points, exothermic starting temperatures, viscosities and water solubility in Examples 1 to 3 together with propylene carbonate as Comparative Example 1 and sulfolane as Comparative Example 2.
- an aprotic polar solvent having a relatively low melting point and excellent thermal stability which is mainly useful for a solvent for electrochemical devices.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
上記電気化学デバイスとしては、例えば、リチウム一次電池、リチウム二次電池、リチウムイオン電池、燃料電池、太陽電池、電気二重層コンデンサ等が挙げられる。
また、本発明のスルホン化合物は、融点が比較的低く、熱的安定性に優れることから、低温から高温まで広い温度範囲で安全に使用することができる。
更に、本発明のスルホン化合物は、粘度が低いことから、電解質のイオン導電性を大幅に高めることができ、高い電気特性を実現することができる。
攪拌機、温度計および冷却器を備え付けた200mL容の四つ口フラスコに、窒素雰囲気下で、10%水酸化ナトリウム水溶液60g(0.15mol)を仕込み、室温に維持しながら1-ブタンチオール13.5g(0.15mol)を徐々に加えた後、1時間撹拌した。次に、攪拌機、温度計および冷却器を備え付けた200mL容の四つ口フラスコに1-ブロモ-2-メチルプロパン13.7g(0.10mol)を仕込み、上記の1-ブタンチオールの水酸化ナトリウム水溶液の全量を加え、60℃で2時間攪拌した。これを室温まで冷却し、ジクロロメタンを50ml加え10分撹拌した後、ジクロロメタン層を分取し、超純水30mLで1回洗浄した。得られたジクロロメタン層に35%過酸化水素水19.2g(0.20mol)を加え、30℃で2時間攪拌し、ジクロロメタン層を蒸留することにより、無色透明液体のブチルイソブチルスルホン16.0gを得た。得られたブチルイソブチルスルホンの収率は、1-ブロモ-2-メチルプロパンに対して90%であった。
元素分析:C 53.9;H 10.2;S 18.0(計算値 C 53.9;H 10.2;S 18.0)
攪拌機、温度計および冷却器を備え付けた200mL容の四つ口フラスコに、窒素雰囲気下で、10%水酸化ナトリウム水溶液60g(0.15mol)を仕込み、室温に維持しながら1-プロパンチオール11.4g(0.15mol)を徐々に加えた後、1時間撹拌した。次に、攪拌機、温度計および冷却器を備え付けた200mL容の四つ口フラスコに1-ブロモ-2-メチルプロパン13.7g(0.10mol)を仕込み、上記の1-プロパンチオールの水酸化ナトリウム水溶液の全量を加え、60℃で2時間攪拌した。これを室温まで冷却し、ジクロロメタンを50ml加え10分撹拌した後、ジクロロメタン層を分取し、超純水30mLで1回洗浄した。得られたジクロロメタン層に35%過酸化水素水19.2g(0.20mol)を加え、30℃で2時間攪拌し、ジクロロメタン層を蒸留することにより、無色透明液体のプロピルイソブチルスルホン14.5gを得た。得られたプロピルイソブチルスルホンの収率は、1-ブロモ-2-メチルプロパンに対して88%であった。
元素分析:C 51.2;H 9.8;S 19.5(計算値 C 51.2;H 9.8;S 19.5)
攪拌機、温度計および冷却器を備え付けた200mL容の四つ口フラスコに、窒素雰囲気下で、10%水酸化ナトリウム水溶液60g(0.15mol)を仕込み、室温に維持しながら2-プロパンチオール11.4g(0.15mol)を徐々に加えた後、1時間撹拌した。次に、攪拌機、温度計および冷却器を備え付けた200mL容の四つ口フラスコに1-ブロモ-2-メチルプロパン13.7g(0.10mol)を仕込み、上記の2-プロパンチオールの水酸化ナトリウム水溶液の全量を加え、60℃で2時間攪拌した。これを室温まで冷却し、ジクロロメタンを50ml加え10分撹拌した後、ジクロロメタン層を分取し、超純水30mLで1回洗浄した。得られたジクロロメタン層に35%過酸化水素水19.2g(0.20mol)を加え、30℃で2時間攪拌し、ジクロロメタン層をすることにより、無色透明液体のイソプロピルイソブチルスルホン11.2gを得た。得られたイソプロピルイソブチルスルホンの収率は、1-ブロモ-2-メチルプロパンに対して85%であった。
元素分析:C 51.2;H 9.8;S 19.5(計算値 C 51.2;H 9.8;S 19.5)
Claims (2)
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP09821954A EP2351735A1 (en) | 2008-10-24 | 2009-10-14 | Sulfone compound |
CN2009801418411A CN102197024A (zh) | 2008-10-24 | 2009-10-14 | 砜化合物 |
US13/123,665 US20110306797A1 (en) | 2008-10-24 | 2009-10-14 | Sulfone compound |
JP2010534776A JPWO2010047257A1 (ja) | 2008-10-24 | 2009-10-14 | スルホン化合物 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008274932 | 2008-10-24 | ||
JP2008-274932 | 2008-10-24 |
Publications (1)
Publication Number | Publication Date |
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WO2010047257A1 true WO2010047257A1 (ja) | 2010-04-29 |
Family
ID=42119298
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2009/067791 WO2010047257A1 (ja) | 2008-10-24 | 2009-10-14 | スルホン化合物 |
Country Status (7)
Country | Link |
---|---|
US (1) | US20110306797A1 (ja) |
EP (1) | EP2351735A1 (ja) |
JP (1) | JPWO2010047257A1 (ja) |
KR (1) | KR20110074571A (ja) |
CN (1) | CN102197024A (ja) |
TW (1) | TW201031627A (ja) |
WO (1) | WO2010047257A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012051857A (ja) * | 2010-09-03 | 2012-03-15 | Sumitomo Seika Chem Co Ltd | スルホン化合物 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5618833B2 (ja) * | 2008-11-17 | 2014-11-05 | 住友精化株式会社 | スルホン化合物 |
FR2993886B1 (fr) * | 2012-07-26 | 2014-08-01 | Renault Sa | Composes sulfonates specifiques utilisables comme solvant d'electrolyte pour batteries au lithium |
FR3003570B1 (fr) | 2013-03-20 | 2016-01-29 | Renault Sas | Composes sulfonates specifiques utilisables comme solvant d'electrolyte pour batteries au lithium |
CN110106515B (zh) * | 2019-06-03 | 2020-04-28 | 南京工业大学 | 一种利用电化学微通道技术制备砜类化合物的方法 |
WO2021105376A1 (de) * | 2019-11-28 | 2021-06-03 | Saltigo Gmbh | Verbessertes verfahren zur herstellung von unsymmetrischen dialkylsulfiden |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63239911A (ja) * | 1987-03-27 | 1988-10-05 | 旭硝子株式会社 | 固体電解コンデンサ |
JPH09147913A (ja) * | 1995-11-22 | 1997-06-06 | Sanyo Electric Co Ltd | 非水電解質電池 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU1084599A (en) * | 1997-10-15 | 1999-05-03 | Arizona Board Of Regents, The | Non-aqueous electrolyte solvents for secondary cells |
EP1842250B1 (en) * | 2005-01-19 | 2013-09-04 | Arizona Board of Regents, acting for and on behalf of Arizona State University | Electric current-producing device having a sulfone-based electrolyte |
-
2009
- 2009-10-14 WO PCT/JP2009/067791 patent/WO2010047257A1/ja active Application Filing
- 2009-10-14 KR KR1020117010032A patent/KR20110074571A/ko not_active Application Discontinuation
- 2009-10-14 JP JP2010534776A patent/JPWO2010047257A1/ja not_active Withdrawn
- 2009-10-14 EP EP09821954A patent/EP2351735A1/en not_active Withdrawn
- 2009-10-14 CN CN2009801418411A patent/CN102197024A/zh active Pending
- 2009-10-14 US US13/123,665 patent/US20110306797A1/en not_active Abandoned
- 2009-10-22 TW TW098135704A patent/TW201031627A/zh unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63239911A (ja) * | 1987-03-27 | 1988-10-05 | 旭硝子株式会社 | 固体電解コンデンサ |
JPH09147913A (ja) * | 1995-11-22 | 1997-06-06 | Sanyo Electric Co Ltd | 非水電解質電池 |
Non-Patent Citations (1)
Title |
---|
A. H. FAWCETT ET AL.: "Carbon-13 NMR Spectra of Monosulphones and Disulphones: Substitution Rules and Conformational Effects", ORGANIC MAGNETIC RESONANCE, vol. 10, no. 7, 1978, pages 360 - 369, XP008146344 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012051857A (ja) * | 2010-09-03 | 2012-03-15 | Sumitomo Seika Chem Co Ltd | スルホン化合物 |
Also Published As
Publication number | Publication date |
---|---|
EP2351735A1 (en) | 2011-08-03 |
KR20110074571A (ko) | 2011-06-30 |
US20110306797A1 (en) | 2011-12-15 |
CN102197024A (zh) | 2011-09-21 |
TW201031627A (en) | 2010-09-01 |
JPWO2010047257A1 (ja) | 2012-03-22 |
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