WO2009136608A1 - Liquide ionique - Google Patents

Liquide ionique Download PDF

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Publication number
WO2009136608A1
WO2009136608A1 PCT/JP2009/058579 JP2009058579W WO2009136608A1 WO 2009136608 A1 WO2009136608 A1 WO 2009136608A1 JP 2009058579 W JP2009058579 W JP 2009058579W WO 2009136608 A1 WO2009136608 A1 WO 2009136608A1
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WIPO (PCT)
Prior art keywords
fta
ionic liquid
fsa
found
anal calcd
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PCT/JP2009/058579
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English (en)
Japanese (ja)
Inventor
松本　一
寺澤　直弘
栄部　比夏里
誠二 都築
Original Assignee
独立行政法人産業技術総合研究所
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Priority to US12/991,817 priority Critical patent/US20110070486A1/en
Priority to JP2010511070A priority patent/JP5339542B2/ja
Publication of WO2009136608A1 publication Critical patent/WO2009136608A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/48—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
    • H01G11/54—Electrolytes
    • H01G11/58—Liquid electrolytes
    • H01G11/62—Liquid electrolytes characterised by the solute, e.g. salts, anions or cations therein
    • 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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M8/00—Fuel cells; Manufacture thereof
    • H01M8/18—Regenerative fuel cells, e.g. redox flow batteries or secondary fuel cells
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M2300/00—Electrolytes
    • H01M2300/0017—Non-aqueous electrolytes
    • H01M2300/002—Inorganic electrolyte
    • H01M2300/0022—Room temperature molten salts
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M2300/00—Electrolytes
    • H01M2300/0017—Non-aqueous electrolytes
    • H01M2300/0025—Organic electrolyte
    • H01M2300/0045—Room temperature molten salts comprising at least one organic ion
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M2300/00—Electrolytes
    • H01M2300/0088—Composites
    • H01M2300/0091—Composites in the form of mixtures
    • 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
    • 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
    • Y02E60/30—Hydrogen technology
    • Y02E60/50—Fuel cells

Definitions

  • the present invention relates to an ionic liquid, and particularly relates to an ionic liquid having a low viscosity, a low melting point, and a high conductivity.
  • Ionic liquids have been special in recent years due to their potential applications as electrolytes, reaction media, and catalysts for organic synthesis for various electrochemical devices such as lithium secondary batteries, dye-sensitized solar cells, actuators and electric double layer capacitors. Has attracted a lot of attention. Compared to conventional organic liquid electrolytes, the main advantages of ionic liquids as electrolytes are non-flammability, non-volatility and high thermal stability.
  • the anion of the ionic liquid is bistrifluoromethylsulfonylamide (* conventionally the same as what is called bistrifluoromethylsulfonylimide, TFSI, but in recent years, Since it is recommended by IUPAC to call it amide, it is referred to as amide in this patent.) ([(CF 3 SO 2 ) 2 N] ⁇ ; [TFSA] ⁇ ) and tetrafluoroborate (BF 4 ⁇ ) has attracted attention because of its high electrochemical stability and thermal stability (Patent Documents 1 and 2).
  • Patent Document 4 discloses a salt containing fluorosulfonyl (trifluoromethylsulfonylamide) (FTA), but there is no disclosure of the melting point of the salt obtained in the examples, and this salt is an ionic liquid. Has not been demonstrated.
  • An object of the present invention is to provide an ionic liquid having a low viscosity, a low melting point, high conductivity, and high thermal stability.
  • an ionic liquid composed of a fluorosulfonyl (trifluoromethylsulfonylamide) (FTA) anion and a specific cation having a low viscosity, a low melting point, and a high conductivity at a low temperature. And it discovered that it had comparatively high thermal stability.
  • FFA fluorosulfonyl (trifluoromethylsulfonylamide)
  • An ionic liquid comprising a fluorosulfonyl (trifluoromethylsulfonylamide) (FTA) anion and one of the following cations: Tetramethylammonium (N1111); Ethyltrimethylammonium (N1112); n-propyltrimethylammonium (N1113); Diethyldimethylammonium (N1122); Di-n-propyldimethylammonium (N1133); Triethylmethylammonium (N2221); n-butyldiethylmethylammonium (N1224); N, N-diethyl-N-methyl-N- (2-methoxyethyl) ammonium (DEME); Tetraethylammonium (N2222); Tetra n-propylammonium (N3333); Tetra n-butylammonium (N4444); Tetra n-pent
  • Item 2. The ionic liquid according to Item 1, wherein the cation is tetraethylammonium (N2222) or triethylmethylammonium (N2221).
  • Item 3. Item 2. The ionic liquid according to Item 1, wherein the cation is tetramethylammonium (N1111), ethyltrimethylammonium (N1112), or n-propyltrimethylammonium (N1113).
  • Item 4. Item 2. The ionic liquid according to Item 1, wherein the cation is N, N-diethyl-N-methyl-N- (2-methoxyethyl) ammonium (DEME).
  • Item 4. The ionic liquid according to Item 1, wherein the cation is N-methyl-N-propyl-piperidinium (PP13).
  • Item 7. Item 4. The ionic liquid according to Item 1, wherein the cation is 5-azoniaspiro [4.4] nonane (AS44).
  • the ionic liquid of the present invention is suitable as an electrochemical device such as a lithium secondary battery, a fuel cell, a dye-sensitized solar cell, and an electric double layer capacitor, a solvent for chemical reaction, and a lubricating oil.
  • the melting point of the ionic liquid provided by the present invention is 120 ° C. or less, preferably 80 ° C. or less, more preferably 50 ° C. or less, further preferably 25 ° C. or less, particularly preferably 0 ° C. or less, and most preferably ⁇ 20 ° C. or less. It is.
  • an ionic liquid of 80 ° C. or lower can be widely used.
  • an energy device such as a solar cell, a lithium battery, or a capacitor
  • an electrochemical device such as an electrochromic device or an electrochemical sensor
  • the melting point of the ionic liquid is preferably room temperature (25 ° C.) or less, more preferably 0 ° C. or less. preferable.
  • the glass transition temperature is ⁇ 70 ° C. or lower, preferably ⁇ 80 ° C. or lower, more preferably ⁇ 90 ° C. or lower, still more preferably. If the temperature is ⁇ 100 ° C. or lower, the ionic liquid can be treated in the same manner as an ionic liquid having the melting point at the same temperature.
  • the present invention uses fluorosulfonyl (trifluoromethylsulfonylamide) (FTA; [(FSO 2 ) (CF 3 SO 2 ) N] ⁇ ) as an anionic component of an ionic liquid.
  • FTA fluorosulfonyl (trifluoromethylsulfonylamide)
  • anionic component of an ionic liquid is a known compound and can be produced, for example, according to Patent Document 3.
  • FTA [(FSO 2 ) (CF 3 SO 2 ) N] -
  • alkali metal ions Na + , K + , Li + , Cs + etc.
  • alkaline earth metal ions Ca 2+ , Mg 2+ , Ba 2+ etc.
  • H + , Bu 3 Sn + and other salt components are mixed with the salt containing the specific cation of the present invention to separate the ionic liquid of the present invention Can be manufactured.
  • a salt of FTA ([(FSO 2 ) (CF 3 SO 2 ) N] ⁇ ) H + obtained by passing through an ion exchange resin and a salt of (any cation of the present invention) + (OH) ⁇
  • an ionic liquid composed of FTA and the cation of the present invention can be preferably obtained.
  • the salt exchange reaction for obtaining the ionic liquid can be performed by a solvent extraction method when a desired molten salt can be extracted.
  • the cation component of the ionic liquid of the present invention is selected from the following cations: Tetramethylammonium (N1111); Ethyltrimethylammonium (N1112); n-propyltrimethylammonium (N1113); Diethyldimethylammonium (N1122); Di-n-propyldimethylammonium (N1133); Triethylmethylammonium (N2221); n-butyldiethylmethylammonium (N1224); N, N-diethyl-N-methyl-N- (2-methoxyethyl) ammonium (DEME); Tetraethylammonium (N2222); Tetra n-propylammonium (N3333); Tetra n-butylammonium (N4444); Tetra n-pentylammonium (N5555); 5-Azonia Spiro [4.4] Nonane (AS44) Dimethylimidazole (DMI) Prop
  • the molecular weight of FTA is intermediate between TFSA ([(CF 3 SO 2 ) 2 N] ⁇ ) and FSA ([(FSO 2 ) 2 N] ⁇ ), which are symmetrical anions. Therefore, viscosity, conductivity, diffusion coefficient, etc. are also expected to have intermediate properties between TFSA and FSA, but with regard to melting point, FTA anion has an asymmetric structure and is expected to decrease more dramatically.
  • the ionic liquid has a thermal stability generally higher than that of FSA.
  • the present inventors have confirmed that the FTA anion used in the present invention has high electrochemical stability comparable to that of conventional anions.
  • the formation of a liquid with a cation (N2222) indicates that the amide salt exhibits the highest oxidative stability to date.
  • 25 kinds of cationic components used in the present invention (N1111, N1112, N1113, N1122, N1133, N2221, N1224, DEME, N2222, N3333, N4444, N5555, AS44, DMI, PMI, BMI, Py11, Py12, Py14, PP11 , PP12, PP13, PP14, P2222, PS44) may be used alone, but by combining two or more cations, the melting point of the ionic liquid can be further lowered and the viscosity can be further lowered. It is.
  • FTA is used as the anion of the ionic liquid, but other anions can be blended as long as FTA is the main component.
  • Viscosity Viscosity was measured using a viscometer (Brookfield model DV-III +) with a 0.6 mL sample at 25 ° C.
  • DSC Differential Scanning Calorimeter
  • the FTA ionic liquid that is unnecessary in the water is extracted with dichloromethane, washed several times with water, and then the dichloromethane is distilled off. Obtained.
  • An ionic liquid composed of a salt of FTA and EMI (1-ethyl-3-methylimidazolium) was prepared in the same manner as described above.
  • N2222 [FSA] MS m / z (%) 130 (100) [N2222] + , 180 (100) [FSA] - ; Anal Calcd. For C 8 H 20 N 2 F 2 O 4 S 2 : C, 31.0; H, 6.5; N, 9.0; F, 12.2; Found: C, 30.8; H, 6.4; N, 9.0; F, 12.2.
  • N1111 [FSA] MS m / z (%) 74 (100) [N1111] + , 180 (100) [FSA] - ; Anal Calcd.
  • N4444 [FSA] MS m / z (%) 242 (100) [N4444] + , 180 (100) [FSA] - ; Anal Calcd. For C 16 H 36 N 2 F 2 O 4 S 2 : C, 45.5; H, 8.6; N, 6.6; F, 9.0; Found: C, 45.2; H, 8.7; N, 6.6; F, 9.1.
  • N3333 [FSA] MS m / z (%) 186 (100) [N3333] + , 180 (100) [FSA] - ; Anal Calcd.
  • N1133 [FSA] MS m / z (%) 130 (100) [N1133] + , 180 (100) [FSA] - ;
  • Anal Calcd.for C 8 H 20 N 2 F 2 O 4 S 2 C, 31.0; H, 6.5; N, 9.0; F, 12.2; Found: C, 30.7; H, 6.2; N, 9.0; F, 12.2 .
  • N1133 [TFSA] MS m / z (%) 130 (100) [N1133] + , 280 (100) [FSA] - ; Anal Calcd.
  • PS44 [FSA] MS m / z (%) 143 (100) [PS44] + , 180 (100) [FSA] - ;
  • Anal Calcd. For C 8 H 16 NPF 2 O 4 S 2 : C, 29.7; H, 5.0; N, 4.4; F, 11.8; Found: C, 29.7; H, 4.8; N, 4.3; F, 11.5.
  • PS44 [TFSA] MS m / z (%) 143 (100) [PS44] + , 280 (100) [TFSA] - ; Anal Calcd.
  • For C 10 H 16 NPF 6 O 4 S 2 C, 28.4; H, 3.8; N, 3.3; F, 26.5; Found: C, 28.5; H, 3.7; N, 3.4; F, 26.9.
  • Tables 1 to 6 show the melting points, electrical conductivity, glass transition point, thermal decomposition temperature, viscosity, and density of the compounds obtained in the above Examples and Comparative Examples.
  • FIG. 1 shows the measurement results of the potential windows of N2222 [FTA], N122.1O2 [FTA], EMI [FTA], and AS44 [FTA].
  • N122.1O2 [FTA] is DEME [FTA].
  • N2222 can be used as the cation species, and the oxidation limit potential is the most positive potential in the conventional amide anion system.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Power Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Sustainable Development (AREA)
  • Sustainable Energy (AREA)
  • Inorganic Chemistry (AREA)
  • Secondary Cells (AREA)
  • Electric Double-Layer Capacitors Or The Like (AREA)
  • Hybrid Cells (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L’invention concerne un liquide ionique qui présente une faible viscosité, un faible point de fusion, une conductivité électrique élevée et une stabilité thermique élevée. Le liquide ionique est composé d’anions et de cations de fluorosulfonyl(trifluorométhylsulfonylamide) (FTA) de N1111, N1112, N1113, N1122, N1133, N2221, N1224, DEME, N2222, N3333, N4444, N5555, AS44, DMI, PMI, BMI, Py11, Py12, Py14, PP11, PP12, PP13, PP14, P2222 ou PS44.
PCT/JP2009/058579 2008-05-09 2009-05-01 Liquide ionique WO2009136608A1 (fr)

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Application Number Priority Date Filing Date Title
US12/991,817 US20110070486A1 (en) 2008-09-10 2009-05-01 Ionic liquid
JP2010511070A JP5339542B2 (ja) 2008-05-09 2009-05-01 イオン液体

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JP2008-123623 2008-05-09
JP2008123623 2008-05-09
JP2008231764 2008-09-10
JP2008-231764 2008-09-10

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010532071A (ja) * 2007-06-29 2010-09-30 コモンウェルス サイエンティフィック アンド インダストリアル リサーチ オーガニゼイション リチウムエネルギー蓄積デバイス
JP2011100777A (ja) * 2009-11-04 2011-05-19 Sanyo Chem Ind Ltd 電解液およびそれを用いた電気化学素子
WO2012014938A1 (fr) * 2010-07-30 2012-02-02 出光興産株式会社 Huile de base de lubrifiant et composition de lubrifiant
WO2012042005A1 (fr) * 2010-09-30 2012-04-05 Basf Se Additif pour électrolytes
JP2012126846A (ja) * 2010-12-16 2012-07-05 Mitsubishi Materials Corp 粘着剤組成物
JP2012204133A (ja) * 2011-03-25 2012-10-22 National Institute Of Advanced Industrial & Technology 炭素質負極を有する非水電解質リチウムイオン電池
JP2013177324A (ja) * 2012-02-28 2013-09-09 National Institute Of Advanced Industrial Science & Technology イオン液体
JP2013196922A (ja) * 2012-03-21 2013-09-30 National Institute Of Advanced Industrial & Technology リチウムイオン電池用電解質
JP2014165110A (ja) * 2013-02-27 2014-09-08 National Institute Of Advanced Industrial & Technology リチウム溶融塩を電解液に用いたリチウム二次電池
WO2016031961A1 (fr) * 2014-08-29 2016-03-03 国立研究開発法人産業技術総合研究所 Liquide ionique et cristal de plastique
JP2016033117A (ja) * 2014-07-31 2016-03-10 国立大学法人鳥取大学 イオン液体、レドックスフロー二次電池用電解液、レドックスフロー二次電池および塩
JP2017091813A (ja) * 2015-11-10 2017-05-25 日産自動車株式会社 イオン伝導性を有する固体電解質およびこれを用いた電気化学デバイス
US10049825B2 (en) 2012-04-27 2018-08-14 Semiconductor Energy Laboratory Co., Ltd. Cyclic quaternary ammonium salt, nonaqueous solvent, nonaqueous electrolyte, and power storage device
JP2020500159A (ja) * 2016-10-19 2020-01-09 ハイドロ−ケベック スルファミン酸誘導体およびその調製のためのプロセス

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KR101752638B1 (ko) * 2015-08-12 2017-07-03 상명대학교산학협력단 난연성을 갖는 리튬이차전지의 전해액 및 그 제조방법

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005200359A (ja) * 2004-01-16 2005-07-28 Tosoh Corp イオン性化合物

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005200359A (ja) * 2004-01-16 2005-07-28 Tosoh Corp イオン性化合物

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010532071A (ja) * 2007-06-29 2010-09-30 コモンウェルス サイエンティフィック アンド インダストリアル リサーチ オーガニゼイション リチウムエネルギー蓄積デバイス
JP2011100777A (ja) * 2009-11-04 2011-05-19 Sanyo Chem Ind Ltd 電解液およびそれを用いた電気化学素子
WO2012014938A1 (fr) * 2010-07-30 2012-02-02 出光興産株式会社 Huile de base de lubrifiant et composition de lubrifiant
JP2012031275A (ja) * 2010-07-30 2012-02-16 Idemitsu Kosan Co Ltd 潤滑油基油および潤滑油組成物
CN103201891A (zh) * 2010-09-30 2013-07-10 巴斯夫欧洲公司 电解质添加剂
WO2012042005A1 (fr) * 2010-09-30 2012-04-05 Basf Se Additif pour électrolytes
JP2013542562A (ja) * 2010-09-30 2013-11-21 ビーエーエスエフ ソシエタス・ヨーロピア 電解質用添加剤
JP2012126846A (ja) * 2010-12-16 2012-07-05 Mitsubishi Materials Corp 粘着剤組成物
JP2012204133A (ja) * 2011-03-25 2012-10-22 National Institute Of Advanced Industrial & Technology 炭素質負極を有する非水電解質リチウムイオン電池
JP2013177324A (ja) * 2012-02-28 2013-09-09 National Institute Of Advanced Industrial Science & Technology イオン液体
JP2013196922A (ja) * 2012-03-21 2013-09-30 National Institute Of Advanced Industrial & Technology リチウムイオン電池用電解質
US10049825B2 (en) 2012-04-27 2018-08-14 Semiconductor Energy Laboratory Co., Ltd. Cyclic quaternary ammonium salt, nonaqueous solvent, nonaqueous electrolyte, and power storage device
JP2014165110A (ja) * 2013-02-27 2014-09-08 National Institute Of Advanced Industrial & Technology リチウム溶融塩を電解液に用いたリチウム二次電池
JP2016033117A (ja) * 2014-07-31 2016-03-10 国立大学法人鳥取大学 イオン液体、レドックスフロー二次電池用電解液、レドックスフロー二次電池および塩
WO2016031961A1 (fr) * 2014-08-29 2016-03-03 国立研究開発法人産業技術総合研究所 Liquide ionique et cristal de plastique
JPWO2016031961A1 (ja) * 2014-08-29 2017-06-08 国立研究開発法人産業技術総合研究所 イオン液体および柔粘性結晶
JP2017091813A (ja) * 2015-11-10 2017-05-25 日産自動車株式会社 イオン伝導性を有する固体電解質およびこれを用いた電気化学デバイス
JP2020500159A (ja) * 2016-10-19 2020-01-09 ハイドロ−ケベック スルファミン酸誘導体およびその調製のためのプロセス
US11345657B2 (en) 2016-10-19 2022-05-31 Hydro-Quebec Sulfamic acid derivatives and processes for their preparation
JP7171555B2 (ja) 2016-10-19 2022-11-15 ハイドロ－ケベック スルファミン酸誘導体およびその調製のためのプロセス

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