CA2441981A1 - Ionic liquids, electrolyte salts for electrical storage devices, liquid electrolytes for electrical storage devices, electrical double-layer capacitors, and secondary batteries - Google Patents

Ionic liquids, electrolyte salts for electrical storage devices, liquid electrolytes for electrical storage devices, electrical double-layer capacitors, and secondary batteries Download PDF

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Publication number
CA2441981A1
CA2441981A1 CA002441981A CA2441981A CA2441981A1 CA 2441981 A1 CA2441981 A1 CA 2441981A1 CA 002441981 A CA002441981 A CA 002441981A CA 2441981 A CA2441981 A CA 2441981A CA 2441981 A1 CA2441981 A1 CA 2441981A1
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storage devices
electrical storage
electrolyte
salt
electrical
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CA002441981A
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French (fr)
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CA2441981C (en
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Takaya Sato
Gen Masuda
Ryutaro Nozu
Tatsuya Maruo
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Nisshinbo Holdings Inc
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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
    • 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
    • H01M6/166—Cells with non-aqueous electrolyte with organic electrolyte characterised by the electrolyte by the solute
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • 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 Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • C07F9/5407—Acyclic saturated phosphonium compounds
    • 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
    • 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
    • H01G11/64—Liquid electrolytes characterised by additives
    • 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
    • H01M10/052—Li-accumulators
    • 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
    • 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
    • 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
    • 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
    • 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
    • Y02E60/13—Energy storage using capacitors
    • 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
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50—Manufacturing or production processes characterised by the final manufactured product

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Electrochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Power Engineering (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Physics & Mathematics (AREA)
  • Inorganic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Electric Double-Layer Capacitors Or The Like (AREA)
  • Secondary Cells (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)

Abstract

Electrical storage devices having excellent low-temperature properties can be obtained by using a quaternary salt (or ionic liquid) of general formula (1) below as an electrolyte salt for electrical storage devices or a liquid electrolyte for electrical storage devices.

(see formula 1) In formula (1), R1 to R4 are each independently an alkyl group of 1 to 5 carbons or an alkoxyalkyl group of the formula R'-O-(CH2)n-, with the proviso that at least one group from among R1 to R4 is the above alkoxyalkyl group. X is a nitrogen or phosphorus atom, and Y is a monovalent anion.

Claims (30)

1. An ionic liquid characterized by having general formula (1) below and a melting point of up to 50°C
wherein R1 to R4 are each independently an alkyl of 1 to 5 carbons or an alkoxyalkyl of the formula R'-O-(CH2)n-, R' being methyl or ethyl and the letter n being an integer from 1 to 4, and any two from among R1, R2, R3 and R4 may together form a ring, with the proviso that at least one of groups R1 to R4 is an alkoxyalkyl of the above formula; X is a nitrogen or phosphorus atom; and Y is a monovalent anion.
2. The ionic liquid of claim 1 which is characterized by having a melting point of up to 25°C.
3. The ionic liquid of claim 1 or 2 which is characterized in that X is a nitrogen atom.
4. The ionic liquid of claim 3 which is characterized in that X is a nitrogen atom, R' is methyl, and the letter n is 2.
5. The ionic liquid of claim 1 or 2 which is characterized by having general formula (2) below wherein R' is methyl or ethyl, X is a nitrogen or phosphorus atom, Y is a monovalent anion, Me signifies methyl and Et signifies ethyl.
6. ~The ionic liquid of any one of claims 1 to 5 which is characterized in that Y is BF4-, PF6-, (CF3SO2)2N-, CF3SO3- or CF3CO2-.
7. ~The ionic liquid of claim 5 which is characterized by having general formula (3) below wherein Me signifies methyl and Et signifies ethyl.
8. ~An electrolyte salt for electrical storage devices, which salt is characterized by being a quaternary salt of general formula (1) below wherein R1 to R4 are each independently an alkyl of 1 to 5 carbons or an alkoxyalkyl of the formula R'-O-(CH2)n-, R' being methyl or ethyl and the letter n being an integer from 1 to 4, and any two from among R1, R2, R3 and R4 may together form a ring, with the proviso that at least one of groups R1 to R4 is an alkoxyalkyl of the above formula; X is a nitrogen or phosphorus atom; and Y is a monovalent anion.
9. The electrolyte salt for electrical storage devices of claim 8 which is characterized by being a quaternary salt in which X is a nitrogen atom.
10. The electrolyte salt for electrical storage devices of claim 9 which is characterized by being a quaternary salt in which X is a nitrogen atom, R' is methyl and the letter n is 2.
11. The electrolyte salt for electrical storage devices of claim 8 which is characterized by being a quaternary salt having general formula (2) below wherein R' is methyl or ethyl, X is a nitrogen or phosphorus atom, Y is a monovalent anion, Me signifies methyl and Et signifies ethyl.
12. The electrolyte salt for electrical storage devices of any one of claims 8 to 11 which is characterized in that Y is BF4- , PF6- , (CF3SO2)2N- , CF3SO3- or CF3CO2-.
13. The electrolyte salt for electrical storage devices of claim 11 which is characterized by having general formula (3) below wherein Me signifies methyl and Et signifies ethyl.
14. The electrolyte salt for electrical storage devices of any one of claims 8 to 13 which is characterized by having a melting point of up to 25° C.
15. A liquid electrolyte for electrical storage devices which is characterized by being composed solely of the ionic liquid of any one of claims 1 to 7.
16. A liquid electrolyte for electrical storage devices which is characterized by being composed solely of the electrolyte salt for electrical storage devices of claim 14.
17. A liquid electrolyte for electrical storage devices which is characterized by including at least one ionic liquid of any one of claims 1 to 7 and a nonaqueous organic solvent.
18. A liquid electrolyte for electrical storage devices which is characterized by including at least one electrolyte salt for electrical storage devices according to any one of claims 8 to 13 and a nonaqueous organic solvent.
19. The liquid electrolyte for electrical storage devices of claim 17 or 18 which is characterized in that the nonaqueous organic solvent is a mixed solvent which includes as a main component ethylene carbonate or propylene carbonate.
20. The liquid electrolyte for electrical storage devices of claim 17 or 18 which is characterized in that the nonaqueous organic solvent is one selected from among ethylene carbonate, propylene carbonate, vinylene carbonate, dimethyl carbonate, ethyl methyl carbonate and diethyl carbonate, or a mixed solvent of two or more thereof.
21. An electrical double-layer capacitor having a pair of polarizable electrodes, a separator between the polarizable electrodes and a liquid electrolyte, which electrical double-layer capacitor is characterized in that the liquid electrolyte is a liquid electrolyte for electrical storage devices according to any one of claims 15 to 20.
22. The electrical double-layer capacitor of claim 21 which is characterized in that the polarizable electrodes include as a main component a carbonaceous material prepared from a resin.
23. The electrical double-layer capacitor of claim 22 which is characterized in that the resin is a phenolic resin or a polycarbodiimide resin.
24. The electrical double-layer capacitor of claim 22 which is characterized in that the carbonaceous material is prepared by carbonizing a phenolic resin or polycarbodiimide resin, then activating the carbonized resin.
25. An electrolyte solution for electrical storage devices which is characterized by being composed of the liquid electrolyte for electrical storage devices of claim 15 or 16 and an ion-conductive salt which is solid at ambient temperature.
26. The electrolyte solution for electrical storage devices of claim 25 which is characterized in that the ion-conductive salt is a lithium salt.
27. The electrolyte solution for electrical storage devices of claim 25 or 26 which is characterized by including also a nonaqueous organic solvent.
28. A secondary battery having a positive electrode and a negative electrode, a separator between the positive and negative electrodes, and an electrolyte solution, which secondary battery is characterized in that the electrolyte solution is an electrolyte solution for electrical storage devices according to claim 25, 26 or 27.
29. An electrical double-layer capacitor having a pair of polarizable electrodes, a separator between the polarizable electrodes and a liquid electrolyte, which electrical double-layer capacitor is characterized in that the liquid electrolyte is an electrolyte solution for electrical storage devices according to claim 25, 26 or 27.
30. An electrical storage device having a positive electrode and a negative electrode, a separator between the positive and negative electrodes, and a liquid electrolyte, which electrical storage device is characterized in that the positive electrode is activated carbon, the negative electrode is a carbonaceous material that is capable of occluding and releasing lithium ions, and the liquid electrolyte is an electrolyte solution for electrical storage devices according to claim 25, 26 or 27.
CA2441981A 2001-03-26 2002-03-25 Ionic liquids, electrolyte salts for electrical storage devices, liquid electrolytes for electrical storage devices, electrical double-layer capacitors, and secondary batteries Expired - Lifetime CA2441981C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
JP2001087221 2001-03-26
JP2001-87221 2001-03-26
JP2001272834 2001-09-10
JP2001-272834 2001-09-10
PCT/JP2002/002845 WO2002076924A1 (en) 2001-03-26 2002-03-25 Ionic liquid, electrolyte salt for storage device, electrolytic solution for storage device, electric double layer capacitor, and secondary battery

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CA2441981A1 true CA2441981A1 (en) 2002-10-03
CA2441981C CA2441981C (en) 2012-05-15

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US (2) US7297289B2 (en)
EP (4) EP2295399A3 (en)
JP (3) JPWO2002076924A1 (en)
KR (3) KR100823972B1 (en)
CN (2) CN100406431C (en)
CA (1) CA2441981C (en)
TW (1) TW591677B (en)
WO (1) WO2002076924A1 (en)

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