WO2015159386A1 - 電気化学デバイス電解液用溶媒 - Google Patents
電気化学デバイス電解液用溶媒 Download PDFInfo
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- WO2015159386A1 WO2015159386A1 PCT/JP2014/060826 JP2014060826W WO2015159386A1 WO 2015159386 A1 WO2015159386 A1 WO 2015159386A1 JP 2014060826 W JP2014060826 W JP 2014060826W WO 2015159386 A1 WO2015159386 A1 WO 2015159386A1
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- Prior art keywords
- solvent
- electrochemical device
- compound
- mass
- sulfone compound
- Prior art date
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- 239000002904 solvent Substances 0.000 title claims abstract description 55
- 239000008151 electrolyte solution Substances 0.000 title abstract description 20
- -1 cyclic sulfone compound Chemical class 0.000 claims abstract description 74
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 239000003792 electrolyte Substances 0.000 claims description 50
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 10
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 claims description 3
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 claims description 2
- 238000005868 electrolysis reaction Methods 0.000 claims 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 30
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 12
- 229940021013 electrolyte solution Drugs 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 8
- YBJCDTIWNDBNTM-UHFFFAOYSA-N 1-methylsulfonylethane Chemical compound CCS(C)(=O)=O YBJCDTIWNDBNTM-UHFFFAOYSA-N 0.000 description 7
- RDKKQZIFDSEMNU-UHFFFAOYSA-N 2-ethylsulfonylpropane Chemical compound CCS(=O)(=O)C(C)C RDKKQZIFDSEMNU-UHFFFAOYSA-N 0.000 description 6
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
- 239000003990 capacitor Substances 0.000 description 6
- 238000013112 stability test Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 3
- AIDFJGKWTOULTC-UHFFFAOYSA-N 1-butylsulfonylbutane Chemical compound CCCCS(=O)(=O)CCCC AIDFJGKWTOULTC-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000004255 ion exchange chromatography Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- LZKMCMVHIIAVLF-UHFFFAOYSA-N 1-butylsulfonylpentane Chemical compound CCCCCS(=O)(=O)CCCC LZKMCMVHIIAVLF-UHFFFAOYSA-N 0.000 description 1
- NJAKRNRJVHIIDT-UHFFFAOYSA-N 1-ethylsulfonyl-2-methylpropane Chemical compound CCS(=O)(=O)CC(C)C NJAKRNRJVHIIDT-UHFFFAOYSA-N 0.000 description 1
- JFRJNQRJQRIUPT-UHFFFAOYSA-N 1-ethylsulfonyl-3-methylbutane Chemical compound CCS(=O)(=O)CCC(C)C JFRJNQRJQRIUPT-UHFFFAOYSA-N 0.000 description 1
- PVSJGAIWOIMZFG-UHFFFAOYSA-N 1-ethylsulfonylbutane Chemical compound CCCCS(=O)(=O)CC PVSJGAIWOIMZFG-UHFFFAOYSA-N 0.000 description 1
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 description 1
- LCGJGVKAKOQMHO-UHFFFAOYSA-N 1-ethylsulfonylpentane Chemical compound CCCCCS(=O)(=O)CC LCGJGVKAKOQMHO-UHFFFAOYSA-N 0.000 description 1
- URDYJNJREUFXGD-UHFFFAOYSA-N 1-ethylsulfonylpropane Chemical compound CCCS(=O)(=O)CC URDYJNJREUFXGD-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- NLUGCAKOZAODBF-UHFFFAOYSA-N 1-pentylsulfonylpentane Chemical compound CCCCCS(=O)(=O)CCCCC NLUGCAKOZAODBF-UHFFFAOYSA-N 0.000 description 1
- JEXYCADTAFPULN-UHFFFAOYSA-N 1-propylsulfonylpropane Chemical compound CCCS(=O)(=O)CCC JEXYCADTAFPULN-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- SOISRTCWXMURDJ-UHFFFAOYSA-N 3-(2-methylpropyl)thiolane 1,1-dioxide Chemical compound CC(C)CC1CCS(=O)(=O)C1 SOISRTCWXMURDJ-UHFFFAOYSA-N 0.000 description 1
- JEIQEQBAZNCTKR-UHFFFAOYSA-N 3-butylthiolane 1,1-dioxide Chemical compound CCCCC1CCS(=O)(=O)C1 JEIQEQBAZNCTKR-UHFFFAOYSA-N 0.000 description 1
- SOZYDBBOFTUUPT-UHFFFAOYSA-N 3-ethylthiolane 1,1-dioxide Chemical compound CCC1CCS(=O)(=O)C1 SOZYDBBOFTUUPT-UHFFFAOYSA-N 0.000 description 1
- HUYRZIRTRSAKQZ-UHFFFAOYSA-N 3-methyl-1-(2-methylpropylsulfonyl)butane Chemical compound CC(C)CCS(=O)(=O)CC(C)C HUYRZIRTRSAKQZ-UHFFFAOYSA-N 0.000 description 1
- CMJLMPKFQPJDKP-UHFFFAOYSA-N 3-methylthiolane 1,1-dioxide Chemical compound CC1CCS(=O)(=O)C1 CMJLMPKFQPJDKP-UHFFFAOYSA-N 0.000 description 1
- JUKITVAVAFWANY-UHFFFAOYSA-N 3-pentylthiolane 1,1-dioxide Chemical compound CCCCCC1CCS(=O)(=O)C1 JUKITVAVAFWANY-UHFFFAOYSA-N 0.000 description 1
- KEIWCJFRHAPCIO-UHFFFAOYSA-N 3-propan-2-ylthiolane 1,1-dioxide Chemical compound CC(C)C1CCS(=O)(=O)C1 KEIWCJFRHAPCIO-UHFFFAOYSA-N 0.000 description 1
- XWVQGSWWPONKGD-UHFFFAOYSA-N 3-propylthiolane 1,1-dioxide Chemical compound CCCC1CCS(=O)(=O)C1 XWVQGSWWPONKGD-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 150000005678 chain carbonates Chemical class 0.000 description 1
- 150000005676 cyclic carbonates Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- ZQJAONQEOXOVNR-UHFFFAOYSA-N n,n-di(nonyl)nonan-1-amine Chemical compound CCCCCCCCCN(CCCCCCCCC)CCCCCCCCC ZQJAONQEOXOVNR-UHFFFAOYSA-N 0.000 description 1
- CLZGJKHEVKJLLS-UHFFFAOYSA-N n,n-diheptylheptan-1-amine Chemical compound CCCCCCCN(CCCCCCC)CCCCCCC CLZGJKHEVKJLLS-UHFFFAOYSA-N 0.000 description 1
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
- NJWMENBYMFZACG-UHFFFAOYSA-N n-heptylheptan-1-amine Chemical compound CCCCCCCNCCCCCCC NJWMENBYMFZACG-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- MFHKEJIIHDNPQE-UHFFFAOYSA-N n-nonylnonan-1-amine Chemical compound CCCCCCCCCNCCCCCCCCC MFHKEJIIHDNPQE-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- 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
- H01G11/60—Liquid electrolytes characterised by the solvent
-
- 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
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/004—Details
- H01G9/022—Electrolytes; Absorbents
- H01G9/035—Liquid electrolytes, e.g. impregnating 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
- H01M10/052—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
- H01M10/0567—Liquid materials characterised by the additives
-
- 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
- H01M2300/0028—Organic electrolyte characterised by the solvent
-
- 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
- H01M2300/0028—Organic electrolyte characterised by the solvent
- H01M2300/0037—Mixture of solvents
-
- 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
Definitions
- the present invention relates to a solvent for an electrochemical device electrolyte used for an electrochemical device such as a capacitor.
- Electrochemicals such as various secondary batteries and aluminum electrolytic capacitors that can obtain high energy density as devices used for power supplies for electronic equipment, power storage power supplies, power supplies for automobiles, etc. Devices are drawing attention.
- the solvent for the electrolyte used in these electrochemical devices for example, cyclic carbonates such as propylene carbonate, ethylene carbonate, and diethyl carbonate, chain carbonates, ⁇ -butyrolactone, and derivatives based on them Etc.
- Patent Documents 1 and 2 disclose electrolytic capacitors using ⁇ -butyrolactone.
- a sulfone compound such as sulfolane is electrically and chemically stable.
- Patent Document 3 discloses an electric double layer capacitor using propylene carbonate and sulfolane.
- the solvent for the electrolytic solution using the sulfone compound also has a property of thermally decomposing at a high temperature to generate sulfur dioxide.
- Patent Document 4 discloses a method of adding an organic sulfur compound
- Patent Document 5 discloses a weakly basic organic compound, nitro
- a method of adding a xyl radical antioxidant, a hindered phenol antioxidant, a basic inorganic substance, or a hindered amine antioxidant is disclosed.
- Patent Document 6 discloses a method of adding a small amount of an organic amine to a sulfolane derivative.
- JP 2007-059611 A JP 2006-237307 A Japanese Unexamined Patent Publication No. Sho 63-12122 Japanese Patent Laid-Open No. 11-255765 JP 2009-215369 A International Publication No. 2012/098811
- the solvent produced using the method disclosed in Patent Document 6 has a problem that the amount of sulfur dioxide can be reduced for a short time at a high temperature, but cannot be sufficiently reduced for a long time. Moreover, there existed a problem that coagulation
- An object of the present invention is to provide a solvent for an electrochemical device electrolyte that is chemically stable for a long time at a high temperature and has a stable liquid state at a low temperature.
- the present invention contains a cyclic sulfone compound represented by the following formula (1), a chain alkyl sulfone compound represented by the following formula (2), an organic amine compound and / or 4-tert-butylcatechol. It is a solvent for an electrochemical device electrolyte.
- R represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms.
- R 1 and R 2 each represent a linear or branched alkyl group having 1 to 5 carbon atoms, and may be independently the same or different from each other.
- the inventors of the present invention have included a specific cyclic sulfone compound and a specific chain alkyl sulfone compound as the sulfone compound, and further an electrochemical containing an organic amine compound and / or 4-tert-butylcatechol. It has been found that the solvent for the device electrolyte is chemically stable for a long time at a high temperature and has a stable liquid state even at a low temperature, and the present invention has been completed.
- the solvent for an electrochemical device electrolyte of the present invention contains a cyclic sulfone compound represented by the formula (1) (hereinafter also simply referred to as “cyclic sulfone compound”).
- the cyclic sulfone compound is electrically stable and can be suitably used as a solvent for an electrolytic solution.
- R represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms. When R is an alkyl group having 7 or more carbon atoms, the viscosity of the obtained electrochemical device electrolyte is remarkably increased, and the electrical conductivity is deteriorated.
- cyclic sulfone compound examples include sulfolane, 3-methyl sulfolane, 3-ethyl sulfolane, 3-propyl sulfolane, 3-butyl sulfolane, 3-pentyl sulfolane, 3-isopropyl sulfolane, 3-isobutyl sulfolane, 3-isopentyl.
- examples include sulfolane. Of these, sulfolane is preferred because of its low viscosity and excellent electrical stability.
- These cyclic sulfone compounds may be used alone or in combination of two or more.
- the solvent for an electrochemical device electrolyte of the present invention contains a chain alkylsulfone compound represented by the above formula (2) (hereinafter also simply referred to as “chain alkylsulfone compound”).
- chain alkylsulfone compound represented by the above formula (2)
- the solvent for an electrochemical device electrolyte of the present invention has a stable liquid state even at a low temperature.
- R 1 and R 2 each represent a linear or branched alkyl group having 1 to 5 carbon atoms, and are each independently the same or different from each other.
- R 1 and R 2 are preferably different, and the difference in carbon number between R 1 and R 2 is more preferably 1 to 3, and 1 or 2 More preferably it is.
- R 1 and R 2 preferably have 3 or less carbon atoms.
- R 1 and R 2 is preferably a branched alkyl group.
- chain alkylsulfone compound examples include dimethylsulfone, diethylsulfone, dipropylsulfone, dibutylsulfone, dipentylsulfone, ethylmethylsulfone, ethylpropylsulfone, ethylisopropylsulfone, ethylbutylsulfone, ethylisobutylsulfone, isopropylsec- Examples include butyl sulfone, ethyl pentyl sulfone, ethyl isopentyl sulfone, butyl pentyl sulfone, and isobutyl isopentyl sulfone. Of these, ethyl isopropyl sulfone and ethyl methyl sulfone are preferable. These chain alkyl sulfone compounds may be used alone or in combination
- the content of the chain alkyl sulfone compound is preferably 10 parts by mass with a preferable lower limit of 40 parts by mass with respect to a total of 100 parts by mass of the cyclic sulfone compound and the chain alkyl sulfone compound.
- the content of the chain alkyl sulfone compound is less than 10 parts by mass, the resulting electrochemical device electrolyte may be solidified or increased in viscosity at a low temperature or inferior in electrical conductivity at a low temperature. There is.
- the content of the chain alkyl sulfone compound exceeds 40 parts by mass, the obtained electrochemical device electrolyte solution may be inferior in electrical stability or chemical stability.
- a more preferable upper limit of the content of the chain alkyl sulfone compound is 30 parts by mass.
- the chain alkyl sulfone compound preferably has a boiling point of 240 ° C. or higher in order to impart high heat resistance and high durability to the electrochemical device.
- the melting point of the chain alkyl sulfone compound is preferably 0 ° C. or lower in order to ensure stable operation of the electrochemical device at a low temperature.
- the heat generation starting temperature of the chain alkyl sulfone compound is preferably 200 ° C. or higher in order to ensure the thermal stability of the electrochemical device.
- the solvent for an electrochemical device electrolyte of the present invention contains an organic amine compound and / or 4-tert-butylcatechol.
- the organic amine compound and the 4-tert-butylcatechol have a role of suppressing the decomposition reaction of the cyclic sulfone compound and the chain alkyl sulfone compound.
- organic amine compound examples include primary amine compounds such as methylamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, heptylamine, octylamine, nonylamine, monoethanolamine, monoisopropanolamine, and benzylamine.
- primary amine compounds such as methylamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, heptylamine, octylamine, nonylamine, monoethanolamine, monoisopropanolamine, and benzylamine.
- Secondary amine compounds such as dimethylamine, diethylamine, dipropylamine, dibutylamine, dipentylamine, dihexylamine, diheptylamine, dioctylamine, dinonylamine, diethanolamine, diisopropanolamine, trimethylamine, triethylamine, tripropylamine , Tributylamine, tripentylamine, trihexylamine, triheptylamine, trioctylamine, trinonylamine, trie Noruamin, tertiary amine compounds such as triisopropanolamine and the like. Of these, primary amine compounds and secondary amine compounds are preferred from the viewpoints of price and availability.
- These organic amine compounds may be used alone or in combination of two or more.
- the content of the organic amine compound and / or the 4-tert-butylcatechol is preferably 0.0001 parts by mass with respect to a total of 100 parts by mass of the cyclic sulfone compound and the chain alkyl sulfone compound, preferably The upper limit is 0.4 parts by mass.
- the content of the organic amine compound and / or the 4-tert-butylcatechol is less than 0.0001 part by mass, the effect of suppressing the decomposition reaction of the cyclic sulfone compound and the chain alkyl sulfone compound is sufficiently exerted. It may not be done.
- the “content of the organic amine compound and / or 4-tert-butylcatechol” includes any one of the organic amine compound and 4-tert-butylcatechol. One content is represented, and when both the organic amine compound and 4-tert-butylcatechol are contained, the total content is represented.
- the solvent for an electrochemical device electrolyte of the present invention preferably contains only the cyclic sulfone compound, the chain alkyl sulfone compound, and the organic amine compound and / or the 4-tert-butylcatechol.
- Other organic solvents may be contained as long as the object of the invention is not impaired.
- the other organic solvents include ethylene carbonate, propylene carbonate, butylene carbonate, dimethyl carbonate, ⁇ -butyrolactone, 1,3-dioxolane, acetonitrile, propionitrile, butyronitrile, dimethylformamide, 1,2-dimethoxyethane, tetrahydrofuran, Examples thereof include 2-methyltetrahydrofuran.
- the solvent for an electrochemical device electrolyte of the present invention preferably has a viscosity of 11 mPa ⁇ s or less measured at 25 ° C. and 100 rpm using a rotary viscometer.
- the viscosity of the solvent for an electrochemical device electrolyte exceeds 11 mPa ⁇ s, the electrical characteristics of the obtained electrochemical device may be deteriorated.
- the solvent for an electrochemical device electrolyte of the present invention can be suitably used for, for example, a secondary battery, an aluminum electrolytic capacitor, an electric double layer capacitor, etc. used for a power source for electronic equipment, a power storage power source, a power source for automobiles and the like. .
- the present invention it is possible to provide a solvent for an electrochemical device electrolyte solution that is chemically stable at a high temperature for a long time and has a stable liquid state at a low temperature.
- Example 1 80 parts by mass of sulfolane as a cyclic sulfone compound, 20 parts by mass of ethyl methyl sulfone as a chain alkyl sulfone compound, and 0.1 parts by mass of monoethanolamine were mixed to prepare a solvent for an electrochemical device electrolyte.
- Example 2 A solvent for an electrochemical device electrolyte was prepared in the same manner as in Example 1 except that 20 parts by mass of ethyl isopropyl sulfone was used instead of ethyl methyl sulfone as the chain alkyl sulfone compound.
- Example 3 A solvent for an electrochemical device electrolyte was prepared in the same manner as in Example 1 except that 0.1 part by mass of 4-tert-butylcatechol was used instead of monoethanolamine.
- Example 4 Example 1 except that 20 parts by mass of ethyl isopropyl sulfone was used instead of ethyl methyl sulfone and 0.1 part by mass of 4-tert-butylcatechol was used instead of monoethanolamine as the chain alkyl sulfone compound. In the same manner, a solvent for an electrochemical device electrolyte was prepared.
- Example 5 A solvent for an electrochemical device electrolyte was prepared in the same manner as in Example 1 except that the amount of sulfolane was changed to 90 parts by mass and the amount of ethyl methyl sulfone was changed to 10 parts by mass.
- Example 6 A solvent for an electrochemical device electrolyte was prepared in the same manner as in Example 1 except that the amount of sulfolane was changed to 60 parts by mass and the amount of ethyl methyl sulfone was changed to 40 parts by mass.
- Example 7 A solvent for an electrochemical device electrolyte was prepared in the same manner as in Example 2 except that the amount of sulfolane was changed to 90 parts by mass and the amount of ethyl isopropyl sulfone was changed to 10 parts by mass.
- Example 8 A solvent for an electrochemical device electrolyte was prepared in the same manner as in Example 2 except that the amount of sulfolane was changed to 60 parts by mass and the amount of ethylisopropyl sulfone was changed to 40 parts by mass.
- Thermal stability test 1 250 mL of the electrochemical device electrolyte solution obtained in each example and each comparative example was added to a 500 mL flask, and nitrogen gas was bubbled through the electrochemical device electrolyte solution in the flask at a flow rate of 83 mL / min. . While introducing the blown-through gas into a gas suction bottle containing 100 mL of 3% hydrogen peroxide as an absorbing solution of sulfur dioxide, the temperature of the solvent for the electrochemical device electrolyte in the flask was about 20 ⁇ 20 ° C. The temperature was raised over a period of minutes.
- Thermal stability test 2 250 mL of the electrochemical device electrolyte solution obtained in each Example and each Comparative Example was added to a 500 mL flask, and the flask was immersed in an oil bath at 180 ⁇ 2 ° C. Immediately after immersing the flask in the oil bath (0h), 2 hours after immersing the flask in the oil bath (2h), 4 hours (4h), and 8 hours (8h) for the electrochemical device electrolyte The amount of sulfur dioxide in the solvent was determined by ion chromatography and used as the amount of sulfur dioxide generated. The results are shown in Table 1.
- the solvent for the electrochemical device electrolyte obtained in the example has a lower sulfur dioxide generation than the solvent for the electrochemical device electrolyte obtained in the comparative example.
- the solvent for the electrochemical device electrolyte obtained in the comparative example when exposed to a high temperature for a long time, the solvent for the electrochemical device electrolyte obtained in the comparative example generates a large amount of sulfur dioxide. It can be seen that the amount of sulfur dioxide generated in the solvent for the electrochemical device electrolyte obtained in the examples is maintained at a low value.
- the solvent for an electrochemical device electrolyte obtained in the examples maintains a low viscosity even at 20 ° C. and has a stable liquid state.
- the electrolyte prepared using the solvent for the electrochemical device electrolyte obtained in Examples 1 and 2 has a wide range of 20 ° C. to ⁇ 30 ° C. It can be seen that excellent conductivity is exhibited even in the temperature range. In addition, the conductivity varies depending on the type of chain sulfone compound used. This indicates that higher electrical conductivity can be provided by changing the chain sulfone compound according to the electrolyte used.
- the present invention it is possible to provide a solvent for an electrochemical device electrolyte solution that is chemically stable at a high temperature for a long time and has a stable liquid state at a low temperature.
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Abstract
Description
一般に、これら電気化学デバイスに用いられる電解液用溶媒としては、例えば、プロピレンカーボネート、エチレンカーボネート、ジエチルカーボネート等の環状炭酸エステル、鎖状炭酸エステル、γ‐ブチロラクトン、及び、それらを基本骨格とした誘導体等が挙げられる。例えば、特許文献1、2には、γ-ブチロラクトンを用いた電解コンデンサが開示されている。
デバイスに膨れが生じると、該デバイスの機器への搭載に支障が生じたり、デバイスの信頼性が低下したりする。
本発明は、高温下で長時間化学的に安定であり、かつ、低温において安定した液状を有する電気化学デバイス電解液用溶媒を提供することを目的とする。
本発明者らは、特許文献6に開示された方法を用いて製造された電解液用溶媒が二酸化硫黄量を長時間低減できない原因は、この方法が、発生した二酸化硫黄を中和するものであって、二酸化硫黄を発生させるスルホン化合物の分解反応自体を抑制するものではないことであると考えた。また、スルホン化合物としてスルホラン誘導体のみを用いているため、低温下で凝固又は高粘度化していると考えた。
そこで本発明者らは鋭意検討した結果、スルホン化合物として特定の環状スルホン化合物と特定の鎖状アルキルスルホン化合物とを含有し、更に有機アミン化合物及び/又は4-tert-ブチルカテコールを含有する電気化学デバイス電解液用溶媒は、高温下で長時間化学的に安定であり、低温においても安定した液状を有するものとなることを見出し、本発明を完成させるに至った。
前記式(1)中、Rは、水素原子、又は、直鎖状若しくは分岐鎖状の炭素数1~6のアルキル基を示す。前記Rが炭素数7以上のアルキル基であると、得られる電気化学デバイス電解液の粘度が著しく高くなり、電気伝導性が悪化する。
また、R1及び/又はR2の炭素数が6以上であると、得られる電気化学デバイス電解液の粘度が著しく高くなり、電気伝導性が悪化する。R1、R2の炭素数は、3以下であることが好ましい。
更に、融点が低くなることから、R1及びR2は、分岐鎖状のアルキル基であることが好ましい。
前記鎖状アルキルスルホン化合物の融点は、電気化学デバイスの低温での安定動作を保証するため、0℃以下であることが好ましい。
前記鎖状アルキルスルホン化合物の発熱開始温度は、電気化学デバイスの熱安定性を保証するため、200℃以上であることが好ましい。
なかでも、価格や入手のしやすさの観点から、第1級アミン化合物及び第2級アミン化合物が好ましく、ブチルアミン、オクチルアミン、モノエタノールアミン、モノイソプロパノールアミン、ベンジルアミン、ジメチルアミン、ジエチルアミン、ジオクチルアミン、及び、ジエタノールアミンからなる群より選択される少なくとも1種がより好ましく、モノエタノールアミンが更に好ましい。これら有機アミン化合物は、単独で使用してもよいし、2種以上を組み合わせて使用してもよい。
なお、本明細書において前記「有機アミン化合物及び/又は4-tert-ブチルカテコールの含有量」は、有機アミン化合物と4-tert-ブチルカテコールとのうちいずれか一方を含有する場合は、含有する一方の含有量を表し、有機アミン化合物と4-tert-ブチルカテコールとの両方を含有する場合は、合計の含有量を表す。
環状スルホン化合物としてスルホラン80質量部と、鎖状アルキルスルホン化合物としてエチルメチルスルホン20質量部と、モノエタノールアミン0.1質量部とを混合し、電気化学デバイス電解液用溶媒を調製した。
鎖状アルキルスルホン化合物として、エチルメチルスルホンに代えてエチルイソプロピルスルホンを20質量部配合したこと以外は、実施例1と同様にして電気化学デバイス電解液用溶媒を調製した。
モノエタノールアミンに代えて4-tert-ブチルカテコールを0.1質量部配合したこと以外は、実施例1と同様にして電気化学デバイス電解液用溶媒を調製した。
鎖状アルキルスルホン化合物として、エチルメチルスルホンに代えてエチルイソプロピルスルホンを20質量部配合し、モノエタノールアミンに代えて4-tert-ブチルカテコールを0.1質量部配合したこと以外は、実施例1と同様にして電気化学デバイス電解液用溶媒を調製した。
スルホランの配合量を90質量部に変更し、エチルメチルスルホンの配合量を10質量部に変更したこと以外は、実施例1と同様にして電気化学デバイス電解液用溶媒を調製した。
スルホランの配合量を60質量部に変更し、エチルメチルスルホンの配合量を40質量部に変更したこと以外は、実施例1と同様にして電気化学デバイス電解液用溶媒を調製した。
スルホランの配合量を90質量部に変更し、エチルイソプロピルスルホンの配合量を10質量部に変更したこと以外は、実施例2と同様にして電気化学デバイス電解液用溶媒を調製した。
スルホランの配合量を60質量部に変更し、エチルイソプロピルスルホンの配合量を40質量部に変更したこと以外は、実施例2と同様にして電気化学デバイス電解液用溶媒を調製した。
モノエタノールアミンを配合しなかったこと以外は、実施例1と同様にして電気化学デバイス電解液用溶媒を調製した。
モノエタノールアミンを配合しなかったこと以外は、実施例2と同様にして電気化学デバイス電解液用溶媒を調製した。
実施例及び比較例で得られた電気化学デバイス電解液用溶媒について以下の評価を行った。
500mL容のフラスコに各実施例及び各比較例で得られた電気化学デバイス電解液用溶媒250mLを加え、フラスコ内の電気化学デバイス電解液用溶媒に、窒素ガスを83mL/minの流速で通気した。吹き抜けたガスを、二酸化硫黄の吸収液として3%過酸化水素水100mLを含むガス吸引瓶に導入しながら、フラスコ内の電気化学デバイス電解液用溶媒の温度が180±2℃となるまで約20分間かけて昇温した。電気化学デバイス電解液用溶媒の温度を180±2℃に保ちながら、窒素ガスを83mL/minの流速で1時間通気した。その後、窒素ガスを40mL/minの流速で通気しながら、電気化学デバイス電解液用溶媒の温度が100℃になるまで放冷した。放冷後、吸収瓶を取り外し、吸収液中の二酸化硫黄量をイオンクロマトグラフィーにより定量し、二酸化硫黄発生量とした。結果を表1に示した。
500mL容のフラスコに各実施例及び各比較例で得られた電気化学デバイス電解液用溶媒250mLを加え、180±2℃のオイルバスにフラスコを浸した。オイルバスにフラスコを浸した直後(0h)、オイルバスにフラスコを浸してから2時間後(2h)、4時間後(4h)、8時間後(8h)のフラスコ内の電気化学デバイス電解液用溶媒の二酸化硫黄量をイオンクロマトグラフィーにより定量し、二酸化硫黄発生量とした。結果を表1に示した。
各実施例及び各比較例で得られた電気化学デバイス電解液用溶媒について、回転式粘度計(東機産業社製、「DIGITAL VISCOMETER DVH-EII」)を使用して、100rpmの条件で20℃、25℃、及び、35℃における粘度を測定した。校正には日本グリース社製の粘度計校正標準液を使用した。結果を表1に示した。
また、「(熱安定性試験2)」の結果から、高温下に長時間曝した際、比較例で得られた電気化学デバイス電解液用溶媒が多量の二酸化硫黄を発生しているのに対し、実施例で得られた電気化学デバイス電解液用溶媒の二酸化硫黄発生量は低い値を維持していることがわかる。
更に、「(粘度測定)」の結果から、実施例で得られた電気化学デバイス電解液用溶媒は、20℃でも低い粘度を維持して安定した液状を有していることがわかる。
実施例1、2で得られた電気化学デバイス電解液用溶媒100gに対し、電解質としてテトラエチルアンモニウムテトラフルオロボレート14.11gを溶解させ、電気化学デバイス電解液を調製した。調製した電気化学デバイス電解液の20℃から-30℃における導電率を、抵抗計(HIOKI社製、「3532-50LCR HiTESTER」)を使用して測定した。結果を表2に示した。
Claims (5)
- 有機アミン化合物は、ブチルアミン、オクチルアミン、モノエタノールアミン、モノイソプロパノールアミン、ベンジルアミン、ジメチルアミン、ジエチルアミン、ジオクチルアミン、及び、ジエタノールアミンからなる群より選択される少なくとも1種であることを特徴とする請求項1記載の電気化学デバイス電解液用溶媒。
- 有機アミン化合物は、モノエタノールアミンであることを特徴とする請求項2記載の電気化学デバイス電解液用溶媒。
- 環状スルホン化合物と鎖状アルキルスルホン化合物との合計100質量部に対する鎖状アルキルスルホン化合物の含有量が10~40質量部であることを特徴とする請求項1、2又は3記載の電気化学デバイス電解液用溶媒。
- 環状スルホン化合物と鎖状アルキルスルホン化合物との合計100質量部に対する有機アミン化合物及び/又は4-tert-ブチルカテコールの含有量が0.0001~0.4質量部であることを特徴とする請求項1、2、3又は4記載の電気化学デバイス電解液用溶媒。
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2014
- 2014-04-16 WO PCT/JP2014/060826 patent/WO2015159386A1/ja active Application Filing
- 2014-04-16 KR KR1020167021089A patent/KR20160144959A/ko not_active Application Discontinuation
- 2014-04-16 EP EP14889457.9A patent/EP3133623B1/en not_active Not-in-force
- 2014-04-16 CN CN201480077945.1A patent/CN106165043B/zh not_active Expired - Fee Related
- 2014-04-16 US US15/128,053 patent/US20170098859A1/en not_active Abandoned
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JP2008034233A (ja) * | 2006-07-28 | 2008-02-14 | Nec Tokin Corp | リチウムイオン二次電池 |
JP2011023330A (ja) * | 2009-06-18 | 2011-02-03 | Panasonic Corp | 蓄電デバイス用非水溶媒および蓄電デバイス用非水電解液、ならびに、これらを用いた蓄電デバイス、リチウム二次電池および電気二重層キャパシタ |
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US20170098859A1 (en) | 2017-04-06 |
CN106165043A (zh) | 2016-11-23 |
EP3133623A1 (en) | 2017-02-22 |
EP3133623A4 (en) | 2017-10-11 |
EP3133623B1 (en) | 2018-11-21 |
KR20160144959A (ko) | 2016-12-19 |
CN106165043B (zh) | 2019-03-26 |
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