JP2009161537A - テトラフルオロアルミン酸有機オニウム塩の製造方法及びテトラフルオロアルミン酸有機オニウム塩 - Google Patents
テトラフルオロアルミン酸有機オニウム塩の製造方法及びテトラフルオロアルミン酸有機オニウム塩 Download PDFInfo
- Publication number
- JP2009161537A JP2009161537A JP2009013110A JP2009013110A JP2009161537A JP 2009161537 A JP2009161537 A JP 2009161537A JP 2009013110 A JP2009013110 A JP 2009013110A JP 2009013110 A JP2009013110 A JP 2009013110A JP 2009161537 A JP2009161537 A JP 2009161537A
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- JP
- Japan
- Prior art keywords
- organic onium
- group
- tetrafluoroaluminate
- onium salt
- ethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 33
- -1 1,2,3,4-tetramethylimidazolinium tetrafluoroaluminate Chemical compound 0.000 claims abstract description 47
- 239000002904 solvent Substances 0.000 claims abstract description 38
- XTXFDUABTPNTFB-UHFFFAOYSA-K trifluoroalumane;hydrate Chemical compound O.F[Al](F)F XTXFDUABTPNTFB-UHFFFAOYSA-K 0.000 claims abstract description 20
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims abstract description 9
- PCXWYMXJVNPICR-UHFFFAOYSA-K aluminum;1-ethyl-2,3-dimethylimidazolidin-1-ium;tetrafluoride Chemical compound [F-].[F-].[F-].[F-].[Al+3].CC[NH+]1CCN(C)C1C PCXWYMXJVNPICR-UHFFFAOYSA-K 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims description 59
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 9
- 238000002425 crystallisation Methods 0.000 claims description 9
- 230000008025 crystallization Effects 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- JIFXKZJGKSXAGZ-UHFFFAOYSA-N 1-ethyl-2,3-dimethylimidazolidine Chemical group CCN1CCN(C)C1C JIFXKZJGKSXAGZ-UHFFFAOYSA-N 0.000 claims description 5
- TXBSWQWDLFJQMU-UHFFFAOYSA-N 4-(chloromethyl)-1,2-diethoxybenzene Chemical group CCOC1=CC=C(CCl)C=C1OCC TXBSWQWDLFJQMU-UHFFFAOYSA-N 0.000 claims description 5
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 5
- DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000005910 alkyl carbonate group Chemical group 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 150000004693 imidazolium salts Chemical group 0.000 claims description 4
- 125000005496 phosphonium group Chemical group 0.000 claims description 4
- KYRYHBRYSSBWLU-UHFFFAOYSA-N 1,2,3,4-tetramethylimidazolidine Chemical compound CC1CN(C)C(C)N1C KYRYHBRYSSBWLU-UHFFFAOYSA-N 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- 125000005156 substituted alkylene group Chemical group 0.000 claims description 3
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 17
- 238000000034 method Methods 0.000 abstract description 17
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000003990 capacitor Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 9
- 239000008151 electrolyte solution Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000003792 electrolyte Substances 0.000 description 7
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 description 4
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- IRGDPGYNHSIIJJ-UHFFFAOYSA-N 1-ethyl-2,3-dimethylimidazol-3-ium Chemical compound CCN1C=C[N+](C)=C1C IRGDPGYNHSIIJJ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OXFHNKYFIVWAAT-UHFFFAOYSA-N 2-ethyl-1,3-dimethylimidazol-1-ium Chemical compound CCC=1N(C)C=C[N+]=1C OXFHNKYFIVWAAT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- GARJMFRQLMUUDD-UHFFFAOYSA-N 1,1-dimethylpyrrolidin-1-ium Chemical compound C[N+]1(C)CCCC1 GARJMFRQLMUUDD-UHFFFAOYSA-N 0.000 description 2
- OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical class C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 description 2
- DNSADNILRQYBAB-UHFFFAOYSA-N 1,2,3,4-tetramethylimidazol-1-ium Chemical compound CC1=C[N+](C)=C(C)N1C DNSADNILRQYBAB-UHFFFAOYSA-N 0.000 description 2
- KCUGPPHNMASOTE-UHFFFAOYSA-N 1,2,3-trimethylimidazol-1-ium Chemical compound CC=1N(C)C=C[N+]=1C KCUGPPHNMASOTE-UHFFFAOYSA-N 0.000 description 2
- QDRFNXRYFUFFLV-UHFFFAOYSA-N 1,2,3-trimethylimidazolidine Chemical compound CC1N(C)CCN1C QDRFNXRYFUFFLV-UHFFFAOYSA-N 0.000 description 2
- IFGGXMRDYJZDJE-UHFFFAOYSA-N 1,2-dimethyl-3-phenylimidazol-1-ium Chemical compound CN1C=C[N+](C=2C=CC=CC=2)=C1C IFGGXMRDYJZDJE-UHFFFAOYSA-N 0.000 description 2
- UHIFZEQUAVFJKZ-UHFFFAOYSA-N 1,2-dimethyl-3-phenylimidazolidine Chemical compound CC1N(C)CCN1C1=CC=CC=C1 UHIFZEQUAVFJKZ-UHFFFAOYSA-N 0.000 description 2
- CDIWYWUGTVLWJM-UHFFFAOYSA-N 1,3,4-trimethylimidazol-1-ium Chemical compound CC1=C[N+](C)=CN1C CDIWYWUGTVLWJM-UHFFFAOYSA-N 0.000 description 2
- IBXOTQVBNFBJFM-UHFFFAOYSA-N 1,3,4-trimethylimidazolidine Chemical compound CC1CN(C)CN1C IBXOTQVBNFBJFM-UHFFFAOYSA-N 0.000 description 2
- XLJSMWDFUFADIA-UHFFFAOYSA-N 1,3-diethylimidazol-1-ium Chemical compound CCN1C=C[N+](CC)=C1 XLJSMWDFUFADIA-UHFFFAOYSA-N 0.000 description 2
- BEUKLVYOGCCEPF-UHFFFAOYSA-N 1,3-diethylimidazolidine Chemical compound CCN1CCN(CC)C1 BEUKLVYOGCCEPF-UHFFFAOYSA-N 0.000 description 2
- NVHSSCNZSOYDCO-UHFFFAOYSA-N 1,3-dimethyl-2-pentylimidazol-1-ium Chemical compound CCCCCC=1N(C)C=C[N+]=1C NVHSSCNZSOYDCO-UHFFFAOYSA-N 0.000 description 2
- OBTFKSNFKVPPFY-UHFFFAOYSA-N 1,3-dimethyl-2-phenylimidazol-1-ium Chemical compound CN1C=C[N+](C)=C1C1=CC=CC=C1 OBTFKSNFKVPPFY-UHFFFAOYSA-N 0.000 description 2
- QISTUHYRFABJSG-UHFFFAOYSA-N 1,3-dimethyl-2-phenylimidazolidine Chemical class CN1CCN(C)C1C1=CC=CC=C1 QISTUHYRFABJSG-UHFFFAOYSA-N 0.000 description 2
- IJDNIXNJORNVTA-UHFFFAOYSA-N 1,3-dimethyl-2-propylimidazol-1-ium Chemical compound CCCC=1N(C)C=C[N+]=1C IJDNIXNJORNVTA-UHFFFAOYSA-N 0.000 description 2
- CXSBCXDVNBHHOP-UHFFFAOYSA-N 1,3-dimethyl-2-propylimidazolidine Chemical compound CCCC1N(C)CCN1C CXSBCXDVNBHHOP-UHFFFAOYSA-N 0.000 description 2
- DSPUBTKMQXMJCI-UHFFFAOYSA-N 1,3-dimethylbenzimidazol-3-ium Chemical compound C1=CC=C2N(C)C=[N+](C)C2=C1 DSPUBTKMQXMJCI-UHFFFAOYSA-N 0.000 description 2
- SMWUDAKKCDQTPV-UHFFFAOYSA-N 1,3-dimethylimidazolidine Chemical compound CN1CCN(C)C1 SMWUDAKKCDQTPV-UHFFFAOYSA-N 0.000 description 2
- HVVRUQBMAZRKPJ-UHFFFAOYSA-N 1,3-dimethylimidazolium Chemical compound CN1C=C[N+](C)=C1 HVVRUQBMAZRKPJ-UHFFFAOYSA-N 0.000 description 2
- HGIKIBHZIYNEKO-UHFFFAOYSA-N 1-benzyl-2,3-dimethylimidazol-3-ium Chemical compound C1=C[N+](C)=C(C)N1CC1=CC=CC=C1 HGIKIBHZIYNEKO-UHFFFAOYSA-N 0.000 description 2
- KUAWBKRDALUYBI-UHFFFAOYSA-N 1-benzyl-2,3-dimethylimidazolidine Chemical compound CC1N(C)CCN1CC1=CC=CC=C1 KUAWBKRDALUYBI-UHFFFAOYSA-N 0.000 description 2
- CHENRKIAWPQCBU-UHFFFAOYSA-N 1-benzyl-3-methylimidazolidine Chemical compound C1N(C)CCN1CC1=CC=CC=C1 CHENRKIAWPQCBU-UHFFFAOYSA-N 0.000 description 2
- VMZNMSUASLBPDS-UHFFFAOYSA-N 1-ethyl-2-methyl-4,5-dihydroimidazole Chemical compound CCN1CCN=C1C VMZNMSUASLBPDS-UHFFFAOYSA-N 0.000 description 2
- JOTQIXXCBHIDKJ-UHFFFAOYSA-N 1-ethyl-3-methylimidazolidine Chemical compound CCN1CCN(C)C1 JOTQIXXCBHIDKJ-UHFFFAOYSA-N 0.000 description 2
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 description 2
- MEKMPQZLPWXFTF-UHFFFAOYSA-N 1-methyl-3-phenylimidazolidine Chemical compound C1N(C)CCN1C1=CC=CC=C1 MEKMPQZLPWXFTF-UHFFFAOYSA-N 0.000 description 2
- UJBYZFKDBNQRBW-UHFFFAOYSA-N 2-benzyl-1,3-dimethylimidazol-1-ium Chemical compound CN1C=C[N+](C)=C1CC1=CC=CC=C1 UJBYZFKDBNQRBW-UHFFFAOYSA-N 0.000 description 2
- DFLRGRAIPLYIIM-UHFFFAOYSA-N 2-ethyl-1,3,4-trimethylimidazol-1-ium Chemical compound CCC=1N(C)C(C)=C[N+]=1C DFLRGRAIPLYIIM-UHFFFAOYSA-N 0.000 description 2
- LLTLVSUMJNRKPD-UHFFFAOYSA-N 2-ethyl-1,3,4-trimethylimidazolidine Chemical compound CCC1N(C)CC(C)N1C LLTLVSUMJNRKPD-UHFFFAOYSA-N 0.000 description 2
- CQBZHSCDPNAGLN-UHFFFAOYSA-N 2-heptyl-1,3-dimethylimidazol-1-ium Chemical compound CCCCCCCC=1N(C)C=C[N+]=1C CQBZHSCDPNAGLN-UHFFFAOYSA-N 0.000 description 2
- SHTANHZPDWEAAR-UHFFFAOYSA-N 2-heptyl-1,3-dimethylimidazolidine Chemical compound CCCCCCCC1N(C)CCN1C SHTANHZPDWEAAR-UHFFFAOYSA-N 0.000 description 2
- 229910016569 AlF 3 Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N Vilsmeier-Haack reagent Natural products CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- ZJHQDSMOYNLVLX-UHFFFAOYSA-N diethyl(dimethyl)azanium Chemical compound CC[N+](C)(C)CC ZJHQDSMOYNLVLX-UHFFFAOYSA-N 0.000 description 2
- YOMFVLRTMZWACQ-UHFFFAOYSA-N ethyltrimethylammonium Chemical compound CC[N+](C)(C)C YOMFVLRTMZWACQ-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- XTPRURKTXNFVQT-UHFFFAOYSA-N hexyl(trimethyl)azanium Chemical compound CCCCCC[N+](C)(C)C XTPRURKTXNFVQT-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000004255 ion exchange chromatography Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000003444 phase transfer catalyst Substances 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 2
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 2
- 125000001984 thiazolidinyl group Chemical group 0.000 description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 2
- SEACXNRNJAXIBM-UHFFFAOYSA-N triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC SEACXNRNJAXIBM-UHFFFAOYSA-N 0.000 description 2
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 2
- HNVRIVKDRYGTED-UHFFFAOYSA-N 1,1-diethylpiperidin-1-ium Chemical compound CC[N+]1(CC)CCCCC1 HNVRIVKDRYGTED-UHFFFAOYSA-N 0.000 description 1
- PWZSCBSKFVJMJH-UHFFFAOYSA-N 1,1-diethylpyrrolidin-1-ium Chemical compound CC[N+]1(CC)CCCC1 PWZSCBSKFVJMJH-UHFFFAOYSA-N 0.000 description 1
- JONPEMDXBGXQHV-UHFFFAOYSA-N 1,1-dimethyl-4,5-dihydroimidazol-1-ium Chemical compound C[N+]1(C)CCN=C1 JONPEMDXBGXQHV-UHFFFAOYSA-N 0.000 description 1
- DREZKWDRXQDOGO-UHFFFAOYSA-N 1,2,3,4,5-pentamethylimidazol-1-ium Chemical compound CC1=C(C)[N+](C)=C(C)N1C DREZKWDRXQDOGO-UHFFFAOYSA-N 0.000 description 1
- GRHNKLNJAYKFIG-UHFFFAOYSA-N 1,2,3-trimethyl-1,3-diazinane Chemical compound CC1N(C)CCCN1C GRHNKLNJAYKFIG-UHFFFAOYSA-N 0.000 description 1
- KBNWCDNOTZWFBD-UHFFFAOYSA-N 1,2,4-trimethyl-3-propylimidazol-1-ium Chemical compound CCCN1C(C)=C[N+](C)=C1C KBNWCDNOTZWFBD-UHFFFAOYSA-N 0.000 description 1
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
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- 230000003287 optical effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
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- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- KLIUHARZXKNLFV-UHFFFAOYSA-N tert-butyl(triethyl)azanium Chemical compound CC[N+](CC)(CC)C(C)(C)C KLIUHARZXKNLFV-UHFFFAOYSA-N 0.000 description 1
- SPJZSTLXABSXII-UHFFFAOYSA-N tert-butyl(trimethyl)azanium Chemical compound CC(C)(C)[N+](C)(C)C SPJZSTLXABSXII-UHFFFAOYSA-N 0.000 description 1
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- 238000012360 testing method Methods 0.000 description 1
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- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
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- CZMILNXHOAKSBR-UHFFFAOYSA-N tetraphenylazanium Chemical compound C1=CC=CC=C1[N+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CZMILNXHOAKSBR-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- DLJBCWLKMQZRFN-UHFFFAOYSA-N triethyl(2-methylpropyl)azanium Chemical compound CC[N+](CC)(CC)CC(C)C DLJBCWLKMQZRFN-UHFFFAOYSA-N 0.000 description 1
- JKDLEQCSDWWVHQ-UHFFFAOYSA-M triethyl(methyl)azanium fluoride trihydrate Chemical compound O.O.O.[F-].CC[N+](C)(CC)CC JKDLEQCSDWWVHQ-UHFFFAOYSA-M 0.000 description 1
- TZWFFXFQARPFJN-UHFFFAOYSA-N triethyl(methyl)phosphanium Chemical compound CC[P+](C)(CC)CC TZWFFXFQARPFJN-UHFFFAOYSA-N 0.000 description 1
- XPLXACTVVUDCNQ-UHFFFAOYSA-N triethyl(propan-2-yl)azanium Chemical compound CC[N+](CC)(CC)C(C)C XPLXACTVVUDCNQ-UHFFFAOYSA-N 0.000 description 1
- WGYXSYLSCVXFDU-UHFFFAOYSA-N triethyl(propyl)azanium Chemical compound CCC[N+](CC)(CC)CC WGYXSYLSCVXFDU-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- COOSQAXLLKTSQO-UHFFFAOYSA-N trimethyl(2-methylpropyl)azanium Chemical compound CC(C)C[N+](C)(C)C COOSQAXLLKTSQO-UHFFFAOYSA-N 0.000 description 1
- ZVFDPYZBJGKPII-UHFFFAOYSA-N trimethyl(nonyl)azanium Chemical compound CCCCCCCCC[N+](C)(C)C ZVFDPYZBJGKPII-UHFFFAOYSA-N 0.000 description 1
- ACZOGADOAZWANS-UHFFFAOYSA-N trimethyl(pentyl)azanium Chemical compound CCCCC[N+](C)(C)C ACZOGADOAZWANS-UHFFFAOYSA-N 0.000 description 1
- BMTHNVMASXVELE-UHFFFAOYSA-N trimethyl(propan-2-yl)azanium Chemical compound CC(C)[N+](C)(C)C BMTHNVMASXVELE-UHFFFAOYSA-N 0.000 description 1
- QDUATGYYXKDLEI-UHFFFAOYSA-N trimethyl(undecyl)azanium Chemical compound CCCCCCCCCCC[N+](C)(C)C QDUATGYYXKDLEI-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical compound C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Abstract
【解決手段】フッ化有機オニウム塩とフッ化アルミニウム水和物を、溶媒の存在下で反応させることを特徴とするテトラフルオロアルミン酸有機オニウムの製造方法である。本方法により新規化合物として、テトラフルオロアルミン酸1−エチル−2,3−ジメチルイミダゾリニウム又はテトラフルオロアルミン酸1,2,3,4−テトラメチルイミダゾリニウムを製造することが出来る。
【選択図】なし
Description
R5〜R7は、それぞれ独立して、水素原子か、又は非置換若しくは置換のアルキル基、シクロアルキル基、アリール基若しくはアラルキル基を表すか;
あるいは、R6及びR7は、R6が結合した窒素原子及びR7が結合した炭素原子と一緒になって、4〜10員環(ここで、該環はヘテロ原子を含んでいてもよい)を形成し、R5は上記で定義したとおりであり、
Xは、非置換若しくは置換のアルキレン基である)
で表されるテトラフルオロアルミン酸有機オニウム塩である。
本発明のテトラフルオロアルミン酸有機オニウム塩の製造方法は、フッ化有機オニウム塩とフッ化アルミニウム水和物とを溶媒の存在下で反応させる。原料のフッ化有機オニウム塩の有機オニウムは、孤立電子対を有する元素(窒素、リンなど)を含む化合物において、これらの孤立電子対にプロトンや他の陽イオンが配位結合して生ずるイオン化合物の総称であり、特に限定されるものではないが、本発明においては、式(I):
R1〜R4は、それぞれ独立して、水素原子(ただし、R1〜R4の2個以上が、水素原子を表すことはないものとする)又は、非置換若しくは置換のアルキル基、シクロアルキル基、アリール基若しくはアラルキル基である;あるいは、R1〜R4の一部又は全部が、Aで示される原子と一緒になって、非置換又は置換の3〜10員環(ここで、該環はヘテロ原子を含んでいてもよい)を形成し、該環の形成に関与していないR1〜R4は、上記で定義したとおりである;そしてAは、窒素原子又はリン原子を表す)
で表される有機オニウムが好ましい。
R5〜R7は、それぞれ独立して、水素原子か、又は非置換若しくは置換のアルキル基、シクロアルキル基、アリール基若しくはアラルキル基を表すか;あるいは、R6及びR7は、R6が結合した窒素原子とR7が結合した炭素原子と一緒になって、4〜10員環(ここで、該環はヘテロ原子を含んでいてもよい)を形成し、R5は上記で定義したとおりであり、
Xは、非置換若しくは置換のアルキレン基である)
で表される、新規なテトラフルオロアルミン酸有機オニウム塩が得られる。
(1)テトラフルオロアルミン酸トリエチルメチルアンモニウムの合成
PFA製丸底フラスコにフッ化アルミニウム三水和物6.90g(50.0mmol)を秤量し、容器内を減圧後、アルゴンガスで置換した。フラスコの口からアルゴンガスを導入しながら、脱水したアセトニトリル100mlを加え、密栓して30分攪拌した。続いて同様にアルゴンガスを導入しながら、フッ化トリエチルメチルアンモニウム三水和物9.46g(50.0mmol)を分割して投入し、更に3時間ほど攪拌した。未反応の固形分を濾別後、溶媒を留去して約9gのテトラフルオロアルミン酸トリエチルメチルアンモニウムの白色粗結晶を得た。これをイソプロパノール10gにより再結晶精製した。収量は5.50g、仕込みからのトータル収率は50%であった。同定は元素分析とNMRにより行い、TG−DTAにより融点を測定した。またイオンクロマトグラフィーにより不純物である塩化物イオン、臭化物イオン及び硫酸イオンを定量した。
分析値:C: 38.40, H: 7.70, N: 6.32, Al: 12.0, F: 33.50
19F-NMR:-190 ppm(六重線、J = 34 Hz、(CD3)2SO溶媒中CFCl3基準)
27Al-NMR: 49 ppm(五重線、J = 34 Hz、(CD3)2SO溶媒中AlCl3・3H2O基準)
融点:320℃(分解)
Cl-濃度:5ppm以下
Br-濃度:5ppm以下
SO4 2-濃度:5ppm以下
上記で得られたテトラフルオロアルミン酸トリエチルメチルアンモニウムを、γ−ブチロラクトンに溶解することにより25重量%濃度の電解液を調製した。この電解液について、調製直後と、125℃での加熱試験を25時間実施した後に、電気伝導率(25℃)を測定した。次に、図1に示す巻回型素子にこの電解液を含浸し、該巻回型素子をアルミニウム外装ケースに収納し、過酸化物で加硫したブチルゴムで封口した構造のアルミ電解コンデンサを作製した(図2)。このアルミ電解コンデンサに、10mAの定電流を125℃にて印加したときの電圧−時間の上昇カーブで、初めにスパイクあるいはシンチレーションが観測された電圧値を耐電圧値とした。使用したアルミ電解コンデンサ素子の仕様は、ケースサイズ10φ×20L、定格電圧200V、静電容量20μFである。
フッ化アルミニウム三水和物のかわりに無水のフッ化アルミニウム4.20g(50mmol)を使用した以外は実施例1と同様に反応を実施した。反応停止後も液中にフッ化アルミニウムが大量に懸濁していたため、反応温度55℃にて更に12時間反応を実施した。しかし反応は進行せず、目的物であるテトラフルオロアルミン酸トリエチルメチルアンモニウムを全く得ることができなかった。
(1)テトラフルオロアルミン酸1−エチル−2,3−ジメチルイミダゾリニウムの合成
100mlオートクレーブ内に1−エチル−2−メチルイミダゾリン11.2g(0.10mol)、炭酸ジメチル18.0g(0.20mol)、メタノール27.2gを投入し、145℃にて8時間反応させることにより、炭酸メチル1−エチル−2,3−ジメチルイミダゾリニウムを収率100%で得た。続いてこの反応液を、リフラックスコンデンサ付きのテフロン製フラスコに移液し、更にフッ化アンモニウム3.70g(0.10mol)を混合して、50℃にて5時間反応させることによりフッ化1−エチル−2,3−ジメチルイミダゾリニウムを収率100%で得た。反応終了後のリフラックスコンデンサにはアンモニアと二酸化炭素によって生成した白色固体が付着しており、またその固体の一部が反応液中に混入していたのでこれをろ過により除去して次の反応工程に供した。
分析値:C: 39.27, H: 6.05, N: 12.76, Al: 11.70
19F-NMR:-190.5 ppm(六重線、J = 35 Hz、(CD3)2SO溶媒中CFCl3基準)
27Al-NMR: 49.6 ppm(五重線、J = 35 Hz、(CD3)2SO溶媒中AlCl3・3H2O基準)
融点:160℃
Cl-濃度:5ppm以下
Br-濃度:5ppm以下
SO4 2-濃度:5ppm以下
このテトラフルオロアルミン酸1−エチル−2,3−ジメチルイミダゾリニウムを、γ−ブチロラクトンに溶解することにより25重量%濃度の電解液を調製した。25℃における電気伝導率は24.1mS/cm、実施例1と同様にして測定した125℃におけるコンデンサの耐電圧は160Vであった。
2 陰極箔
3 セパレータ
4 リード線
5 封口材
6 外装ケース
Claims (13)
- フッ化有機オニウム塩とフッ化アルミニウム水和物とを、溶媒の存在下で反応させることを特徴とする、テトラフルオロアルミン酸有機オニウム塩の製造方法。
- フッ化有機オニウム塩が、アルキル炭酸有機オニウム塩とフッ化アンモニウムとを反応させて得られる、請求項1に記載の製造方法。
- フッ化有機オニウム塩とフッ化アルミニウム水和物とを、溶媒の存在下で反応させて得られるテトラフルオロアルミン酸有機オニウム塩を、炭素数4以下のアルコールを晶析溶媒として用いて晶析することを含む、請求項1又は2に記載の製造方法。
- フッ化有機オニウム塩の有機オニウムが、式(I):
(式中、
R1〜R4は、それぞれ独立して、水素原子(ただし、R1〜R4の2個以上が、水素原子を表すことはないものとする)か、又は非置換若しくは置換のアルキル基、シクロアルキル基、アリール基若しくはアラルキル基であるか;
あるいは、R1〜R4の一部又は全部が、Aで表される原子と一緒になって、非置換若しくは置換の3〜10員環(ここで、該環はヘテロ原子を含んでいてもよい)を形成し、環形成に関与していないR1〜R4は、上記で定義したとおりであり、
そしてAは、窒素原子又はリン原子を表す)
で表されるイオンである、請求項1〜3のいずれか1項に記載の製造方法。 - 有機オニウムが、第四級アンモニウム、第四級ホスホニウム、第四級イミダゾリウム、第四級環状アミジニウム及び第三級アンモニウムからなる群から選ばれるイオンである、請求項1〜4のいずれか1項に記載の製造方法。
- 有機オニウムが、第四級環状アミジニウムである、請求項5に記載の製造方法。
- 有機オニウムの総炭素数が、4〜12である、請求項1〜6のいずれか1項に記載の製造方法。
- 有機オニウムが、1−エチル−2,3−ジメチルイミダゾリニウム又は1,2,3,4−テトラメチルイミダゾリニウムである、請求項1〜7のいずれか1項に記載の製造方法。
- フッ化アルミニウム水和物が、フッ化アルミニウム三水和物である、請求項1〜8のいずれか1項に記載の製造方法。
- 溶媒が、水、メタノール及びアセトニトリルからなる群から選ばれる、請求項1〜9のいずれか1項に記載の製造方法。
- 溶媒が、メタノールである、請求項10に記載の製造方法。
- テトラフルオロアルミン酸1−エチル−2,3−ジメチルイミダゾリニウム又はテトラフルオロアルミン酸1,2,3,4−テトラメチルイミダゾリニウム。
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JP2009121558A Expired - Fee Related JP4924658B2 (ja) | 2001-05-11 | 2009-05-20 | 電解コンデンサ用電解液及びそれを用いた電解コンデンサ |
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JP2011113784A Withdrawn JP2011181956A (ja) | 2001-05-11 | 2011-05-20 | 電解コンデンサ用電解液及びそれを用いた電解コンデンサ |
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US (2) | US7072173B2 (ja) |
EP (1) | EP1394824A4 (ja) |
JP (3) | JP4631975B2 (ja) |
CN (2) | CN100394522C (ja) |
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Families Citing this family (52)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1394824A4 (en) * | 2001-05-11 | 2008-01-23 | Mitsubishi Chem Corp | ELECTROLYTIC SOLUTION FOR AN ELECTROLYTE CONDENSER AND ELECTROLYTE CONDENSER THEREWITH |
AU2003280692A1 (en) * | 2002-10-31 | 2004-05-25 | Mitsubishi Chemical Corporation | Electrolyte for electrolytic capacitor, electrolytic capacitor and process for producing tetrafluoroaluminate salt of organic onium |
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KR101112022B1 (ko) | 2002-11-08 | 2012-02-24 | 미쯔비시 가가꾸 가부시끼가이샤 | 전해 콘덴서용 전해액 및 그것을 이용한 전해 콘덴서 |
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EP3566242A4 (en) | 2017-01-03 | 2020-09-30 | ABB Power Grids Switzerland AG | INSULATION SYSTEM AND CAPACITOR |
JPWO2021241333A1 (ja) * | 2020-05-26 | 2021-12-02 |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01246386A (ja) * | 1987-11-25 | 1989-10-02 | Asahi Glass Co Ltd | オニウム塩の製造方法 |
JPH02106915A (ja) * | 1988-10-15 | 1990-04-19 | Matsushita Electric Ind Co Ltd | 電解コンデンサ駆動用電解液およびその製造方法 |
JPH0867672A (ja) * | 1994-08-29 | 1996-03-12 | Sanyo Chem Ind Ltd | イミダゾリニウム有機酸塩の製造方法 |
JPH11322760A (ja) * | 1998-05-12 | 1999-11-24 | Mitsubishi Chemical Corp | 有機オニウム塩の製造方法 |
JPH11322720A (ja) * | 1998-05-14 | 1999-11-24 | Sanyo Chem Ind Ltd | 4級環状アミジン有機酸塩の製造法 |
JPH11322759A (ja) * | 1998-05-12 | 1999-11-24 | Mitsubishi Chemical Corp | 有機オニウム塩の製造方法 |
JP2000016995A (ja) * | 1998-06-30 | 2000-01-18 | Mitsubishi Chemicals Corp | 4級アンモニウムテトラフルオロボレートの製造方法 |
JP2001220373A (ja) * | 1999-11-29 | 2001-08-14 | Sanyo Chem Ind Ltd | 2置換ジアミンモノアミド化合物の製造法 |
Family Cites Families (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3415687A (en) * | 1966-03-29 | 1968-12-10 | Honeywell Inc | Electric current producing cell |
JPS62288815A (ja) * | 1986-02-21 | 1987-12-15 | Sanyo Chem Ind Ltd | 電解液 |
JPS63122112A (ja) | 1986-11-11 | 1988-05-26 | 旭硝子株式会社 | 新規な電解コンデンサ |
JPH01124210A (ja) * | 1987-11-09 | 1989-05-17 | Matsushita Electric Ind Co Ltd | 電解コンデンサ駆動用電解液 |
GB8804860D0 (en) * | 1988-03-01 | 1988-03-30 | Ici Plc | Solid electrolyte devices |
US5714279A (en) * | 1989-10-24 | 1998-02-03 | The United States Of America As Represented By The Secretary Of The Navy | Non-aqueous lithium cells |
JP2958576B2 (ja) * | 1991-01-24 | 1999-10-06 | 富士写真フイルム株式会社 | 電池用正極材料 |
JPH0513273A (ja) | 1991-07-04 | 1993-01-22 | Matsushita Electric Ind Co Ltd | 電解コンデンサ駆動用電解液 |
JPH06196366A (ja) | 1992-11-09 | 1994-07-15 | Mitsubishi Petrochem Co Ltd | 電解コンデンサ用電解液 |
JPH06196367A (ja) * | 1992-12-24 | 1994-07-15 | Mitsubishi Petrochem Co Ltd | 電解コンデンサ用電解液 |
JP3387144B2 (ja) | 1993-03-30 | 2003-03-17 | 三菱化学株式会社 | 電解コンデンサ用電解液 |
JP3078948B2 (ja) * | 1993-03-31 | 2000-08-21 | 日石三菱株式会社 | 有機溶媒及び電解液 |
US5870275A (en) * | 1993-12-03 | 1999-02-09 | Sanyo Chemical Industries, Ltd. | Electrolyte and electronic component using same |
KR100237116B1 (ko) * | 1993-12-03 | 2000-01-15 | 가케히 데츠오 | 전해액 및 이를 사용한 전기 화학 소자 |
KR100366551B1 (ko) * | 1994-09-29 | 2003-03-12 | 닛뽄 케미콘 가부시끼가이샤 | 전해콘덴서 |
JPH10116629A (ja) * | 1996-10-15 | 1998-05-06 | Mitsui Chem Inc | 非水電解液 |
JP3349399B2 (ja) | 1996-11-01 | 2002-11-25 | 三洋電機株式会社 | リチウム二次電池 |
JPH10233343A (ja) * | 1997-02-19 | 1998-09-02 | Elna Co Ltd | アルミニウム電解コンデンサおよびアルミニウム電解コンデンサ駆動用電解液 |
JP3669804B2 (ja) * | 1997-03-03 | 2005-07-13 | 日本ケミコン株式会社 | 電解コンデンサ用電解液 |
EP0886334B1 (en) | 1997-06-19 | 2001-08-29 | Sanyo Electric Co., Ltd. | Lithium secondary battery |
JP4780812B2 (ja) | 1997-08-01 | 2011-09-28 | 日本ケミコン株式会社 | アルミニウム電解コンデンサ |
TR200001470T2 (tr) * | 1997-11-24 | 2001-03-21 | The Procter & Gamble Company | Yüksek elektrolit muhtevası ve isteğe bağlı faz stabilizörü içeren berrak veya yarı şeffaf sulu kumaş yumuşatıcı terkipleri |
US6166899A (en) | 1997-12-18 | 2000-12-26 | Nippon Chemi-Con Corporation | Electrolyte for electrolytic capacitor and electrolytic capacitor having the same |
JPH11283880A (ja) | 1998-03-31 | 1999-10-15 | Mitsubishi Chemical Corp | 電解コンデンサ用電解液及びそれを用いた電解コンデンサ |
JP2001085281A (ja) * | 1999-09-09 | 2001-03-30 | Honda Motor Co Ltd | 電気二重層コンデンサの配線構造 |
JP3967551B2 (ja) * | 2001-02-08 | 2007-08-29 | 本田技研工業株式会社 | 電気二重層キャパシタ容器の蓋体 |
EP1394824A4 (en) * | 2001-05-11 | 2008-01-23 | Mitsubishi Chem Corp | ELECTROLYTIC SOLUTION FOR AN ELECTROLYTE CONDENSER AND ELECTROLYTE CONDENSER THEREWITH |
-
2002
- 2002-05-10 EP EP02778902A patent/EP1394824A4/en not_active Withdrawn
- 2002-05-10 CN CNB028097165A patent/CN100394522C/zh not_active Expired - Fee Related
- 2002-05-10 CN CN2008100923529A patent/CN101261900B/zh not_active Expired - Fee Related
- 2002-05-10 WO PCT/JP2002/004571 patent/WO2002101773A1/ja active Application Filing
-
2003
- 2003-11-12 US US10/704,803 patent/US7072173B2/en not_active Expired - Lifetime
-
2005
- 2005-12-16 US US11/304,600 patent/US7460357B2/en not_active Expired - Lifetime
-
2009
- 2009-01-23 JP JP2009013110A patent/JP4631975B2/ja not_active Expired - Fee Related
- 2009-05-20 JP JP2009121558A patent/JP4924658B2/ja not_active Expired - Fee Related
-
2011
- 2011-05-20 JP JP2011113784A patent/JP2011181956A/ja not_active Withdrawn
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01246386A (ja) * | 1987-11-25 | 1989-10-02 | Asahi Glass Co Ltd | オニウム塩の製造方法 |
JPH02106915A (ja) * | 1988-10-15 | 1990-04-19 | Matsushita Electric Ind Co Ltd | 電解コンデンサ駆動用電解液およびその製造方法 |
JPH0867672A (ja) * | 1994-08-29 | 1996-03-12 | Sanyo Chem Ind Ltd | イミダゾリニウム有機酸塩の製造方法 |
JPH11322760A (ja) * | 1998-05-12 | 1999-11-24 | Mitsubishi Chemical Corp | 有機オニウム塩の製造方法 |
JPH11322759A (ja) * | 1998-05-12 | 1999-11-24 | Mitsubishi Chemical Corp | 有機オニウム塩の製造方法 |
JPH11322720A (ja) * | 1998-05-14 | 1999-11-24 | Sanyo Chem Ind Ltd | 4級環状アミジン有機酸塩の製造法 |
JP2000016995A (ja) * | 1998-06-30 | 2000-01-18 | Mitsubishi Chemicals Corp | 4級アンモニウムテトラフルオロボレートの製造方法 |
JP2001220373A (ja) * | 1999-11-29 | 2001-08-14 | Sanyo Chem Ind Ltd | 2置換ジアミンモノアミド化合物の製造法 |
Also Published As
Publication number | Publication date |
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EP1394824A4 (en) | 2008-01-23 |
JP4631975B2 (ja) | 2011-02-16 |
CN101261900B (zh) | 2011-02-02 |
US7460357B2 (en) | 2008-12-02 |
US20060092597A1 (en) | 2006-05-04 |
JP2011181956A (ja) | 2011-09-15 |
CN100394522C (zh) | 2008-06-11 |
CN101261900A (zh) | 2008-09-10 |
WO2002101773A1 (en) | 2002-12-19 |
CN1511327A (zh) | 2004-07-07 |
JP2009239291A (ja) | 2009-10-15 |
JP4924658B2 (ja) | 2012-04-25 |
EP1394824A1 (en) | 2004-03-03 |
US7072173B2 (en) | 2006-07-04 |
US20040095708A1 (en) | 2004-05-20 |
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