JP2008034883A - Manufacturing method of nonaqueous electrolytic solution for electric double-layer capacitor - Google Patents
Manufacturing method of nonaqueous electrolytic solution for electric double-layer capacitor Download PDFInfo
- Publication number
- JP2008034883A JP2008034883A JP2007271340A JP2007271340A JP2008034883A JP 2008034883 A JP2008034883 A JP 2008034883A JP 2007271340 A JP2007271340 A JP 2007271340A JP 2007271340 A JP2007271340 A JP 2007271340A JP 2008034883 A JP2008034883 A JP 2008034883A
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- JP
- Japan
- Prior art keywords
- ethyl
- diethyl
- hydrogen fluoride
- electric double
- double layer
- 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.)
- Pending
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- 239000003990 capacitor Substances 0.000 title claims abstract description 28
- 239000008151 electrolyte solution Substances 0.000 title claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 33
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 33
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 15
- 239000011737 fluorine Substances 0.000 claims abstract description 15
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 7
- 239000003463 adsorbent Substances 0.000 claims abstract description 4
- 238000001953 recrystallisation Methods 0.000 claims abstract description 4
- 239000011255 nonaqueous electrolyte Substances 0.000 claims description 19
- 239000003125 aqueous solvent Substances 0.000 claims description 10
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 9
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 7
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000004714 phosphonium salts Chemical group 0.000 claims description 5
- 125000005496 phosphonium group Chemical group 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 claims description 2
- 229910017008 AsF 6 Inorganic materials 0.000 claims description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 2
- 229910018286 SbF 6 Inorganic materials 0.000 claims description 2
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
- PPDFQRAASCRJAH-UHFFFAOYSA-N 2-methylthiolane 1,1-dioxide Chemical compound CC1CCCS1(=O)=O PPDFQRAASCRJAH-UHFFFAOYSA-N 0.000 claims 1
- 238000005868 electrolysis reaction Methods 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- -1 fluorine ions Chemical class 0.000 abstract description 15
- 239000000243 solution Substances 0.000 abstract description 6
- 230000007774 longterm Effects 0.000 abstract description 4
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 239000003792 electrolyte Substances 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- SEWFSFIDCUJDSN-UHFFFAOYSA-N C(C)[N+]1(C(CC(CC1)C)C)C Chemical compound C(C)[N+]1(C(CC(CC1)C)C)C SEWFSFIDCUJDSN-UHFFFAOYSA-N 0.000 description 2
- YPAUHXIEJRHJEN-UHFFFAOYSA-N C(C)[N+]1(CC(C(CC1)C)C)C Chemical compound C(C)[N+]1(CC(C(CC1)C)C)C YPAUHXIEJRHJEN-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 230000005518 electrochemistry Effects 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- CHENNSUMXBIICM-UHFFFAOYSA-N 1,1,2,2,3,5-hexamethylpyrrolidin-1-ium Chemical compound C[N+]1(C(C(CC1C)C)(C)C)C CHENNSUMXBIICM-UHFFFAOYSA-N 0.000 description 1
- NQJUTRNFTKVMBA-UHFFFAOYSA-N 1,1,2,2,3-pentamethylpyrrolidin-1-ium Chemical compound CC1C([N+](CC1)(C)C)(C)C NQJUTRNFTKVMBA-UHFFFAOYSA-N 0.000 description 1
- FYJQLZLKXZUZQY-UHFFFAOYSA-N 1,1,2,2,4,4-hexamethylpyrrolidin-1-ium Chemical compound C[N+]1(C(CC(C1)(C)C)(C)C)C FYJQLZLKXZUZQY-UHFFFAOYSA-N 0.000 description 1
- YATZZJIFNYWEBL-UHFFFAOYSA-N 1,1,2,2,4,5-hexamethylpyrrolidin-1-ium Chemical compound C[N+]1(C(CC(C1C)C)(C)C)C YATZZJIFNYWEBL-UHFFFAOYSA-N 0.000 description 1
- LSTFYGDNJGVQHS-UHFFFAOYSA-N 1,1,2,2,4-pentamethylpyrrolidin-1-ium Chemical compound C[N+]1(C(CC(C1)C)(C)C)C LSTFYGDNJGVQHS-UHFFFAOYSA-N 0.000 description 1
- KCHGTHILQIOGAR-UHFFFAOYSA-N 1,1,2,2,5,5-hexamethylpyrrolidin-1-ium Chemical compound C[N+]1(C(CCC1(C)C)(C)C)C KCHGTHILQIOGAR-UHFFFAOYSA-N 0.000 description 1
- PUADPAGVJJQAIZ-UHFFFAOYSA-N 1,1,2,2,5-pentamethylpyrrolidin-1-ium Chemical compound C[N+]1(C(CCC1C)(C)C)C PUADPAGVJJQAIZ-UHFFFAOYSA-N 0.000 description 1
- ZYJWHRQTNJMEQE-UHFFFAOYSA-N 1,1,2,2-tetramethylpyrrolidin-1-ium Chemical compound CC1(C)CCC[N+]1(C)C ZYJWHRQTNJMEQE-UHFFFAOYSA-N 0.000 description 1
- XBVDKQSRITWTJV-UHFFFAOYSA-N 1,1,2,3,3,4-hexamethylpyrrolidin-1-ium Chemical compound C[N+]1(C(C(C(C1)C)(C)C)C)C XBVDKQSRITWTJV-UHFFFAOYSA-N 0.000 description 1
- UVPGUVUWQWPRLE-UHFFFAOYSA-N 1,1,2,3,3,5-hexamethylpyrrolidin-1-ium Chemical compound C[N+]1(C(C(CC1C)(C)C)C)C UVPGUVUWQWPRLE-UHFFFAOYSA-N 0.000 description 1
- KWIKFSVBAUIXOB-UHFFFAOYSA-N 1,1,2,3,4,4-hexamethylpyrrolidin-1-ium Chemical compound C[N+]1(C(C(C(C1)(C)C)C)C)C KWIKFSVBAUIXOB-UHFFFAOYSA-N 0.000 description 1
- ZZBJRABHCMMTHR-UHFFFAOYSA-N 1,1,2,3,4,5-hexamethylpyrrolidin-1-ium Chemical compound CC1C(C)C(C)[N+](C)(C)C1C ZZBJRABHCMMTHR-UHFFFAOYSA-N 0.000 description 1
- QNPUOWNVFGPKOW-UHFFFAOYSA-N 1,1,2,3,4-pentamethylpyrrolidin-1-ium Chemical compound C[N+]1(C(C(C(C1)C)C)C)C QNPUOWNVFGPKOW-UHFFFAOYSA-N 0.000 description 1
- ATXJIWLRRMLBNH-UHFFFAOYSA-N 1,1,2,3,5-pentamethylpyrrolidin-1-ium Chemical compound C[N+]1(C(C(CC1C)C)C)C ATXJIWLRRMLBNH-UHFFFAOYSA-N 0.000 description 1
- ITHSFYRZIAVQRQ-UHFFFAOYSA-N 1,1,2,3-tetraethylpiperidin-1-ium Chemical compound C(C)[N+]1(C(C(CCC1)CC)CC)CC ITHSFYRZIAVQRQ-UHFFFAOYSA-N 0.000 description 1
- ROTAKHWWFFOZRT-UHFFFAOYSA-N 1,1,2,3-tetramethylpiperidin-1-ium Chemical compound CC1CCC[N+](C)(C)C1C ROTAKHWWFFOZRT-UHFFFAOYSA-N 0.000 description 1
- FLMMWKJWBYPWDM-UHFFFAOYSA-N 1,1,2,4,4-pentamethylpyrrolidin-1-ium Chemical compound C[N+]1(CC(CC1C)(C)C)C FLMMWKJWBYPWDM-UHFFFAOYSA-N 0.000 description 1
- LJIFXDGSARIZOB-UHFFFAOYSA-N 1,1,2,4-tetraethylpiperidin-1-ium Chemical compound C(C)[N+]1(C(CC(CC1)CC)CC)CC LJIFXDGSARIZOB-UHFFFAOYSA-N 0.000 description 1
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- UEFMJTMXNZAYBP-UHFFFAOYSA-N 1,1,2,5-tetraethylpiperidin-1-ium Chemical compound C(C)[N+]1(C(CCC(C1)CC)CC)CC UEFMJTMXNZAYBP-UHFFFAOYSA-N 0.000 description 1
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- QKKHGXDKYQKZKJ-UHFFFAOYSA-N 1,1,2,6-tetraethylpiperidin-1-ium Chemical compound C(C)[N+]1(C(CCCC1CC)CC)CC QKKHGXDKYQKZKJ-UHFFFAOYSA-N 0.000 description 1
- ZYOMXQGIWAKIBK-UHFFFAOYSA-N 1,1,2,6-tetramethylpiperidin-1-ium Chemical compound CC1CCCC(C)[N+]1(C)C ZYOMXQGIWAKIBK-UHFFFAOYSA-N 0.000 description 1
- YPYPYRNEQAUXHU-UHFFFAOYSA-N 1,1,2-triethyl-3-methylpiperidin-1-ium Chemical compound C(C)[N+]1(C(C(CCC1)C)CC)CC YPYPYRNEQAUXHU-UHFFFAOYSA-N 0.000 description 1
- PDPPMLGMILGNKD-UHFFFAOYSA-N 1,1,2-triethyl-4-methylpiperidin-1-ium Chemical compound C(C)[N+]1(C(CC(CC1)C)CC)CC PDPPMLGMILGNKD-UHFFFAOYSA-N 0.000 description 1
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- KFOJGNZTVDAFEW-UHFFFAOYSA-N diethyl-methyl-propan-2-ylazanium Chemical compound CC[N+](C)(CC)C(C)C KFOJGNZTVDAFEW-UHFFFAOYSA-N 0.000 description 1
- FXBZEWFIRVLRJG-UHFFFAOYSA-N diethyl-methyl-propan-2-ylphosphanium Chemical compound CC[P+](C)(CC)C(C)C FXBZEWFIRVLRJG-UHFFFAOYSA-N 0.000 description 1
- KSRKBDUROZKZBR-UHFFFAOYSA-N diethyl-methyl-propylazanium Chemical compound CCC[N+](C)(CC)CC KSRKBDUROZKZBR-UHFFFAOYSA-N 0.000 description 1
- VJGBCPDZKYOXCS-UHFFFAOYSA-N diethyl-methyl-propylphosphanium Chemical compound CCC[P+](C)(CC)CC VJGBCPDZKYOXCS-UHFFFAOYSA-N 0.000 description 1
- FIWKZGLQMIABFH-UHFFFAOYSA-N diethyl-propan-2-yl-propylazanium Chemical compound CCC[N+](CC)(CC)C(C)C FIWKZGLQMIABFH-UHFFFAOYSA-N 0.000 description 1
- WQHRRUZRGXLCGL-UHFFFAOYSA-N dimethyl(dipropyl)azanium Chemical compound CCC[N+](C)(C)CCC WQHRRUZRGXLCGL-UHFFFAOYSA-N 0.000 description 1
- UUWXBQMAEMOZSL-UHFFFAOYSA-N dimethyl(dipropyl)phosphanium Chemical compound CCC[P+](C)(C)CCC UUWXBQMAEMOZSL-UHFFFAOYSA-N 0.000 description 1
- GJZAMOYERKVOGF-UHFFFAOYSA-N dimethyl-di(propan-2-yl)azanium Chemical compound CC(C)[N+](C)(C)C(C)C GJZAMOYERKVOGF-UHFFFAOYSA-N 0.000 description 1
- UEQUYJNKYDGLDX-UHFFFAOYSA-N dimethyl-di(propan-2-yl)phosphanium Chemical compound CC(C)[P+](C)(C)C(C)C UEQUYJNKYDGLDX-UHFFFAOYSA-N 0.000 description 1
- IIVJLLCOQHTMSX-UHFFFAOYSA-N dimethyl-propan-2-yl-propylazanium Chemical compound CCC[N+](C)(C)C(C)C IIVJLLCOQHTMSX-UHFFFAOYSA-N 0.000 description 1
- ABVKLRTZGOJHSA-UHFFFAOYSA-N dimethyl-propan-2-yl-propylphosphanium Chemical compound CCC[P+](C)(C)C(C)C ABVKLRTZGOJHSA-UHFFFAOYSA-N 0.000 description 1
- FJDXVRSRCARKHN-UHFFFAOYSA-N ditert-butyl(dimethyl)azanium Chemical compound CC(C)(C)[N+](C)(C)C(C)(C)C FJDXVRSRCARKHN-UHFFFAOYSA-N 0.000 description 1
- HYZTVBHHERXKDB-UHFFFAOYSA-N ditert-butyl(dimethyl)phosphanium Chemical compound CC(C)(C)[P+](C)(C)C(C)(C)C HYZTVBHHERXKDB-UHFFFAOYSA-N 0.000 description 1
- IQLVJVXTKNBZRC-UHFFFAOYSA-N ethyl(trimethyl)phosphanium Chemical compound CC[P+](C)(C)C IQLVJVXTKNBZRC-UHFFFAOYSA-N 0.000 description 1
- TUFNCRWGQFDPIE-UHFFFAOYSA-N ethyl-dimethyl-(2-methylpropyl)azanium Chemical compound CC[N+](C)(C)CC(C)C TUFNCRWGQFDPIE-UHFFFAOYSA-N 0.000 description 1
- MJYZGTNKJORSFC-UHFFFAOYSA-N ethyl-dimethyl-(2-methylpropyl)phosphanium Chemical compound CC[P+](C)(C)CC(C)C MJYZGTNKJORSFC-UHFFFAOYSA-N 0.000 description 1
- JNHMTDWODKLBSI-UHFFFAOYSA-N ethyl-dimethyl-propan-2-ylazanium Chemical compound CC[N+](C)(C)C(C)C JNHMTDWODKLBSI-UHFFFAOYSA-N 0.000 description 1
- HNDVNTJHZVRTFN-UHFFFAOYSA-N ethyl-dimethyl-propan-2-ylphosphanium Chemical compound CC[P+](C)(C)C(C)C HNDVNTJHZVRTFN-UHFFFAOYSA-N 0.000 description 1
- ZOZZQPFBMNNPPO-UHFFFAOYSA-N ethyl-dimethyl-propylazanium Chemical compound CCC[N+](C)(C)CC ZOZZQPFBMNNPPO-UHFFFAOYSA-N 0.000 description 1
- XRUDAGYWANYZNW-UHFFFAOYSA-N ethyl-dimethyl-propylphosphanium Chemical compound CCC[P+](C)(C)CC XRUDAGYWANYZNW-UHFFFAOYSA-N 0.000 description 1
- BCUPRSGLHYWGKH-UHFFFAOYSA-N ethyl-methyl-di(propan-2-yl)azanium Chemical compound CC[N+](C)(C(C)C)C(C)C BCUPRSGLHYWGKH-UHFFFAOYSA-N 0.000 description 1
- BKOXNSXLTVCOOX-UHFFFAOYSA-N ethyl-methyl-di(propan-2-yl)phosphanium Chemical compound CC[P+](C)(C(C)C)C(C)C BKOXNSXLTVCOOX-UHFFFAOYSA-N 0.000 description 1
- YZCTWRWJKAZUIJ-UHFFFAOYSA-N ethyl-methyl-dipropylazanium Chemical compound CCC[N+](C)(CC)CCC YZCTWRWJKAZUIJ-UHFFFAOYSA-N 0.000 description 1
- YAGMCBIUTUVNRS-UHFFFAOYSA-N ethyl-methyl-dipropylphosphanium Chemical compound CCC[P+](C)(CC)CCC YAGMCBIUTUVNRS-UHFFFAOYSA-N 0.000 description 1
- MGKSZJZWMLUTKO-UHFFFAOYSA-N ethyl-methyl-propan-2-yl-propylazanium Chemical compound CCC[N+](C)(CC)C(C)C MGKSZJZWMLUTKO-UHFFFAOYSA-N 0.000 description 1
- RXSLKEICXDUFAS-UHFFFAOYSA-N ethyl-methyl-propan-2-yl-propylphosphanium Chemical compound CCC[P+](C)(CC)C(C)C RXSLKEICXDUFAS-UHFFFAOYSA-N 0.000 description 1
- YOMFVLRTMZWACQ-UHFFFAOYSA-N ethyltrimethylammonium Chemical compound CC[N+](C)(C)C YOMFVLRTMZWACQ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- NNCAWEWCFVZOGF-UHFFFAOYSA-N mepiquat Chemical compound C[N+]1(C)CCCCC1 NNCAWEWCFVZOGF-UHFFFAOYSA-N 0.000 description 1
- VFOJFWOVDZGATC-UHFFFAOYSA-N methyl(tripropyl)azanium Chemical compound CCC[N+](C)(CCC)CCC VFOJFWOVDZGATC-UHFFFAOYSA-N 0.000 description 1
- PLNPRGLZZXAKGE-UHFFFAOYSA-N methyl(tripropyl)phosphanium Chemical compound CCC[P+](C)(CCC)CCC PLNPRGLZZXAKGE-UHFFFAOYSA-N 0.000 description 1
- FKXJNJOXPFTFGS-UHFFFAOYSA-N methyl-bis(2-methylpropyl)phosphane Chemical compound CC(C)CP(C)CC(C)C FKXJNJOXPFTFGS-UHFFFAOYSA-N 0.000 description 1
- COYQOLYIVUYLFQ-UHFFFAOYSA-N methyl-di(propan-2-yl)-propylazanium Chemical compound CCC[N+](C)(C(C)C)C(C)C COYQOLYIVUYLFQ-UHFFFAOYSA-N 0.000 description 1
- UOYRNUKOGDYMHL-UHFFFAOYSA-N methyl-di(propan-2-yl)-propylphosphanium Chemical compound CCC[P+](C)(C(C)C)C(C)C UOYRNUKOGDYMHL-UHFFFAOYSA-N 0.000 description 1
- CNALFBRJGWDPSA-UHFFFAOYSA-N methyl-propan-2-yl-dipropylazanium Chemical compound CCC[N+](C)(C(C)C)CCC CNALFBRJGWDPSA-UHFFFAOYSA-N 0.000 description 1
- LDNQTHUGZRBINL-UHFFFAOYSA-N methyl-propan-2-yl-dipropylphosphanium Chemical compound CCC[P+](C)(C(C)C)CCC LDNQTHUGZRBINL-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 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
- ISRZMEWDKIVXMZ-UHFFFAOYSA-N tert-butyl(triethyl)phosphanium Chemical compound CC[P+](CC)(CC)C(C)(C)C ISRZMEWDKIVXMZ-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
- JURMQHJOLRNTFQ-UHFFFAOYSA-N tert-butyl(trimethyl)phosphanium Chemical compound CC(C)(C)[P+](C)(C)C JURMQHJOLRNTFQ-UHFFFAOYSA-N 0.000 description 1
- FHELAZMFNUMSEI-UHFFFAOYSA-N tert-butyl-dimethyl-(2-methylpropyl)azanium Chemical compound CC(C)C[N+](C)(C)C(C)(C)C FHELAZMFNUMSEI-UHFFFAOYSA-N 0.000 description 1
- ZRGJBCFDFPJHQY-UHFFFAOYSA-N tert-butyl-dimethyl-(2-methylpropyl)phosphanium Chemical compound CC(C)C[P+](C)(C)C(C)(C)C ZRGJBCFDFPJHQY-UHFFFAOYSA-N 0.000 description 1
- XMPRLBUMOCTEHU-UHFFFAOYSA-N tert-butyl-ethyl-dimethylazanium Chemical compound CC[N+](C)(C)C(C)(C)C XMPRLBUMOCTEHU-UHFFFAOYSA-N 0.000 description 1
- QRBXDQYQCKMHAQ-UHFFFAOYSA-N tert-butyl-ethyl-dimethylphosphanium Chemical compound CC[P+](C)(C)C(C)(C)C QRBXDQYQCKMHAQ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- SZWHXXNVLACKBV-UHFFFAOYSA-N tetraethylphosphanium Chemical compound CC[P+](CC)(CC)CC SZWHXXNVLACKBV-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- BXYHVFRRNNWPMB-UHFFFAOYSA-N tetramethylphosphanium Chemical compound C[P+](C)(C)C BXYHVFRRNNWPMB-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine 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
- BPGMZCWNCLPGCP-UHFFFAOYSA-N triethyl(2-methylpropyl)phosphanium Chemical compound CC[P+](CC)(CC)CC(C)C BPGMZCWNCLPGCP-UHFFFAOYSA-N 0.000 description 1
- SEACXNRNJAXIBM-UHFFFAOYSA-N triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC SEACXNRNJAXIBM-UHFFFAOYSA-N 0.000 description 1
- TZWFFXFQARPFJN-UHFFFAOYSA-N triethyl(methyl)phosphanium Chemical compound CC[P+](C)(CC)CC TZWFFXFQARPFJN-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
- PGFKTVMMTHIEKT-UHFFFAOYSA-N triethyl(propyl)phosphanium Chemical compound CCC[P+](CC)(CC)CC PGFKTVMMTHIEKT-UHFFFAOYSA-N 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
- FUTFRQAXSYLPPW-UHFFFAOYSA-N trimethyl(2-methylpropyl)phosphanium Chemical compound CC(C)C[P+](C)(C)C FUTFRQAXSYLPPW-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
- QMKRJORUUNAPBZ-UHFFFAOYSA-N trimethyl(propan-2-yl)phosphanium Chemical compound CC(C)[P+](C)(C)C QMKRJORUUNAPBZ-UHFFFAOYSA-N 0.000 description 1
- YGDBTMJEJNVHPZ-UHFFFAOYSA-N trimethyl(propyl)phosphanium Chemical compound CCC[P+](C)(C)C YGDBTMJEJNVHPZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Electric Double-Layer Capacitors Or The Like (AREA)
Abstract
Description
本発明は、電気二重層コンデンサに用いられるフッ素を含む化合物を電解質とする非水電解液の製造方法に関する。さらに詳細には、非水電解液中に不純物として含まれているフッ化水素を極微量に低減させた電気二重層コンデンサ用非水電解液の製造方法に関する。 The present invention relates to a method for producing a non-aqueous electrolyte using a fluorine-containing compound used for an electric double layer capacitor as an electrolyte. More specifically, the present invention relates to a method for producing a non-aqueous electrolyte solution for an electric double layer capacitor in which hydrogen fluoride contained as an impurity in the non-aqueous electrolyte solution is reduced to a very small amount.
非水電解液を用いる電気二重層コンデンサは、耐電圧を高くできるため、水性電解液を用いる電気二重層コンデンサよりエネルギー密度を高くできる特徴がある。特に近年、注目を集めている50F以上の静電容量を有するパワー用途の電気二重層コンデンサには、非水電解液を使用したものが適している。 Since an electric double layer capacitor using a non-aqueous electrolyte can have a high withstand voltage, the electric double layer capacitor using an aqueous electrolyte has a feature that the energy density can be increased. In particular, for electric double layer capacitors for power use having a capacitance of 50 F or more, which has been attracting attention in recent years, those using a non-aqueous electrolyte are suitable.
電気二重層コンデンサに用いる非水電解液としては、従来、ホウフッ化第四級アンモニウム塩をプロピレンカーボネート等に溶解させたもの(棚橋ら、電気化学、56巻、892頁、1988年)、ホウフッ化第四級ホスホニウム塩をプロピレンカーボネート等に溶解させたもの(平塚ら、電気化学、59巻、209頁、1991年)、非対称型第4級アンモニウム塩を用いたもの(特公平3−58526号公報)、非対称型第4級アンモニウム塩とピリジニウム塩を有機溶媒に溶解させたもの(特公平2−57694号公報)等が知られている。 As the non-aqueous electrolyte used for the electric double layer capacitor, conventionally, a quaternary ammonium borofluoride salt dissolved in propylene carbonate or the like (Tanahashi et al., Electrochemistry, 56, 892, 1988), borofluoride. A solution in which a quaternary phosphonium salt is dissolved in propylene carbonate or the like (Hiratsuka et al., Electrochemistry, 59, 209, 1991), an asymmetric quaternary ammonium salt (Japanese Patent Publication No. 3-58526) ), An asymmetric quaternary ammonium salt and a pyridinium salt dissolved in an organic solvent (Japanese Patent Publication No. 2-57694) are known.
しかし、これらの非水電解液を使用した電気二重層コンデンサは、長期信頼性に欠けるという問題がある。
本発明者らの検討によれば、この原因は電解液中にフッ化水素が存在していることによる。すなわち電解質として用いられるホウフッ化第4級アンモニウム塩やホウフッ化第4級ホスホニウム塩などは、通常は不純物として微量のフッ化水素を含んでいるので、これらの第4級アンモニウム塩や第4級ホウホニウム塩などを非水溶媒に溶解してなる電解液には、当然のことながらフッ化水素が含まれることになる。また、これらの第4級アンモニウム塩や第4級ホスホニウム塩に含まれている不純物が、非水溶媒中の微量の水と反応してフッ化水素を発生させることもある。
However, electric double layer capacitors using these non-aqueous electrolytes have a problem of lacking long-term reliability.
According to the study by the present inventors, this cause is due to the presence of hydrogen fluoride in the electrolyte. That is, borofluorinated quaternary ammonium salts and borofluorinated quaternary phosphonium salts used as electrolytes usually contain a trace amount of hydrogen fluoride as an impurity. Therefore, these quaternary ammonium salts and quaternary borophonium salts are used. As a matter of course, hydrogen fluoride is contained in an electrolytic solution obtained by dissolving a salt or the like in a non-aqueous solvent. Further, impurities contained in these quaternary ammonium salts and quaternary phosphonium salts may react with a small amount of water in a non-aqueous solvent to generate hydrogen fluoride.
非水電解液中のフッ化水素は微量であるが、長期間のうちには電解液そのものを劣化させて内部抵抗を増大させたり、電気二重層コンデンサの電極の集電体や金属ケースの内面を腐食させたりする。電解液中のフッ化水素により引起されるこれらの障害が、従来の非水電解液を用いる電気二重層コンデンサの長期信頼性を乏しいものとしていた主な原因の一つである。従って本発明は、長期信頼性を有する電気二重層コンデンサを与える非水電解液を提供しようとするものである。 The amount of hydrogen fluoride in the non-aqueous electrolyte is very small, but over a long period of time, the electrolyte itself deteriorates to increase the internal resistance, or the current collector of the electrode of the electric double layer capacitor and the inner surface of the metal case May corrode. These obstacles caused by hydrogen fluoride in the electrolytic solution are one of the main causes that have made the long-term reliability of electric double layer capacitors using conventional nonaqueous electrolytic solutions poor. Accordingly, the present invention seeks to provide a non-aqueous electrolyte that provides an electric double layer capacitor having long-term reliability.
本発明に係る電気二重層コンデンサ用非水電解液は、非水溶媒にフッ素を含む化合物が電解質として溶解しており、かつフッ化水素の含有量が30ppm以下であることを特徴とするものである。 The non-aqueous electrolyte for electric double layer capacitors according to the present invention is characterized in that a compound containing fluorine is dissolved as an electrolyte in a non-aqueous solvent, and the content of hydrogen fluoride is 30 ppm or less. is there.
以下、本発明を詳細に説明する。
本発明に係る非水電解液中のフッ化水素の含有量は30ppm以下である必要がある。30ppmを越えるフッ化水素が含まれている場合には、これを用いて製造した電気二重層コンデンサの金属部分を腐食させて容量劣化を起こしたり、内部抵抗を上昇させたりするなどの問題を起こす。非水電解液中のフッ化水素の含有量は20ppm以下、特に10ppm以下であるのが好ましい。フッ化水素の含有量をこのような微量に低減させた電解液を製造するには、例えば、予め再結晶などにより充分に高純度化した実質的に無水のフッ素を含む化合物を高純度非水溶媒に溶解させる方法、フッ素を含む化合物を非水溶媒に溶解させて得た非水溶液を減圧下で加熱して、含有されている微量の水及びフッ化水素を蒸発させて除去する方法、非水溶媒にフッ素を含む化合物を溶解させて得た非水溶液を活性アルミナなどの吸着剤で吸着処理してフッ化水素を吸着除去する方法などが挙げられる。なかでも吸着処理する方法は操作が容易なので好ましい。吸着処理によりフッ化水素の含有量をどこまで低減させ得るかは、用いる吸着剤に依存する。例えば活性アルミナを硝酸の希薄水溶液などで洗浄したのち十分に水洗して乾燥したものを用いると、フッ化水素の含有量を数ppmにまで容易に低減させることができる。
本発明ではフッ素を含む化合物を電解質として用いる。通常は一般式(I)で表される第4級アンモニウム塩又は第4級ホスホニウム塩を用いる。
Hereinafter, the present invention will be described in detail.
The content of hydrogen fluoride in the nonaqueous electrolytic solution according to the present invention needs to be 30 ppm or less. When hydrogen fluoride exceeding 30 ppm is contained, the metal part of the electric double layer capacitor manufactured using this corrodes and causes problems such as capacity deterioration and increase in internal resistance. . The content of hydrogen fluoride in the non-aqueous electrolyte is preferably 20 ppm or less, particularly preferably 10 ppm or less. In order to produce an electrolytic solution in which the content of hydrogen fluoride is reduced to such a minute amount, for example, a compound containing substantially anhydrous fluorine that has been sufficiently purified in advance by recrystallization or the like is used as a high-purity nonaqueous solution. A method of dissolving in a solvent, a method of removing a trace amount of water and hydrogen fluoride by removing a non-aqueous solution obtained by dissolving a compound containing fluorine in a non-aqueous solvent under reduced pressure, Examples include a method of adsorbing and removing hydrogen fluoride by adsorbing a non-aqueous solution obtained by dissolving a fluorine-containing compound in an aqueous solvent with an adsorbent such as activated alumina. Among these, the adsorption treatment method is preferable because it is easy to operate. The extent to which the content of hydrogen fluoride can be reduced by the adsorption treatment depends on the adsorbent used. For example, when activated alumina is washed with a dilute aqueous solution of nitric acid and then sufficiently washed with water and dried, the content of hydrogen fluoride can be easily reduced to several ppm.
In the present invention, a fluorine-containing compound is used as the electrolyte. Usually, a quaternary ammonium salt or a quaternary phosphonium salt represented by the general formula (I) is used.
(化2)
Q+X− …(I)
(Chemical formula 2)
Q + X − (I)
(式中、Q+は第4級アンモニウム基又は第4級ホスホニウム基であり、X−はPF6 −、BF4 −、AsF6 −、N(CF3SO3)2 −、C(CF3SO3)3 −、SbF6 −及びRfSO3 −(Rfは炭素数1〜8のフルオロアルキル基)よりなる群から選ばれた対イオンである。Q+で表される第4級アンモニウム基としては、任意の3級アミンをアルキル基、シクロアルキル基、アリール基、アラルキル基などで4級化したものが用いられる。第4級アンモニウム基を形成する炭化水素部分には、水酸基、アミノ基、ニトロ基、シアノ基、カルボキシル基、エーテル基、アルデヒド基などが結合していてもよい。
第4級アンモニウム基の主なものを以下に示す。
(In the formula, Q + is a quaternary ammonium group or a quaternary phosphonium group, X − is PF 6 − , BF 4 − , AsF 6 − , N (CF 3 SO 3 ) 2 − , C (CF 3 SO 3 ) 3 − , SbF 6 — and RfSO 3 — (Rf is a fluoroalkyl group having 1 to 8 carbon atoms) is a counter ion selected as a quaternary ammonium group represented by Q + Are used in which any tertiary amine is quaternized with an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, etc. The hydrocarbon moiety forming the quaternary ammonium group includes a hydroxyl group, an amino group, A nitro group, a cyano group, a carboxyl group, an ether group, an aldehyde group, or the like may be bonded.
The main quaternary ammonium groups are shown below.
トリアルキルアミンの窒素が4級化されたもの;
テトラメチルアンモニウム、エチルトリメチルアンモニウム、ジエチルジメチルアンモニウム、トリエチルメチルアンモニウム、テトラエチルアンモニウム、トリメチル−n−プロピルアンモニウム、トリメチルイソプロピルアンモニウム、エチルジメチル−n−プロピルアンモニウム、エチルジメチルイソプロピルアンモニウム、ジエチルメチル−n−プロピルアンモニウム、ジエチルメチルイソプロピルアンモニウム、ジメチルジ−n−プロピルアンモニウム、ジメチル−n−プロピルイソプロピルアンモニウム、ジメチルジイソプロピルアンモニウム、トリエチル−n−プロピルアンモニウム、n−ブチルトリメチルアンモニウム、イソブチルトリメチルアンモニウム、t−ブチルトリメチルアンモニウム、トリエチルイソプロピルアンモニウム、エチルメチルジ−n−プロピルアンモニウム、エチルメチル−n−プロピルイソプロピルアンモニウム、エチルメチルジイソプロピルアンモニウム、n−ブチルエチルジメチルアンモニウム、イソブチルエチルジメチルアンモニウム、t−ブチルエチルジメチルアンモニウム、ジエチルジ−n−プロピルアンモニウム、ジエチル−n−プロピルイソプロピルアンモニウム、ジエチルジイソプロピルアンモニウム、メチルトリ−n−プロピルアンモニウム、メチルジ−n−プロピルイソプロピルアンモニウム、メチル−n−プロピルジイソプロピルアンモニウム、n−ブチルトリエチルアンモニウム、イソブチルトリエチルアンモニウム、t−ブチルトリエチルアンモニウム、ジ−n−ブチルジメチルアンモニウム、ジイソブチルジメチルアンモニウム、ジ−t−ブチルジメチルアンモニウム、n−ブチルイソブチルジメチルアンモニウム、n−ブチル−t−ブチルジメチルアンモニウム、イソブチル−t−ブチルジメチルアンモニウムなど。
Quaternized trialkylamine nitrogen;
Tetramethylammonium, ethyltrimethylammonium, diethyldimethylammonium, triethylmethylammonium, tetraethylammonium, trimethyl-n-propylammonium, trimethylisopropylammonium, ethyldimethyl-n-propylammonium, ethyldimethylisopropylammonium, diethylmethyl-n-propylammonium , Diethylmethylisopropylammonium, dimethyldi-n-propylammonium, dimethyl-n-propylisopropylammonium, dimethyldiisopropylammonium, triethyl-n-propylammonium, n-butyltrimethylammonium, isobutyltrimethylammonium, t-butyltrimethylammonium, triethylisopropyl A Monium, ethylmethyldi-n-propylammonium, ethylmethyl-n-propylisopropylammonium, ethylmethyldiisopropylammonium, n-butylethyldimethylammonium, isobutylethyldimethylammonium, t-butylethyldimethylammonium, diethyldi-n-propylammonium, diethyl -N-propylisopropylammonium, diethyldiisopropylammonium, methyltri-n-propylammonium, methyldi-n-propylisopropylammonium, methyl-n-propyldiisopropylammonium, n-butyltriethylammonium, isobutyltriethylammonium, t-butyltriethylammonium, Di-n-butyldimethylammonium, diisobutyl Ammonium, di -t- butyl dimethyl ammonium, n- butyl isobutyl dimethyl ammonium, n- butyl -t- butyl dimethyl ammonium, isobutyl -t- butyl dimethyl ammonium.
ピロリジン環の窒素が4級化されたもの;
N,N−ジメチルピロリジニウム、N−エチル−N−メチルピロリジニウム、N,N−ジエチルピロリジニウム、1,1,2−トリメチルピロリジニウム、1,1,3−トリメチルピロリジニウム、1−エチル−1,2−ジメチルピロリジニウム、1−エチル−1,3−ジメチルピロリジニウム、2−エチル−1,1−ジメチルピロリジニウム、3−エチル−1,1−ジメチルピロリジニウム、1,1−ジエチル−2−メチルピロリジニウム、1,1−ジエチル−3−メチルピロリジニウム、1,2−ジエチル−1−メチルピロリジニウム、1,3−ジエチル−1−メチルピロリジニウム、1,1,2−トリエチルピロリジニウム、1,1,3−トリエチルピロリジニウム、1,1,2,2−テトラメチルピロリジニウム、1,1,2,3−テトラメチルピロリジニウム、1,1,2,4−テトラメチルピロリジニウム、1,1,2,5−テトラメチルピロリジニウム、1,1,3,4−テトラメチルピロリジニウム、1,1,3,3−テトラメチルピロリジニウム、2−エチル−1,1,2−トリメチルピロリジニウム、2−エチル−1,1,3−トリメチルピロリジニウム、3−エチル−1,1,2−トリメチルピロリジニウム、3−エチル−1,1,3−トリメチルピロリジニウム、2−エチル−1,1,4−トリメチルピロリジニウム、4−エチル−1,1,2−トリメチルピロリジニウム、2−エチル−1,1,5−トリメチルピロリジニウム、3−エチル−1,1,4−トリメチルピロリジニウム、1−エチル−1,2,2−トリメチルピロリジニウム、1−エチル−1,2,3−トリメチルピロリジニウム、1−エチル−1,3,3−トリメチルピロリジニウム、1−エチル−1,2,4−トリメチルピロリジニウム、1−エチル−1,2,5−トリメチルピロリジニウム、1−エチル−1,3,4−トリメチルピロリジニウム、2,2−ジエチル−1,1−ジメチルピロリジニウム、2,3−ジエチル−1,1−ジメチルピロリジニウム、3,3−ジエチル−1,1−ジメチルピロリジニウム、2,4−ジエチル−1,1−ジメチルピロリジニウム、2,5−ジエチル−1,1−ジメチルピロリジニウム、3,4−ジエチル−1,1−ジメチルピロリジニウム、1,2−ジエチル−1,2−ジメチルピロリジニウム、1,2−ジエチル−1,3−ジメチルピロリジニウム、1,3−ジエチル−1,2−ジメチルピロリジニウム、1,3−ジエチル−1,3−ジメチルピロリジニウム、1,2−ジエチル−1,4−ジメチルピロリジニウム、1,4−ジエチル−1,2−ジメチルピロリジニウム、1,2−ジエチル−1,5−ジメチルピロリジニウム、1,3−ジエチル−1,4−ジメチルピロリジニウム、1,1,2,2,3−ペンタメチルピロリジニウム、1,1,2,2,4−ペンタメチルピロリジニウム、1,1,2,2,5−ペンタメチルピロリジニウム、1,1,2,3,4−ペンタメチルピロリジニウム、1,1,2,3,5−ペンタメチルピロリジニウム、1,1,3,3,4−ペンタメチルピロリジニウム、1,1,3,3,5−ペンタメチルピロリジニウム、1−エチル−1,2,2,3−テトラメチルピロリジニウム、1−エチル−1,2,2,4−テトラメチルピロリジニウム、1−エチル−1,2,2,5−テトラメチルピロリジニウム、1−エチル−1,2,3,4−テトラメチルピロリジニウム、1−エチル−1,2,3,5−テトラメチルピロリジニウム、1−エチル−1,2,4,5−テトラメチルピロリジニウム、1−エチル−1,3,3,4−テトラメチルピロリジニウム、1−エチル−1,3,3,5−テトラメチルピロリジニウム、2−エチル−1,1,2,3−テトラメチルピロリジニウム、2−エチル−1,1,2,4−テトラメチルピロリジニウム、2−エチル−1,1,2,5−テトラメチルピロリジニウム、2−エチル−1,1,3,3−テトラメチルピロリジニウム、2−エチル−1,1,3,4−テトラメチルピロリジニウム、2−エチル−1,1,3,5−テトラメチルピロリジニウム、2−エチル−1,1,4,4−テトラメチルピロリジニウム、2−エチル−1,1,4,5−テトラメチルピロリジニウム、2−エチル−1,1,5,5−テトラメチルピロリジニウム、3−エチル−1,1,2,2−テトラメチルピロリジニウム、3−エチル−1,1,2,3−テトラメチルピロリジニウム、3−エチル−1,1,2,4−テトラメチルピロリジニウム、3−エチル−1,1,2,5−テトラメチルピロリジニウム、3−エチル−1,1,3,4−テトラメチルピロリジニウム、3−エチル−1,1,4,4−テトラメチルピロリジニウム、3−エチル−1,1,4,5−テトラメチルピロリジニウム、1,1,2,2,3,3−ヘキサメチルピロリジニウム、1,1,2,2,3,4−ヘキサメチルピロリジニウム、1,1,2,2,3,5−ヘキサメチルピロリジニウム、1,1,2,2,4,4−ヘキサメチルピロリジニウム、1,1,2,2,4,5−ヘキサメチルピロリジニウム、1,1,2,2,5,5−ヘキサメチルピロリジニウム、1,1,2,3,3,4−ヘキサメチルピロリジニウム、1,1,2,3,3,5−ヘキサメチルピロリジニウム、1,1,2,3,4,4−ヘキサメチルピロリジニウム、1,1,2,3,5,5−ヘキサメチルピロリジニウム、1,1,2,3,4,5−ヘキサメチルピロリジニウムなど。
Quaternized nitrogen of the pyrrolidine ring;
N, N-dimethylpyrrolidinium, N-ethyl-N-methylpyrrolidinium, N, N-diethylpyrrolidinium, 1,1,2-trimethylpyrrolidinium, 1,1,3-trimethylpyrrolidinium 1-ethyl-1,2-dimethylpyrrolidinium, 1-ethyl-1,3-dimethylpyrrolidinium, 2-ethyl-1,1-dimethylpyrrolidinium, 3-ethyl-1,1-dimethylpyrrole Dinium, 1,1-diethyl-2-methylpyrrolidinium, 1,1-diethyl-3-methylpyrrolidinium, 1,2-diethyl-1-methylpyrrolidinium, 1,3-diethyl-1- Methylpyrrolidinium, 1,1,2-triethylpyrrolidinium, 1,1,3-triethylpyrrolidinium, 1,1,2,2-tetramethylpyrrolidinium, 1,1,2,3- Tramethylpyrrolidinium, 1,1,2,4-tetramethylpyrrolidinium, 1,1,2,5-tetramethylpyrrolidinium, 1,1,3,4-tetramethylpyrrolidinium, 1, 1,3,3-tetramethylpyrrolidinium, 2-ethyl-1,1,2-trimethylpyrrolidinium, 2-ethyl-1,1,3-trimethylpyrrolidinium, 3-ethyl-1,1, 2-trimethylpyrrolidinium, 3-ethyl-1,1,3-trimethylpyrrolidinium, 2-ethyl-1,1,4-trimethylpyrrolidinium, 4-ethyl-1,1,2-trimethylpyrrolidi Ni, 2-ethyl-1,1,5-trimethylpyrrolidinium, 3-ethyl-1,1,4-trimethylpyrrolidinium, 1-ethyl-1,2,2-trimethylpyrrolidinium, 1-ethyl − , 2,3-trimethylpyrrolidinium, 1-ethyl-1,3,3-trimethylpyrrolidinium, 1-ethyl-1,2,4-trimethylpyrrolidinium, 1-ethyl-1,2,5- Trimethylpyrrolidinium, 1-ethyl-1,3,4-trimethylpyrrolidinium, 2,2-diethyl-1,1-dimethylpyrrolidinium, 2,3-diethyl-1,1-dimethylpyrrolidinium, 3,3-diethyl-1,1-dimethylpyrrolidinium, 2,4-diethyl-1,1-dimethylpyrrolidinium, 2,5-diethyl-1,1-dimethylpyrrolidinium, 3,4-diethyl -1,1-dimethylpyrrolidinium, 1,2-diethyl-1,2-dimethylpyrrolidinium, 1,2-diethyl-1,3-dimethylpyrrolidinium, 1,3-diethyl-1,2- Jime Tilpyrrolidinium, 1,3-diethyl-1,3-dimethylpyrrolidinium, 1,2-diethyl-1,4-dimethylpyrrolidinium, 1,4-diethyl-1,2-dimethylpyrrolidinium, 1,2-diethyl-1,5-dimethylpyrrolidinium, 1,3-diethyl-1,4-dimethylpyrrolidinium, 1,1,2,2,3-pentamethylpyrrolidinium, 1,1, 2,2,4-pentamethylpyrrolidinium, 1,1,2,2,5-pentamethylpyrrolidinium, 1,1,2,3,4-pentamethylpyrrolidinium, 1,1,2, 3,5-pentamethylpyrrolidinium, 1,1,3,3,4-pentamethylpyrrolidinium, 1,1,3,3,5-pentamethylpyrrolidinium, 1-ethyl-1,2, 2,3-tetramethylpyrrolidinium, 1- Til-1,2,2,4-tetramethylpyrrolidinium, 1-ethyl-1,2,2,5-tetramethylpyrrolidinium, 1-ethyl-1,2,3,4-tetramethylpyrrolidinium 1-ethyl-1,2,3,4-tetramethylpyrrolidinium, 1-ethyl-1,2,4,5-tetramethylpyrrolidinium, 1-ethyl-1,3,4,4- Tetramethylpyrrolidinium, 1-ethyl-1,3,3,5-tetramethylpyrrolidinium, 2-ethyl-1,1,2,3-tetramethylpyrrolidinium, 2-ethyl-1,1, 2,4-tetramethylpyrrolidinium, 2-ethyl-1,1,2,5-tetramethylpyrrolidinium, 2-ethyl-1,1,3,3-tetramethylpyrrolidinium, 2-ethyl- 1,1,3,4-tetramethylpyrrolidinium 2-ethyl-1,1,3,5-tetramethylpyrrolidinium, 2-ethyl-1,1,4,4-tetramethylpyrrolidinium, 2-ethyl-1,1,4,5-tetramethyl Pyrrolidinium, 2-ethyl-1,1,5,5-tetramethylpyrrolidinium, 3-ethyl-1,1,2,2-tetramethylpyrrolidinium, 3-ethyl-1,1,2, 3-tetramethylpyrrolidinium, 3-ethyl-1,1,2,4-tetramethylpyrrolidinium, 3-ethyl-1,1,2,5-tetramethylpyrrolidinium, 3-ethyl-1, 1,3,4-tetramethylpyrrolidinium, 3-ethyl-1,1,4,4-tetramethylpyrrolidinium, 3-ethyl-1,1,4,5-tetramethylpyrrolidinium, 1, 1,2,2,3,3-hexamethylpyrrolidinium 1,1,2,2,3,4-hexamethylpyrrolidinium, 1,1,2,2,3,5-hexamethylpyrrolidinium, 1,1,2,2,4,4-hexa Methylpyrrolidinium, 1,1,2,2,4,5-hexamethylpyrrolidinium, 1,1,2,2,5,5-hexamethylpyrrolidinium, 1,1,2,3,3 , 4-hexamethylpyrrolidinium, 1,1,2,3,3,5-hexamethylpyrrolidinium, 1,1,2,3,4,4-hexamethylpyrrolidinium, 1,1,2 3,5,5-hexamethylpyrrolidinium, 1,1,2,3,4,5-hexamethylpyrrolidinium and the like.
モルホリン環の窒素が4級化されたもの
N,N−ジメチルモルホリニウム、N−エチル−N−メチルモルホリニウム、N,N−ジエチルモルホリニウム、3,4,4−トリメチルモルホリニウム、2,4,4−トリメチルモルホリニウム、3−エチル−4,4−ジメチルモルホリニウム、2−エチル−4,4−ジメチルモルホリニウム、3,4−ジメチル−4−エチルモルホリニウム、2,4−ジメチル−4−エチルモルホリニウム、3−メチル−4,4−ジエチルモルホリニウム、2−メチル−4,4−ジエチルモルホリニウム、3,4−ジエチル−4−メチルモルホリニウム、2,4−ジエチル−4−メチルモルホリニウム、3,4,4−トリエチルモルホリニウム、2,4,4−トリエチルモルホリニウム、3,3,4,4−テトラメチルモルホリニウム、2,3,4,4−テトラメチルモルホリニウム、2,4,4,5−テトラメチルモルホリニウム、3,4,4,5−テトラメチルモルホリニウム、2,2,4,4−テトラメチルモルホリニウム、2,4,4,6−テトラメチルモルホリニウム、2,4,4−トリメチル−3−エチルモルホリニウム、2−エチル−3,4,4−トリメチルモルホリニウム、2,4,4−トリメチル−5−エチルモルホリニウム、2−エチル−4,4,5−トリメチルモルホリニウム、3−エチル−4,4,5−トリメチルモルホリニウム、2−エチル−4,4,6−トリメチルモルホリニウム、2,3−ジメチル−4,4−ジエチルモルホリニウム、2,5−ジメチル−4,4−ジエチルモルホリニウム、3,5−ジメチル−4,4−ジエチルモルホリニウム、2,6−ジメチル−4,4−ジエチルモルホリニウム、2,4−ジメチル−3,4−ジエチルモルホリニウム、2,4−ジエチル−3,4−ジメチルモルホリニウム、2,4−ジメチル−4,5−ジエチルモルホリニウム、2,4−ジエチル−4,5−ジメチルモルホリニウム、3,4−ジエチル−4,5−ジメチルモルホリニウム、2,4−ジエチル−4,6−ジメチルモルホリニウム、2,3−ジエチル−4,4−ジメチルモルホリニウム、2,5−ジエチル−4,4−ジメチルモルホリニウム、3,5−ジエチル−4,4−ジメチルモルホリニウム、2,6−ジエチル−4,4−ジメチルモルホリニウム、2,3,4,4,6−ペンタメチルモルホリニウム、2,3,4,4,5−ペンタメチルモルホリニウム、2,4,4,6−テトラメチル−3−エチルモルホリニウム、2,4,4,5−テトラメチル−3−エチルモルホリニウム、2−エチル−3,4,4,6−テトラメチルモルホリニウム、2−エチル−3,4,4,5−テトラメチルモルホリニウム、2,3,4,4,5,6−ヘキサメチルモルホリニウムなど。
The morpholine ring nitrogen quaternized N, N-dimethylmorpholinium, N-ethyl-N-methylmorpholinium, N, N-diethylmorpholinium, 3,4,4-trimethylmorpholinium 2,4,4-trimethylmorpholinium, 3-ethyl-4,4-dimethylmorpholinium, 2-ethyl-4,4-dimethylmorpholinium, 3,4-dimethyl-4-ethylmorpholinium 2,4-dimethyl-4-ethylmorpholinium, 3-methyl-4,4-diethylmorpholinium, 2-methyl-4,4-diethylmorpholinium, 3,4-diethyl-4-methylmol Folinium, 2,4-diethyl-4-methylmorpholinium, 3,4,4-triethylmorpholinium, 2,4,4-triethylmorpholinium, 3,3,4,4-tetramethyl Tilmorpholinium, 2,3,4,4-tetramethylmorpholinium, 2,4,4,5-tetramethylmorpholinium, 3,4,4,5-tetramethylmorpholinium, 2,2 , 4,4-tetramethylmorpholinium, 2,4,4,6-tetramethylmorpholinium, 2,4,4-trimethyl-3-ethylmorpholinium, 2-ethyl-3,4,4- Trimethylmorpholinium, 2,4,4-trimethyl-5-ethylmorpholinium, 2-ethyl-4,4,5-trimethylmorpholinium, 3-ethyl-4,4,5-trimethylmorpholinium, 2-ethyl-4,4,6-trimethylmorpholinium, 2,3-dimethyl-4,4-diethylmorpholinium, 2,5-dimethyl-4,4-diethylmorpholinium, 3,5-dimethyl -4,4- Ethylmorpholinium, 2,6-dimethyl-4,4-diethylmorpholinium, 2,4-dimethyl-3,4-diethylmorpholinium, 2,4-diethyl-3,4-dimethylmorpholinium, 2,4-dimethyl-4,5-diethylmorpholinium, 2,4-diethyl-4,5-dimethylmorpholinium, 3,4-diethyl-4,5-dimethylmorpholinium, 2,4-diethyl -4,6-dimethylmorpholinium, 2,3-diethyl-4,4-dimethylmorpholinium, 2,5-diethyl-4,4-dimethylmorpholinium, 3,5-diethyl-4,4- Dimethylmorpholinium, 2,6-diethyl-4,4-dimethylmorpholinium, 2,3,4,4,6-pentamethylmorpholinium, 2,3,4,4,5-pentamethylmorpholine Niu 2,4,4,6-tetramethyl-3-ethylmorpholinium, 2,4,4,5-tetramethyl-3-ethylmorpholinium, 2-ethyl-3,4,4,6-tetra Methylmorpholinium, 2-ethyl-3,4,4,5-tetramethylmorpholinium, 2,3,4,4,5,6-hexamethylmorpholinium and the like.
イミダゾリン環の窒素が4級化されたもの;
N,N′−ジメチルイミダゾリニウム、N−エチル−N′−メチルイミダゾリニウム、N,N′−ジエチルイミダゾリニウム、1,2,3−トリメチルイミダゾリニウム、1,3,4−トリメチルイミダゾリニウム、1−エチル−2,3−ジメチルイミダゾリニウム、1−エチル−3,4−ジメチルイミダゾリニウム、1−エチル−3,5−ジメチルイミダゾリニウム、2−エチル−1,3−ジメチルイミダゾリニウム、4−エチル−1,3−ジメチルイミダゾリニウム、1,2−ジエチル−3−メチルイミダゾリニウム、1,4−ジエチル−3−メチルイミダゾリニウム、1,5−ジエチル−3−メチルイミダゾリニウム、1,3−ジエチル−2−メチルイミダゾリニウム、1,3−ジエチル−4−メチルイミダゾリニウム、1,2,3−トリエチルイミダゾリニウム、1,3,4−トリエチルイミダゾリニウム、1,2,3,4−テトラメチルイミダゾリニウム、1−エチル−2,3,4−トリメチルイミダゾリニウム、1−エチル−2,3,5−トリメチルイミダゾリニウム、1−エチル−3,4,5−トリメチルイミダゾリニウム、2−エチル−1,3,4−トリメチルイミダゾリニウム、4−エチル−1,2,3−トリメチルイミダゾリニウム、1,2−ジエチル−3,4−ジメチルイミダゾリニウム、1,3−ジエチル−2,4−ジメチルイミダゾリニウム、1,4−ジエチル−2,3−ジメチルイミダゾリニウム、2,4−ジエチル−1,3−ジメチルイミダゾリニウム、4,5−ジエチル−1,3−ジメチルイミダゾリニウム、1,2,3−トリエチル−4−メチルイミダゾリニウム、1,2,4−トリエチル−3−メチルイミダゾリニウム、1,2,5−トリエチル−3−メチルイミダゾリニウム、1,3,4−トリエチル−2−メチルイミダゾリニウム、1,3,4−トリエチル−5−メチルイミダゾリニウム、1,4,5−トリエチル−3−メチルイミダゾリニウム、1,2,3,4,5−ペンタメチルイミダゾリニウムなど。
Quaternized nitrogen of the imidazoline ring;
N, N'-dimethylimidazolinium, N-ethyl-N'-methylimidazolinium, N, N'-diethylimidazolinium, 1,2,3-trimethylimidazolinium, 1,3,4-trimethyl Imidazolinium, 1-ethyl-2,3-dimethylimidazolinium, 1-ethyl-3,4-dimethylimidazolinium, 1-ethyl-3,5-dimethylimidazolinium, 2-ethyl-1,3 -Dimethylimidazolinium, 4-ethyl-1,3-dimethylimidazolinium, 1,2-diethyl-3-methylimidazolinium, 1,4-diethyl-3-methylimidazolinium, 1,5-diethyl -3-methylimidazolinium, 1,3-diethyl-2-methylimidazolinium, 1,3-diethyl-4-methylimidazolinium, 1,2,3- Liethylimidazolinium, 1,3,4-triethylimidazolinium, 1,2,3,4-tetramethylimidazolinium, 1-ethyl-2,3,4-trimethylimidazolinium, 1-ethyl- 2,3,5-trimethylimidazolinium, 1-ethyl-3,4,5-trimethylimidazolinium, 2-ethyl-1,3,4-trimethylimidazolinium, 4-ethyl-1,2,3 -Trimethylimidazolinium, 1,2-diethyl-3,4-dimethylimidazolinium, 1,3-diethyl-2,4-dimethylimidazolinium, 1,4-diethyl-2,3-dimethylimidazolinium 2,4-diethyl-1,3-dimethylimidazolinium, 4,5-diethyl-1,3-dimethylimidazolinium, 1,2,3-triethyl-4-methyl Imidazolinium, 1,2,4-triethyl-3-methylimidazolinium, 1,2,5-triethyl-3-methylimidazolinium, 1,3,4-triethyl-2-methylimidazolinium, 1 3,4-triethyl-5-methylimidazolinium, 1,4,5-triethyl-3-methylimidazolinium, 1,2,3,4,5-pentamethylimidazolinium and the like.
テトラヒドロピリミジン環の窒素が4級化されたもの
N,N′−ジメチルテトラヒドロピリミジニウム、N−エチル−N′−メチルテトラヒドロピリミジニウム、N,N′−ジエチルテトラヒドロピリミジニウム、1,2,3−トリメチルテトラヒドロピリミジニウム、1,3,4−トリメチルテトラヒドロピリミジニウム、1,3,5−トリメチルテトラヒドロピリミジニウム、1−エチル−2,3−ジメチルテトラヒドロピリミジニウム、1−エチル−3,4−ジメチルテトラヒドロピリミジニウム、1−エチル−3,5−ジメチルテトラヒドロピリミジニウム、1−エチル−3,6−ジメチルテトラヒドロピリミジニウム、2−エチル−1,3−ジメチルテトラヒドロピリミジニウム、4−エチル−1,3−ジメチルテトラヒドロピリミジニウム、5−エチル−1,3−ジメチルテトラヒドロピリミジニウム、1,2,3,4−テトラメチルテトラヒドロピリミジニウム、1,2,3,5−テトラメチルテトラヒドロピリミジニウム、1−エチル−2,3,4−トリメチルテトラヒドロピリミジニウム、1−エチル−2,3,5−トリメチルテトラヒドロピリミジニウム、1−エチル−2,3,6−トリメチルテトラヒドロピリミジニウム、2−エチル−1,3,4−トリメチルテトラヒドロピリミジニウム、2−エチル−1,3,5−トリメチルテトラヒドロピリミジニウム、4−エチル−1,2,3−トリメチルテトラヒドロピリミジニウム、4−エチル−1,3,5−トリメチルテトラヒドロピリミジニウム、4−エチル−1,3,6−トリメチルテトラヒドロピリミジニウム、5−エチル−1,2,3−トリメチルテトラヒドロピリミジニウム、5−エチル−1,3,4−トリメチルテトラヒドロピリミジニウム、1,2−ジエチル−3,4−ジメチルテトラヒドロピリミジニウム、1,2−ジエチル−3,5−ジメチルテトラヒドロピリミジニウム、1,2−ジエチル−3,6−ジメチルテトラヒドロピリミジニウム、1,3−ジエチル−2,4−ジメチルテトラヒドロピリミジニウム、1,3−ジエチル−2,5−ジメチルテトラヒドロピリミジニウム、1,4−ジエチル−2,3−ジメチルテトラヒドロピリミジニウム、1,4−ジエチル−3,5−ジメチルテトラヒドロピリミジニウム、1,4−ジエチル−3,6−ジメチルテトラヒドロピリミジニウム、1,5−ジエチル−2,3−ジメチルテトラヒドロピリミジニウム、1,5−ジエチル−3,4−ジメチルテトラヒドロピリミジニウム、1,5−ジエチル−3,6−ジメチルテトラヒドロピリミジニウム、2,4−ジエチル−1,3−ジメチルテトラヒドロピリミジニウム、2,5−ジエチル−1,3−ジメチルテトラヒドロピリミジニウム、4,5−ジエチル−1,3−ジメチルテトラヒドロピリミジニウム、4,6−ジエチル−1,3−ジメチルテトラヒドロピリミジニウム、1,2,3,4,5−ペンタメチルテトラヒドロピリミジニウム、1,2,3,4,6−ペンタメチルテトラヒドロピリミジニウム、1,2,3,4,5,6−ヘキサメチルテトラヒドロピリミジニウム、5−メチル−1,5−ジアザビシクロ[4.3.0]−5−ノネニウム、5−エチル−1,5−ジアザビシクロ[4.3.0]−5−ノネニウム、5−メチル−1,5−ジアザビシクロ[5.4.0]−5−ウンデセニウム、5−エチル−1,5−ジアザビシクロ[5.4.0]−5−ウンデセニウムなど。
Tetrahydropyrimidine ring nitrogen quaternized N, N'-dimethyltetrahydropyrimidinium, N-ethyl-N'-methyltetrahydropyrimidinium, N, N'-diethyltetrahydropyrimidinium, 1,2 , 3-trimethyltetrahydropyrimidinium, 1,3,4-trimethyltetrahydropyrimidinium, 1,3,5-trimethyltetrahydropyrimidinium, 1-ethyl-2,3-dimethyltetrahydropyrimidinium, 1-ethyl -3,4-dimethyltetrahydropyrimidinium, 1-ethyl-3,5-dimethyltetrahydropyrimidinium, 1-ethyl-3,6-dimethyltetrahydropyrimidinium, 2-ethyl-1,3-dimethyltetrahydropyrim Midinium, 4-ethyl-1,3-dimethyltetrahydropyri Midinium, 5-ethyl-1,3-dimethyltetrahydropyrimidinium, 1,2,3,4-tetramethyltetrahydropyrimidinium, 1,2,3,5-tetramethyltetrahydropyrimidinium, 1-ethyl- 2,3,4-trimethyltetrahydropyrimidinium, 1-ethyl-2,3,5-trimethyltetrahydropyrimidinium, 1-ethyl-2,3,6-trimethyltetrahydropyrimidinium, 2-ethyl-1, 3,4-trimethyltetrahydropyrimidinium, 2-ethyl-1,3,5-trimethyltetrahydropyrimidinium, 4-ethyl-1,2,3-trimethyltetrahydropyrimidinium, 4-ethyl-1,3, 5-trimethyltetrahydropyrimidinium, 4-ethyl-1,3,6-trimethyltetrahydropyrimidi 5-ethyl-1,2,3-trimethyltetrahydropyrimidinium, 5-ethyl-1,3,4-trimethyltetrahydropyrimidinium, 1,2-diethyl-3,4-dimethyltetrahydropyrimidinium, 1,2-diethyl-3,5-dimethyltetrahydropyrimidinium, 1,2-diethyl-3,6-dimethyltetrahydropyrimidinium, 1,3-diethyl-2,4-dimethyltetrahydropyrimidinium, 1, 3-diethyl-2,5-dimethyltetrahydropyrimidinium, 1,4-diethyl-2,3-dimethyltetrahydropyrimidinium, 1,4-diethyl-3,5-dimethyltetrahydropyrimidinium, 1,4- Diethyl-3,6-dimethyltetrahydropyrimidinium, 1,5-diethyl-2,3-dimethylte Lahydropyrimidinium, 1,5-diethyl-3,4-dimethyltetrahydropyrimidinium, 1,5-diethyl-3,6-dimethyltetrahydropyrimidinium, 2,4-diethyl-1,3-dimethyltetrahydro Pyrimidinium, 2,5-diethyl-1,3-dimethyltetrahydropyrimidinium, 4,5-diethyl-1,3-dimethyltetrahydropyrimidinium, 4,6-diethyl-1,3-dimethyltetrahydropyrimidi 1,2,3,4,5-pentamethyltetrahydropyrimidinium, 1,2,3,4,6-pentamethyltetrahydropyrimidinium, 1,2,3,4,5,6-hexamethyl Tetrahydropyrimidinium, 5-methyl-1,5-diazabicyclo [4.3.0] -5-nonenium, 5-ethyl-1,5- Diazabicyclo [4.3.0] -5-nonenium, 5-methyl-1,5-diazabicyclo [5.4.0] -5-undecenium, 5-ethyl-1,5-diazabicyclo [5.4.0] -5-undecenium and the like.
ピペラジン環の窒素が4級化されたもの;
N,N,N′,N′−テトラメチルピペラジニウム、N−エチル−N,N′,N′−トリメチルピペラジニウム、N,N−ジエチル−N′,N′−ジメチルピペラジニウム、N,N,N′−トリエチル−N′−メチルピペラジニウム、N,N,N′,N′−テトラエチルピペラジニウム、1,1,2,4,4−ペンタメチルピペラジニウム、1,1,3,4,4−ペンタメチルピペラジニウム、1,1,2,3,4,4−ヘキサメチルピペラジニウム、1,1,2,4,4,5−ヘキサメチルピペラジニウム、1,1,2,4,4,6−ヘキサメチルピペラジニウム、1,1,3,4,4,5−ヘキサメチルピペラジニウム、1−エチル−1,2,4,4−テトラメチルピペラジニウム、1−エチル−1,3,4,4−テトラメチルピペラジニウム、2−エチル−1,1,4,4−テトラメチルピペラジニウム、1−エチル−1,2,4,4−テトラメチルピペラジニウム、1−エチル−1,3,4,4−テトラメチルピペラジニウム、1,1−ジエチル−2,4,4−トリメチルピペラジニウム、1,4−ジエチル−1,2,4−トリメチルピペラジニウム、1,2−ジエチル−1,4,4−トリメチルピペラジニウム、1,3−ジエチル−1,4,4−トリメチルピペラジニウムなど。
The quaternized nitrogen of the piperazine ring;
N, N, N ′, N′-tetramethylpiperazinium, N-ethyl-N, N ′, N′-trimethylpiperazinium, N, N-diethyl-N ′, N′-dimethylpiperazinium, N, N, N′-triethyl-N′-methylpiperazinium, N, N, N ′, N′-tetraethylpiperazinium, 1,1,2,4,4-pentamethylpiperazinium, 1, 1,3,4,4-pentamethylpiperazinium, 1,1,2,3,4,4-hexamethylpiperazinium, 1,1,2,4,4,5-hexamethylpiperazinium, 1,1,2,4,4,6-hexamethylpiperazinium, 1,1,3,4,4,5-hexamethylpiperazinium, 1-ethyl-1,2,4,4-tetramethyl Piperazinium, 1-ethyl-1,3,4,4-tetramethylpiperazi , 2-ethyl-1,1,4,4-tetramethylpiperazinium, 1-ethyl-1,2,4,4-tetramethylpiperazinium, 1-ethyl-1,3,4,4- Tetramethylpiperazinium, 1,1-diethyl-2,4,4-trimethylpiperazinium, 1,4-diethyl-1,2,4-trimethylpiperazinium, 1,2-diethyl-1,4, 4-trimethylpiperazinium, 1,3-diethyl-1,4,4-trimethylpiperazinium and the like.
ピペリジン環の窒素が4級化されたもの;
N,N−ジメチルピペリジニウム、N−エチル−N−メチルピペリジニウム、N,N−ジエチルピペリジニウム、1,1,2−トリメチルピペリジニウム、1,1,3−トリメチルピペリジニウム、1,1,4−トリメチルピペリジニウム、1,2,2−テトラメチルピペリジニウム、1,1,2,3−テトラメチルピペリジニウム、1,1,2,4−テトラメチルピペリジニウム、1,1,2,5−テトラメチルピペリジニウム、1,1,2,6−テトラメチルピペリジニウム、1,1,3,3−テトラメチルピペリジニウム、1,1,3,4−テトラメチルピペリジニウム、1,1,3,5−テトラメチルピペリジニウム、1−エチル−1,2−ジメチルピペリジニウム、1−エチル−1,3−ジメチルピペリジニウム、1−エチル−1,4−ジメチルピペリジニウム、1−エチル−1,2,3−トリメチルピペリジニウム、1−エチル−1,2,4−トリメチルピペリジニウム、1−エチル−1,2,5−トリメチルピペリジニウム、1−エチル−1,2,6−トリメチルピペリジニウム、1−エチル−1,3,4−トリメチルピペリジニウム、1−エチル−1,3,5−トリメチルピペリジニウム、1,1−ジエチル−2−メチルピペリジニウム、1,1−ジエチル−3−メチルピペリジニウム、1,1−ジエチル−4−メチルピペリジニウム、1,1−ジエチル−2,3−ジメチルピペリジニウム、1,1−ジエチル−2,4−ジメチルピペリジニウム、1,1−ジエチル−2,5−ジメチルピペリジニウム、1,1−ジエチル−2,6−ジメチルピペリジニウム、1,1−ジエチル−3,4−ジメチルピペリジニウム、1,1−ジエチル−3,5−ジメチルピペリジニウム、2−エチル−1,1,3−トリメチルピペリジニウム、2−エチル−1,1,4−トリメチルピペリジニウム、2−エチル−1,1,5−トリメチルピペリジニウム、2−エチル−1,1,6−トリメチルピペリジニウム、3−エチル−1,1,2−トリメチルピペリジニウム、3−エチル−1,1,4−トリメチルピペリジニウム、3−エチル−1,1,5−トリメチルピペリジニウム、3−エチル−1,1,6−トリメチルピペリジニウム、4−エチル−1,1,2−トリメチルピペリジニウム、4−エチル−1,1,3−トリメチルピペリジニウム、1,2−ジエチル−1,3−ジメチルピペリジニウム、1−エチル−1,2,4−トリメチルピペリジニウム、1,2−ジエチル−1,5−ジメチルピペリジニウム、1,2−ジエチル−1,6−ジメチルピペリジニウム、1,3−ジエチル−1,5−ジメチルピペリジニウム、1,3−ジエチル−1,4−ジメチルピペリジニウム、1,3−ジエチル−1,6−ジメチルピペリジニウム、1,4−ジエチル−1,2−ジメチルピペリジニウム、1,4−ジエチル−1,3−ジメチルピペリジニウム、1,1,2−トリエチル−3−メチルピペリジニウム、1,1,2−トリエチル−4−メチルピペリジニウム、1,1,2−トリエチル−5−メチルピペリジニウム、1,1,2−トリエチル−6−メチルピペリジニウム、1,1,3−トリエチル−2−メチルピペリジニウム、1,1,3−トリエチル−4−メチルピペリジニウム、1,1,3−トリエチル−5−メチルピペリジニウム、1,1,3−トリエチル−6−メチルピペリジニウム、1,1,4−トリエチル−2−メチルピペリジニウム、1,1,4−トリエチル−3−メチルピペリジニウム、2−エチル−1,1−ジメチルピペリジニウム、3−エチル−1,1−ジメチルピペリジニウム、4−エチル−1,1−ジメチルピペリジニウム、2,3−ジエチル−1,1−ジメチルピペリジニウム、2,4−ジエチル−1,1−ジメチルピペリジニウム、2,5−ジエチル−1,1−ジメチルピペリジニウム、2,6−ジエチル−1,1−ジメチルピペリジニウム、3,4−ジエチル−1,1−ジメチルピペリジニウム、3,5−ジエチル−1,1−ジメチルピペリジニウム、1,2−ジエチル−1−メチルピペリジニウム、1,3−ジエチル−1−メチルピペリジニウム、1,4−ジエチル−1−メチルピペリジニウム、1,2,3−トリエチル−1−メチルピペリジニウム、1,2,4−トリエチル−1−メチルピペリジニウム、1,2,5−トリエチル−1−メチルピペリジニウム、1,2,6−トリエチル−1−メチルピペリジニウム、1,3,4−トリエチル−1−メチルピペリジニウム、1,3,5−トリエチル−1−メチルピペリジニウム、1,1,2−トリエチルピペリジニウム、1,1,4−トリエチルピペリジニウム、1,1,2,3−テトラエチルピペリジニウム、1,1,2,4−テトラエチルピペリジニウム、1,1,2,5−テトラエチルピペリジニウム、1,1,2,6−テトラエチルピペリジニウム、1,1,3,4−テトラメチルピペリジニウム、1,1,3,5−テトラエチルピペリジニウムなど。
Quaternized nitrogen of the piperidine ring;
N, N-dimethylpiperidinium, N-ethyl-N-methylpiperidinium, N, N-diethylpiperidinium, 1,1,2-trimethylpiperidinium, 1,1,3-trimethylpiperidinium 1,1,4-trimethylpiperidinium, 1,2,2-tetramethylpiperidinium, 1,1,2,3-tetramethylpiperidinium, 1,1,2,4-tetramethylpiperidi 1,1,2,5-tetramethylpiperidinium, 1,1,2,6-tetramethylpiperidinium, 1,1,3,3-tetramethylpiperidinium, 1,1,3 4-tetramethylpiperidinium, 1,1,3,5-tetramethylpiperidinium, 1-ethyl-1,2-dimethylpiperidinium, 1-ethyl-1,3-dimethylpiperidinium, 1- Ethyl-1 4-dimethylpiperidinium, 1-ethyl-1,2,3-trimethylpiperidinium, 1-ethyl-1,2,4-trimethylpiperidinium, 1-ethyl-1,2,5-trimethylpiperidi 1-ethyl-1,3,4-trimethylpiperidinium, 1-ethyl-1,3,4-trimethylpiperidinium, 1-ethyl-1,3,5-trimethylpiperidinium, 1,1 -Diethyl-2-methylpiperidinium, 1,1-diethyl-3-methylpiperidinium, 1,1-diethyl-4-methylpiperidinium, 1,1-diethyl-2,3-dimethylpiperidinium 1,1-diethyl-2,4-dimethylpiperidinium, 1,1-diethyl-2,5-dimethylpiperidinium, 1,1-diethyl-2,6-dimethylpiperidinium, -Diethyl-3,4-dimethylpiperidinium, 1,1-diethyl-3,5-dimethylpiperidinium, 2-ethyl-1,1,3-trimethylpiperidinium, 2-ethyl-1,1, 4-trimethylpiperidinium, 2-ethyl-1,1,5-trimethylpiperidinium, 2-ethyl-1,1,6-trimethylpiperidinium, 3-ethyl-1,1,2-trimethylpiperidi Ni, 3-ethyl-1,1,4-trimethylpiperidinium, 3-ethyl-1,1,5-trimethylpiperidinium, 3-ethyl-1,1,6-trimethylpiperidinium, 4-ethyl -1,1,2-trimethylpiperidinium, 4-ethyl-1,1,3-trimethylpiperidinium, 1,2-diethyl-1,3-dimethylpiperidinium, 1-ethyl-1,2, 4 -Trimethylpiperidinium, 1,2-diethyl-1,5-dimethylpiperidinium, 1,2-diethyl-1,6-dimethylpiperidinium, 1,3-diethyl-1,5-dimethylpiperidinium 1,3-diethyl-1,4-dimethylpiperidinium, 1,3-diethyl-1,6-dimethylpiperidinium, 1,4-diethyl-1,2-dimethylpiperidinium, 1,4- Diethyl-1,3-dimethylpiperidinium, 1,1,2-triethyl-3-methylpiperidinium, 1,1,2-triethyl-4-methylpiperidinium, 1,1,2-triethyl-5 -Methylpiperidinium, 1,1,2-triethyl-6-methylpiperidinium, 1,1,3-triethyl-2-methylpiperidinium, 1,1,3-triethyl-4-methylpipe Dinium, 1,1,3-triethyl-5-methylpiperidinium, 1,1,3-triethyl-6-methylpiperidinium, 1,1,4-triethyl-2-methylpiperidinium, 1,1 , 4-triethyl-3-methylpiperidinium, 2-ethyl-1,1-dimethylpiperidinium, 3-ethyl-1,1-dimethylpiperidinium, 4-ethyl-1,1-dimethylpiperidinium 2,3-diethyl-1,1-dimethylpiperidinium, 2,4-diethyl-1,1-dimethylpiperidinium, 2,5-diethyl-1,1-dimethylpiperidinium, 2,6- Diethyl-1,1-dimethylpiperidinium, 3,4-diethyl-1,1-dimethylpiperidinium, 3,5-diethyl-1,1-dimethylpiperidinium, 1,2-diethyl-1- Tilpiperidinium, 1,3-diethyl-1-methylpiperidinium, 1,4-diethyl-1-methylpiperidinium, 1,2,3-triethyl-1-methylpiperidinium, 1,2, 4-triethyl-1-methylpiperidinium, 1,2,5-triethyl-1-methylpiperidinium, 1,2,6-triethyl-1-methylpiperidinium, 1,3,4-triethyl-1 -Methylpiperidinium, 1,3,5-triethyl-1-methylpiperidinium, 1,1,2-triethylpiperidinium, 1,1,4-triethylpiperidinium, 1,1,2,3 -Tetraethylpiperidinium, 1,1,2,4-tetraethylpiperidinium, 1,1,2,5-tetraethylpiperidinium, 1,1,2,6-tetraethylpiperidinium, 1,1 , 3,4-tetramethylpiperidinium, 1,1,3,5-tetraethylpiperidinium, and the like.
ピリジン環の窒素が4級化されたもの;
N−メチルピリジニウム、N−エチルピリジニウム、1,2−ジメチルピリジニウム、1,3−ジメチルピリジニウム、1,4−ジメチルピリジニウム、1−エチル−2−メチルピリジニウム、2−エチル−1−メチルピリジニウム、1−エチル−3−メチルピリジニウム、3−エチル−1−メチルピリジニウム、1−エチル−4−メチルピリジニウム、4−エチル−1−メチルピリジニウム、1,2−ジエチルピリジニウム、1,3−ジエチルピリジニウム、1,4−ジエチルピリジニウム、1,2,3−トリメチルピリジニウム、1,2,4−トリメチルピリジニウム、1,3,4−トリメチルピリジニウム、1,3,5−トリメチルピリジニウム、1,2,5−トリメチルピリジニウム、1,2,6−トリメチルピリジニウム、1−エチル−2,3−ジメチルピリジニウム、1−エチル−2,4−ジメチルピリジニウム、1−エチル−2,5−ジメチルピリジニウム、1−エチル−2,6−ジメチルピリジニウム、1−エチル−3,4−ジメチルピリジニウム、1−エチル−3,5−ジメチルピリジニウム、2−エチル−1,3−ジメチルピリジニウム、2−エチル−1,4−ジメチルピリジニウム、2−エチル−1,5−ジメチルピリジニウム、2−エチル−1,6−ジメチルピリジニウム、3−エチル−1,2−ジメチルピリジニウム、3−エチル−1,4−ジメチルピリジニウム、3−エチル−1,5−ジメチルピリジニウム、3−エチル−1,6−ジメチルピリジニウム、4−エチル−1,2−ジメチルピリジニウム、4−エチル−1,3−ジメチルピリジニウム、1,2−ジエチル−3−メチルピリジニウム、1,2−ジエチル−4−メチルピリジニウム、1,2−ジエチル−5−メチルピリジニウム、1,2−ジエチル−6−メチルピリジニウム、1,3−ジエチル−2−メチルピリジニウム、1,3−ジエチル−4−メチルピリジニウム、1,3−ジエチル−5−メチルピリジニウム、1,3−ジエチル−6−メチルピリジニウム、1,4−ジエチル−2−メチルピリジニウム、1,4−ジエチル−3−メチルピリジニウム、2,3−ジエチル−1−メチルピリジニウム、2,4−ジエチル−1−メチルピリジニウム、2,5−ジエチル−1−メチルピリジニウム、2,6−ジエチル−1−メチルピリジニウム、3,4−ジエチル−1−メチルピリジニウム、3,5−ジエチル−1−メチルピリジニウム、1,2,3,4,5−ペンタメチルピリジニウム、1,2,3,4,6−ペンタメチルピリジニウム、1,2,3,5,6−ペンタメチルピリジニウム、1,2,3,4,5,6−ヘキサメチルピリジニウムなど。
Quaternized nitrogen of the pyridine ring;
N-methylpyridinium, N-ethylpyridinium, 1,2-dimethylpyridinium, 1,3-dimethylpyridinium, 1,4-dimethylpyridinium, 1-ethyl-2-methylpyridinium, 2-ethyl-1-methylpyridinium, 1 -Ethyl-3-methylpyridinium, 3-ethyl-1-methylpyridinium, 1-ethyl-4-methylpyridinium, 4-ethyl-1-methylpyridinium, 1,2-diethylpyridinium, 1,3-diethylpyridinium, 1 , 4-diethylpyridinium, 1,2,3-trimethylpyridinium, 1,2,4-trimethylpyridinium, 1,3,4-trimethylpyridinium, 1,3,5-trimethylpyridinium, 1,2,5-trimethylpyridinium 1,2,6-trimethylpyridinium, 1-e Ru-2,3-dimethylpyridinium, 1-ethyl-2,4-dimethylpyridinium, 1-ethyl-2,5-dimethylpyridinium, 1-ethyl-2,6-dimethylpyridinium, 1-ethyl-3,4- Dimethylpyridinium, 1-ethyl-3,5-dimethylpyridinium, 2-ethyl-1,3-dimethylpyridinium, 2-ethyl-1,4-dimethylpyridinium, 2-ethyl-1,5-dimethylpyridinium, 2-ethyl -1,6-dimethylpyridinium, 3-ethyl-1,2-dimethylpyridinium, 3-ethyl-1,4-dimethylpyridinium, 3-ethyl-1,5-dimethylpyridinium, 3-ethyl-1,6-dimethyl Pyridinium, 4-ethyl-1,2-dimethylpyridinium, 4-ethyl-1,3-dimethylpyridinium, , 2-Diethyl-3-methylpyridinium, 1,2-diethyl-4-methylpyridinium, 1,2-diethyl-5-methylpyridinium, 1,2-diethyl-6-methylpyridinium, 1,3-diethyl-2 -Methylpyridinium, 1,3-diethyl-4-methylpyridinium, 1,3-diethyl-5-methylpyridinium, 1,3-diethyl-6-methylpyridinium, 1,4-diethyl-2-methylpyridinium, 1, 4-diethyl-3-methylpyridinium, 2,3-diethyl-1-methylpyridinium, 2,4-diethyl-1-methylpyridinium, 2,5-diethyl-1-methylpyridinium, 2,6-diethyl-1- Methylpyridinium, 3,4-diethyl-1-methylpyridinium, 3,5-diethyl-1-methylpyridinium 1,2,3,4,5-pentamethylpyridinium, 1,2,3,4,6-pentamethylpyridinium, 1,2,3,5,6-pentamethylpyridinium, 1,2,3 4,5,6-hexamethylpyridinium and the like.
イミダゾール環の窒素が4級化されたもの;
N,N′−ジメチルイミダゾリウム、N−エチル−N′−メチルイミダゾリウム、N,N′−ジエチルイミダゾリウム、1,2,3−トリメチルイミダゾリウム、1,3,4−トリメチルイミダゾリウム、1−エチル−2,3−ジメチルイミダゾリウム、1−エチル−3,4−ジメチルイミダゾリウム、1−エチル−3,5−ジメチルイミダゾリウム、2−エチル−1,3−ジメチルイミダゾリウム、4−エチル−1,3−ジメチルイミダゾリウム、1,2−ジエチル−3−メチルイミダゾリウム、1,4−ジエチル−3−メチルイミダゾリウム、1,5−ジエチル−3−メチルイミダゾリウム、1,3−ジエチル−2−メチルイミダゾリウム、1,3−ジエチル−4−メチルイミダゾリウム、1,2,3−トリエチルイミダゾリウム、1,3,4−トリエチルイミダゾリウム、1,2,3,4−テトラメチルイミダゾリウム、1−エチル−2,3,4−トリメチルイミダゾリウム、1−エチル−2,3,5−トリメチルイミダゾリウム、1−エチル−3,4,5−トリメチルイミダゾリウム、2−エチル−1,3,4−トリメチルイミダゾリウム、4−エチル−1,2,3−トリメチルイミダゾリウム、1,2−ジエチル−3,4−ジメチルイミダゾリウム、1,3−ジエチル−2,4−ジメチルイミダゾリウム、1,4−ジエチル−2,3−ジメチルイミダゾリウム、1,4−ジエチル−2,5−ジメチルイミダゾリウム、2,4−ジエチル−1,3−ジメチルイミダゾリウム、4,5−ジエチル−1,3−ジメチルイミダゾリウム、1,2,3−トリエチル−4−メチルイミダゾリウム、1,2,4−トリエチル−3−メチルイミダゾリウム、1,2,5−トリエチル−3−メチルイミダゾリウム、1,3,4−トリエチル−2−メチルイミダゾリウム、1,3,4−トリエチル−5−メチルイミダゾリウム、1,4,5−トリエチル−3−メチルイミダゾリウム、1,2,3,4,5−ペンタメチルイミダゾリウムなど。
The imidazole ring nitrogen is quaternized;
N, N'-dimethylimidazolium, N-ethyl-N'-methylimidazolium, N, N'-diethylimidazolium, 1,2,3-trimethylimidazolium, 1,3,4-trimethylimidazolium, 1 -Ethyl-2,3-dimethylimidazolium, 1-ethyl-3,4-dimethylimidazolium, 1-ethyl-3,5-dimethylimidazolium, 2-ethyl-1,3-dimethylimidazolium, 4-ethyl -1,3-dimethylimidazolium, 1,2-diethyl-3-methylimidazolium, 1,4-diethyl-3-methylimidazolium, 1,5-diethyl-3-methylimidazolium, 1,3-diethyl 2-methylimidazolium, 1,3-diethyl-4-methylimidazolium, 1,2,3-triethylimidazolium, 1, , 4-triethylimidazolium, 1,2,3,4-tetramethylimidazolium, 1-ethyl-2,3,4-trimethylimidazolium, 1-ethyl-2,3,5-trimethylimidazolium, 1- Ethyl-3,4,5-trimethylimidazolium, 2-ethyl-1,3,4-trimethylimidazolium, 4-ethyl-1,2,3-trimethylimidazolium, 1,2-diethyl-3,4- Dimethylimidazolium, 1,3-diethyl-2,4-dimethylimidazolium, 1,4-diethyl-2,3-dimethylimidazolium, 1,4-diethyl-2,5-dimethylimidazolium, 2,4- Diethyl-1,3-dimethylimidazolium, 4,5-diethyl-1,3-dimethylimidazolium, 1,2,3-triethyl-4-methylimidazole Zolium, 1,2,4-triethyl-3-methylimidazolium, 1,2,5-triethyl-3-methylimidazolium, 1,3,4-triethyl-2-methylimidazolium, 1,3,4 Triethyl-5-methylimidazolium, 1,4,5-triethyl-3-methylimidazolium, 1,2,3,4,5-pentamethylimidazolium and the like.
Q+で表される第4級ホスホニウム基としては、通常は中心原子のリン原子にアルキル基、シクロアルキル基、アリール基、アラルキル基等の、炭素数1〜20、好ましくは1〜5の炭化水素基が結合したものが用いられる。これらの炭化水素基の2個又は3個が相互に結合して環を形成していてもよい。また、これらの炭化水素基には水酸基、アミノ基、ニトロ基、シアノ基、カルボキシル基、エーテル基又はアルデヒド基などの置換基が結合していてもよい。第4級ホスホニウム基としては、例えば下記のようなものが用いられる。 The quaternary phosphonium group represented by Q + is usually a carbon atom having 1 to 20 carbon atoms, preferably 1 to 5 carbon atoms such as an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, etc., on the phosphorus atom of the central atom. Those having a hydrogen group bonded thereto are used. Two or three of these hydrocarbon groups may be bonded to each other to form a ring. In addition, a substituent such as a hydroxyl group, amino group, nitro group, cyano group, carboxyl group, ether group or aldehyde group may be bonded to these hydrocarbon groups. Examples of the quaternary phosphonium group include the following.
テトラメチルホスホニウム、エチルトリメチルホスホニウム、ジエチルジメチルホスホニウム、トリエチルメチルホスホニウム、テトラエチルホスホニウム、トリメチル−n−プロピルホスホニウム、トリメチルイソプロピルホスホニウム、エチルジメチル−n−プロピルホスホニウム、エチルジメチルイソプロピルホスホニウム、ジエチルメチル−n−プロピルホスホニウム、ジエチルメチルイソプロピルホスホニウム、ジメチルジ−n−プロピルホスホニウム、ジメチル−n−プロピルイソプロピルホスホニウム、ジメチルジイソプロピルホスホニウム、トリエチル−n−プロピルホスホニウム、n−ブチルトリメチルホスホニウム、イソブチルトリメチルホスホニウム、t−ブチルトリメチルホスホニウム、トリエチルイソプロピルホスホニウム、エチルメチルジ−n−プロピルホスホニウム、エチルメチル−n−プロピルイソプロピルホスホニウム、エチルメチルジイソプロピルホスホニウム、n−ブチルエチルジメチルホスホニウム、イソブチルエチルジメチルホスホニウム、t−ブチルエチルジメチルホスホニウム、ジエチルジ−n−プロピルホスホニウム、ジエチル−n−プロピルイソプロピルホスホニウム、ジエチルジイソプロピルホスホニウム、メチルトリ−n−プロピルホスホニウム、メチルジ−n−プロピルイソプロピルホスホニウム、メチル−n−プロピルジイソプロピルホスホニウム、n−ブチルトリエチルホスホニウム、イソブチルトリエチルホスホニウム、t−ブチルトリエチルホスホニウム,ジ−n−ブチルジメチルホスホニウム、ジイソブチルジメチルホスホニウム、ジ−t−ブチルジメチルホスホニウム、n−ブチルイソブチルジメチルホスホニウム、n−ブチル−t−ブチルジメチルホスホニウム、イソブチル−t−ブチルジメチルホスホニウムなど。 Tetramethylphosphonium, ethyltrimethylphosphonium, diethyldimethylphosphonium, triethylmethylphosphonium, tetraethylphosphonium, trimethyl-n-propylphosphonium, trimethylisopropylphosphonium, ethyldimethyl-n-propylphosphonium, ethyldimethylisopropylphosphonium, diethylmethyl-n-propylphosphonium , Diethylmethylisopropylphosphonium, dimethyldi-n-propylphosphonium, dimethyl-n-propylisopropylphosphonium, dimethyldiisopropylphosphonium, triethyl-n-propylphosphonium, n-butyltrimethylphosphonium, isobutyltrimethylphosphonium, t-butyltrimethylphosphonium, triethylisopropyl Ho Phonium, ethylmethyldi-n-propylphosphonium, ethylmethyl-n-propylisopropylphosphonium, ethylmethyldiisopropylphosphonium, n-butylethyldimethylphosphonium, isobutylethyldimethylphosphonium, t-butylethyldimethylphosphonium, diethyldi-n-propylphosphonium, diethyl N-propylisopropylphosphonium, diethyldiisopropylphosphonium, methyltri-n-propylphosphonium, methyldi-n-propylisopropylphosphonium, methyl-n-propyldiisopropylphosphonium, n-butyltriethylphosphonium, isobutyltriethylphosphonium, t-butyltriethylphosphonium, Di-n-butyldimethylphosphonium, diisobutyl Methyl phosphonium, di -t- butyl dimethyl phosphonium, n- butyl isobutyl dimethyl phosphonium, n- butyl -t- butyl dimethyl phosphonium, such as isobutyl -t- butyl dimethyl phosphonium.
フッ素を含む化合物からなる電解質の非水電解液中の濃度は、0.1〜3.0M/lが適当であり、特に0.5〜1.5M/lが好ましい。濃度が低すぎると、電解液の導電率が低いために内部抵抗が増大する。逆に高すぎると、低温になった時に塩が析出して不具合を生じる恐れがある。
電解液用の非水溶媒としては、特に限定されるものではないが、エチレンカーボネート、プロピレンカーボネート、ブチレンカーボネート、ガンマブチロラクトン、アセトニトリル、ジメチルホルムアミド、スルホランなどを、単独で又はいくつかを混合して用いればよい。また、これらの溶媒にジメチルカーボネート、エチルメチルカーボネート、ジエチルカーボネートなどの鎖状カーボネートや、酢酸メチル、プロピレン酸メチル等の脂肪族モノカルボン酸エステルを適宜混合して使用することもできる。
The concentration of the electrolyte composed of a compound containing fluorine in the non-aqueous electrolyte is suitably 0.1 to 3.0 M / l, particularly preferably 0.5 to 1.5 M / l. If the concentration is too low, the internal resistance increases because the conductivity of the electrolyte is low. On the other hand, if the temperature is too high, salt may precipitate when the temperature is low, causing a problem.
The non-aqueous solvent for the electrolytic solution is not particularly limited, but ethylene carbonate, propylene carbonate, butylene carbonate, gamma butyrolactone, acetonitrile, dimethylformamide, sulfolane, etc. may be used alone or in combination. That's fine. In addition, chain solvents such as dimethyl carbonate, ethyl methyl carbonate, and diethyl carbonate, and aliphatic monocarboxylic acid esters such as methyl acetate and methyl propylene acid can be appropriately mixed and used in these solvents.
以下に実施例により本発明をさらに具体的に説明するが、本発明はこれらの実施例により限定されるものではない。
なお、電解液中のフッ化水素の含有量及び、この電解液を用いて製造した電気二重層コンデンサの特性は下記により測定した。
The present invention will be described more specifically with reference to the following examples. However, the present invention is not limited to these examples.
The content of hydrogen fluoride in the electrolytic solution and the characteristics of the electric double layer capacitor produced using this electrolytic solution were measured as follows.
フッ化水素の含有量;
電解液10gを化学天秤を用いて共栓付きフラスコに精秤した。これに0℃の冷水を加えて全体で100mlとしたのち、ブロムチモールブルーを指示薬として1/10規定の水酸化ナトリウム水溶液で滴定した。溶液が橙色から青紫色に変化して5秒間持続する点を滴定の終点とした。フッ化水素の含有量は下記式により算出される。
C=(0.002×A×F/S)×106
ここで
C:フッ化水素の含有量(ppm)
A:滴定に要した水酸化ナトリウム水溶液の量(ml)
F:水酸化ナトリウム水溶液のファクター
S:電解液の重量(g)
Content of hydrogen fluoride;
10 g of the electrolytic solution was precisely weighed into a flask with a stopper using a chemical balance. To this was added cold water at 0 ° C. to make a total of 100 ml, and titrated with a 1/10 normal aqueous sodium hydroxide solution using bromthymol blue as an indicator. The point at which the solution changed from orange to blue-violet and lasted for 5 seconds was used as the end point of the titration. The content of hydrogen fluoride is calculated by the following formula.
C = (0.002 × A × F / S) × 10 6
Where C: hydrogen fluoride content (ppm)
A: Amount of sodium hydroxide aqueous solution required for titration (ml)
F: Factor of sodium hydroxide aqueous solution S: Weight of electrolyte (g)
電気二重層コンデンサの特性;
活性炭粉末(比表面積2000m2/g)10重量部にポリテトラフルオロエチレン1重量部を加え、更に水を加えて湿式混練したのち厚さ0.7mmのシートに成形した。このシートを直径15mmの円板状に打抜き、加熱して水分を蒸発させて分極性電極を製作した。この分極性電極2枚を中間にポリプロピレン製不織布からなるセパレーターを介して対向させて、ステンレス鋼製の缶と蓋からなる容器に収容した。これに電解液を注入して分極性電極及びセパレーターに電解液を十分に含浸させたのち、ポリプロピレン製のパッキングを介して、缶と蓋の端部をかしめて封口し、直径20mm、厚さ2.0mmの電気二重層コンデンサを製作した。
Characteristics of electric double layer capacitors;
1 part by weight of polytetrafluoroethylene was added to 10 parts by weight of activated carbon powder (specific surface area 2000 m 2 / g), water was further added and wet-kneaded, and then formed into a sheet having a thickness of 0.7 mm. This sheet was punched into a disk shape having a diameter of 15 mm, and heated to evaporate the water, thereby producing a polarizable electrode. The two polarizable electrodes were opposed to each other via a separator made of polypropylene nonwoven fabric, and accommodated in a container made of a stainless steel can and a lid. After pouring the electrolyte into this and sufficiently impregnating the polarizable electrode and the separator with the electrolyte, the end of the can and the lid is crimped and sealed through a polypropylene packing, and the diameter is 20 mm and the thickness is 2 A 0.0 mm electric double layer capacitor was manufactured.
この電気二重層コンデンサについて、2.8Vの電圧を印加したときの初期容量及び内部抵抗を測定した。また、2.8Vの電圧を印加しながら70℃で1000時間保存した後の容量を測定し、初期容量からの容量劣化率を算出した。なお、内部抵抗は周波数1kHzで交流二端子法により測定した。 With respect to this electric double layer capacitor, an initial capacity and an internal resistance when a voltage of 2.8 V was applied were measured. Further, the capacity after being stored at 70 ° C. for 1000 hours while applying a voltage of 2.8 V was measured, and the capacity deterioration rate from the initial capacity was calculated. The internal resistance was measured by an AC two-terminal method at a frequency of 1 kHz.
実施例1及び比較例1
室温下、露点−60℃の乾燥窒素雰囲気中で、高純度のプロピレンカーボネートにトリエチルメチルアンモニウムテトラフルオロボレート(Et3MeN+・BF4 −)を1モル/lとなるように溶解して電解液を調製した。
この電解液10重量部に高純度のプロピレンカーボネート1重量部を加えたのち、5mmHgの減圧下で釜温120℃に加熱して1重量部のプロピレンカーボネートを留出させ、電解液を回収した。これらの電解液のフッ化水素含有量、及びこれらを用いて製造した電気二重層コンデンサの特性を表1に示す。
Example 1 and Comparative Example 1
At room temperature, in a dry nitrogen atmosphere with a dew point of −60 ° C., triethylmethylammonium tetrafluoroborate (Et 3 MeN + · BF 4 − ) was dissolved in high-purity propylene carbonate to a concentration of 1 mol / l, and an electrolyte solution Was prepared.
After adding 1 part by weight of high-purity propylene carbonate to 10 parts by weight of this electrolytic solution, it was heated to a kettle temperature of 120 ° C. under a reduced pressure of 5 mmHg to distill 1 part by weight of propylene carbonate, and the electrolytic solution was recovered. Table 1 shows the hydrogen fluoride content of these electrolytes and the characteristics of the electric double layer capacitors produced using them.
実施例2及び比較例2
室温下、露点−60℃の乾燥窒素雰囲気中で、高純度のプロピレンカーボネートにテトラエチルアンモニウムテトラフルオロボレート(Et4N+・BF4 −)を1モル/lとなるように溶解して電解液を調製した。
この電解液100重量部に、活性アルミナ(AC−11、比表面積140m2/g、平均粒径80〜100μm、スミアル製品販売(株)製品)を1%希硝酸で洗浄したのち十分に水洗し、550℃で4時間乾燥したもの1重量部を加え、30分間撹拌したのち濾過し、電解液を回収した。
これらの電解液のフッ化水素含有量、及びこれらを用いて製造した電気二重層コンデンサの特性を表1に示す。
Example 2 and Comparative Example 2
At room temperature, in a dry nitrogen atmosphere with a dew point of −60 ° C., tetraethylammonium tetrafluoroborate (Et 4 N + .BF 4 − ) is dissolved in high-purity propylene carbonate so as to have a concentration of 1 mol / l. Prepared.
To 100 parts by weight of the electrolytic solution, activated alumina (AC-11, specific surface area 140 m 2 / g, average particle size 80-100 μm, Sumial Products Sales Co., Ltd.) was washed with 1% dilute nitric acid and then thoroughly washed with water. 1 part by weight of a product dried at 550 ° C. for 4 hours was added, stirred for 30 minutes, and then filtered to recover the electrolyte.
Table 1 shows the hydrogen fluoride content of these electrolytes and the characteristics of the electric double layer capacitors produced using them.
比較例3
室温下、露点−60℃の乾燥窒素雰囲気中で、高純度プロピレンカーボネートにテトラエチルホスホニウムテトラフルオロボレート(Et4P+・BF4 −)を1モル/lとなるように溶解して電解液を調製した。この電解液のフッ化水素の含有量及びこれを用いて製造した電気二重層コンデンサの特性を表1に示す。
Comparative Example 3
Prepare an electrolyte solution by dissolving tetraethylphosphonium tetrafluoroborate (Et 4 P + .BF 4 − ) at 1 mol / l in high-purity propylene carbonate in a dry nitrogen atmosphere at a dew point of −60 ° C. at room temperature. did. Table 1 shows the content of hydrogen fluoride in the electrolytic solution and the characteristics of an electric double layer capacitor produced using the same.
実施例3
比較例3で用いたと同じテトラエチルホスホニウムテトラフルオロボレート40gをメタノール100gに投入し、64℃に加熱して溶解させたのち熱時濾過した。濾液を5℃まで徐冷し、析出した結晶を濾取して5℃のメタノールで洗浄したのち減圧乾燥した。この再結晶により精製したテトラエチルホスホニウムテトラフルオロボレートを用いた以外は、比較例3と全く同様にして電解液を調製した。この電解液のフッ化水素の含有量、及びこれを用いて製造した電気二重層コンデンサの特性を表1に示す。
Example 3
40 g of the same tetraethylphosphonium tetrafluoroborate used in Comparative Example 3 was put into 100 g of methanol, dissolved by heating to 64 ° C., and then filtered while hot. The filtrate was gradually cooled to 5 ° C., and the precipitated crystals were collected by filtration, washed with methanol at 5 ° C., and then dried under reduced pressure. An electrolytic solution was prepared in exactly the same manner as in Comparative Example 3 except that tetraethylphosphonium tetrafluoroborate purified by this recrystallization was used. Table 1 shows the content of hydrogen fluoride in the electrolytic solution and the characteristics of the electric double layer capacitor produced using the same.
Claims (6)
(化1)
Q+X− …(I)
(式中、Q+は第4級アンモニウム基又は第4級ホスホニウム基を表し、X−はPF6 −、BF4 −、AsF6 −、N(CF3SO3)2 − 、C(CF3SO3)3 −、SbF6 −及びRfSO3 −(Rfは炭素数1〜8のフルオロアルキル基)よりなる群から選ばれた対イオンを表す。) The nonaqueous electrolysis according to any one of claims 1 to 3, wherein the fluorine-containing compound is a quaternary ammonium salt or a quaternary phosphonium salt represented by the following general formula (I). Liquid manufacturing method.
(Chemical formula 1)
Q + X − (I)
(In the formula, Q + represents a quaternary ammonium group or a quaternary phosphonium group, and X − represents PF 6 − , BF 4 − , AsF 6 − , N (CF 3 SO 3 ) 2 − , C (CF 3 SO 3 ) 3 − , SbF 6 — and RfSO 3 — (Rf represents a counter ion selected from the group consisting of 1 to 8 carbon atoms).
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