JP5511452B2 - 電解質及びそれを用いたリチウム二次電池 - Google Patents
電解質及びそれを用いたリチウム二次電池 Download PDFInfo
- Publication number
- JP5511452B2 JP5511452B2 JP2010060527A JP2010060527A JP5511452B2 JP 5511452 B2 JP5511452 B2 JP 5511452B2 JP 2010060527 A JP2010060527 A JP 2010060527A JP 2010060527 A JP2010060527 A JP 2010060527A JP 5511452 B2 JP5511452 B2 JP 5511452B2
- Authority
- JP
- Japan
- Prior art keywords
- ionic liquid
- electrolyte
- cation
- anion
- ionic
- 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.)
- Expired - Fee Related
Links
- 239000003792 electrolyte Substances 0.000 title claims description 58
- 229910052744 lithium Inorganic materials 0.000 title claims description 48
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 title claims description 43
- 239000002608 ionic liquid Substances 0.000 claims description 138
- -1 cyanophosphate anion Chemical class 0.000 claims description 88
- 239000002001 electrolyte material Substances 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 14
- 230000001681 protective effect Effects 0.000 claims description 13
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 150000002892 organic cations Chemical class 0.000 claims description 6
- 125000000129 anionic group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000007773 negative electrode material Substances 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 4
- 229910001411 inorganic cation Inorganic materials 0.000 claims description 4
- BEEQOAKWOKFBIM-UHFFFAOYSA-N phosphono cyanate Chemical compound OP(O)(=O)OC#N BEEQOAKWOKFBIM-UHFFFAOYSA-N 0.000 claims description 4
- 150000001767 cationic compounds Chemical class 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- 239000010406 cathode material Substances 0.000 claims 1
- 238000007333 cyanation reaction Methods 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 34
- 150000001450 anions Chemical class 0.000 description 24
- 150000001768 cations Chemical class 0.000 description 24
- 238000005481 NMR spectroscopy Methods 0.000 description 15
- 150000007960 acetonitrile Chemical class 0.000 description 14
- 239000002904 solvent Substances 0.000 description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000011149 active material Substances 0.000 description 8
- 239000002131 composite material Substances 0.000 description 8
- 230000007423 decrease Effects 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 230000009467 reduction Effects 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 239000012025 fluorinating agent Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 6
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- 239000007774 positive electrode material Substances 0.000 description 5
- 239000002516 radical scavenger Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- LFAGQMCIGQNPJG-UHFFFAOYSA-N silver cyanide Chemical compound [Ag+].N#[C-] LFAGQMCIGQNPJG-UHFFFAOYSA-N 0.000 description 5
- 229940098221 silver cyanide Drugs 0.000 description 5
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 4
- XUAXVBUVQVRIIQ-UHFFFAOYSA-N 1-butyl-2,3-dimethylimidazol-3-ium Chemical compound CCCCN1C=C[N+](C)=C1C XUAXVBUVQVRIIQ-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 229910013528 LiN(SO2 CF3)2 Inorganic materials 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229920001940 conductive polymer Polymers 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229910013063 LiBF 4 Inorganic materials 0.000 description 3
- 229910012424 LiSO 3 Inorganic materials 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 239000002033 PVDF binder Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000008151 electrolyte solution Substances 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-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
- HVVRUQBMAZRKPJ-UHFFFAOYSA-N 1,3-dimethylimidazolium Chemical compound CN1C=C[N+](C)=C1 HVVRUQBMAZRKPJ-UHFFFAOYSA-N 0.000 description 2
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 2
- IRGDPGYNHSIIJJ-UHFFFAOYSA-N 1-ethyl-2,3-dimethylimidazol-3-ium Chemical compound CCN1C=C[N+](C)=C1C IRGDPGYNHSIIJJ-UHFFFAOYSA-N 0.000 description 2
- COPVYYIIVFKLAY-UHFFFAOYSA-N 1-ethyl-3,4-dimethylimidazol-1-ium Chemical compound CC[N+]=1C=C(C)N(C)C=1 COPVYYIIVFKLAY-UHFFFAOYSA-N 0.000 description 2
- RVEJOWGVUQQIIZ-UHFFFAOYSA-N 1-hexyl-3-methylimidazolium Chemical compound CCCCCCN1C=C[N+](C)=C1 RVEJOWGVUQQIIZ-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229910012851 LiCoO 2 Inorganic materials 0.000 description 2
- 229910013870 LiPF 6 Inorganic materials 0.000 description 2
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 2
- PMDCZENCAXMSOU-UHFFFAOYSA-N N-ethylacetamide Chemical compound CCNC(C)=O PMDCZENCAXMSOU-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 2
- 239000011267 electrode slurry Substances 0.000 description 2
- 239000004210 ether based solvent Substances 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000010416 ion conductor Substances 0.000 description 2
- 239000003273 ketjen black Substances 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001197 polyacetylene Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 238000001291 vacuum drying Methods 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 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- HNWUWVWSUONNSZ-UHFFFAOYSA-N 1,2-dimethyl-3-(trifluoromethyl)imidazol-1-ium Chemical compound CC=1N(C(F)(F)F)C=C[N+]=1C HNWUWVWSUONNSZ-UHFFFAOYSA-N 0.000 description 1
- NNIBKGZUMJNHID-UHFFFAOYSA-N 1,2-dimethyl-3-propan-2-ylimidazol-1-ium Chemical compound CC(C)[N+]=1C=CN(C)C=1C NNIBKGZUMJNHID-UHFFFAOYSA-N 0.000 description 1
- MXLZUALXSYVAIV-UHFFFAOYSA-N 1,2-dimethyl-3-propylimidazol-1-ium Chemical compound CCCN1C=C[N+](C)=C1C MXLZUALXSYVAIV-UHFFFAOYSA-N 0.000 description 1
- WDXYVJKNSMILOQ-UHFFFAOYSA-N 1,3,2-dioxathiolane 2-oxide Chemical compound O=S1OCCO1 WDXYVJKNSMILOQ-UHFFFAOYSA-N 0.000 description 1
- CDIWYWUGTVLWJM-UHFFFAOYSA-N 1,3,4-trimethylimidazol-1-ium Chemical compound CC1=C[N+](C)=CN1C CDIWYWUGTVLWJM-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 1
- GGPFKGVLNMUFEE-UHFFFAOYSA-N 1,3-bis(1,1,2,2,2-pentafluoroethyl)imidazol-1-ium Chemical compound FC(F)(F)C(F)(F)N1C=C[N+](C(F)(F)C(F)(F)F)=C1 GGPFKGVLNMUFEE-UHFFFAOYSA-N 0.000 description 1
- PLBVFCUDMNTJIR-UHFFFAOYSA-N 1,3-bis(1,1,2,2,3,3,3-heptafluoropropyl)imidazol-1-ium Chemical compound FC(F)(F)C(F)(F)C(F)(F)N1C=C[N+](C(F)(F)C(F)(F)C(F)(F)F)=C1 PLBVFCUDMNTJIR-UHFFFAOYSA-N 0.000 description 1
- NVMGGZYBBRNSJD-UHFFFAOYSA-N 1,3-bis(1,1,2,2,3,3,4,4,4-nonafluorobutyl)imidazol-1-ium Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)N1C=C[N+](C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)=C1 NVMGGZYBBRNSJD-UHFFFAOYSA-N 0.000 description 1
- FUBVZDQOJSTYSR-UHFFFAOYSA-N 1,3-bis(trifluoromethyl)imidazol-1-ium Chemical compound FC(F)(F)N1C=C[N+](C(F)(F)F)=C1 FUBVZDQOJSTYSR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KSKHLLBCEXHIEH-UHFFFAOYSA-N 1,3-dimethylimidazol-1-ium-2-carbonitrile Chemical compound CN1C=C[N+](C)=C1C#N KSKHLLBCEXHIEH-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UZDLMXYACBVNCQ-UHFFFAOYSA-N 1-(1-methoxyethyl)-3-methylimidazol-3-ium Chemical compound COC(C)[N+]=1C=CN(C)C=1 UZDLMXYACBVNCQ-UHFFFAOYSA-N 0.000 description 1
- HPHJLXQRQWXQGB-UHFFFAOYSA-N 1-(2-ethoxyethyl)-1-methylpyrrolidin-1-ium Chemical compound CCOCC[N+]1(C)CCCC1 HPHJLXQRQWXQGB-UHFFFAOYSA-N 0.000 description 1
- DSIZWXRKCNMRRB-UHFFFAOYSA-N 1-(2-methoxyethyl)-1-methylpiperidin-1-ium Chemical compound COCC[N+]1(C)CCCCC1 DSIZWXRKCNMRRB-UHFFFAOYSA-N 0.000 description 1
- IDTCZPKYVMKLRZ-UHFFFAOYSA-N 1-(2-methoxyethyl)-1-methylpyrrolidin-1-ium Chemical compound COCC[N+]1(C)CCCC1 IDTCZPKYVMKLRZ-UHFFFAOYSA-N 0.000 description 1
- SCBMOTIJMABLLN-UHFFFAOYSA-N 1-(2-methoxyphenyl)-1-methylpiperidin-1-ium Chemical compound COC1=CC=CC=C1[N+]1(C)CCCCC1 SCBMOTIJMABLLN-UHFFFAOYSA-N 0.000 description 1
- UVCPHBWNKAXVPC-UHFFFAOYSA-N 1-butyl-1-methylpiperidin-1-ium Chemical compound CCCC[N+]1(C)CCCCC1 UVCPHBWNKAXVPC-UHFFFAOYSA-N 0.000 description 1
- PXELHGDYRQLRQO-UHFFFAOYSA-N 1-butyl-1-methylpyrrolidin-1-ium Chemical compound CCCC[N+]1(C)CCCC1 PXELHGDYRQLRQO-UHFFFAOYSA-N 0.000 description 1
- UMQMCSRLXDCRNQ-UHFFFAOYSA-N 1-butyl-3,4-dimethylimidazol-1-ium Chemical compound CCCC[N+]=1C=C(C)N(C)C=1 UMQMCSRLXDCRNQ-UHFFFAOYSA-N 0.000 description 1
- JYARJXBHOOZQQD-UHFFFAOYSA-N 1-butyl-3-ethylimidazol-1-ium Chemical compound CCCC[N+]=1C=CN(CC)C=1 JYARJXBHOOZQQD-UHFFFAOYSA-N 0.000 description 1
- FHDQNOXQSTVAIC-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;chloride Chemical compound [Cl-].CCCCN1C=C[N+](C)=C1 FHDQNOXQSTVAIC-UHFFFAOYSA-M 0.000 description 1
- ZHEXBPJIKJYHGD-UHFFFAOYSA-O 1-butyl-4-methyl-1H-imidazol-1-ium-2-carbonitrile Chemical compound CCCC[NH+]1C=C(C)N=C1C#N ZHEXBPJIKJYHGD-UHFFFAOYSA-O 0.000 description 1
- ZFWCUGUBAJVTBO-UHFFFAOYSA-N 1-chlorohexane-1,1-diol Chemical compound ClC(CCCCC)(O)O ZFWCUGUBAJVTBO-UHFFFAOYSA-N 0.000 description 1
- ITMKMGFAZDZEPE-UHFFFAOYSA-N 1-decyl-1-methylpiperidin-1-ium Chemical compound CCCCCCCCCC[N+]1(C)CCCCC1 ITMKMGFAZDZEPE-UHFFFAOYSA-N 0.000 description 1
- YPKUOQRBNZPMAE-UHFFFAOYSA-N 1-decyl-1-methylpyrrolidin-1-ium Chemical compound CCCCCCCCCC[N+]1(C)CCCC1 YPKUOQRBNZPMAE-UHFFFAOYSA-N 0.000 description 1
- LDVVBLGHGCHZBJ-UHFFFAOYSA-N 1-decyl-3-methylimidazolium Chemical compound CCCCCCCCCCN1C=C[N+](C)=C1 LDVVBLGHGCHZBJ-UHFFFAOYSA-N 0.000 description 1
- HLOSFNUKTPAIOO-UHFFFAOYSA-N 1-dodecyl-1-methylpiperidin-1-ium Chemical compound CCCCCCCCCCCC[N+]1(C)CCCCC1 HLOSFNUKTPAIOO-UHFFFAOYSA-N 0.000 description 1
- ULSWKIJRQWZPCQ-UHFFFAOYSA-N 1-dodecyl-1-methylpyrrolidin-1-ium Chemical compound CCCCCCCCCCCC[N+]1(C)CCCC1 ULSWKIJRQWZPCQ-UHFFFAOYSA-N 0.000 description 1
- ILQHIGIKULUQFQ-UHFFFAOYSA-N 1-dodecyl-3-methylimidazolium Chemical compound CCCCCCCCCCCCN1C=C[N+](C)=C1 ILQHIGIKULUQFQ-UHFFFAOYSA-N 0.000 description 1
- CAQYAZNFWDDMIT-UHFFFAOYSA-N 1-ethoxy-2-methoxyethane Chemical compound CCOCCOC CAQYAZNFWDDMIT-UHFFFAOYSA-N 0.000 description 1
- AAINAVGFOSLVFN-UHFFFAOYSA-N 1-ethyl-1-(2-methoxyethyl)piperidin-1-ium Chemical compound COCC[N+]1(CC)CCCCC1 AAINAVGFOSLVFN-UHFFFAOYSA-N 0.000 description 1
- UYYFALOISZSWGK-UHFFFAOYSA-N 1-ethyl-1-(4-methoxyphenyl)piperidin-1-ium Chemical compound C=1C=C(OC)C=CC=1[N+]1(CC)CCCCC1 UYYFALOISZSWGK-UHFFFAOYSA-N 0.000 description 1
- NIHOUJYFWMURBG-UHFFFAOYSA-N 1-ethyl-1-methylpyrrolidin-1-ium Chemical compound CC[N+]1(C)CCCC1 NIHOUJYFWMURBG-UHFFFAOYSA-N 0.000 description 1
- LLTZMORCIOUTDZ-UHFFFAOYSA-N 1-ethyl-3-(trifluoromethyl)imidazol-1-ium Chemical compound CC[N+]=1C=CN(C(F)(F)F)C=1 LLTZMORCIOUTDZ-UHFFFAOYSA-N 0.000 description 1
- BMQZYMYBQZGEEY-UHFFFAOYSA-M 1-ethyl-3-methylimidazolium chloride Chemical compound [Cl-].CCN1C=C[N+](C)=C1 BMQZYMYBQZGEEY-UHFFFAOYSA-M 0.000 description 1
- RMQJBIHRJDFNDM-UHFFFAOYSA-N 1-ethyl-3-propylimidazol-3-ium Chemical compound CCCN1C=C[N+](CC)=C1 RMQJBIHRJDFNDM-UHFFFAOYSA-N 0.000 description 1
- LIQLQIJSJXRLGC-UHFFFAOYSA-O 1-ethyl-4-methyl-1H-imidazol-1-ium-2-carbonitrile Chemical compound CC[NH+]1C=C(C)N=C1C#N LIQLQIJSJXRLGC-UHFFFAOYSA-O 0.000 description 1
- FCZZZYZIQDHCIW-UHFFFAOYSA-N 1-heptyl-3-methylimidazol-3-ium Chemical compound CCCCCCC[N+]=1C=CN(C)C=1 FCZZZYZIQDHCIW-UHFFFAOYSA-N 0.000 description 1
- FHZKIKVDRZVWKN-UHFFFAOYSA-N 1-hexyl-1-methylpiperidin-1-ium Chemical compound CCCCCC[N+]1(C)CCCCC1 FHZKIKVDRZVWKN-UHFFFAOYSA-N 0.000 description 1
- SVONMDAUOJGXHL-UHFFFAOYSA-N 1-hexyl-1-methylpyrrolidin-1-ium Chemical compound CCCCCC[N+]1(C)CCCC1 SVONMDAUOJGXHL-UHFFFAOYSA-N 0.000 description 1
- SWWLEHMBKPSRSI-UHFFFAOYSA-N 1-hexyl-2,3-dimethylimidazol-3-ium Chemical compound CCCCCCN1C=C[N+](C)=C1C SWWLEHMBKPSRSI-UHFFFAOYSA-N 0.000 description 1
- HNYRDAYSGHUSFJ-UHFFFAOYSA-N 1-methyl-1-(2-propan-2-yloxyethyl)pyrrolidin-1-ium Chemical compound CC(C)OCC[N+]1(C)CCCC1 HNYRDAYSGHUSFJ-UHFFFAOYSA-N 0.000 description 1
- XDGPPYJMOCHAGB-UHFFFAOYSA-N 1-methyl-1-octylpiperidin-1-ium Chemical compound CCCCCCCC[N+]1(C)CCCCC1 XDGPPYJMOCHAGB-UHFFFAOYSA-N 0.000 description 1
- JWPBORWCDZAHAU-UHFFFAOYSA-N 1-methyl-1-octylpyrrolidin-1-ium Chemical compound CCCCCCCC[N+]1(C)CCCC1 JWPBORWCDZAHAU-UHFFFAOYSA-N 0.000 description 1
- FPDXTDBUOUGVNV-UHFFFAOYSA-N 1-methyl-1-pentylpiperidin-1-ium Chemical compound CCCCC[N+]1(C)CCCCC1 FPDXTDBUOUGVNV-UHFFFAOYSA-N 0.000 description 1
- RRYKUXCBJXYIOD-UHFFFAOYSA-N 1-methyl-1-pentylpyrrolidin-1-ium Chemical compound CCCCC[N+]1(C)CCCC1 RRYKUXCBJXYIOD-UHFFFAOYSA-N 0.000 description 1
- OGLIVJFAKNJZRE-UHFFFAOYSA-N 1-methyl-1-propylpiperidin-1-ium Chemical compound CCC[N+]1(C)CCCCC1 OGLIVJFAKNJZRE-UHFFFAOYSA-N 0.000 description 1
- YQFWGCSKGJMGHE-UHFFFAOYSA-N 1-methyl-1-propylpyrrolidin-1-ium Chemical compound CCC[N+]1(C)CCCC1 YQFWGCSKGJMGHE-UHFFFAOYSA-N 0.000 description 1
- PAWCWIZSIIUWRO-UHFFFAOYSA-N 1-methyl-3-(trifluoromethyl)imidazol-1-ium Chemical compound CN1C=C[N+](C(F)(F)F)=C1 PAWCWIZSIIUWRO-UHFFFAOYSA-N 0.000 description 1
- JFYZBXKLRPWSGV-UHFFFAOYSA-N 1-methyl-3-propyl-2h-imidazole Chemical compound CCCN1CN(C)C=C1 JFYZBXKLRPWSGV-UHFFFAOYSA-N 0.000 description 1
- WVDDUSFOSWWJJH-UHFFFAOYSA-N 1-methyl-3-propylimidazol-1-ium Chemical compound CCCN1C=C[N+](C)=C1 WVDDUSFOSWWJJH-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-O 1-methylimidazole Chemical compound CN1C=C[NH+]=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-O 0.000 description 1
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 description 1
- XQPYWRYOADEREX-UHFFFAOYSA-N 2-(3-methylimidazol-3-ium-1-yl)acetonitrile Chemical compound C[N+]=1C=CN(CC#N)C=1 XQPYWRYOADEREX-UHFFFAOYSA-N 0.000 description 1
- GAJZUGBMKQTLEM-UHFFFAOYSA-N 2-(3-methylimidazol-3-ium-1-yl)propanenitrile Chemical compound N#CC(C)[N+]=1C=CN(C)C=1 GAJZUGBMKQTLEM-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- YPPVIFMRSGJHRJ-UHFFFAOYSA-N 2-butyl-1,3-dimethylimidazol-1-ium Chemical compound CCCCC=1N(C)C=C[N+]=1C YPPVIFMRSGJHRJ-UHFFFAOYSA-N 0.000 description 1
- PLLVTSBBBKLRSO-UHFFFAOYSA-N 2-ethoxyethyl(trimethyl)azanium Chemical compound CCOCC[N+](C)(C)C PLLVTSBBBKLRSO-UHFFFAOYSA-N 0.000 description 1
- 150000008625 2-imidazolidinones Chemical class 0.000 description 1
- TWIHZYSDMBKSPS-UHFFFAOYSA-N 2-methoxyethyl-dimethyl-propylazanium Chemical compound CCC[N+](C)(C)CCOC TWIHZYSDMBKSPS-UHFFFAOYSA-N 0.000 description 1
- YBNPSQVVFYIDOF-UHFFFAOYSA-N 2-methyl-1,3-bis(trifluoromethyl)imidazol-1-ium Chemical compound CC=1N(C(F)(F)F)C=C[N+]=1C(F)(F)F YBNPSQVVFYIDOF-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- MCMFEZDRQOJKMN-UHFFFAOYSA-O 3-butyl-1h-imidazol-3-ium Chemical compound CCCCN1C=C[NH+]=C1 MCMFEZDRQOJKMN-UHFFFAOYSA-O 0.000 description 1
- OOWFYDWAMOKVSF-UHFFFAOYSA-N 3-methoxypropanenitrile Chemical compound COCCC#N OOWFYDWAMOKVSF-UHFFFAOYSA-N 0.000 description 1
- VWIIJDNADIEEDB-UHFFFAOYSA-N 3-methyl-1,3-oxazolidin-2-one Chemical compound CN1CCOC1=O VWIIJDNADIEEDB-UHFFFAOYSA-N 0.000 description 1
- WXMVWUBWIHZLMQ-UHFFFAOYSA-N 3-methyl-1-octylimidazolium Chemical compound CCCCCCCCN1C=C[N+](C)=C1 WXMVWUBWIHZLMQ-UHFFFAOYSA-N 0.000 description 1
- SROUAIZIOIOQID-UHFFFAOYSA-N 4-(3-methylimidazol-3-ium-1-yl)butanenitrile Chemical compound CN1C=C[N+](CCCC#N)=C1 SROUAIZIOIOQID-UHFFFAOYSA-N 0.000 description 1
- JHWDFYSDNMJWBC-UHFFFAOYSA-O 4-methyl-1-propyl-1H-imidazol-1-ium-2-carbonitrile Chemical compound CCC[NH+]1C=C(C)N=C1C#N JHWDFYSDNMJWBC-UHFFFAOYSA-O 0.000 description 1
- 229910016467 AlCl 4 Inorganic materials 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229910010238 LiAlCl 4 Inorganic materials 0.000 description 1
- 229910015015 LiAsF 6 Inorganic materials 0.000 description 1
- 229910013075 LiBF Inorganic materials 0.000 description 1
- 229910010707 LiFePO 4 Inorganic materials 0.000 description 1
- 229910015643 LiMn 2 O 4 Inorganic materials 0.000 description 1
- 229910014689 LiMnO Inorganic materials 0.000 description 1
- 229910013131 LiN Inorganic materials 0.000 description 1
- 229910015915 LiNi0.8Co0.2O2 Inorganic materials 0.000 description 1
- 229910014411 LiNi1/2Mn1/2O2 Inorganic materials 0.000 description 1
- 229910014422 LiNi1/3Mn1/3Co1/3O2 Inorganic materials 0.000 description 1
- 229910013290 LiNiO 2 Inorganic materials 0.000 description 1
- 229910012513 LiSbF 6 Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 1
- 229910020808 NaBF Inorganic materials 0.000 description 1
- GSBKRFGXEJLVMI-UHFFFAOYSA-N Nervonyl carnitine Chemical compound CCC[N+](C)(C)C GSBKRFGXEJLVMI-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000199911 Peridinium Species 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229910021608 Silver(I) fluoride Inorganic materials 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- XXHLPALGZBHSQA-UHFFFAOYSA-N [fluorooxy(hydroxy)phosphoryl] cyanate Chemical compound FOP(=O)(O)OC#N XXHLPALGZBHSQA-UHFFFAOYSA-N 0.000 description 1
- 239000006230 acetylene black Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ANFWGAAJBJPAHX-UHFFFAOYSA-N bis(fluorosulfonyl)azanide;1-ethyl-3-methylimidazol-3-ium Chemical compound CC[N+]=1C=CN(C)C=1.FS(=O)(=O)[N-]S(F)(=O)=O ANFWGAAJBJPAHX-UHFFFAOYSA-N 0.000 description 1
- LRESCJAINPKJTO-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-ethyl-3-methylimidazol-3-ium Chemical compound CCN1C=C[N+](C)=C1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F LRESCJAINPKJTO-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- LFLBHTZRLVHUQC-UHFFFAOYSA-N butyl methanesulfonate Chemical compound CCCCOS(C)(=O)=O LFLBHTZRLVHUQC-UHFFFAOYSA-N 0.000 description 1
- IUNCEDRRUNZACO-UHFFFAOYSA-N butyl(trimethyl)azanium Chemical compound CCCC[N+](C)(C)C IUNCEDRRUNZACO-UHFFFAOYSA-N 0.000 description 1
- DWTRKMZYVQNZTB-UHFFFAOYSA-N butyl-(2-methoxyethyl)-dimethylazanium Chemical compound CCCC[N+](C)(C)CCOC DWTRKMZYVQNZTB-UHFFFAOYSA-N 0.000 description 1
- VJBODIYZSOOKES-UHFFFAOYSA-N butyl-ethyl-dimethylazanium Chemical compound CCCC[N+](C)(C)CC VJBODIYZSOOKES-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 239000003660 carbonate based solvent Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000002482 conductive additive Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- UCDHYFZYUGDETN-UHFFFAOYSA-N cyanophosphonic acid Chemical compound OP(O)(=O)C#N UCDHYFZYUGDETN-UHFFFAOYSA-N 0.000 description 1
- RKMJXTWHATWGNX-UHFFFAOYSA-N decyltrimethylammonium ion Chemical compound CCCCCCCCCC[N+](C)(C)C RKMJXTWHATWGNX-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229940105990 diglycerin Drugs 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- VVADOOSZSOSTOC-UHFFFAOYSA-N dimethyl(propyl)sulfanium Chemical compound CCC[S+](C)C VVADOOSZSOSTOC-UHFFFAOYSA-N 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- VICYBMUVWHJEFT-UHFFFAOYSA-N dodecyltrimethylammonium ion Chemical compound CCCCCCCCCCCC[N+](C)(C)C VICYBMUVWHJEFT-UHFFFAOYSA-N 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- ZOZZQPFBMNNPPO-UHFFFAOYSA-N ethyl-dimethyl-propylazanium Chemical compound CCC[N+](C)(C)CC ZOZZQPFBMNNPPO-UHFFFAOYSA-N 0.000 description 1
- BEURYHDWKDICEO-UHFFFAOYSA-N ethyl-hexyl-dimethylazanium Chemical compound CCCCCC[N+](C)(C)CC BEURYHDWKDICEO-UHFFFAOYSA-N 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- YOMFVLRTMZWACQ-UHFFFAOYSA-N ethyltrimethylammonium Chemical compound CC[N+](C)(C)C YOMFVLRTMZWACQ-UHFFFAOYSA-N 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910021397 glassy carbon Inorganic materials 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PISCILXZPLTTFP-UHFFFAOYSA-N heptyl(trimethyl)azanium Chemical compound CCCCCCC[N+](C)(C)C PISCILXZPLTTFP-UHFFFAOYSA-N 0.000 description 1
- YWUUCAMRVADOCK-UHFFFAOYSA-N hexyl(dimethyl)sulfanium Chemical compound CCCCCC[S+](C)C YWUUCAMRVADOCK-UHFFFAOYSA-N 0.000 description 1
- XTPRURKTXNFVQT-UHFFFAOYSA-N hexyl(trimethyl)azanium Chemical compound CCCCCC[N+](C)(C)C XTPRURKTXNFVQT-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229940006487 lithium cation Drugs 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- NNCAWEWCFVZOGF-UHFFFAOYSA-N mepiquat Chemical compound C[N+]1(C)CCCCC1 NNCAWEWCFVZOGF-UHFFFAOYSA-N 0.000 description 1
- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- LIIBOJGBDQRXAY-UHFFFAOYSA-N methoxymethylphosphane Chemical compound COCP LIIBOJGBDQRXAY-UHFFFAOYSA-N 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- HTKPDYSCAPSXIR-UHFFFAOYSA-N octyltrimethylammonium ion Chemical compound CCCCCCCC[N+](C)(C)C HTKPDYSCAPSXIR-UHFFFAOYSA-N 0.000 description 1
- 239000005486 organic electrolyte Substances 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001690 polydopamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007784 solid electrolyte Substances 0.000 description 1
- RVKZDIDATLDTNR-UHFFFAOYSA-N sulfanylideneeuropium Chemical compound [Eu]=S RVKZDIDATLDTNR-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- NVAJXJBNBBWMHL-UHFFFAOYSA-N triethyl(methoxymethyl)phosphanium Chemical compound CC[P+](CC)(CC)COC NVAJXJBNBBWMHL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- VUOALROPAIMXGN-UHFFFAOYSA-N trimethyl(2-propoxyethyl)azanium Chemical compound CCCOCC[N+](C)(C)C VUOALROPAIMXGN-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
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- 238000004832 voltammetry Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0566—Liquid materials
- H01M10/0568—Liquid materials characterised by the solutes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/122—Ionic conductors
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0566—Liquid materials
- H01M10/0569—Liquid materials characterised by the solvents
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2300/00—Electrolytes
- H01M2300/0017—Non-aqueous electrolytes
- H01M2300/0025—Organic electrolyte
- H01M2300/0045—Room temperature molten salts comprising at least one organic ion
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Secondary Cells (AREA)
Description
なお、本発明におけるイオン液体とは、室温付近の一定温度において液体を保持するカチオン及びアニオンを含むイオン性物質のことを表す。なお、本発明において、室温とは通常25℃の温度を意味することとする。
(ここで、Xはハロゲン原子、nは1〜6の整数である。)
かくして本発明のイオン液体(A)及び電解質塩(B)を含む電解質が得られる。
本発明では、上記で得られる本発明の電解質を正極と負極との間に挟持してリチウム二次電池を製造する。
尚、例中「部」、「%」とあるのは、断りのない限り重量基準を意味する。
各特性の測定条件は以下の通りである。
TAインスツルメンツ製、「D2920型DSC」を用い、イオン液体を液体専用パンに封入後、窒素雰囲気下、−150℃に冷却し、−150℃より300℃まで10℃/分で昇温して測定した。更に、この手法で融点が−30℃未満のイオン液体に関しては、−30℃で24時間放置し、固化しないことを確認した。
25℃より300℃まで10℃/分でイオン液体を昇温して測定した。
JIS K 2265(―1,2,3,4)に準じて測定した。
パーキンエルマー社製「DSC 7」を用い、JIS K 0129に準じて測定した。イオン液体を、アルゴン雰囲気下で密閉型耐圧パンに封入後、窒素雰囲気下、50℃から350℃まで5℃/分で昇温して総発熱量を測定し、測定値をイオン液体の重量で除することにより、イオン液体1gあたりの発熱量とした。
測定用セルとして東亜DKK社製、CG−511B型セルを用いて、イオン液体に5時間浸漬後、電気化学測定システム「ソーラートロン1280Z」(英国ソーラートロン社製)を用い、交流インピーダンス法で測定した。交流振幅は5mV、周波数範囲は20k〜0.1Hzで測定した。
測定用セルとしてビーエーエス社製 V−4Cボルタンメトリー用セルを用い、電極はビーエーエス社製のものを用いた。作用極にはグラッシーカーボン(直径1mm)、対極は白金、参照電極にはリチウムを用いた。電位掃引速度は5mV/sec、温度は25℃で実施した。測定装置は電気化学測定システム「ソーラートロン1280Z」(英国ソーラートロン社製)を用いた。限界電流密度を±1mA/cm2とし、+1mA/cm2に到達する電位を酸化電位、−1mA/cm2に到達する電位を還元電位とし、酸化電位と還元電位の差を電位窓(V)とした。
計測器センター製の充放電測定装置を用いて、0.2mA/cm2の電流密度で4.2Vまで充電し、10分間の休止後、0.2mA/cm2の電流密度で3Vまで放電し、25℃でこの充放電を繰り返して、100サイクル目の充放電容量維持率(%)を測定した。
〔イオン液体(A−1)の製造〕
アルゴン気流下、300mLのエレンマイヤーに、五塩化リン36.4g、脱水アセトニトリル158mL、1−ブチル−3−メチルイミダゾリウム・クロライド30.6gを入れ、1時間撹拌した。得られた溶液を、シアン化銀72.3g、脱水アセトニトリル142mLが入った1L三つ口丸底フラスコに加え入れ、1日撹拌した後、ろ過し、ろ液を濃縮した。濃縮液にジクロロメタン100mLを加え、水50mLで3回洗浄した。その後、ジクロロメタン層を分取し濃縮することで、イオン液体(A−1)を41.5g得た。
IR 2186cm-1[CN]
31P−NMR −338.09ppm[P]
1H−NMR 9.09ppm[s,1H]
7.73ppm[d,Hz=1.5Hz,1H]
7.65ppm[d,Hz=1.5Hz,1H]
4.13ppm[t,Hz=7.2Hz,2H]
3.82ppm[s,3H]
1.74ppm[quint,Hz=7.2Hz,2H]
1.24ppm[sextet,Hz=7.2Hz,2H]
0.88ppm[t,Hz=7.2,3H]
〔イオン液体(A−2)の製造〕
アルゴン気流下、200mLのエレンマイヤーに、五塩化リン31.7g、脱水アセトニトリル100mL、1−ブチル−2,3−ジメチルイミダゾリウム・クロライド30.6gを入れ、1時間撹拌した。得られた溶液を、シアン化銀60.9g、脱水アセトニトリル60mLが入った300mL三つ口丸底フラスコに加え入れ、1日撹拌した後、ろ過し、ろ液を濃縮した。濃縮液にジクロロメタン100mLを加え、水50mLで3回洗浄した。その後、ジクロロメタン層を分取し濃縮することで、イオン液体(A−2)を32.6g得た。
イオン液体(A−2)の諸特性は表1に示されるとおりである。低温においても高いイオン伝導度と、広い電位窓を有することより電気化学特性に優れていることが確認された。
IR 2184cm-1[CN]
31P−NMR −338.09ppm[P]
1H−NMR 7.61ppm[d,Hz=2.4Hz,1H]
7.58ppm[d,Hz=2.1Hz,1H]
4.08ppm[t,Hz=7.3Hz,2H]
3.72ppm[s,3H]
2.56ppm[s,3H]
1.67ppm[quint,Hz=7.2Hz,2H]
1.27ppm[sextet,Hz=7.2Hz,2H]
0.89ppm[t,Hz=7.3,3H]
〔イオン液体(A−3)の製造〕
アルゴン気流下、200mLエレンマイヤーに、実施例2で製造した1−ブチル−3−メチルイミダゾリウム・トリクロロトリシアノホスフェイト22.4g、脱水アセトニトリル100mLを入れ溶解させた。その溶液を、AgBF473.4g、脱水アセトニトリル250mLの入った500mLエレンマイヤーに加え入れ、4日間撹拌した後、ろ過し、ろ液を濃縮した。濃縮液にジクロロメタン200mLを加え、水100mLで4回洗浄した。その後、ジクロロメタン層を抽出後、真空乾燥することによりイオン液体(A−3)を10.3g得た。
イオン液体(A−3)の諸特性は表1に示されるとおりである。低温においても高いイオン伝導度と、広い電位窓を有することより電気化学特性に優れていることが確認された。
IR 2199cm-1[CN]
31P−NMR ―227.09ppm[q,Hz=739.6Hz,P]
1H−NMR 8.42ppm[s,1H]
7.35ppm[d,Hz=1.5Hz,1H]
7.32ppm[d,Hz=1.5Hz,1H]
4.09ppm[t,Hz=7.5Hz,2H]
3.79ppm[s,3H]
1.76ppm[quint,Hz=7.5Hz,2H]
1.27ppm[sextet,Hz=7.2Hz,2H]
0.89ppm[t,Hz=7.5Hz,3H]
〔イオン液体(A−4)の製造〕
アルゴン気流下、300mL丸底フラスコに、五塩化リン41.7g、脱水アセトニトリル140mL、1−エチル−3−メチルイミダゾリウム・クロライド29.5gを入れ、1時間撹拌した。得られた溶液を、シアン化銀81.7g、脱水アセトニトリル150mLが入った500mL二つ口丸底フラスコに加え入れ、1日撹拌した後、ろ過し、ろ液を濃縮した。濃縮液にジクロロメタン100mLを加え、水50mLで3回洗浄した。その後、ジクロロメタン層を分取し濃縮することで、1−エチル−3−メチルイミダゾリウム・トリクロロトリシアノホスフェイトのイオン液体を41.4g得た。
次に、アルゴン気流下、500mLエレンマイヤーに、上記で製造した1−エチル−3−メチルイミダゾリウム・トリクロロトリシアノホスフェイト38.8gと脱水アセトニトリル70mLを入れ溶解させた。その溶液を、フッ素化剤であるAgBF4146gと脱水アセトニトリル500mLの入った1Lエレンマイヤーに加え入れ、60℃で5時間撹拌した後、更に、金属カチオン捕集剤として1−エチル−3−メチルイミダゾリウムクロライド56gを脱水アセトニトリル40mLに溶解させた溶液を加え、25℃で30分攪拌した。反応後、反応液をろ過し、ろ液を濃縮した。濃縮液をジクロロメタン200mLに溶解させ、100mLの水で4回水洗した。ジクロロメタン層を抽出後、真空乾燥することによりイオン液体(A−4)を16.6g得た。
イオン液体(A−4)の諸特性は表1に示されるとおりである。低温においても高いイオン伝導度と、広い電位窓を有することより電気化学特性に優れていることが確認された。
IR 2200cm-1[CN]
31P−NMR −227.06ppm[q,Hz=739.6Hz,P]
1H−NMR 8.35ppm[s,1H]
7.34ppm[s,1H]
7.29ppm[s,1H]
4.15ppm[q,Hz=7.2Hz,2H]
3.78ppm[s,3H]
1.42ppm[t,Hz=7.2,3H]
実施例1において、イオン液体(A−1)を、1−エチル−3−メチルイミダゾリウム・ビス(トリフルオロメタンスルホニル)アミドに変更した以外は同様にして評価した。
結果は表1に示されるとおりである。
実施例1において、イオン液体(A−1)を、1−エチル−3−メチルイミダゾリウム・ビス(フルオロスルホニル)アミドに変更した以外は同様にして評価した。
結果は表1に示されるとおりである。
一般的な有機電解液であるエチレンカーボネート(50体積%)/ジメチルカーボネート(50体積%)を用いて、実施例1と同様にして評価した。
結果は表1に示されるとおりである。
〔電解質の調製〕
実施例3で製造したイオン液体(A−3)8gに、電解質塩(B)としてLiN(SO2CF3)22gを混合溶解して、電解質[I]を得た。得られた電解質[I]の25℃における導電率は2mS/cmであった。
(1)正極の作製
LiCoO2粉末9.0g、ケチェンブラック0.5g、ポリフッ化ビニリデン0.5gを混合し、更に1−メチル−2−ピロリドン7.0gを添加して乳鉢でよく混合し、正極スラリーを得た。得られた正極スラリーをワイヤーバーを用いて厚さ20μmアルミニウム箔上に大気中で塗布し、100℃で15分間乾燥させた後、更に、減圧下130℃で1時間乾燥して、膜厚30μmの複合正極を作製した。
(2)電池の組立
電解質[I]を、セパレーター(セルガード社製セルガード#2400、厚さ20μm)と複合正極に含浸させた後、複合正極の上にセパレーター、負極としてのリチウム箔(厚さ500μm)の順で重ね、2032型コインセルに挿入し封缶し、リチウム二次電池を得た。
得られたリチウム二次電池の充放電特性を測定した結果、容量維持率は85%以上であり、この電池は良好な充放電容量維持率を有していた。
〔電解質の調製〕
実施例4で製造したイオン液体(A−4)8gに、電解質塩(B)としてLiN(SO2CF3)22gを混合溶解して、電解質[II]を得た。得られた電解質[II]の25℃における導電率は6mS/cmであった。
実施例6において、電解質[I]を電解質[II]に変更した以外は同様に行い、リチウム二次電池を得た。
得られたリチウム二次電池の充放電特性を測定した結果、容量維持率は85%以上であり、この電池は良好な充放電容量維持率を有していた。
Claims (10)
- 下記一般式(1)で示されるシアノホスフェイト系アニオンを有するイオン液体(A)、及び電解質塩(B)を含む電解質であり、リチウム二次電池に用いられる電解質。
- 一般式(1)におけるnが3〜5である請求項1記載の電解質。
- 一般式(1)におけるXがフッ素原子である請求項1または2記載の電解質。
- シアノホスフェイト系アニオンを有するイオン液体(A)が、含窒素系有機カチオンを有するイオン液体である請求項1〜3いずれか記載の電解質。
- 含窒素系有機カチオンが、イミダゾリウム系カチオンである請求項4記載の電解質。
- シアノホスフェイト系アニオンを有するイオン液体(A)が、有機または無機カチオンのハロゲン化物とハロゲン化リンを反応させて得られるハロゲン
化ホスフェイト系アニオンをシアノ化することにより製造されるイオン液体である請求項1〜5いずれか記
載の電解質。 - シアノホスフェイト系アニオンを有するイオン液体(A)が、有機または無機カチオンのハロゲン化物とハロゲン化リンを反応させて得られるハロゲン化ホスフェイト系アニオンをシアノ化した後に、更に該シアノ化物をフッ素化す
ることにより製造され、一般式(1)におけるXがフッ素原子のイオン液体である請求項6記載の電解質。 - シアノホスフェイト系アニオンを有するイオン液体(A)が、リチウム二次電池の電解質材料として用いられる際に、正極材料表面及び負極材料表面の少なくとも一つに対して電極保護膜形成機能を有するものである請求項1〜7いずれか記載の電解質。
- シアノホスフェイト系アニオンを有するイオン液体(A)における−30℃でのイオン伝導度が0.0001mS/cm以上である請求項1〜8いずれか
記載の電解質。 - 請求項1〜9いずれか記載の電解質、正極及び負極を含み、該電解質を、正極と負極との
間に挟持してなるリチウム二次電池。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2010060527A JP5511452B2 (ja) | 2009-03-18 | 2010-03-17 | 電解質及びそれを用いたリチウム二次電池 |
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2009065665 | 2009-03-18 | ||
JP2009065665 | 2009-03-18 | ||
JP2009265360 | 2009-11-20 | ||
JP2009265360 | 2009-11-20 | ||
JP2010060527A JP5511452B2 (ja) | 2009-03-18 | 2010-03-17 | 電解質及びそれを用いたリチウム二次電池 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2011126860A JP2011126860A (ja) | 2011-06-30 |
JP5511452B2 true JP5511452B2 (ja) | 2014-06-04 |
Family
ID=42739694
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010060527A Expired - Fee Related JP5511452B2 (ja) | 2009-03-18 | 2010-03-17 | 電解質及びそれを用いたリチウム二次電池 |
Country Status (6)
Country | Link |
---|---|
US (1) | US20110311865A1 (ja) |
EP (1) | EP2410601A4 (ja) |
JP (1) | JP5511452B2 (ja) |
KR (1) | KR20120004970A (ja) |
CN (1) | CN102356500A (ja) |
WO (1) | WO2010107034A1 (ja) |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012009158A (ja) * | 2010-06-22 | 2012-01-12 | Nippon Synthetic Chem Ind Co Ltd:The | 電解質及びそれを用いたリチウム二次電池 |
JP4917178B2 (ja) * | 2010-06-22 | 2012-04-18 | 日本合成化学工業株式会社 | 電解質材料、リチウム二次電池用電解質、及び、それを用いたリチウム二次電池、並びに新規なリチウム塩 |
JP5614807B2 (ja) * | 2010-12-16 | 2014-10-29 | 日本化学工業株式会社 | 光電変換素子用電解質組成物及び光電変換素子 |
CN103688400A (zh) * | 2011-04-27 | 2014-03-26 | 联邦科学与工业研究组织 | 锂储能装置 |
JP5701153B2 (ja) * | 2011-05-31 | 2015-04-15 | 日本合成化学工業株式会社 | 二次電池用電解質、及び二次電池 |
US9214707B2 (en) * | 2012-09-21 | 2015-12-15 | Robert Bosch Gmbh | Metal/oxygen battery with precipitation zone |
KR101754606B1 (ko) | 2012-11-13 | 2017-07-07 | 삼성에스디아이 주식회사 | 전해액 첨가제, 전해액 및 리튬 이차 전지 |
KR101754608B1 (ko) | 2013-02-27 | 2017-07-07 | 삼성에스디아이 주식회사 | 리튬 이차 전지용 전해액 및 이를 포함하는 리튬 이차 전지 |
WO2014167035A1 (en) * | 2013-04-12 | 2014-10-16 | Lonza Ltd | Method for preparation of fluoro and chloro cyano compounds of the 15th group |
WO2015067404A1 (en) * | 2013-11-11 | 2015-05-14 | Lonza Ltd | Method for preparation of fluoro cyano compounds of the 15th group with a lewis acid |
JP6305202B2 (ja) * | 2014-05-16 | 2018-04-04 | キヤノン株式会社 | 電子写真用部材、プロセスカートリッジ及び電子写真装置 |
JP6592891B2 (ja) * | 2014-12-22 | 2019-10-23 | 日清紡ホールディングス株式会社 | 二次電池用電解液および二次電池 |
US10707526B2 (en) | 2015-03-27 | 2020-07-07 | New Dominion Enterprises Inc. | All-inorganic solvents for electrolytes |
EP3078668A1 (en) | 2015-04-09 | 2016-10-12 | Lonza Ltd | Method for preparation of fluoro cyano compounds of the 15th group with a bronstedt acid |
US10573933B2 (en) * | 2015-05-15 | 2020-02-25 | Samsung Electronics Co., Ltd. | Lithium metal battery |
US10707531B1 (en) | 2016-09-27 | 2020-07-07 | New Dominion Enterprises Inc. | All-inorganic solvents for electrolytes |
US10505219B2 (en) * | 2017-05-26 | 2019-12-10 | Toyota Motor Engineering & Manufacturing North America, Inc. | Artificial SEI transplantation |
PL3503268T3 (pl) * | 2017-12-22 | 2021-04-06 | Belenos Clean Power Holding Ag | Formulacja ciekłego elektrolitu dla litowo-metalowej baterii akumulatorowej i zawierająca ją litowo-metalowa bateria akumulatorowa |
CN108336412B (zh) * | 2018-01-16 | 2021-02-26 | 深圳大学 | 一种锂离子电池电解质及其制备方法与锂离子电池 |
CN114791454B (zh) * | 2021-01-26 | 2024-05-10 | 清华大学 | 电解质氧化电势的测量装置及其测量方法 |
CN113991201B (zh) * | 2021-10-27 | 2024-01-30 | 远景动力技术(江苏)有限公司 | 气体吸附隔膜、其制备方法及锂离子电池 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050164082A1 (en) * | 2004-01-27 | 2005-07-28 | Takashi Kishi | Nonaqueous electrolyte battery |
JP2005243620A (ja) * | 2004-01-27 | 2005-09-08 | Toshiba Corp | 非水電解質電池 |
JP4515948B2 (ja) * | 2005-03-31 | 2010-08-04 | 株式会社東芝 | ゲル状電解質用原料キット、ゲル状電解質用電解質組成物及び光増感型太陽電池 |
JP2006344446A (ja) * | 2005-06-08 | 2006-12-21 | Nissan Motor Co Ltd | イオン伝導体及びエネルギーデバイス |
US7541492B2 (en) * | 2005-10-26 | 2009-06-02 | Toyota Jidosha Kabushiki Kaisha | Perfluoroalkanesulfonamide compounds |
CN101087035B (zh) * | 2006-06-06 | 2010-10-06 | 比亚迪股份有限公司 | 一种二次锂电池用电解液及含有该电解液的二次锂电池 |
JP4199282B2 (ja) * | 2007-05-14 | 2008-12-17 | 株式会社東芝 | 非水電解質二次電池 |
JP4917178B2 (ja) * | 2010-06-22 | 2012-04-18 | 日本合成化学工業株式会社 | 電解質材料、リチウム二次電池用電解質、及び、それを用いたリチウム二次電池、並びに新規なリチウム塩 |
-
2010
- 2010-03-16 EP EP10753526.2A patent/EP2410601A4/en not_active Withdrawn
- 2010-03-16 WO PCT/JP2010/054462 patent/WO2010107034A1/ja active Application Filing
- 2010-03-16 CN CN2010800122259A patent/CN102356500A/zh active Pending
- 2010-03-16 US US13/254,080 patent/US20110311865A1/en not_active Abandoned
- 2010-03-16 KR KR1020117021716A patent/KR20120004970A/ko not_active Application Discontinuation
- 2010-03-17 JP JP2010060527A patent/JP5511452B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
US20110311865A1 (en) | 2011-12-22 |
JP2011126860A (ja) | 2011-06-30 |
CN102356500A (zh) | 2012-02-15 |
EP2410601A4 (en) | 2013-07-31 |
EP2410601A1 (en) | 2012-01-25 |
WO2010107034A1 (ja) | 2010-09-23 |
KR20120004970A (ko) | 2012-01-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5511452B2 (ja) | 電解質及びそれを用いたリチウム二次電池 | |
JP4917178B2 (ja) | 電解質材料、リチウム二次電池用電解質、及び、それを用いたリチウム二次電池、並びに新規なリチウム塩 | |
EP3436465B1 (en) | Modified ionic liquids containing phosphorus | |
US11038197B2 (en) | Aqueous and hybrid electrolytes with wide electrochemical stability windows | |
JP2012009158A (ja) | 電解質及びそれを用いたリチウム二次電池 | |
JP6849920B2 (ja) | 非水電解液電池用電解液及びそれを用いた非水電解液電池 | |
JP3722685B2 (ja) | 電気化学ディバイス用電解質及びそれを用いた電池 | |
JP5544748B2 (ja) | 電気化学ディバイス用電解質、これを用いる電解液および非水電解液電池 | |
Reiter et al. | N-Allyl-N-methylpiperidinium bis (trifluoromethanesulfonyl) imide—A film forming ionic liquid for graphite anode of Li-ion batteries | |
JP5950662B2 (ja) | イオン液体、電解質及びリチウム二次電池 | |
CN117438649A (zh) | 非水性电解质组合物 | |
JP5150954B2 (ja) | 電解質およびそれを用いたリチウム二次電池 | |
KR102631722B1 (ko) | 트리아진을 함유하는 변성 이온성 액체 | |
US20020122979A1 (en) | Fluoroalkylphosphate salts, and process for the preparation of these substances | |
JP5701153B2 (ja) | 二次電池用電解質、及び二次電池 | |
JP4811070B2 (ja) | 非水電解液電池用電解質、電解液及び非水電解液電池 | |
JP2010215512A (ja) | イオン液体、イオン液体の製造方法、電解質およびリチウム二次電池 | |
JP3730855B2 (ja) | 電気化学ディバイス用電解質、その電解液または固体電解質並びに電池 | |
JP5832370B2 (ja) | イオン液体 | |
JP3730860B2 (ja) | 電気化学ディバイス用電解質、その電解液または固体電解質並びに電池 | |
JP2013114934A (ja) | 金属塩、電極保護膜形成剤、それを用いた二次電池用電解質、及び二次電池 | |
JP2010235583A (ja) | イオン液体、電解質およびリチウム二次電池 | |
CN112585794A (zh) | 用于锂二次电池中的包含有机碳酸酯和环状亚砜的液体电解质 | |
JP6169265B2 (ja) | フタレートホスフィン系陰イオンを含む電解液、これを含む二次電池用添加剤およびこれを含む二次電池 | |
Wang et al. | Liquid Electrolytes |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20130225 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140212 |
|
A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140305 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20140325 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20140325 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5511452 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |