CN100413873C - 离子型液体ⅱ - Google Patents
离子型液体ⅱ Download PDFInfo
- Publication number
- CN100413873C CN100413873C CNB011228059A CN01122805A CN100413873C CN 100413873 C CN100413873 C CN 100413873C CN B011228059 A CNB011228059 A CN B011228059A CN 01122805 A CN01122805 A CN 01122805A CN 100413873 C CN100413873 C CN 100413873C
- Authority
- CN
- China
- Prior art keywords
- ionic liquid
- solvent
- equal
- less
- trifluorophosphate
- 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
- 239000007788 liquid Substances 0.000 title description 4
- 239000002608 ionic liquid Substances 0.000 claims abstract description 24
- -1 heterocyclic cation Chemical class 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 23
- 239000007983 Tris buffer Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- JFZKOODUSFUFIZ-UHFFFAOYSA-N trifluoro phosphate Chemical compound FOP(=O)(OF)OF JFZKOODUSFUFIZ-UHFFFAOYSA-N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 150000001450 anions Chemical class 0.000 claims description 10
- 150000001768 cations Chemical class 0.000 claims description 10
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910000552 LiCF3SO3 Inorganic materials 0.000 claims description 2
- 229910001290 LiPF6 Inorganic materials 0.000 claims description 2
- 239000012530 fluid Substances 0.000 claims description 2
- 229910001540 lithium hexafluoroarsenate(V) Inorganic materials 0.000 claims description 2
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 claims description 2
- 229910001486 lithium perchlorate Inorganic materials 0.000 claims description 2
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims 1
- QSZMZKBZAYQGRS-UHFFFAOYSA-N lithium;bis(trifluoromethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F QSZMZKBZAYQGRS-UHFFFAOYSA-N 0.000 claims 1
- 239000003990 capacitor Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 28
- 239000003792 electrolyte Substances 0.000 description 17
- 229910052744 lithium Inorganic materials 0.000 description 15
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 229910052731 fluorine Inorganic materials 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 10
- 229910019142 PO4 Inorganic materials 0.000 description 9
- 235000021317 phosphate Nutrition 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 8
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000010405 anode material Substances 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000003446 ligand Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- IBZJNLWLRUHZIX-UHFFFAOYSA-N 1-ethyl-3-methyl-2h-imidazole Chemical compound CCN1CN(C)C=C1 IBZJNLWLRUHZIX-UHFFFAOYSA-N 0.000 description 4
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 125000003226 pyrazolyl group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- MXLZUALXSYVAIV-UHFFFAOYSA-N 1,2-dimethyl-3-propylimidazol-1-ium Chemical compound CCCN1C=C[N+](C)=C1C MXLZUALXSYVAIV-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-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
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000001351 cycling effect Effects 0.000 description 2
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- 150000002222 fluorine compounds Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 description 1
- 229910013131 LiN Inorganic materials 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium chloride Substances Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- OJOSABWCUVCSTQ-UHFFFAOYSA-N cyclohepta-2,4,6-trienylium Chemical compound C1=CC=C[CH+]=C[CH]1 OJOSABWCUVCSTQ-UHFFFAOYSA-N 0.000 description 1
- 150000004862 dioxolanes Chemical class 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012025 fluorinating agent Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000009830 intercalation Methods 0.000 description 1
- 230000002687 intercalation Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 229940006487 lithium cation Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229960004011 methenamine Drugs 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 150000005677 organic carbonates Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
- 239000002341 toxic gas Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/06—Lead-acid accumulators
- H01M10/08—Selection of materials as electrolytes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/004—Details
- H01G9/022—Electrolytes; Absorbents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
-
- 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
- H01M10/0568—Liquid materials characterised by the solutes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/223—Five-membered rings containing nitrogen and carbon only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/223—Five-membered rings containing nitrogen and carbon only
- C10M2215/224—Imidazoles
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/063—Ammonium or amine salts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/077—Ionic Liquids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/14—Electric or magnetic purposes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M6/00—Primary cells; Manufacture thereof
- H01M6/14—Cells with non-aqueous electrolyte
- H01M6/16—Cells with non-aqueous electrolyte with organic electrolyte
- H01M6/162—Cells with non-aqueous electrolyte with organic electrolyte characterised by the electrolyte
- H01M6/164—Cells with non-aqueous electrolyte with organic electrolyte characterised by the electrolyte by the solvent
-
- 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)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Electrochemistry (AREA)
- Manufacturing & Machinery (AREA)
- Power Engineering (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Inorganic Chemistry (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Secondary Cells (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Electric Double-Layer Capacitors Or The Like (AREA)
Abstract
本发明涉及用于电化学电池和有机合成的离子型液体。
Description
本发明涉及用于电化学电池和有机合成中的离子型液体。
美国专利US 2446331中第一次描述了无溶剂的离子型液体或“在室温下熔化的盐类”。这些强路易斯酸存在的问题是与大气中的潮气接触易形成有毒气体。
人们对涉及AlCl3和1-乙基-3-甲基咪唑(EMI)氯化物的化合物进行了长期研究。Wilkes和Zaworotko于1992年发现了新型无溶剂的离子型液体,EMI BF4和EMI O2CCH3,见J.Chem.Soc.,Chem.Commun.,第965页。但是,这些化合物不适宜在电化学电池中用做电解质,因为BF4和CH3CO2阴离子甚至在相对低的电位下也易被氧化.
德国专利DE 196 41138中描述了一种新型导电盐,氟代烷基磷酸锂。这些盐具有十分突出的高电化学稳定性和低水解倾向。(M.Schmidt et al.10thInternational Meeting on Lithium Batteries,Como 2000)。在循环实验中,这些化合物显示特别好的结果,且被证明是特别稳定的。
美国专利US 5827602描述了离子型液体的用途,该组离子型液体选自包含吡啶,哒嗪,嘧啶,吡嗪,咪唑,吡唑,噻唑,噁唑,和三唑盐的一组,在电化学电池中含有亚氨盐和甲烷盐(Methanide)作为阴离子。这些离子型液体由于具有良好的导电性特别适合于这种用途。其重要的缺点在于原材料特别是阴离子的昂贵合成。
本发明的目的在于提供具有大的液体范围,高热稳定性,低腐蚀性及较低合成造价的阴离子的离子型液体。
本发明的目的通过通式为下式的离子型液体实现:
K+A-(I)
其中,K+为阳离子,选自:
其中R1到R5相同或不同,可选择地通过一单键或双键彼此直接键合,且每个单独或一起具有以下的意义:
-H,
-卤素,
-烷基(C1到C8),它可部分或全部被进一步的基团,优选F,Cl,N(CnF(2n+1-x)Hx)2,O(CnF(2n+1-x)Hx),SO2(CnF(2n+1-x)Hx)或CnF(2n+1-x)Hx取代,其中1<n<6且0<x≤2n+1
且A-为阴离子,选自:
[PFx(CyF2y+1-zHz)6-x]-
其中1≤x<6
1≤y≤8,以及
0≤z≤2y+1。
优选的是,本发明的目的是通过通式为下式的离子型液体实现:
K+A-(I)
其中:
K+为阳离子,选自:
其中R1到R5相同或不同,任意选择地通过一单键或双键彼此直接键合,且每个单独或一起具有以下的意义:
-H,
-卤素,
-具有1-8个碳原子的烷基基团,
且A-为选自如下的阴离子:
[PFx(CyF2y+1-zHz)6-x]-
其中1≤x<6
1≤y≤8
0≤z≤2y+1,
而且上述阴离子不包括[(CF3)2PF4]-、[(CF3)3PF3]-、[(CF3)4PF2]-、[(CF3)5PF]-和[(CF3)6P]-。
这些离子型液体适合作为有机合成的溶剂,但也可以用于电化学电池。另外,这些离子型液体还适合于用作有机反应的催化剂。另外,它们还适用于作为高反应活性的化学品的惰性溶剂。还可以用于液压液体领域。
已发现本发明化合物由于使用了全氟烷烃链,优选使用相对长链的全氟烷烃因而是疏水的。而且无水合成最大限度地减少了不希望带入反应体系的水分。
令人惊奇的发现离子型液体是不腐蚀的,但比通常用于电化学电池的铝电流集电器更钝化。这使得循环稳定性增加。另外,通过使用离子型液体可观察到体系的热稳定性的改善。
人们发现加入低粘度的溶剂可提高导电性。低粘度和高导电性是用于电化学电池的先决条件。本发明的化合物具有大的液体范围,使得它们特别适合这种应用。
用于双层电容器的先决条件是高导电性。本发明的化合物满足这一标准,因此可单独使用或以与其它溶剂或导电盐的混合物的形式使用。这些适合的溶剂选自有机碳酸酯(例如,碳酸亚乙酯,碳酸亚丙酯,及其衍生物,碳酸亚丁酯,碳酸二甲酯,碳酸二乙酯,碳酸乙基甲基酯,等),有机羧酸酯(例如,γ-丁内酯,甲酸甲酯,乙酸甲酯,乙酸乙酯,丙酸乙酯,丙酸甲酯,丁酸甲酯,丁酸乙酯,等),有机羧酸酰胺(例如,二甲基甲酰胺,甲基甲酰胺,甲酰胺等),有机醚(例如,1,2-二甲氧基乙烷,四氢呋喃,2-甲基四氢呋喃,四氢呋喃衍生物,1,3-二氧环戊烷,二氧杂环己烷,二氧杂环戊烷衍生物等)或其它对质子惰性的溶剂(例如乙腈,环丁砜。二甲亚砜。硝基甲烷,磷酸三酯,三甲氧基甲烷,3-甲基-2-噁唑烷二酮等)。同样的也可以使用溶剂的混合物,例如碳酸亚乙酯/碳酸二甲酯(ECIDMC)。
本发明的化合物可与常规导电性盐一起用于惯常的电解质中。它们可以1-99%存在于混合物中。适合的电解质的例子为带有选自如下的导电盐的电解质:LiPF6,LiBF4,LiClO4,LiAsF6,LiCF3SO3,LiN(CF3SO2)2和LiC(CF3SO2)3及其混合物。
该电解质也包含有机异氰酸酯(DE 199 44 603)以减少水含量。
也提供了通式(DE 199 51 804)如下的复合盐:
Mx+[EZ]y- x/y
其中:
x和y为1,2或3,
Mx+为金属离子,
E为一种Lewis酸,选自:
BR1R2R3,AlR1R2R3,PR1R2R3R4R5,AsR1R2R3R4R5和VR1R2R3R4R5
R1到R5可相同或不同,可选择地直接与另一个基团通过一单键或双键键合,且每个单独或一起为:
卤素(F,Cl或Br),
烷基或烷氧基(C1到C8),它们可被部分或全部被F,Cl或Br取代,
芳香环,任意选择地通过氧键合,选自:苯基,萘基,蒽基和菲基,这些基团可以是来取代的,或被烷基(C1至C8)或F,Cl或Br单取代到多取代,
芳香杂环,任意选择地通过氧键合,选自:吡啶基,吡唑基和嘧啶基,这些基团可以是未取代的,或被烷基(C1至C8)或F,Cl或Br单取代到多取代,
Z为OR6,NR6R7,CR6R7R8,OSO2R6,N(SO2R6)(SO2R7),C(SO2R6)-(SO2R7)(SO2R8)或OCOR6,其中
R6到R8相同或不同,可选择地直接与另一个基团通过一单键或双键键合,且每个单独或一起为:
氢或如R1到R5的定义,
通过相应的硼或磷Lewis酸/溶剂加合物与亚氨化锂或四烷基铵,methanide或三氟甲磺酸盐反应制备。
也提供了通式如下的硼酸盐(DE 199 59 722):
其中:
M为金属离子或四烷基铵离子,
x和y为1,2或3,
R1到R4相同或不同,为烷氧基或羧基(C1-C8),它们任意选择地直接与另外的基团通过单键或双键键合。这些硼酸盐可如下制备,使四烷氧基硼酸锂或烷氧基锂与硼酸的1∶1混合物,与适合的羟基或羧基化合物在对质子惰性的溶剂中按2∶1或4∶1的比例反应
也可以存在添加剂,例如通式如下的硅烷化合物:
SiR1R2R3R4
其中R1到R4为
H
CyF2y+1-zHz
OC(O)CyF2y+1-zHz
OSO2CyF2y+1-zHz
且1<x<6
1<y<8
0<z<2y+1
R1-R4可相同或不同,为选自苯基和萘基的芳香环,而苯基或萘基可以是非取代的或被下面基团单取代或多取代:F,CyF2y+1-zHz,OCyF2y+1-zHz,OC(O)CyF2y+1-zHz,OSO2CyF2y+1-zHz或N(CyF2y+1-zHz)2,或为选自吡啶基,吡唑基,或嘧啶基的杂芳环,该这些基团中的每一个可被下面基团单取代或多取代:F,CyF2y+1- zHz,OCyF2y+1-zHz,OC(O)CyF2y+1-zHz,OSO2 CyF2y+1-zHz或N(CyF2y+1-zHz)2(DE 100 27626)。
本发明的化合物也可以用于含有下式表示的氟烷基磷酸锂电解质:
Li+[PFx(CyF2y+1-zHz)6-x]-
其中1≤x≤5
3≤y≤8
0≤z≤2y+1
配体(CyF2y+1-zHz)可以相同或不同,只是以下通式化合物除外:
Li+[PFa(CHbFC(CF3)d)c]-
其中,a为2-5的整数,b=0或1,c=0或1,d=2,e为1-4的整数,前提是b和c不能同时分别为0,且a+e的和等于6,配体(CHbFC(CF3)d)可以相同或不同(DE 100 089 55)。
制备氟烷基磷酸锂的方法,其特征在于至少一种通式为下式的化合物:
HmP(CnH2n+1)3-m,
OP(CnH2n+1)3,
ClmP(CnH2n+1)3-m,
FmP(CnH2n+1)3-m,
CloP(CnH2n+1)5-o,
FoP(CnH2n+1)5-o,
其中,0<m<2,1<n<8且0<o<4,
通过在氟化氢中电解氟化,得到的氟化产物的混合物通过提取,相分离和/或蒸馏加以分离,得到的氟化的烷基膦(phosphorane)在质子惰性的溶剂混合物中,在除去水分的条件下与氟化锂反应,得到的盐提纯并用常规方法分离。
本发明的化合物也可以用于含有下式的盐的电解质:
Li[P(OR1)a(OR2)b(OR3)c(OR4)dFe]
其中0<a+b+c+d≤5且a+b+c+d+e=6,R1到R4,各自独立的为烷基,芳基或杂芳基基团,其中R1到R4至少两个可与另外一个通过单键或双键直接键合(DE 100 16 801)。该化合物可通过下面制备:将通式如下的磷(V)化合物:
Li[P(OR1)a(OR2)b(OR3)c(OR4)dFe]
其中0<a+b+c+d≤5且a+b+c+d+e=5,R1到R4的定义如上,与氟化锂在有机溶剂存在下反应。
电解质中也可存在下面通式的离子型液体:
K+A-
其中,K+为选自如下的阳离子:
其中R1到R5相同或不同,可选择地直接与另一个基团通过一单键或双键键合,且每个单独或一起具有以下的意义:
-H,
-卤素,
-烷基(C1到C8),可被部分或全部被进一步的下列基团取代:F,Cl,N(CnF(2n+1-x)HX)2,O(CnF(2n+1-x)HX),SO2(CnF(2n+1-X)HX)或CnF(2n+1-X)HX,其中1<n<6且0<x≤2n+1
且A-为选自如下的阴离子:
[B(OR1)n(OR2)m(OR3)o(OR4)p]-
其中0<n,m,o,p≤4,且
m+n+o+p=4,
其中,R1到R4不同或成对的相同,可选择地直接与另一个基团通过一单键或双键键合,且每个单独或一起为:
芳环,选自:苯基,萘基,蒽基和菲基,这些基团可以是未取代的,或被下列基团单取代到多取代;CnF(2n+1-x)HX,其中1<n<6且0<x≤13,或卤素(F,Cl或Br),
芳杂环,选自:吡啶基,吡唑基和嘧啶基,这些基团可以是未取代的,或被下列基团单取代到多取代;CnF(2n+1-x)HX,其中1<n<6且0<x≤13,或卤素(F,Cl或Br),
烷基(C1到C8),可部分或全部被进一步的基团、优选F,Cl,N(CnF(2n+1-x)HX)2,O(CnF(2n+1-x)HX),SO2(CnF(2n+1-x)HX或CnF(2n+1-x)HX,其中1<n<6和0<x≤13,取代
或OR1到OR4
单独或一起为芳香或脂肪羧基,二羧基,氧代磺酰基,或氧代羰基基团,这些基团可部分或全部被进一步的基团、优选F,Cl,N(CnF(2n+1-x)HX)2,O(CnF(2n+1-x)HX),SO2(CnF(2n+1-x)HX)或CnF(2n+1-x)HX,其中1<n<6和0<x≤13取代(DE 10026565)。
根据本发明的化合物也可以用在包含下面通式的化合物的电解质中:
NR1R2R3
其中,R1和R2为H,CyF(2y+1-z)Hz或(CnF2n-mHm)X,其中X为芳香的或杂环的基团,
R3为(CnF2n-mHm)Y,其中Y为杂环基团,或(CoF2o-pHp)Z,其中Z为芳香基团,
且其中n,m,o,p,y和z满足下列条件:
0≤n≤6
0≤m≤2n
2≤o≤6
0≤p≤2o,
1≤y≤8且
0≤z≤2y+1,
用于在电化学电池中减少对质子惰性的电解质体系的酸含量。
也可以使用通式如下的氟烷基磷酸盐:
Mn+[PFx(CyF2y+1-zHz)6-x]-
其中:
1≤x≤6
1≤y≤8
0≤z≤2y+1
1≤n≤3,且
Mn+为单价或三价阳离子,特别是:
NR1R2R3R4,
PR1R2R3R4,
P(NR1R2)kR3 mR4 4-k-m(基中k=1-4,m=0-3且k+m≤4),
C(NR1R2)(NR3R4)(NR5R6),
C(烷基)3,Rb或托品基(tropylium),
其中R1到R8为H,烷基或芳基(C1-C8),可被F,Cl或Br部分取代,
其中,排除Mn+=Li+,Na+,Cs+,K+和Ag+的情况。这些氟烷基磷酸盐通过将正磷与氟化物,或金属氟烷基磷酸盐与氟化物或氯化物在有机非质子溶剂中反应得到(DE 100 388 58)。
电解质也可以包含下面的混合物:
a)至少一种下面通式的氟烷基磷酸锂:
Li+[PFx(CyF2y+1-zHz)6-x]-
其中:
1≤x≤5
1≤y≤8且
0≤z≤2y+1
在每中情况下配体CyF2y+1-zHz可相同或不同,及
b)至少一种聚合物(DE 100 58 264)。
电解质还可以包括下面通式的四氟烷基硼酸盐:
Mn+([BR4]-)n
其中,Mn+为单价,二价或三价阳离子,
在每种情况下配体R相同,为(CxF2x+1),其中1≤x≤8,且n=1,2或3(DE100 558 11)。制备四氟烷基硼酸盐的方法,其特征在于至少有一种通式为Mn+([B(CN)4]-)n的化合物,其中Mn+和n的定义如上,通过与至少一种氟化试剂在至少一种溶剂中氟化,得到的被氟化的化合物通过常规方法提纯和分离。
电解质还可以包括下面通式的硼酸盐:
Mn+[BFx(CyF2y+1-zHz)4-x]n -
其中
1<x<3,1≤y≤8且0≤z≤2y+1,
M为除了钾和钡之外的单价到三价阳离子(1≤n≤3),
特别是:
Li,
NR1R2R3R4,PR5R6R7R8,P(NR5R6)kR7 mR8 4k-m(其中k=1-4,m=0-3且k+m≤4),或
C(NR5R6)(NR7R8)(NR9R10),其中
R1到R4为CyF2y+1-zHz且
R5到R10为H或CyF2y+1-zHz,或
芳香杂环阳离子,优选含氮和/或氧和/或硫的芳香杂环阳离子(DE 101 03189)。制备这些化合物的特征在于:
a)1∶1的BF3/溶剂复合物与烷基锂在冷却下反应,缓慢升温下除去大部分的溶剂,而后过滤得到的固体,用适当的溶剂洗涤,
b)在适当的溶剂中锂盐与B(CF3)F3盐1∶1的反应,混合物升温搅拌,除去溶剂,向反应混合物中加入非质子非水溶剂,优选那些用于电化学电池中的溶剂,将反应混合物干燥,或
c)B(CF3)F3盐与锂盐按1∶1到1∶1.5的比例在水中在升温下反应,在沸点下加热0.5到2小时,除去水,向反应混合物中加入非质子非水溶剂,优选那些用于电化学电池中的溶剂,将反应混合物干燥。
电解质也可以包含下面通式的氟烷基磷酸盐:
Mn+[PFx(CyF2y+1-zHz)6-x]n -
Mn+为单价,二价或三价阳离子,
1≤x≤5
1≤y≤8且
0≤z≤2y+1,n=1,2或3,在每种情况下配体(CyF2y+1-zHz)可以相同或不同,其中氟烷基磷酸盐中
Mn+为锂阳离子,且盐
M+([PF4(CF3)2]-)中M+=Cs+,Ag+或K+
M+([PF4(C2F5)2]-)中M+=Cs+
M+([PF3(C2F5)3]-)中M+=Cs+,K+,Na+或对-Cl(C6H4)N2 +,
M+([PF3(C3F7)3]-)中M+=Cs+,K+,Na+,对-Cl(C6H4)N2 +或对-O2N(C6H4)N2 +,被排除(DE 100 558 12)。制备这些氟烷基磷酸盐的特征在于:至少一种下面通式的化合物:
HrP(CsH2s+1)3-r,
OP(CsH2s+1)3,
ClrP(CsH2s+1)3-r,
FrP(CsH2s+1)3-r,
CltP(CsH2s+1)5-t和/或
FtP(CsH2s+1)5-t
其中,在每种情况下:
0≤r≤2
3≤s≤8且
0≤t≤4,
通过在氟化氢中电解被氟化,得到的氟化产物混合物分离,将得到的氟化的烷基磷酸在非质子溶剂或在除去水分的溶剂的混合物中与下面的通式的化合物反应:
Mn+(F-)n,其中Mn+和n如上述所定义,
得到的氟烷基磷酸盐通过常规方法提纯和分离。
本发明的化合物也可以用于含有下式的氟烷基磷酸盐(DE 10109032)电解质中:
(Ma+)b[(CnF2n+1-mHm)yPF5-y(CR1R2)xPF5-y(CnF2n+1-mHm)y](2-) (a+b/2)
其中,
Ma+为单价,二价或三价阳离子,
a=1,2或3,b=2对应于a=1,b=2对应于a=3,b=1对应于a=2,且在每种情况下:
1≤n≤8,
0≤m≤2对应于n=1或2,
0≤m≤4对应于3≤n≤8
1≤x≤12,
0≤y≤2
其中在每种情况下R1和R2相同或不同,选自:氟,氢,烷基,氟烷基和全氟烷基取代基,且
在其中每种情况下,取代基(CnF2n+1-mHm)相同或不同。这些化合物如下制备:将至少一种氟-α,ω-双(烷基氟代磷酰)烷烃与至少一种通式为(Ma+)[F-]a,其中(Ma+)和a的定义同上的氟盐在溶液中反应,得到氟烷基磷酸盐,并在必要时用常规方法对后者加以提纯和/或分离。
本发明的化合物可用于下面的电化学电池的电解质,其阳极材料由涂覆的金属核构成。金属选自Sb,Bi,Cd,In,Pb,Ga和锡或它们的合金(DE 100 16 024)。制备这种阳极材料的方法的特征在于:
a)制备一种金属或合金核在乌洛脱品中的悬浊液或溶液,
b)将该悬浊液在的C5-C12-烷烃中乳化,
c)将乳化液沉淀在金属或合金核上,
d)通过加热体系将金属氧化物或过氧化物转化为相应的氧化物。
本发明的化合物还可用于下面的电化学电池的电解质,其阴极材料由通常的锂嵌入或插入化合物制成。阴极材料也可以由用一种或多种金属氧化物涂覆的混合金属氧化物锂颗粒构成(DE 199 22 522)。它们也可以由用一种或多种聚合物涂覆的混合金属氧化物锂颗粒构成(DE 199 46 066)。本发明的化合物同样可以用于下面的阴极体系,其阴极由用一种或多种碱金属化合物和金属氧化物涂覆的混合金属锂颗粒构成(DE 100 14 884)。制备这些材料的特征在于:将颗粒悬浮于有机溶剂中,加入悬浮于有机溶剂中的碱金属盐化合物,加入溶于有机溶剂的金属氧化物,向悬浊液中加入水解溶液,随后过滤被涂覆的颗粒,干燥并煅烧。本发明的化合物也可以用于含有浸渍了氧化锡的阳极材料的体系(DE 100 25761)。这些阳极材料可按下面方法制备:
a)向氯化锡溶液中加入尿素,
b)向溶液中加入乌洛脱品和适宜的浸渍化合物,
c)得到的溶液在石油醚中乳化,
d)洗涤得到的凝胶,抽滤除去溶剂,
e)干燥并加热该凝胶。
本发明的化合物还可以用于含有用还原的锡氧化物制成的阳极材料的体系(DE 100 257 62)。阳极材料如下制备:
a)向氯化锡溶液中加入尿素,
b)向溶液中加入乌洛脱品,
c)得到的溶液在石油醚中乳化,
d)洗涤得到的凝胶,抽滤除去溶剂,
e)干燥并加热该凝胶。
f)将得到的SnO2暴露在一可通空气的反应炉中暴露在还原气蒸汽中。
下面将对本发明的一般实施例加以详细解释。
阴离子选自由下式构成的一组:
[PFx(CyF2y+1-zHz)6-x]-
其中1≤x≤6
1≤y≤8且
0≤z≤2y+1
按照DE 196 411 38所使用的方法制备。
阳离子选自下面构成的一组:
由已知的US 5827602中的方法制备。将起始原料在对质子惰性的有机溶剂中,在溶剂为液体范围的温度下反应0.5到12小时,优选1-4小时。
为除去副产物,将混合物冷却至-30℃,例如在LiCl为副产物的情况下,冷却至-10℃到-20℃,将沉淀的副产物过滤除去,优选在真空下过滤。
溶剂/产物的混合物可以直接用于电解质中。在必要时,可蒸馏除去溶剂,将得到的产物干燥以用于所述是用途。
下面的实施例旨在对本发明加以详细说明,但不限制发明。
实施例:
实施例1
三(五氟乙基)三氟磷酸1-乙基-3-甲基咪唑鎓的合成
三(五氟乙基)三氟磷酸锂按照DE 196411 38的方法合成。产物在乙腈中按照下面反应式进行反应:
反应混合物在冷却下用玻璃漏斗真空过滤,以除去所形成的LiCl副产物。在减压下蒸馏除去溶剂,得到的三(五氟乙基)三氟磷酸1-乙基-3-甲基咪唑鎓在减压下干燥。
实施例2
三(五氟乙基)三氟磷酸1,2-二甲基-3-丙基咪唑鎓
三(五氟乙基)三氟磷酸锂按照DE 196411 38的方法合成。产物在乙腈中按照下面反应式进行反应:
反应混合物在冷却下用玻璃漏斗真空过滤,以除去所形成的LiCl副产物。在减压下蒸馏除去溶剂,得到的三(五氟乙基)三氟磷酸1,2-二甲基-3-丙基咪唑鎓在减压下干燥。
实施例3
三(九氟丁基)三氟磷酸1-乙基-3-甲基咪唑鎓的合成
三(九氟丁基)三氟磷酸锂的合成类似于三(五氟乙基)三氟磷酸锂合成。产物在乙腈中按照下面反应式进行反应:
反应混合物在冷却下用玻璃漏斗真空过滤,以除去所形成的LiCl副产物。在减压下蒸馏除去溶剂,得到的三(九氟丁基)三氟磷酸1-乙基-3-甲基咪唑鎓在减压下干燥。
Claims (9)
2. 权利要求1的离子型液体,其中阴离子A-是三(五氟乙基)三氟磷酸根或三(九氟丁基)三氟磷酸根。
4. 如权要求1所定义的离子型液体在对质子惰性的溶制的混合物中的用途。
5. 如权利要求1所定义的离子型液体在与选自LiPF6、LiBF4、LiClO4、LiAsF6、LiCF3SO3、LiN(CF3SO2)2、LiC(CF3SO2)3和其混合物的导电性盐的混合物中的用途。
6. 如权利要求1所定义的离子型液体在电化学电池中的用途。
7. 如权利要求1所定义的离子型液体在超级电容器中的用途。
8. 如权利要求1所定义的离子型液体作为溶剂及在催化化学反应中的用途。
9. 如权利要求1所定义的离子型液体作为液压液的用途。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10027995A DE10027995A1 (de) | 2000-06-09 | 2000-06-09 | Ionische Flüssigkeiten II |
DE10027995.3 | 2000-06-09 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1327986A CN1327986A (zh) | 2001-12-26 |
CN100413873C true CN100413873C (zh) | 2008-08-27 |
Family
ID=7644877
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB011228059A Expired - Fee Related CN100413873C (zh) | 2000-06-09 | 2001-06-08 | 离子型液体ⅱ |
Country Status (10)
Country | Link |
---|---|
US (1) | US7153974B2 (zh) |
EP (1) | EP1162204B1 (zh) |
JP (1) | JP5236135B2 (zh) |
KR (1) | KR100781473B1 (zh) |
CN (1) | CN100413873C (zh) |
BR (1) | BR0102318A (zh) |
CA (1) | CA2349903C (zh) |
DE (2) | DE10027995A1 (zh) |
RU (1) | RU2272043C2 (zh) |
TW (1) | TWI300780B (zh) |
Families Citing this family (36)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10027995A1 (de) * | 2000-06-09 | 2001-12-13 | Merck Patent Gmbh | Ionische Flüssigkeiten II |
KR100473433B1 (ko) * | 2000-07-17 | 2005-03-08 | 마쯔시다덴기산교 가부시키가이샤 | 비수전해액 및 그것을 포함하는 비수전해액전지 및 전해콘덴서 |
DE10038858A1 (de) * | 2000-08-04 | 2002-02-14 | Merck Patent Gmbh | Fluoralkylphosphate zur Anwendung in elektrochemischen Zellen |
EP1205998A2 (de) | 2000-11-10 | 2002-05-15 | MERCK PATENT GmbH | Elektrolyte |
DE10055811A1 (de) | 2000-11-10 | 2002-05-29 | Merck Patent Gmbh | Tetrakisfluoroalkylborat-Salze und deren Verwendung als Leitsalze |
DE10109032A1 (de) * | 2001-02-24 | 2002-09-05 | Merck Patent Gmbh | Fluoralkylphosphat-Salze und Verfahren zur Herstellung dieser Substanzen |
DE10130940A1 (de) | 2001-06-27 | 2003-01-16 | Merck Patent Gmbh | Supersäuren, Herstellverfahren und Verwendungen |
JP2003313171A (ja) * | 2002-04-23 | 2003-11-06 | Kuraray Co Ltd | N−アルキル−n’−アルキルイミダゾリウム塩の製造方法 |
FR2840916B1 (fr) * | 2002-06-17 | 2004-08-20 | Inst Francais Du Petrole | Procede d'elimination des composes soufres et azotes de coupes hydrocarbonees |
US7750166B2 (en) * | 2002-08-16 | 2010-07-06 | University Of South Alabama | Ionic liquids containing a sulfonate anion |
AU2003263890A1 (en) | 2002-08-16 | 2004-03-03 | Sachem, Inc. | Lewis acid ionic liquids |
JP4085986B2 (ja) | 2003-04-01 | 2008-05-14 | ソニー株式会社 | 電池 |
DE10325051A1 (de) * | 2003-06-02 | 2004-12-23 | Merck Patent Gmbh | Ionische Flüssigkeiten mit Guanidinium-Kationen |
DE112004001729T5 (de) * | 2003-09-18 | 2006-10-19 | Sumitomo Chemical Co., Ltd. | Ionische Flüssigkeit und Reaktionsverfahren, das dieselbe einsetzt |
JP4982083B2 (ja) * | 2003-10-10 | 2012-07-25 | 出光興産株式会社 | 潤滑油 |
JP2005147394A (ja) * | 2003-10-23 | 2005-06-09 | Sankyo Seiki Mfg Co Ltd | 動圧軸受装置、及び、ディスク駆動装置 |
JP5376746B2 (ja) * | 2003-11-05 | 2013-12-25 | 協同油脂株式会社 | 半固体状潤滑剤組成物 |
US7423164B2 (en) * | 2003-12-31 | 2008-09-09 | Ut-Battelle, Llc | Synthesis of ionic liquids |
US8715521B2 (en) * | 2005-02-04 | 2014-05-06 | E I Du Pont De Nemours And Company | Absorption cycle utilizing ionic liquid as working fluid |
DE102005007100A1 (de) * | 2005-02-16 | 2006-08-17 | Solvent Innovation Gmbh | Prozess- bzw. Arbeitsmaschine mit ionischer Flüssigkeit als Betriebsflüssigkeit |
JP4926411B2 (ja) * | 2005-04-08 | 2012-05-09 | 出光興産株式会社 | グリース組成物 |
JP5074687B2 (ja) * | 2005-07-15 | 2012-11-14 | 出光興産株式会社 | 含油軸受用潤滑剤 |
WO2007055324A1 (ja) * | 2005-11-14 | 2007-05-18 | The Nippon Synthetic Chemical Industry Co., Ltd. | 合成潤滑油 |
US7737106B2 (en) * | 2005-11-29 | 2010-06-15 | The Procter & Gamble Company | Process for making an ionic liquid comprising ion actives |
US20070129568A1 (en) * | 2005-12-06 | 2007-06-07 | Ngimat, Co. | Ionic liquids |
DE102006005103A1 (de) * | 2006-02-04 | 2007-08-09 | Merck Patent Gmbh | Oxonium- und Sulfoniumsalze |
CN101454420B (zh) * | 2006-05-31 | 2012-07-11 | 纳幕尔杜邦公司 | 利用离子液体作为压缩机润滑剂的蒸汽压缩 |
US20080153697A1 (en) * | 2006-12-22 | 2008-06-26 | E. I. Dupont De Nemours And Company | Mixtures of ammonia and ionic liquids |
DE102007004698A1 (de) | 2007-01-31 | 2008-08-07 | Merck Patent Gmbh | Verbindungen enthaltend Organofluorochlorophosphatanionen |
DE102008032825B3 (de) * | 2008-07-11 | 2010-01-14 | Siemens Aktiengesellschaft | Strahlpumpe sowie Verfahren zu deren Betrieb |
JP2010287431A (ja) * | 2009-06-11 | 2010-12-24 | Sony Corp | 電池 |
CN102473527B (zh) | 2009-08-03 | 2014-07-30 | 默克专利有限公司 | 电解液体系 |
DE102009058969A1 (de) | 2009-12-18 | 2011-06-22 | Merck Patent GmbH, 64293 | Verbindung mit (Perfluoralkyl)fluorohydrogenphosphat - Anionen |
KR20130118322A (ko) * | 2010-09-27 | 2013-10-29 | 메르크 파텐트 게엠베하 | 관능화 플루오로알킬 플루오로포스페이트 염 |
DE102012006896A1 (de) | 2012-04-05 | 2013-10-10 | Merck Patent Gmbh | Silikate mit organischen Kationen |
PL3772129T3 (pl) | 2019-07-31 | 2021-09-27 | Innolith Technology AG | Elektrolit na bazie so2 do ogniwa akumulatorowego umożliwiającego wielokrotne ładowanie i zawierające ten elektrolit ogniwo akumulatorowe umożliwiające wielokrotne ładowanie |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0513278A (ja) * | 1991-07-04 | 1993-01-22 | Matsushita Electric Ind Co Ltd | 電解コンデンサ駆動用溶融塩形電解質 |
US5827602A (en) * | 1995-06-30 | 1998-10-27 | Covalent Associates Incorporated | Hydrophobic ionic liquids |
CN1232465A (zh) * | 1996-10-05 | 1999-10-20 | 默克专利股份有限公司 | 氟磷酸锂和其作为导电盐的用途 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS612278A (ja) * | 1984-06-14 | 1986-01-08 | Mitsui Petrochem Ind Ltd | 電池 |
EP0839139B2 (en) * | 1995-06-30 | 2009-11-18 | Covalent Associates Incorporated | Hydrophobic ionic liquids |
JPH1021914A (ja) * | 1996-07-05 | 1998-01-23 | Mitsubishi Chem Corp | 非水電解液二次電池 |
GB9616264D0 (en) * | 1996-08-02 | 1996-09-11 | British Nuclear Fuels Plc | Reprocessing irradiated fuel |
JPH11273734A (ja) * | 1998-03-23 | 1999-10-08 | Sanyo Chem Ind Ltd | 難燃性非水電解液およびそれを用いた二次電池 |
DE19910968A1 (de) * | 1999-03-12 | 2000-11-09 | Merck Patent Gmbh | Anwendung von Additiven in Elektrolyten für elektrochemische Zellen |
DE10008955C2 (de) * | 2000-02-25 | 2002-04-25 | Merck Patent Gmbh | Lithiumfluoralkylphosphate, Verfahren zu ihrer Herstellung und deren Verwendung als Leitsalze |
DE10026565A1 (de) * | 2000-05-30 | 2001-12-06 | Merck Patent Gmbh | Ionische Flüssigkeiten |
DE10027995A1 (de) * | 2000-06-09 | 2001-12-13 | Merck Patent Gmbh | Ionische Flüssigkeiten II |
-
2000
- 2000-06-09 DE DE10027995A patent/DE10027995A1/de not_active Withdrawn
-
2001
- 2001-05-21 DE DE50106762T patent/DE50106762D1/de not_active Expired - Lifetime
- 2001-05-21 EP EP01111953A patent/EP1162204B1/de not_active Expired - Lifetime
- 2001-06-07 CA CA002349903A patent/CA2349903C/en not_active Expired - Fee Related
- 2001-06-08 BR BR0102318-7A patent/BR0102318A/pt not_active Application Discontinuation
- 2001-06-08 JP JP2001173307A patent/JP5236135B2/ja not_active Expired - Fee Related
- 2001-06-08 CN CNB011228059A patent/CN100413873C/zh not_active Expired - Fee Related
- 2001-06-08 RU RU2001115605/04A patent/RU2272043C2/ru not_active IP Right Cessation
- 2001-06-08 KR KR1020010031905A patent/KR100781473B1/ko not_active IP Right Cessation
- 2001-06-11 TW TW090114064A patent/TWI300780B/zh not_active IP Right Cessation
- 2001-06-11 US US09/877,259 patent/US7153974B2/en not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0513278A (ja) * | 1991-07-04 | 1993-01-22 | Matsushita Electric Ind Co Ltd | 電解コンデンサ駆動用溶融塩形電解質 |
US5827602A (en) * | 1995-06-30 | 1998-10-27 | Covalent Associates Incorporated | Hydrophobic ionic liquids |
CN1232465A (zh) * | 1996-10-05 | 1999-10-20 | 默克专利股份有限公司 | 氟磷酸锂和其作为导电盐的用途 |
Also Published As
Publication number | Publication date |
---|---|
KR100781473B1 (ko) | 2007-12-03 |
US7153974B2 (en) | 2006-12-26 |
EP1162204B1 (de) | 2005-07-20 |
DE50106762D1 (de) | 2005-08-25 |
US20020015884A1 (en) | 2002-02-07 |
JP2002025610A (ja) | 2002-01-25 |
CA2349903C (en) | 2010-02-02 |
DE10027995A1 (de) | 2001-12-13 |
BR0102318A (pt) | 2002-02-13 |
CN1327986A (zh) | 2001-12-26 |
RU2272043C2 (ru) | 2006-03-20 |
JP5236135B2 (ja) | 2013-07-17 |
CA2349903A1 (en) | 2001-12-09 |
EP1162204A1 (de) | 2001-12-12 |
TWI300780B (en) | 2008-09-11 |
KR20020017934A (ko) | 2002-03-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN100413873C (zh) | 离子型液体ⅱ | |
JP4611567B2 (ja) | イオン性液体 | |
KR100801811B1 (ko) | 전기화학 전지용 플루오로알킬 포스페이트 | |
KR20010110330A (ko) | 화학 전지용 전해질중의 첨가제인 실란 화합물 | |
JP3728236B2 (ja) | テトラキスフルオロアルキルホウ酸塩およびそれらの導電性塩としての使用 | |
US20010033964A1 (en) | Alkylspiroborate salts for use in electrochemical cells | |
US6423454B1 (en) | Lithium fluoroalkylphosphates and their use as electrolyte salts | |
KR20010062269A (ko) | 전기화학 전지에 사용하기 위한 알킬스피로보레이트 염 | |
US6893774B2 (en) | Fluoroalkylphosphate salts, and process for the preparation of these substances | |
US20020001755A1 (en) | Lithium salt and a process of preparing thereof | |
JP2002249670A (ja) | 電解質 | |
RU2246499C2 (ru) | Способ получения литиевых комплексных солей для использования в химических источниках тока | |
JP2002356491A (ja) | フルオロアルキルホスフェートの調製方法 | |
KR20010040169A (ko) | 전기화학 전지에 사용하기 위한 착체 염 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20080827 Termination date: 20170608 |
|
CF01 | Termination of patent right due to non-payment of annual fee |