WO1999007676A1 - Procedes de preparation de methanides, d'imides et de sulfonates contenant du perfluoroalcane-1-sulfonyl (perfluoroalkylesulfonyl) imide-n-sulfonyle, et perfluoroalcane-1-n- sulfonylbis(perfluoralkylsulfonyl) methanides - Google Patents
Procedes de preparation de methanides, d'imides et de sulfonates contenant du perfluoroalcane-1-sulfonyl (perfluoroalkylesulfonyl) imide-n-sulfonyle, et perfluoroalcane-1-n- sulfonylbis(perfluoralkylsulfonyl) methanides Download PDFInfo
- Publication number
- WO1999007676A1 WO1999007676A1 PCT/EP1998/004648 EP9804648W WO9907676A1 WO 1999007676 A1 WO1999007676 A1 WO 1999007676A1 EP 9804648 W EP9804648 W EP 9804648W WO 9907676 A1 WO9907676 A1 WO 9907676A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- lithium
- compounds
- perfluoroalkane
- perfluoroalkylsulfonyl
- Prior art date
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- 150000003949 imides Chemical class 0.000 title description 5
- 150000003871 sulfonates Chemical class 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 65
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 21
- 239000003792 electrolyte Substances 0.000 claims abstract description 19
- 229910052792 caesium Inorganic materials 0.000 claims abstract description 8
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 8
- 229910052701 rubidium Inorganic materials 0.000 claims abstract description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 60
- 239000011734 sodium Substances 0.000 claims description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 23
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- -1 lithium halide Chemical class 0.000 claims description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000000010 aprotic solvent Substances 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 229910003002 lithium salt Inorganic materials 0.000 claims description 12
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 159000000002 lithium salts Chemical class 0.000 claims description 11
- 238000009938 salting Methods 0.000 claims description 11
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 9
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 claims description 9
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 8
- 239000011707 mineral Substances 0.000 claims description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 8
- 238000000746 purification Methods 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 150000002642 lithium compounds Chemical class 0.000 claims description 5
- 159000000000 sodium salts Chemical class 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 150000004292 cyclic ethers Chemical class 0.000 claims description 4
- TXLQIRALKZAWHN-UHFFFAOYSA-N dilithium carbanide Chemical compound [Li+].[Li+].[CH3-].[CH3-] TXLQIRALKZAWHN-UHFFFAOYSA-N 0.000 claims description 4
- 239000000543 intermediate Substances 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 238000010626 work up procedure Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 35
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 9
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 238000007127 saponification reaction Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 235000010755 mineral Nutrition 0.000 description 6
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000003513 alkali Substances 0.000 description 4
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000002484 cyclic voltammetry Methods 0.000 description 3
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 3
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 description 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 2
- 241000321453 Paranthias colonus Species 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 229910001416 lithium ion Inorganic materials 0.000 description 2
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- GYJCQBSYXHMHED-UHFFFAOYSA-N sodium;trifluoromethylsulfonyl(trimethylsilyl)azanide Chemical compound [Na+].C[Si](C)(C)[N-]S(=O)(=O)C(F)(F)F GYJCQBSYXHMHED-UHFFFAOYSA-N 0.000 description 2
- KDKCKVFVXANWQZ-UHFFFAOYSA-N sodium;trifluoromethylsulfonylazanide Chemical compound [Na+].[NH-]S(=O)(=O)C(F)(F)F KDKCKVFVXANWQZ-UHFFFAOYSA-N 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- QBOFWVRRMVGXIG-UHFFFAOYSA-N trifluoro(trifluoromethylsulfonylmethylsulfonyl)methane Chemical compound FC(F)(F)S(=O)(=O)CS(=O)(=O)C(F)(F)F QBOFWVRRMVGXIG-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- VPSOPXOTOKNDHQ-UHFFFAOYSA-N 1,2,2,3,3,4,5,5,6,6-decafluoropiperazine Chemical class FN1C(F)(F)C(F)(F)N(F)C(F)(F)C1(F)F VPSOPXOTOKNDHQ-UHFFFAOYSA-N 0.000 description 1
- BJBXQQZMELYVMD-UHFFFAOYSA-N 2,2,3,3,4,5,5,6,6-nonafluoromorpholine Chemical compound FN1C(F)(F)C(F)(F)OC(F)(F)C1(F)F BJBXQQZMELYVMD-UHFFFAOYSA-N 0.000 description 1
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 1
- UJQZTMFRMLEYQN-UHFFFAOYSA-N 3-methyloxane Chemical compound CC1CCCOC1 UJQZTMFRMLEYQN-UHFFFAOYSA-N 0.000 description 1
- LJPCNSSTRWGCMZ-UHFFFAOYSA-N 3-methyloxolane Chemical compound CC1CCOC1 LJPCNSSTRWGCMZ-UHFFFAOYSA-N 0.000 description 1
- DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 159000000006 cesium salts Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000006138 lithiation reaction Methods 0.000 description 1
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 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 description 1
- QVXQYMZVJNYDNG-UHFFFAOYSA-N lithium;bis(trifluoromethylsulfonyl)methylsulfonyl-trifluoromethane Chemical compound [Li+].FC(F)(F)S(=O)(=O)[C-](S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F QVXQYMZVJNYDNG-UHFFFAOYSA-N 0.000 description 1
- MCVFFRWZNYZUIJ-UHFFFAOYSA-M lithium;trifluoromethanesulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)F MCVFFRWZNYZUIJ-UHFFFAOYSA-M 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011356 non-aqueous organic solvent Substances 0.000 description 1
- 239000011255 nonaqueous electrolyte Substances 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000005463 sulfonylimide group Chemical group 0.000 description 1
- ZUEAAEQNFKVONV-UHFFFAOYSA-N sulfonylmethane Chemical class [CH-]=S(=O)=O ZUEAAEQNFKVONV-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- MKOBNHWWZPEDQJ-UHFFFAOYSA-N trifluoro(methanidylsulfonyl)methane Chemical compound [CH2-]S(=O)(=O)C(F)(F)F MKOBNHWWZPEDQJ-UHFFFAOYSA-N 0.000 description 1
- SLVAEVYIJHDKRO-UHFFFAOYSA-N trifluoromethanesulfonyl fluoride Chemical compound FC(F)(F)S(F)(=O)=O SLVAEVYIJHDKRO-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000001075 voltammogram Methods 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0566—Liquid materials
- H01M10/0568—Liquid materials characterised by the solutes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/48—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/02—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms
- C07C317/04—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
-
- 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
Definitions
- PERFLU0RALKAN-1-SULF0NYL (PERFLUORALKYLSULFONYL) IMID-N-SULFONYL CONTAINING METHANIDES, IMIDES AND SULFONATES, AND THEIR USE IN ELECTROLYTE SYSTEMS
- the invention relates to compounds of the formula I.
- R and Ri independently of one another RC (S0 2 R F ) 2, N (S0 2 RF), O, mean with a counter ion from the group Li, Na, K, Cs, Rb, B ⁇ / 2 , and n is 1, 2 or 3 and x is 1, 2, 3 or 4, processes for their preparation, their use in electrolyte systems as conductive salts in lithium batteries, and electrolytes for lithium batteries containing compounds of the general formula (I), but also secondary lithium batteries which corresponding electrolytes contain.
- Lithium compounds such as e.g. B. Li [F 3 CS03] (lithium triflate) are known, which are easy to display and are therefore also commercially available. Corresponding compounds are unsuitable for use in secondary batteries, however, since they have insufficient conductivity in the typical aprotic solvents used therein (Volkov, OV; Skudin, AM; Ignat'ev, NV; Soviet Electrochemistry, 1992, 28, 1527).
- lithium tris (trifluoromethylsulfonyl) methanide Li [C (S0 2 CF 3 ) 3]
- lithium bis (trifluoromethylsulfonyl) imide Li [N (S0 2 CF 3 ) 2 j
- Electrochemical. Sci. Case Western Reserve Univ., Cleveland, OH, USA Report (1989), GRI-89/0025; Order No. PB89-178768, 214 pp. Avail .: from Geov. Rep. Announce. Index (U.S.) 1989, 89 (12), Abstr. No. 932, 621; A. J. Appleby et al. Cent. Electrochemical. Syyt. Hydrogen Res., Texas A and M Univ. System, College Station, TX, 77843-3402, USA, Morgantown Energy Technol. Cent., [Rep.] DOE / METC (U.S. Dep. Energy), 1991 DOE / METC-91/6120, Proc. Annu. Fuel Cells Contract. Rev. Meet.
- the object of the invention is therefore to provide suitable lithium salts with a sufficient lithium content, which are corrosion-stable, have an improved cation conductivity compared to known comparable lithium salts and at the same time do not lead to any disadvantageous countervoltage due to opposite anion charges.
- M is a counter ion from the group Li, Na, K, Cs, Rb, B 1 2 , and
- Alkane bis (sulfonyl fluoride) a sodium perfluoroalkane-1-sulfonyl fluoride-N-trifluoromethylsulfonylimide of the formula (IV)
- R F has the meaning given above, produces it and either e) it can react with sodium perfluoalkylsulfonyltrimethylsilylamide of the formula (
- R F has the meaning given above, or f) converts an equivalent with a dilithiated bis (perfluoroalkylsulfonyl) methane and by suitable ones
- RF has the meaning given above, produces or g) is reacted with an alkaline lithium salt and by salting with a lithium halide perfluoroalkane-1-sulfonyl (perfluoroalkylsulfonyl) imide-N-sulfonate of the formula (VII)
- the invention also relates to a process for the preparation of compounds of the formula (I) in which R 1 and R are the same and have the meaning (C (S0 2 RF) 2 , characterized in that a) bis (perfluoroalkylsulfonyl) methane in lithiated an aprotic, organic solvent from the group tetrahydrofuran, 2-methyl tetrahydrofuran and diethyl ether at a temperature of -10 - +50 ° C, preferably at 10 to 25 ° C and with an ⁇ , ⁇ -perfluoroalkane bis (sulfonyl fluoride) of the formula ( VIII) F0 2 S- (CF 2 ) n -S0 2 F (VIII) in a molar ratio of 1: 0.3 to 1: 0.5 at
- Li 2 [(R F S0 2 ) 2 C-S0 2 - (CF 2 ) n-S0 2 -C (S0 2 R F ) 2] (Xb) are particularly the subject of this invention.
- di-lithium imide sulfonates of the formula (VII) are also di-lithium imide sulfonates of the formula (VII).
- Alkaline lithium salts from the group Li 2 C0 3 and LiOH * H 2 O or others are suitable for saponification.
- the di-lithium imide sulfonates can be obtained by salting with a lithium halide, preferably lithium chloride.
- the invention thus relates to a process which can be represented by the following scheme using the example of the lithium compounds according to the invention:
- Process scheme 1 As can be seen from the process scheme given above, the compounds of the formula (III) are prepared in three stages. It has now been found that the first reaction step advantageously does not have to be carried out in liquid ammonia, as described by DesMarteau (DD DesMarteau, M. Witz,
- Formula (IV) produce new lithium compounds of formula (V). It has been found that with increasing chain length of the ⁇ , ⁇ -perfluoroalkane bis (sulfonyl fluoride) used, the yields of the reaction of compounds of the formula (IV) with compounds of the formula (III) which are carried out decrease. After purification and
- compounds of the formula (V) are prepared by compounds of the formula (IV) in an aprotic solvent from the group of the cyclic, preferably in pyran (corresponds to ( ⁇ ) - 3-methyltetrahydropyran), at temperatures from 100 to 110 ° C. with compounds of formula (III), which are used in a 10 to 20% excess, are reacted.
- compounds of formula (IX) are obtained:
- n 1, 2 or 3.
- di-potassium salts are prepared therefrom with the aid of alkaline-reacting aqueous potassium ion-containing solutions, preferably a potassium hydroxide solution, and subsequent salting with a lithium halide from the group consisting of LiCl, LiJ and LiBr, preferably lithium chloride , in aprotic organic solvents, such as tetrahydrofuran or 1,3-dioxolane ... di-lithium bisimides of the formula (V).
- aqueous potassium ion-containing solutions preferably a potassium hydroxide solution
- a lithium halide from the group consisting of LiCl, LiJ and LiBr, preferably lithium chloride
- aprotic organic solvents such as tetrahydrofuran or 1,3-dioxolane ... di-lithium bisimides of the formula (V).
- the process according to the invention also relates, as can be seen from the scheme given above, to the preparation of the new perfluoraikan-1-sulfonyl (perfluoroalkylsulfonyl) imide-n-sulfonylbis (perfluoroalkylsulfonyl) methanides or mixed di-lithium imide Methanides of the general formula (VI).
- bis (perfluoroalkylsulfonyl) methane is used in a nonpolar, aprotic solvent from the group consisting of tetrahydrofuran and 2-methyltetrahydrofuran with the aid of butyl lithium or methyl lithium in a solvent such as cyclohexane, n-hexane or other cyclic or acyclic hydrocarbons at temperatures of - 10 to 30 ° C, preferably at 10 - 20 ° C, dilithiated.
- the mixed di-lithium imide methanides of the formula (VI) according to the invention can be prepared. After purification, the desired product is obtained in a yield of about 25 to 35%.
- the present invention also relates to a process for the preparation of di-alkali imide sulfonates, in particular di-lithium imide sulfonates of the formula (VII). Experiments have shown that these compounds can be prepared by saponification of the corresponding monoanion of the formula (IV). For this purpose, an aqueous solution of an alkaline lithium salt from the group LiOH * H 2 0 and Li 2 C0 3 can be used.
- This reaction is preferably carried out with a lithium hydroxide solution; namely the monoanion is placed in aqueous solution and the alkaline lithium salt is added in an equimolar to 1.5 times the amount.
- the saponification takes place at elevated temperature, especially at boiling temperature.
- activated carbon can be added to the reaction solution to remove impurities.
- the reaction product can be obtained in a simple manner by removing the water and the di-lithium salt can be obtained therefrom by salting.
- the reaction product of the saponification is obtained in an aprotic solvent from the group consisting of the ethers tetrahydrofuran and 1,3-dioxolane, preferably tetrahydrofuran added and mixed with an equimolar to 1.5 times the amount of a lithium halide, also dissolved in an aprotic organic solvent, preferably the same one that was used to dissolve the saponification product, and at about 20 to 40 ° C., preferably at room temperature for stirred for some time.
- the sodium halide that forms precipitates and can be used in a simple manner, e.g. B. by filtration or alternative methods known to those skilled in the art. After removal of the solvent, preferably by vacuum distillation, the desired di-alkali imide sulfonate is obtained as a solid in a yield of at least 98%.
- M 2 [(F 3 CSO 2 ) 2C-S0 2 - (CF 2 ) n -S0 2 -C (SO 2 CF 3 ) 2 ], (X) wherein M, n and R have the meanings given above, the subject of the invention, and a process for their preparation.
- Bis (perfluoroalkylsulfonyl) methane is in an aprotic solvent from the group of cyclic ethers, preferably in Tetrahydrofuran added and lithiated with the aid of alkyl lithium, such as butyllithium or methyl lithium, which is prepared in a known manner and is dissolved in hydrocarbon, such as cyclohexane. However, it can also be reacted in a corresponding manner with an alkyl-Mg compound. This lithiation reaction can occur in a
- the starting materials are used in this reaction in a molar ratio of 1: 0.3 to 1: 0.5.
- the reaction takes place in a cyclic or acyclic ether, preferably in tetrahydrofuran, at temperatures between 10-50 ° C. Particularly good yields are obtained when working in a temperature range of 25-30 ° C.
- the product obtained is converted to the corresponding dianion with a cesium salt from the group Cs 2 C03, which is alkaline in solution, and CsOH in aqueous solution and by successive treatment , if necessary after prior purification, such as. B. by recrystallization or by other methods known to those skilled in the art, in an organic solvent from the group of diethyl ether and dibutyl ether, with a mineral acid, preferably hydrochloric acid, and by treatment with an aqueous lithium hydroxide solution in the desired salt, such as. B. in the di-lithium bismethanide of the formula (Xa)
- the di-lithium bismethanide is released in particular by using equimolar amounts of lithium hydroxide or of his hydrate.
- the lithium hydroxide can also be used in excess to shift the reaction equilibrium.
- R F in the compounds according to the invention can represent the fluorine-saturated radicals trifluoromethyl, pentafluoroethyl, i- and n-heptafluoropropyl, i-, n-, t-nonafluorobutyl.
- lithium salts of the compounds of the general formula (I) a) Li 2 [(F 3 CS0 2 ) 2 C-S0 2 -CF 2 -SOrC (S0 2 CF 3 ) 2 ] b) Li 2 [(F 3 CS ⁇ 2 ) 2 C-S0 2 - (CF 2 ) 2 -S0 2 -C (S0 2 CF 3 ) 2 ] c) Li 2 [(F 3 CS0 2 ) 2 C-S0 2 - (CF 2 ) 3-S0 2 -C (S0 2 CF 3 ) 2] d) Li 2 [F 3 CSO 2 N-S0 2 -CF 2 -C (S0 2 CF 3 ) 2 ] e) Li 2 [F 3 CS0 2 N-S0 2 - (CF 2 ) 2 -C (S0 2 CF 3 ) 2 ] f) Li 2 [F 3 CS0 2 N-S0 2 - (CF 2 ) 3 ] f
- the compounds according to the invention are extremely stable. In dry storage at a temperature of around 100 ° C, no decomposition occurs. Only at significantly higher temperatures above 200 ° C does decomposition appear on the basis of discoloration. But also when stored in solution, such as. B. in organic solvents such as tetrahydrofuran or acetonitrile, no color changes or decomposition products can be detected even after several weeks of storage, for this reason the new compounds according to the invention are particularly suitable as a conductive salt in non-aqueous electrolytes for lithium secondary batteries. Such electrolytes contain, in addition to lithium-organic salts, as are the compounds according to the invention, one or more non-aqueous organic solvents and, if appropriate, further additives.
- lithium secondary batteries Further details on such electrolytes, their structure and the mode of operation of lithium secondary batteries are known to the person skilled in the relevant art.
- the compounds according to the invention can be used in complete analogy to lithium compounds known for this application.
- the compounds of the invention also show an extraordinarily high stability.
- the corresponding battery cells show excellent properties in terms of capacity and
- Lithium bismethanides have very good conductivities in aprotic solvents. Furthermore, they contribute to a decrease in the tendency to corrode aluminum current arresters and are themselves stable to decomposition reactions. In detail, these salts have a passivating or protective effect on the aluminum.
- Compounds of the general formula (I) according to the invention which can be used as conductive salts in both primary and secondary cells can therefore act as surface-active salts in electrolytes.
- the lithium salts described are particularly well suited for use as conductive salts in electrolytes.
- the advantageous properties of these salts in this connection depend on the content of lithium in the salts produced.
- the di-lithium imide sulfonate of formula (VII) has the highest lithium content with 3.91%.
- this salt can be prepared in very good yields by the process described here. So the saponification and the subsequent salting run almost quantitatively.
- the compound of the formula (IV) used for its preparation is already obtained in a yield of 90% and more, so that the preparation of these conductive salts per se is associated with very low losses of starting material.
- HMDS hexamethyldisilazane
- IR (KBr pellet): v 2960 (m), 2903 (w), 1277 (s), 1251 (vs), 1231 (vs), 1205 (vs), 1171 (s), 1145 (s), 1059 (vs), 989 (m), 840 (vs), 762 (m), 730 (w), 712 (m), 692 (w), 620 (s), 579 (m), 548 (w), 523 (w), 489 (w), 483 (w), 476 (w), 471 (w), 462 (w), 427 (w).
- the sublimation sump is taken up in 100-150 ml of water, filtered through granular activated carbon and neutralized with potassium hydroxide. After boiling with activated carbon and subsequent filtration, the water is removed in vacuo. The colorless solid is recrystallized from approx. 300 - 400 ml isopropanol. After filtering, the crystals are dried in a high vacuum at 70 ° C.
- a solution of 15.40 is added to a solution of 100.00 g (182 mmol) of K 2 [F 3 CS0 2 -N-S0 2 -CF 2 - S0 2 -N-S0 2 CF 3 ] in 100 ml of tetrahydrofuran g (364 mmol) lithium chloride in 650 ml tetrahydrofuran. After stirring for 30 minutes, the precipitated potassium chloride is filtered off and the THF is removed in vacuo. The resulting colorless solid is dried under high vacuum ( ⁇ 0.1 Torr) at about 80 ° C.
- the reaction solution is heated to 60 ° C for two hours.
- the solvent mixture is then removed.
- the resulting solid is taken up in 500 ml of 3 molar hydrochloric acid and stirred for about four hours.
- the solution is then extracted four times with 150 ml of diethyl ether each time. After combining the ether phases and removing the solvent, the unreacted starting materials are distilled off.
- the remaining sump is dissolved in 500 ml of water and neutralized with approx. 33 g of cesium carbonate.
- the cesium salt that precipitates is brought into solution by boiling.
- the solution is then mixed with activated carbon and, after heating for 30 minutes, filtered, the cesium salt which has crystallized out is optionally recrystallized again with water.
- the salt Li 2 [(F 3 CS0 2 ) 2 C-S0 2 - (CF 2 ) 3 -S0 2 -C (S0 2 CF 3 ) 2 ] has EC / DMC (1: 1; water content of about 10 - 20 ppm) and EC / DEC (1: 1; water content of about 10 - 20 ppm) good stability towards lithium, in the base current
- Cyclic voltammograms show no signals that could indicate cathodic decomposition.
- Oxidation stability a) Oxidation on inert platinum electrodes The decomposition potential of the divalent methanide was determined to be 5.3 V versus Li / Li + , regardless of the solvent mixture. This indicates that the solvent is probably already decomposing.
- Fig. 2. shows a voltammogram measured with an EC / DMC mixture as a solvent.
- cyclic properties were determined potentiodynamically using cyclic voltammetry (Fig. 3, Tab. 4) and galvanostatically (Tab. 5 and 6). The results are in the range of the salts already examined.
- Fig. 1 are basic current cyclic voltammetric measurements which are performed using Li 2 [(F 3 CS0 2 ) 2 C-S0 2 - (CF 2 ) 3 -S0 2 -C (S0 2 CF 3 )] (0.58 molal) in DMC / EC (mdcv 279) were carried out, graphically evaluated.
- the implementation was carried out under the following conditions:
- Electrode area 0.503 cm 2
- Measuring arrangement 3 electrode arrangement working electrode V2A stainless steel
- Electrode area 0.503 cm 2
- FIG. 3 shows a graphical representation of the lithium deposition by means of cyclovoltaic experiments, using the example of Li 2 [(F 3 CS0 2 ) 2 C-S0 2 - (CF 2 ) 3 -S0 2 -C (S0 2 CF 3 ) 2 ] (0.58 molal) in DMC / EC (mdcv 280).
- the implementation was carried out under the following conditions:
- Measuring arrangement 3 electrode arrangement working electrode V2A stainless steel
- Electrode area 0.503 cm 2
- Fig. 4 shows the anodic stability of Li 2 [(F 3 CS0 2 ) 2 C-SO 2 - (CF 2 ) 3 -S0 2 -C (S0 2 CF 3 ) 2 ] (0.58 molal) in DMC / EC (mdcv 284) on aluminum (electrode area o, 583 cm 2 )
- Strip current density istrip 1 mA cm 2
- Strip current density istrip 1 mA / cm 2
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Abstract
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2000506180A JP2001512714A (ja) | 1997-08-06 | 1998-07-24 | ペルフルオロアルカン−1−スルホニル(ペルフルオロアルキルスルホニル)イミド−n−スルホニル−含有メタニド、イミドおよびスルホネート化合物の製造方法およびペルフルオロアルカン−1−n−スルホニルビス(ペルフルオロアルキルスルホニル)メタニド化合物 |
EP98943778A EP1001931A1 (fr) | 1997-08-06 | 1998-07-24 | Procedes de preparation de methanides, d'imides et de sulfonates contenant du perfluoroalcane-1-sulfonyl (perfluoroalkylesulfonyl) imide-n-sulfonyle, et perfluoroalcane-1-n- sulfonylbis(perfluoralkylsulfonyl) methanides |
KR1020007001199A KR20010022605A (ko) | 1997-08-06 | 1998-07-24 | 퍼플루오로알칸-1-설포닐(퍼플루오로알킬설포닐)이미드-엔-설포닐을 포함하는 메타나이드, 이미드 및 설포네이트, 및퍼플루오로알칸-1-엔-설포닐비스(퍼플루오로알킬설포닐)메타나이드의 제조방법 |
Applications Claiming Priority (2)
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DE19733948A DE19733948A1 (de) | 1997-08-06 | 1997-08-06 | Verfahren zur Herstellung von Perfluoralkan-1-sulfonyl(perfluoralkylsulfonyl) imid-N-sulfonyl enthaltende Methanide, Imide und Sulfonate, und Perfluoralkan-1-N-(sulfonylbis(perfluoralkylsulfonyl)methaniden) |
DE19733948.4 | 1997-08-06 |
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WO1999007676A1 true WO1999007676A1 (fr) | 1999-02-18 |
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PCT/EP1998/004648 WO1999007676A1 (fr) | 1997-08-06 | 1998-07-24 | Procedes de preparation de methanides, d'imides et de sulfonates contenant du perfluoroalcane-1-sulfonyl (perfluoroalkylesulfonyl) imide-n-sulfonyle, et perfluoroalcane-1-n- sulfonylbis(perfluoralkylsulfonyl) methanides |
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EP (1) | EP1001931A1 (fr) |
JP (1) | JP2001512714A (fr) |
KR (1) | KR20010022605A (fr) |
DE (1) | DE19733948A1 (fr) |
TW (1) | TW438803B (fr) |
WO (1) | WO1999007676A1 (fr) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2003017409A3 (fr) * | 2001-08-17 | 2004-01-22 | Merck Patent Gmbh | Electrolytes polymeres et leur utilisation dans des cellules galvaniques |
WO2004072021A1 (fr) * | 2003-02-14 | 2004-08-26 | Daikin Industries, Ltd. | Compose d'acide fluorosulfonique, procede de production de celui-ci et utilisation de celui-ci |
US20140093783A1 (en) * | 2011-06-07 | 2014-04-03 | 3M Innovative Properties Company | Lithium-ion electrochemical cells including fluorocarbon electrolyte additives |
CN111883835A (zh) * | 2020-07-24 | 2020-11-03 | 香河昆仑化学制品有限公司 | 一种锂离子电池非水电解液和锂离子电池 |
US20220131186A1 (en) * | 2020-10-27 | 2022-04-28 | Ford Global Technologies, Llc | Single-ion polymer electrolyte molecular design |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
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DE19919347A1 (de) * | 1999-04-28 | 2000-11-02 | Merck Patent Gmbh | Verfahren zur Aufreinigung von Methanid-Elektrolyten (II) |
US6727386B2 (en) * | 2001-10-25 | 2004-04-27 | 3M Innovative Properties Company | Aromatic imide and aromatic methylidynetrissulfonyl compounds and method of making |
JP4469692B2 (ja) * | 2004-09-14 | 2010-05-26 | 富士フイルム株式会社 | 感光性組成物、該感光性組成物に用いられる化合物及び該感光性組成物を用いたパターン形成方法 |
JP4819409B2 (ja) * | 2005-06-15 | 2011-11-24 | 日本電気株式会社 | 非水電解液二次電池の充放電方法 |
JP2010159256A (ja) * | 2010-01-18 | 2010-07-22 | Fujifilm Corp | 感光性組成物に有用な酸及びその塩 |
JP6582880B2 (ja) | 2014-12-01 | 2019-10-02 | セントラル硝子株式会社 | 2価のアニオンを有するイミド酸化合物及びその製造方法 |
JP6853636B2 (ja) * | 2016-09-08 | 2021-03-31 | 三菱マテリアル電子化成株式会社 | ペルフルオロアルキルスルホンアミドの製造方法 |
JPWO2023119946A1 (fr) * | 2021-12-24 | 2023-06-29 | ||
CN118451580A (zh) * | 2022-02-25 | 2024-08-06 | 株式会社村田制作所 | 二次电池 |
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- 1997-08-06 DE DE19733948A patent/DE19733948A1/de not_active Withdrawn
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- 1998-07-24 JP JP2000506180A patent/JP2001512714A/ja active Pending
- 1998-07-24 WO PCT/EP1998/004648 patent/WO1999007676A1/fr not_active Application Discontinuation
- 1998-07-24 EP EP98943778A patent/EP1001931A1/fr not_active Withdrawn
- 1998-07-24 KR KR1020007001199A patent/KR20010022605A/ko not_active Withdrawn
- 1998-08-03 TW TW087112762A patent/TW438803B/zh not_active IP Right Cessation
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WO1988003331A1 (fr) * | 1986-10-30 | 1988-05-05 | Centre National De La Recherche Scientifique (Cnrs | Nouveau materiau a conduction ionique constitue par un sel en solution dans un electrolyte liquide |
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Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003017409A3 (fr) * | 2001-08-17 | 2004-01-22 | Merck Patent Gmbh | Electrolytes polymeres et leur utilisation dans des cellules galvaniques |
WO2004072021A1 (fr) * | 2003-02-14 | 2004-08-26 | Daikin Industries, Ltd. | Compose d'acide fluorosulfonique, procede de production de celui-ci et utilisation de celui-ci |
US7482302B2 (en) | 2003-02-14 | 2009-01-27 | Daikin Industries, Ltd. | Fluorosulfonic acid compound, process for producing the same, and use thereof |
US20140093783A1 (en) * | 2011-06-07 | 2014-04-03 | 3M Innovative Properties Company | Lithium-ion electrochemical cells including fluorocarbon electrolyte additives |
US9455472B2 (en) * | 2011-06-07 | 2016-09-27 | 3M Innovative Properties Company | Lithium-ion electrochemical cells including fluorocarbon electrolyte additives |
CN111883835A (zh) * | 2020-07-24 | 2020-11-03 | 香河昆仑化学制品有限公司 | 一种锂离子电池非水电解液和锂离子电池 |
CN111883835B (zh) * | 2020-07-24 | 2023-05-23 | 香河昆仑新能源材料股份有限公司 | 一种锂离子电池非水电解液和锂离子电池 |
US20220131186A1 (en) * | 2020-10-27 | 2022-04-28 | Ford Global Technologies, Llc | Single-ion polymer electrolyte molecular design |
US11682793B2 (en) * | 2020-10-27 | 2023-06-20 | Ford Global Technologies. Llc | Single-ion polymer electrolyte molecular design |
Also Published As
Publication number | Publication date |
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DE19733948A1 (de) | 1999-02-11 |
EP1001931A1 (fr) | 2000-05-24 |
JP2001512714A (ja) | 2001-08-28 |
KR20010022605A (ko) | 2001-03-26 |
TW438803B (en) | 2001-06-07 |
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