JP2022507458A - リチウムイオン電池およびリチウム金属電池のアノードに対して安定である有機溶媒を使用して、リチウムビス(フルオロスルホニル)イミド(lifsi)から反応性溶媒を除去するためのプロセス - Google Patents
リチウムイオン電池およびリチウム金属電池のアノードに対して安定である有機溶媒を使用して、リチウムビス(フルオロスルホニル)イミド(lifsi)から反応性溶媒を除去するためのプロセス Download PDFInfo
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- JP2022507458A JP2022507458A JP2021526413A JP2021526413A JP2022507458A JP 2022507458 A JP2022507458 A JP 2022507458A JP 2021526413 A JP2021526413 A JP 2021526413A JP 2021526413 A JP2021526413 A JP 2021526413A JP 2022507458 A JP2022507458 A JP 2022507458A
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- lifsi
- ppm
- solvent
- reactive
- organic solvent
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- VDVLPSWVDYJFRW-UHFFFAOYSA-N lithium;bis(fluorosulfonyl)azanide Chemical compound [Li+].FS(=O)(=O)[N-]S(F)(=O)=O VDVLPSWVDYJFRW-UHFFFAOYSA-N 0.000 title claims abstract description 1129
- 239000002904 solvent Substances 0.000 title claims abstract description 663
- 238000000034 method Methods 0.000 title claims abstract description 493
- 239000003960 organic solvent Substances 0.000 title claims abstract description 261
- 230000008569 process Effects 0.000 title abstract description 114
- 229910052744 lithium Inorganic materials 0.000 title description 203
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 title description 19
- 229910001416 lithium ion Inorganic materials 0.000 title description 19
- 238000004519 manufacturing process Methods 0.000 claims abstract description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 393
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 177
- 238000001914 filtration Methods 0.000 claims description 107
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 104
- 239000007787 solid Substances 0.000 claims description 99
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical group COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 85
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 80
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 69
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 54
- -1 alkyl acetates Chemical class 0.000 claims description 54
- 229910052786 argon Inorganic materials 0.000 claims description 52
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 46
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 42
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 42
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 42
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 42
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 42
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 42
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 42
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 36
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 34
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 32
- 239000011261 inert gas Substances 0.000 claims description 24
- 239000012298 atmosphere Substances 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 23
- SBLRHMKNNHXPHG-UHFFFAOYSA-N 4-fluoro-1,3-dioxolan-2-one Chemical compound FC1COC(=O)O1 SBLRHMKNNHXPHG-UHFFFAOYSA-N 0.000 claims description 22
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 21
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 21
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims description 20
- 229940017219 methyl propionate Drugs 0.000 claims description 20
- 239000007789 gas Substances 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- 238000011010 flushing procedure Methods 0.000 claims description 17
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 16
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 12
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 10
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 10
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims description 10
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 10
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 10
- 229940090181 propyl acetate Drugs 0.000 claims description 10
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 10
- 229940043232 butyl acetate Drugs 0.000 claims description 8
- 229940093499 ethyl acetate Drugs 0.000 claims description 8
- 229910001873 dinitrogen Inorganic materials 0.000 claims description 7
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 claims description 6
- 150000002825 nitriles Chemical class 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 150000005677 organic carbonates Chemical class 0.000 claims description 4
- 239000000047 product Substances 0.000 abstract description 357
- 239000012535 impurity Substances 0.000 abstract description 356
- 238000000746 purification Methods 0.000 abstract description 138
- 238000006386 neutralization reaction Methods 0.000 abstract description 53
- 150000003839 salts Chemical class 0.000 abstract description 52
- 238000006467 substitution reaction Methods 0.000 abstract description 23
- 229910010941 LiFSI Inorganic materials 0.000 abstract 5
- 239000013067 intermediate product Substances 0.000 abstract 1
- 239000003792 electrolyte Substances 0.000 description 186
- 239000000243 solution Substances 0.000 description 92
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 80
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 66
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- 230000009467 reduction Effects 0.000 description 66
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 60
- 239000000203 mixture Substances 0.000 description 58
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 54
- 239000000706 filtrate Substances 0.000 description 50
- 238000006243 chemical reaction Methods 0.000 description 35
- 230000015572 biosynthetic process Effects 0.000 description 34
- 239000000460 chlorine Substances 0.000 description 34
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 28
- 239000012299 nitrogen atmosphere Substances 0.000 description 28
- 238000003756 stirring Methods 0.000 description 28
- 230000002194 synthesizing effect Effects 0.000 description 28
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 24
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 24
- 239000000654 additive Substances 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 20
- 239000004810 polytetrafluoroethylene Substances 0.000 description 20
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- 238000007792 addition Methods 0.000 description 18
- 239000006227 byproduct Substances 0.000 description 18
- 229910052739 hydrogen Inorganic materials 0.000 description 18
- 229910052751 metal Inorganic materials 0.000 description 18
- 239000002184 metal Substances 0.000 description 18
- 241000209094 Oryza Species 0.000 description 16
- 235000007164 Oryza sativa Nutrition 0.000 description 16
- 230000008901 benefit Effects 0.000 description 16
- 239000008367 deionised water Substances 0.000 description 16
- 229910021641 deionized water Inorganic materials 0.000 description 16
- 239000001257 hydrogen Substances 0.000 description 16
- 235000009566 rice Nutrition 0.000 description 16
- 239000003085 diluting agent Substances 0.000 description 14
- 150000002431 hydrogen Chemical class 0.000 description 14
- KTQDYGVEEFGIIL-UHFFFAOYSA-N n-fluorosulfonylsulfamoyl fluoride Chemical compound FS(=O)(=O)NS(F)(=O)=O KTQDYGVEEFGIIL-UHFFFAOYSA-N 0.000 description 14
- 239000000843 powder Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 230000002411 adverse Effects 0.000 description 12
- 230000009286 beneficial effect Effects 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 230000009257 reactivity Effects 0.000 description 11
- 230000000996 additive effect Effects 0.000 description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 10
- 229910052808 lithium carbonate Inorganic materials 0.000 description 10
- 230000014759 maintenance of location Effects 0.000 description 10
- 239000011255 nonaqueous electrolyte Substances 0.000 description 10
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 230000006870 function Effects 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 8
- INHCSSUBVCNVSK-UHFFFAOYSA-L lithium sulfate Inorganic materials [Li+].[Li+].[O-]S([O-])(=O)=O INHCSSUBVCNVSK-UHFFFAOYSA-L 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000001308 synthesis method Methods 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- KKQAVHGECIBFRQ-UHFFFAOYSA-N methyl propyl carbonate Chemical compound CCCOC(=O)OC KKQAVHGECIBFRQ-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- MHEBVKPOSBNNAC-UHFFFAOYSA-N potassium;bis(fluorosulfonyl)azanide Chemical compound [K+].FS(=O)(=O)[N-]S(F)(=O)=O MHEBVKPOSBNNAC-UHFFFAOYSA-N 0.000 description 6
- 239000003586 protic polar solvent Substances 0.000 description 6
- 238000011946 reduction process Methods 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
- CRPKPYRKDMWDPL-UHFFFAOYSA-N C(C)(=O)OCCCC.C(C)(=O)OC(C)=O Chemical compound C(C)(=O)OCCCC.C(C)(=O)OC(C)=O CRPKPYRKDMWDPL-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- 229910013870 LiPF 6 Inorganic materials 0.000 description 4
- 229910000990 Ni alloy Inorganic materials 0.000 description 4
- CQXADFVORZEARL-UHFFFAOYSA-N Rilmenidine Chemical compound C1CC1C(C1CC1)NC1=NCCO1 CQXADFVORZEARL-UHFFFAOYSA-N 0.000 description 4
- CHHOPPGAFVFXFS-UHFFFAOYSA-M [Li+].[O-]S(F)(=O)=O Chemical compound [Li+].[O-]S(F)(=O)=O CHHOPPGAFVFXFS-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
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- 238000006115 defluorination reaction Methods 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 230000001627 detrimental effect Effects 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
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- 238000009472 formulation Methods 0.000 description 4
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- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
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- 238000010189 synthetic method Methods 0.000 description 4
- RBTVSNLYYIMMKS-UHFFFAOYSA-N tert-butyl 3-aminoazetidine-1-carboxylate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)N1CC(N)C1 RBTVSNLYYIMMKS-UHFFFAOYSA-N 0.000 description 4
- ODNBVEIAQAZNNM-UHFFFAOYSA-N 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)ethanone Chemical compound C1=CC(Cl)=NN2C(C(=O)C)=CN=C21 ODNBVEIAQAZNNM-UHFFFAOYSA-N 0.000 description 2
- DSMUTQTWFHVVGQ-UHFFFAOYSA-N 4,5-difluoro-1,3-dioxolan-2-one Chemical compound FC1OC(=O)OC1F DSMUTQTWFHVVGQ-UHFFFAOYSA-N 0.000 description 2
- GUNJVIDCYZYFGV-UHFFFAOYSA-K Antimony trifluoride Inorganic materials F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 239000002000 Electrolyte additive Substances 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
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- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
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- BRCWHGIUHLWZBK-UHFFFAOYSA-K bismuth;trifluoride Chemical compound F[Bi](F)F BRCWHGIUHLWZBK-UHFFFAOYSA-K 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 2
- AXZAYXJCENRGIM-UHFFFAOYSA-J dipotassium;tetrabromoplatinum(2-) Chemical compound [K+].[K+].[Br-].[Br-].[Br-].[Br-].[Pt+2] AXZAYXJCENRGIM-UHFFFAOYSA-J 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
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- ZPBVUMUIOIGYRV-UHFFFAOYSA-N ethyl trifluoromethyl carbonate Chemical compound CCOC(=O)OC(F)(F)F ZPBVUMUIOIGYRV-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
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- PVMUVDSEICYOMA-UHFFFAOYSA-N n-chlorosulfonylsulfamoyl chloride Chemical compound ClS(=O)(=O)NS(Cl)(=O)=O PVMUVDSEICYOMA-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910001487 potassium perchlorate Inorganic materials 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
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- 241000894007 species Species 0.000 description 2
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
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- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 2
- 238000011179 visual inspection Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 229910012424 LiSO 3 Inorganic materials 0.000 description 1
Images
Classifications
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- 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
- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
- C01B21/086—Compounds containing nitrogen and non-metals and optionally metals containing one or more sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/34—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfuric acids
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- 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
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/80—Compositional purity
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2300/00—Electrolytes
- H01M2300/0017—Non-aqueous electrolytes
- H01M2300/0025—Organic electrolyte
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Electrochemistry (AREA)
- Manufacturing & Machinery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Secondary Cells (AREA)
Applications Claiming Priority (11)
Application Number | Priority Date | Filing Date | Title |
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US201862768447P | 2018-11-16 | 2018-11-16 | |
US62/768,447 | 2018-11-16 | ||
US201962840949P | 2019-04-30 | 2019-04-30 | |
US62/840,949 | 2019-04-30 | ||
US201962883177P | 2019-08-06 | 2019-08-06 | |
US201962883178P | 2019-08-06 | 2019-08-06 | |
US62/883,178 | 2019-08-06 | ||
US62/883,177 | 2019-08-06 | ||
US16/570,262 | 2019-09-13 | ||
US16/570,262 US10926190B2 (en) | 2018-11-16 | 2019-09-13 | Purified lithium bis(fluorosulfonyl)imide (LiFSI) products, methods of purifying crude LiFSI, and uses of purified LiFSI products |
PCT/IB2019/059852 WO2020100115A1 (en) | 2018-11-16 | 2019-11-15 | Processes for removing reactive solvent from lithium bis(fluorosulfonyl)imide (lifsi) using organic solvents that are stable toward anodes in lithium-ion and lithium-metal batteries |
Publications (2)
Publication Number | Publication Date |
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JP2022507458A true JP2022507458A (ja) | 2022-01-18 |
JP7555921B2 JP7555921B2 (ja) | 2024-09-25 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2021526413A Active JP7555921B2 (ja) | 2018-11-16 | 2019-11-15 | リチウムイオン電池およびリチウム金属電池のアノードに対して安定である有機溶媒を使用して、リチウムビス(フルオロスルホニル)イミド(lifsi)から反応性溶媒を除去するためのプロセス |
Country Status (5)
Country | Link |
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JP (1) | JP7555921B2 (de) |
KR (1) | KR20210077773A (de) |
CN (1) | CN113015692A (de) |
DE (1) | DE112019005761B4 (de) |
WO (1) | WO2020100115A1 (de) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
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KR102168118B1 (ko) | 2012-03-14 | 2020-10-21 | 이준 파마슈티컬스 리미티드 | 질병 치료를 위한 신규한 방법 및 조성물 |
CN116390894A (zh) * | 2020-09-10 | 2023-07-04 | 索尔维公司 | 双(氟磺酰基)酰亚胺盐的纯化 |
JPWO2023054244A1 (de) * | 2021-09-29 | 2023-04-06 | ||
EP4242173A1 (de) * | 2022-03-11 | 2023-09-13 | Specialty Operations France | Reingung von wasserstoff-bis(fluorsulfonyl)imid |
WO2023202919A1 (en) * | 2022-04-21 | 2023-10-26 | Specialty Operations France | Process for purifying a lithium salt of bis(fluorosulfonyl)imide |
WO2023202918A1 (en) * | 2022-04-21 | 2023-10-26 | Specialty Operations France | Process for manufacture lithium salt of bis(fluorosulfonyl)imide in solid form |
WO2023202920A1 (en) * | 2022-04-21 | 2023-10-26 | Specialty Operations France | Process for manufacture lithium salt of bis(fluorosulfonyl)imide in solid form |
CN115367718B (zh) | 2022-08-31 | 2023-03-24 | 安徽新宸新材料有限公司 | 一种双氟磺酰亚胺锂的提纯方法 |
CN116022748B (zh) * | 2022-12-16 | 2024-02-27 | 山东惟普新能源有限公司 | 一种含水双氟磺酰亚胺锂的除水方法 |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
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CN105731399A (zh) * | 2016-04-29 | 2016-07-06 | 多氟多化工股份有限公司 | 一种双氟磺酰亚胺锂的制备方法 |
JP2016171080A (ja) * | 2011-09-30 | 2016-09-23 | 株式会社日本触媒 | 電解液及びその製造方法、並びに、これを用いた蓄電デバイス |
CN106241757A (zh) * | 2016-07-27 | 2016-12-21 | 上海康鹏科技有限公司 | 一种双氟磺酰亚胺锂盐的制备方法 |
JP2017503740A (ja) * | 2013-12-05 | 2017-02-02 | ローディア オペレーションズ | ビス(フルオロスルホニル)イミド酸およびその塩の調製方法 |
WO2017090877A1 (ko) * | 2015-11-26 | 2017-06-01 | 임광민 | 리튬 비스(플루오르술포닐)이미드의 신규한 제조방법 |
CN106976849A (zh) * | 2017-04-20 | 2017-07-25 | 江苏国泰超威新材料有限公司 | 一种双氟磺酰亚胺锂的提纯方法 |
WO2018104675A1 (fr) * | 2016-12-08 | 2018-06-14 | Arkema France | Procédé de séchage et de purification de lifsi |
US20180219260A1 (en) * | 2017-01-30 | 2018-08-02 | Synthio Chemicals, LLC | Method for drying electrolyte solution |
CN108373142A (zh) * | 2018-01-25 | 2018-08-07 | 广州理文科技有限公司 | 一种高纯度双(氟磺酰)亚胺锂的制备方法 |
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US6248883B1 (en) | 1998-07-31 | 2001-06-19 | Moltech Corporation | Methods of purifying lithium salts |
US20040058008A1 (en) * | 2002-09-20 | 2004-03-25 | Tarcha Peter J. | Microparticles having serum as a dispersing agent and process for their preparation and use |
CA2517248A1 (fr) * | 2005-08-29 | 2007-02-28 | Hydro-Quebec | Procede de purification d'un electrolyte, electrolyte ainsi obtenu et ses utilisations |
WO2011065502A1 (ja) * | 2009-11-27 | 2011-06-03 | 株式会社日本触媒 | フルオロスルホニルイミド塩およびフルオロスルホニルイミド塩の製造方法 |
CN105523970A (zh) | 2014-10-23 | 2016-04-27 | 浙江蓝天环保高科技股份有限公司 | 一种双(氟磺酰)亚胺锂的制备方法 |
FR3059993A1 (fr) * | 2016-12-08 | 2018-06-15 | Arkema France | Procede de sechage et de purification du sel de lithium de bis(fluorosulfonyl)imide |
-
2019
- 2019-11-15 DE DE112019005761.8T patent/DE112019005761B4/de active Active
- 2019-11-15 KR KR1020217016445A patent/KR20210077773A/ko not_active Application Discontinuation
- 2019-11-15 CN CN201980075522.9A patent/CN113015692A/zh active Pending
- 2019-11-15 JP JP2021526413A patent/JP7555921B2/ja active Active
- 2019-11-15 WO PCT/IB2019/059852 patent/WO2020100115A1/en active Application Filing
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2016171080A (ja) * | 2011-09-30 | 2016-09-23 | 株式会社日本触媒 | 電解液及びその製造方法、並びに、これを用いた蓄電デバイス |
JP2017503740A (ja) * | 2013-12-05 | 2017-02-02 | ローディア オペレーションズ | ビス(フルオロスルホニル)イミド酸およびその塩の調製方法 |
WO2017090877A1 (ko) * | 2015-11-26 | 2017-06-01 | 임광민 | 리튬 비스(플루오르술포닐)이미드의 신규한 제조방법 |
CN105731399A (zh) * | 2016-04-29 | 2016-07-06 | 多氟多化工股份有限公司 | 一种双氟磺酰亚胺锂的制备方法 |
CN106241757A (zh) * | 2016-07-27 | 2016-12-21 | 上海康鹏科技有限公司 | 一种双氟磺酰亚胺锂盐的制备方法 |
WO2018104675A1 (fr) * | 2016-12-08 | 2018-06-14 | Arkema France | Procédé de séchage et de purification de lifsi |
US20180219260A1 (en) * | 2017-01-30 | 2018-08-02 | Synthio Chemicals, LLC | Method for drying electrolyte solution |
CN106976849A (zh) * | 2017-04-20 | 2017-07-25 | 江苏国泰超威新材料有限公司 | 一种双氟磺酰亚胺锂的提纯方法 |
CN108373142A (zh) * | 2018-01-25 | 2018-08-07 | 广州理文科技有限公司 | 一种高纯度双(氟磺酰)亚胺锂的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN113015692A (zh) | 2021-06-22 |
KR20210077773A (ko) | 2021-06-25 |
DE112019005761T5 (de) | 2021-08-05 |
WO2020100115A1 (en) | 2020-05-22 |
JP7555921B2 (ja) | 2024-09-25 |
DE112019005761B4 (de) | 2024-09-26 |
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