CN113247871B - Preparation method of lithium bis (fluorosulfonyl) imide - Google Patents
Preparation method of lithium bis (fluorosulfonyl) imide Download PDFInfo
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- CN113247871B CN113247871B CN202110623551.3A CN202110623551A CN113247871B CN 113247871 B CN113247871 B CN 113247871B CN 202110623551 A CN202110623551 A CN 202110623551A CN 113247871 B CN113247871 B CN 113247871B
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- CN
- China
- Prior art keywords
- fluorosulfonyl
- imide
- bis
- lithium
- lithium bis
- Prior art date
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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 34
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 39
- -1 lithium halide Chemical class 0.000 claims abstract description 28
- 238000001914 filtration Methods 0.000 claims abstract description 22
- 238000003756 stirring Methods 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 14
- 239000012043 crude product Substances 0.000 claims abstract description 13
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 13
- 239000012454 non-polar solvent Substances 0.000 claims abstract description 13
- KTQDYGVEEFGIIL-UHFFFAOYSA-N n-fluorosulfonylsulfamoyl fluoride Chemical compound FS(=O)(=O)NS(F)(=O)=O KTQDYGVEEFGIIL-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 239000012065 filter cake Substances 0.000 claims abstract description 9
- 239000003513 alkali Substances 0.000 claims abstract description 8
- 238000002386 leaching Methods 0.000 claims abstract description 7
- 238000001816 cooling Methods 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
- 239000000047 product Substances 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 10
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 239000003495 polar organic solvent Substances 0.000 claims description 9
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 8
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 5
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 4
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 claims description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 4
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 claims description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 claims description 3
- PPFAPKNCEXDZNN-UHFFFAOYSA-N N=[SH2].F.F Chemical compound N=[SH2].F.F PPFAPKNCEXDZNN-UHFFFAOYSA-N 0.000 claims description 3
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 3
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- FEKGWIHDBVDVSM-UHFFFAOYSA-N 1,1,1,2-tetrachloropropane Chemical compound CC(Cl)C(Cl)(Cl)Cl FEKGWIHDBVDVSM-UHFFFAOYSA-N 0.000 claims description 2
- AVGQTJUPLKNPQP-UHFFFAOYSA-N 1,1,1-trichloropropane Chemical compound CCC(Cl)(Cl)Cl AVGQTJUPLKNPQP-UHFFFAOYSA-N 0.000 claims description 2
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- 229960001701 chloroform Drugs 0.000 claims description 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 2
- 229940011051 isopropyl acetate Drugs 0.000 claims description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 2
- 229940090181 propyl acetate Drugs 0.000 claims description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 1
- 238000009776 industrial production Methods 0.000 abstract description 3
- 238000010992 reflux Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000012535 impurity Substances 0.000 description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- 239000012295 chemical reaction liquid Substances 0.000 description 6
- 229910003002 lithium salt Inorganic materials 0.000 description 6
- 159000000002 lithium salts Chemical class 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 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 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 239000003792 electrolyte Substances 0.000 description 4
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 4
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 208000012839 conversion disease Diseases 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 238000004321 preservation Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910001416 lithium ion Inorganic materials 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 125000005463 sulfonylimide group Chemical group 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- AXZAYXJCENRGIM-UHFFFAOYSA-J dipotassium;tetrabromoplatinum(2-) Chemical compound [K+].[K+].[Br-].[Br-].[Br-].[Br-].[Pt+2] AXZAYXJCENRGIM-UHFFFAOYSA-J 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 229910001487 potassium perchlorate Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- H01M10/0561—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of inorganic materials only
- H01M10/0562—Solid materials
-
- 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
- C01P2006/40—Electric properties
-
- 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
-
- 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)
- Engineering & Computer Science (AREA)
- Electrochemistry (AREA)
- Organic Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Secondary Cells (AREA)
Abstract
The invention discloses a preparation method of lithium bis (fluorosulfonyl) imide, which comprises the steps of dropwise adding bis (fluorosulfonyl) imide into anhydrous lithium halide under the condition of mixing and stirring with a non-polar solvent, and absorbing tail gas by using alkali liquor; after the dropwise addition is finished, continuously reacting at 0-60 ℃ for 1-12 hours, cooling to room temperature, dropwise adding an organic alkaline compound, and adjusting the pH of the reaction solution to 5-8; filtering, leaching the filter cake by adopting a nonpolar solvent to obtain a crude product of the lithium bis (fluorosulfonyl) imide. The invention has the advantages of mild reaction, simple process and low cost, and is suitable for industrial production.
Description
Technical Field
The invention belongs to the technical field of preparation of electrolyte in lithium ion battery electrolyte, and particularly relates to a preparation method of lithium bis (fluorosulfonyl) imide.
Background
Lithium bis (fluorosulfonyl) imide (LiFSI) is an electrolyte lithium salt of a lithium ion battery, has the advantages of high and low temperature resistance, stable structure, difficult hydrolysis and the like, is superior to lithium hexafluorophosphate which is widely applied at present in application safety and stability, and is an ideal substitute product which is expected to replace lithium hexafluorophosphate as a main electrolyte lithium salt in the future. At present, the preparation technology of lithium bis (fluorosulfonyl) imide, which is publicly reported at home and abroad, mainly has two routes:
one is double decomposition reaction of potassium bifluoro sulfonyl imide salt and organic lithium salt of lithium tetrafluoroborate or lithium perchlorate in non-proton organic solvent to produce lithium bifluoro sulfonyl imide and potassium tetrafluoroborate or potassium perchlorate, filtering to separate, evaporating to concentrate and crystallizing to obtain the product. The defects are as follows: 1) the double decomposition reaction is difficult to complete, and the residual potassium ions in the product are high; 2) lithium tetrafluoroborate and lithium perchlorate which are used as reaction raw materials have higher solubility in a reaction organic solvent and are difficult to separate, and the obtained product often contains part of unreacted or excessive raw materials and has low purity; 3) the organic lithium salts such as lithium tetrafluoroborate or lithium perchlorate are high in price, which results in high manufacturing cost; lithium perchlorate is an explosive compound, brings certain safety risk and is not suitable for industrial production.
The other route is that the bifluoro-sulfonyl imide and basic lithium salt such as lithium hydroxide or lithium carbonate are subjected to acid-base neutralization reaction in a low-polarity organic solvent to generate the bifluoro-sulfonyl imide lithium and water. And then thionyl chloride is added to react with water to generate hydrogen chloride and sulfur dioxide gas so as to achieve the aim of removing water. Filtering, separating solid from liquid, and further purifying to obtain the final product. The main defects are as follows: 1) the bis-fluorosulfonyl imide is a strong proton acid, and reacts violently with alkali to generate a large amount of heat. The reaction process needs refrigeration and low-temperature control, and the energy consumption is high; 2) the reaction is essentially acid-base neutralization reaction, generates water with equal mole, adopts thionyl chloride to remove water, is difficult to completely react, has longer reaction time and more three wastes. Meanwhile, the dehydration reaction process easily causes partial hydrolysis of the product, so that the water in the product remains, chloride ions and sulfate ions exceed the standard, and a high-quality product is difficult to obtain.
Disclosure of Invention
In order to solve the problems of the preparation process of the lithium bis (fluorosulfonyl) imide in the prior art, the invention aims to provide the preparation method of the lithium bis (fluorosulfonyl) imide, which has the advantages of mild reaction, simple process and low cost and is suitable for industrial production.
In order to achieve the purpose and achieve the technical effect, the invention adopts the following process:
a preparation method of lithium bis (fluorosulfonyl) imide is characterized in that under the condition of mixing and stirring anhydrous lithium halide salt and a nonpolar solvent, bis (fluorosulfonyl) imide is dropwise added, and tail gas is absorbed by alkali liquor; after the dropwise addition is finished, continuously reacting at 0-60 ℃ for 1-12 hours, cooling to room temperature, dropwise adding an organic alkaline compound, and adjusting the pH of the reaction solution to 5-8; filtering, leaching the filter cake by adopting a nonpolar solvent to obtain a crude product of the lithium bis (fluorosulfonyl) imide.
Further, the preparation method of the lithium bis (fluorosulfonyl) imide further comprises the steps of dissolving a crude lithium bis (fluorosulfonyl) imide product in an aprotic polar organic solvent, filtering to remove insoluble substances, concentrating the filtrate under reduced pressure, and adding a poor solvent for crystallization; filtering, washing and drying to obtain the high-purity lithium bis (fluorosulfonyl) imide product, wherein the purity of the lithium bis (fluorosulfonyl) imide is more than or equal to 99.70%, the water content is less than or equal to 30ppm, the acidity (calculated by HF) is less than or equal to 50ppm, the free chlorine is less than or equal to 10ppm, and the content of impurity ions such as metal potassium, sodium and the like is less than or equal to 5 ppm.
Further, the anhydrous lithium halide salt is one of anhydrous lithium chloride, anhydrous lithium fluoride or anhydrous lithium bromide; from the economic and environmental protection points of view, anhydrous lithium chloride and anhydrous lithium fluoride are preferred; from the viewpoint of the progress of the reaction, anhydrous lithium chloride is more preferable.
Further, the molar ratio of the anhydrous lithium halide salt to the bis-fluorosulfonyl imide is (1-1.1) to 1; anhydrous lithium halide salt and difluoride sulfimide are used in equivalent amount or lithium salt is slightly excessive, so that the sufficient reaction of the difluoride sulfimide is ensured.
Further, the nonpolar solvent is halogenated alkane selected from one or more of dichloromethane, trichloromethane, carbon tetrachloride, dichloroethane, trichloroethane, tetrachloroethane, dichloropropane, trichloropropane and tetrachloropropane; preferably dichloromethane and dichloroethane which are relatively less toxic, and more preferably, when the nonpolar solvent is dichloromethane, the reaction temperature is controlled to be 60 ℃ at reflux temperature.
Further, the addition amount of the nonpolar solvent is 1-5 times of the mass times of the bis-fluorosulfonyl imide.
The organic alkaline compound is a nitrogen-containing organic weak base, and is selected from one or a combination of more than two of triethylamine, tripropylamine, n-propylamine, isopropylamine, dipropylamine, butylamine, isobutylamine, tert-butylamine, hexylamine, octylamine, aniline, cyclohexylamine, pyridine and piperidine.
Further, the water content of the aprotic polar organic solvent is less than 1000ppm, preferably less than 500ppm, more preferably less than 300ppm, the aprotic polar organic solvent is an ester compound, a ketone compound, a nitrile compound or an ether compound, and is selected from one or a mixture of two or more of dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, propylene carbonate, methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, acetone, methyl ethyl ketone, acetonitrile, propionitrile, diethyl ether, isopropyl ether, methyl tert-butyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, 1, 4-dioxane, tetrahydrofuran or 2-methyltetrahydrofuran.
Further, the addition amount of the aprotic polar organic solvent is 0.8-5 times of the mass multiple of the crude product of the lithium bis (fluorosulfonyl) imide; the addition amount of the aprotic polar organic solvent is preferably 1-3 times of the mass of the crude product of the bis (fluorosulfonyl) imide lithium in terms of energy consumption, smooth filtering operation and the like.
Further, the poor solvent is selected from one or more of benzene, toluene, xylene, chlorobenzene, hexane, cyclohexane, heptane, octane, dichloromethane, dichloroethane, trichloroethane, tetrachloroethane, and petroleum ether.
The principle of the invention is as follows: the method adopts the steps that the bis-fluorosulfonyl imide is fully reacted with lithium halide salt, and then a proper amount of organic alkaline compound is added for reaction assistance, so that high reaction conversion rate can be obtained, and free fluorine, chloride ions and other acidic impurities in a complex reaction system can be obtained. After the dropwise addition of the bis (fluorosulfonyl) imide, the reaction system is kept at 0-60 ℃ for reaction. The reaction temperature is too low, and the reaction is slow; the reaction temperature is higher than 60 ℃, and the generated product is easy to be partially decomposed in an acid system. When the nonpolar solvent is dichloromethane, the reaction temperature is controlled to be 60 ℃ of reflux temperature under the condition of heat preservation. After the heat preservation reaction is finished, in order to further accelerate the reaction process and the reaction conversion rate, an organic alkaline compound is dropwise added into the reaction system, and the pH value of the reaction solution is adjusted to 5-8. The organic alkaline compound can be used as an acid-binding agent to generate a complex with hydrogen chloride, hydrogen fluoride or hydrogen bromide generated by the reaction, and the complex neutralizes free acid in the reaction system to promote the forward progress of the reaction. Meanwhile, the organic alkaline compound and the complex have better solubility in the halogenated alkane nonpolar solvent provided by the technical scheme, and the product lithium bis (fluorosulfonyl) imide is almost insoluble in the solvent, so that a better separation effect can be achieved by simple filtration. The chemical reaction in the technical scheme is an anhydrous system, so that the hydrolysis problems of reaction raw materials and target products under the conditions of temperature rise and acidity are fundamentally avoided. The organic alkali complex has higher solubility in the nonpolar halogenated alkane solvent provided by the technical scheme, the target product lithium bifluorosulfonyl imide is almost insoluble, and the removal is more thorough through solid-liquid separation and leaching after the reaction is finished.
The invention has the beneficial effects that: the preparation method of the lithium bis (fluorosulfonyl) imide provided by the invention has the advantages of mild reaction conditions, easiness in operation, less three wastes generation, environmental friendliness, capability of simply and conveniently obtaining a high-purity lithium bis (fluorosulfonyl) imide product with high technical indexes, capability of controlling residual moisture, free acid, fluoride ions, chloride ions, other impurities and the like in the lithium bis (fluorosulfonyl) imide product at a lower level, and higher reaction conversion rate and yield.
Detailed Description
The present invention will be described in further detail with reference to specific examples, so that the advantages of the present invention will be more apparent. It should be understood that the description is intended for purposes of illustration only and is not intended to limit the scope of the present disclosure. The experimental procedures, in which specific conditions are not specified, in the following examples are generally carried out according to conventional conditions or according to conditions recommended by the manufacturers. Unless otherwise indicated, all parts are parts by weight and all percentages are percentages by weight.
Example 1
42g (1 mol) of anhydrous lithium chloride was charged into a dry three-necked flask with stirring and condensing reflux apparatus under nitrogen atmosphere, 360g of methylene chloride was then added thereto, and stirring was turned on. 181g (1 mol) of bis (fluorosulfonyl) imide is added into a dry constant-pressure dropping funnel under a nitrogen atmosphere, the mixture is dropped into a flask at room temperature, acid tail gas escapes in the dropping process, and tail gas of a condensation reflux pipe is connected to an alkali liquor absorption device. After 1 hour, the dropwise addition is finished, the temperature is raised to about 40 ℃ for reflux, the reaction is stopped after 1 hour of continuous reaction, and the temperature is reduced to room temperature. And (3) measuring the pH value of the reaction liquid to be 1, slowly dropwise adding triethylamine into the reaction liquid while stirring, continuously detecting the pH value of the reaction liquid in the process, stopping dropwise adding until the pH value is 6-7, and continuously stirring for about 10 minutes. And filtering under the protection of nitrogen, and leaching a filter cake twice by using dichloromethane to obtain 178g of a solid crude product.
The crude product was added to 180g of dimethyl carbonate containing 95ppm of water under nitrogen, and dissolved with stirring. Filtering with 0.1 μm PTFE filter membrane to room temperature, concentrating the filtrate at 50 deg.C under reduced pressure for 5 hr, adding toluene 250g, stirring, cooling, crystallizing for 12 hr, filtering, and drying the filter cake under reduced pressure to obtain 173g of lithium bis (fluorosulfonyl) imide product with yield of 92.5%.
The detection shows that the purity of the product is 99.85 percent, the water content is 12ppm, the acidity (calculated by HF) is 15ppm, the free chlorine is 1.23ppm, and the impurity ions such as metal potassium, sodium and the like are less than 3 ppm.
Example 2
To a dry three-necked flask with stirring and condensing reflux apparatus was added 28.6g (1.1 mol) of anhydrous lithium fluoride under nitrogen atmosphere, and then 181g of dichloroethane was added thereto, and the stirring was turned on. 181g (1 mol) of bis (fluorosulfonyl) imide is added into a dry constant-pressure dropping funnel under a nitrogen atmosphere, the mixture is dropped into a flask at room temperature, and tail gas of a condensation reflux pipe is connected to an alkali liquor absorption device. After 1 hour, the dropwise addition is finished, the temperature is raised to 55-60 ℃, the reaction is continued for 12 hours, and the temperature is stopped to be reduced to the room temperature. And (3) measuring the pH value of the reaction liquid to be 1, slowly dropwise adding dipropylamine into the reaction liquid while stirring, continuously detecting the pH value of the reaction liquid in the process, stopping dropwise adding until the pH value is 5-6, and continuously stirring for about 10 minutes. Filtering under the protection of nitrogen, and leaching the filter cake twice with dichloroethane to obtain 166g of a solid crude product.
Under nitrogen atmosphere, the crude product was added to a mixed solvent of 160g of diethyl ether and 160g of ethylene glycol diethyl ether, the water content of the mixed solvent was 126ppm, and the mixture was dissolved with stirring. Filtering with 0.1 μm PTFE filter membrane to room temperature, concentrating the filtrate at 60 deg.C under reduced pressure for 6 hr, adding 300g dichloroethane, stirring, cooling, crystallizing for 12 hr, filtering, and drying the filter cake under reduced pressure to obtain 158g of lithium bis (fluorosulfonyl) imide product with yield of 84.5%.
The detection shows that the purity of the product is 99.76%, the water content is 18ppm, the acidity (calculated by HF) is 21ppm, the free chlorine is 0.69ppm, and the impurity ions such as metal potassium, sodium and the like are less than 2 ppm.
Example 3
To a dry three-necked flask with stirring and condensing reflux apparatus, 46g (1.1 mol) of anhydrous lithium chloride was charged under nitrogen atmosphere, and 540g of dichloroethane was subsequently added thereto, and stirring was turned on. 181g (1 mol) of bis (fluorosulfonyl) imide is added into a dry constant-pressure dropping funnel under a nitrogen atmosphere, the mixture is dropped into a flask at room temperature, acid tail gas escapes in the dropping process, and tail gas of a condensation reflux pipe is connected to an alkali liquor absorption device. After 1 hour, the dropwise addition is finished, the reaction is carried out at the temperature of 0-8 ℃ for 12 hours, and the pH of the reaction solution is measured to be 1. Slowly dropwise adding pyridine into the reaction solution under stirring, continuously detecting the pH value of the reaction solution in the process, stopping dropwise adding until the pH value is 7-8, and continuously stirring for about 30 minutes. Filtering under the protection of nitrogen, and leaching the filter cake twice with dichloroethane to obtain 173g of a solid crude product.
The above crude product was added to 340g of acetonitrile containing 280ppm of acetonitrile in water under nitrogen atmosphere, and dissolved with stirring. And (3) filtering the solution to room temperature by using a 0.1-micron PTFE filter membrane, concentrating the filtrate at 45-50 ℃ under reduced pressure for 4 hours, adding 350g of heptane into the concentrated solution, stirring the solution, cooling the solution for crystallization for 12 hours, filtering the solution, and drying a filter cake under reduced pressure to obtain 171g of lithium bis (fluorosulfonyl) imide product with the yield of 91.4%.
The detection proves that the purity of the product is 99.92 percent, the water content is 28ppm, the acidity (calculated by HF) is 23ppm, the free chlorine is 0.72ppm, and the impurity ions such as metal potassium, sodium and the like are less than 3 ppm.
Comparative examples
The same materials weight, proportion and operation conditions as those in example 1, after the completion of the heat preservation reaction of the bis (fluorosulfonyl) imide, triethylamine was not added dropwise thereto, and the crude product (155 g) was obtained by direct filtration and elution.
The operation conditions of the purification steps are completely the same, and 131g of lithium bis (fluorosulfonyl) imide product is obtained after concentration, crystallization, filtration and drying, and the yield is 70%.
The detection shows that the product has the purity of 99.81 percent, the water content of 16ppm, the acidity (calculated by HF) of 56ppm, the free chlorine of 18ppm, and the impurity ions such as metal potassium, sodium and the like which are less than 5 ppm.
It will be appreciated that various alterations and modifications of the invention will occur to those skilled in the art upon reading the above teachings, and that such equivalents are intended to fall within the scope of the invention as defined by the appended claims.
Claims (5)
1. A preparation method of lithium bis (fluorosulfonyl) imide is characterized by comprising the following steps: dropwise adding difluoride sulfimide under the condition of mixing and stirring anhydrous lithium halide salt and a non-polar solvent, and absorbing tail gas by adopting alkali liquor; after the dropwise addition is finished, continuously reacting at 0-60 ℃ for 1-12 hours, cooling to room temperature, dropwise adding an organic alkaline compound, and adjusting the pH of the reaction solution to 5-8; filtering, leaching a filter cake by using a non-polar solvent to obtain a crude product of the lithium bis (fluorosulfonyl) imide; the molar ratio of the anhydrous lithium halide salt to the bis (fluorosulfonyl) imide is (1-1.1) to 1; the nonpolar solvent is halogenated alkane selected from one or more of dichloromethane, trichloromethane, carbon tetrachloride, dichloroethane, trichloroethane, tetrachloroethane, dichloropropane, trichloropropane and tetrachloropropane; the addition amount of the nonpolar solvent is 1-5 times of the mass multiple of the bis (fluorosulfonyl) imide; the organic alkaline compound is nitrogen-containing organic weak base selected from one or a combination of more than two of triethylamine, tripropylamine, n-propylamine, isopropylamine, dipropylamine, butylamine, isobutylamine, tert-butylamine, hexylamine, octylamine, aniline, cyclohexylamine, pyridine and piperidine.
2. The method for preparing lithium bis (fluorosulfonyl) imide according to claim 1, wherein: the preparation method of the lithium bis (fluorosulfonyl) imide further comprises the steps of dissolving a crude lithium bis (fluorosulfonyl) imide product in an aprotic polar organic solvent, filtering to remove insoluble substances, concentrating the filtrate under reduced pressure, and adding a poor solvent for crystallization; and filtering, washing and drying to obtain the high-purity lithium bis (fluorosulfonyl) imide product.
3. The method for preparing lithium bis (fluorosulfonyl) imide according to claim 1 or 2, wherein: the anhydrous lithium halide salt is one of anhydrous lithium chloride, anhydrous lithium fluoride or anhydrous lithium bromide.
4. The method for preparing lithium bis (fluorosulfonyl) imide according to claim 2, wherein: the water content of the aprotic polar organic solvent is less than 1000ppm, the aprotic polar organic solvent is an ester compound, a ketone compound, a nitrile compound or an ether compound, and is selected from one or a mixture of more than two of dimethyl carbonate, diethyl carbonate, methyl ethyl carbonate, propylene carbonate, methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, acetone, methyl ethyl ketone, butanone, acetonitrile, propionitrile, diethyl ether, isopropyl ether, methyl tert-butyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, 1, 4-dioxane, tetrahydrofuran or 2-methyltetrahydrofuran; the addition amount of the aprotic polar organic solvent is 0.8-5 times of the mass multiple of the crude product of the bis (fluorosulfonyl) imide.
5. The method for preparing lithium bis (fluorosulfonyl) imide according to claim 2, wherein: the poor solvent is one or more selected from benzene, toluene, xylene, chlorobenzene, hexane, cyclohexane, heptane, octane, dichloromethane, dichloroethane, trichloroethane, tetrachloroethane or petroleum ether.
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| CN115535995A (en) * | 2022-11-03 | 2022-12-30 | 江苏华盛锂电材料股份有限公司 | Purification method of lithium difluorophosphate |
| CN116462165B (en) * | 2023-04-28 | 2025-03-14 | 湖北兴发化工集团股份有限公司 | Preparation method of lithium bis (fluorosulfonyl) imide |
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