CN108373142A - A kind of high-purity is double（Fluorine sulphonyl）The preparation method of imine lithium - Google Patents
A kind of high-purity is double（Fluorine sulphonyl）The preparation method of imine lithium Download PDFInfo
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- CN108373142A CN108373142A CN201810074841.5A CN201810074841A CN108373142A CN 108373142 A CN108373142 A CN 108373142A CN 201810074841 A CN201810074841 A CN 201810074841A CN 108373142 A CN108373142 A CN 108373142A
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- Prior art keywords
- bis
- fluorine sulphonyl
- lithium
- purity
- preparation
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- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 75
- 239000011737 fluorine Substances 0.000 title claims abstract description 75
- 150000002466 imines Chemical class 0.000 title claims abstract description 52
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 229910052744 lithium Inorganic materials 0.000 title claims abstract description 40
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 44
- -1 amine salts Chemical class 0.000 claims abstract description 27
- 239000012141 concentrate Substances 0.000 claims abstract description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000003960 organic solvent Substances 0.000 claims abstract description 15
- 239000012043 crude product Substances 0.000 claims abstract description 10
- 239000011261 inert gas Substances 0.000 claims abstract description 10
- 238000005649 metathesis reaction Methods 0.000 claims abstract description 10
- 229910003002 lithium salt Inorganic materials 0.000 claims abstract description 8
- 150000002148 esters Chemical class 0.000 claims abstract description 6
- 150000002576 ketones Chemical class 0.000 claims abstract description 6
- 150000001298 alcohols Chemical class 0.000 claims abstract description 5
- 150000002825 nitriles Chemical class 0.000 claims abstract description 5
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims abstract description 4
- 239000013078 crystal Substances 0.000 claims abstract description 4
- 150000002170 ethers Chemical class 0.000 claims abstract description 4
- 239000000047 product Substances 0.000 claims abstract description 4
- 239000002994 raw material Substances 0.000 claims abstract description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 10
- 235000019441 ethanol Nutrition 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 6
- 241000255964 Pieridae Species 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 229910021645 metal ion Inorganic materials 0.000 claims description 5
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 239000012535 impurity Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-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
- 238000001914 filtration Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 229910021654 trace metal Inorganic materials 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-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 group CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-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
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- SIXOAUAWLZKQKX-UHFFFAOYSA-N carbonic acid;prop-1-ene Chemical compound CC=C.OC(O)=O SIXOAUAWLZKQKX-UHFFFAOYSA-N 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-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
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001455 metallic ions Chemical class 0.000 claims description 2
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-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
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 238000005292 vacuum distillation Methods 0.000 claims description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000005864 Sulphur Substances 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229940043232 butyl acetate Drugs 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000012295 chemical reaction liquid Substances 0.000 claims 1
- 229940093499 ethyl acetate Drugs 0.000 claims 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims 1
- 229940074391 gallic acid Drugs 0.000 claims 1
- 235000004515 gallic acid Nutrition 0.000 claims 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 4
- 239000000758 substrate Substances 0.000 abstract description 3
- 238000001035 drying Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000007787 solid Substances 0.000 description 19
- 239000000706 filtrate Substances 0.000 description 18
- 238000005352 clarification Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 229910001415 sodium ion Inorganic materials 0.000 description 7
- 238000013019 agitation Methods 0.000 description 6
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 6
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 6
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 description 6
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 5
- 239000003792 electrolyte Substances 0.000 description 5
- 229910001416 lithium ion Inorganic materials 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 159000000002 lithium salts Chemical class 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 2
- 229910010941 LiFSI Inorganic materials 0.000 description 2
- 229910001290 LiPF6 Inorganic materials 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- SLGKFAQSCDYULE-UHFFFAOYSA-N lithium;4-methylbenzenesulfonic acid Chemical compound [Li].CC1=CC=C(S(O)(=O)=O)C=C1 SLGKFAQSCDYULE-UHFFFAOYSA-N 0.000 description 2
- VDVLPSWVDYJFRW-UHFFFAOYSA-N lithium;bis(fluorosulfonyl)azanide Chemical compound [Li+].FS(=O)(=O)[N-]S(F)(=O)=O VDVLPSWVDYJFRW-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VKEQBMCRQDSRET-UHFFFAOYSA-N Methylone Chemical compound CNC(C)C(=O)C1=CC=C2OCOC2=C1 VKEQBMCRQDSRET-UHFFFAOYSA-N 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 230000003301 hydrolyzing effect Effects 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
- WDGKXRCNMKPDSD-UHFFFAOYSA-N lithium;trifluoromethanesulfonic acid Chemical compound [Li].OS(=O)(=O)C(F)(F)F WDGKXRCNMKPDSD-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 229910001487 potassium perchlorate Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229940117958 vinyl acetate Drugs 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Secondary Cells (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
It is double that the invention discloses a kind of high-purities（Fluorine sulphonyl）The preparation method of imine lithium, includes the following steps：With bis- (fluorine sulphonyl) inferior amine salts (MFSI) of purity >=99.9% for raw material, in esters, ketone, alcohols, ethers, carbonates or nitrile reaction dissolvent, with Sulfonic Lithium (RSO3Li) metathesis reaction obtains bis- (fluorine sulphonyl) imines lithium salts crude product solutions, wherein the Sulfonic Lithium (RSO3Li the R in) is Ar or CnHxFyOz, wherein n >=1, x, y, z >=0 is adjusted the R according to solubility of bis- (fluorine sulphonyl) inferior amine salts (MFSI) in reaction dissolvent；Crude product solution is filtered, concentrates, ether organic solvent is added into concentrate, is filtered, low polar non-proton organic solvent is added into concentrate, stands still for crystals and is drying to obtain, step made above carries out waterless operation under the protection of inert gas for concentration.Preparation method provided by the invention have it is simple for process, substrate selects feature extensive, at low cost and high product purity.
Description
Technical field
The present invention relates to a kind of preparation methods of bis- (fluorine sulphonyl) imine lithiums of high-purity, belong to chemosynthesis technical field.
Background technology
Bis- (fluorine sulphonyl) imine lithiums can be used for multiple fields, for example, can be used as lithium-ion battery electrolytes additive, improve
Cycle performance of lithium ion battery can also be used as one-shot battery and be used with electrolyte；It can be used as polymerisation catalysts；Also it can be used
It is used in antistatic agent in industrial circle.
Existing result of study shows lithium hexafluoro phosphate (LiPF6) it is current more successful commercial lithium salt electrolyte, but
It is LiPF6Thermostabilization and chemical stability are poor, and bis- (fluorine sulphonyl) imine lithiums are compared with regard to having better stability, and its low temperature
It has excellent performance, hydrolytic stability is good, therefore the potential lithium hexafluoro phosphate that substitutes of bis- (fluorine sulphonyl) imine lithiums becomes the two of a new generation
Secondary lithium ion battery.Bis- (fluorine sulphonyl) imine lithiums therefore, it is possible to simply prepare high-purity become lithium ion battery in recent years
The Main way in electrolyte field.
In the prior art, mainly there is following report for the preparation of bis- (fluorine sulphonyl) imine lithiums：
For the preparation of bis- (fluorine sulphonyl) imine lithiums, what is appeared in the newspapers both at home and abroad is mainly (fluorine sulphonyl) imines bis- at low temperature
Bis- (fluorine sulphonyl) imine lithium (CN 201510261089, CN 201610288440, CN are obtained with alkaline, lithium reactant salt
103664712A、EP 2415757、EP 2439173、US 20120020867).This method operating condition is harsh, due to soda acid
Neutralize can very exothermic, so needing to react at low temperature, or even to be carried out at -78 DEG C, thus it is this operation not there is only
Security risk, and operation is more consumed energy.
In addition to obtaining bis- (fluorine sulphonyl) imine lithiums, Chinese patent (CN 101747242) report in the way of acid-base neutralization
Occur metathesis reaction in acetonitrile using bis- (fluorine sulphonyl) imines potassium and lithium perchlorate and obtains bis- (fluorine sulphonyl) imine lithiums.It should
Method needs operate in vacuum tank so that operation difficulty increases, it is also difficult to ensure that the reaction was complete, cannot get the double of high-purity
(fluorine sulphonyl) imine lithium.
Chinese patent (CN 105523970A) also reports bis- (fluorine sulphonyl) imine metal salt using purity >=99.9%
It is reacted with LiBF4 or lithium perchlorate for raw material, bis- (fluorine sulphonyl) imine lithiums of high-purity is obtained using purified crystals.But
This method LiBF4 first and lithium perchlorate cost are higher, and secondly lithium perchlorate makes the unsafe of reaction than relatively hazardous
To guarantee, more most important is to lead to bis- (fluorine sulphurs since LiBF4 and lithium perchlorate have prodigious solubility in a solvent
Acyl) remaining LiBF4 is difficult to detach with lithium perchlorate in imine lithium, and cause the metal ion in addition to lithium to be easy exceeded,
And it is not easily purified.
Invention content
The technical problem to be solved by the invention is to provide a kind of preparation method is simple, substrate selection it is extensive, at low cost with
And the preparation method of high bis- (fluorine sulphonyl) imine lithiums of product purity.
In order to solve the above technical problems, the technical solution adopted by the present invention is：
A kind of preparation method of bis- (fluorine sulphonyl) imine lithiums of high-purity, includes the following steps：
(1) with bis- (fluorine sulphonyl) inferior amine salts (MFSI) of purity >=99.9% for raw material, in esters, ketone, alcohols, ether
In class, carbonates or nitrile reaction dissolvent, with Sulfonic Lithium (RSO3Li) metathesis reaction obtains bis- (fluorine sulphonyl) imines lithium salts
Crude product solution, wherein the Sulfonic Lithium (RSO3Li the R in) is Ar or CnHxFyOz, wherein n >=1, x, y, z >=0, according to described
The R is adjusted in solubility of bis- (fluorine sulphonyl) inferior amine salts (MFSI) in reaction dissolvent；
(2) insoluble matter in above-mentioned bis- (fluorine sulphonyl) imines lithium salts crude product solutions is filtered, vacuum distillation concentration obtains double
(fluorine sulphonyl) imine lithium crude product concentrate；
(3) ether organic solvent, filtering and concentrating, at this time is added into above-mentioned bis- (fluorine sulphonyl) imine lithium crude product concentrates
Concentrate in low polar non-proton organic solvent is added, stand still for crystals, it is dry, obtain bis- (fluorine sulphurs of target product high-purity
Acyl) imine lithium；
Step made above carries out waterless operation under the protection of inert gas.
M in bis- (fluorine sulphonyl) inferior amine salts (MFSI) is monovalent metallic ion, bivalent metal ion or trivalent metal
Ion.
In step (1), moisture≤200ppm of the reaction dissolvent；The dosage of the reaction dissolvent be 50~
Bis- (fluorine sulphonyl) inferior amine salts of 200ml/10g；Bis- (fluorine sulphonyl) inferior amine salts and Sulfonic Lithium (RSO3Li mol ratio) be 1~
1.2：1~1.5.
In step (1), the dosage of the reaction dissolvent is bis- (fluorine sulphonyl) inferior amine salts of 50~100ml/10g；Bis- (fluorine
Sulphonyl) inferior amine salt and Sulfonic Lithium (RSO3Li mol ratio) is 1~1.2：1~1.2.
In step (1), esters are selected from methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, acetic acid
One or more combinations in isobutyl ester or vinylacetate；Carbonates are selected from dimethyl carbonate, diethyl carbonate, carbonic acid
One or more combinations in methyl ethyl ester, ethylene carbonate, propene carbonate；Nitrile is in acetonitrile, propionitrile or isopropyl nitrile
One or more combinations；Ketones solvent can be selected from acetone, butanone, methyl ethyl ketone, methyl tertbutyl ketone, crassitude
One or more combinations in ketone；Alcohols is selected from methanol, ethyl alcohol, propyl alcohol or the one or more combination of isopropanol；Ethers can
Selected from ether, propyl ether, isopropyl ether, butyl ether, isobutyl ether, tetrahydrofuran, t-butyl methyl ether, methyltetrahydrofuran, cyclopentyl methyl ether,
One or more combinations in dioxane, dioxolane or glycol dimethyl ether.
Sulfonic Lithium (the RSO3Li) purity >=99.9%, moisture≤0.1%, substance≤0.005% not soluble in water, total trace
Measure metals content impurity≤1000ppm.
Sulfonic Lithium (the RSO3Li) moisture≤200ppm, total trace metal impurity content≤200ppm.
Vacuum degree is 0.010~0.1MPa when concentration in step (2), and temperature is 10~60 DEG C, is concentrated into original solution volume
1/6~1/2.
Vacuum degree is 0.050~0.080MPa when concentration in step (2), temperature is 30~50 DEG C, is concentrated into original solution body
Long-pending 1/5~1/3.
Ether organic solvent dosage described in step (3) is 2~5 times of concentrate, and the low aprotic, polar is organic molten
One or more combinations of the agent in n-hexane, hexamethylene, pentamethylene, dichloromethane or chloroform.
The advantageous effect that the present invention is reached：
(1) present invention utilizes Sulfonic Lithium (RSO3Li) the platform as a metathesis exchange reaction, can be wide range
MFSI be replaced as LiFSI, to make the reaction substrate range of synthesis LiFSI increase, increase the alternative of synthetic route,
More easily purification obtains bis- (fluorine sulphonyl) imine lithiums of high-purity；
(2) since solubility of the different MFSI in different solvents has very big difference, metathesis exchange reaction
It needs to carry out in corresponding different preferred solvents, and single inorganic lithium salt such as LiBF4 etc., by the anion of itself
Characteristic is limited, and cannot ensure that under the precondition using multifarious solvent effective metathesis exchange reaction can be carried out, this
Sulfonic Lithium (RSO is adjusted by selection in invention3Li R is varied and controlled its (fluorine sulphonyl) inferior amine salt (MFSI) bis- with difference in)
Metathesis exchange reaction after the RSO that is generated3The effect of solubility and metathesis exchange reaction of the M in reaction dissolvent；
(3) Sulfonic Lithium (RSO3Li sulphonic acids (RSO) can be passed through3H) anti-with the generations such as lithium salts such as lithium hydroxide, lithium carbonate
It should generate, and sulfonic compound is at low cost, it is in large supply；
(4) sulfonate (RSO that metathesis exchange reaction obtains3M organic solvent) is not dissolved in, can be directly filtered to remove,
It is easy to operate；
(5) purity >=99.9% of bis- (fluorine sulphonyl) imine lithiums prepared by the present invention, Na ion concentration are≤20ppm, potassium
Ion concentration is≤20ppm, and chlorine ion concentration≤20ppm can be used in preparing lithium-ion battery electrolytes；
Specific implementation mode
The invention will be further described below.Following embodiment is only used for clearly illustrating the technical side of the present invention
Case, and not intended to limit the protection scope of the present invention.
Embodiment 1
Under inert gas shielding, by bis- (fluorine sulphonyl) imines potassium and 8.19g of 12g (0.055mol) purity >=99.9%
The p-methyl benzenesulfonic acid lithium of (0.046mol) purity >=99.9% is added in 250mL reaction bulbs, and 100mL first is added into reaction bulb
Alcohol, the solid in reaction bulb first dissolve change clarification, that is, are carved with a large amount of white solid and generate, and at 25 DEG C, keep mechanical agitation,
React 2h.After reaction, insoluble matter is filtered, filtrate, 600Pa heating under reduced pressure is taken to concentrate the filtrate to original volume to 40 DEG C
1/5, solution to be concentrated is cooled to room temperature, and t-butyl methyl ether 40mL is added into concentrate, a little insoluble matter is filtered, concentration filter
Liquid, then bad organic solvent dichloromethane 60mL is added dropwise and is recrystallized, it refilters, is dried in vacuo, obtains white solid powder
Bis- (fluorine sulphonyl) imine lithium 7.05g, yield 82%, purity >=99.9%.(testing result：Na+(≤1ppm)、K+(≤1ppm)、
Cl-(≤5ppm)、Fe2+(≤1ppm),19F NRM (400MHz, D2O)：51.9ppm).
Embodiment 2
Under inert gas shielding, by bis- (fluorine sulphonyl) imines sodium of 9.338g (0.046mol) purity >=99.9% with
The pyrovinic acid lithium of 4.69g (0.046mol) purity >=99.9% is added in 250mL reaction bulbs, is dissolved with the acetonitrile of 80mL,
Solid in reaction bulb first dissolves change clarification, that is, is carved with a large amount of white solid and generates, and at 25 DEG C, keeps mechanical agitation, instead
Answer 1.5h.After reaction, insoluble matter is filtered, filtrate, 600Pa heating under reduced pressure is taken to concentrate the filtrate to original volume to 40 DEG C
1/5, solution to be concentrated is cooled to room temperature, and ether 30mL is added into concentrate, a little insoluble matter is filtered, and concentrates filtrate, then drip
Add bad organic solvent dichloromethane 60mL to be recrystallized, refilter, is dried in vacuo, obtains bis- (the fluorine sulphurs of white solid powder
Acyl) imine lithium 7.31g, yield 85%, purity >=99.9%.(testing result：Na+(≤1ppm)、K+(≤1ppm)、Cl-(≤
5ppm)、Fe2+(≤1ppm),19F NRM (400MHz, D2O)：51.9ppm).
Embodiment 3
Under inert gas shielding, by bis- (fluorine sulphonyl) imines silver and 6.9g of 13.14g (0.046mol) purity >=99.9%
The trifluoromethanesulfonic acid lithium of (0.046mol) purity >=99.9% is added in 250mL reaction bulbs, is dissolved with the ethyl alcohol of 100mL, instead
It answers the solid in bottle first to dissolve change clarification, that is, is carved with a large amount of white solid and generates, at 25 DEG C, keep mechanical agitation, reaction
1.5h.After reaction, insoluble matter is filtered, filtrate, 600Pa heating under reduced pressure is taken to concentrate the filtrate to the 1/ of original volume to 40 DEG C
5, solution to be concentrated is cooled to room temperature, and the THF of 30mL is added into concentrate, a little insoluble matter is filtered, and concentrates filtrate, then be added dropwise
Bad organic solvent dichloromethane 60mL is recrystallized, and is refiltered, and it is bis- (fluorine sulphonyl) to obtain white solid powder for vacuum drying
Imine lithium 7.48g, yield 87%, purity >=99.9%.(testing result：Na+(≤1ppm)、K+(≤1ppm)、Cl-(≤
5ppm)、Fe2+(≤1ppm),19F NRM (400MHz, D2O)：51.9ppm).
Embodiment 4
Under inert gas shielding, by bis- (fluorine sulphonyl) imines potassium and 16.8g of 10g (0.046mol) purity >=99.9%
The nona-fluoro butyl group Sulfonic Lithium of (0.055mol) purity >=99.9% is added in 250mL reaction bulbs, with the dimethyl carbonate of 70mL
It dissolves, the solid in reaction bulb first dissolves change clarification, that is, is carved with a large amount of white solid and generates, and at 25 DEG C, machinery is kept to stir
It mixes, reacts 2h.After reaction, insoluble matter is filtered, filtrate, 600Pa heating under reduced pressure is taken to concentrate the filtrate to original volume to 40 DEG C
1/5, solution to be concentrated is cooled to room temperature, into concentrate be added t-butyl methyl ether 40mL, a little insoluble matter is filtered, concentration filter
Liquid, then bad organic molten dichloromethane 60mL is added dropwise and is recrystallized, it refilters, is dried in vacuo, it is double to obtain white solid powder
(fluorine sulphonyl) imine lithium 7.31g, yield 85%, purity >=99.9%.(testing result：Na+(≤1ppm)、K+(≤1ppm)、Cl-
(≤5ppm)、Fe2+(≤1ppm),19F NRM (400MHz, D2O)：51.9ppm).
Embodiment 5
Under inert gas shielding, by bis- (fluorine sulphonyl) imines caesiums of 14.40g (0.046mol) purity >=99.9% with
The p-methyl benzenesulfonic acid lithium of 8.19g (0.046mol) purity >=99.9% is added in 250mL reaction bulbs, molten with the methanol of 60mL
It solving, the solid in reaction bulb first dissolves change clarification, that is, is carved with a large amount of white insoluble matters generations and keeps mechanical agitation at 25 DEG C,
React 2h.After reaction, insoluble matter is filtered, filtrate, 600Pa heating under reduced pressure is taken to concentrate the filtrate to original volume to 40 DEG C
1/5, solution to be concentrated is cooled to room temperature, and t-butyl methyl ether 40mL is added into concentrate, a little insoluble matter is filtered, concentration filter
Liquid, then bad organic solvent dichloromethane 60mL is added dropwise and is recrystallized, it refilters, is dried in vacuo, obtains white solid powder
Bis- (fluorine sulphonyl) imine lithiums, yield 85%, purity >=99.9%.(testing result：Na+(≤1ppm)、K+(≤1ppm)、Cl-(≤
5ppm)、Fe2+(≤1ppm),19F NRM (400MHz, D2O)：51.9ppm).
Embodiment 6
Under inert gas shielding, by bis- (fluorine sulphonyl) imines potassium and 12.56g of 10g (0.046mol) purity >=99.9%
Tetra- fluoro- 1- (trifluoromethoxy) of the 1,2,2,2--ethanesulfonic acid lithium of (0.046mol) purity >=99.9% is added to 250mL reaction bulbs
In, it is dissolved with the methanol of 100mL, the solid in reaction bulb first dissolves change clarification, that is, is carved with a large amount of white solid and generates, 25
At DEG C, mechanical agitation is kept, reacts 2h.After reaction, insoluble matter is filtered, takes filtrate, 600Pa heating under reduced pressure, will to 40 DEG C
Filtrate is concentrated into the 1/5 of original volume, and solution to be concentrated is cooled to room temperature, and t-butyl methyl ether 40mL is added into concentrate, will be a little
Insoluble matter filters, and concentrates filtrate, then bad organic molten dichloromethane 60mL is added dropwise and is recrystallized, refilters, and is dried in vacuo, obtains
To bis- (fluorine sulphonyl) the imine lithium 7.31g of white solid powder, yield 85%, purity >=99.9%.(testing result：Na+(≤
1ppm)、K+(≤1ppm)、Cl-(≤5ppm)、Fe2+(≤1ppm),19F NRM (400MHz, D2O)：51.9ppm).
Comparative example
Under inert gas shielding, by bis- (fluorine sulphonyl) imines caesiums of 14.40g (0.046mol) purity >=99.9% with
The LiBF4 of 4.30g (0.046mol) purity >=99.9% is added in 250mL reaction bulbs, is dissolved with the acetonitrile of 70mL,
Solid in reaction bulb first dissolves change clarification, is not carved with apparent insoluble matter and generates.At 25 DEG C, mechanical agitation is kept,
React 2h.After reaction, only a small amount of white insoluble matter generates, and insoluble matter is filtered, filtrate, 600Pa heating under reduced pressure to 40 are taken
DEG C, the 1/5 of original volume is concentrated the filtrate to, solution to be concentrated is cooled to room temperature, and t-butyl methyl ether 40mL is added into concentrate, will
A little insoluble matter filtering, concentrates filtrate, then bad organic solvent dichloromethane 60mL is added dropwise, fails to obtain white solid powder.
Technical costs provided by the present invention is reasonable, safe, and step is simple, and post-processing way of purification is effectively easy,
Efficient, high yield, high-purity bis- (fluorine sulphonyl) imine lithiums can be obtained, be easy to implement industrialized production.
The above is only a preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, without departing from the technical principles of the invention, several improvement and deformations can also be made, these improvement and deformations
Also it should be regarded as protection scope of the present invention.
Claims (10)
1. a kind of preparation method of bis- (fluorine sulphonyl) imine lithiums of high-purity, characterized in that include the following steps：
(1) with bis- (fluorine sulphonyl) inferior amine salts (MFSI) of purity >=99.9% for raw material, in esters, ketone, alcohols, ethers, carbon
In esters of gallic acid or nitrile reaction dissolvent, with Sulfonic Lithium (RSO3Li) it is molten to obtain bis- (fluorine sulphonyl) imines lithium salts crude products for metathesis reaction
Liquid, wherein the Sulfonic Lithium (RSO3Li the R in) is Ar or CnHxFyOz, wherein n >=1, x, y, z >=0, according to bis- (fluorine sulphurs
Acyl) R is adjusted in solubility of the inferior amine salt (MFSI) in reaction dissolvent；
(2) insoluble matter in above-mentioned bis- (fluorine sulphonyl) imines lithium salts crude product solutions is filtered, vacuum distillation concentration obtains bis- (fluorine sulphurs
Acyl) imine lithium crude product concentrate；
(3) it is added ether organic solvent into above-mentioned bis- (fluorine sulphonyl) imine lithium crude product concentrates, filtering and concentrating is dense at this time
Low polar non-proton organic solvent is added in contracting liquid, stands still for crystals, dry, bis- (the fluorine sulphonyl) for obtaining target product high-purity are sub-
Amine lithium；
Step made above carries out waterless operation under the protection of inert gas.
2. a kind of preparation method of bis- (fluorine sulphonyl) imine lithiums of high-purity according to claim 1, characterized in that described double
M in (fluorine sulphonyl) inferior amine salt (MFSI) is monovalent metallic ion, bivalent metal ion or trivalent metal ion.
3. a kind of preparation method of bis- (fluorine sulphonyl) imine lithiums of high-purity according to claim 1, characterized in that step
(1) in, moisture≤200ppm of the reaction dissolvent；The dosage of the reaction dissolvent is bis- (the fluorine sulphurs of 50~200ml/10g
Acyl) inferior amine salt；Bis- (fluorine sulphonyl) inferior amine salts and Sulfonic Lithium (RSO3Li mol ratio) is 1~1.2：1~1.5.
4. a kind of preparation method of bis- (fluorine sulphonyl) imine lithiums of high-purity according to claim 3, characterized in that step
(1) in, the dosage of the reaction dissolvent is bis- (fluorine sulphonyl) inferior amine salts of 50~100ml/10g；Bis- (fluorine sulphonyl) inferior amine salts
With Sulfonic Lithium (RSO3Li mol ratio) is 1~1.2：1~1.2.
5. a kind of preparation method of bis- (fluorine sulphonyl) imine lithiums of high-purity according to claim 1, characterized in that step
(1) in, esters are selected from methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, isobutyl acetate or acetic acid
One or more combinations in vinyl acetate；Carbonates are selected from dimethyl carbonate, diethyl carbonate, methyl ethyl carbonate, carbonic acid
One or more combinations in vinyl acetate, propene carbonate；Nitrile is one or more in acetonitrile, propionitrile or isopropyl nitrile
Combination；Ketones solvent can be selected from acetone, butanone, methyl ethyl ketone, methyl tertbutyl ketone, one kind in methyl pyrrolidone or
A variety of combinations；Alcohols is selected from methanol, ethyl alcohol, propyl alcohol or the one or more combination of isopropanol；Ethers can be selected from ether, third
Ether, isopropyl ether, butyl ether, isobutyl ether, tetrahydrofuran, t-butyl methyl ether, methyltetrahydrofuran, cyclopentyl methyl ether, dioxane, two
One or more combinations in oxygen five rings or glycol dimethyl ether.
6. a kind of preparation method of bis- (fluorine sulphonyl) imine lithiums of high-purity according to claim 1, characterized in that the sulphur
Sour lithium (RSO3Li) purity >=99.9%, moisture≤0.1%, substance≤0.005% not soluble in water, total trace metal impurity content
≤1000ppm。
7. a kind of preparation method of bis- (fluorine sulphonyl) imine lithiums of high-purity according to claim 6, characterized in that described
Sulfonic Lithium (RSO3Li) moisture≤200ppm, total trace metal impurity content≤200ppm.
8. a kind of preparation method of bis- (fluorine sulphonyl) imine lithiums of high-purity according to claim 1, characterized in that step
(2) vacuum degree is 0.010~0.1MPa when concentration in, and temperature is 10~60 DEG C, is concentrated into the 1/6~1/2 of original solution volume.
9. a kind of preparation method of bis- (fluorine sulphonyl) imine lithiums of high-purity according to claim 8, characterized in that step
(2) vacuum degree is 0.050~0.080MPa when concentration in, temperature is 30~50 DEG C, is concentrated into the 1/5~1/3 of original solution volume.
10. a kind of preparation method of bis- (fluorine sulphonyl) imine lithiums of high-purity according to claim 1, characterized in that step
(3) ether organic solvent dosage described in is 2~5 times of concentrate, the low polar non-proton organic solvent be selected from n-hexane,
One or more combinations in hexamethylene, pentamethylene, dichloromethane or chloroform.
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| CN112174101A (en) * | 2020-09-23 | 2021-01-05 | 湖南博信新能源科技有限公司 | Preparation method of high-purity lithium bis (fluorosulfonyl) imide |
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| CN115959636A (en) * | 2022-12-21 | 2023-04-14 | 浙江研一新能源科技有限公司 | Preparation method of lithium bis (fluorosulfonyl) imide and lithium ion battery |
| EP4435917A1 (en) * | 2023-03-24 | 2024-09-25 | Samsung SDI Co., Ltd. | Electrolyte for rechargeable lithium battery and rechargeable lithium battery including the same |
| CN117069076A (en) * | 2023-07-25 | 2023-11-17 | 湖南福邦新材料有限公司 | Preparation method of lithium bis (fluorosulfonyl) imide |
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