WO2022262175A1 - 一种双氟磺酰亚胺锂及其制备方法和应用 - Google Patents
一种双氟磺酰亚胺锂及其制备方法和应用 Download PDFInfo
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- WO2022262175A1 WO2022262175A1 PCT/CN2021/129083 CN2021129083W WO2022262175A1 WO 2022262175 A1 WO2022262175 A1 WO 2022262175A1 CN 2021129083 W CN2021129083 W CN 2021129083W WO 2022262175 A1 WO2022262175 A1 WO 2022262175A1
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- WIPO (PCT)
- Prior art keywords
- lithium
- preparation
- imide
- reaction
- bisfluorosulfonyl imide
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 42
- VDVLPSWVDYJFRW-UHFFFAOYSA-N lithium;bis(fluorosulfonyl)azanide Chemical compound [Li+].FS(=O)(=O)[N-]S(F)(=O)=O VDVLPSWVDYJFRW-UHFFFAOYSA-N 0.000 title abstract 3
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 50
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims abstract description 48
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 40
- VKHQYTLHHOQKSC-UHFFFAOYSA-N sulfosulfamic acid Chemical compound OS(=O)(=O)NS(O)(=O)=O VKHQYTLHHOQKSC-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 18
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 17
- 229910052744 lithium Inorganic materials 0.000 claims description 64
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 62
- 238000006243 chemical reaction Methods 0.000 claims description 60
- 150000003949 imides Chemical class 0.000 claims description 50
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 claims description 32
- 238000005292 vacuum distillation Methods 0.000 claims description 21
- 230000035484 reaction time Effects 0.000 claims description 13
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 11
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 9
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 7
- 229910001416 lithium ion Inorganic materials 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 3
- 239000002994 raw material Substances 0.000 abstract description 14
- 238000007086 side reaction Methods 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 3
- 238000006138 lithiation reaction Methods 0.000 abstract description 2
- PVMUVDSEICYOMA-UHFFFAOYSA-N n-chlorosulfonylsulfamoyl chloride Chemical compound ClS(=O)(=O)NS(Cl)(=O)=O PVMUVDSEICYOMA-UHFFFAOYSA-N 0.000 abstract description 2
- 230000007613 environmental effect Effects 0.000 abstract 1
- 238000003682 fluorination reaction Methods 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
- 239000007789 gas Substances 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- -1 lithium hexafluorophosphate Chemical group 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 239000012065 filter cake Substances 0.000 description 9
- 239000012535 impurity Substances 0.000 description 9
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 8
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 8
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 231100000331 toxic Toxicity 0.000 description 4
- 230000002588 toxic effect Effects 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 229910052792 caesium Inorganic materials 0.000 description 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- KTQDYGVEEFGIIL-UHFFFAOYSA-N n-fluorosulfonylsulfamoyl fluoride Chemical compound FS(=O)(=O)NS(F)(=O)=O KTQDYGVEEFGIIL-UHFFFAOYSA-N 0.000 description 3
- 229910052701 rubidium Inorganic materials 0.000 description 3
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 3
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JUXXCHAGQCBNTI-UHFFFAOYSA-N 1-n,1-n,2-n,2-n-tetramethylpropane-1,2-diamine Chemical compound CN(C)C(C)CN(C)C JUXXCHAGQCBNTI-UHFFFAOYSA-N 0.000 description 2
- XOQAYIIHISMMHK-UHFFFAOYSA-N ClS(=O)(=O)S(=O)(=O)S(=O)(=O)Cl Chemical group ClS(=O)(=O)S(=O)(=O)S(=O)(=O)Cl XOQAYIIHISMMHK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- ZEIYBPGWHWECHV-UHFFFAOYSA-N nitrosyl fluoride Chemical compound FN=O ZEIYBPGWHWECHV-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000002912 waste gas Substances 0.000 description 2
- 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 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- GUNJVIDCYZYFGV-UHFFFAOYSA-K Antimony trifluoride Inorganic materials F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 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
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- CHHOPPGAFVFXFS-UHFFFAOYSA-M [Li+].[O-]S(F)(=O)=O Chemical compound [Li+].[O-]S(F)(=O)=O CHHOPPGAFVFXFS-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000004146 energy storage Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000001153 fluoro group Chemical class F* 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- NTZQXTIIJGXIMQ-UHFFFAOYSA-N fluorosulfonyl hypofluorite Chemical compound FOS(F)(=O)=O NTZQXTIIJGXIMQ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 1
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 1
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IQQPEXLMLGEVDX-UHFFFAOYSA-N n,n-diethylethanamine;sulfurofluoridic acid Chemical compound OS(F)(=O)=O.CCN(CC)CC IQQPEXLMLGEVDX-UHFFFAOYSA-N 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 239000002341 toxic gas Substances 0.000 description 1
- 238000005406 washing 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
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0566—Liquid materials
- H01M10/0568—Liquid materials characterised by the solutes
-
- C—CHEMISTRY; METALLURGY
- 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
Definitions
- the invention belongs to the technical field of chemical synthesis, and in particular relates to lithium bisfluorosulfonyl imide and its preparation method and application.
- lithium-ion batteries In recent years, driven by smart phones, mobile power supplies, tablet computers and other products, the output value of the domestic lithium battery industry has continued to grow; at the same time, the application of lithium-ion batteries is no longer limited to electronic consumer products, power and energy storage are two new industries. The application direction of lithium batteries has brought unlimited market space. At the same time, with the expansion of its application field, the demand for further improvement of battery characteristics is also increasing. At present, the most widely used electrolyte lithium salt is lithium hexafluorophosphate. Although it has good comprehensive performance, it is not enough to meet the growing demand of lithium-ion batteries due to its own shortcomings such as instability, easy water absorption, short life, and poor low-temperature performance. application requirements.
- lithium bisfluorosulfonyl imide (LiFSI) has better thermal stability, chemical stability, higher conductivity and lower corrosion rate, and is considered to be a new generation of lithium salt that may replace lithium hexafluorophosphate , can be widely used in lithium batteries and supercapacitors.
- CN101747242B discloses that sulfonamide reacts with thionyl chloride and chlorosulfonic acid to obtain dichlorosulfonimide, and then reacts with antimony trifluoride and potassium carbonate (cesium or rubidium) to obtain potassium difluorosulfonimide (cesium or rubidium), and finally potassium bisfluorosulfonyl imide (cesium or rubidium) and lithium perchlorate or lithium tetrafluoroborate undergo metathesis reaction to obtain lithium bisfluorosulfonyl imide, the process is complicated and the yield is low.
- CN107265419A discloses a production method of bis(fluorosulfonyl)imide lithium or bis(fluorosulfonyl)imide sodium, wherein, sulfamic acid is reacted with halosulfonic acid and triethylamine, Generate bis(sulfonyl)imide, then add potassium hydroxide to generate potassium bis(sulfonyl)imide triple salt, then add oxalyl chloride to generate potassium bis(chlorosulfonyl)imide, and finally add Hydrogen fluoride to obtain golden yellow bis(fluorosulfonyl)imide, the process is relatively complicated, and no yield and purity data are given.
- KR102223112B1 discloses the preparation method of fluorosulfonimide potassium salt, wherein, chlorosulfonic acid and ammonia are reacted to generate iminodisulfonic acid, which is fluorinated by nitrosyl fluoride to generate difluorosulfonimide, and then Lithium hydroxide is added to generate lithium bisfluorosulfonyl imide. Since nitrosyl fluoride is unstable, toluene solvent and the like are needed. Using lithium hydroxide in the lithiation process will generate water, resulting in low purity of the reaction product.
- US5916475A discloses the use of fluorosulfonic acid and urea to react to prepare bisfluorosulfonimide, and then lithiate to obtain lithium bisfluorosulfonimide. All operations need to be carried out in hydrofluoric acid-resistant devices, and the investment in equipment is large , high operational risk.
- WO2009123328A1 discloses the use of cyanogen chloride and sulfur trioxide to generate chlorosulfonic acid isocyanate, which is then reacted with chlorosulfonic acid to prepare dichlorosulfonimide.
- Cyanogen chloride is a highly toxic gas and has a great impact on the safety environment.
- US20120245386A1 discloses that SO 2 F 2 and NH 3 are used as raw materials, tetramethylpropylenediamine (TMPDA) is used as a base, and acetonitrile is used as a solvent to react at 10-15°C. After the reaction is completed, the low-boiling point liquid is separated under reduced pressure. , the viscous product was dissolved with methanol at 30°C, and then one equivalent of tetrabutylammonium bromide aqueous solution was added dropwise to the methanol solution, and then a white solid was precipitated, and the tetrabutylammonium with a yield of 84.4% was obtained after filtration Bisfluorosulfonyl imide metal salt. SO 2 F 2 is highly toxic, completely colorless and odourless, and significant precautions must be taken.
- TMPDA tetramethylpropylenediamine
- acetonitrile is used as a solvent to react at 10-15°
- WO2010140580A1 discloses that SO 2 F 2 , ammonia gas and 6 times the equivalent of fluorine salt are heated to 60°C for reaction to directly generate bisfluorosulfonyl imide metal salt. Also present SO2F2 is highly toxic, completely colorless and odorless, and significant precautions must be taken.
- WO2010113835A1 discloses that the mass ratio of SO 2 F 2 , NH 3 and Et 3 N is 2:1:3, acetonitrile is used as solvent, and triethylamine bisfluorosulfonimide metal is obtained with a yield of more than 90% under ice-water bath salt and a small amount of by-products, slowly add various metal hydroxides to the triethylamine bisfluorosulfonimide metal salt solution, remove triethylamine to obtain the product bisfluorosulfonimide metal salt.
- the technical problem to be solved by the present invention the preparation of lithium bisfluorosulfonyl imide in the prior art, the raw materials used are highly toxic and corrosive, the production cost is high, the yield and purity are low, and the impact on the environment is large.
- one of the purposes of the present invention is to provide a preparation method for lithium bisfluorosulfonyl imide, which has simple raw materials, low preparation cost, less waste gas generation, less impact on the environment and high reaction yield , the product has high purity and is easy to industrialize;
- the second object of the present invention is to provide a lithium bisfluorosulfonyl imide prepared by the above preparation method;
- the third object of the present invention is to provide the above preparation method to obtain bisfluorosulfonyl lithium Application of lithium imide or above-mentioned lithium bisfluorosulfonyl imide in lithium ion battery.
- the invention provides a kind of preparation method of bisfluorosulfonamide, comprising the following steps:
- reaction pressure is 0.8 to 1.5Mpa
- step (2) reacting thionyl chloride with iminodisulfonic acid gained in step (1), and obtaining dichlorosulfonyl imide through vacuum distillation;
- step (3) react the dichlorosulfonimide obtained in step (2) with hydrogen fluoride, and obtain the difluorosulfonimide through vacuum distillation;
- step (3) Reaction of bisfluorosulfonimide obtained in step (3) with lithium fluoride, solid-liquid separation, purification and drying to obtain lithium bisfluorosulfonimide.
- step (1) the molar ratio of ammonia to sulfur trioxide is 1:2-3.
- the reaction pressure is 0.8-1.0 MPa, preferably, the reaction temperature is 20-30° C., and more preferably, the reaction time is 4-6 hours.
- the reaction temperature is 80-100° C., and preferably, the reaction time is 12-16 hours.
- the molar ratio of iminodisulfonic acid to thionyl chloride is 1:2.0-2.5, preferably 1:2.2-2.5.
- step (3) the molar ratio of bischlorosulfonimide to hydrogen fluoride is 1:2.0-3.0.
- the reaction temperature is 80-150°C, preferably 90-120°C, and preferably, the reaction time is 14-20h.
- step (4) the molar ratio of bisfluorosulfonimide to lithium fluoride is 1:0.85-1.00.
- the reaction temperature is 120° C. to 160° C., and preferably, the reaction time is 30-60 minutes.
- the present invention also provides lithium bisfluorosulfonyl imide prepared by the above preparation method, and the purity of the lithium bisfluorosulfonyl imide is ⁇ 99.6%.
- the present invention also provides a lithium bisfluorosulfonyl imide prepared by the above preparation method or an application of the above lithium bisfluorosulfonyl imide in a lithium ion battery.
- the present invention also provides a kind of preparation method of dichlorosulfonimide, comprising the following steps:
- reaction pressure is 0.8 to 1.5Mpa
- step (2) reacting thionyl chloride with iminodisulfonic acid obtained in step (1), and distilling under reduced pressure to obtain dichlorosulfonimide.
- sulfur trioxide and ammonia are used as raw materials to prepare iminodisulfonic acid, which is chlorinated by thionyl chloride to obtain dichlorosulfonimide, and then fluorinated and lithiated in sequence to obtain difluorosulfonic acid.
- Lithium imide the raw materials used are simple, the preparation cost is low; the three wastes are produced less, the corrosion is small, the process is green and environmentally friendly; the side reaction is less, it has excellent yield, the product is high in purity, and can meet the requirements of large-scale industrial production on output and quality .
- the preparation method of lithium bisfluorosulfonyl imide provided by the present invention is a four-step reaction method, and its corresponding chemical reaction formula is as follows:
- the invention provides a preparation method of lithium bisfluorosulfonyl imide.
- the preparation method comprises the following steps:
- reaction pressure is 0.8 to 1.5Mpa
- step (2) reacting thionyl chloride with iminodisulfonic acid gained in step (1), and obtaining dichlorosulfonyl imide through vacuum distillation;
- step (3) react the dichlorosulfonimide obtained in step (2) with hydrogen fluoride, and obtain the difluorosulfonimide through vacuum distillation;
- step (3) Reaction of bisfluorosulfonimide obtained in step (3) with lithium fluoride, solid-liquid separation, purification and drying to obtain lithium bisfluorosulfonimide.
- step (1) the molar ratio of ammonia to sulfur trioxide is 1:2-3. Excessive sulfur trioxide is used to allow ammonia to react completely, to avoid excessive ammonia and further reaction with iminodisulfonic acid to generate unnecessary by-products.
- the reaction pressure is 0.8-1.5Mpa. When the pressure is lower than 0.8MPa, the ammonia gas cannot be liquefied, which makes the reaction difficult. When the pressure is greater than 1.5MPa, there is no significant difference in the reaction yield and reaction rate, and it brings greater safety.
- reaction pressure is 0.8-1.0MPa, more preferably, reaction temperature is 20 ⁇ 30 °C, when reaction temperature is lower than 20 °C, reaction rate slows down, and reaction yield reduces, then needs more when greater than 30 °C
- the high pressure liquefies the ammonia gas, and more preferably, the reaction time is 4-6 hours.
- Step (1) is carried out in a high-pressure reactor. During the specific operation, sulfur trioxide is first added to the reactor, then ammonia gas is passed into it, and nitrogen is used to pressurize. Remove unreacted sulfur trioxide at 80°C to obtain iminodisulfonic acid.
- the reaction temperature is 80-100° C., preferably, the reaction time is 12-16 hours.
- the molar ratio of iminodisulfonic acid to thionyl chloride is 1:2.0-2.5, preferably 1:2.2-2.5.
- 1 equivalent of iminodisulfonic acid reacts with 2 equivalents of thionyl chloride. Due to the high reaction temperature, part of thionyl chloride will be lost during the reflux process, so the minimum amount of thionyl chloride is generally is 2.2 equivalents, thionyl chloride higher than 2.5 equivalents has no significant impact on the reaction yield and reaction rate.
- the reaction product is subjected to vacuum distillation at 120-130° C. for 3-5 hours, and the vacuum degree of the vacuum distillation is -0.05 MPa to -0.09 MPa to obtain dichlorosulfonimide.
- step (3) the molar ratio of dichlorosulfonimide to hydrogen fluoride is 1:2.0-3.0.
- the reaction temperature is 80-150°C, preferably 90-120°C, and preferably, the reaction time is 14-20h. After the reaction, blow nitrogen into the system for 4 hours to remove the generated hydrogen chloride gas and unreacted hydrogen fluoride gas.
- Step (3) The vacuum distillation is carried out at 90-110 ° C, the vacuum degree of the vacuum distillation is -0.05MPa ⁇ -0.09MPa, the vacuum distillation time is 2 ⁇ 3h, and the fraction obtained by the vacuum distillation is difluorosulfonyl
- the imine, the distillation residue participates in the preparation reaction of the next bisfluorosulfonimide.
- step (4) the molar ratio of bisfluorosulfonimide to lithium fluoride is 1:0.85-1.00.
- the post-treatment of lithium fluoride is difficult and the remaining lithium fluoride is difficult to remove, it is preferable to completely react lithium fluoride.
- the reaction temperature is 120°C-160°C, preferably, the reaction time is 30-60 minutes; after the reaction, blow nitrogen gas into the system for 1 hour to remove the generated hydrogen fluoride gas, and then purify the obtained lithium bisfluorosulfonyl imide and drying to obtain lithium bisfluorosulfonimide; the purification operation includes washing the reaction product with dichloromethane to remove residual bisfluorosulfonimide, then dissolving it with ether, filtering to remove impurities, and then evaporating and concentrating, Add an organic solvent to recrystallize the concentrated solution, and finally dry to obtain lithium bisfluorosulfonyl imide.
- the lithium bisfluorosulfonyl imide prepared by the preparation method of the present invention has a purity of ⁇ 99.6%.
- the present invention also provides a lithium bisfluorosulfonyl imide prepared by the above preparation method or an application of the above lithium bisfluorosulfonyl imide in a lithium ion battery.
- the present invention also provides a kind of preparation method of dichlorosulfonimide, comprising the following steps:
- reaction pressure is 0.8 to 1.5Mpa
- step (2) reacting thionyl chloride with iminodisulfonic acid obtained in step (1), and distilling under reduced pressure to obtain dichlorosulfonimide.
- the raw materials or reagents used in the present invention are all purchased from mainstream manufacturers in the market, and those who do not indicate the manufacturer or the concentration are all analytically pure grade raw materials or reagents that can be routinely obtained. As long as they can play the expected role, There are no particular restrictions.
- the instruments and equipment used in this example are all purchased from major manufacturers in the market, and there are no special limitations as long as they can play the expected role. If no specific technique or condition is indicated in this example, the technique or condition described in the literature in this field or the product manual shall be followed.
- the high-pressure reactor adopts the 2L autoclave of Weihai Huanyu Chemical Machinery Co., Ltd.;
- the NMR analyzer adopts AVANCE-400 from Bruker Company of Germany.
- step (2) Add 165.3g of the iminodisulfonic acid obtained in step (1) into the reactor, heat it to 80°C, and slowly add 245.1g of thionyl chloride (molecular weight 118.97g/mol) dropwise thereinto, the reaction produces The tail gas was absorbed with potassium hydroxide alkali solution, stirred and reacted for 12 hours, then cooled to room temperature, and vacuum distillation was carried out at -0.05MPa, 120°C for 5 hours to obtain 180.5g of the product, which was identified by 1 H-NMR spectrum For two chlorosulfonimide (molecular weight 214.03g/mol).
- step (3) Add 180.5 g of bischlorosulfonimide obtained in step (2) into the reactor, heat it to 80° C., slowly feed 33.8 g of HF (molecular weight 20.01 g/mol) gas, and drop to At room temperature, nitrogen gas was blown into the reactor for 4 hours, and then vacuum distillation was carried out at -0.05 MPa at 90°C for 3 hours to obtain 126.8 g of bisfluorosulfonimide (molecular weight: 181.13 g/mol).
- HF molethoxysulfonimide
- step (2) Add the iminodisulfonic acid obtained in step (1) of 168.3 into the reactor, heat it to 100°C, slowly add 282g of thionyl chloride dropwise, and absorb the tail gas generated in the reaction with potassium hydroxide lye , stirred and reacted for 16 hours, then lowered to room temperature, and distilled under reduced pressure at -0.09MPa, 130°C for 3h to obtain 189.8g of the product, which was identified as dichlorosulfonimide by 1 H-NMR spectrum.
- step (3) Add 189.8g of bischlorosulfonimide obtained in step (2) into the reactor, heat it to 90°C, slowly feed 53g of HF gas, react for 20 hours and then cool down to room temperature, and blow nitrogen into the reactor After 4 hours, vacuum distillation was carried out at -0.09MPa and 110°C for 2 hours to obtain 141.8g of bisfluorosulfonimide.
- step (2) Add 166.7g of the iminodisulfonic acid obtained in step (1) into the reactor, heat it to 90°C, slowly add 268.9g of thionyl chloride dropwise therein, and use the tail gas produced in the reaction with potassium hydroxide base The solution was absorbed, stirred and reacted for 14 hours and then lowered to room temperature, vacuum distillation was carried out at -0.05MPa and 125°C for 4 hours to obtain 186.2g of the product, which was identified as dichlorosulfonyl sulfonyl chloride by 1 H-NMR spectrum amine.
- step (3) Add 186.2g of the bischlorosulfonimide obtained in step (2) into the reactor, heat it to 100°C, slowly pass in 43.52g of HF gas, react for 16 hours and then cool down to room temperature, and blow into the reactor Nitrogen for 4 hours, then vacuum distillation at -0.05 MPa, 100°C for 3 hours to obtain 134.4 g of bisfluorosulfonimide.
- step (2) Add 164.9g of iminodisulfonic acid obtained in step (1) into the reactor, heat it to 90°C, and slowly add 222.63g of thionyl chloride dropwise therein, and the tail gas generated in the reaction is treated with potassium hydroxide base The solution was absorbed, stirred and reacted for 13 hours and then lowered to room temperature, vacuum distillation was carried out at -0.05MPa and 125°C for 4 hours to obtain 181.73g of the product, which was identified as dichlorosulfonyl sulfonyl chloride by 1 H-NMR spectrum amine.
- step (3) Add 181.73g of the bischlorosulfonimide obtained in step (2) into the reactor, heat it to 150°C, slowly pass in 47.57g of HF gas, react for 18 hours and then cool down to room temperature, and blow into the reactor Nitrogen for 4 hours, and then vacuum distillation was carried out at -0.05MPa and 100°C for 3 hours to obtain 127.96g of bisfluorosulfonimide.
- step (2) Add 175.1g of the bischlorosulfonimide obtained in step (2) into the reactor, heat it to 80°C, slowly pass in 32.78g of HF gas, react for 14 hours and then cool down to room temperature, and blow into the reactor Nitrogen was used for 4 hours, and then vacuum distillation was carried out at -0.05 MPa at 90°C for 3 hours to obtain 120.20 g of bisfluorosulfonimide.
- step (3) Add 5.0g of lithium fluoride to the reactor, heat it to 120°C, slowly add 34.91g of bisfluorosulfonimide obtained in step (2) dropwise, react for 30 minutes, blow nitrogen into the reactor for 1 hour, cooled to room temperature, then washed the reaction product with dichloromethane, filtered the filter cake and dissolved it with ether, filtered to remove impurities to obtain the filtrate, concentrated to 30% by weight with a rotary evaporator, and then used dimethyl carbonate to concentrate The solution was recrystallized, and finally vacuum-dried to obtain 31.92 g of lithium bisfluorosulfonyl imide. The purity of lithium bisfluorosulfonimide was determined by a Metrohm 833 ion chromatograph.
- Steps (1) and (2) are the same as comparative example 1;
- Comparative Example 1 adopts sulfamic acid, chlorosulfonic acid and thionyl chloride to prepare two chlorosulfonimides, and the yield of two chlorosulfonimides is 81.8%, which is lower than that of Example 1.
- the total yield of chlorosulfonimide is 84.48%, thus the total yield of lithium bisfluorosulfonimide is also lower than that in Example 1.
- Comparative example 2 adopts sulfamic acid, chlorosulfonic acid and thionyl chloride to prepare dichlorosulfonimide, and the synthesis of bisfluorosulfonimide lithium adopts the technology of low reaction temperature and long reaction time, and yield and purity are higher Low.
- the present invention uses sulfur trioxide and ammonia as raw materials to prepare iminodisulfonic acid, which is chlorinated by thionyl chloride to obtain dichlorosulfonimide, and then fluorinated and lithiated to produce Lithium bisfluorosulfonyl imide is obtained, the raw materials used are simple, the production cost is low; the three wastes are produced less, the process is green and environmentally friendly; the side reaction is less, the product has excellent yield, and the product has high purity, which can meet the requirements of large-scale industrial production on output and quality .
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Abstract
Description
Claims (15)
- 一种双氟磺酰亚胺锂的制备方法,其特征在于,包括以下步骤:(1)将三氧化硫和氨气在高压反应釜中进行反应,得到亚氨基二磺酸,其中反应压力为0.8~1.5Mpa;(2)将二氯亚砜和步骤(1)所得亚氨基二磺酸反应,经减压蒸馏得到双氯磺酰亚胺;(3)将步骤(2)所得双氯磺酰亚胺和氟化氢反应,经减压蒸馏得到双氟磺酰亚胺;(4)将步骤(3)所得双氟磺酰亚胺和氟化锂反应,经固液分离,纯化和干燥得到双氟磺酰亚胺锂。
- 根据权利要求1所述双氟磺酰亚胺锂的制备方法,其特征在于,在步骤(1)中,所述氨气与三氧化硫的摩尔比为1:2~3。
- 根据权利要求1或2所述双氟磺酰亚胺锂的制备方法,其特征在于,在步骤(1)中,所述反应压力为0.8-1.0MPa。
- 根据权利要求1~3中任一项所述双氟磺酰亚胺锂的制备方法,其特征在于,在步骤(1)中,所述反应温度为20~30℃。
- 根据权利要求1~4中任一项所述双氟磺酰亚胺锂的制备方法,其特征在于,在步骤(1)中,所述反应时间为4~6h。
- 根据权利要求1~5中任一项所述双氟磺酰亚胺锂的制备方法,其特征在于,在步骤(2)中,反应温度为80~100℃。
- 根据权利要求1~6中任一项所述双氟磺酰亚胺锂的制备方法,其特征在于,在步骤(2)中,反应时间为12~16小时。
- 根据权利要求1~7中任一项所述双氟磺酰亚胺锂的制备方法,其特征在于,在步骤(2)中,所述亚氨基二磺酸和二氯亚砜的摩尔比为1:2.0~2.5,优选为1:2.2~2.5。
- 根据权利要求1~8中任一项所述双氟磺酰亚胺锂的制备方法,其特征在于,在步骤(3)中,双氯磺酰亚胺与氟化氢的摩尔比为1:2.0~3.0。
- 根据权利要求1~9中任一项所述双氟磺酰亚胺锂的制备方法,其特征在于,在步骤(3)中,反应温度为80~150℃,优选为90~120℃,优选 地,反应时间为14~20h。
- 根据权利要求1~10中任一项所述双氟磺酰亚胺锂的制备方法,其特征在于,在步骤(4)中,双氟磺酰亚胺与氟化锂的摩尔比为1:0.85~1.00。
- 根据权利要求1~11中任一项所述双氟磺酰亚胺锂的制备方法,其特征在于,在步骤(4)中,反应温度为120℃~160℃,优选地,反应时间为30-60分钟。
- 一种双氟磺酰亚胺锂,其由权利要求1~12中任一项所述制备方法制得,其特征在于,该双氟磺酰亚胺锂的纯度≥99.6%。
- 权利要求1-12中任一项所述制备方法制得双氟磺酰亚胺锂或权利要求13所述双氟磺酰亚胺锂在锂离子电池中的应用。
- 一种双氯磺酰亚胺的制备方法,其特征在于,包括以下步骤:(1)将三氧化硫和氨气在高压反应釜中进行反应,得到亚氨基二磺酸,其中反应压力为0.8~1.5Mpa;(2)将二氯亚砜和步骤(1)所得亚氨基二磺酸反应,经减压蒸馏得到双氯磺酰亚胺。
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