CN117567377A - Preparation method and application of imidazole thiocarboxylate compound - Google Patents
Preparation method and application of imidazole thiocarboxylate compound Download PDFInfo
- Publication number
- CN117567377A CN117567377A CN202311537807.4A CN202311537807A CN117567377A CN 117567377 A CN117567377 A CN 117567377A CN 202311537807 A CN202311537807 A CN 202311537807A CN 117567377 A CN117567377 A CN 117567377A
- Authority
- CN
- China
- Prior art keywords
- imidazole
- thiocarboxylate
- compound
- preparation
- electrolyte
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 imidazole thiocarboxylate compound Chemical class 0.000 title claims abstract description 46
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- 239000011255 nonaqueous electrolyte Substances 0.000 claims abstract description 22
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 13
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 11
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 claims abstract description 8
- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000003792 electrolyte Substances 0.000 claims description 16
- 239000000654 additive Substances 0.000 claims description 12
- 230000000996 additive effect Effects 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000007773 negative electrode material Substances 0.000 claims description 9
- 239000007774 positive electrode material Substances 0.000 claims description 9
- 229910052744 lithium Inorganic materials 0.000 claims description 8
- 239000008151 electrolyte solution Substances 0.000 claims description 7
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 claims description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 6
- 229940125904 compound 1 Drugs 0.000 claims description 6
- 229940125782 compound 2 Drugs 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- BJWMSGRKJIOCNR-UHFFFAOYSA-N 4-ethenyl-1,3-dioxolan-2-one Chemical compound C=CC1COC(=O)O1 BJWMSGRKJIOCNR-UHFFFAOYSA-N 0.000 claims description 4
- 229910003002 lithium salt Inorganic materials 0.000 claims description 4
- 159000000002 lithium salts Chemical group 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 claims description 3
- 229910000733 Li alloy Inorganic materials 0.000 claims description 3
- 229910000528 Na alloy Inorganic materials 0.000 claims description 3
- 239000001989 lithium alloy Substances 0.000 claims description 3
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 claims description 3
- 239000003125 aqueous solvent Substances 0.000 claims description 2
- HPTMZNZYFRTOKS-UHFFFAOYSA-N ethenesulfinic acid Chemical compound OS(=O)C=C HPTMZNZYFRTOKS-UHFFFAOYSA-N 0.000 claims description 2
- NLVXSWCKKBEXTG-UHFFFAOYSA-M ethenesulfonate Chemical compound [O-]S(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-M 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 3
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000002000 Electrolyte additive Substances 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 9
- SBLRHMKNNHXPHG-UHFFFAOYSA-N 4-fluoro-1,3-dioxolan-2-one Chemical compound FC1COC(=O)O1 SBLRHMKNNHXPHG-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 238000000034 method Methods 0.000 description 6
- 210000001787 dendrite Anatomy 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- GELKBWJHTRAYNV-UHFFFAOYSA-K lithium iron phosphate Chemical compound [Li+].[Fe+2].[O-]P([O-])([O-])=O GELKBWJHTRAYNV-UHFFFAOYSA-K 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 description 4
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 4
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 4
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 4
- 229910000625 lithium cobalt oxide Inorganic materials 0.000 description 4
- BFZPBUKRYWOWDV-UHFFFAOYSA-N lithium;oxido(oxo)cobalt Chemical compound [Li+].[O-][Co]=O BFZPBUKRYWOWDV-UHFFFAOYSA-N 0.000 description 4
- 229940017219 methyl propionate Drugs 0.000 description 4
- 238000011056 performance test Methods 0.000 description 4
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- ACKHWUITNXEGEP-UHFFFAOYSA-N aluminum cobalt(2+) nickel(2+) oxygen(2-) Chemical compound [O-2].[Al+3].[Co+2].[Ni+2] ACKHWUITNXEGEP-UHFFFAOYSA-N 0.000 description 3
- 239000012752 auxiliary agent Substances 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- CXULZQWIHKYPTP-UHFFFAOYSA-N cobalt(2+) manganese(2+) nickel(2+) oxygen(2-) Chemical compound [O--].[O--].[O--].[Mn++].[Co++].[Ni++] CXULZQWIHKYPTP-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910013716 LiNi Inorganic materials 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- ZIALXKMBHWELGF-UHFFFAOYSA-N [Na].[Cu] Chemical compound [Na].[Cu] ZIALXKMBHWELGF-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 2
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229940090181 propyl acetate Drugs 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- GEWWCWZGHNIUBW-UHFFFAOYSA-N 1-(4-nitrophenyl)propan-2-one Chemical compound CC(=O)CC1=CC=C([N+]([O-])=O)C=C1 GEWWCWZGHNIUBW-UHFFFAOYSA-N 0.000 description 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 229910015013 LiAsF Inorganic materials 0.000 description 1
- 229910013075 LiBF Inorganic materials 0.000 description 1
- 229910013188 LiBOB Inorganic materials 0.000 description 1
- 229910013872 LiPF Inorganic materials 0.000 description 1
- 229910013870 LiPF 6 Inorganic materials 0.000 description 1
- 229910012097 LiSbF Inorganic materials 0.000 description 1
- 101150058243 Lipf gene Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910020808 NaBF Inorganic materials 0.000 description 1
- 229910020892 NaBOB Inorganic materials 0.000 description 1
- 229910021201 NaFSI Inorganic materials 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- ZJPPTKRSFKBZMD-UHFFFAOYSA-N [Li].FS(=N)F Chemical compound [Li].FS(=N)F ZJPPTKRSFKBZMD-UHFFFAOYSA-N 0.000 description 1
- IDSMHEZTLOUMLM-UHFFFAOYSA-N [Li].[O].[Co] Chemical class [Li].[O].[Co] IDSMHEZTLOUMLM-UHFFFAOYSA-N 0.000 description 1
- UQFSQHKNYIXJJE-UHFFFAOYSA-N [Na].FC(F)(F)c1nc(C#N)c([nH]1)C#N Chemical compound [Na].FC(F)(F)c1nc(C#N)c([nH]1)C#N UQFSQHKNYIXJJE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 239000006256 anode slurry Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- DFFDSQBEGQFJJU-UHFFFAOYSA-N butyl hydrogen carbonate Chemical compound CCCCOC(O)=O DFFDSQBEGQFJJU-UHFFFAOYSA-N 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- CKFRRHLHAJZIIN-UHFFFAOYSA-N cobalt lithium Chemical compound [Li].[Co] CKFRRHLHAJZIIN-UHFFFAOYSA-N 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000006258 conductive agent Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000009831 deintercalation Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- CYEDOLFRAIXARV-UHFFFAOYSA-N ethyl propyl carbonate Chemical compound CCCOC(=O)OCC CYEDOLFRAIXARV-UHFFFAOYSA-N 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- DEUISMFZZMAAOJ-UHFFFAOYSA-N lithium dihydrogen borate oxalic acid Chemical compound B([O-])(O)O.C(C(=O)O)(=O)O.C(C(=O)O)(=O)O.[Li+] DEUISMFZZMAAOJ-UHFFFAOYSA-N 0.000 description 1
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 description 1
- XKLXIRVJABJBLQ-UHFFFAOYSA-N lithium;2-(trifluoromethyl)-1h-imidazole-4,5-dicarbonitrile Chemical compound [Li].FC(F)(F)C1=NC(C#N)=C(C#N)N1 XKLXIRVJABJBLQ-UHFFFAOYSA-N 0.000 description 1
- IGILRSKEFZLPKG-UHFFFAOYSA-M lithium;difluorophosphinate Chemical compound [Li+].[O-]P(F)(F)=O IGILRSKEFZLPKG-UHFFFAOYSA-M 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- KKQAVHGECIBFRQ-UHFFFAOYSA-N methyl propyl carbonate Chemical compound CCCOC(=O)OC KKQAVHGECIBFRQ-UHFFFAOYSA-N 0.000 description 1
- 239000011268 mixed slurry Substances 0.000 description 1
- CSXCEQPWXHUSIX-UHFFFAOYSA-N pentan-2-yl hydrogen carbonate Chemical compound CCCC(C)OC(O)=O CSXCEQPWXHUSIX-UHFFFAOYSA-N 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- VCCATSJUUVERFU-UHFFFAOYSA-N sodium bis(fluorosulfonyl)azanide Chemical compound FS(=O)(=O)N([Na])S(F)(=O)=O VCCATSJUUVERFU-UHFFFAOYSA-N 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 description 1
- 229910001488 sodium perchlorate Inorganic materials 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- KBVUALKOHTZCGR-UHFFFAOYSA-M sodium;difluorophosphinate Chemical compound [Na+].[O-]P(F)(F)=O KBVUALKOHTZCGR-UHFFFAOYSA-M 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 238000009461 vacuum packaging Methods 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon 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
-
- 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
- H01M10/054—Accumulators with insertion or intercalation of metals other than lithium, e.g. with magnesium or aluminium
-
- 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
- H01M10/0567—Liquid materials characterised by the additives
-
- 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
- H01M10/42—Methods or arrangements for servicing or maintenance of secondary cells or secondary half-cells
- H01M10/4235—Safety or regulating additives or arrangements in electrodes, separators or electrolyte
-
- 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)
- Manufacturing & Machinery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Secondary Cells (AREA)
Abstract
The invention provides a preparation method and application of an imidazole thiocarboxylate compound. Comprises the steps of reacting N, N' -thiocarbonyldiimidazole with unsaturated alcohol to generate imidazole thiocarboxylate compounds. The preparation method can effectively synthesize the imidazole thiocarboxylate compound, and the imidazole thiocarboxylate compound can be used as an electrolyte additive to be applied to non-aqueous electrolyte of an alkali metal battery, so that the electrochemical performance of the battery can be effectively improved.
Description
Technical Field
The invention relates to the technical field of material synthesis, in particular to a preparation method and application of an imidazole thiocarboxylate compound.
Background
The alkali metal battery is easy to generate dendrites in the circulation process, such as lithium dendrites, and the lithium dendrites are easy to pierce through a separation film of the battery, so that the battery is easy to generate short circuit, the dendrites are large in surface area and high in activity, and are easy to react with electrolyte, so that an SEI film (interface film) on the metal surface is continuously recombined, the electrolyte and active metal are consumed, the circulation efficiency is reduced, and the circulation life of the battery is shortened. Research shows that the imidazole compound is applied to battery electrolyte as an additive, can improve the existence condition of a battery cathode interface and cathode substances, and improves the high-low temperature cycle and the safety performance of the battery. Therefore, how to effectively improve the surface properties of the metal electrode and inhibit the generation of metal dendrites is an important point to be solved for further development of alkali metal batteries.
Disclosure of Invention
The invention aims to provide a preparation method of an imidazole thiocarboxylate compound, which can effectively synthesize the imidazole thiocarboxylate compound, and can effectively improve the performance of a battery when the imidazole thiocarboxylate compound is used as an electrolyte additive to be applied to a non-aqueous electrolyte of an alkali metal battery.
In order to achieve the above purpose, the present invention provides a method for preparing an imidazole thiocarboxylate compound, which comprises the step of reacting N, N' -thiocarbonyldiimidazole with unsaturated alcohol to generate the imidazole thiocarboxylate compound.
Compared with the prior art, the imidazole thiocarboxylate additive can be prepared by taking N, N' -thiocarbonyldiimidazole and unsaturated alcohol as raw materials for reaction, and the preparation method is simple and controllable, and is beneficial to popularization and application in electrolyte and secondary batteries.
As a preferred technical scheme, the N, N' -thiocarbonyldiimidazole and the unsaturated alcohol are mixed at the temperature of 0 ℃ before being heated to room temperature for reaction, and finally the imidazole thiocarboxylate compound is obtained through post-treatment.
As a preferred technical scheme, the post-treatment comprises concentration, extraction washing, drying and concentration in sequence. As an example, the concentration is reduced pressure concentration by a rotary evaporator, the extraction washing is repeated extraction washing by methylene dichloride and saturated sodium chloride solution, and the drying is drying by anhydrous magnesium sulfate.
As a preferred technical scheme, the unsaturated alcohol is any one of allyl alcohol and propargyl alcohol.
As a preferred technical scheme, the imidazole thiocarboxylate compound is at least one of a compound 1 and a compound 2:
the invention also provides an application of the imidazole thiocarboxylate compound prepared by the preparation method of the imidazole thiocarboxylate compound in the non-aqueous electrolyte, and the application of the imidazole thiocarboxylate compound in the non-aqueous electrolyte can effectively improve the electrochemical performance of an alkali metal battery.
The invention provides a non-aqueous electrolyte, which comprises electrolyte salt, a non-aqueous solvent and an additive, wherein the additive comprises the imidazole thiocarboxylate compound prepared by the preparation method.
As a preferred technical scheme, the mass percentage of the imidazole thiocarboxylate compound in the nonaqueous electrolyte is 0.01% -2.00%.
As a preferred technical scheme, the nonaqueous electrolyte further comprises a film forming auxiliary agent, wherein the film forming auxiliary agent comprises at least one of Vinylene Carbonate (VC), vinyl Ethylene Carbonate (VEC), ethylene Sulfonate (ES), 1, 3-propane sultone (1, 3-PS) and ethylene sulfonate (DTD), and the mass percentage of the film forming auxiliary agent in the nonaqueous electrolyte is 0.1% -5.0%.
As a preferred technical scheme, the electrolyte salt is lithium salt or sodium salt, and the mass percentage of the electrolyte salt in the nonaqueous electrolyte solution is 8% -14%.
As a preferred technical solution, the nonaqueous solvent is one or more of γ -butyrolactone (GBL), γ -valerolactone (GVL), γ -caprolactone (EMA), o-valerolactone (EMA), ethylene Carbonate (EC), propylene Carbonate (PC), fluoroethylene carbonate (FEC), butylene Carbonate (BC), dimethyl carbonate (DMC), diethyl carbonate (DEC), dipropyl carbonate (DPC), methyl ethyl carbonate (EMC), methyl propyl carbonate (PMC), ethyl propyl carbonate (PEC), methyl acetate (EMA), ethyl Acetate (EAC), propyl acetate (NPAC), methyl Propionate (MP), ethyl propionate (EEP) and Propyl Propionate (PP).
The fourth aspect of the invention provides an alkali metal battery comprising a positive electrode material and a negative electrode material, and further comprising the above-described nonaqueous electrolyte.
As a preferred technical scheme, the positive electrode material comprises a lithium cobalt oxide material, a lithium iron phosphate material, nickel cobalt manganese oxide or nickel cobalt aluminum oxide.
As a preferred embodiment, the negative electrode material includes lithium metal, lithium alloy, sodium metal, sodium alloy, other alkali metals or alloys.
Detailed Description
The invention provides a preparation method and application of an imidazole thiocarboxylate compound, in particular to the application of the imidazole thiocarboxylate compound prepared by the invention in non-aqueous electrolyte of an alkali metal battery, which can effectively improve the electrochemical performance of the alkali metal battery. The alkali metal cell of the present invention includes a positive electrode material and a negative electrode material in addition to the nonaqueous electrolytic solution.
The negative electrode material is lithium metal or lithium alloy, and the positive electrode material comprises lithium cobalt oxideA material, a lithium iron phosphate material, nickel cobalt manganese oxide or nickel cobalt aluminum oxide. The lithium cobalt oxide material is lithium cobalt oxide or doped and coated modified lithium cobalt oxide, the lithium iron phosphate material is lithium iron phosphate or doped and coated modified lithium iron phosphate, and the chemical formula of the nickel cobalt manganese oxide is LiNi x Co y M (1-x-y-z) O 2 The chemical formula of the nickel cobalt aluminum oxide is LiNi x Co y Al z N (1-x-y-z) O 2 Wherein M is at least one of Mg, cu, zn, A, sn, B, ga, cr, sr, V and Ti, N is at least one of Mn, mg, cu, zn, sn, B, ga, cr, sr, V and Ti, 0 < x.ltoreq.1, 0<y<1，0<z<1, x+y+z is less than or equal to 1. When the negative electrode material is sodium metal, sodium alloy, other alkali metals or alloys, the positive electrode material is a composite metal oxide similar to the positive electrode of a lithium metal battery. Of course, the positive electrode material may be other materials capable of generating ion deintercalation with sodium ions. As an example, the positive electrode material of the present invention is sodium cobaltate, and the negative electrode material is sodium metal; as another example, the positive electrode material of the present invention is lithium cobalt oxide, and the negative electrode material is lithium metal.
The nonaqueous electrolytic solution of the present invention may include an electrolyte salt, a nonaqueous solvent, a film-forming aid and an additive.
Wherein the mass percentage of the electrolyte salt in the nonaqueous electrolyte is 8% -14%, and the electrolyte salt is specifically but not limited to 8%, 8.5%, 9%, 10%, 10.5%, 11%, 11.5%, 12%, 12.5%, 13% and 14%. The electrolyte salt is an alkali metal salt, and may be a lithium salt or a sodium salt.
In particular, the lithium salt may be, but is not limited to, in particular lithium hexafluorophosphate (LiPF 6 ) Lithium tetrafluoroborate (LiBF) 4 ) Lithium 4, 5-dicyano-2-trifluoromethylimidazole (LiTDI), lithium perchlorate (LiClO) 4 ) Lithium hexafluoroarsenate (LiAsF) 6 ) Lithium hexafluoroantimonate (LiSbF) 6 ) Lithium dioxalate borate (LiBOB), lithium difluorosulfimide (LiFSI), lithium difluorophosphate (LiPF) 2 O 2 ) And lithium difluorooxalato borate (LiDFOB).
In particular, the sodium salt may be, but is not limited to, sodium hexafluorophosphate (NaPF 6 ) Boron tetrafluorideSodium acid (NaBF) 4 ) Sodium 4, 5-dicyano-2-trifluoromethylimidazole (NaTDI), sodium perchlorate (NaClO) 4 ) Sodium hexafluoroarsenate (NaAsF) 6 ) Sodium hexafluoroantimonate (NaSbF) 6 ) Sodium borate di (NaBOB), sodium bisfluorosulfonimide (NaFSI), sodium difluorophosphate (NaPF) 2 O 2 ) And sodium difluoro oxalato borate (NaDFOB).
The nonaqueous solvent is one or more of gamma-butyrolactone (GBL), gamma-valerolactone (GVL), gamma-caprolactone (EMA), o-valerolactone (EMA), ethylene Carbonate (EC), propylene Carbonate (PC), fluoroethylene carbonate (FEC), butylene Carbonate (BC), dimethyl carbonate (DMC), diethyl carbonate (DEC), dipropyl carbonate (DPC), ethylmethyl carbonate (EMC), propylmethyl carbonate (PMC), propylethyl carbonate (PEC), methyl acetate (EMA), ethyl Acetate (EAC), propylacetate (NPAC), methyl Propionate (MP), ethyl propionate (EEP), and propylpropionate (PP). As an example, the nonaqueous solvent may be a combination of dimethyl carbonate (DMC), ethylmethyl carbonate (EMC) and diethyl carbonate (DEC); as another example, the nonaqueous solvent may be a combination of Ethyl Methyl Carbonate (EMC) and fluoroethylene carbonate (FEC).
The film forming aid includes at least one of Vinylene Carbonate (VC), vinyl carbonate (VEC), vinyl sulfinate (ES), 1, 3-propane sultone (1, 3-PS), and vinyl sulfonate (DTD). The mass percentage of the film forming additive in the nonaqueous electrolyte is 0.1-5%, specifically but not limited to 0.1%, 0.5%, 1.0%, 1.5%, 2.0%, 2.5%, 3.0%, 3.5%, 4.0%, 4.5% and 5.0%.
The additive comprises imidazole thioformate compounds shown as a compound 1 and a compound 2:
the mass percentage of the imidazole thiocarboxylate compound in the nonaqueous electrolyte is 0.01% -2.00%, and the mass percentage is specifically but not limited to 0.01%, 0.05%, 0.10%, 0.20%, 0.30%, 0.40%, 0.50%, 0.60%, 0.70%, 0.80%, 0.90%, 1.00%, 1.20%, 1.40%, 1.60%, 1.80% and 2.00%.
Specifically, compound 1 is prepared with reference to equation one
14.5mmol of N, N' -thiocarbonyldiimidazole was added to 30ml of tetrahydrofuran, and 4.83mmol of allyl alcohol was added thereto at 0℃to prepare a mixture, followed by stirring and mixing, and the mixture was heated to room temperature for 2 hours. After the reaction, the reaction solution was concentrated under reduced pressure, the concentrate was dissolved in 100ml of methylene chloride, and then 100ml of saturated sodium chloride solution was used, followed by repeated extraction and washing for 3 times, and then dried over anhydrous magnesium sulfate, and the dried reaction solution was filtered and concentrated under reduced pressure to give compound 1 having a nuclear magnetic hydrogen spectrum of 1H NMR (60 MHz, CDCl 3) delta 8.34 (s, 1H), 7.63 (s, 1H), 7.02 (s, 1H), 5.86-6.18 (m, 1H), 5.36-5.52 (m, 2H), 4.98-5.21 (m, 2H).
Reactive one
Specifically, compound 2 is prepared with reference to equation two
14.5mmol of N, N-thiocarbonyldiimidazole was added to 30ml of tetrahydrofuran, and 4.83mmol of propargyl alcohol was added thereto at 0℃to prepare a mixture, followed by stirring and mixing, and the mixture was heated to room temperature for 2 hours. After the reaction, the reaction solution was concentrated under reduced pressure, the concentrate was dissolved in 100ml of methylene chloride, and then 100ml of saturated sodium chloride solution was used, followed by repeated extraction and washing for 3 times, and then dried over anhydrous magnesium sulfate, and the dried reaction solution was filtered and concentrated under reduced pressure to obtain compound 2. The nuclear magnetic resonance hydrogen spectrum was 1H NMR (60 MHz, CDCl 3) delta 8.34 (s, 1H), 7.63 (s, 1H), 7.02 (s, 1H), 4.27 (m, 2H), 3.37 (m, 1H).
Reactive type II
For a better description of the objects, technical solutions and advantageous effects of the present invention, the present invention will be further described with reference to specific examples. It should be noted that the following implementation of the method is a further explanation of the present invention and should not be taken as limiting the present invention.
Wherein, the specific conditions are not noted in the examples, and the method can be carried out according to the conventional conditions or the conditions suggested by manufacturers. The reagents or apparatus used were conventional products available commercially without the manufacturer's attention.
Example 1
(1) Preparation of nonaqueous electrolyte
Moisture content under argon atmosphere<In a vacuum glove box of 1ppm, methyl ethyl carbonate (EMC) and fluoroethylene carbonate (FEC) are mixed according to the weight ratio of EMC: fec=2:3 followed by 0.5g of compound 1, dissolved and stirred well followed by 12.5g of napf 6 And mixing uniformly to obtain the non-aqueous electrolyte.
(2) Preparation of the Positive electrode
Sodium cobaltate NaCoO 2 The adhesive PVDF and the conductive agent SuperP are mixed according to the mass ratio of 95:1:4, uniformly mixing to prepare sodium metal battery anode slurry with certain viscosity, coating the mixed slurry on two sides of an aluminum foil, and drying and rolling to obtain the anode plate.
(3) Preparation of separator
Polyethylene (PE) having a thickness of about 15 μm was used as the separator.
(4) Preparation of negative electrode
And compounding metal sodium onto a current collector copper foil with the thickness of about 10 mu m by a physical rolling method, regulating the pressure of a roller to cover sodium on two sides of the copper current collector, and controlling the thickness of the covered sodium to be about 35 mu m to obtain the sodium-copper composite belt cathode. Then after cutting pieces and slitting, the materials are placed in a glove box with dry argon atmosphere for storage.
(5) Preparation of sodium metal battery
And stacking the positive plate, the isolating film and the sodium-copper composite belt negative plate in sequence, and then stacking according to the requirement. And (3) after welding the tab, placing the tab in an aluminum plastic film of an external package of the battery, injecting the prepared electrolyte into the dried bare cell, sequentially carrying out the working procedures of vacuum packaging, standing, formation (0.05C constant current is charged to 3.6V, then 0.1C constant current is charged to 3.9V), shaping, capacity testing and the like, and finally obtaining the soft package sodium metal battery with 1 Ah.
(6) Cycle performance test
The sodium metal battery was charged and discharged at 25℃once at 0.5C/0.5C (the discharge capacity of the battery was C) 0 ) The upper limit voltage was 4.55V, and then 0.5C/0.5C charge and discharge was performed for 300 weeks under normal temperature conditions (the battery discharge capacity was C) 1 ) Capacity retention= (C 1 /C 0 )×100％。
The electrolyte formulations and cycle performance test results of examples 1 to 16 and comparative examples 1 to 2 are shown in table 1, wherein the preparation of the nonaqueous electrolyte, the preparation of the positive electrode, the preparation of the separator, the preparation of the negative electrode, the preparation method of the sodium metal battery and the cycle performance test conditions in examples 2 to 16 and comparative examples 1 to 2 are the same as those in example 1.
TABLE 1
As can be seen from the results of the cycle performance test in Table 1, the cycle performance of examples 1 to 16 is better than that of comparative examples 1 to 2, because the non-aqueous electrolyte additives of examples 1 to 16 include the imidazole thiocarboxylate additive, the conditions of the cathode interface and the cathode material of the battery are improved, and the cycle performance of the battery is improved, which indicates that the non-aqueous electrolyte additive has a better application prospect in the alkali metal ion battery.
Finally, it should be noted that the above embodiments are only for illustrating the technical solution of the present invention and not for limiting the scope of the present invention, and although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that the present invention can be modified or substituted without departing from the spirit and scope of the technical solution of the present invention.
Claims (10)
1. The preparation method of the imidazole thiocarboxylate compound is characterized by comprising N, N ， -thiocarbonyldiimidazole and unsaturated alcohol react to produce imidazole thiocarboxylate compounds.
2. The method for producing an imidazole thiocarboxylate compound according to claim 1, wherein N, N ， And mixing thiocarbonyldiimidazole with the unsaturated alcohol at the temperature of 0 ℃, heating to room temperature for reaction, and finally carrying out post-treatment to obtain the imidazole thiocarboxylate compound.
3. The method for producing an imidazole thiocarboxylate compound according to claim 1, wherein the unsaturated alcohol is any one of allyl alcohol and propargyl alcohol.
4. The method for producing an imidazole thiocarboxylate compound according to claim 1, characterized in that the imidazole thiocarboxylate compound is at least one of compound 1 and compound 2:
5. the use of the imidazole thiocarboxylate compound prepared by the preparation method of the imidazole thiocarboxylate compound according to any one of claims 1 to 4 in a nonaqueous electrolyte.
6. The non-aqueous electrolyte comprises electrolyte salt, a non-aqueous solvent and an additive, and is characterized in that the additive comprises the imidazole thiocarboxylate compound prepared by the preparation method according to any one of claims 1 to 4.
7. The nonaqueous electrolytic solution according to claim 6, wherein the mass percentage of the imidazole thiocarboxylate compound in the nonaqueous electrolytic solution is 0.01% to 2.00%.
8. The nonaqueous electrolytic solution of claim 6, further comprising a film forming aid comprising at least one of vinylene carbonate, vinyl ethylene carbonate, vinyl sulfinate, 1, 3-propane sultone and vinyl sulfonate.
9. The nonaqueous electrolytic solution according to claim 6, wherein the electrolyte salt is a lithium salt or a sodium salt, and the mass percentage of the electrolyte salt in the nonaqueous electrolytic solution is 8% to 14%.
10. An alkali metal battery comprising a positive electrode material and a negative electrode material, characterized by further comprising the nonaqueous electrolyte according to any one of claims 6 to 9, wherein the negative electrode material is any one of lithium metal, a lithium alloy, sodium metal and a sodium alloy.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311537807.4A CN117567377A (en) | 2023-11-17 | 2023-11-17 | Preparation method and application of imidazole thiocarboxylate compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311537807.4A CN117567377A (en) | 2023-11-17 | 2023-11-17 | Preparation method and application of imidazole thiocarboxylate compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117567377A true CN117567377A (en) | 2024-02-20 |
Family
ID=89892996
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202311537807.4A Pending CN117567377A (en) | 2023-11-17 | 2023-11-17 | Preparation method and application of imidazole thiocarboxylate compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN117567377A (en) |
-
2023
- 2023-11-17 CN CN202311537807.4A patent/CN117567377A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107359369B (en) | Electrolyte and lithium ion battery | |
| CN110931865A (en) | Novel additive-containing electrolyte for lithium ion battery and lithium ion battery | |
| CN114552010B (en) | Additive for lithium metal battery, electrolyte and lithium metal battery | |
| CN108630989A (en) | Electrolyte and lithium ion battery | |
| CN113764737B (en) | Additive, electrolyte containing additive and lithium ion battery | |
| CN111934015B (en) | Non-aqueous electrolyte of lithium ion battery and lithium ion battery containing non-aqueous electrolyte | |
| CN114497743B (en) | Electrolyte applied to alkali metal battery and alkali metal battery thereof | |
| CN112151861A (en) | Battery cathode surface protection composition, electrolyte and application thereof | |
| CN113113668B (en) | Electrolyte additive, non-aqueous electrolyte containing electrolyte additive and lithium ion battery | |
| CN109119687B (en) | Electrolyte and electrochemical energy storage device | |
| CN109309248B (en) | Electrolyte solution and secondary battery | |
| CN115863768B (en) | Electrolyte and lithium metal battery containing same | |
| CN117059894A (en) | Electrolyte and alkali metal cell | |
| CN117039151A (en) | Lithium ion battery electrolyte and lithium ion battery containing same | |
| CN114566712B (en) | High-voltage lithium ion battery electrolyte containing lithium difluorophosphate, preparation method thereof and lithium ion battery | |
| CN113140792B (en) | High-energy-density lithium ion battery electrolyte and application thereof | |
| CN117567377A (en) | Preparation method and application of imidazole thiocarboxylate compound | |
| CN115133125A (en) | Method for improving solubility of lithium salt additive and electrolyte containing lithium salt additive | |
| CN111883827A (en) | Non-aqueous electrolyte of lithium ion battery and lithium ion battery | |
| CN116706237B (en) | Quick ion conductor additive, mixed electrolyte, sodium ion battery and vehicle | |
| CN117551055A (en) | Electrolyte additive, preparation method thereof, nonaqueous electrolyte and alkali metal battery | |
| CN117682972B (en) | Organic compound containing sulfonamide group and fluorinated group and application thereof | |
| CN113764736B (en) | Electrolyte for lithium ion battery, preparation method of electrolyte and lithium ion battery | |
| CN117497861B (en) | Lithium ion battery electrolyte and lithium ion battery | |
| CN114824484A (en) | Electrolyte for lithium metal battery and lithium metal battery using the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |