CN113135947A - 乙酰磺胺酸锂络合物及其制备方法和其在非水电解液中的应用 - Google Patents
乙酰磺胺酸锂络合物及其制备方法和其在非水电解液中的应用 Download PDFInfo
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- CN113135947A CN113135947A CN202110267365.0A CN202110267365A CN113135947A CN 113135947 A CN113135947 A CN 113135947A CN 202110267365 A CN202110267365 A CN 202110267365A CN 113135947 A CN113135947 A CN 113135947A
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- China
- Prior art keywords
- complex
- lithium
- acetylsulfanilate
- carbonate
- boron trifluoride
- 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.)
- Granted
Links
- -1 Lithium acetylsulfanilate Chemical compound 0.000 title claims abstract description 69
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 239000011255 nonaqueous electrolyte Substances 0.000 title abstract description 5
- 239000003792 electrolyte Substances 0.000 claims abstract description 21
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims abstract description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 3
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 3
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Substances FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 18
- 229910015900 BF3 Inorganic materials 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- OBCUTHMOOONNBS-UHFFFAOYSA-N phosphorus pentafluoride Chemical compound FP(F)(F)(F)F OBCUTHMOOONNBS-UHFFFAOYSA-N 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 9
- 229910052744 lithium Inorganic materials 0.000 claims description 8
- 229910003002 lithium salt Inorganic materials 0.000 claims description 8
- 159000000002 lithium salts Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 6
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 5
- 239000006258 conductive agent Substances 0.000 claims description 5
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000011149 active material Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- FZUIUHFZKOQKHQ-UHFFFAOYSA-N diethyl carbonate;trifluoroborane Chemical compound FB(F)F.CCOC(=O)OCC FZUIUHFZKOQKHQ-UHFFFAOYSA-N 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 3
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 3
- 239000011356 non-aqueous organic solvent Substances 0.000 claims description 3
- 229940090181 propyl acetate Drugs 0.000 claims description 3
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 3
- QGXZSRUGDCPUDO-UHFFFAOYSA-N 1,3-dioxolan-2-one;trifluoroborane Chemical compound FB(F)F.O=C1OCCO1 QGXZSRUGDCPUDO-UHFFFAOYSA-N 0.000 claims description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- VEWIGYNQVZOINO-UHFFFAOYSA-N C(OCC)(OC)=O.B(F)(F)F Chemical compound C(OCC)(OC)=O.B(F)(F)F VEWIGYNQVZOINO-UHFFFAOYSA-N 0.000 claims description 2
- MEMUCXUKCBNISQ-UHFFFAOYSA-N acetonitrile;trifluoroborane Chemical compound CC#N.FB(F)F MEMUCXUKCBNISQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000011530 conductive current collector Substances 0.000 claims description 2
- SLCLABDXYGNNOO-UHFFFAOYSA-N dimethyl carbonate;trifluoroborane Chemical compound FB(F)F.COC(=O)OC SLCLABDXYGNNOO-UHFFFAOYSA-N 0.000 claims description 2
- 239000008151 electrolyte solution Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- RSESBNOXGXDSRO-UHFFFAOYSA-N C(OCC)(OC)=O.P(F)(F)(F)(F)F Chemical compound C(OCC)(OC)=O.P(F)(F)(F)(F)F RSESBNOXGXDSRO-UHFFFAOYSA-N 0.000 claims 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 abstract description 10
- 229910001416 lithium ion Inorganic materials 0.000 abstract description 10
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 230000002349 favourable effect Effects 0.000 abstract description 2
- SAPIQCCFEBULSH-UHFFFAOYSA-M lithium;sulfamate Chemical compound [Li+].NS([O-])(=O)=O SAPIQCCFEBULSH-UHFFFAOYSA-M 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 7
- 238000012360 testing method Methods 0.000 description 5
- 229910013872 LiPF Inorganic materials 0.000 description 4
- 229910001290 LiPF6 Inorganic materials 0.000 description 4
- 101150058243 Lipf gene Proteins 0.000 description 4
- 239000007774 positive electrode material Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 3
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 3
- SBLRHMKNNHXPHG-UHFFFAOYSA-N 4-fluoro-1,3-dioxolan-2-one Chemical compound FC1COC(=O)O1 SBLRHMKNNHXPHG-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910000733 Li alloy Inorganic materials 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000011572 manganese Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000007773 negative electrode material Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 239000002033 PVDF binder Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000004917 carbon fiber Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000012983 electrochemical energy storage Methods 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000001989 lithium alloy Substances 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000011268 mixed slurry Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 2
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 description 2
- SKIVFJLNDNKQPD-UHFFFAOYSA-N sulfacetamide Chemical compound CC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 SKIVFJLNDNKQPD-UHFFFAOYSA-N 0.000 description 2
- 229960002673 sulfacetamide Drugs 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- ZPFAVCIQZKRBGF-UHFFFAOYSA-N 1,3,2-dioxathiolane 2,2-dioxide Chemical compound O=S1(=O)OCCO1 ZPFAVCIQZKRBGF-UHFFFAOYSA-N 0.000 description 1
- WDXYVJKNSMILOQ-UHFFFAOYSA-N 1,3,2-dioxathiolane 2-oxide Chemical compound O=S1OCCO1 WDXYVJKNSMILOQ-UHFFFAOYSA-N 0.000 description 1
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- XCVWCSLKKQOBGY-UHFFFAOYSA-N 2-acetyl-4-aminobenzenesulfonic acid Chemical group CC(=O)C1=CC(N)=CC=C1S(O)(=O)=O XCVWCSLKKQOBGY-UHFFFAOYSA-N 0.000 description 1
- DCWQZPJHHVLHSV-UHFFFAOYSA-N 3-ethoxypropanenitrile Chemical compound CCOCCC#N DCWQZPJHHVLHSV-UHFFFAOYSA-N 0.000 description 1
- DSMUTQTWFHVVGQ-UHFFFAOYSA-N 4,5-difluoro-1,3-dioxolan-2-one Chemical compound FC1OC(=O)OC1F DSMUTQTWFHVVGQ-UHFFFAOYSA-N 0.000 description 1
- OQXNUCOGMMHHNA-UHFFFAOYSA-N 4-methyl-1,3,2-dioxathiolane 2,2-dioxide Chemical compound CC1COS(=O)(=O)O1 OQXNUCOGMMHHNA-UHFFFAOYSA-N 0.000 description 1
- SJHAYVFVKRXMKG-UHFFFAOYSA-N 4-methyl-1,3,2-dioxathiolane 2-oxide Chemical compound CC1COS(=O)O1 SJHAYVFVKRXMKG-UHFFFAOYSA-N 0.000 description 1
- FYXYFSLLIUHARO-UHFFFAOYSA-N C(OC(C)C)(O)=O.P(F)(F)(F)(F)F Chemical compound C(OC(C)C)(O)=O.P(F)(F)(F)(F)F FYXYFSLLIUHARO-UHFFFAOYSA-N 0.000 description 1
- HBXAEWKXPWGNSN-UHFFFAOYSA-N C1(OCCO1)=O.P(F)(F)(F)(F)F Chemical compound C1(OCCO1)=O.P(F)(F)(F)(F)F HBXAEWKXPWGNSN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 229910002986 Li4Ti5O12 Inorganic materials 0.000 description 1
- 229910013098 LiBF2 Inorganic materials 0.000 description 1
- 229910032387 LiCoO2 Inorganic materials 0.000 description 1
- 229910052493 LiFePO4 Inorganic materials 0.000 description 1
- 229910013406 LiN(SO2CF3)2 Inorganic materials 0.000 description 1
- 229910013426 LiN(SO2F)2 Inorganic materials 0.000 description 1
- 229910012743 LiNi0.5Co0.3Mn0.2 Inorganic materials 0.000 description 1
- 229910002097 Lithium manganese(III,IV) oxide Inorganic materials 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 description 1
- 229960005164 acesulfame Drugs 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 1
- 229910002065 alloy metal Inorganic materials 0.000 description 1
- 229910003481 amorphous carbon Inorganic materials 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000009831 deintercalation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000013538 functional additive Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910021385 hard carbon Inorganic materials 0.000 description 1
- 238000009830 intercalation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 229910001540 lithium hexafluoroarsenate(V) Inorganic materials 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
- QSZMZKBZAYQGRS-UHFFFAOYSA-N lithium;bis(trifluoromethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F QSZMZKBZAYQGRS-UHFFFAOYSA-N 0.000 description 1
- MCVFFRWZNYZUIJ-UHFFFAOYSA-M lithium;trifluoromethanesulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)F MCVFFRWZNYZUIJ-UHFFFAOYSA-M 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000002931 mesocarbon microbead Substances 0.000 description 1
- 239000011302 mesophase pitch Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910021382 natural graphite Inorganic materials 0.000 description 1
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910021384 soft carbon Inorganic materials 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6544—Six-membered rings
-
- 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
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Abstract
Description
技术领域
本发明涉及电化学储能领域,更具体地,本发明涉及一种乙酰磺胺酸锂络合物的制备方法及含有该物质的非水电解液在电化学储能器件中的应用。
背景技术
锂离子电池电解液一般由电解质盐、溶剂和功能性添加剂组成。对于锂离子电池,目前商品化应用的电解液一般使用LiPF6作为支持电解质。但是LiPF6化学性质不稳定,在较高的温度下(>55℃),或者遇潮容易分解产生氟化氢等杂质,导致LiPF6作为电解液导电锂盐的锂离子电池高温性能较差,使用寿命受限。
发明内容
鉴于背景技术所存在的问题,本发明的一个目的在于提供一种乙酰磺胺酸锂络合物及其制备方法。
本发明的另一个目的是提供乙酰磺胺酸锂络合物在非水电解液中的应用。
为解决上述的技术问题,本发明所述乙酰磺胺酸锂络合物的结构通式为式(Ⅰ)和(Ⅱ)所示:
其中,R1=甲基、乙基、丙基、异丙基、正丁基、异丁基、乙烯基、烯丙基、乙炔基、苯基、或4-氟苯基。
本发明提供上述式(Ⅰ)和(Ⅱ)乙酰磺胺酸锂络合物的制备方法,包括以下步骤:
(1)乙酰磺胺酸锂制备(参考文献中国专利申请号2020101284025,公开号:CN111333595A);
(2)反应瓶中加入乙酰磺胺酸锂,加入有机溶剂,搅拌,控制温度,加入氟硼化合物或者五氟化磷化合物;
(2)过滤除去不溶物;
(3)减压浓缩干燥,得到乙酰磺胺酸锂络合物或者含乙酰磺胺酸锂络合物的溶液。
优选的,步骤(2)所述的有机溶剂包括乙腈、丙酮、碳酸二甲酯、碳酸二乙酯、碳酸甲乙酯、碳酸乙烯酯、碳酸丙烯酯、乙酸乙酯、乙酸丙酯、乙酸丁酯、乙醚、甲基叔丁基醚、乙二醇二甲醚、二氧六环、四氢呋喃、二氧戊烷。
优选的,步骤(2)所述氟硼化合物包括三氟化硼和三氟化硼络合物,其中,三氟化硼络合物优选三氟化硼乙醚络合物、三氟化硼乙腈络合物、三氟化硼碳酸二甲酯络合物、三氟化硼碳酸二乙酯络合物、三氟化硼碳酸甲乙酯络合物、三氟化硼碳酸乙烯酯络合物。
优选的,步骤(2)所述五氟化磷化合物包括五氟化磷和五氟化磷络合物,其中,五氟化磷络合物优选五氟化磷乙醚络合物、五氟化磷乙腈络合物、五氟化磷碳酸二甲酯络合物、五氟化磷碳酸二乙酯络合物、五氟化磷碳酸甲乙酯络合物、五氟化磷碳酸乙烯酯络合物。
优选的,步骤(2)所述温度为-20~60℃,更优选为-10~30℃。
本发明提供的乙酰磺胺酸锂络合物在非水电解液中的应用,即在锂电池和锂离子电池中作为电解质的应用。
为了实现上述技术方案,本发明提供一种乙酰磺胺酸锂络合物的电解液,包括导电锂盐、非水有机溶剂和添加剂,导电锂盐包括乙酰磺胺酸锂络合物。
乙酰磺胺酸锂络合物在电解液中的质量百分含量为0.1%~40%,优选0.2%~15%。
优选的,所述的导电锂盐还包括LiBF4、LiPF6、LiAsF6、LiClO4、LiSO3CF3、LiB(C2O4)2、LiBF2C2O4、LiN(SO2CF3)2、LiN(SO2F)2中的一种或多种。
优选的,所述非水有机溶剂为碳酸乙烯酯、碳酸丙烯酯、碳酸二甲酯、碳酸二乙酯、碳酸甲乙酯、γ-丁内酯、乙酸甲酯、乙酸乙酯、乙酸丙酯、乙酸丁酯、丙酸乙酯、丙酸丙酯、丙酸丁酯中的一种或几种。
优选的,所述添加剂为碳酸亚乙烯酯、碳酸乙烯亚乙酯、氟代碳酸乙烯酯、二氟代碳酸乙烯酯、1,3-丙磺酸内酯、1,4-丁磺酸内酯、硫酸乙烯酯、硫酸丙烯酯、亚硫酸乙烯酯、亚硫酸丙烯酯、丁二腈、己二腈、1,2-氰乙氧基乙烷中的一种或几种。
本发明还提供了一种锂二次电池:包括正极片、负极片、隔膜以及本发明所述的含有乙酰磺胺酸锂络合物的电解液构成;正极片和负极片包含活性材料、导电剂、集流体、将所述活性材料和导电剂与所述集流体结合的结合剂。
优选的,所述正极片包括能够可逆地嵌入/脱嵌锂离子的正极活性材料,正极活性材料优选为锂的复合金属氧化物,金属氧化物包括镍、钴、锰元素及其任何比例组合的氧化物;正极活性材料还进一步包括化学元素中的一种或者若干种,所述化学元素包括有Mg、Al、Ti、Sn、V、Ge、Ga、B、Zr、Cr、Fe、Sr和稀土元素;正极活性材料还进一步包括聚阴离子锂化合物LiMx(PO4)y(M为Ni、Co、Mn、Fe、Ti、V,0≤x≤5,0≤y≤5)。
优选的,所述负极片包括能够接受或释放锂离子的负极活性材料,所述负极活性材料包括锂金属、锂合金、结晶碳、无定型碳、碳纤维、硬碳、软碳;其中结晶碳包括天然石墨、石墨化焦炭、石墨化MCMB、石墨化中间相沥青碳纤维;所述的锂合金包括锂和铝、锌、硅、锡、镓、锑金属的合金。
具体实施方式
下面将结合具体实施例对本发明实施例中的技术方案进行清楚、完整地描述。
下面通过示例性的实施例具体说明本发明。应当理解,本发明的范围不应局限于实施例的范围。任何不偏离本发明主旨的变化或改变能够为本领域的技术人员所理解。本发明的保护范围由所附权利要求的范围确定。
实施例1
1000mL反应瓶中加入84.5g(0.5mol)乙酰磺胺酸锂,加入500mL碳酸二甲酯,分批通入34g(0.5mol)三氟化硼,温度控制25℃,搅拌反应8个小时。减压过滤得到澄清溶液,控温60度减压除去溶剂,得到116g产品,产率98%。
实施例2
1000mL反应瓶中加入84.5g(0.5mol)乙酰磺胺酸锂,加入214g碳酸二乙酯,分批加入93g(0.5mol)三氟化硼碳酸二乙酯络合物,温度控制25℃,搅拌反应8个小时。减压过滤得到390g澄清溶液产品(三氟化硼乙酰磺胺酸锂质量百分含量30%),产率99%。
实施例3
2000mL反应瓶中加入84.5g(0.5mol)乙酰磺胺酸锂,加入682碳酸二乙酯,分批通入63g(0.5mol)五氟化磷,温度控制25℃,搅拌反应8个小时。减压过滤得到973g澄清溶液产品(五氟化磷乙酰磺胺酸锂质量百分含量30%),产率99%。
实施例4
(1)电解液的制备
在氩气氛围的手套箱中(H2O<1ppm),将有机溶剂按质量比为EC(碳酸乙烯酯)∶DMC(碳酸二甲酯):EMC(碳酸甲乙酯)=40∶40∶20与三氟化硼乙酰磺胺酸锂(19.5%)混合,加入总重量1%的VC(碳酸亚乙烯酯),2%的PS(丙磺酸内酯),3%的FEC(氟代碳酸乙烯酯),3%的SN(丁二腈)。将上述各原料依次加入,充分搅拌均匀,即得到本发明所述的锂二次电池电解液(游离酸<15ppm,水分<10ppm)。
(2)正极极片的制备
将质量百分比为3%的聚偏氟乙烯(PVDF)溶解于1-甲基-2-吡咯烷酮溶液中,将质量百分比94%的LiCoO2和3%的导电剂炭黑加入上述溶液并混合均匀,将混制的浆料涂布在铝箔的两面后,烘干、滚压后得到正极极片。其它正极材料LiMn2O4、LiFePO4、LiNi0.5Co0.3Mn0.2、LiNi0.3Co0.3Mn0.3按同样的方法制备。
(3)负极极片的制备
将质量百分比为4%的SBR粘结剂,质量百分比为1%的CMC增稠剂溶于水溶液中,将质量百分比为95%的石墨加入上述溶液,混合均匀,将混制的浆料涂布在铜箔的两面后,烘干、滚压后得到负极极片。其它负极材料Li4Ti5O12按类似的方法制备。
(4)锂离子电池的制作
将上述制备的正极极片、负极极片和隔离膜以卷绕方式制成方形电芯,采用聚合物包装,灌注上述制备的电解液,经化成等工艺后制成容量为1600mAh的锂离子电池。
(5)电池性能测试
循环测试条件:以1/1C充放电的倍率对电池进行充放电循环测试;高温储存测试条件:首先将化成完毕的电池在常温状态下以1C充放电一次,再以1C将电池充满电后进行高温保存,待电池完全冷却后,将取出的电池以1C进行放电测试。
实施例5~15,对比例1~12除下表参数外,其他参数及制备方法同实施例4。
表1实施例4~15及对比例1~12
从实施例4~7、对比例1~3和对比例5的结果可以看出,在溶剂和添加剂组分相同的情况下,使用乙酰磺胺酸锂络合物的电池比使用LiPF6的电池循环性能和储存性能提升较为明显。从实施例8~15和对比例1~6的结果可以看出,乙酰磺胺酸锂络合物和LiPF6复合作为导电锂盐使用,相应电池的循环性能和储存性能也比单独使用LiPF6的电池更为优越。从对比例3~10的结果可以看出,电解液配方中添加剂较少的情况下,锂盐的化学和电化学稳定性对电池性能的影响更加明显。从实施例12~15和对比例9~12的结果可以看出,乙酰磺胺酸锂络合物和乙酰磺胺酸锂对比,前者相应电池的循环性能和储存性能更为优越。乙酰磺胺酸锂络合物和乙酰磺胺酸锂均具有优越的化学稳定性,避免了LiPF6电解液体系中含有氟化氢等危害性杂质的技术弊端,乙酰磺胺酸基团中含有C=C双键和磺酰基基团,以及络合物结构中含有的B-F和P-F基团,有利于在电极形成稳定性好,阻抗低的界面膜,因此乙酰磺胺酸锂络合物在电解液中应用可以有效改善锂离子电池的综合性能。此外乙酰磺胺酸锂络合物比乙酰磺胺酸锂在有机溶剂中具有较高的溶解度,更有利于电解液生产加工。
以上所述是本发明的优选实施方式,应当指出,对于本技术领域的普通技术人员来说,在不脱离本发明原理的前提下,还可以做出若干改进和润饰,这些改进和润饰也视为本发明的保护范围。
Claims (10)
2.一种制备如权利要求1所述乙酰磺胺酸锂络合物的方法,其特征在于,包括以下步骤:
(1)制备乙酰磺胺酸锂;
(2)向反应瓶中加入乙酰磺胺酸锂,加入有机溶剂,搅拌,控制温度,加入氟硼化合物或者五氟化磷化合物;
(3)过滤除去不溶物;
(4)减压浓缩干燥,得到乙酰磺胺酸锂络合物或者含乙酰磺胺酸锂络合物的溶液。
3.如权利要求2所述乙酰磺胺酸锂络合物的制备方法,其特征在于:步骤(2)所述的有机溶剂包括乙腈、丙酮、碳酸二甲酯、碳酸二乙酯、碳酸甲乙酯、碳酸乙烯酯、碳酸丙烯酯、乙酸乙酯、乙酸丙酯、乙酸丁酯、乙醚、甲基叔丁基醚、乙二醇二甲醚、二氧六环、四氢呋喃、二氧戊烷中的一种。
4.如权利要求2所述乙酰磺胺酸锂络合物的制备方法,其特征在于:步骤(2)所述氟硼化合物包括三氟化硼和三氟化硼络合物中的一种或两种的混合物。
5.如权利要求4所述乙酰磺胺酸锂络合物的制备方法,其特征在于:所述三氟化硼络合物包括三氟化硼乙醚络合物、三氟化硼乙腈络合物、三氟化硼碳酸二甲酯络合物、三氟化硼碳酸二乙酯络合物、三氟化硼碳酸甲乙酯络合物、三氟化硼碳酸乙烯酯络合物。
6.如权利要求2所述乙酰磺胺酸锂络合物的制备方法,其特征在于:步骤(2)所述五氟化磷化合物包括五氟化磷和五氟化磷络合物,所述五氟化磷络合物包括五氟化磷乙醚络合物、五氟化磷乙腈络合物、五氟化磷碳酸二甲酯络合物、五氟化磷碳酸二乙酯络合物、五氟化磷碳酸甲乙酯络合物、五氟化磷碳酸乙烯酯络合物。
7.如权利要求6所述乙酰磺胺酸锂络合物的制备方法,其特征在于:步骤(2)所述温度为-20~60℃。
8.一种乙酰磺胺酸锂络合物的电解液,包括导电锂盐、非水有机溶剂和添加剂,所述导电锂盐包括权要求1-8任一项所述的乙酰磺胺酸锂络合物。
9.一种锂二次电池:包括正极片、负极片、隔膜以及含有权利要求1-8任一项所述的乙酰磺胺酸锂络合物的电解液构成;正极片和负极片包含活性材料、导电剂、集流体、将所述活性材料和导电剂与所述集流体结合的结合剂。
10.权利要求1-8任一项所述的乙酰磺胺酸锂络合物作为电解质在非水电解液中的应用。
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