CN111333595A - Lithium acetylsulfanilate, preparation method thereof and application thereof in non-aqueous electrolyte - Google Patents
Lithium acetylsulfanilate, preparation method thereof and application thereof in non-aqueous electrolyte Download PDFInfo
- Publication number
- CN111333595A CN111333595A CN202010128402.5A CN202010128402A CN111333595A CN 111333595 A CN111333595 A CN 111333595A CN 202010128402 A CN202010128402 A CN 202010128402A CN 111333595 A CN111333595 A CN 111333595A
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- CN
- China
- Prior art keywords
- lithium
- acetylsulfanilate
- carbonate
- electrolyte
- under reduced
- 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 Lithium acetylsulfanilate Chemical compound 0.000 title claims abstract description 33
- 239000011255 nonaqueous electrolyte Substances 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 239000003792 electrolyte Substances 0.000 claims abstract description 23
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 19
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000001035 drying Methods 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 10
- 239000002798 polar solvent Substances 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 238000003756 stirring Methods 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000012046 mixed solvent Substances 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 239000003495 polar organic solvent Substances 0.000 claims abstract description 4
- XCVWCSLKKQOBGY-UHFFFAOYSA-N 2-acetyl-4-aminobenzenesulfonic acid Chemical compound CC(=O)C1=CC(N)=CC=C1S(O)(=O)=O XCVWCSLKKQOBGY-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000012043 crude product Substances 0.000 claims abstract description 3
- 239000000047 product Substances 0.000 claims abstract description 3
- 238000001953 recrystallisation Methods 0.000 claims abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 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
- SKIVFJLNDNKQPD-UHFFFAOYSA-N sulfacetamide Chemical compound CC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 SKIVFJLNDNKQPD-UHFFFAOYSA-N 0.000 claims description 7
- 229960002673 sulfacetamide Drugs 0.000 claims description 7
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 6
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 6
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 6
- 229940090181 propyl acetate Drugs 0.000 claims description 6
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 6
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 5
- 239000006258 conductive agent Substances 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- 239000011356 non-aqueous organic solvent Substances 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 3
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims description 3
- 229910052808 lithium carbonate Inorganic materials 0.000 claims description 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 2
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 239000008151 electrolyte solution Substances 0.000 claims 3
- 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
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 abstract description 4
- 229910013872 LiPF Inorganic materials 0.000 abstract description 4
- 101150058243 Lipf gene Proteins 0.000 abstract description 4
- 229910000040 hydrogen fluoride Inorganic materials 0.000 abstract description 4
- FFUQCRZBKUBHQT-UHFFFAOYSA-N phosphoryl fluoride Chemical compound FP(F)(F)=O FFUQCRZBKUBHQT-UHFFFAOYSA-N 0.000 abstract description 4
- 230000007547 defect Effects 0.000 abstract description 3
- 239000012535 impurity Substances 0.000 abstract description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract description 2
- 230000002349 favourable effect Effects 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 6
- 229910001290 LiPF6 Inorganic materials 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 239000007774 positive electrode material Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution 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
- YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 description 3
- 229960005164 acesulfame Drugs 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
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- 239000002033 PVDF binder Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004917 carbon fiber Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000012983 electrochemical energy storage Methods 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 239000007788 liquid 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
- 239000012265 solid product Substances 0.000 description 2
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 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
- 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
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
- 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
- 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
- 150000001450 anions Chemical class 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
- 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
- 229910052729 chemical element Inorganic materials 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
- 239000011530 conductive current collector Substances 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 238000009831 deintercalation Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000004090 dissolution 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
- 238000004519 manufacturing process Methods 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
- 239000000203 mixture Substances 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
- OBCUTHMOOONNBS-UHFFFAOYSA-N phosphorus pentafluoride Chemical compound FP(F)(F)(F)F OBCUTHMOOONNBS-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 239000002994 raw material 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910021384 soft carbon Inorganic materials 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- 239000002562 thickening agent Substances 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D291/00—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms
- C07D291/02—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms not condensed with other rings
- C07D291/06—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
- 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
-
- 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)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Inorganic Chemistry (AREA)
- Secondary Cells (AREA)
Abstract
The invention discloses a lithium acetylsulfanilate and a preparation method thereof, wherein the method comprises the following steps: (1) adding acetylsulfanilic acid into a reaction bottle, adding a proper amount of water, adding a lithium source in batches, and stirring for reaction; (2) drying under reduced pressure to obtain crude product of lithium acetylsulfanilate; (3) adding a polar organic solvent, and stirring for dissolving; (4) filtering to remove insoluble substances, removing the organic solvent under reduced pressure, selecting a mixed solvent of a strong polar solvent and a weak polar solvent for recrystallization, and drying under reduced pressure to obtain the product. The lithium acetylsulfanilate has excellent chemical stability, and can avoid LiPF when being applied to an electrolyte system6The electrolyte system contains hydrogen fluoride, phosphorus oxytrifluoride and other harmful impurities, and the structure of the lithium acetylsulfanilate contains C-C double bond and sulfonyl group, which is favorable for forming film on the electrode, so that the electrolyte system has the technical defect of containing hydrogen fluoride, phosphorus oxytrifluoride and other harmful impuritiesThe application of the lithium acetylsulfanilate in the electrolyte can effectively improve the comprehensive performance of the lithium ion battery.
Description
Technical Field
The invention relates to the field of electrochemical energy storage, in particular to a preparation method of lithium acetylsulfanilate and application of nonaqueous electrolyte containing the lithium acetylsulfanilate in an electrochemical energy storage device.
Background
The lithium ion battery electrolyte generally consists of electrolyte salt, solvent and functional additives. For lithium ion batteries, LiPF is generally used as the electrolyte currently used in commercial applications6As a supporting electrolyte. But LiPF6Unstable in chemical nature, at higher temperatures: (>55 ℃) or easily decomposes to generate hydrogen fluoride, phosphorus pentafluoride, phosphorus oxytrifluoride and other impurities when meeting with moisture, and causes the carbonate solvent to generate autocatalytic decomposition reaction. Thus, LiPF6The lithium ion battery as the conductive lithium salt of the electrolyte has poor high-temperature performance and limited service life. The method develops anions with more stable physicochemical properties, avoids the defect that the battery loses efficacy due to decomposition and deterioration of electrolyte in the working or storage process, and is of great importance for improving the comprehensive performance of the lithium ion battery.
Disclosure of Invention
In view of the problems of the background art, the present invention aims to provide a method for preparing lithium acetylsulfanilate.
The invention also aims to provide the application of the lithium sulfacetamide in the non-aqueous electrolyte.
In order to solve the technical problem, the structural general formula of the lithium sulfacetamide is shown as formula (I):
the invention provides a preparation method of the lithium acetylsulfanilate shown in the formula (I), which comprises the following steps:
(1) adding acetylsulfanilic acid (the preparation method is referred to patent document CN201380029410), adding a proper amount of water, adding a lithium source in batches, and stirring for reaction;
(2) drying under reduced pressure to obtain crude product of lithium acetylsulfanilate;
(3) adding a polar organic solvent, and stirring for dissolving;
(4) filtering to remove insoluble substances, removing the organic solvent under reduced pressure, selecting a mixed solvent of a strong polar solvent and a weak polar solvent for recrystallization, and drying under reduced pressure to obtain a product;
preferably, the lithium source in step (1) comprises lithium carbonate and lithium hydroxide.
Preferably, the organic solvent in step (3) includes acetonitrile, acetone, dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, ethyl acetate, propyl acetate, butyl acetate, diethyl ether, methyl tert-butyl ether, ethylene glycol dimethyl ether, dioxane, tetrahydrofuran, and dioxolane.
Preferably, the strongly polar solvent in step (4) comprises acetonitrile, acetone, dimethyl carbonate, diethyl carbonate, methyl ethyl carbonate, ethyl acetate, propyl acetate, butyl acetate, diethyl ether, methyl tert-butyl ether, tetrahydrofuran, ethylene glycol dimethyl ether and dioxane. The weak polar solvent includes dichloromethane, chloroform, n-hexane, cyclohexane, toluene, xylene, chlorobenzene, and fluorobenzene.
The invention provides an application of lithium acetylsulfanilate in a non-aqueous electrolyte, namely an application of lithium acetylsulfanilate serving as an electrolyte in a lithium battery and a lithium ion battery.
In order to realize the technical scheme, the invention provides an electrolyte of lithium acetylsulfanilate, which comprises a conductive lithium salt, a non-aqueous organic solvent and an additive, wherein the conductive lithium salt comprises the lithium acetylsulfanilate.
The mass percentage of the acesulfame lithium in the electrolyte is 0.5-40%, preferably 0.5-15%.
Preferably, the conductive lithium salt further comprises LiBF4、LiPF6、LiAsF6、LiClO4、LiSO3CF3、LiB(C2O4)2、LiBF2C2O4、LiN(SO2CF3)2、LiN(SO2F)2One or more of (a).
Preferably, the non-aqueous organic solvent is one or more of ethylene carbonate, propylene carbonate, dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, gamma-butyrolactone, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, ethyl propionate, propyl propionate and butyl propionate.
Preferably, the additive is one or more of vinylene carbonate, ethylene carbonate, fluoroethylene carbonate, difluoroethylene carbonate, 1, 3-propane sultone, 1, 4-butane sultone, ethylene sulfate, propylene sulfate, ethylene sulfite, propylene sulfite, succinonitrile, adiponitrile and 1, 2-cyanoethoxy ethane.
The present invention also provides a lithium secondary battery: the electrolyte consists of a positive plate, a negative plate, a diaphragm and the electrolyte containing the lithium sulfacetamide; the positive plate and the negative plate comprise active materials, conductive agents, current collectors and binding agents for combining the active materials and the conductive agents with the current collectors.
Preferably, the positive electrode sheet comprises a positive electrode active material capable of reversibly intercalating/deintercalating lithium ions, the positive electrode active material is preferably a lithium composite metal oxide, and the metal oxide comprises oxides of nickel, cobalt, manganese elements and any proportion combination thereof; the positive active material further comprises one or more chemical elements including Mg, Al, Ti, Sn, V, Ge, Ga, B, Zr, Cr, Fe, Sr and rare earth elements; the positive electrode active material further includes a polyanionic lithium compound LiMx(PO4)y(M is Ni, Co, Mn, Fe, Ti, V, x is more than or equal to 0 and less than or equal to 5, and y is more than or equal to 0 and less than or equal to 5).
Preferably, the negative electrode sheet comprises a negative electrode active material capable of accepting or releasing lithium ions, and the negative electrode active material comprises lithium metal, lithium alloy, crystalline carbon, amorphous carbon, carbon fiber, hard carbon and soft carbon; wherein the crystalline carbon comprises natural graphite, graphitized coke, graphitized MCMB and graphitized mesophase pitch carbon fiber; the lithium alloy comprises an alloy of lithium and metals of aluminum, zinc, silicon, tin, gallium and antimony.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to specific embodiments.
The invention is illustrated in detail by the following exemplary embodiments. It should be understood that the scope of the present invention should not be limited to the scope of the embodiments. Any variations or modifications which do not depart from the gist of the invention will be understood to those skilled in the art. The scope of the invention is to be determined by the scope of the appended claims.
Example 1
A500 mL reaction flask was charged with 81.5g (0.5mol) of acesulfame, 200mL of deionized water, and 19.24g (0.26mol) of lithium carbonate were added in portions and the reaction was stirred until the system was not acidic. Drying under reduced pressure to obtain white solid, adding 200mL of dimethyl carbonate, stirring for full dissolution, standing, filtering to obtain clear liquid, drying under reduced pressure to obtain white solid, recrystallizing with dimethyl carbonate/toluene mixed solvent, filtering, and drying under reduced pressure to obtain 82.8g of white solid product with yield of 98%.
Example 2
A500 mL reaction flask was charged with 81.5g (0.5mol) of acesulfame, 200mL of deionized water, 22.26g (0.53mol) of sodium carbonate in portions, and the reaction was stirred until the system was not acidic. Drying under reduced pressure to obtain white solid, adding 200mL ethyl acetate, stirring for fully dissolving, standing, filtering to obtain clear liquid, drying under reduced pressure to obtain white solid, recrystallizing with ethyl acetate/dichloromethane mixed solvent, filtering, and drying under reduced pressure to obtain 81.12g white solid product with a yield of 96%.
Example 3
(1) Preparation of the electrolyte
In an argon atmosphere glove box (H)2O<1ppm), mixing an organic solvent according to the mass ratio of EC (ethylene carbonate) to DMC (dimethyl carbonate): EMC (methyl ethyl carbonate) 40: 20 was mixed with lithium acetylsulfanilate (14%) and 1% by weight VC (vinylene carbonate), 2% PS (propane sultone) and 3% FEC (fluoroethylene carbonate) were addedEster), 3% SN (succinonitrile). The raw materials are added in sequence and fully and uniformly stirred to obtain the lithium secondary battery electrolyte (free acid) of the invention<15ppm, water content<10ppm)。
(2) Preparation of positive pole piece
Dissolving 3% polyvinylidene fluoride (PVDF) in 1-methyl-2-pyrrolidone solution, and mixing with 94% LiCoO2And 3% of conductive agent carbon black are added into the solution and uniformly mixed, and the mixed slurry is coated on two sides of the aluminum foil, dried and rolled to obtain the positive pole piece. Other cathode materials LiMn2O4、LiFePO4、LiNi0.5Co0.3Mn0.2、LiNi0.3Co0.3Mn0.3Prepared by the same method.
(3) Preparation of negative pole piece
Dissolving 4% by mass of SBR binder and 1% by mass of CMC thickener in an aqueous solution, adding 95% by mass of graphite into the solution, uniformly mixing, coating the mixed slurry on two sides of a copper foil, drying and rolling to obtain the negative pole piece. Other negative electrode materials Li4Ti5O12Prepared in a similar way.
(4) Production of lithium ion battery
And (3) preparing the prepared positive pole piece, negative pole piece and isolating membrane into a square battery core in a winding mode, packaging by adopting a polymer, filling the prepared electrolyte, and preparing the lithium ion battery with the capacity of 1600mAh through the processes of formation and the like.
(5) Battery performance testing
Cycling test conditions: carrying out charge-discharge cycle test on the battery at the charge-discharge rate of 1/1C; high temperature storage test conditions: firstly, the formed battery is charged and discharged once at the normal temperature by 1C, then the battery is fully charged by 1C and then stored at high temperature, and after the battery is completely cooled, the taken out battery is subjected to a discharge test by 1C.
Examples 6 to 16 the parameters and preparation methods were the same as in example 5 except for the following table parameters.
TABLE 1 examples 3 to 10 and comparative examples 1 to 9
As can be seen from the results of examples 3 to 6 and comparative examples 1 to 4, the battery using lithium acetylsulfanilate was compared to the battery using LiPF with the same solvent and additive components6The cycle performance and the storage performance of the battery are obviously improved. As can be seen from the results of examples 7 to 10 and comparative examples 2 to 3, and comparative example 6 and comparative example 8, lithium acetylsulfanilate and LiPF6When the composite material is used as conductive lithium salt, the cycle performance and the storage performance of the corresponding battery are also better than those of the LiPF used alone6The battery of (2) is more excellent. From the results of comparative examples 5-10, it can be seen that the chemical and electrochemical stability of the lithium salt has a more significant effect on the battery performance with less additives in the electrolyte formulation. The lithium acetylsulfanilate has excellent chemical stability and avoids LiPF6The electrolyte system contains the technical defects of harmful impurities such as hydrogen fluoride, phosphorus oxyfluoride and the like, and the structure of the lithium acetylsulfanilate contains C-C double bonds and sulfonyl groups, so that the film formation of an electrode is facilitated, and the comprehensive performance of the lithium acetylsulfanilate can be effectively improved when the lithium acetylsulfanilate is applied to the electrolyte.
While the foregoing is directed to the preferred embodiment of the present invention, it will be understood by those skilled in the art that various changes and modifications may be made without departing from the spirit and scope of the invention.
Claims (10)
1. The structure general formula of the lithium acetylsulfanilate is shown as the formula (I):
2. a method of preparing the lithium sulfacetamide of claim 1, comprising the steps of:
(1) adding acetylsulfanilic acid into a reaction bottle, adding a proper amount of water, adding a lithium source in batches, and stirring for reaction;
(2) drying under reduced pressure to obtain crude product of lithium acetylsulfanilate;
(3) adding a polar organic solvent, and stirring for dissolving;
(4) filtering to remove insoluble substances, removing the organic solvent under reduced pressure, selecting a mixed solvent of a strong polar solvent and a weak polar solvent for recrystallization, and drying under reduced pressure to obtain the product.
3. The method for preparing lithium acetylsulfanilate as claimed in claim 2, wherein: the lithium source in the step (1) comprises lithium carbonate and lithium hydroxide.
4. The method for preparing lithium acetylsulfanilate as claimed in claim 2, wherein: the polar organic solvent in the step (3) comprises acetonitrile, acetone, dimethyl carbonate, diethyl carbonate, methyl ethyl carbonate, ethyl acetate, propyl acetate, butyl acetate, diethyl ether, methyl tert-butyl ether, ethylene glycol dimethyl ether, dioxane, tetrahydrofuran and dioxolane.
5. The method for preparing lithium acetylsulfanilate as claimed in claim 2, wherein: the strong polar solvent in the step (4) comprises acetonitrile, acetone, dimethyl carbonate, diethyl carbonate, methyl ethyl carbonate, ethyl acetate, propyl acetate, butyl acetate, diethyl ether, methyl tert-butyl ether, tetrahydrofuran, ethylene glycol dimethyl ether and dioxane; the weak polar solvent includes dichloromethane, chloroform, n-hexane, cyclohexane, toluene, xylene, chlorobenzene, and fluorobenzene.
6. The application of the lithium acetylsulfanilate in the non-aqueous electrolyte is taken as the electrolyte.
7. An electrolyte containing lithium acetylsulfanilate comprises a conductive lithium salt, a non-aqueous organic solvent and an additive, and is characterized in that: the conductive lithium salt includes lithium acetylsulfanilate.
8. The lithium sulfacetamide-containing electrolyte solution according to claim 7, wherein: the mass percentage of the lithium acetylsulfanilate in the electrolyte is 0.5-40%.
9. The lithium sulfacetamide-containing electrolyte solution according to claim 8, wherein: the non-aqueous organic solvent is one or more of ethylene carbonate, propylene carbonate, dimethyl carbonate, diethyl carbonate, methyl ethyl carbonate, gamma-butyrolactone, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, ethyl propionate, propyl propionate and butyl propionate.
10. A lithium secondary battery comprising a positive electrode sheet, a negative electrode sheet, a separator and the lithium sulfacetamide-containing electrolyte solution according to any one of claims 7 to 8, the positive electrode sheet and the negative electrode sheet comprising an active material, a conductive agent, a current collector, and a binder for binding the active material and the conductive agent to the current collector.
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| CN111934014A (en) * | 2020-08-27 | 2020-11-13 | 珠海市赛纬电子材料股份有限公司 | Electrolyte and lithium ion battery containing same |
| CN113135947A (en) * | 2021-03-11 | 2021-07-20 | 常德市大度新材料有限公司 | Lithium acetylsulfanilate complex, preparation method thereof and application thereof in non-aqueous electrolyte |
| CN113363581A (en) * | 2021-06-16 | 2021-09-07 | 珠海市赛纬电子材料股份有限公司 | Non-aqueous electrolyte and secondary battery thereof |
| CN114436992A (en) * | 2021-12-29 | 2022-05-06 | 常德市大度新材料有限公司 | Acetamsulfate, preparation method thereof and application thereof in non-aqueous electrolyte |
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| WO2022262232A1 (en) * | 2021-06-16 | 2022-12-22 | 珠海市赛纬电子材料股份有限公司 | Non-aqueous electrolyte and secondary battery |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111934014A (en) * | 2020-08-27 | 2020-11-13 | 珠海市赛纬电子材料股份有限公司 | Electrolyte and lithium ion battery containing same |
| CN111934014B (en) * | 2020-08-27 | 2022-09-27 | 珠海市赛纬电子材料股份有限公司 | Electrolyte and lithium ion battery containing same |
| CN113135947A (en) * | 2021-03-11 | 2021-07-20 | 常德市大度新材料有限公司 | Lithium acetylsulfanilate complex, preparation method thereof and application thereof in non-aqueous electrolyte |
| CN113135947B (en) * | 2021-03-11 | 2022-08-16 | 常德市大度新材料有限公司 | Lithium acetylsulfanilate complex, preparation method thereof and application thereof in non-aqueous electrolyte |
| WO2022196375A1 (en) | 2021-03-17 | 2022-09-22 | 三井化学株式会社 | Nonaqueous secondary battery and method for producing nonaqueous secondary battery |
| CN113363581A (en) * | 2021-06-16 | 2021-09-07 | 珠海市赛纬电子材料股份有限公司 | Non-aqueous electrolyte and secondary battery thereof |
| WO2022262232A1 (en) * | 2021-06-16 | 2022-12-22 | 珠海市赛纬电子材料股份有限公司 | Non-aqueous electrolyte and secondary battery |
| WO2022262233A1 (en) * | 2021-06-16 | 2022-12-22 | 珠海市赛纬电子材料股份有限公司 | Non-aqueous electrolyte and secondary battery thereof |
| CN114436992A (en) * | 2021-12-29 | 2022-05-06 | 常德市大度新材料有限公司 | Acetamsulfate, preparation method thereof and application thereof in non-aqueous electrolyte |
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