CN112421109A - 一种环状磺酸酯类锂离子电池电解液添加剂、其制备方法与应用 - Google Patents
一种环状磺酸酯类锂离子电池电解液添加剂、其制备方法与应用 Download PDFInfo
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- CN112421109A CN112421109A CN202011303478.3A CN202011303478A CN112421109A CN 112421109 A CN112421109 A CN 112421109A CN 202011303478 A CN202011303478 A CN 202011303478A CN 112421109 A CN112421109 A CN 112421109A
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- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 229910001416 lithium ion Inorganic materials 0.000 title claims abstract description 47
- 125000004122 cyclic group Chemical group 0.000 title claims abstract description 21
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 title claims abstract description 21
- 239000002000 Electrolyte additive Substances 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims description 17
- 239000003792 electrolyte Substances 0.000 claims abstract description 16
- 239000011255 nonaqueous electrolyte Substances 0.000 claims abstract description 12
- 229910003002 lithium salt Inorganic materials 0.000 claims abstract description 8
- 159000000002 lithium salts Chemical class 0.000 claims abstract description 8
- 239000003125 aqueous solvent Substances 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 14
- 239000002994 raw material Substances 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 11
- 230000002829 reductive effect Effects 0.000 claims description 10
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 8
- 239000008151 electrolyte solution Substances 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 7
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 7
- 235000010265 sodium sulphite Nutrition 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-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
- 239000011261 inert gas Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 claims description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 2
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-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
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 2
- SBLRHMKNNHXPHG-UHFFFAOYSA-N 4-fluoro-1,3-dioxolan-2-one Chemical compound FC1COC(=O)O1 SBLRHMKNNHXPHG-UHFFFAOYSA-N 0.000 claims description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 2
- JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910013188 LiBOB Inorganic materials 0.000 claims description 2
- 229910010941 LiFSI Inorganic materials 0.000 claims description 2
- 229910001290 LiPF6 Inorganic materials 0.000 claims description 2
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 claims description 2
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 claims description 2
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 claims description 2
- 239000012043 crude product Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229940117389 dichlorobenzene Drugs 0.000 claims description 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 2
- CYEDOLFRAIXARV-UHFFFAOYSA-N ethyl propyl carbonate Chemical compound CCCOC(=O)OCC CYEDOLFRAIXARV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910003473 lithium bis(trifluoromethanesulfonyl)imide Inorganic materials 0.000 claims description 2
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 claims description 2
- 229910001486 lithium perchlorate Inorganic materials 0.000 claims description 2
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 claims description 2
- VDVLPSWVDYJFRW-UHFFFAOYSA-N lithium;bis(fluorosulfonyl)azanide Chemical compound [Li+].FS(=O)(=O)[N-]S(F)(=O)=O VDVLPSWVDYJFRW-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- WCMAGBUGKRNIPT-UHFFFAOYSA-N methyl prop-1-ynyl carbonate Chemical compound COC(=O)OC#CC WCMAGBUGKRNIPT-UHFFFAOYSA-N 0.000 claims description 2
- 229940017219 methyl propionate Drugs 0.000 claims description 2
- KKQAVHGECIBFRQ-UHFFFAOYSA-N methyl propyl carbonate Chemical compound CCCOC(=O)OC KKQAVHGECIBFRQ-UHFFFAOYSA-N 0.000 claims description 2
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 abstract description 29
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract description 28
- 239000000654 additive Substances 0.000 abstract description 11
- 238000003860 storage Methods 0.000 abstract description 11
- 230000000996 additive effect Effects 0.000 abstract description 9
- 238000000354 decomposition reaction Methods 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 230000009467 reduction Effects 0.000 abstract description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 5
- 239000007773 negative electrode material Substances 0.000 description 5
- 238000013112 stability test Methods 0.000 description 5
- 229910032387 LiCoO2 Inorganic materials 0.000 description 4
- 239000002033 PVDF binder Substances 0.000 description 4
- 229910021383 artificial graphite Inorganic materials 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003575 carbonaceous material Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 230000001351 cycling effect Effects 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000007774 positive electrode material Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- -1 cyclic sulfonic acid esters Chemical class 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 238000003487 electrochemical reaction Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910021382 natural graphite Inorganic materials 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 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
- 229910000733 Li alloy Inorganic materials 0.000 description 1
- 229910012820 LiCoO Inorganic materials 0.000 description 1
- 229910052493 LiFePO4 Inorganic materials 0.000 description 1
- 229910003005 LiNiO2 Inorganic materials 0.000 description 1
- 229910002097 Lithium manganese(III,IV) oxide Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
Classifications
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- 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
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- H—ELECTRICITY
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- 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
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- 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
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- 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
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- 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
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- H01M2300/0025—Organic electrolyte
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Abstract
本发明公开了一种环状磺酸酯类锂离子电池电解液添加剂,具有如式Ⅰ所示的结构:
Description
技术领域
本发明涉及锂电池领域,尤其涉及一种环状磺酸酯类锂离子电池电解液添加剂、其制备方法与应用。
背景技术
锂离子电池主要由正极、非水系电解液和负极构成。作为构成锂离子电池的负极,已知有例如金属锂、能吸收和释放锂的金属化合物(例如金属单体、氧化物、与锂的合金等)以及碳材料等,特别是使用了能吸收/释放锂的人造石墨、天然石墨等碳材料的锂离子电池得以广泛应用。目前,对于将天然石墨、人造石墨等高结晶化的碳材料作为负极材料使用的锂离子电池,在充电时非水系电解液中的非水系溶剂在负极表面被还原分解,因而由此产生的分解物、气体会阻碍电池原本的电化学反应,从而使循环特性降低。
另外,对于将锂金属、及其合金、硅、锡等金属单体、氧化物等作为负极材料使用的锂离子电池,虽然初始容量高但在循环中负极材料的微粉化加剧,因此与碳材料的负极相比,容易发生非水系溶剂的还原分解,由此导致伴随电池的容量、循环特性之类的电池性能大幅降低。
针对正极,已知的有LiCoO2、LiMn2O4、LiNiO2、LiFePO4等,使用了这些的锂离子电池在充电状态下变为高温时,在正极材料与非水系电解液的界面非水系电解液中的非水系溶剂会局部地部分氧化分解,因而由此产生的分解物、气体会阻碍电池原本的电化学反应,导致电池循环特性等性能下降。
为了克服这些正负极的局部分解及提高以长期耐久性、输出特性为代表的电池性能,对于离子传导性高、且电子传导性低、长期形成稳定的SEI而言是重要的,目前一般通过在电解液中加入少量环状磺酸酯类的添加剂,如DTD、PST、PS等添加剂,来促进SEI膜的形成,由此达到抑制在负极上的溶剂的分解反应,抑制高温贮藏时的电池的容量降低,抑制气体产生,以及抑制电池负荷特性的劣化。
发明内容
本发明针对上述问题,提供一种环状磺酸酯类锂离子电池电解液添加剂,具有如式Ⅰ所示的结构:
式中,R1和R2独立地选自氢原子、氟原子、苯基、含氟原子或氰基的苯基、碳原子数1-6的直连或非直连烷基、含氟原子的碳原子数1-6的烷烃基中的一种;n为1或2。
上述通式对应的一系列的添加剂可由以下方法统一制得:
1)在惰性气体的保护下以及在20-110℃的温度条件下,将原料1、亚硫酸钠和亚硫酸氢钠混合物均匀的分散在溶剂中,反应时间1-24h,减压脱溶剂至无馏分,浓盐酸酸化获得中间体1粗品;
所述原料1和中间体1的结构如下:
所述亚硫酸钠用量为原料1摩尔数的0.2-0.8倍,优选0.3-0.5倍;所述亚硫酸氢钠用量为原料1摩尔数的1.8-2.4倍。
所述溶剂选自水、甲醇、乙醇、乙腈或THF中的一种或多种的组合;
2)在惰性气体的保护下,向所得中间体1中加入有机溶剂,于80-180℃回流分水,至无水分分出,减压脱溶剂至无馏分,并于10-3000Pa,100-230℃加热反应时间1-20h,即得环状磺酸酯类锂离子电池电解液添加剂;所述有机溶剂选自氯苯、二氯苯或硝基苯中的一种或多种的组合。
具体地,本发明环状磺酸酯类锂离子电池电解液添加剂具有如式S01-S27所示的具体结构:
本发明环状磺酸酯类锂离子电池电解液添加剂作为一种锂电池用非水电解液的添加剂,其须与非水溶剂和电解质锂盐配合形成锂电池用非水电解液,本发明在电解液中的重量占比为0.01-10%,电解质锂盐在电解液中的重量占比为10-20%。
作为可选,非水溶剂自碳酸亚乙酯、碳酸亚丙酯、碳酸亚丁酯、氟代碳酸亚乙酯、碳酸二甲酯、碳酸二乙酯、碳酸二丙酯、碳酸甲乙酯、碳酸二丙酯、碳酸甲丙酯、碳酸乙丙酯、碳酸甲丙炔酯、1,4-丁内酯、丙酸甲酯、丁酸甲酯、乙酸乙酯、丙酸乙酯、丙酸丙酯或丁酸乙酯中的一种或多种的组合;电解质锂盐的用量为所述锂离子电池非水电解液总量的10-20wt%,选自LiPF6、LiClO4、LiBF4、LiBOB、LiODFB、LiTDI、LiTFSI或LiFSI中的一种或多种的组合。
本发明添加剂形成的非水电解液可用在常见锂离子电池中,和隔膜设置在锂电池的负极和正极之间即可。本发明环状磺酸酯类锂离子电池电解液添加剂应用于锂电池,可有效地抑制了高温循环和高温存储时电池容量的降低,同时可抑制电解液分解产气。
具体实施方式
以下结合实例对本发明进行描述,所举实例只用于解释本发明,并非用于限定本发明的范围。
一、环状磺酸酯的合成
1、S01的合成
(1)中间体1的制备
原料1可以商业采购或专利CN102249861的制备方法制备;
将123g原料1、50.4g亚硫酸钠和140.05g亚硫酸氢钠加入到2L三口烧瓶中,加入550g去离子水和150g乙醇,剧烈搅拌,升温至体系回流,反应时间18h,减压脱溶剂至无馏分,黑色残余物使用乙醇溶剂,通入氯化氢气体酸化,析出大量NaCl固体,过滤滤除不溶物,所得滤液进一步脱溶剂至无馏分,获得153g中间体1,含部分溶剂,备用;
(2)S01的制备
向上述所得中间体1中加入氯苯,升温至132℃回流,并采用分水器分水,待无明显水珠分离后,改用减压蒸馏装置脱出溶剂至无馏分,进一步50~100Pa,130℃加热反应时间3.0h,得到黑色粘稠固体;降温至20~30℃,向上述反应体系中加入碳酸二甲酯溶解,加入白露A活性,于50~60℃脱色搅拌30min,降至室温过滤,滤液脱溶剂,采用碳酸二甲酯+正庚烷重结晶得到S01白色固体37.1g,收率34.97%。
GC-MS:211,1H NMR(400MHz):溶剂氘代氯仿,δ(ppm):4.322ppm(S,1H)。
2、S15的制备
(1)中间体1的制备
将55.0g原料1、10.1g亚硫酸钠和28.0g亚硫酸氢钠加入到500mL三口烧瓶中,加入100g去离子水和30g乙醇,剧烈搅拌,升温至体系回流,反应时间24h,减压脱溶剂至无馏分,黑色残余物使用乙醇溶剂,通入氯化氢气体酸化,析出大量NaCl固体,过滤滤除不溶物,所得滤液进一步脱溶剂至无馏分,获得62g中间体1,含部分溶剂,备用;
(2)S15的制备
向上述所得中间体1中加入邻二氯苯,升温至150℃回流,并采用分水器分水,待无明显水珠分离后,改用减压蒸馏装置脱出溶剂至无馏分,进一步50~100Pa,160℃加热反应时间5.0h,得到黑色粘稠固体;降温至20~30℃,向上述反应体系中加入碳酸二甲酯溶解,加入白露A活性,于50~60℃脱色搅拌30min,降至室温过滤,滤液脱溶剂,采用碳酸二甲酯+正庚烷重结晶得到S15白色固体14.8g,收率28.68%。
GC-MS:516,1H NMR(400MHz):溶剂氘代氯仿,δ(ppm):7.352~7.303ppm(m,5H)。
3、S24的制备
(1)中间体1的制备
将54.8g原料1、20.3g亚硫酸钠和56.0g亚硫酸氢钠加入到500mL三口烧瓶中,加入250g去离子水和50g乙醇,剧烈搅拌,升温至体系回流,反应时间14h,减压脱溶剂至无馏分,黑色残余物使用乙醇溶剂,通入氯化氢气体酸化,析出大量NaCl固体,过滤滤除不溶物,所得滤液进一步脱溶剂至无馏分,获得61g中间体1,含部分溶剂,备用;
(2)S24的制备
向上述所得中间体1中加入氯苯,升温至132℃回流,并采用分水器分水,待无明显水珠分离后,改用减压蒸馏装置脱出溶剂至无馏分,进一步50~100Pa,130℃加热反应时间8.0h,得到黑色粘稠固体;降温至20~30℃,向上述反应体系中加入碳酸二甲酯溶解,加入白露A活性,于50~60℃脱色搅拌30min,降至室温过滤,滤液脱溶剂,采用碳酸二甲酯+正庚烷重结晶得到S24白色固体12.1g,收率25.20%。
GC-MS:240,1H NMR(400MHz):溶剂氘代氯仿,δ(ppm):3.603~3.582ppm(t,2H),2.219~2.198ppm(t,2H)。
二、非水电解液及锂电池
将制备的化合物用作实施例1-12锂离子电池非水电解液,对应锂电池配比如表1所示。
表1.电解液配方及锂电池配比
实施例1-12和对比例1-6锂电池的制备方法:
(1)正极片制备
以LiCoO2正极材料为例:将正极LiCoO2粉末、炭黑(粒度为1000nm)、聚偏二氟乙烯(PVDF)和N,N-二甲基吡咯烷酮(NMP)混合制成均一的浆料,将浆料均匀涂敷在铝箔(15μm)集流体上,进行干燥,轧制,得到LiCoO2正极材料;于120℃下烘12h,干燥后的极片中,LiCoO2占总涂敷物的94%,粘结剂占4%,炭黑占2%,将所得极片裁剪成直径为8mm圆片作为正极,其它正极材料按同样的方法制备;
(2)负极片制备
以人造石墨负极材料为例:将人造石墨,聚偏二氟乙烯(PVDF)和N-甲基吡咯烷酮(NMP)混合制成均一的浆料,将浆料均匀涂敷在铜箔(15μm)集流体上,进行干燥,轧制,得到碳负极材料,于120℃下烘12h,干燥后的极片中,石墨占总涂敷物的96.4%,粘结剂占3.6%,将所得极片裁剪成直径为8mm圆片作为负极;
(3)电解液制备
在含水量<1ppm的氩气气氛手套箱中,将锂盐溶解于溶剂中,再加入新型环状磺酸酯添加剂,混合均匀后获得电解液;
(4)锂离子电池的制备
以上述步骤(1)和(2)所述的材料作为工作电极,Celgard 2400膜(天津)为隔膜,组装CR2430型扣式电池,组装顺序按负极到正极依次为:负极壳,弹片,垫片,负极片,电解液,隔膜,正极片,正极壳,由封口机密封,此操作均在纯氩气手套箱完成。
三、锂电池性能检测
测试1、高温循环性能测试
将制备得到的电池均分别进行下述测试:
①在45℃下,将电池在0.1C倍率下恒流充电至4.3V,再用相应倍率恒流放电至2.7V,此时为首次循环;
②首次循环完成后,以1.0C倍率下恒流充电至4.3V,再用相应倍率恒流放电至2.7V,按照此循环条件分别进行50次、100次、500次循环测试,分别计算得出电池循环50次、100次、500次循环后的容量保持率,其中,循环后的容量保持率按照下式进行计算:
循环后的容量保持率=(对应循环次数后的放电容量/首次循环的放电容量)×100%。
测试数据见表2。
表2.锂电池循环性能检测结果
由表2对不同电池的数据发现,使用本发明提供的添加剂做成的锂电池在45℃下,其循环稳定性,且容量保持率远高于未添加添加剂的对比例1锂电池,即使相较于对比例2-5锂电池使用以商业化的添加剂,其500周循环的电池容量保持率也表现出明显优势,特别是当碳酸甲丙炔酯存在时。
测试2、热稳性测试
将实施例1-12和对比例1-6制备得到的电池经过100次循环后,进行循环后的热稳性测试:
在25℃条件下,以0.5C电流恒流充电至4.3V,再以4.3V恒压充电至电流为0.025C,使其处于4.3V满充状态,然后将电池放在65℃的高温炉中存储15天,同时测试电池在高温炉中电压降以及测试后电池的体积变化,测试数据见表3。
其中,锂离子电池高温存储后的电压降变化率(%)=(锂离子电池高温存储前的电压-锂离子电池高温存储后的电压)/锂离子电池高温存储前的电压×100%;
锂离子电池高温存储后的体积变化率(%)=(锂离子电池高温存储后的体积-锂离子电池高温存储前的体积)/锂离子电池高温存储前的体积×100%。
表3.锂电池热稳性测试结果
从表3可见,与对比例1-6锂电池进行100次循环后经过热稳性测试所呈现的状态相比,锂电池1-12进行100次循环再经过高温下的热稳定测试后,电池电压降变化率仅为11-15%,远低于对比例1-6锂电池的电压降变化率。
另外,对于体积变化率同样存在较大差异,对比例1-6锂电池体积膨胀变大较为明显,而锂电池1-12多次循环后,高温储存体积变化率仅为4-7%,远小于对比例1-6锂电池的体积变化率。由此可以得知,本发明制备的新型环状磺酸酯类添加剂应用到锂离子电池中后,能够大幅提高多次循环后的锂离子电池的热稳定性,抑制电解液分解产气,具有良好的应用前景。
以上所述仅为本发明的较佳实施例,并不用以限制本发明,凡在本发明的精神和原则之内,所作的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (8)
3.一种权利要求1所述的环状磺酸酯类锂离子电池电解液添加剂的制备方法,其特征在于,包括以下步骤:
1)在惰性气体的保护下以及在20-110℃的温度条件下,将原料1、亚硫酸钠和亚硫酸氢钠混合物均匀的分散在溶剂中,反应时间1-24h,减压脱溶剂至无馏分,浓盐酸酸化获得中间体1粗品;
所述原料1和中间体1的结构如下:
所述溶剂选自水、甲醇、乙醇、乙腈或THF中的一种或多种的组合;
2)在惰性气体的保护下,向所得中间体1中加入有机溶剂,于80-180℃回流分水,至无水分分出,减压脱溶剂至无馏分,并于10-3000Pa,100-230℃加热反应时间1-20h,即得环状磺酸酯类锂离子电池电解液添加剂;
所述有机溶剂选自氯苯、二氯苯或硝基苯中的一种或多种的组合。
4.根据权利要求3所述的方法,其特征在于,所述亚硫酸钠用量为原料1摩尔数的0.2-0.8倍;所述亚硫酸氢钠用量为原料1摩尔数的1.8-2.4倍。
5.一种锂离子电池非水电解液,其特征在于,包括非水溶剂、电解质锂盐和权利要1或2所述的环状磺酸酯类锂离子电池电解液添加剂或权利要求3或4所述方法制备的环状磺酸酯类锂离子电池电解液添加剂,所述环状磺酸酯类锂离子电池电解液添加剂的用量为所述锂离子电池非水电解液总量的0.01-10wt%。
6.根据权利要求5所述的锂离子电池非水电解液,其特征在于,所述非水溶剂自碳酸亚乙酯、碳酸亚丙酯、碳酸亚丁酯、氟代碳酸亚乙酯、碳酸二甲酯、碳酸二乙酯、碳酸二丙酯、碳酸甲乙酯、碳酸二丙酯、碳酸甲丙酯、碳酸乙丙酯、碳酸甲丙炔酯、1,4-丁内酯、丙酸甲酯、丁酸甲酯、乙酸乙酯、丙酸乙酯、丙酸丙酯或丁酸乙酯中的一种或多种的组合。
7.根据权利要求5所述的锂离子电池非水电解液,其特征在于,所述电解质锂盐的用量为所述锂离子电池非水电解液总量的10-20wt%,选自LiPF6、LiClO4、LiBF4、LiBOB、LiODFB、LiTDI、LiTFSI或LiFSI中的一种或多种的组合。
8.一种锂离子电池,包括负极和正极,以及设置在所述负极和正极之间的隔膜和电解液,其特征在于,所述电解液为权利要求5-7任一项所述的锂离子电池非水电解液。
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JP2023543317A (ja) | 2023-10-13 |
JP7408013B2 (ja) | 2024-01-04 |
KR20230051295A (ko) | 2023-04-17 |
KR102622802B1 (ko) | 2024-01-08 |
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