CN116547850A - Composition and method for producing the same - Google Patents
Composition and method for producing the same Download PDFInfo
- Publication number
- CN116547850A CN116547850A CN202180083085.2A CN202180083085A CN116547850A CN 116547850 A CN116547850 A CN 116547850A CN 202180083085 A CN202180083085 A CN 202180083085A CN 116547850 A CN116547850 A CN 116547850A
- Authority
- CN
- China
- Prior art keywords
- group
- lithium
- battery
- formulation
- formula
- 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
- 239000000203 mixture Substances 0.000 title claims description 68
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000003792 electrolyte Substances 0.000 claims abstract description 63
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 238000009472 formulation Methods 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 45
- 229910052751 metal Inorganic materials 0.000 claims description 29
- 239000002184 metal Substances 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 21
- -1 lithium hexafluorophosphate Chemical compound 0.000 claims description 19
- 239000011255 nonaqueous electrolyte Substances 0.000 claims description 18
- 229910052744 lithium Inorganic materials 0.000 claims description 13
- SBLRHMKNNHXPHG-UHFFFAOYSA-N 4-fluoro-1,3-dioxolan-2-one Chemical compound FC1COC(=O)O1 SBLRHMKNNHXPHG-UHFFFAOYSA-N 0.000 claims description 12
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 12
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 12
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 11
- 239000011133 lead Substances 0.000 claims description 8
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 claims description 8
- 229910001486 lithium perchlorate Inorganic materials 0.000 claims description 8
- 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 8
- 239000011777 magnesium Substances 0.000 claims description 8
- 229910003002 lithium salt Inorganic materials 0.000 claims description 7
- 159000000002 lithium salts Chemical group 0.000 claims description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 6
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 6
- 229910003473 lithium bis(trifluoromethanesulfonyl)imide Inorganic materials 0.000 claims description 6
- 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 6
- 229910052749 magnesium Inorganic materials 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 229910021645 metal ion Inorganic materials 0.000 claims description 5
- 229910015013 LiAsF Inorganic materials 0.000 claims description 4
- 229910013075 LiBF Inorganic materials 0.000 claims description 4
- 229910013872 LiPF Inorganic materials 0.000 claims description 4
- 101150058243 Lipf gene Proteins 0.000 claims description 4
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 claims description 4
- MCVFFRWZNYZUIJ-UHFFFAOYSA-M lithium;trifluoromethanesulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)F MCVFFRWZNYZUIJ-UHFFFAOYSA-M 0.000 claims description 4
- 150000002815 nickel Chemical class 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 238000009420 retrofitting Methods 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 230000001502 supplementing effect Effects 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims 16
- 125000000304 alkynyl group Chemical group 0.000 claims 16
- 159000000007 calcium salts Chemical class 0.000 claims 2
- 159000000003 magnesium salts Chemical class 0.000 claims 2
- 159000000000 sodium salts Chemical class 0.000 claims 2
- 150000003751 zinc Chemical class 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 12
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical group [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 11
- 229910001416 lithium ion Inorganic materials 0.000 description 11
- 239000007774 positive electrode material Substances 0.000 description 11
- 239000000654 additive Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 229910052723 transition metal Inorganic materials 0.000 description 9
- 229910013870 LiPF 6 Inorganic materials 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 239000011572 manganese Substances 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 229910010743 LiFeSi Inorganic materials 0.000 description 4
- 229910013716 LiNi Inorganic materials 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 239000003575 carbonaceous material Substances 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- 239000006258 conductive agent Substances 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000011888 foil Substances 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 239000006183 anode active material Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000007769 metal material Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 229910000314 transition metal oxide Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical group 0.000 description 3
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 229910010941 LiFSI Inorganic materials 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 239000002033 PVDF binder Substances 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229920002313 fluoropolymer Polymers 0.000 description 2
- 239000004811 fluoropolymer Substances 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000002687 intercalation Effects 0.000 description 2
- 238000009830 intercalation Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 229910052706 scandium Inorganic materials 0.000 description 2
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 229910021561 transition metal fluoride Inorganic materials 0.000 description 2
- 229910052727 yttrium Inorganic materials 0.000 description 2
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 2
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-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
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 229910000733 Li alloy Inorganic materials 0.000 description 1
- 229910012851 LiCoO 2 Inorganic materials 0.000 description 1
- 229910015643 LiMn 2 O 4 Inorganic materials 0.000 description 1
- 229910014689 LiMnO Inorganic materials 0.000 description 1
- 229910013290 LiNiO 2 Inorganic materials 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 229910000676 Si alloy Inorganic materials 0.000 description 1
- 229910001128 Sn alloy Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- 239000006230 acetylene black Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 229910021383 artificial graphite Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000009831 deintercalation Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004146 energy storage Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 229910021389 graphene Inorganic materials 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000010220 ion permeability Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003273 ketjen black Substances 0.000 description 1
- 150000002641 lithium Chemical class 0.000 description 1
- 239000001989 lithium alloy Substances 0.000 description 1
- 239000011855 lithium-based material Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000003446 memory effect Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002070 nanowire Substances 0.000 description 1
- 229910021382 natural graphite Inorganic materials 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 150000005677 organic carbonates Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
-
- 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
- Secondary Cells (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides an application of a compound of formula 1 in a nonaqueous battery electrolyte preparationWherein R is a fluorinated alkyl group and X is selected from the group consisting of: F. c1 and H, CF 3 And C which can be fluorinated at least partially 1 To C 6 Alkyl, and the-OR group may be cis OR trans relative to any other group X.
Description
The present disclosure relates to nonaqueous electrolytes for energy storage devices (including batteries and capacitors), particularly for secondary batteries and devices known as supercapacitors.
There are two main types of batteries: primary and secondary batteries. Primary batteries are also known as non-rechargeable batteries. Secondary batteries are also called rechargeable batteries. One well known type of rechargeable battery is a lithium ion battery. The lithium ion battery has high energy density, no memory effect and low self-discharge.
Lithium ion batteries are commonly used in portable electronic devices and electric vehicles. In a battery, lithium ions move from the negative electrode to the positive electrode during discharge and return when charged.
Typically, the electrolyte includes a non-aqueous solvent and an electrolyte salt plus additives. The electrolyte is typically a mixture of organic carbonates such as ethylene carbonate, propylene carbonate, fluoroethylene carbonate and dialkyl carbonate containing lithium ion electrolyte salts. Many lithium salts can be used as the electrolyte salt, and common examples include lithium hexafluorophosphate (LiPF 6 ) Lithium bis (fluorosulfonyl) imide, "LiFSI" and lithium bis (trifluoromethanesulfonyl) imide (LiTFSI).
The electrolyte must perform many individual functions within the cell.
The primary function of the electrolyte is to facilitate the flow of charge between the cathode and anode. Which occurs by the transport of metal ions within the cell from and or to one or both of the anode and cathode, whereby upon chemical reduction or oxidation, charge is released/absorbed.
Thus, the electrolyte needs to provide a medium capable of solvating and/or supporting metal ions.
The electrolyte is typically non-aqueous due to the use of lithium electrolyte salts and the exchange of lithium ions with lithium metal (very reactive with water) and the sensitivity of other battery components to water.
In addition, the electrolyte must have suitable rheological properties to allow/enhance the flow of ions therein at typical operating temperatures at which the cell is exposed and expected to operate.
In addition, the electrolyte must be as chemically inert as possible. This is particularly important in the context of life expectancy of the battery, which relates to in-cell corrosion (e.g., of the electrodes and the housing) and battery leakage problems. Also important in view of chemical stability is flammability. Unfortunately, typical electrolyte solvents can present a safety hazard because they often contain flammable substances.
This can be problematic because, in operation, the battery can accumulate heat when discharged or discharged. This is especially true for high density batteries such as lithium ion batteries. Thus, it is desirable that the electrolyte exhibit low flammability and other related characteristics (such as high flash point).
It is also desirable that the electrolyte be free of environmental issues regarding disposability after use or other environmental issues (such as global increase Wen Qianneng values).
It is an object of the present invention to provide a non-aqueous electrolyte that provides improved performance due to the non-aqueous electrolytes of the prior art.
Aspects of use
According to a first aspect of the present invention there is provided the use of a compound of formula 1 in a non-aqueous battery electrolyte formulation. Preferably, the composition comprising the compound of formula 1 is used in a lithium ion battery.
According to a second aspect of the present invention there is provided the use in a battery of a non-aqueous battery electrolyte formulation comprising a compound of formula 1.
Composition/device aspects
According to a third aspect of the present invention there is provided a battery electrolyte formulation comprising a compound of formula 1.
According to a fourth aspect of the present invention there is provided a formulation comprising a metal ion and a compound of formula 1, optionally in combination with a solvent.
According to a fifth aspect of the present invention there is provided a battery comprising a battery electrolyte formulation comprising a compound of formula 1.
Method aspect
According to a sixth aspect of the present invention there is provided a method of reducing the flash point of a battery and/or battery electrolyte formulation, the method comprising adding a formulation comprising a compound of formula 1.
According to a seventh aspect of the present invention there is provided a method of powering an article, the method comprising using a battery comprising a battery electrolyte formulation comprising a compound of formula 1.
According to an eighth aspect of the present invention, there is provided a method of retrofitting a battery electrolyte formulation, the method comprising: (a) At least partially replacing the battery electrolyte with a battery electrolyte formulation comprising a compound of formula 1; and/or (b) supplementing the battery electrolyte with a battery electrolyte formulation comprising the compound of formula 1.
According to a ninth aspect of the present invention there is provided a process for the preparation of a compound of formula 1 by reacting a compound of formula 2a and/or 2b
With an alcohol ROH in the presence of a strong base, optionally in the presence of a solvent, under suitable temperature and pressure conditions. Conveniently, the solvent is a polar aprotic solvent; preferably, it may be selected from N-methyl-2-pyrrolidone, acetonitrile, N-dimethylformamide, hexamethylphosphoramide, tetrahydrofuran or dimethylsulfoxide. Conveniently, the strong base is an anhydrous or substantially anhydrous alkali metal hydroxide, alkoxide or hydride. Conveniently, the reaction is carried out at a temperature of from 0 ℃ to 300 ℃. Conveniently, the reaction is carried out at a pressure of from 0bar to 100 bar.
In formula 2a, X is halogen or-CF 3 Provided that at least one X is H. Most preferably, at least one X is halogen and at least one X is H, and wherein when at least one X is halogen and one X is hydrogen, the groups are trans relative to each other.
In formula 2b, X is hydrogen or-CF 3 。
According to a tenth aspect of the present invention, there is provided a method of preparing a battery electrolyte formulation, the method comprising mixing a compound comprising formula 1 with a lithium-containing compound.
According to an eleventh aspect of the present invention, there is provided a method of improving battery capacity/charge transfer within a battery/battery life, etc. by using the compound of formula 1.
Compounds of formula 1
With respect to all aspects of the present invention, preferred embodiments of formula (1) are as follows
Wherein the method comprises the steps of
R is a fluorinated alkyl group and the stereochemistry of the-OR group may be cis OR trans with respect to any other functional group and X is selected from the group consisting of: F. cl, H, CF 3 And C which can be fluorinated at least partially 1 To C 6 An alkyl group.
Alternatively, and also with respect to all aspects of the invention, alternative embodiments of formula (1) are as follows
Wherein the method comprises the steps of
R 1 Selected from the group consisting of: F. cl, H, CF 3 C which can be fluorinated at least partially 1 To C 6 An alkyl group;
R 2 selected from the group consisting of: F. cl, H, CF 3 C which can be fluorinated at least partially 1 To C 6 An alkyl group;
R 3 selected from the group consisting of: F. cl, H, CF 3 C which can be fluorinated at least partially 1 To C 6 An alkyl group;
R 4 selected from the group consisting of: c (C) 1 To C 12 Alkyl, which may be at least partially fluorinated;
wherein R is 1 To R 4 At least one of is OR comprises F and-OR 4 The stereochemistry of the groups may be cis or trans to any other functional group.
It should be noted that the ninth aspect of the present invention should be considered as being applicable to both embodiments of formula (1).
Advantages are that
In various aspects of the invention, electrolyte formulations have been found to have unexpected advantages.
The advantages of using the compound of formula 1 in an electrolyte solvent composition are manifested in a number of ways. Their presence may reduce the flammability of the electrolyte composition (such as when measured, for example, by flash point). Their oxidative stability makes them useful for batteries that need to operate under harsh conditions, they are compatible with common electrode chemistries, and can even improve the performance of these electrodes by interacting with them.
In addition, it has been found that electrolyte compositions comprising compounds of formula 1 have excellent physical properties, including low viscosity and low melting point, as well as high boiling point and associated advantages of little or no gas generation in use. It has been found that the electrolyte formulation wets and spreads very well on surfaces, especially fluorine-containing surfaces; it is inferred that this is due to the beneficial relationship between adhesion and cohesion, resulting in lower contact angles.
Furthermore, it has been found that electrolyte compositions comprising compounds of formula 1 have excellent electrochemical properties, including improved capacity retention, improved cycle characteristics and capacity, improved compatibility with other battery components (e.g., separator and current collector), and with all types of cathode and anode chemistries, including systems that operate over a range of voltages and especially at high voltages and include additives such as silicon. In addition, the electrolyte formulation exhibits good solvation of metal (e.g., lithium) salts and interaction with any electrolyte solvents present.
Preferred features relating to the various aspects of the invention are as follows.
Preferred compounds
Preferred examples of the Compounds of the first embodiment of formula 1
The method comprises the following steps: -
R is CH 2 CF 3 、CH 2 CF 2 CF 2 CHF 2 Or CH (CF) 3 ) 2 The method comprises the steps of carrying out a first treatment on the surface of the And is also provided with
X is H.
Preferred features of alternative embodiments of the compound of formula 1
As described in the following numbered paragraphs.
The compound of paragraph 1-formula 1 wherein preferably R 1 To R 4 At least two or three of (a) are or contain F; for example R 1 To R 3 One or both of which are or contain F, and R 4 Containing F.
Paragraph 2-the compound of paragraph 1 wherein preferably R 1 To R 4 Comprises unfluorinated or at least partially fluorinated C 1 To C 6 An alkyl group.
Paragraph 3-the compound of paragraph 1 or 2 wherein preferably R 2 Selected from the group consisting of: H. CF (compact flash) 3 And C which can be fluorinated at least partially 1 To C 6 An alkyl group.
Paragraph 4-the compounds according to paragraphs 1 to 3, wherein preferably R 2 Selected from H and CF 3 A group of groups.
Paragraph 5-the process according to paragraphs 1 to 4A compound, wherein preferably R 2 Is CF (CF) 3 。
Paragraph 6-the compound of paragraphs 1 to 5 wherein preferably R 4 For C which can be fluorinated at least partially 1 To C 6 An alkyl group;
paragraph 7-Compounds according to paragraphs 1 to 6, wherein R is preferred 4 Is at least partially fluorinated C 1 To C 4 An alkyl group;
paragraph 8-the compound of paragraphs 1 to 7 wherein preferably R 4 Selected from the group consisting of: ethyl, n-propyl, isopropyl, n-butyl, isobutyl and at least partially fluorinated derivatives thereof.
Paragraph 9-the compound of paragraphs 1 to 8 wherein preferably R 4 Selected from the group consisting of: CH (CH) 2 CF 3 、CH 2 CH 2 CF 3 、CH 2 CHFCF 3 、CH 2 CF 2 CF 2 CHF 2 And CH (CF) 3 ) 2 。
Paragraph 10-the compound of paragraphs 1 to 9 wherein preferably R 1 And R is 3 Independently selected from the group consisting of: H. CF (compact flash) 3 And C which can be fluorinated at least partially 1 To C 6 An alkyl group.
Paragraph 11-the compound of paragraphs 1 to 10 wherein preferably R 1 And R is 3 Independently selected from the group consisting of: H. CF (compact flash) 3 、CH 2 CF 3 、CH 2 CH 2 CF 3 、CH 2 CHFCF 3 、CH 2 CF 2 CF 2 CHF 2 And CH (CF) 3 ) 2 。
Paragraph 12-the compound of paragraphs 1 to 11 wherein preferably R 1 And R is 3 Independently selected from H and CF 3 A group of groups.
Paragraph 13-the compound of paragraphs 1 to 12 wherein preferably R 1 And R is 3 H.
Preferred examples of compounds of alternative embodiments of the compound of formula 1 are those wherein: -
R 1 In the presence of a hydrogen atom, which is H,
R 2 is CF (CF) 3 ，
R 3 Is H, and
R 4 is CH 2 CF 3 、CH 2 CF 2 CF 2 CHF 2 Or CH (CF) 3 ) 2 。
Electrolyte formulation
Preferably, the electrolyte formulation comprises 0.1wt% to 99.9wt% of the compound of formula 1. Optionally, the compound of formula 1 (in the electrolyte formulation) is present in an amount of more than 1wt%, optionally more than 5wt%, optionally more than 10wt%, optionally more than 15wt%, optionally more than 20wt% and optionally more than 25 wt%. Optionally, the compound of formula 1 (in the electrolyte formulation) is present in an amount of less than 1wt%, optionally less than 5wt%, optionally less than 10wt%, optionally less than 15wt%, optionally less than 20wt% and optionally less than 25 wt%.
Metal salts
The nonaqueous electrolyte solution further contains a metal electrolyte salt, and is generally present in an amount of 0.1wt% to 20wt% with respect to the total mass of the nonaqueous electrolyte formulation.
The metal salts generally include lithium, sodium, magnesium, calcium, lead, zinc or nickel salts.
Preferably, the metal salt comprises a lithium salt, such as those selected from the group comprising: lithium hexafluorophosphate (LiPF) 6 ) Lithium hexafluoroarsenate monohydrate (LiAsF) 6 ) Lithium perchlorate (LiClO) 4 ) Lithium tetrafluoroborate (LiBF) 4 ) Lithium trifluoromethane sulfonate (LiS 0) 3 CF 3 ) Lithium bis (fluorosulfonyl) imide (Li (FSO) 2 ) 2 N) and lithium bis (trifluoromethanesulfonyl) imide (Li (CF) 3 SO 2 ) 2 N)。
Most preferably, the metal salt comprises LiPF 6 . Thus, in a most preferred variant of the fourth aspect of the invention, there is provided a kit comprising LiPF 6 And a formulation of a compound of formula 1, optionally in combination with a solvent
Solvent(s)
The non-aqueous electrolyte may comprise a solvent. Preferred examples of the solvent include fluoroethylene carbonate (FEC) and/or Propylene Carbonate (PC), dimethyl carbonate (DMC), methyl ethyl carbonate (EMC) or Ethylene Carbonate (EC).
When present, the solvent comprises from 0.1wt% to 99.9wt% of the electrolyte liquid component.
Additive agent
The non-aqueous electrolyte may contain additives.
Suitable additives may be used as surface film formers which form ion permeable films on the surface of the positive or negative electrode. This makes it possible to prevent the decomposition reaction of the nonaqueous electrolyte and the electrolyte salt occurring on the electrode surface in advance, thereby preventing the decomposition reaction of the nonaqueous electrolyte on the electrode surface.
Examples of film former additives include Vinylene Carbonate (VC), ethylene Sulfite (ES), lithium bis (oxalato) borate (LiBOB), cyclohexylbenzene (CHB), and o-diphenyl benzene (OTP). These additives may be used alone, or two or more may be used in combination.
When present, the additive is present in an amount of 0.1wt% to 3wt% relative to the total mass of the nonaqueous electrolyte formulation.
Battery cell
Primary secondary battery
The battery may include a primary battery (non-rechargeable) or a secondary battery (rechargeable). Most preferably, the battery comprises a secondary battery.
A battery containing a non-aqueous electrolyte will typically include several elements. The elements constituting the preferred nonaqueous electrolyte secondary battery are as follows. It should be understood that other battery elements (such as temperature sensors) may be present; the following list of battery components is not intended to be exhaustive.
Electrode
The battery typically includes a positive electrode and a negative electrode. Typically, the electrode is porous and allows metal ions (lithium ions) to enter and exit its structure through a process called intercalation (intercalation) or deintercalation.
For rechargeable batteries (secondary batteries), the term "cathode" refers to the electrode where reduction occurs during the discharge cycle. For lithium ion batteries, the positive electrode ("cathode") is a lithium-based electrode.
Positive electrode (cathode)
The positive electrode is typically composed of a positive electrode current collector such as a metal foil, optionally with a positive electrode active material layer disposed on the positive electrode current collector.
The positive electrode current collector may be a metal foil that is stable in the range of potential applied to the positive electrode, or may be a film having a metal surface layer that is stable in the range of potential applied to the positive electrode. Aluminum (A1) is preferable as a metal that is stable in the range of potential applied to the positive electrode.
The positive electrode active material layer generally includes a positive electrode active material and other components (such as a conductive agent and a binder). This is generally obtained by the following method: the components are mixed in a solvent, and the mixture is applied to a positive electrode current collector, followed by drying and rolling.
The positive electrode active material may be a lithium (Li) -containing transition metal oxide. The transition metal element may be at least one selected from the group consisting of: scandium (Sc), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), and yttrium (Y). Among these transition metal elements, manganese, cobalt and nickel are most preferable.
Some of the transition metal atoms in the transition metal oxide may be replaced with atoms of a non-transition metal element. The non-transition element may be selected from the group consisting of: magnesium (Mg), aluminum (Al), lead (Pb), antimony (Sb), and boron (B). Among these non-transition metal elements, magnesium and aluminum are most preferable.
Preferred examples of the positive electrode active material include lithium-containing transition metal oxides such as LiCoO 2 、LiNiO 2 、LiMn 2 O 4 、LiMnO 2 、LiNi 1-y Co y O 2 (0＜y＜1)、LiNi 1-y-z Co y Mn z O 2 (0 < y+z < 1) and LiNi 1-y-z Co y Al z O 2 (0 < y+z < 1). LiNi1-y-zCo containing nickel in a proportion of not less than 50mol% relative to all transition metals y Mn z O 2 (0 < y+z < 0.5) and LiNi 1-y-z Co y Al z O 2 (0 < y+z < 0.5) is preferable from the viewpoints of cost and specific capacity. These positive electrode active materials contain a large amount of alkaline components and thus promote decomposition of the nonaqueous electrolyte, resulting in reduced durability. However, the nonaqueous electrolyte of the present disclosure is not easily decomposed even when used in combination with these positive electrode active materials.
The positive electrode active material may be a lithium (Li) -containing transition metal fluoride. The transition metal element may be at least one selected from the group consisting of: scandium (Sc), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), and yttrium (Y). Among these transition metal elements, manganese, cobalt and nickel are most preferable.
Some of the transition metal atoms in the transition metal fluoride may be replaced with atoms of non-transition metal elements. The non-transition element may be selected from the group consisting of: magnesium (Mg), aluminum (Al), lead (Pb), antimony (Sb), and boron (B). Among these non-transition metal elements, magnesium and aluminum are most preferable.
A conductive agent may be used to improve the electron conductivity of the positive electrode active material layer. Preferred examples of the conductive agent include conductive carbon materials, metal powders, and organic materials. Specific examples include carbon materials (such as acetylene black, ketjen black, graphite), metal powders (such as aluminum powder), and organic materials (such as phenylene derivatives).
A binder may be used to ensure good contact between the positive electrode active material and the conductive agent, improving adhesion of components such as the positive electrode active material with respect to the surface of the positive electrode current collector. Preferred examples of the binder include fluoropolymers and rubber polymers such as Polytetrafluoroethylene (PTFE), polyvinylidene fluoride (PVdF) ethylene-propylene-isoprene copolymer, and ethylene-propylene-butadiene copolymer. The binder may be used in combination with a thickener such as carboxymethyl cellulose (CMC) or polyethylene oxide (PEO).
Negative pole (anode)
The anode is typically composed of an anode current collector such as a metal foil, optionally with an anode active material layer disposed on the anode current collector.
The negative electrode current collector may be a metal foil. Copper (without lithium) is suitable for use as the metal. Copper is easy to process at low cost and has good electron conductivity.
Generally, the negative electrode comprises carbon (such as graphite or graphene).
Silicon-based materials may also be used for the negative electrode. The preferred form of silicon is in the form of nanowires, which are preferably present on a carrier material. The support material may comprise a metal (such as steel) or a non-metal (such as carbon).
The anode may include an active material layer. When present, the active material layer includes a negative electrode active material and other components (such as a binder). This is generally obtained by the following method: the components are mixed in a solvent, and the mixture is applied to a positive electrode current collector, followed by drying and rolling.
The anode active material is not particularly limited as long as the materials are capable of storing and releasing lithium ions. Examples of suitable anode active materials include carbon materials, metals, alloys, metal oxides, metal nitrides, lithium-intercalated carbons, and lithium-intercalated silicones. Examples of carbon materials include natural/artificial graphite and pitch-based carbon fibers. Preferred examples of the metal include lithium (Li), silicon (Si), tin (Sn), germanium (Ge), indium (In), gallium (Ga), titanium, lithium alloy, silicon alloy, and tin alloy. Examples of the lithium-based material include lithium titanate (Li 2 TiO 3 )
As with the positive electrode, the binder may be a fluoropolymer or a rubber polymer, and desirably is a rubbery polymer such as styrene-butadiene copolymer (SBR). The binder may be used in combination with a thickener.
Diaphragm
The separator is preferably present between the positive electrode and the negative electrode. The separator has insulating properties. The separator may include a porous membrane having ion permeability. Examples of the porous film include microporous films, woven fabrics, and nonwoven fabrics. Suitable materials for the separator are polyolefins such as polyethylene and polypropylene.
Shell body
The battery assembly is preferably arranged within the protective housing.
The housing may comprise any suitable material that is resilient to provide support for the battery and electrical contacts to the powered device.
In one embodiment, the housing comprises a metallic material, preferably in sheet form, which is molded into the shape of the battery. The metallic material preferably comprises a plurality of portions that can be fitted together (e.g., by a push fit) during assembly of the battery. Preferably, the housing comprises an iron/steel based material.
In another embodiment, the housing comprises a plastic material molded into the shape of a battery. The plastic material preferably comprises a plurality of parts that can be joined together (e.g., by a push fit) during assembly of the battery. Preferably, the housing comprises a polymer such as polystyrene, polyethylene, polyvinyl chloride, polyvinylidene chloride or poly (chlorotrifluoroethylene). The housing may also contain other additives for plastic materials, such as fillers or plasticizers. In this embodiment, in which the battery housing comprises primarily plastic material, a portion of the housing may additionally comprise conductive/metallic material to establish electrical contact with the device being powered by the battery.
Arrangement of
The positive electrode and the negative electrode may be wound or stacked together through a separator. They are contained in a housing together with a non-aqueous electrolyte. The positive and negative electrodes are electrically connected to the housing at separate portions thereof
Module/group
Many/multiple battery cells may constitute a battery module. In the battery module, the battery cells may be organized in series and/or in parallel. Typically, these battery cells are packaged in a mechanical structure.
The battery pack may be assembled by connecting a plurality of modules together in series or in parallel. Typically, the battery pack includes additional features such as sensors and controllers (including battery management systems and thermal management systems). The battery typically includes a housing structure to form the final battery product.
End use
The batteries of the present invention, in the form of individual batteries/cells, modules and/or groups (and electrolyte formulations used therein), are intended for use in one or more of a variety of end products.
Preferred examples of end products include portable electronic devices such as GPS navigation devices, cameras, notebook computers, tablet computers and mobile phones. Other preferred examples of end products include vehicle devices (powering propulsion systems and/or any electrical systems or devices present therein) such as electric bicycles and electric motorcycles, as well as automotive applications (including hybrid and electric vehicles).
The invention will now be described with reference to the following non-limiting examples.
Preparation example
The usage is based on Journal of Fluorine Chemistry ".179The procedure reported in p.71-76 (2015) prepares the compound designated KDC-704:
accordingly, sodium hydride (192 g 60%) was added to anhydrous dimethylformamide (2.4L). The resulting slurry was cooled, and trifluoroethanol (219 g) was added to form an alkoxide thereof. The mixture was then transferred to an autoclave and 2, 3-tetrafluoropropene (224 g) was added and the mixture was stirred overnight. Unreacted 2, 3-tetrafluoropropene was discharged and the contents were quenched with ice. Adjusting the pH of the resulting mixture to>6, followed by isolation of the product as the lower layer. The product was recovered, washed with water and then over MgSO before distillation 4 And (5) drying.
19F NMR(56MHz)：-74.44(s)，-76.02(t)。
Electrolyte composition comprising KDC-704
The following examples (all in wt%) of electrolyte compositions comprising KDC-704 were prepared:
1M LiPF 6 35EC:35PC:30KDC-704 (see FIG. 1)
1M LiPF 6 35EC:35EMC:30KDC-704 (see FIG. 2)
1M LiPF 6 30EC:30PC:10FEC:30KDC-704 (see FIG. 3)
1M LiPF 6 30EC:30EMC:10FEC:30KDC-704 (see FIG. 4)
1M LiFeSi 35EC:35PC:30KDC-704 (see FIG. 5)
1M LiFeSi 35EC:35EMC:30KDC-704 (see FIG. 6)
1M LiFeSi 30EC:30PC:10FEC:30KDC-704 (see FIG. 7)
1M LiFeSi 30EC:30EMC:10FEC:30KDC-704 (see FIG. 8)
Annotation:
ec=ethylene carbonate
PC = propylene carbonate
EMC = methyl ethyl carbonate
FEC = fluoroethylene carbonate
LiPF 6 Lithium hexafluorophosphate
LiFSI = lithium bis (fluorosulfonyl) imide
The results are shown in fig. 1 to 8. These are 19 The F NMR spectrum indicated that the resulting electrolyte composition was compatible and soluble.
Figures 9a and 9b show gas chromatography and mass spectrometry analysis of KDC-704.
Mass spectrum m/z:194 ([ M)]+)、175([M-F]+)、125([M-CF 3 ]+)、97、83([CF 3 CH 2 ]+)、69([CF3]+)、42。
FIGS. 10 and 11 show the NMR spectroscopy analysis of KDC-704.
1 H NMR(400MHz，CDCl 3 ) 5.02 (1H, d,3 jh-h=4.8 hz, H1 or H2), 4.56 (1H, qd,3 jh-f=4.0 hz,3 jh-h=2.0 hz, H1 or H2), 4.16 (2H, q,3 jh-f=7.8 hz, H3).
13 C NMR(101MHz，CDCl 3 )149.32(q，2JC-F＝36.0Hz)，122.51(q，1JC-F＝277.3Hz)，119.19(q，1JC-F＝272.7Hz)，89.73(q，3JC-F＝3.6Hz)，65.57(q，2JC-F＝37.0Hz)。
FIGS. 12 and 13 show NMR spectra analysis of the Z-isomer of KDC-704.
1 H NMR(400MHz，CDCl 3 )6.31(1H，d，3JH-H＝6.9Hz，H2)，4.85(1H，qd，3JH-F＝8.0Hz，3JH-H＝6.9Hz，H1)，4.22(2H，q，3JH-F＝8.1Hz，H3)。
13 C NMR(101MHz，CDCl 3 )151.87(q，3JC-F＝5.5Hz)，122.64(q，1JC-F＝279.3Hz)，122.51(q，1JC-F＝269.2Hz)，98.28(q，2JC-F＝35.6Hz)，70.23(q，2JC-F＝35.8Hz)。
Claims (29)
1. Use of compound of formula 1 in nonaqueous battery electrolyte preparation
Wherein the method comprises the steps of
R is selected from the group consisting of: optionally fully or partially substituted C 1 To C 6 An alkyl, alkenyl or alkynyl group, such as a fluorinated alkyl group, and X is selected from the group consisting of: F. cl, H, CF 3 And optionally substituted such as at least partially fluorinated C 1 To C 6 Alkyl, alkenyl OR alkynyl, and the group OR may be cis OR trans relative to any other group.
2. Use of a non-aqueous battery electrolyte formulation comprising a compound of formula 1 in a battery
Wherein the method comprises the steps of
R is selected from the group consisting of: optionally fully or partially substituted C 1 To C 6 An alkyl, alkenyl or alkynyl group, such as a fluorinated alkyl group, and X is selected from the group consisting of: F. cl, H, CF 3 And optionally substituted such as at least partially fluorinated C 1 To C 6 Alkyl, alkenyl OR alkynyl, and the group OR may be cis OR trans relative to any other group.
3. The use according to claim 1 or 2, wherein the formulation comprises a metal electrolyte salt, the metal electrolyte salt being present in an amount of 0.1wt% to 20wt% relative to the total mass of the non-aqueous electrolyte formulation.
4. The use according to claim 3, wherein the metal salt is a lithium, sodium, magnesium, calcium, lead, zinc or nickel salt.
5. The use according to claim 4, wherein the metal salt is a lithium salt selected from the group comprising: lithium hexafluorophosphate (LiPF) 6 ) Lithium hexafluoroarsenate monohydrate (LiAsF) 6 ) Lithium perchlorate (LiClO) 4 ) Lithium tetrafluoroborate (LiBF) 4 ) Lithium triflate (LiSO) 3 CF 3 ) Lithium bis (fluorosulfonyl) imide (Li (FSO) 2 ) 2 N) and lithium bis (trifluoromethanesulfonyl) imide (Li (CF) 3 SO 2 ) 2 N)。
6. The use according to any one of claims 1 to 5, wherein the formulation comprises a further solvent in an amount of 0.1 to 99.9wt% of the liquid component of the formulation.
7. Use according to claim 6, wherein the additional solvent is selected from the group comprising: dimethyl carbonate (DMC), methyl ethyl carbonate (EMC), fluoroethylene carbonate (FEC), propylene Carbonate (PC) or Ethylene Carbonate (EC).
8. According to claim 1 to 7The use according to any one of the preceding claims, wherein in formula (1), R has formula C 1-6 H 0-13 Z 0-13 (wherein Z is one or more of F, cl, br, I), such as fully/partially fluorinated C 1 To C 6 An alkyl group.
9. A battery electrolyte formulation comprising a compound of formula 1.
10. A formulation comprising a metal ion and a compound of formula 1, optionally in combination with a solvent
Wherein the method comprises the steps of
R 1-4 Selected from the group consisting of: optionally fully or partially substituted C 1 To C 6 An alkyl, alkenyl or alkynyl group, such as a fluorinated alkyl group, and X is selected from the group consisting of: F. cl, H, CF 3 And optionally substituted such as C which may be at least partially fluorinated 1 To C 6 Alkyl, alkenyl OR alkynyl, and-OR 4 Radicals R relative to radicals R 1 、R 2 Or R is 3 Either of which may be cis or trans.
11. A battery comprising a battery electrolyte formulation comprising a compound of formula 1
Wherein the method comprises the steps of
R is selected from the group consisting of: optionally fully or partially substituted C 1 To C 6 An alkyl, alkenyl or alkynyl group, such as a fluorinated alkyl group, and X is selected from the group consisting of: F. cl, H, CF 3 Optionally substituted such as at least partiallyFluorinated C 1 To C 6 Alkyl, alkenyl OR alkynyl, and the-OR group may be cis OR trans relative to any other group X.
12. The battery/formulation according to any one of claims 9 to 11, wherein in formula (1) and/or formula (2), R has formula C 1-6 H 0-13 Z 0-13 (wherein Z is one or more of F, cl, br, I), such as fully/partially fluorinated C 1 To C 6 An alkyl group.
13. The battery/formulation of any one of claims 9 to 12, wherein the formulation comprises a metal electrolyte salt present in an amount of 0.1wt% to 20wt% relative to the total mass of the nonaqueous electrolyte formulation.
14. The battery/formulation of claim 13, wherein the metal salt is a lithium salt, sodium salt, magnesium salt, calcium salt, lead salt, zinc salt, or nickel salt.
15. The battery/formulation of claim 14, wherein the metal salt is a lithium salt selected from the group comprising: lithium hexafluorophosphate (LiPF) 6 ) Lithium hexafluoroarsenate monohydrate (LiAsF) 6 ) Lithium perchlorate (LiClO) 4 ) Lithium tetrafluoroborate (LiBF) 4 ) Lithium triflate (LiSO) 3 CF 3 ) Lithium bis (fluorosulfonyl) imide (Li (FSO) 2 ) 2 N) and lithium bis (trifluoromethanesulfonyl) imide (Li (CF) 3 SO 2 ) 2 N)。
16. The battery/formulation of any one of claims 9 to 15, wherein the formulation comprises an additional solvent in an amount of 0.1wt% to 99.9wt% of the liquid component of the formulation.
17. The battery/formulation of claim 16, wherein the additional solvent is selected from the group comprising: dimethyl carbonate (DMC), methyl ethyl carbonate (EMC), fluoroethylene carbonate (FEC), propylene Carbonate (PC) and Ethylene Carbonate (EC).
18. A method of reducing the flammability of a battery and/or battery electrolyte, said method comprising adding a formulation comprising a compound of formula 1
Wherein the method comprises the steps of
R is selected from the group consisting of: optionally fully or partially substituted C 1 To C 6 An alkyl, alkenyl or alkynyl group, such as a fluorinated alkyl group, and X is selected from the group consisting of: F. cl, H, CF 3 And optionally substituted such as at least partially fluorinated C 1 To C 6 Alkyl, alkenyl OR alkynyl, and the-OR group may be cis OR trans relative to any other group X.
19. A method of powering an article, the method comprising using a battery comprising a battery electrolyte formulation comprising a compound of formula 1
Wherein the method comprises the steps of
R is selected from the group consisting of: optionally fully or partially substituted C 1 To C 6 An alkyl, alkenyl or alkynyl group, such as a fluorinated alkyl group, and x is selected from the group consisting of: F. cl, H, CF 3 And optionally substituted such as at least partially fluorinated C 1 To C 6 Alkyl, alkenyl OR alkynyl, and the-OR group may be cis OR trans relative to any other group X.
20. A method of retrofitting a battery electrolyte formulation, the method comprising: (a) At least partially replacing the battery electrolyte with a battery electrolyte formulation comprising a compound of formula 1; and/or (b) supplementing the battery electrolyte with a battery electrolyte formulation comprising a compound of formula 1
Wherein the method comprises the steps of
R is selected from the group consisting of: optionally fully or partially substituted C 1 To C 6 An alkyl, alkenyl or alkynyl group, such as a fluorinated alkyl group, and X is selected from the group consisting of: F. cl, H, CF 3 And optionally substituted such as at least partially fluorinated C 1 To C 6 Alkyl, alkenyl OR alkynyl, and the-OR group may be cis OR trans relative to any other group X.
21. Method for preparing preparation containing compound of formula 1
Wherein the method comprises the steps of
R is selected from the group consisting of: optionally fully or partially substituted C 1 To C 6 An alkyl, alkenyl or alkynyl group, such as a fluorinated alkyl group, and X is selected from the group consisting of: F. cl, H, CF 3 And optionally substituted such as at least partially fluorinated C 1 To C 6 Alkyl, alkenyl OR alkynyl, and the-OR group may be cis OR trans relative to any other group X;
the method is carried out by reacting a compound of formula 2a and/or formula 2b
With an alcohol ROH in the presence of a strong base, optionally in the presence of a solvent, under suitable temperature and pressure conditions.
22. A method of preparing a battery electrolyte formulation comprising mixing a compound of formula 1 with ethylene carbonate, propylene carbonate or fluoroethylene carbonate and lithium hexafluorophosphate.
23. A method for improving battery capacity/charge transfer within a battery/battery life, etc. by using a compound of formula 1.
24. The method of any one of claims 18 to 23, wherein the formulation comprises a metal electrolyte salt present in an amount of 0.1wt% to 20wt% relative to the total mass of the non-aqueous electrolyte formulation.
25. The method of claim 24, wherein the metal salt is a lithium salt, sodium salt, magnesium salt, calcium salt, lead salt, zinc salt, or nickel salt.
26. The method of claim 25, wherein the metal salt is a lithium salt selected from the group comprising: lithium hexafluorophosphate (LiPF) 6 ) Lithium hexafluoroarsenate monohydrate (LiAsF) 6 ) Lithium perchlorate (LiClO) 4 ) Lithium tetrafluoroborate (LiBF) 4 ) Lithium triflate (LiSO) 3 CF 3 ) Lithium bis (fluorosulfonyl) imide (Li (FSO) 2 ) 2 N) and lithium bis (trifluoromethanesulfonyl) imide (Li (CF) 3 SO 2 ) 2 N)。
27. The method of any one of claims 18 to 26, wherein the formulation comprises an additional solvent in an amount of 0.1wt% to 99.9wt% of the liquid component of the formulation.
28. The method of claim 26, wherein the additional solvent is selected from the group comprising: dimethyl carbonate (DMC), methyl ethyl carbonate (EMC), fluoroethylene carbonate (FEC), propylene Carbonate (PC) and Ethylene Carbonate (EC).
29. The method of any one of claims 18 to 28, wherein in formula (1) and/or formula (2), R has formula C 1-6 H 0-13 Z 0-13 (wherein Z is one or more of F, cl, br, I), such as fully/partially fluorinated C 1 To C 6 An alkyl group.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202063124391P | 2020-12-11 | 2020-12-11 | |
| US63/124,391 | 2020-12-11 | ||
| GB2102234.8 | 2021-02-17 | ||
| PCT/GB2021/053226 WO2022123253A1 (en) | 2020-12-11 | 2021-12-09 | Composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116547850A true CN116547850A (en) | 2023-08-04 |
Family
ID=75339016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202180083085.2A Pending CN116547850A (en) | 2020-12-11 | 2021-12-09 | Composition and method for producing the same |
Country Status (3)
| Country | Link |
|---|---|
| CN (1) | CN116547850A (en) |
| GB (1) | GB202102234D0 (en) |
| TW (1) | TW202234740A (en) |
-
2021
- 2021-02-17 GB GBGB2102234.8A patent/GB202102234D0/en not_active Ceased
- 2021-12-09 CN CN202180083085.2A patent/CN116547850A/en active Pending
- 2021-12-10 TW TW110146386A patent/TW202234740A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB202102234D0 (en) | 2021-03-31 |
| TW202234740A (en) | 2022-09-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US11177507B2 (en) | Electrolyte for lithium secondary battery and lithium secondary battery including the same | |
| JP5063448B2 (en) | Nonaqueous electrolyte and nonaqueous electrolyte secondary battery including the nonaqueous electrolyte | |
| US20220393238A1 (en) | Composition | |
| JP7326681B2 (en) | Non-aqueous electrolyte for batteries and lithium secondary batteries | |
| CN115485903A (en) | Electrolyte additive for secondary battery, non-aqueous electrolyte for secondary battery comprising same, and secondary battery | |
| JP2018170217A (en) | Nonaqueous electrolyte solution for battery and lithium secondary battery | |
| JP2022552872A (en) | Composition | |
| CN116547850A (en) | Composition and method for producing the same | |
| US20240021889A1 (en) | Composition | |
| US20230361346A1 (en) | Composition | |
| US20240234814A1 (en) | Composition | |
| JP2022552351A (en) | Composition | |
| CN116569375A (en) | Composition and method for producing the same | |
| JP2022553527A (en) | Composition | |
| EP4260397A1 (en) | Composition | |
| JP2013196821A (en) | Polymer, and secondary battery |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |