CN108314694A - 一种锂电池电解液阻燃剂的制备方法 - Google Patents
一种锂电池电解液阻燃剂的制备方法 Download PDFInfo
- Publication number
- CN108314694A CN108314694A CN201810103878.6A CN201810103878A CN108314694A CN 108314694 A CN108314694 A CN 108314694A CN 201810103878 A CN201810103878 A CN 201810103878A CN 108314694 A CN108314694 A CN 108314694A
- Authority
- CN
- China
- Prior art keywords
- fire retardant
- lithium battery
- preparation
- battery electrolytes
- fluorination
- 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
- 239000003063 flame retardant Substances 0.000 title claims abstract description 19
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 229910052744 lithium Inorganic materials 0.000 title claims abstract description 18
- 239000003792 electrolyte Substances 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 238000003682 fluorination reaction Methods 0.000 claims abstract description 23
- ZSTLPJLUQNQBDQ-UHFFFAOYSA-N azanylidyne(dihydroxy)-$l^{5}-phosphane Chemical compound OP(O)#N ZSTLPJLUQNQBDQ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 6
- -1 heterocyclethio Chemical group 0.000 claims description 18
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 13
- 229910052698 phosphorus Inorganic materials 0.000 claims description 13
- 239000011574 phosphorus Substances 0.000 claims description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 8
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 8
- 239000000126 substance Substances 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 235000003270 potassium fluoride Nutrition 0.000 claims description 5
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical group [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims description 5
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 claims description 4
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 claims description 4
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 150000002500 ions Chemical class 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims description 4
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 239000011698 potassium fluoride Substances 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 235000013024 sodium fluoride Nutrition 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 3
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 claims description 2
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 claims description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- ZIPQMKQLYWMSKC-UHFFFAOYSA-N [N+](=O)(OC#N)[O-].[O] Chemical compound [N+](=O)(OC#N)[O-].[O] ZIPQMKQLYWMSKC-UHFFFAOYSA-N 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 239000004411 aluminium Substances 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004802 cyanophenyl group Chemical group 0.000 claims description 2
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 claims description 2
- FUGIIBWTNARRSF-UHFFFAOYSA-N decane-5,6-diol Chemical compound CCCCC(O)C(O)CCCC FUGIIBWTNARRSF-UHFFFAOYSA-N 0.000 claims description 2
- 150000004816 dichlorobenzenes Chemical class 0.000 claims description 2
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 claims description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 2
- 239000003205 fragrance Substances 0.000 claims description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 2
- 229940011051 isopropyl acetate Drugs 0.000 claims description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N p-methylisopropylbenzene Natural products CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-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
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 2
- 229910052701 rubidium Inorganic materials 0.000 claims description 2
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011775 sodium fluoride Substances 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
- QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- GTDKXDWWMOMSFL-UHFFFAOYSA-M tetramethylazanium;fluoride Chemical compound [F-].C[N+](C)(C)C GTDKXDWWMOMSFL-UHFFFAOYSA-M 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical class ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 claims 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- LDDQLRUQCUTJBB-UHFFFAOYSA-N ammonium fluoride Chemical class [NH4+].[F-] LDDQLRUQCUTJBB-UHFFFAOYSA-N 0.000 claims 1
- DSTSOVPKKRBGSU-UHFFFAOYSA-M benzyl(triethyl)azanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC1=CC=CC=C1 DSTSOVPKKRBGSU-UHFFFAOYSA-M 0.000 claims 1
- XCJXQCUJXDUNDN-UHFFFAOYSA-N chlordene Chemical compound C12C=CCC2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl XCJXQCUJXDUNDN-UHFFFAOYSA-N 0.000 claims 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 239000002608 ionic liquid Substances 0.000 abstract description 12
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract description 2
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 2
- 230000036632 reaction speed Effects 0.000 abstract description 2
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 3
- PBIDWHVVZCGMAR-UHFFFAOYSA-N 1-methyl-3-prop-2-enyl-2h-imidazole Chemical compound CN1CN(CC=C)C=C1 PBIDWHVVZCGMAR-UHFFFAOYSA-N 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- PKQYSCBUFZOAPE-UHFFFAOYSA-N 1,2-dibenzyl-3-methylbenzene Chemical compound C=1C=CC=CC=1CC=1C(C)=CC=CC=1CC1=CC=CC=C1 PKQYSCBUFZOAPE-UHFFFAOYSA-N 0.000 description 1
- 0 CC(*)CN(*)C=CN* Chemical compound CC(*)CN(*)C=CN* 0.000 description 1
- GELMJFCSFUJEHB-UHFFFAOYSA-N ClC(C(OP1N=PN=P[N]1)=C(C(Cl)=C1Cl)Cl)=C1Cl Chemical class ClC(C(OP1N=PN=P[N]1)=C(C(Cl)=C1Cl)Cl)=C1Cl GELMJFCSFUJEHB-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 229910052493 LiFePO4 Inorganic materials 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- YUWBVKYVJWNVLE-UHFFFAOYSA-N [N].[P] Chemical compound [N].[P] YUWBVKYVJWNVLE-UHFFFAOYSA-N 0.000 description 1
- FZXODTPQAXDPNA-UHFFFAOYSA-N benzylazanium;fluoride Chemical compound [F-].[NH3+]CC1=CC=CC=C1 FZXODTPQAXDPNA-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 210000005056 cell body Anatomy 0.000 description 1
- 125000006011 chloroethoxy group Chemical group 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 125000002228 disulfide group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical class CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
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Abstract
本发明公开了一种锂电池电解液阻燃剂的制备方法,本发明将氯环三磷腈溶解于有机溶剂中,加入氟化剂和催化剂控制温度反应1‑24h,即得氟代环三磷腈,所述催化剂为原料总质量的1‑50%,所述催化剂为离子液体。本发明使用离子液体为催化剂,大大提高氟化反应速度,提高了反应效率;离子液体无毒易得,使用催化量的离子液体既可以提高效率,又可以降低成本。
Description
技术领域
本发明涉及一种锂电池电解液阻燃剂的制备方法。
背景技术
对于高能量高性能的追求,是电池技术发展的必然方向。磷酸铁锂、钴酸锂已经达到了电池能量密度的天花板,三元材料的发展是必然的事情。三元材料电压平台,能量密度,振实密度都高,但是也存在着安全性差,耐高温性差等缺陷,氮磷系阻燃剂的发明正好解决了这些困扰。在电解液里面添加5-10%的可实现电解液难燃或不燃。另外,还具有抑制电池内部发热的效果,并可抑制电池性能降低。
氯代环三磷腈具有良好的阻燃效果,但是这种阻燃剂容易水解,同时氯对电池体系具有很大的腐蚀作用。最近,研究发现当使用氟对氯进行取代,可以得到黏度较低,兼容性更好的功能性磷腈衍生物。氟代磷腈类化合物可以用作锂离子电池的高效阻燃剂。
目前,磷腈的氟化方法通常是在有机小分子溶剂中进行氟化,生成氟化物进行蒸馏和分馏。由于有机小分子容易挥发,并且和氟代环三磷腈形成共沸物,难以提纯,同时浪费了溶剂,提高了成本。 WO2016165310提供一种离子液体作为其反应体系溶剂,能够提高环三磷腈及其衍生物氟化反应效率,降低提纯成本,但是离子液体相对较贵,成本还是比较高。
发明内容
本发明的目的在于提供一种经济高效氟化反应体系,其采用离子液体作为催化剂,能够提高环三磷腈及其衍生物氟化反应效率,降低成本。
为了实现上述目的,本发明的技术方案是设计一种锂电池电解液阻燃剂的制备方法,包括以下步骤:
将六氯环三磷腈或其衍生物溶于溶剂,加入催化剂离子液体,加入氟化剂,控制温度进行氟化反应,然后蒸馏,制得高纯六氟环三磷腈或其衍生物。
所述六氯环三磷腈及其衍生物的化学式为I:
其中,R1‐R6中至少有一个氯,R1‐R6独自选自C1‐C20的烷基、烷氧基、芳香氧基、杂环氧基、取代的氨基、杂环硫基、杂环二硫基、杂环三硫基、氟代烷氧基、其它取代的烷氧基、芳香基、氰基、硝基、醚氧基、卤素、烯基、炔基。
所述溶剂包含下面的一种或者多种溶剂,溶剂有乙酸乙酯、乙酸正丁酯(包括异构体)、乙酸叔丁酯、乙酸正丙酯、乙酸异丙酯、四氢呋喃、甲基四氢呋喃、环己烷、己烷、乙腈、苯腈、苯、甲苯、氯苯、二氯苯(包括异构体)、二甲苯(包括异构体)、三甲苯(包括异构体)、三氯苯(包括异构体)、二苯醚、甲基叔丁基醚、十氢萘、喹啉、对甲基异丙苯、乙苯、二乙苯、聚乙二醇、乙二醇二甲醚、乙二醇二***、乙二醇二丁醚、二乙二醇二甲醚、二乙二醇二***、二乙二醇二丁醚、N,N-二甲基甲酰胺、二甲亚砜、环丁砜、高温导热油、二苄基甲苯、其它高沸点溶剂、高温熔盐中的一种或多种。
所述离子液体化学结构式为II、III、IV、V:
上述化学式中R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21、R22、R23分别独立选自碳原子在0‐20间的烷基(当碳原子为0时,R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21、R22、R23为氢)、烷氧基、芳香基、羧基、羟基、氰基、硝基、醚氧基、卤素。
优选的,取代基R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21、R22、R23分别独立选自以下基团:甲基、乙基、丙基、丁基、乙烯基、烯丙基、丁烯基、亚乙烯基、苯基、苯甲基或苄基。
其中,阴离子X选自以下几种中的至少一种:AlCl4-、F‐、Cl-、Br、PF6‐、BF4‐、TFSI‐、FSI‐、 BOB‐、ClO4‐。
所述的氟化剂为铵、锂、钠、钾、铷、钙、镁、铝、铬、铁、钴、锑、镍、铜、锌、钛、稀土氟化物或四烷基氟化铵(包括但不局限于四甲基氟化铵、四乙基氟化铵、四丁基氟化铵、三乙基苄基氟化铵)或者四取代氟化磷(包括但不局限于四甲基氟化磷、四乙基氟化磷、四丙基氟化磷、四丁基氟化磷、三乙基苄基氟化磷、四苯基氟化磷)的一种或多种组合,最优氟化物为氟化钠或氟化钾。
所述的氟化温度为10‐300°C,最优温度为100‐150°C。所述的反应时间为2‐98小时,最优时间为12‐24小时。所述的蒸馏温度为40‐300°C。最优温度高于产物沸点10-20°C。
本发明的优点和有益效果在于:与现有技术相比,本发明采用难挥发、无污染的离子液体为催化剂,加快了反应速度,同时降低了成本,后处理简单,产物纯度和产率很高,离子液体可以重复利用。
具体实施方式
下面结合实施例,对本发明的具体实施方式作进一步描述。以下实施例仅用于更加清楚地说明本发明的技术方案,而不能以此来限制本发明的保护范围。
实施例1:
取348克六氯环三磷腈,加入装有100毫升1‐苄基‐3‐甲基吡啶六氟磷酸盐离子液体和1200毫升己烷烧瓶中,然后加入350克氟化钾,在130°C氟化,然后蒸馏,得到六氟环三磷腈。1‐苄基‐3‐甲基吡啶六氟磷酸盐离子液体可以回收利用。
实施例2:
取357克五氯乙氧基环三磷腈,加入装有100毫升1‐苯基‐3‐甲基咪唑四氟硼酸盐离子液体和1200毫升的氯苯烧瓶中,然后加入350克氟化钠,回流氟化,然后蒸馏,得到五氟乙氧基环三磷腈。1‐苯基‐3‐甲基咪唑四氟硼酸盐离子液体回收利用。
实施例3:
取405克五氯苯氧基环三磷腈,加入装有100毫升1‐烯丙‐3‐甲基咪唑六氟磷酸盐离子液体和1200毫升二苯醚的烧瓶中,然后然后加入400克氟化钾,回流氟化,然后蒸馏,得到五氟苯氧基环三磷腈。1‐烯丙‐3‐甲基咪唑六氟磷酸盐离子液体回收利用。
对照试验1:取348克六氯环三磷腈,加入装有1200毫升己烷烧瓶中,然后加入350克氟化钾,在130°C氟化,没有目标产品六氟环三磷腈生成。
以上所述仅是本发明的优选实施方式,应当指出,对于本技术领域的普通技术人员来说,在不脱离本发明技术原理的前提下,还可以做出若干改进和润饰,这些改进和润饰也应视为本发明的保护范围。
Claims (10)
1.一种锂电池电解液阻燃剂的制备方法,其特征在于,包括以下步骤:将六氯环三磷腈或其衍生物溶于溶剂,加入催化剂离子液体,加入氟化剂,控制温度进行氟化反应,然后蒸馏,制得高纯六氟环三磷腈或其衍生物;所述六氯环三磷腈及其衍生物的化学式为:
其中,R1‐R6中至少有一个氯,R1‐R6独自选自C1‐C20的烷基、烷氧基、芳香氧基、杂环氧基、取代的氨基、杂环硫基、杂环连硫基、杂环三硫基、氟代烷氧基、其它取代的烷氧基、芳香基、氰基、硝基、醚氧基、卤素、烯基、炔基。
2.根据权利要求1所述的一种锂电池电解液阻燃剂的制备方法,其特征在于,所述六氯环三磷腈及其衍生物包括:六氯环三磷腈、五氯环三磷腈、包括但不局限于乙氧基五氯环三磷腈、苯氧基五氯环三磷腈。
3.根据权利要求1所述的一种锂电池电解液阻燃剂的制备方法,其特征在于,所述溶剂为乙酸乙酯、乙酸正丁酯及其异构体、乙酸正丙酯、乙酸异丙酯、四氢呋喃、甲基四氢呋喃、环己烷、己烷、乙腈、苯腈、苯、甲苯、氯苯、二氯苯及其异构体、二甲苯及其异构体、三甲苯及其异构体、三氯苯及其异构体、二苯醚、甲基叔丁基醚、十氢萘、喹啉、对甲基异丙苯、乙苯、二乙苯、聚乙二醇、乙二醇二甲醚、乙二醇二***、乙二醇二丁醚、二乙二醇二甲醚、二乙二醇二***、二乙二醇二丁醚、N,N-二甲基甲酰胺、二甲亚砜、环丁砜、高温导热油、二苄基甲苯、其它高沸点溶剂、高温熔盐中的一种或多种。
4.根据权利要求1所述的一种锂电池电解液阻燃剂的制备方法,其特征在于,所述离子液体化学结构式包括:
,
所述化学式中取代基R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21、R22、R23分别独立选自碳原子在0‐20间的烷基、烷氧基、芳香基、羧基、羟基、氰基、硝基、醚氧基、卤素;所述化学式中阴离子X为AlCl4-、F‐、Cl-、Br、PF6‐、BF4‐、TFSI‐、FSI‐、BOB‐、ClO4‐中的一种或多种。
5.根据权利要求4所述的一种锂电池电解液阻燃剂的制备方法,其特征在于,所述碳原子在0‐20间的烷基,当碳原子为0时,R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21、R22或R23为氢。
6.根据权利要求4或5所述的一种锂电池电解液阻燃剂的制备方法,其特征在于,所述取代基R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21、R22、R23分别独立选自以下基团:甲基、乙基、丙基、丁基、乙烯基、烯丙基、丁烯基、亚乙烯基、苯基、苯甲基或苄基。
7.根据权利要求1所述的一种锂电池电解液阻燃剂的制备方法,其特征在于,所述氟化剂为铵、锂、钠、钾、铷、钙、镁、铝、铬、铁、钴、锑、镍、铜、锌、钛、稀土氟化物或四烷基氟化铵、包括但不局限于四甲基氟化铵、四乙基氟化铵、四丁基氟化铵、三乙基苄基氟化铵或者四取代氟化磷、包括但不局限于四甲基氟化磷、四乙基氟化磷、四丙基氟化磷、四丁基氟化磷、三乙基苄基氟化磷、四苯基氟化磷的一种或多种组合。
8.根据权利要求7所述的一种锂电池电解液阻燃剂的制备方法,其特征在于,所述氟化物为氟化钠或氟化钾。
9.根据权利要求1所述的一种锂电池电解液阻燃剂的制备方法,其特征在于,所述的氟化温度为10‐300°C,所述的反应时间为2‐98小时,所述的蒸馏温度为40‐300°C。
10.根据权利要求9所述的一种锂电池电解液阻燃剂的制备方法,其特征在于,所述氟化温度为100‐150°C,所述反应时间为12‐24小时;所述蒸馏温度高于产物沸点10°C。
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CN112175010A (zh) * | 2020-10-16 | 2021-01-05 | 南京师范大学 | 一种六氟环三磷腈的合成方法 |
CN112175010B (zh) * | 2020-10-16 | 2023-07-21 | 南京师范大学 | 一种六氟环三磷腈的合成方法 |
CN114213387A (zh) * | 2021-12-31 | 2022-03-22 | 云南森美达生物科技股份有限公司 | 黄樟素的富集提取方法 |
CN114213387B (zh) * | 2021-12-31 | 2024-01-09 | 云南森美达生物科技股份有限公司 | 黄樟素的富集提取方法 |
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