JP5795634B2 - ＰＯＦ３またはＰＦ５からのＬｉＰＯ２Ｆ２の製造 - Google Patents
ＰＯＦ３またはＰＦ５からのＬｉＰＯ２Ｆ２の製造 Download PDFInfo
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- JP5795634B2 JP5795634B2 JP2013522214A JP2013522214A JP5795634B2 JP 5795634 B2 JP5795634 B2 JP 5795634B2 JP 2013522214 A JP2013522214 A JP 2013522214A JP 2013522214 A JP2013522214 A JP 2013522214A JP 5795634 B2 JP5795634 B2 JP 5795634B2
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- JP
- Japan
- Prior art keywords
- lipo
- carbonate
- reaction
- lipf
- solvent
- 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.)
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- 238000004519 manufacturing process Methods 0.000 title claims description 13
- FFUQCRZBKUBHQT-UHFFFAOYSA-N phosphoryl fluoride Chemical compound FP(F)(F)=O FFUQCRZBKUBHQT-UHFFFAOYSA-N 0.000 title description 4
- 229910012265 LiPO2F2 Inorganic materials 0.000 title 1
- 229910019256 POF3 Inorganic materials 0.000 title 1
- 101100408805 Schizosaccharomyces pombe (strain 972 / ATCC 24843) pof3 gene Proteins 0.000 title 1
- 229910012258 LiPO Inorganic materials 0.000 claims description 125
- 229910018119 Li 3 PO 4 Inorganic materials 0.000 claims description 61
- 239000000203 mixture Substances 0.000 claims description 46
- 239000011541 reaction mixture Substances 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000002904 solvent Substances 0.000 description 81
- 229910013870 LiPF 6 Inorganic materials 0.000 description 67
- 238000006243 chemical reaction Methods 0.000 description 67
- -1 siloxanes Chemical class 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 239000007787 solid Substances 0.000 description 22
- 229910001416 lithium ion Inorganic materials 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000012535 impurity Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 15
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 14
- 239000003960 organic solvent Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- 238000000605 extraction Methods 0.000 description 11
- 239000006227 byproduct Substances 0.000 description 10
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 10
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 10
- 239000003792 electrolyte Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 7
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 239000000010 aprotic solvent Substances 0.000 description 5
- 239000008151 electrolyte solution Substances 0.000 description 5
- 229940021013 electrolyte solution Drugs 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000003586 protic polar solvent Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000011877 solvent mixture Substances 0.000 description 4
- SBLRHMKNNHXPHG-UHFFFAOYSA-N 4-fluoro-1,3-dioxolan-2-one Chemical compound FC1COC(=O)O1 SBLRHMKNNHXPHG-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000003948 formamides Chemical class 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 150000005677 organic carbonates Chemical class 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 150000003462 sulfoxides Chemical class 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 2
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-dimethylaminopyridine Substances CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- 229910013872 LiPF Inorganic materials 0.000 description 2
- 101150058243 Lipf gene Proteins 0.000 description 2
- 229910000792 Monel Inorganic materials 0.000 description 2
- QTJOIXXDCCFVFV-UHFFFAOYSA-N [Li].[O] Chemical compound [Li].[O] QTJOIXXDCCFVFV-UHFFFAOYSA-N 0.000 description 2
- JDZCKJOXGCMJGS-UHFFFAOYSA-N [Li].[S] Chemical compound [Li].[S] JDZCKJOXGCMJGS-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910001867 inorganic solvent Inorganic materials 0.000 description 2
- 239000003049 inorganic solvent Substances 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000002642 lithium compounds Chemical class 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000004971 nitroalkyl group Chemical group 0.000 description 2
- 229910052756 noble gas Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000003880 polar aprotic solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000004040 pyrrolidinones Chemical class 0.000 description 2
- 239000011833 salt mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- TWQULNDIKKJZPH-UHFFFAOYSA-K trilithium;phosphate Chemical compound [Li+].[Li+].[Li+].[O-]P([O-])([O-])=O TWQULNDIKKJZPH-UHFFFAOYSA-K 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical class O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- WXBWKMLIVXELSF-UHFFFAOYSA-N 2,2,2-trifluoro-n,n-dimethylacetamide Chemical compound CN(C)C(=O)C(F)(F)F WXBWKMLIVXELSF-UHFFFAOYSA-N 0.000 description 1
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical class NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- LRTRRTZWJXMMGS-UHFFFAOYSA-N 2,2-difluoroethyl ethenyl carbonate Chemical compound FC(F)COC(=O)OC=C LRTRRTZWJXMMGS-UHFFFAOYSA-N 0.000 description 1
- WXVCMUWGHFXASO-UHFFFAOYSA-N 2,2-difluoroethyl ethyl carbonate Chemical compound CCOC(=O)OCC(F)F WXVCMUWGHFXASO-UHFFFAOYSA-N 0.000 description 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 1
- QOARFWDBTJVWJG-UHFFFAOYSA-N 2,2-difluoroethyl methyl carbonate Chemical compound COC(=O)OCC(F)F QOARFWDBTJVWJG-UHFFFAOYSA-N 0.000 description 1
- ZJVUKUFQQGRGIJ-UHFFFAOYSA-N 2,2-difluoroethyl phenyl carbonate Chemical compound FC(F)COC(=O)OC1=CC=CC=C1 ZJVUKUFQQGRGIJ-UHFFFAOYSA-N 0.000 description 1
- CXCMIWOFWYPWSS-UHFFFAOYSA-N 2-(2,2,2-trifluoroacetyl)oxyethyl 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)OCCOC(=O)C(F)(F)F CXCMIWOFWYPWSS-UHFFFAOYSA-N 0.000 description 1
- XVUMEEAIPCCPHI-UHFFFAOYSA-N 2-fluoroethyl fluoromethyl carbonate Chemical compound FCCOC(=O)OCF XVUMEEAIPCCPHI-UHFFFAOYSA-N 0.000 description 1
- NOLGJZJMWUDWQW-UHFFFAOYSA-N 2-fluoroethyl methyl carbonate Chemical compound COC(=O)OCCF NOLGJZJMWUDWQW-UHFFFAOYSA-N 0.000 description 1
- UKJOHKQKTGJHRX-UHFFFAOYSA-N 2-fluoroethyl phenyl carbonate Chemical compound FCCOC(=O)OC1=CC=CC=C1 UKJOHKQKTGJHRX-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- VUZHZBFVQSUQDP-UHFFFAOYSA-N 4,4,5,5-tetrafluoro-1,3-dioxolan-2-one Chemical compound FC1(F)OC(=O)OC1(F)F VUZHZBFVQSUQDP-UHFFFAOYSA-N 0.000 description 1
- CRJXZTRTJWAKMU-UHFFFAOYSA-N 4,4,5-trifluoro-1,3-dioxolan-2-one Chemical compound FC1OC(=O)OC1(F)F CRJXZTRTJWAKMU-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- BUPLCMMXKFWTTA-UHFFFAOYSA-N 4-methylidene-1,3-dioxetan-2-one Chemical compound C=C1OC(=O)O1 BUPLCMMXKFWTTA-UHFFFAOYSA-N 0.000 description 1
- QTZBTBLHYPSFMG-UHFFFAOYSA-N 5-chloro-3-methylpyridin-2-amine Chemical compound CC1=CC(Cl)=CN=C1N QTZBTBLHYPSFMG-UHFFFAOYSA-N 0.000 description 1
- LOXFNHMPHMWCKI-UHFFFAOYSA-N C(OCC(F)F)(OCF)=O.C(OCC(F)(F)F)(OC)=O Chemical compound C(OCC(F)F)(OCF)=O.C(OCC(F)(F)F)(OC)=O LOXFNHMPHMWCKI-UHFFFAOYSA-N 0.000 description 1
- 101000801643 Homo sapiens Retinal-specific phospholipid-transporting ATPase ABCA4 Proteins 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 102100033617 Retinal-specific phospholipid-transporting ATPase ABCA4 Human genes 0.000 description 1
- 229910002808 Si–O–Si Inorganic materials 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical group [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 description 1
- 150000003869 acetamides Chemical class 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005910 alkyl carbonate group Chemical group 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- WLLOZRDOFANZMZ-UHFFFAOYSA-N bis(2,2,2-trifluoroethyl) carbonate Chemical compound FC(F)(F)COC(=O)OCC(F)(F)F WLLOZRDOFANZMZ-UHFFFAOYSA-N 0.000 description 1
- YZWIIIGEQKTIMS-UHFFFAOYSA-N bis(2-fluoroethyl) carbonate Chemical compound FCCOC(=O)OCCF YZWIIIGEQKTIMS-UHFFFAOYSA-N 0.000 description 1
- IQFAIEKYIVKGST-UHFFFAOYSA-N bis(fluoromethyl) carbonate Chemical compound FCOC(=O)OCF IQFAIEKYIVKGST-UHFFFAOYSA-N 0.000 description 1
- PMGNOQUKCGLETL-UHFFFAOYSA-N carbonic acid 1,2-difluoroethene Chemical compound C(O)(O)=O.FC=CF PMGNOQUKCGLETL-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 150000005682 diethyl carbonates Chemical class 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- CSANCJZZMDBNPU-UHFFFAOYSA-N difluoromethyl 2-fluoroethyl carbonate Chemical compound FCCOC(=O)OC(F)F CSANCJZZMDBNPU-UHFFFAOYSA-N 0.000 description 1
- VWCDXEKXDIWXKI-UHFFFAOYSA-N difluoromethyl ethyl carbonate Chemical compound CCOC(=O)OC(F)F VWCDXEKXDIWXKI-UHFFFAOYSA-N 0.000 description 1
- VDGKFLGYHYBDQC-UHFFFAOYSA-N difluoromethyl methyl carbonate Chemical compound COC(=O)OC(F)F VDGKFLGYHYBDQC-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 150000005686 dimethyl carbonates Chemical class 0.000 description 1
- 150000004862 dioxolanes Chemical class 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- DPGXGQNEWAAUKM-UHFFFAOYSA-N ethenyl 2,2,2-trifluoroethyl carbonate Chemical compound FC(F)(F)COC(=O)OC=C DPGXGQNEWAAUKM-UHFFFAOYSA-N 0.000 description 1
- JCBADTLNWNTCNV-UHFFFAOYSA-N ethenyl 2-fluoroethyl carbonate Chemical compound FCCOC(=O)OC=C JCBADTLNWNTCNV-UHFFFAOYSA-N 0.000 description 1
- BDNXATXQVYVLCI-UHFFFAOYSA-N ethenyl fluoromethyl carbonate Chemical compound FCOC(=O)OC=C BDNXATXQVYVLCI-UHFFFAOYSA-N 0.000 description 1
- NIQAXIMIQJNOKY-UHFFFAOYSA-N ethyl 2,2,2-trifluoroethyl carbonate Chemical compound CCOC(=O)OCC(F)(F)F NIQAXIMIQJNOKY-UHFFFAOYSA-N 0.000 description 1
- XLHKMGHXUXYDQJ-UHFFFAOYSA-N ethyl 2-fluoroethyl carbonate Chemical compound CCOC(=O)OCCF XLHKMGHXUXYDQJ-UHFFFAOYSA-N 0.000 description 1
- UHHPUKUEMKPCII-UHFFFAOYSA-N ethyl fluoromethyl carbonate Chemical compound CCOC(=O)OCF UHHPUKUEMKPCII-UHFFFAOYSA-N 0.000 description 1
- ZPBVUMUIOIGYRV-UHFFFAOYSA-N ethyl trifluoromethyl carbonate Chemical compound CCOC(=O)OC(F)(F)F ZPBVUMUIOIGYRV-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012025 fluorinating agent Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- PIQRQRGUYXRTJJ-UHFFFAOYSA-N fluoromethyl methyl carbonate Chemical compound COC(=O)OCF PIQRQRGUYXRTJJ-UHFFFAOYSA-N 0.000 description 1
- KUPHFFIERSZZDV-UHFFFAOYSA-N fluoromethyl phenyl carbonate Chemical compound FCOC(=O)OC1=CC=CC=C1 KUPHFFIERSZZDV-UHFFFAOYSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- IGILRSKEFZLPKG-UHFFFAOYSA-M lithium;difluorophosphinate Chemical compound [Li+].[O-]P(F)(F)=O IGILRSKEFZLPKG-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- YSYBYIDPNZPQLJ-UHFFFAOYSA-N methyl trifluoromethyl carbonate Chemical compound COC(=O)OC(F)(F)F YSYBYIDPNZPQLJ-UHFFFAOYSA-N 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- NGGUSKNBBASYGO-UHFFFAOYSA-N phenyl 2,2,2-trifluoroethyl carbonate Chemical compound FC(F)(F)COC(=O)OC1=CC=CC=C1 NGGUSKNBBASYGO-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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
- H01M10/0561—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of inorganic materials only
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B9/00—General methods of preparing halides
- C01B9/08—Fluorides
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B25/00—Phosphorus; Compounds thereof
- C01B25/10—Halides or oxyhalides of phosphorus
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B25/00—Phosphorus; Compounds thereof
- C01B25/16—Oxyacids of phosphorus; Salts thereof
- C01B25/26—Phosphates
- C01B25/455—Phosphates containing halogen
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01D—COMPOUNDS OF ALKALI METALS, i.e. LITHIUM, SODIUM, POTASSIUM, RUBIDIUM, CAESIUM, OR FRANCIUM
- C01D15/00—Lithium compounds
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
-
- 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
- H01M10/0561—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of inorganic materials only
- H01M10/0563—Liquid materials, e.g. for Li-SOCl2 cells
-
- 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
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
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- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
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- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Secondary Cells (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
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| EP10171881.5 | 2010-08-04 | ||
| EP10171881 | 2010-08-04 | ||
| EP10188108.4 | 2010-10-19 | ||
| EP10188108 | 2010-10-19 | ||
| PCT/EP2011/063106 WO2012016924A1 (en) | 2010-08-04 | 2011-07-29 | Manufacture of lipo2f2 from pof3 or pf5 |
Publications (3)
| Publication Number | Publication Date |
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| JP2013534205A JP2013534205A (ja) | 2013-09-02 |
| JP2013534205A5 JP2013534205A5 (enExample) | 2014-07-24 |
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| EP (1) | EP2611731A1 (enExample) |
| JP (1) | JP5795634B2 (enExample) |
| KR (1) | KR20130099019A (enExample) |
| CN (1) | CN103052592B (enExample) |
| TW (1) | TW201210932A (enExample) |
| WO (1) | WO2012016924A1 (enExample) |
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| KR20160092063A (ko) | 2005-10-20 | 2016-08-03 | 미쓰비시 가가꾸 가부시키가이샤 | 리튬 2 차 전지 및 그것에 사용하는 비수계 전해액 |
| EP2702631A1 (en) | 2011-04-26 | 2014-03-05 | Solvay SA | Lithium air battery cell |
| EP2744753A1 (en) * | 2011-08-16 | 2014-06-25 | Solvay SA | Manufacture of mixtures comprising lipo2f2 and lipf6 |
| US9595737B2 (en) | 2012-05-11 | 2017-03-14 | Ube Industries, Ltd. | Non-aqueous electrolyte and power storage device using same |
| EP2705893A1 (en) | 2012-09-05 | 2014-03-12 | Solvay SA | Process for separating acid-containing gas mixtures |
| EP2712843A1 (de) * | 2012-09-28 | 2014-04-02 | LANXESS Deutschland GmbH | Herstellung von hochreinem Lithiumdifluorphosphat |
| JP5715725B2 (ja) * | 2013-06-07 | 2015-05-13 | ステラケミファ株式会社 | ジフルオロリン酸塩の精製方法 |
| EP2842908A1 (en) | 2013-08-28 | 2015-03-04 | Solvay SA | Production of metal difluorophosphates in liquid phase |
| WO2015028346A1 (en) * | 2013-08-28 | 2015-03-05 | Solvay Sa | Production of metal difluorophosphates in an inorganic solvent |
| WO2016031316A1 (ja) * | 2014-08-25 | 2016-03-03 | 宇部興産株式会社 | 非水電解液、それを用いた蓄電デバイス、及びそれに用いるリン化合物 |
| JP6520064B2 (ja) * | 2014-11-19 | 2019-05-29 | セントラル硝子株式会社 | 非水電解液電池用電解液及びリチウム非水電解液電池 |
| JP6428222B2 (ja) * | 2014-12-09 | 2018-11-28 | セントラル硝子株式会社 | ジフルオロリン酸リチウム粉体の製造方法およびジフルオロリン酸リチウム |
| WO2018066896A2 (ko) * | 2016-10-06 | 2018-04-12 | 임광민 | 디플루오로인산리튬의 제조방법 |
| CN106829908B (zh) * | 2016-12-23 | 2018-10-23 | 山东海容电源材料股份有限公司 | 一种二氟磷酸锂的制备方法及含有二氟磷酸锂的锂离子电池非水电解液 |
| JP6921128B2 (ja) * | 2017-01-20 | 2021-08-18 | 三井化学株式会社 | ジフルオロリン酸リチウムの製造方法 |
| US11738998B2 (en) * | 2017-01-31 | 2023-08-29 | Mitsui Chemicals, Inc. | Method for producing lithium difluorophosphate |
| CN106882782B (zh) * | 2017-03-25 | 2019-02-12 | 山东永浩新材料科技有限公司 | 一种二氟磷酸锂的合成方法 |
| CN109133023B (zh) * | 2017-06-27 | 2021-12-31 | 天津金牛电源材料有限责任公司 | 一种二氟磷酸锂制备过程中非水溶剂的循环利用方法 |
| WO2019018999A1 (zh) * | 2017-07-25 | 2019-01-31 | 江苏长园华盛新能源材料有限公司 | 二氟磷酸锂的制备方法 |
| WO2019061802A1 (zh) * | 2017-09-27 | 2019-04-04 | 惠州市大道新材料科技有限公司 | 一种二氟磷酸锂的制备方法 |
| CN108178139A (zh) * | 2018-02-09 | 2018-06-19 | 天津金牛电源材料有限责任公司 | 一种在制备二氟磷酸锂过程中提高产品收率的方法 |
| HUE070447T2 (hu) | 2018-05-04 | 2025-06-28 | Umicore Nv | Lítium-kobalt-oxid szekunder akkumulátor, amely fluorozott elektrolitot és pozitív elektróda anyagot tartalmaz nagyfeszültségû alkalmazásokhoz |
| KR20210038420A (ko) | 2018-05-04 | 2021-04-07 | 솔베이(소시에떼아노님) | 비수성 액체 전해질 조성물 |
| US12482862B2 (en) | 2018-05-04 | 2025-11-25 | Umicore | Ni based lithium-ion secondary battery comprising a fluorinated electrolyte |
| CN108408711B (zh) * | 2018-05-16 | 2020-02-04 | 如鲲(山东)新材料科技有限公司 | 一种二氟磷酸锂的制备方法 |
| CN111646453B (zh) * | 2020-06-08 | 2021-09-10 | 苏州固锂新能源科技有限公司 | 一种二氟磷酸锂的制备方法和纯化工艺 |
| CN112028047A (zh) * | 2020-09-14 | 2020-12-04 | 湖南博信新能源科技有限公司 | 一种二氟磷酸锂的制备方法 |
| CN112456465A (zh) * | 2020-12-11 | 2021-03-09 | 安阳工学院 | 一种二氟磷酸锂的制备方法 |
| CN112537763B (zh) * | 2020-12-23 | 2023-08-22 | 九江天赐高新材料有限公司 | 一种气固液三相合成二氟磷酸锂的方法 |
| CN113148970A (zh) * | 2021-03-12 | 2021-07-23 | 九江天赐高新材料有限公司 | 一种高纯二氟磷酸锂的制备方法 |
| CN115285964A (zh) * | 2022-08-03 | 2022-11-04 | 多氟多新材料股份有限公司 | 一种二氟磷酸锂的制备方法 |
| CN115571900A (zh) * | 2022-11-21 | 2023-01-06 | 东营领仕科技咨询有限公司 | 一种二氟磷酸锂联产六氟磷酸锂的制备方法 |
| CN117023549B (zh) * | 2023-08-05 | 2024-06-25 | 湖北百杰瑞新材料股份有限公司 | 一种二氟磷酸锂的制备方法 |
| CN118529750A (zh) * | 2024-07-26 | 2024-08-23 | 杭州万锂达新能源科技有限公司 | 一种同时制备六氟磷酸盐与二氟磷酸盐的方法 |
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| US4880714A (en) | 1989-02-27 | 1989-11-14 | Duracell Inc. | Method for preparing non-aqueous electrolytes |
| JP3173225B2 (ja) | 1993-05-26 | 2001-06-04 | ソニー株式会社 | 非水電解液二次電池 |
| CA2104718C (en) | 1993-08-24 | 1999-11-16 | Huanyu Mao | Simplified preparation of lipf6 based electrolyte for non-aqueous batteries |
| JPH07254415A (ja) | 1993-12-20 | 1995-10-03 | Wilson Greatbatch Ltd | 電気化学電池およびその電圧遅延を減少させる方法 |
| US6645451B1 (en) | 1996-06-26 | 2003-11-11 | Solvay Fluor Und Derivate Gmbh | Method of preparing inorganic pentafluorides |
| EP1017188A3 (en) | 1998-12-30 | 2001-12-12 | Lucent Technologies Inc. | Method and system for high speed data access from remote locations |
| JP2000201086A (ja) | 1999-01-07 | 2000-07-18 | Sony Corp | デ―タ受信装置およびデ―タ受信方法 |
| DE10016816A1 (de) | 2000-04-05 | 2001-10-11 | Solvay Fluor & Derivate | Verwendung von Alkoxyestern |
| JP4604505B2 (ja) | 2004-02-09 | 2011-01-05 | 三菱化学株式会社 | ジフルオロリン酸リチウムの製造方法、ならびに、非水系電解液及びこれを用いた非水系電解液二次電池 |
| KR101227445B1 (ko) | 2004-10-19 | 2013-01-29 | 미쓰비시 가가꾸 가부시키가이샤 | 디플루오로인산염의 제조 방법, 이차전지용 비수계 전해질용액 및 비수계 전해질 이차전지 |
| JP5228270B2 (ja) * | 2004-10-19 | 2013-07-03 | 三菱化学株式会社 | ジフルオロリン酸塩の製造方法、二次電池用非水系電解液及び非水系電解液二次電池 |
| JP4952080B2 (ja) * | 2005-06-20 | 2012-06-13 | 三菱化学株式会社 | 二次電池用非水系電解液及び非水系電解液二次電池 |
| WO2006137177A1 (ja) | 2005-06-20 | 2006-12-28 | Mitsubishi Chemical Corporation | ジフルオロリン酸塩の製造方法、二次電池用非水系電解液及び非水系電解液二次電池 |
| EP2061115B1 (en) * | 2006-08-22 | 2015-04-01 | Mitsubishi Chemical Corporation | Lithium difluorophosphate, electrolytic solution containing lithium difluorophosphate, process for producing lithium difluorophosphate, process for producing nonaqueous electrolytic solution, nonaqueous electrolytic solution, and nonaqueous-electrolytic-solution secondary cell employing the same |
| JP5277550B2 (ja) * | 2007-03-12 | 2013-08-28 | セントラル硝子株式会社 | ジフルオロリン酸リチウムの製造方法及びこれを用いた非水電解液電池 |
| CN102036912B (zh) | 2008-12-02 | 2013-02-27 | 斯泰拉化工公司 | 二氟磷酸盐的制造方法、非水电解液以及非水电解质二次电池 |
| WO2012004188A1 (en) | 2010-07-08 | 2012-01-12 | Solvay Sa | Manufacture of lipo2f2 and crystalline lipo2f2 |
| WO2012004187A2 (en) | 2010-07-08 | 2012-01-12 | Solvay Sa | Manufacture of lipo2f2 |
| EP2744753A1 (en) | 2011-08-16 | 2014-06-25 | Solvay SA | Manufacture of mixtures comprising lipo2f2 and lipf6 |
-
2011
- 2011-07-29 WO PCT/EP2011/063106 patent/WO2012016924A1/en not_active Ceased
- 2011-07-29 CN CN201180038321.5A patent/CN103052592B/zh not_active Expired - Fee Related
- 2011-07-29 KR KR1020137005253A patent/KR20130099019A/ko not_active Withdrawn
- 2011-07-29 EP EP11737963.6A patent/EP2611731A1/en not_active Withdrawn
- 2011-07-29 JP JP2013522214A patent/JP5795634B2/ja not_active Expired - Fee Related
- 2011-07-29 US US13/813,387 patent/US8889091B2/en not_active Expired - Fee Related
- 2011-08-01 TW TW100127230A patent/TW201210932A/zh unknown
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|---|---|
| EP2611731A1 (en) | 2013-07-10 |
| TW201210932A (en) | 2012-03-16 |
| JP2013534205A (ja) | 2013-09-02 |
| CN103052592A (zh) | 2013-04-17 |
| US20130129595A1 (en) | 2013-05-23 |
| WO2012016924A1 (en) | 2012-02-09 |
| CN103052592B (zh) | 2016-02-24 |
| KR20130099019A (ko) | 2013-09-05 |
| US8889091B2 (en) | 2014-11-18 |
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