JP4266821B2 - ヘプタフルオロ−2−プロパンスルホネート塩及び電気工学におけるその使用 - Google Patents
ヘプタフルオロ−2−プロパンスルホネート塩及び電気工学におけるその使用 Download PDFInfo
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- JP4266821B2 JP4266821B2 JP2003524962A JP2003524962A JP4266821B2 JP 4266821 B2 JP4266821 B2 JP 4266821B2 JP 2003524962 A JP2003524962 A JP 2003524962A JP 2003524962 A JP2003524962 A JP 2003524962A JP 4266821 B2 JP4266821 B2 JP 4266821B2
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- alkyl
- tetraalkylammonium
- lithium
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- 238000004870 electrical engineering Methods 0.000 title claims description 7
- SNHPHIVOTMMDRF-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonic acid Chemical class OS(=O)(=O)C(F)(C(F)(F)F)C(F)(F)F SNHPHIVOTMMDRF-UHFFFAOYSA-N 0.000 title abstract description 9
- -1 alkalimetal salts Chemical class 0.000 claims abstract description 27
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 239000003792 electrolyte Substances 0.000 claims abstract description 16
- 239000003990 capacitor Substances 0.000 claims abstract description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 11
- 150000005621 tetraalkylammonium salts Chemical class 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 14
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 13
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 12
- 229910001416 lithium ion Inorganic materials 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000011575 calcium Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- XBWQFDNGNOOMDZ-UHFFFAOYSA-N 1,1,2,2,3,3,3-heptafluoropropane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)F XBWQFDNGNOOMDZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 229910003002 lithium salt Inorganic materials 0.000 claims description 5
- 159000000002 lithium salts Chemical class 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 claims description 3
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 2
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 claims description 2
- JEBJGWOZEBNRFH-UHFFFAOYSA-L calcium;1,1,2,2,3,3,3-heptafluoropropane-1-sulfonate Chemical compound [Ca+2].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)F JEBJGWOZEBNRFH-UHFFFAOYSA-L 0.000 claims 2
- UJDPILFSJJSABZ-UHFFFAOYSA-M lithium;1,1,2,2,3,3,3-heptafluoropropane-1-sulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)F UJDPILFSJJSABZ-UHFFFAOYSA-M 0.000 claims 2
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 claims 1
- 229910001634 calcium fluoride Inorganic materials 0.000 claims 1
- 159000000007 calcium salts Chemical class 0.000 claims 1
- 150000004714 phosphonium salts Chemical class 0.000 abstract description 5
- 238000000034 method Methods 0.000 description 12
- YYBMGVRXEFBHTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonyl fluoride Chemical compound FC(F)(F)C(F)(C(F)(F)F)S(F)(=O)=O YYBMGVRXEFBHTL-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011877 solvent mixture Substances 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- LAPDOIBRBOGRLP-UHFFFAOYSA-M lithium;1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(C(F)(F)F)C(F)(F)F LAPDOIBRBOGRLP-UHFFFAOYSA-M 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 229910004261 CaF 2 Inorganic materials 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 229910001508 alkali metal halide Inorganic materials 0.000 description 2
- 150000008045 alkali metal halides Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 238000005868 electrolysis reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000003948 formamides Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 2
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 1
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical class O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- PPDFQRAASCRJAH-UHFFFAOYSA-N 2-methylthiolane 1,1-dioxide Chemical class CC1CCCS1(=O)=O PPDFQRAASCRJAH-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000006824 Eschweiler-Clarke methylation reaction Methods 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 238000011387 Li's method Methods 0.000 description 1
- 229910013870 LiPF 6 Inorganic materials 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical group [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical group [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 239000005935 Sulfuryl fluoride Substances 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000005910 alkyl carbonate group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- NCMHKCKGHRPLCM-UHFFFAOYSA-N caesium(1+) Chemical group [Cs+] NCMHKCKGHRPLCM-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 238000012983 electrochemical energy storage Methods 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940006487 lithium cation Drugs 0.000 description 1
- 238000011034 membrane dialysis Methods 0.000 description 1
- NNCAWEWCFVZOGF-UHFFFAOYSA-N mepiquat Chemical compound C[N+]1(C)CCCCC1 NNCAWEWCFVZOGF-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 229910001419 rubidium ion Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical class O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- ZMQDTYVODWKHNT-UHFFFAOYSA-N tris(2,2,2-trifluoroethyl) phosphate Chemical compound FC(F)(F)COP(=O)(OCC(F)(F)F)OCC(F)(F)F ZMQDTYVODWKHNT-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/06—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing halogen atoms, or nitro or nitroso groups bound to the carbon skeleton
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/04—Hybrid capacitors
- H01G11/06—Hybrid capacitors with one of the electrodes allowing ions to be reversibly doped thereinto, e.g. lithium ion capacitors [LIC]
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/54—Electrolytes
- H01G11/58—Liquid electrolytes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0566—Liquid materials
- H01M10/0568—Liquid materials characterised by the solutes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2300/00—Electrolytes
- H01M2300/0017—Non-aqueous electrolytes
- H01M2300/0025—Organic electrolyte
- H01M2300/0028—Organic electrolyte characterised by the solvent
- H01M2300/0037—Mixture of solvents
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2300/00—Electrolytes
- H01M2300/0017—Non-aqueous electrolytes
- H01M2300/0025—Organic electrolyte
- H01M2300/0028—Organic electrolyte characterised by the solvent
- H01M2300/0037—Mixture of solvents
- H01M2300/004—Three solvents
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- 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
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Power Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Inorganic Chemistry (AREA)
- Secondary Cells (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
- Organic Insulating Materials (AREA)
- Electric Double-Layer Capacitors Or The Like (AREA)
- Primary Cells (AREA)
Description
(CF3)2CFSO3 − M+ (I)
[式中、M+は、Li+、Na+、K+、Cs+、Rb+、R4P+又はR4N+を表し、その際、4個のアルキル基Rは同じ又は異なることができ、C1〜C4−アルキルを表すか又は少なくとも2個のR基は窒素又はリンを含めて非芳香族環系を形成する]の化合物が提供される。
リチウムヘプタフルオロ−2−プロパンスルホネート、(CF3)2CFSO3Liの製造
方法1:
Ca塩及び遊離酸を介して
a) 2(CF3)2CFSO2F + 2Ca(OH)2 → [(CF3)2CFSO3]2Ca + CaF2 + 2H2O
ヘプタフルオロ−2−プロパンスルホニルフルオリド(50.4g;0.2mol:252g mol−1)を、密閉した反応容器中で水50ml中の水酸化カルシウム(16.3g;0.22mol;74g mol−1)の懸濁液と一緒に室温で8時間撹拌した。水溶液から生じたCaF2を濾別し、乾燥するまで濃縮した。[(CF3)2CFSO3]2Ca(62.4g;0.11mol;538g mol−1)の収率は58.0%であった。
13C−NMR 95.55ppm(CF、七重項の二重項);120.55ppm(CF3:四重項の二重項)
19F−NMR −73.47ppm(CF3、二重項);−172.87ppm(CF、七重項)。
工程a)からの乾燥した[(CF3)2CFSO3]2Ca(53.8g;0.1mol;538g mol−1)を100%の過剰量のH2SO4と反応させた。遊離スルホン酸(CF3)2CFSO3Hを反応バッチから真空中で直接留去した。(CF3)2CFSO3H(15.7g;0.0628mol;250g mol−1)の収率は62.8%であった。
D2O中の(CF3)2CFSO3H
13C−NMR 93.68ppm(CF、七重項の二重項);118.62ppm(CF3:四重項の二重項)
19F−NMR −74.22ppm(CF3、二重項);−173.08ppm(CF、七重項)。
工程b)からの(CF3)2CFSO3H(10.0g;0.04mol;250g mol−1)を水溶液中でLiOH(0.96g;0.04mol;24g mol−1)で中和し、乾燥するまで濃縮した。(CF3)2CFSO3Li(9.7g;0.038mol;256g mol−1)の収率は95.0%であった。
13C−NMR 95.55ppm(CF、七重項の二重項);121.16ppm(CF3:四重項の二重項)
19F−NMR −73.18ppm(CF3、二重項);−172.78ppm(CF、七重項)。
スルホニルフルオリド及び塩基から直接
(CF3)2CFSO2F + 2LiOH → (CF3)2CFSO3Li + LiF + H2O
ヘプタフルオロ−2−プロパンスルホニルフルオリド(25.2g;0.1mol:252g mol−1)を、密閉した反応容器中で水30ml中の水酸化リチウム(4.8g;0.2mol;24g mol−1)の溶液と一緒に室温で24時間撹拌した。この水溶液を乾燥するまで濃縮した。この残留物を有機溶剤、例えばジメチルカーボネートで抽出し、生じた(CF3)2CFSO3LiからLiFを分離した。この有機相を乾燥し、引き続き濃縮した。(CF3)2CFSO3Li(20.7g;0.0808mol;256g mol−1)の収率は80.8%であった。得られた生成物は、方法1により得られた生成物と同じであった。
リチウムヘプタフルオロ−2−プロパンスルホネートを有する電解質
この電解質は、それぞれの溶剤混合物中にこの塩を溶かすことにより製造した。この場合、例2.2もしくは2.4の2Mol/lの値は、溶解度についての限界ではない。使用した溶剤及び存在する塩濃度を表1にまとめた。
リチウムヘプタフルオロ−2−プロパンスルホネートを有する電解質
Claims (11)
- 一般式I
(CF3)2CFSO3 - M+ (I)
[式中、M+は、Li+ 、R 4P+又はR4N+を表し、その際、4個のアルキル基Rは同じ又は異なることができ、C1〜C4−アルキルを表す]の化合物。 - M+はLi+又はR4N+を表し、その際、4個の置換基Rは同じ又は異なることができ、C1〜C2−アルキルを表す、請求項1記載の化合物。
- 一般式(I)
(CF 3 ) 2 CFSO 3 - M + (I)
[式中、M + は、Li + 、R 4 P + 又はR 4 N + を表し、その際、4個のアルキル基Rは同じ又は異なることができ、C 1 〜C 4 −アルキルを表す]の化合物の製造方法において、
A) リチウム塩の製造のために、
a) (CF3)2CFSO2Fを水酸化リチウムと、有利に水溶液中で反応させ、生成したリチウムヘプタフルオロプロパンスルホネートから生成したフッ化リチウムを分離するか、又は
b) (CF3)2CFSO2FをCa(OH)2と、有利に水溶液中で反応させ、生成したカルシウムヘプタフルオロプロパンスルホネートから生じたフッ化カルシウムを分離し、このカルシウムヘプタフルオロプロパンスルホネートを酸、有利に硫酸で,ヘプタフルオロプロパンスルホン酸とこの酸のカルシウム塩とに変換し、このヘプタフルオロプロパンスルホン酸を水酸化リチウムと、有利に水溶液中で、リチウムヘプタフルオロプロパンスルホネートを形成させながら反応させるか、又は
B) テトラアルキルアンモニウム塩の製造のために、
a) テトラアルキルアンモニウムハロゲン化物をヘプタフルオロプロパンスルホネートのアルカリ金属塩と反応させ、生成したテトラアルキルアンモニウムヘプタフルオロプロパンスルホネートを単離するか又は
b) テトラアルキルアンモニウムヒドロキシドをヘプタフルオロプロパンスルホン酸と反応させるか、又は
C) テトラアルキルアンモニウム塩又はテトラアルキルホスホニウム塩の製造のために、テトラアルキルアンモニウムアルキルカーボネート又はテトラアルキルホスホニウムアルキルカーボネートをヘプタフルオロプロパンスルホン酸と反応させる、一般式(I)の化合物の製造方法。 - 一般式(I)
(CF 3 ) 2 CFSO 3 - M + (I)
[式中、M + は、K + 、Na + 、Li + 、R 4 P + 又はR 4 N + を表し、その際、4個のアルキル基Rは同じ又は異なることができ、C 1 〜C 4 −アルキルを表す]の化合物の電気工学における電池又はキャパシタ用の支持塩としての使用。 - M+はNa+、K + 又Li+を表す一般式(I)の化合物の、電池用の、有利にリチウムイオン−電池用の支持塩としての、請求項4記載の使用。
- M + はLi + を表す一般式(I)の化合物の、リチウムイオン−電池用の支持塩としての、請求項5記載の使用。
- M+はR4P+又はR4N+を表す一般式(I)の化合物の、キャパシタ中での支持塩としての、請求項4記載の使用。
- 支持塩として一般式(I)
(CF 3 ) 2 CFSO 3 - M + (I)
[式中、M + は、K + 、Na + 、Li + 、R 4 P + 又はR 4 N + を表し、その際、4個のアルキル基Rは同じ又は異なることができ、C 1 〜C 4 −アルキルを表す]の1種又は数種の化合物及び電解質溶剤を含有する、電解質。 - 請求項8記載の電解質を有する、電池。
- (CF 3 ) 2 CFSO 3 - M + (I)中のM+はLi+を表す、請求項9記載の電解質を有する、電池。
- 一般式(I)
(CF 3 ) 2 CFSO 3 - M + (I)
[式中、M+が有利にR4P+又はR4N+を表し、その際、4個のアルキル基Rは同じ又は異なることができ、C 1 〜C 4 −アルキルを表す]の化合物を有する、キャパシタ。
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DE10143172A DE10143172A1 (de) | 2001-09-04 | 2001-09-04 | Sulfonylsalze in der Elektrotechnik |
PCT/EP2002/009544 WO2003020691A1 (de) | 2001-09-04 | 2002-08-27 | Heptafluor-2-propansulfonatsalze und ihre verwendung in der elektrotechnik |
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EP1427698A1 (de) | 2004-06-16 |
DE10143172A1 (de) | 2003-03-20 |
DE50214052D1 (de) | 2010-01-14 |
KR100927069B1 (ko) | 2009-11-13 |
EP1427698B1 (de) | 2009-12-02 |
WO2003020691A1 (de) | 2003-03-13 |
CN1551867A (zh) | 2004-12-01 |
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