CN106604925A - Zwitter ion compound and ion conductor - Google Patents
Zwitter ion compound and ion conductor Download PDFInfo
- Publication number
- CN106604925A CN106604925A CN201580044874.XA CN201580044874A CN106604925A CN 106604925 A CN106604925 A CN 106604925A CN 201580044874 A CN201580044874 A CN 201580044874A CN 106604925 A CN106604925 A CN 106604925A
- Authority
- CN
- China
- Prior art keywords
- ion
- compound
- ion conductor
- carbon number
- zwitterionic compound
- 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
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- 239000010416 ion conductor Substances 0.000 title claims abstract description 33
- -1 ion compound Chemical class 0.000 title abstract description 39
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 40
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 11
- 229910003002 lithium salt Inorganic materials 0.000 claims description 8
- 159000000002 lithium salts Chemical class 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 150000001721 carbon Chemical class 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 11
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 10
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 10
- 229910052744 lithium Inorganic materials 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000008040 ionic compounds Chemical class 0.000 description 6
- 229910001416 lithium ion Inorganic materials 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 150000002466 imines Chemical class 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 125000001118 alkylidene group Chemical group 0.000 description 4
- 239000004020 conductor Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 208000020442 loss of weight Diseases 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241001269238 Data Species 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- 241001044369 Amphion Species 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000255964 Pieridae Species 0.000 description 2
- 235000002597 Solanum melongena Nutrition 0.000 description 2
- 244000061458 Solanum melongena Species 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 229910003473 lithium bis(trifluoromethanesulfonyl)imide Inorganic materials 0.000 description 2
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 description 2
- QSZMZKBZAYQGRS-UHFFFAOYSA-N lithium;bis(trifluoromethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F QSZMZKBZAYQGRS-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- 229950000845 politef Drugs 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 2
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 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 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910013528 LiN(SO2 CF3)2 Inorganic materials 0.000 description 1
- 229910013385 LiN(SO2C2F5)2 Inorganic materials 0.000 description 1
- 229910001290 LiPF6 Inorganic materials 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- FZRTZGZGNIDIIG-UHFFFAOYSA-N azanium 3,3-dibutylheptane-1-sulfonate Chemical compound C(CCC)C(CCS(=O)(=O)[O-])(CCCC)CCCC.[NH4+] FZRTZGZGNIDIIG-UHFFFAOYSA-N 0.000 description 1
- 229940063013 borate ion Drugs 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 150000001768 cations Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- KVMPQUTWRWVTQP-UHFFFAOYSA-N cyanatoboronic acid Chemical compound OB(O)OC#N KVMPQUTWRWVTQP-UHFFFAOYSA-N 0.000 description 1
- KXRNYDKIPJKLTD-UHFFFAOYSA-N cyanoboron Chemical compound [B]C#N KXRNYDKIPJKLTD-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000002608 ionic liquid Substances 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001540 lithium hexafluoroarsenate(V) Inorganic materials 0.000 description 1
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 1
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 1
- WDGKXRCNMKPDSD-UHFFFAOYSA-N lithium;trifluoromethanesulfonic acid Chemical compound [Li].OS(=O)(=O)C(F)(F)F WDGKXRCNMKPDSD-UHFFFAOYSA-N 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910001427 strontium ion Inorganic materials 0.000 description 1
- PWYYWQHXAPXYMF-UHFFFAOYSA-N strontium(2+) Chemical compound [Sr+2] PWYYWQHXAPXYMF-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium 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
- H01M10/056—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
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/62—Selection of inactive substances as ingredients for active masses, e.g. binders, fillers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/02—Details
-
- 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
- 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
- Y02E60/30—Hydrogen technology
- Y02E60/50—Fuel cells
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Electrochemistry (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Inorganic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Sustainable Energy (AREA)
- Sustainable Development (AREA)
- Secondary Cells (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Conductive Materials (AREA)
- Battery Electrode And Active Subsutance (AREA)
- Inert Electrodes (AREA)
Abstract
The present invention relates to: a zwitter ion compound represented by formula (I); and an ion conductor which contains this zwitter ion compound. The present invention provides: a novel zwitter ion compound which has excellent ion conductivity and heat resistance; and an ion conductor which contains this zwitter ion compound. (In the formula, each of R1-R3 independently represents an alkyl group having 1-5 carbon atoms, a cycloalkyl group having 3-8 carbon atoms, an alkenyl group having 2-10 carbon atoms or a substituted or unsubstituted aryl group having 6-20 carbon atoms; and X represents an alkylene group having 2-5 carbon atoms.)
Description
Technical field
The present invention relates to the new type amphoteric ionic compound of ionic conductivity and excellent heat resistance and containing the both sexes from
The ion conductor of sub- compound.
Background technology
In recent years, there is the zwitterionic compound of cation position and anionic site as ion in same intramolecular
The material of conductor, various additives etc. and receive much concern.
For example, recorded in patent documentation 1,2 proton conductor comprising amphion salt and proton donor and with by
Fuel cell of proton conduction layer that the proton conductor is formed etc..
The electrolyte comprising lithium salts and amphoteric ion type ionic liquid has been recorded in patent documentation 3 and the electrolysis has been used
The lithium rechargeable battery of liquid.
The zwitterionic compound as antistatic additive etc. has been recorded in patent documentation 4.
Prior art literature
Patent documentation
Patent documentation 1：Japanese Unexamined Patent Publication 2005-228588 publications (US2006263661A1)
Patent documentation 2：WO2006/025482 separate editions (US2007231647A1)
Patent documentation 3：Japanese Unexamined Patent Publication 2008-243736 publications
Patent documentation 4：Japanese Unexamined Patent Publication 2005-272316 publications.
The content of the invention
Problems to be solved by the invention
As described above, zwitterionic compound is used as the ionic conductivity component of the electrochemical devices such as fuel cell, lithium battery
Material etc. is useful.
However, conventional zwitterionic compound has the tendency of poor heat resistance, there is the risk decomposed in high temperature, because
This is not suitable as the manufacture material of the electrochemical device that very high temperature is reached when driving.
The present invention is carried out in view of the foregoing, be its object is to, there is provided ionic conductivity and excellent heat resistance
New type amphoteric ionic compound and the ion conductor containing the zwitterionic compound.
For the method for solve problem
The present inventor etc. are had made intensive studies to solve above-mentioned problem, are as a result found：With sulfonic group and containing phosphorus atoms
Cationic groups zwitterionic compound ionic conductivity and excellent heat resistance, so as to complete the present invention.
Thus, according to the present invention, there is provided the zwitterionic compound of following (1) and (2), the ion conductor of (3).
(1) zwitterionic compound, which is shown in following formula (I)s,
[chemical formula 1]
In formula, R1~R3Alkyl, the cycloalkyl that carbon number is 3 ~ 8, carbon atom that carbon number is 1 ~ 5 are represented independently of one another
Number for 2 ~ 10 thiazolinyl or substituted or unsubstituted carbon number for 6 ~ 20 aryl, X represent carbon number be 2 ~ 5 Asia
Alkyl.
(2) ion conductor, which contains：Zwitterionic compound and the 1st race of the periodic table of elements described in aforementioned (1) or
The salt of the metal of the 2nd race.
(3) ion conductor according to (2), wherein, the salt of aforementioned metal is lithium salts.
The effect of invention
According to the present invention, there is provided the new type amphoteric ionic compound of ionic conductivity and excellent heat resistance and contain the both sexes
The ion conductor of ionic compound.
Specific embodiment
Hereinafter, by the present invention be divided into 1) zwitterionic compound and 2) ion conductor describing in detail.
In the present invention, " ionic conductivity " of zwitterionic compound refer to ion with the salt comprising ion to be transported
Mobile easness in mixture obtained from mixing, " ionic conductivity " of ion conductor refer to ion in ion conductor
Mobile easness.
1) zwitterionic compound
The zwitterionic compound of the present invention is the compound shown in aforementioned formula (I).
In formula (I), R1~R3Independently of one another represent carbon number for 1 ~ 5 alkyl, carbon number for 3 ~ 8 cycloalkyl,
Carbon number for 2 ~ 10 thiazolinyl or substituted or unsubstituted carbon number for 6 ~ 20 aryl.
R1Alkyl carbon number be 1 ~ 5, be preferably 2 ~ 4.
As R1Alkyl, the straight chained alkyls such as methyl, ethyl, n-pro-pyl, normal-butyl, n-pentyl can be enumerated；Isopropyl,
The branched alkyls such as sec-butyl, the tert-butyl group, isobutyl group.
R1Cycloalkyl carbon number be 3 ~ 8, be preferably 5 ~ 7.
As R1Cycloalkyl, cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl, suberyl, cyclooctyl can be enumerated.
R1Thiazolinyl carbon number be 2 ~ 10, be preferably 3 ~ 8.
As R1Thiazolinyl, vinyl, pi-allyl, 1-butylene base, crotyl, 1- pentenyls etc. can be enumerated.
R1Aryl carbon number be 6 ~ 20, be preferably 6 ~ 10.
As R1Unsubstituted aryl, phenyl, 1- naphthyls, 2- naphthyls etc. can be enumerated.
As the substituent group of substituted aryl, the alkyl that the carbon numbers such as methyl, ethyl are 1 ~ 6 can be enumerated；Methoxyl group, second
The carbon numbers such as epoxide are 1 ~ 6 alkoxyl etc..
Among these, due to ionic conductivity and excellent heat resistance, so R1Preferably carbon number for 1 ~ 5 alkyl,
More preferably carbon number is 2 ~ 4 alkyl.
In formula (I), X represents the alkylidene that carbon number is 2 ~ 5.
It is 2 ~ 5 alkylidene as the carbon number of X, ethylidene, trimethylene, tetramethylene, five methylenes can be enumerated
The straight-chain alkylidene such as base；The branched alkylidenes such as propane -1,2- diyls, butane -1,3- diyls.
The manufacture method of the zwitterionic compound of the present invention is not particularly limited.For example, as shown in following formula, two
Property ionic compound (IV) can be obtained by making corresponding phosphine compound (II) be reacted with sultone compound (III)
.
[chemical formula 2]
(in above-mentioned formula, R1、R2、R3Represent meaning as hereinbefore, n is 0,1,2 or 3).
As aforementioned phosphine compound (II), the trialkyls such as triethyl phosphine, three n-pro-pyl phosphines, tri-n-butyl phosphine can be enumerated
Phosphine；The tricyclic alkyl phosphines such as three cyclopenta phosphines, tricyclohexyl phosphine.
As aforementioned sultone compound (III), can enumerate 1,2- ethane sultone, PS, Isosorbide-5-Nitrae-
Butane sultone, 2,4- butane sultones, 1,5- pentane sultone.
Phosphine compound (II), sultone compound (III) are known compound, can be manufactured by known method and be obtained
Take.Additionally, as phosphine compound (II), sultone compound (III), commercially available product can also be used.
In reaction of the phosphine compound (II) with sultone compound (III), the usage amount phase of sultone compound (III)
For phosphine compound (II) is preferably 0.8 ~ 1.2 equivalent, is more preferably 0.9 ~ 1.1 equivalent.By making sultone compound (III)
Usage amount be in above range, the step of removing unreacted reactant can be omitted or shortened and remove the spent time.
Phosphine compound (II) can be carried out in the absence of a solvent with the reaction of sultone compound (III), it is also possible to
Carry out in the presence of atent solvent.
As atent solvent used, the ether series solvents such as tetrahydrofuran, diethylene glycol dimethyl ether can be enumerated；Acetonitrile, third
The nitrile series solvents such as nitrile；The ketone series solvents such as acetone, butanone；The aromatics hydrocarbon system solvent such as toluene, dimethylbenzene；The halo hydrocarbon system such as chloroform is molten
Agent etc..
During using atent solvent, its usage amount is not particularly limited, relative to 1 mass parts of phosphine compound (II), generally excellent
Elect below 100 mass parts as.
Reaction temperature is not particularly limited, usually -20 ~ 200 DEG C, be preferably 0 ~ 100 DEG C, more preferably 10 ~ 60 DEG C
Scope.Furthermore, it is possible to implement reaction in atmospheric conditions, it is also possible to implement reaction under an increased pressure.
Response time is not particularly limited, usually 12 ~ 336 hours, preferably 24 ~ 168 hours.
From preventing because being oxidized by oxygen, sultone compound (III) hydrolyzing by the moisture in air and causing yield to reduce
From the viewpoint of, reaction is preferably carried out under nitrogen atmosphere.
The carrying out of reaction can be for example, by gas chromatography, high performance liquid chromatography, thin layer chromatography, NMR, IR etc. often
The analysis means of rule are confirming.
After reaction terminates, gained zwitterionic compound can be by pure known to solvent washing, recrystallization, column chromatography etc.
Change method is carrying out purification.
The present invention zwitterionic compound have aforementioned phosphorio as cationic groups and have sulfonic group (-
SO3 -) as anionic property group.
The ionic conductivity and excellent heat resistance of the zwitterionic compound of the present invention having a structure in which.
The ionic conductivity of the zwitterionic compound of the present invention for example can be mixed with lithium salts by measure and be obtained
Mixture ionic conductance being evaluated.
For example, zwitterionic compound of the invention is (mixed with the mixture of double (trifluoro methylsulfonyl) imine lithium (LiTFSI)
Composition and division in a proportion example：Relative to 1 mole of zwitterionic compound, LiTFSI is 1 mole) 60 DEG C at ionic conductance be usually 10-8~
10-2S/cm, be preferably 10-7~10-2S/cm, particularly preferably 10-6~10-2S/cm。
The thermostability of the zwitterionic compound of the present invention is evaluated for example based on loss of weight when carrying out thermogravimetric analysiss.
For example, when carrying out thermogravimetric analysiss under conditions of described in embodiment, temperature when loss of weight ratio reaches 5% is usual
For 300 ~ 600 DEG C, preferably 400 ~ 500 DEG C.
The glass transition temperature of the zwitterionic compound of the present invention is not particularly limited, usually -100 ~+150 DEG C,
Preferably -80 ~+50 DEG C, particularly preferably -60 ~+20 DEG C.
By using glass transition temperature zwitterionic compound within the above range, efficiently can obtain from
The excellent ion conductor of sub- conductivity.
The fusing point of zwitterionic compound of the present invention is not particularly limited, usually 0 ~ 250 DEG C, be preferably 20 ~ 200
℃.By using fusing point zwitterionic compound within the above range, zwitterionic compound can be efficiently obtained not
The ion conductor of easy crystallization.
Due to having these characteristics, therefore, the zwitterionic compound of the present invention can be suitably used as fuel cell
Proton conductor, the lithium ion conductor of lithium rechargeable battery, antistatic additive, dispersant etc..
2) ion conductor
The ion conductor of the present invention contains the zwitterionic compound of the present invention and the gold of the 1st race of the periodic table of elements or the 2nd race
The salt of category.
Ion conductor is derived from the metal ion of these slaines and can relatively freely move in the inside of the ion conductor
Material.
As constitute aforementioned metal salt metal ion, can enumerate the alkali metal such as lithium ion, sodium ion, potassium ion from
Son；The alkaline-earth metal ions such as magnesium ion, calcium ion, strontium ion.
As the anion for constituting aforementioned metal salt, double (fluorine methylsulfonyl) imines ion, double (fluoroform sulphurs can be enumerated
Acyl) imines ion, double (five fluorine second sulphonyl) imines ions, three (trifyl) methide ion, trifluoromethanesulfonic acid root
Ion, hexafluorophosphoricacid acid ions, tetrafluoroborate ion, four cyano borate ion, perchlorate, hexafluoroarsenate root from
Son etc..
As aforementioned metal salt, preferably lithium salts, sodium salt, potassium salt, magnesium salt, more preferably lithium salts.
As lithium salts, double (fluorine methylsulfonyl) imine lithium (LiN (SO can be enumerated2CH2F)2), double (trifluoro methylsulfonyl) imines
Lithium (LiN (SO2CF3)2), double (five fluorine second sulphonyl) imine lithium (LiN (SO2C2F5)2), three (trifyl) lithium methide (LiC
(SO2CF3)3), trifluoromethanesulfonic acid lithium (LiCF3SO3), lithium hexafluoro phosphate (LiPF6), LiBF4 (LiBF4), four cyano boron
Sour lithium (LiB (CN)4), lithium perchlorate (LiClO4), hexafluoroarsenate lithium (LiAsF6) etc..
In the present invention, the slaine of the 1st race of the periodic table of elements or the 2nd race can be used alone one kind, or be applied in combination
It is two or more.
The content of the aforementioned metal salt in ion conductor is usually 0.1 ~ 100 relative to 1 mole of zwitterionic compound and rubs
You, be preferably 0.5 ~ 30 mole.
Ionic conductance at 60 DEG C of the ion conductor of the present invention is usually 10-8~10-2S/cm, be preferably 10-6~10- 2S/cm。
The glass transition temperature of the ion conductor of the present invention is usually -100 ~+50 DEG C, is preferably -90 ~+30 DEG C.
The ion conductor of the present invention can serve as the composition in the dielectric substrate of various electrochemical devices, electrode.
Wherein, the lithium ion conductor containing lithium salts can preferably act as the dielectric substrate of lithium rechargeable battery, electrode
In composition.
The ion conductor of the present invention contains the zwitterionic compound of the present invention, ionic conductivity and excellent heat resistance.Cause
This, by using the ion conductor of the present invention, can obtain safe electrochemical device.
Embodiment
Hereinafter, enumerate embodiment to illustrate in greater detail the present invention.But, the present invention is not completely because of below example
By any restriction.
Part and % in each example is quality criteria in the case where especially not recording.
[embodiment 1]
Under nitrogen atmosphere, input tributylphosphine 6.0g (29.7mmol) and chlorine in the twoport eggplant type flask for possessing Dropping funnel
Imitative 10ml, while content is stirred, is slowly added PS 3.6g (29.7mmol), addition knot at 25 DEG C
Shu Hou, all the elements thing is stirred 168 hours at 40 DEG C.
After reaction terminates, the vacuum distillation from reactant liquor removes solvent, with ethyl acetate wash residual thing, and is done
It is dry, so as to obtain clear crystal (receipts amount：8.8g, yield：91.0%).
Gained clear crystal described below1H-NMR modal datas.
1H-NMR(CDCl3,500MHz)：δ(ppm)=0.96-0.98 (t,J=7.1Hz,9H)、1.5 (m,12H)、2.04-
2.12 (sext,J=8.6Hz,2H)、2.23 (m,6H)、2.66 (m,6H)、2.91-2.93 (t,J=6.6Hz,2H)。
[embodiment 2]
Under nitrogen atmosphere, input triethyl phosphine/THF (tetrahydrofuran) solution in the twoport eggplant type flask for possessing Dropping funnel
(concentration is 1mol/l) 50ml and chloroform 20ml, while content is stirred, is slowly added in 1,3- propane sulphurs at 25 DEG C
Ester 6.1g (50mmol), after addition terminates, all the elements thing is stirred 168 hours at 40 DEG C.
After reaction terminates, which is washed with ethyl acetate, and is dried by leaching precipitate, so as to obtain clear crystal
(receipts amount：11.1g, yield：92.5%).
Gained clear crystal described below1H-NMR modal datas.
1H-NMR(D2O,500MHz)：δ(ppm)=1.18-1.24 (m,9H)、2.01 (m,2H)、2.19-2.26 (m,
6H)、2.37 (m,2H)、3.01-3.04 (t,J=7.1Hz,2H)。
[comparative example 1]
Tri-butylamine 2g (10.8mmol), acetone 5ml are put into in the there-necked flask for possessing condensing tube, Dropping funnel, in stirring
While content, PS 1.32g (10.8mmol) is slowly added at 25 DEG C, after addition terminates, 48 is carried out
The backflow of hour.
After reaction terminates, gained sediment is washed by leaching precipitate with acetone, so as to obtain as object
Tributyl propane sulfonic acid ammonium (receipts amount：1.23g, yield：37.0%).
Gained clear crystal described below1H-NMR modal datas.
1H-NMR(D2O,500MHz)：δ(ppm)=0.90-0.93 (t,J=7.4Hz,9H)、1.30-1.37 (sext,J=
7.4Hz,6H)、1.60-1.67 (m,6H)、2.07-2.14 (m,2H)、2.91-2.93 (t,J=7.1Hz,2H)、3.19-
3.22 (m,6H)、3.34-3.37 (m,2H)。
For the zwitterionic compound obtained in embodiment 1 ~ 2 and comparative example 1, following measure is carried out respectively.
(differential scanning calorimetric analysis)
Using differential scanning calorimetric analysis device (SII Na ノ テ Network ノ ロ ジ ー company systems, DSC7020), in N2Gas flow
Under conditions of being 10 DEG C/min for 40ml/ minutes, programming rate, the amphion chemical combination obtained in making embodiment and comparative example
Thing is warming up to+250 DEG C from -100 DEG C, so as to determine glass transition temperature and fusing point.Show the result in table 1.
(thermogravimetric analysiss)
Using Thermgravimetric Analysis Apparatus (Shimadzu Seisakusho Ltd.'s company system, DTG-60), in N2Gas flow is 100ml/ minutes, heat up speed
Under conditions of spending for 10 DEG C/min, the zwitterionic compound obtained in making embodiment and comparative example is warming up to 600 from 25 DEG C
℃.Temperature when loss of weight ratio is reached 5% is shown in table 1.
(ionic conductance measure)
The zwitterionic compound obtained in making embodiment and comparative example and double (trifluoro methylsulfonyl) imine lithiums are with 1:1 (mol ratio)
Proportioning be dissolved in methanol.By Rotary Evaporators from resulting solution after distillation for removing methanol, by residue under reduced pressure,
It is dried 24 hours at 120 DEG C, so as to obtain lithium ion conductor.
The politef partition for being provided with 300 μ m-thicks in the hole of a diameter of 8mm is glued with biliquid solidified type epoxy resin
It is connected on platinum electrode plate.Then, filled after lithium ion conductor respectively in the hole, overlapped on aforementioned politef partition
Another platinum electrode plate, so as to obtain the measurement sample of the Rotating fields with platinum electrode plate/lithium ion conductor/platinum electrode plate.
Gained measurement sample is assembled in the cell evaluation battery of シ ス テ system company of Japan manufacture, is used
The electric impedance analyzer 1260 of Solartron companies manufacture, in temperature：60 DEG C (without humidified condition), determine frequency：5 ~ 1MHz, apply
Making alive：Impedance is determined under conditions of 100mV.SH-241 of the temperature chamber using the manufacture of エ ス ペ ッ Network company.
Using by resistance value obtained from said determination, ionic conductance is calculated by following formula.
Show the result in table 1.
[mathematical expression 1]
σ：Ionic conductance (S/cm), d：Interelectrode distance (cm), R：Resistance (Ω), S：Sectional area (cm2)。
[table 1]
Herein below as shown in Table 1.
Temperature of the zwitterionic compound of embodiment 1,2 when loss of weight ratio reaches 5% is high, excellent heat resistance.
Additionally, high using the ionic conductance of ion conductor obtained from the zwitterionic compound of embodiment 1,2.
Claims (3)
1. zwitterionic compound, which is shown in following formula (I)s,
[chemical formula 1]
In formula, R1~R3Alkyl, the cycloalkyl that carbon number is 3 ~ 8, carbon number that carbon number is 1 ~ 5 are represented independently of one another
Thiazolinyl or substituted or unsubstituted carbon number for 2 ~ 10 for 6 ~ 20 aryl, X represent carbon number be 2 ~ 5 alkylene
Base.
2. ion conductor, which contains：Zwitterionic compound and the 1st race of the periodic table of elements or the 2nd described in claim 1
The salt of the metal of race.
3. ion conductor according to claim 2, wherein, the salt of the metal is lithium salts.
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| CN115304518A (en) * | 2022-08-03 | 2022-11-08 | 苏州旭珀禾科技有限公司 | Biocompatible zwitterionic compound and preparation method thereof |
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| TW201609957A (en) * | 2014-08-22 | 2016-03-16 | Lintec Corp | Electrolyte composition, secondary battery, and method for using secondary battery |
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| US2828332A (en) * | 1955-08-23 | 1958-03-25 | Monsanto Chemicals | Phosphonium compounds |
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| CN115304518A (en) * | 2022-08-03 | 2022-11-08 | 苏州旭珀禾科技有限公司 | Biocompatible zwitterionic compound and preparation method thereof |
| CN115304518B (en) * | 2022-08-03 | 2023-10-31 | 苏州旭珀禾科技有限公司 | Zwitterionic compound with biocompatibility and preparation method thereof |
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| JPWO2016027785A1 (en) | 2017-04-27 |
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