WO2007063959A1 - P-n結合を含むホスホニウムカチオンを有するイオン液体およびその製造方法 - Google Patents
P-n結合を含むホスホニウムカチオンを有するイオン液体およびその製造方法 Download PDFInfo
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- WO2007063959A1 WO2007063959A1 PCT/JP2006/323983 JP2006323983W WO2007063959A1 WO 2007063959 A1 WO2007063959 A1 WO 2007063959A1 JP 2006323983 W JP2006323983 W JP 2006323983W WO 2007063959 A1 WO2007063959 A1 WO 2007063959A1
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- ionic liquid
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 78
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 title description 12
- 239000007788 liquid Substances 0.000 claims abstract description 44
- 150000001768 cations Chemical class 0.000 claims abstract description 35
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 10
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000003990 capacitor Substances 0.000 claims abstract description 7
- 239000000446 fuel Substances 0.000 claims abstract description 7
- 238000003860 storage Methods 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims description 261
- 239000002904 solvent Substances 0.000 claims description 209
- -1 phosphonium ions Chemical class 0.000 claims description 140
- 125000001424 substituent group Chemical group 0.000 claims description 60
- 125000004432 carbon atom Chemical group C* 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 27
- 229920006395 saturated elastomer Polymers 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 238000000605 extraction Methods 0.000 claims description 15
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 125000004429 atom Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 150000002500 ions Chemical class 0.000 claims description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 239000008151 electrolyte solution Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000010687 lubricating oil Substances 0.000 claims description 3
- 239000004014 plasticizer Substances 0.000 claims description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 238000009713 electroplating Methods 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 230000002152 alkylating effect Effects 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims 1
- 239000007810 chemical reaction solvent Substances 0.000 abstract description 6
- 239000005416 organic matter Substances 0.000 abstract 1
- 238000005481 NMR spectroscopy Methods 0.000 description 269
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 142
- 229910021642 ultra pure water Inorganic materials 0.000 description 118
- 239000012498 ultrapure water Substances 0.000 description 118
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 101
- 239000007983 Tris buffer Substances 0.000 description 86
- 150000001875 compounds Chemical class 0.000 description 74
- 238000002844 melting Methods 0.000 description 74
- 230000008018 melting Effects 0.000 description 74
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 71
- 238000002360 preparation method Methods 0.000 description 70
- 238000001228 spectrum Methods 0.000 description 70
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
- 239000007864 aqueous solution Substances 0.000 description 55
- 238000003756 stirring Methods 0.000 description 54
- 238000005160 1H NMR spectroscopy Methods 0.000 description 51
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 48
- 239000010410 layer Substances 0.000 description 46
- 238000005979 thermal decomposition reaction Methods 0.000 description 37
- 230000004580 weight loss Effects 0.000 description 36
- 238000010438 heat treatment Methods 0.000 description 35
- 238000005259 measurement Methods 0.000 description 32
- 239000000284 extract Substances 0.000 description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 30
- 239000012299 nitrogen atmosphere Substances 0.000 description 30
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 24
- 238000010992 reflux Methods 0.000 description 23
- 239000000203 mixture Substances 0.000 description 22
- 238000001291 vacuum drying Methods 0.000 description 22
- 239000000725 suspension Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- 238000005406 washing Methods 0.000 description 19
- 239000012044 organic layer Substances 0.000 description 17
- 239000013078 crystal Substances 0.000 description 15
- 235000002597 Solanum melongena Nutrition 0.000 description 14
- 230000009477 glass transition Effects 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 238000001816 cooling Methods 0.000 description 13
- 238000002425 crystallisation Methods 0.000 description 13
- 230000008025 crystallization Effects 0.000 description 13
- MQKNLRFUHOJEGN-UHFFFAOYSA-N 3-[14-hydroxy-3-[4-hydroxy-5-[5-[3-hydroxy-5-(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenan Chemical compound O1C(C)C(O)C(OC)CC1OC1C(OC)C(O)C(OC2C(CC(OC2C)OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)CC5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)OC)OC1C MQKNLRFUHOJEGN-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000011085 pressure filtration Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000004821 distillation Methods 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 7
- IRLPACMLTUPBCL-KQYNXXCUSA-N 5'-adenylyl sulfate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](O)[C@H]1O IRLPACMLTUPBCL-KQYNXXCUSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 238000002848 electrochemical method Methods 0.000 description 6
- 239000003792 electrolyte Substances 0.000 description 6
- 229910003473 lithium bis(trifluoromethanesulfonyl)imide Inorganic materials 0.000 description 6
- QSZMZKBZAYQGRS-UHFFFAOYSA-N lithium;bis(trifluoromethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F QSZMZKBZAYQGRS-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 5
- CSCPPACGZOOCGX-MICDWDOJSA-N 1-deuteriopropan-2-one Chemical compound [2H]CC(C)=O CSCPPACGZOOCGX-MICDWDOJSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910013872 LiPF Inorganic materials 0.000 description 4
- 101150058243 Lipf gene Proteins 0.000 description 4
- 241001274216 Naso Species 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002168 alkylating agent Substances 0.000 description 4
- 229940100198 alkylating agent Drugs 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- PBIMIGNDTBRRPI-UHFFFAOYSA-N trifluoro borate Chemical compound FOB(OF)OF PBIMIGNDTBRRPI-UHFFFAOYSA-N 0.000 description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 238000002484 cyclic voltammetry Methods 0.000 description 3
- LMEDOLJKVASKTP-UHFFFAOYSA-N dibutyl sulfate Chemical compound CCCCOS(=O)(=O)OCCCC LMEDOLJKVASKTP-UHFFFAOYSA-N 0.000 description 3
- 125000003963 dichloro group Chemical group Cl* 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- BBBXVLCJTNBOIV-UHFFFAOYSA-N fluoro butane-1-sulfonate Chemical compound CCCCS(=O)(=O)OF BBBXVLCJTNBOIV-UHFFFAOYSA-N 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- KTMXYEHPGMJSMP-UHFFFAOYSA-N trimethylsilylmethylphosphane Chemical compound C[Si](C)(C)CP KTMXYEHPGMJSMP-UHFFFAOYSA-N 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- RZRZGRFVQKHHAY-UHFFFAOYSA-M (dibutylamino)-tris[ethyl(methyl)amino]phosphanium;iodide Chemical compound [I-].CCCCN(CCCC)[P+](N(C)CC)(N(C)CC)N(C)CC RZRZGRFVQKHHAY-UHFFFAOYSA-M 0.000 description 2
- ZJFQLESORYRGMI-UHFFFAOYSA-M (dipentylamino)-tris[ethyl(methyl)amino]phosphanium;iodide Chemical compound [I-].CCCCCN([P+](N(C)CC)(N(C)CC)N(C)CC)CCCCC ZJFQLESORYRGMI-UHFFFAOYSA-M 0.000 description 2
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 2
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 2
- 229910020808 NaBF Inorganic materials 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- HYFRAYLQKCFGLT-UHFFFAOYSA-N O=S(C(F)(F)F)(NS(C(F)(F)F)(=O)=O)=O.P Chemical compound O=S(C(F)(F)F)(NS(C(F)(F)F)(=O)=O)=O.P HYFRAYLQKCFGLT-UHFFFAOYSA-N 0.000 description 2
- JOVQLNOHOLOOEI-UHFFFAOYSA-N OS(=O)(=O)OP(=O)=O Chemical compound OS(=O)(=O)OP(=O)=O JOVQLNOHOLOOEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 150000001347 alkyl bromides Chemical class 0.000 description 2
- 150000001348 alkyl chlorides Chemical class 0.000 description 2
- 150000001351 alkyl iodides Chemical class 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 150000008050 dialkyl sulfates Chemical class 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- TYVVAQMXSKULEC-UHFFFAOYSA-M (dipropylamino)-tris[ethyl(methyl)amino]phosphanium;iodide Chemical compound [I-].CCCN(CCC)[P+](N(C)CC)(N(C)CC)N(C)CC TYVVAQMXSKULEC-UHFFFAOYSA-M 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- BRRVXFOKWJKTGG-UHFFFAOYSA-N 3,3,5-trimethylcyclohexanol Chemical compound CC1CC(O)CC(C)(C)C1 BRRVXFOKWJKTGG-UHFFFAOYSA-N 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- 101710134784 Agnoprotein Proteins 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- 229910018134 Al-Mg Inorganic materials 0.000 description 1
- 229910018131 Al-Mn Inorganic materials 0.000 description 1
- 229910018467 Al—Mg Inorganic materials 0.000 description 1
- 229910018461 Al—Mn Inorganic materials 0.000 description 1
- 229910018575 Al—Ti Inorganic materials 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RZXLPPRPEOUENN-UHFFFAOYSA-N Chlorfenson Chemical compound C1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C=C1 RZXLPPRPEOUENN-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
- 229910013075 LiBF Inorganic materials 0.000 description 1
- 229910012097 LiSbF Inorganic materials 0.000 description 1
- OHQGEMNGEDPZAD-UHFFFAOYSA-N P.CN(CCCNC)C Chemical compound P.CN(CCCNC)C OHQGEMNGEDPZAD-UHFFFAOYSA-N 0.000 description 1
- ZSHAMNFSSLDPHO-UHFFFAOYSA-N P.CN(CCNC)C Chemical compound P.CN(CCNC)C ZSHAMNFSSLDPHO-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 230000000735 allogeneic effect Effects 0.000 description 1
- QQHSIRTYSFLSRM-UHFFFAOYSA-N alumanylidynechromium Chemical compound [Al].[Cr] QQHSIRTYSFLSRM-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- CFFMAHZPZWPANA-UHFFFAOYSA-O bis(trifluoromethylsulfonyl)azanide;2-ethyl-3-methyl-1h-imidazol-3-ium Chemical compound CCC1=NC=C[NH+]1C.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F CFFMAHZPZWPANA-UHFFFAOYSA-O 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- OOCUOKHIVGWCTJ-UHFFFAOYSA-N chloromethyl(trimethyl)silane Chemical compound C[Si](C)(C)CCl OOCUOKHIVGWCTJ-UHFFFAOYSA-N 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([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
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
- UQUPIHHYKUEXQD-UHFFFAOYSA-N n,n′-dimethyl-1,3-propanediamine Chemical compound CNCCCNC UQUPIHHYKUEXQD-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NDAGKNPFXJYVTD-UHFFFAOYSA-N n-phosphanylbutan-1-amine Chemical compound CCCCNP NDAGKNPFXJYVTD-UHFFFAOYSA-N 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- BQWRIOADLPWEPE-UHFFFAOYSA-N oxido-oxo-(sulfooxymethyl)phosphanium Chemical compound C(OS(=O)(=O)O)[P+](=O)[O-] BQWRIOADLPWEPE-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- PZHNNJXWQYFUTD-UHFFFAOYSA-N phosphorus triiodide Chemical compound IP(I)I PZHNNJXWQYFUTD-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- GPNIJXACCBKBEP-UHFFFAOYSA-M silver;2,2,3,3,4,4,4-heptafluorobutanoate Chemical compound [Ag+].[O-]C(=O)C(F)(F)C(F)(F)C(F)(F)F GPNIJXACCBKBEP-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GHEIBVIKGMEDEM-UHFFFAOYSA-M tris[butyl(methyl)amino]-(dibutylamino)phosphanium;iodide Chemical compound [I-].CCCCN(C)[P+](N(C)CCCC)(N(C)CCCC)N(CCCC)CCCC GHEIBVIKGMEDEM-UHFFFAOYSA-M 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 125000005023 xylyl group Chemical group 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
-
- 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
- C07F9/5463—Compounds of the type "quasi-phosphonium", e.g. (C)a-P-(Y)b wherein a+b=4, b>=1 and Y=heteroatom, generally N or O
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
- C07F9/65688—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphonium compound
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- H—ELECTRICITY
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- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/122—Ionic conductors
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- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/20—Conductive material dispersed in non-conductive organic material
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- 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
- H01G11/56—Solid electrolytes, e.g. gels; Additives therein
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- 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
- H01G11/62—Liquid electrolytes characterised by the solute, e.g. salts, anions or cations therein
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- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/004—Details
- H01G9/022—Electrolytes; Absorbents
- H01G9/035—Liquid electrolytes, e.g. impregnating materials
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/04—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof adapted as photovoltaic [PV] conversion devices
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- 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
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- 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
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- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M6/00—Primary cells; Manufacture thereof
- H01M6/14—Cells with non-aqueous electrolyte
- H01M6/16—Cells with non-aqueous electrolyte with organic electrolyte
- H01M6/162—Cells with non-aqueous electrolyte with organic electrolyte characterised by the electrolyte
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- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M6/00—Primary cells; Manufacture thereof
- H01M6/14—Cells with non-aqueous electrolyte
- H01M6/16—Cells with non-aqueous electrolyte with organic electrolyte
- H01M6/162—Cells with non-aqueous electrolyte with organic electrolyte characterised by the electrolyte
- H01M6/166—Cells with non-aqueous electrolyte with organic electrolyte characterised by the electrolyte by the solute
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/077—Ionic Liquids
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
- H01G9/2004—Light-sensitive devices characterised by the electrolyte, e.g. comprising an organic electrolyte
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- H—ELECTRICITY
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- 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
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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
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/542—Dye sensitized solar cells
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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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- 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
- Y02E60/13—Energy storage using capacitors
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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
- 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
Definitions
- the present invention relates to an ionic liquid that exhibits a liquid state in a wide temperature range and is excellent in electrochemical stability, a method for producing the ionic liquid, a power storage device using the ionic liquid, a lithium secondary battery, an electric double layer capacitor,
- the present invention relates to various uses such as dye-sensitized solar cells, fuel cells, and reaction solvents.
- a lithium secondary battery, an electric double layer capacitor, a fuel cell, or a dye has a stable liquid state and a small amount of ionic liquid with excellent electrochemical stability over a wide temperature range. This is a major obstacle for application as an electrolyte, electrolyte or additive for sensitized solar cells or power storage devices.
- Patent Document 1 Japanese Patent Publication No. 2001-517205
- Patent Document 2 Pamphlet of International Publication No. 02Z076924
- Patent Document 3 Japanese Patent Laid-Open No. 2003-331918
- Non-Patent Document 1 Kaji principle, Electrochemistry, 70, No.2, 130 (2002)
- Non-patent literature 2 Y.Katayama, b.Dan, T.Miura and T.Kisni, Journal of The Eiectrocnemical Society, 148 (2), C102— C105 (2001)
- Non-Patent Literature 3 Hajime Matsumoto, Yoshinori Amagasaki, Molten salt and high temperature chemistry, 44, 7 (2001)
- Non-Patent Document 4 H. Matsumoto, M. Yanagida, K. Tanimoto, M. Nomura, Y. Kitagawa and
- Non-Patent Document 5 D.R.MacFarlane, J.Sun, J.Golding, P.Meakin and M.Forsyth, Electrochemica Acta, 45, 1271 (2000)
- Non-Patent Document 6 Doulas R. MacFarlane, Jake Golding, Stewart Forsyth, Maria Forsyth and Glen B. Deacon, Chem. Commun., 1430 (2001)
- An object of the present invention is to provide an ionic liquid that exhibits a stable liquid state in a wide temperature range and is excellent in electrochemical stability, and a method for producing the ionic liquid.
- Ionic liquids that can be used as materials for secondary batteries, electric double layer capacitors, dye-sensitized solar cells, fuel cells, reaction solvents, etc., especially liquids that are stable near room temperature.
- An object of the present invention is to provide an ionic liquid containing a novel phosphonium cation.
- the inventors of the present invention synthesized a large number of salts having a cation component and a cation component, and as a result of earnestly examining an ionic liquid for achieving the above-mentioned object, the present inventors have included at least one PN bond.
- Ri ⁇ R optional substituents of u may form a cyclic structure together.
- the carbon atoms contained in these substituents R ⁇ R 11 are-0-,-Si (R ')-, -C (0)-,-C (0) 0-,-S-,- S (
- R'- ⁇ -, and -P (R ') N- group forces are also replaced by selected atoms and / or groups
- R ′ is a C to C linear or side chain alkyl group, or an F atom
- X 1 , X 2 and X 3 each independently represent an N atom, an O atom, an S atom, or a C atom. However, two of X 1 , X 2 and X 3 are not N atoms.
- R 3 , R 8 or R 11 is a substituent which is present only when X 1 , X 2 or X 3 is a C atom, and when X 1 is a C atom, X 1 , When R 2 and R 3 forces X 2 are C atoms, X 2 , R 6 , R 7 and R 8 forces When X 3 is C atoms, X 3 , R 9 , R 10 and R 11 are Jointly form saturated or partially or fully unsaturated cyclic structures You may make it.
- R 2 , R 7 or R 1G is a substituent which is present only when X 1 , X 2 or X 3 is an N atom or a C atom, and when X 1 is an N atom or a C atom, X 1 , R 1 and R 2, if X 2 is N atom or C atom, X 2, R 6 and R 7, if X 3 is N atom or C atom, X 3, R 9 and R 1C >, respectively may form a ring structure jointly saturated or partially or fully unsaturated. Furthermore, a dotted line shows a conjugate structure.
- the present invention relates to "an ionic liquid containing a phosphonium ion containing one, two or four bonds as a cation component", "an organic substance represented by the general formula (1)”
- An ionic liquid comprising a cation component ”and“ one or a plurality of ionic liquids composed of a cation component and a cation component, wherein the cation component also has the group power of the cation component represented by the general formula (1) ”
- the above object is achieved by providing an “ionic liquid”.
- FIG. 1 is a graph showing a CV curve of methylbutylbis (jetylamino) phosphonium bistrifluoromethane sulfonimide of Example 2.
- FIG. 2 is a graph showing a CV curve of dimethylbutyl (jetylamino) phosphonium bistrifluoromethane sulfonimide of Example 6.
- FIG. 3 is a graph showing a CV curve of tris (jetylamino) di n-butylaminophosphonium bistrifluoromethanesulfurimide of Example 13.
- the substituents R 1 to R U in the general formula (1) are alkyls having a H atom, C to C linear or side chain. Group, saturated or part
- a partially or fully unsaturated cycloalkyl group, aryl group, heterocyclic group, and the H atom contained in one or more substituents of these substituents to 11 is a halogen atom.
- substituents -1 is -0-,-Si (R ')-,-C (O)-,-C (0) 0-,-S-,-S ( O)-, and -NR'- [where R '
- Alkyl groups having straight or side chains from H to C, or partially by F atoms having straight or side chains from H to C, or partially by F atoms
- ⁇ R 11 in the general formula (1) is an alkyl group or an alkoxy each having a linear or side chain of the C -C
- alkynyl group having a chain or a side chain either a saturated or partially or fully unsaturated cycloalkyl group is shown.
- the H atom contained in these substituents R is partially or completely by a halogen atom, or partially by a CN group or NO group.
- Group force Can be substituted by selected atom and Z or atomic group (where R ′ is an alkyl group having a C 1 to C 6 linear or side chain,
- Rf is a fluorine-containing substituent.
- One or more species selected. These key components are present as a stable liquid in a wide temperature range by combining with the cationic component, and can constitute an ionic liquid having excellent electrochemical stability.
- “exists as a stable liquid in a wide temperature range” means that the liquid is near 100 ° C, which is currently defined as a general ionic liquid, and the thermal decomposition temperature is about 200 ° C or higher than the melting point. It means that it exists as a stable liquid in this wide temperature range!
- the combination of the cationic component and these preferred U and ion components it is more preferable than the combination of the cationic component and these preferred U and ion components, and it has a characteristic, that is, an ionic liquid that exhibits a stable liquid in a wide temperature range of low-temperature force and is excellent in electrochemical stability. Can do.
- NO-, F_, Cr, Br_, and the power of the group of cocoons are one or more selected, and
- ionic liquids that are alkyl groups or alkoxy groups ( ⁇ ⁇ 1 may be the same or different from each other! /,).
- ionic liquids having a cation component that, at least one Ri ⁇ R u has a silyl group or a cyclic structure, a linear alkyl group of the remaining force H atom or C ⁇ C cation
- Examples thereof include ionic liquids having an on component.
- X 1 , X 2 and X 3 are C atoms
- R 1 is a propyl group
- R 2 and R 3 are H atoms
- R 4 and R 5 are ethyl groups
- R 6 to R U are A phosphonium cation which is an H atom
- X 1 , X2 and X 3 are N atoms
- R 4 and R 5 Q are ethyl groups
- X 1 , X 2 and X 3 are N atoms
- R 9 is a methyl group
- R 5 and R 1Q are butyl groups
- Examples include a cationium cation, a cation cation in which X 1 , X 2 and X 3 are N atoms
- R 2 is an ethyl group
- R 4 , R 6 and R 9 are methyl
- X 1 , X 2 and X 3 are N atoms
- the melting point of the ionic liquid consisting of SO) N-anion is about 90 ° C, whereas X 1 , X 2 and
- N-ion ionic liquids have a melting point of about 25 ° C. , Symmetrical
- Such a low melting point ionic liquid can be used as an electrolyte alone.
- the ionic liquid of the present invention described above is an ionic liquid that is stable over a wide temperature range and excellent in electrochemical stability. Therefore, the ionic liquid of the present invention is used for an electrolyte, an electrolytic solution or an additive for a power storage device, a lithium secondary battery, an electric double layer capacitor, a fuel cell or a dye-sensitized solar cell, an activator, or a lubricating oil. It is useful as a material used as a reaction solvent for various reactions. Furthermore, since it is stable against strong alkali, it can also be used as a reaction solvent in an alkaline atmosphere. It is known that the use of an ionic liquid in place of a conventionally used plasticizer significantly increases the thermal stability.
- Alkylating agent (R 7 W) is added dropwise to the organic material represented by the general formula (2) or (3) as a raw material, and reacted at a predetermined temperature and time. After washing with ultrapure water or jetyl ether, vacuum dry.
- Alkylating agents (R 7 W) include alkyl iodide, alkyl bromide, alkyl chloride, dialkyl sulfate, sulfonic acid dialkyl ester, carbonic acid dialkyl ester, phosphoric acid trialkyl ester, mono- or polyfluoroalkylsulfonic acid alkyl ester.
- the ionic liquid containing the cation component represented by the general formula (1) containing four P—N bonds is obtained, for example, as follows.
- R 1 R 2 may be used.
- Alkylating agent (RSV and R 2 W) is added dropwise to the organic material represented by the general formula (4) as a raw material, and allowed to react for a predetermined temperature and time. After washing with ultrapure water or jetyl ether, vacuum dry.
- Alkylating agents include alkyl iodide, alkyl bromide, alkyl chloride, dialkyl sulfate, dialkyl ester sulfonate, dialkyl ester carbonate, trialkyl ester phosphate, mono- or poly-fluoride.
- alkyl alkyl sulfonates examples include alkyl alkyl sulfonates, alkyl alkyl perfluorosulfonates, alkyl esters of mono- or polyfluorocarboxylic acids, alkyl alkyl perfluorocarboxylates, alkyl perfluorocarboxylates, sulfuric acid, nitric acid, and hydrochloric acid.
- ionic liquids having different anions can be obtained by exchanging anions by the following method.
- ion-binding compound A + Q_ for example, LiN (CF SO), NaN (CF
- the substituent RR 7 in the general formula (5) and R 2 , R 4 to R 7 , R 9 , R 1Q in the general formula (6) are independent of each other and are the same. May be different. These substituents are each an H atom, a halogen atom, an alkyl group having a C to C linear or side chain.
- Alk having a linear or side chain having a single or multiple double bonds of c to c
- Nyl group having a linear or side chain with a single or multiple triple bond of C to C
- R 1 R 2 , R 4 to R 7 , R 9 and R 1Q may form a cyclic structure together.
- Atoms selected from the group 0) R, -P (0) R, -0-, -0-P (0) R, -0-, and -P (R ') N-
- halogen atom examples include F, Cl, Br and I.
- cycloalkyl group examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclonol, cyclodecyl, and the like.
- the cycloalkyl group includes those having an unsaturated bond such as a cycloalkenyl group and a cycloalkyl group, and may be partially formed by a halogen atom. Can be completely substituted, or can be partially substituted by CN group or NO group.
- heterocyclic group examples include pyrrolidyl, pyrrolinyl, imidazolidinyl, imidazolinyl, pyrarozolidinyl, pyrazonyl, piperidyl, piperazinyl, morpholinyl, and benzyl groups.
- These heterocyclic groups contain one or more alkyl groups, alkoxy groups, hydroxyl groups, carboxyl groups, amino groups, alkylamino groups, dialkylamino groups, thiol groups, alkylthio groups, and halogen atoms. It's good.
- aryl group includes, for example, phenol, talm, mesityl, tolyl, xylyl group and the like (these aryl groups include alkyl group, alkoxy group, hydroxyl group, carboxyl group, acyl group, formyl group).
- a group, an amino group, an alkylamino group, a dialkylamino group, a thiol group, an alkylthio group, and a halogen atom may be contained.
- alkoxyalkyl groups such as methoxymethyl, methoxyethyl, ethoxymethyl and ethoxyethyl
- trialkylsilyl groups such as trimethylsilyl group
- examples of the cation component Q to be combined with the compound represented by the general formula (4) or (5) include the aforementioned cation component.
- the compound was identified by a nuclear magnetic resonance analyzer (BRUKER Ultra Shie Id 300 NMR Spectrometer manufactured by BRUKER). The spectrum data is shown below.
- the compound was identified by a nuclear magnetic resonance analyzer (BRUKER Ultra Shie Id 300 NMR Spectrometer manufactured by BRUKER). The spectrum data is shown below.
- Figure 1 shows the CV curve for methyl n-butylbis (jetylamino) phosphonium bistrifluoromethanesulfonylimide.
- a 50 ml eggplant flask equipped with a magnetic stirrer was charged with 2.00 g (0. 0050 mol) of methyl n-butylbis (jetylamino) phospho-sulfuric acid sulfate obtained in (e) and 10 ml of ultrapure water. While stirring, dissolve LiPF 0.84g (0.0055mol) in 10ml ultrapure water.
- LiTFSI 4.5 g (0.016 mol) was added and stirred at room temperature. Then, it was washed with ultrapure water until it became no turbidity, and the organic phase was concentrated with a rotary evaporator, then washed three times with jetyl ether, and dried at 80 ° C in vacuum. As a white crystal, 0.94 g of 1,1-bis (jetylamino) -3-methyl-3-phosphorhenium bistrifluoromethanesulfoimide was obtained. The yield was 13%.
- the compound was identified by a nuclear magnetic resonance analyzer (BRUKER Ultra Shie Id 300 NMR Spectrometer manufactured by BRUKER). The spectrum data is shown below.
- the compound was identified by a nuclear magnetic resonance analyzer (BRUKER Ultra Shie Id 300 NMR Spectrometer manufactured by BRUKER). The spectrum data is shown below.
- the compound was identified by a nuclear magnetic resonance analyzer (BRUKER Ultra Shie Id 300 NMR Spectrometer manufactured by BRUKER). The spectrum data is shown below.
- the electric conductivity at 25 ° C by the AC impedance method (manufactured by Hokuto Denko Corporation electrochemical measurement system HZ- 3000) was 0. 123Sm _1.
- the aqueous layer was further extracted with 20 ml CH C1. After washing the organic layer with 50 ml of ultrapure water 3 times The extract was concentrated on a rotary evaporator and dried in vacuo at 80 ° C. As a clear liquid, 0.62 g of dimethyl n-butyl (jetylamino) phospho-hexafluorophosphatate was obtained. The yield was 46%.
- a 30 ml eggplant flask equipped with a magnetic stirrer was charged with 0.50 g (0.013 mol) of methyl n-butylbis (jetylamino) phospho-sulfuric acid sulfate obtained in (e) and stirred with lithium.
- a solution prepared by dissolving 0.20 g (0.0013 mol) of trifluorosulfonate in 10 ml of ultrapure water was added, and the mixture was stirred at room temperature for 20 hours. The aqueous layer was removed, washed 3 times with ultrapure water, and then vacuum dried at 80 ° C.
- the melting point was measured with a scanning differential calorimeter (DSC8230, manufactured by Shimadzu Corporation). As a result, the melting point was 74.8 ° C and the crystallization temperature was 56.4 ° C.
- the thermal decomposition temperature was measured with a thermogravimetric analyzer (TG8120, manufactured by Rigaku Corporation). The 5% weight loss temperature measured at a heating rate of 10 ° C Zmin was 311.8 ° C.
- the thermal decomposition temperature according to 0) was measured.
- the 5% weight loss temperature measured at a heating rate of 10 ° CZmin is 328.8. C.
- the 2 2 2 2 layer was washed 3 times with 20 ml of ultrapure water, and then the extract was concentrated on a rotary evaporator and dried in vacuo at 80 ° C.
- a yellow transparent liquid 1.OOg of methyl n-butyl (N, N'-dimethyl-1,3-propylenediamine) phospho-umbis trifluoromethanesulfurimide was obtained.
- the yield was 76%.
- the melting point was measured with a scanning differential calorimeter (DSC8230, manufactured by Shimadzu Corporation). The melting point was 36.2 ° C, and the crystallization temperature was -24.6 ° C.
- the thermal decomposition temperature was measured with a thermogravimetric analyzer (TG81 20 manufactured by Rigaku Corporation). The 5% weight loss temperature measured at a heating rate of 10 ° CZmin is 285.5. C.
- the aqueous layer was further extracted with 50 ml CH C1. After washing the organic layer 3 times with 100 ml of ultrapure water The extract was concentrated on a rotary evaporator and dried in vacuo at 80 ° C. As a transparent liquid, 2.94 g of dimethyl (N-methylethylamino) n-butoxyphospho- umbistrifluoromethanesulfurimide was obtained. The yield was 83%.
- the effluent was concentrated on a rotary evaporator and dried in vacuo at 90 ° C.
- the yield was 4.55 g and the yield was 34.7%.
- the compound was identified by a nuclear magnetic resonance analyzer (BRUKER Ultra Shie Id 300 NMR Spectrometer manufactured by BRUKER). It was done in. The spectrum data is shown below.
- reaction product separated into two layers was extracted with 50 ml of CH C1, and the aqueous layer was further extracted.
- the extract was concentrated on a rotary evaporator and dried in vacuo at 90 ° C. Thereafter, it was passed through an alumina column (developing solvent CH C1). Again, concentrate the extract with a rotary evaporator.
- the aqueous layer was further extracted with 50 ml CH C1. After washing 5 times with ultra pure water,
- Fig. 3 shows the CV curve of tris (jetylamino) di n-butylaminophospho- umbistrifluoromethanesulfurimide.
- Tris (jetylamino) n-butylaminophospho-muum iodide obtained in B (h) was dissolved in 20 ml of CH CI, and 0.887 g of AgNO was dissolved therein.
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JP2007548007A JP5265197B2 (ja) | 2005-12-02 | 2006-11-30 | P−n結合を含むホスホニウムカチオンを有するイオン液体およびその製造方法 |
CN2006800437036A CN101312983B (zh) | 2005-12-02 | 2006-11-30 | 具有含p-n键的鏻阳离子的离子液体及其制备方法 |
US12/094,766 US8871974B2 (en) | 2005-12-02 | 2006-11-30 | Ionic liquid containing phosphonium cation having P—N bond and method for producing same |
CA2630785A CA2630785C (en) | 2005-12-02 | 2006-11-30 | Ionic liquid containing phosphonium cation having p-n bond and method for producing same |
EP06833786.4A EP1956026B1 (en) | 2005-12-02 | 2006-11-30 | Ionic liquid containing phosphonium cation having p-n bond and method for producing same |
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US20180069265A1 (en) | 2016-08-30 | 2018-03-08 | Wildcat Discovery Technologies, Inc | Electrolyte formulations for electrochemical cells containing a silicon electrode |
US11322778B2 (en) | 2018-05-29 | 2022-05-03 | Wildcat Discovery Technologies, Inc. | High voltage electrolyte additives |
CN110016378B (zh) * | 2019-04-19 | 2022-03-29 | 中国人民解放军联勤保障部队军需能源质量监督总站成都质量监督站 | 一种新型离子液体润滑膜的制备方法 |
JP2023105681A (ja) * | 2022-01-19 | 2023-07-31 | 東京エレクトロン株式会社 | 基板処理方法及びイオン液体 |
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US8871974B2 (en) | 2014-10-28 |
RU2008120238A (ru) | 2009-11-27 |
EP1956026A1 (en) | 2008-08-13 |
JP5265197B2 (ja) | 2013-08-14 |
EP1956026B1 (en) | 2016-11-30 |
RU2409584C2 (ru) | 2011-01-20 |
CN101312983B (zh) | 2013-01-02 |
KR101000247B1 (ko) | 2010-12-10 |
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