JP5753073B2 - ホウ素又はアルミニウム錯体 - Google Patents
ホウ素又はアルミニウム錯体 Download PDFInfo
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- JP5753073B2 JP5753073B2 JP2011500257A JP2011500257A JP5753073B2 JP 5753073 B2 JP5753073 B2 JP 5753073B2 JP 2011500257 A JP2011500257 A JP 2011500257A JP 2011500257 A JP2011500257 A JP 2011500257A JP 5753073 B2 JP5753073 B2 JP 5753073B2
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- 229910052782 aluminium Inorganic materials 0.000 title claims description 76
- 229910052796 boron Inorganic materials 0.000 title claims description 64
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 title claims description 60
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims description 55
- -1 alkali metal cation Chemical class 0.000 claims description 102
- 150000001875 compounds Chemical class 0.000 claims description 79
- 150000003839 salts Chemical class 0.000 claims description 78
- 150000001450 anions Chemical class 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 37
- 239000007787 solid Substances 0.000 claims description 34
- 229910052783 alkali metal Inorganic materials 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 229910004013 NO 2 Inorganic materials 0.000 claims description 20
- 229910052744 lithium Inorganic materials 0.000 claims description 19
- 150000001768 cations Chemical class 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 229920000642 polymer Polymers 0.000 claims description 15
- 239000003792 electrolyte Substances 0.000 claims description 14
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 150000002484 inorganic compounds Chemical class 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 229910010272 inorganic material Inorganic materials 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 150000002892 organic cations Chemical class 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000007983 Tris buffer Substances 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 5
- 238000011065 in-situ storage Methods 0.000 claims description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical group [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical group [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 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-O Pyrazolium Chemical compound C1=CN[NH+]=C1 WTKZEGDFNFYCGP-UHFFFAOYSA-O 0.000 claims description 2
- 125000000909 amidinium group Chemical group 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052746 lanthanum Inorganic materials 0.000 claims description 2
- BWOROQSFKKODDR-UHFFFAOYSA-N oxobismuth;hydrochloride Chemical compound Cl.[Bi]=O BWOROQSFKKODDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002577 pseudohalo group Chemical group 0.000 claims description 2
- GRTBAGCGDOYUBE-UHFFFAOYSA-N yttrium(3+) Chemical compound [Y+3] GRTBAGCGDOYUBE-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 229910014033 C-OH Inorganic materials 0.000 claims 1
- 229910014570 C—OH Inorganic materials 0.000 claims 1
- 125000003367 polycyclic group Chemical group 0.000 claims 1
- 235000021419 vinegar Nutrition 0.000 claims 1
- 239000000052 vinegar Substances 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 168
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 141
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 122
- 238000006243 chemical reaction Methods 0.000 description 106
- 239000000243 solution Substances 0.000 description 93
- 239000002243 precursor Substances 0.000 description 75
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- 239000011698 potassium fluoride Substances 0.000 description 66
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 61
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
- 239000000203 mixture Substances 0.000 description 53
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 239000002904 solvent Substances 0.000 description 37
- 239000002244 precipitate Substances 0.000 description 35
- 238000001704 evaporation Methods 0.000 description 34
- 239000011734 sodium Substances 0.000 description 33
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 32
- 239000000460 chlorine Substances 0.000 description 32
- 230000008020 evaporation Effects 0.000 description 31
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 30
- 239000011775 sodium fluoride Substances 0.000 description 30
- 235000013024 sodium fluoride Nutrition 0.000 description 30
- 238000003756 stirring Methods 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
- 239000002585 base Substances 0.000 description 26
- 239000002253 acid Substances 0.000 description 25
- 239000000725 suspension Substances 0.000 description 25
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 22
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 21
- 239000004327 boric acid Substances 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 17
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 17
- 150000001340 alkali metals Chemical class 0.000 description 16
- 239000011780 sodium chloride Substances 0.000 description 15
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 229910018071 Li 2 O 2 Inorganic materials 0.000 description 13
- 239000011575 calcium Substances 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 13
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 13
- 230000000269 nucleophilic effect Effects 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 229930040373 Paraformaldehyde Natural products 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- 239000000010 aprotic solvent Substances 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 12
- 229920002866 paraformaldehyde Polymers 0.000 description 12
- 239000003880 polar aprotic solvent Substances 0.000 description 12
- 239000002798 polar solvent Substances 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 description 11
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 11
- 235000003270 potassium fluoride Nutrition 0.000 description 11
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 11
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229910018068 Li 2 O Inorganic materials 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 10
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 150000001638 boron Chemical class 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 9
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 9
- 229910016569 AlF 3 Inorganic materials 0.000 description 8
- 0 CC(*[C@]1**)(**1=*C)C(*)(*)* Chemical compound CC(*[C@]1**)(**1=*C)C(*)(*)* 0.000 description 8
- 229910010082 LiAlH Inorganic materials 0.000 description 8
- 230000009471 action Effects 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 8
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 8
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 8
- 239000008139 complexing agent Substances 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 7
- 238000005119 centrifugation Methods 0.000 description 7
- 150000004985 diamines Chemical class 0.000 description 7
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 125000001153 fluoro group Chemical group F* 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 239000002608 ionic liquid Substances 0.000 description 7
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 7
- 239000012429 reaction media Substances 0.000 description 7
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 7
- TXRVDQMSXQKAPG-UHFFFAOYSA-N 2,3,5,6-tetrachlorobenzene-1,4-dicarbonitrile Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(Cl)=C1C#N TXRVDQMSXQKAPG-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 159000000007 calcium salts Chemical class 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- JVYDLYGCSIHCMR-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanoic acid Chemical compound CCC(CO)(CO)C(O)=O JVYDLYGCSIHCMR-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 5
- 239000002841 Lewis acid Substances 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 125000005234 alkyl aluminium group Chemical group 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000000536 complexating effect Effects 0.000 description 5
- 239000002131 composite material Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 5
- 150000007517 lewis acids Chemical class 0.000 description 5
- 229910003002 lithium salt Inorganic materials 0.000 description 5
- 159000000002 lithium salts Chemical class 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 4
- PCRSJGWFEMHHEW-UHFFFAOYSA-N 2,3,5,6-tetrafluorobenzene-1,4-dicarbonitrile Chemical compound FC1=C(F)C(C#N)=C(F)C(F)=C1C#N PCRSJGWFEMHHEW-UHFFFAOYSA-N 0.000 description 4
- UFYGUTCPFMPGMP-UHFFFAOYSA-N 2-propan-2-ylpropanedinitrile Chemical compound CC(C)C(C#N)C#N UFYGUTCPFMPGMP-UHFFFAOYSA-N 0.000 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- GBUDUCWUAWUSEV-UHFFFAOYSA-K [B+3].CC([O-])=O.CC([O-])=O.CC([O-])=O Chemical compound [B+3].CC([O-])=O.CC([O-])=O.CC([O-])=O GBUDUCWUAWUSEV-UHFFFAOYSA-K 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- UPQZOUHVTJNGFK-UHFFFAOYSA-N diethyl 2-methylpropanedioate Chemical compound CCOC(=O)C(C)C(=O)OCC UPQZOUHVTJNGFK-UHFFFAOYSA-N 0.000 description 4
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 150000002222 fluorine compounds Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- PFPYHYZFFJJQFD-UHFFFAOYSA-N oxalic anhydride Chemical compound O=C1OC1=O PFPYHYZFFJJQFD-UHFFFAOYSA-N 0.000 description 4
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 4
- 239000004810 polytetrafluoroethylene Substances 0.000 description 4
- 239000003586 protic polar solvent Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- YRRQOFSSQAOHKE-UHFFFAOYSA-N triethyl 1-methylethane-1,1,2-tricarboxylate Chemical compound CCOC(=O)CC(C)(C(=O)OCC)C(=O)OCC YRRQOFSSQAOHKE-UHFFFAOYSA-N 0.000 description 4
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 4
- 150000004072 triols Chemical class 0.000 description 4
- SCZNXLWKYFICFV-UHFFFAOYSA-N 1,2,3,4,5,7,8,9-octahydropyrido[1,2-b]diazepine Chemical compound C1CCCNN2CCCC=C21 SCZNXLWKYFICFV-UHFFFAOYSA-N 0.000 description 3
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- DIOVHILRQBNIJR-UHFFFAOYSA-N 1h-pyrrole-2,3,4,5-tetracarbonitrile Chemical compound N#CC=1NC(C#N)=C(C#N)C=1C#N DIOVHILRQBNIJR-UHFFFAOYSA-N 0.000 description 3
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- 238000006479 redox reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- RVZHUQPIBHMAEX-UHFFFAOYSA-N sodium;isocyanate Chemical compound [Na+].[N-]=C=O RVZHUQPIBHMAEX-UHFFFAOYSA-N 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical class CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 description 1
- HRTKQUHFGZFPPF-UHFFFAOYSA-M tetraethylazanium;fluoride;dihydrate Chemical compound O.O.[F-].CC[N+](CC)(CC)CC HRTKQUHFGZFPPF-UHFFFAOYSA-M 0.000 description 1
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- CAYKLJBSARHIDI-UHFFFAOYSA-K trichloroalumane;hydrate Chemical compound O.Cl[Al](Cl)Cl CAYKLJBSARHIDI-UHFFFAOYSA-K 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- HNUUNXXLZGBZIR-UHFFFAOYSA-N triethyl hexane-1,2,2-tricarboxylate Chemical compound CCCCC(C(=O)OCC)(C(=O)OCC)CC(=O)OCC HNUUNXXLZGBZIR-UHFFFAOYSA-N 0.000 description 1
- ARUIMKUOHIINGI-UHFFFAOYSA-N trifluoro(methylsulfonyl)methane Chemical compound CS(=O)(=O)C(F)(F)F ARUIMKUOHIINGI-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical class C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
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- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
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- C—CHEMISTRY; METALLURGY
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
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- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages
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- 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
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- H01M10/052—Li-accumulators
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- 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
- H01M10/0567—Liquid materials characterised by the additives
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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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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
R1はR、RF、NO2、CN、C(=O)OR、RSO2又はRFSO2を表わし;
−X1−、−X2−、−X3−及びX4基は互いに独立してそれぞれ>C=O、>C=NC≡N、>C=C(C≡N)2、>CR2R3又は>SO2二価基を表わし;
−Y1−、−Y2−及び−Y3−基は互いに独立してそれぞれ−O−、>N(C≡N)、>N(CORF)、>N(SO2R4)、>NR4、>N(COR4)又は>N(SO2RF)二価基を表わし;
R、R2及びR3は互いに独立してそれぞれH、アルキル基、アリール基、アルキルアリール基、アリールアルキル基、オキサアルキル基又はアルケニル基を表わし;
R4はアルキル基、アリール基、アルキルアリール基、ヘテロアリール基、アリールアルキル基、オキサアルキル基、アルケニル基又はRFCH2−基を表わし;
RFはペルフルオロアルキル基若しくは一部フッ素化アルキル基(水素原子の少なくとも60%がフッ素原子で置換されているのが好ましい)、好ましくは1〜8個の炭素原子を有するもの、又は一部若しくは完全フッ素化フェニル基を表わし;
R'2及びR'3基はそれぞれR又はFを表わし;
複数のR又はRF基が互いに結合してオリゴマー又はポリマーのセグメントを形成することもでき;
ID及びIID錯体において−X1−、−X2−及び−X3−の内の2個の基がそれぞれ>C=Oを表わす場合には、3つ目の基は>CR2R3基を表わし;
IB錯体(Dがホウ素BであるID錯体)においてX1、X2及びX3基がそれぞれCH2基であり且つY基がそれぞれOである場合には、R1はCH3以外である。]
「X基」とは集合的に基X1、X2、X3及びX4を指し、「Xi」基は基X1、X2、X3及びX4の内の任意のものを指し;
「Y基」とは集合的に基Y1、Y2及びY3を指し、「Yi」基はY基の内の任意のものを指す:
ものとする。
・窒素原子を含有するY基の特別な選択;
・X基及び/又はR基の選択;
・窒素原子を含有するY基の数:
によって調節することができる。
・アルミニウムアルコキシドAl(OR6)3(ここで、R6はアルキル基であり、このアルキル基は、これらのアルコキシドの重合度を抑制してそれらの溶解性及び反応性を促進するために分岐鎖状のものであるのが好ましい);
・化合物AR7 3(ここで、R7は好ましくはエチル、プロピル、ブチル、イソブチル、アミル、イソアミル、ヘキシル又はオクチル基(アルキルアルミニウム)又はフェニル基(アリールアルミニウム)である);
・ジアルキルアミドアルミニウムAl(NR8 2)3(ここで、R8はアルキル基、好ましくはCH3又はC2H5である;
・ハロゲン化アルミニウム、好ましくはAlCl3、AlF3又はAlBr3;
・水酸化アルミニウム。
・ペルフルオロアルカンスルホン酸カリウムKRFSO2とメチル化剤、例えばトルエンスルホン酸メチルCH3C6H4SO3CH3との反応;
・立体障害強塩基の存在下におけるスルホンRFSO2CH3とアルデヒドとの反応。
・極性プロトン性溶媒中、例えば低級アルコール中、又はアセトニトリル等の極性非プロトン性溶媒中のホウ酸アルキルと反応させることによって、IB−a2錯体を与えることができ、
・アルミニウムアルコキシド、アルキルアルミニウム又はジアミノアルキルアルミニウムと反応させることによって、IAl−a2アルミニウム錯体を形成することができ、アルコキシドが好ましい。
・極性溶媒中、例えば1〜4個の炭素原子を有するアルコール中でホウ酸アルキル又はホウ酸と反応させることによって、ホウ素錯体を形成することができ;
・アルミニウムアルコキシド、アルキルアルミニウム又はジアミノアルキルアルミニウムと反応させることによって、IAl−a3アルミニウム錯体を形成することができ、アルコキシドが好ましい。
・−C(NCN)OH基を脱離することが意図される酸の存在下でホウ酸アルキル又はホウ酸のようなホウ素源と反応させることによって、IB−a4錯体を形成することができ;
・−C(NCN)OH基を脱離することができる酸を添加した後にアルミニウムアルコキシド又は水酸化アルミニウムと反応させることによって、アルミニウム錯体IAl−a4を形成することができ;また、
・2当量の塩基Nuの存在下でAlCl3、AlBr3、AlF3又はAl2(SO4)3と反応させることによって、IAl−a4アルミニウム錯体を形成することができる[ここで、NuはNuH+X-(Xはアルミニウム塩によって最初に提供されるアニオンの1つを表わす)を形成することによってアルコールタイプの水酸化物が2つの結合−CR1R2O−Alを形成することを可能にする塩基である]。
・R1C(CH2OH)2(CO2Me)又はR1C(CH2OH)2(CO2Et)を得るためのR1C(CH2OH)2(CO2H)のエステル化;
・R1C(CH2OH)2[C(NCN)OM1]を形成させるための塩M1HNCNの作用(ここで、Mは例えばアルカリ金属である)。
・2個のC(NCN)OH基を遊離させるための2当量の酸の存在下でホウ酸アルキル又はホウ酸のようなホウ素源と反応させることによって、錯体IB−a5を形成することができ;
・−C(NCN)OHを遊離させることができる酸を添加した後にアルミニウムアルコキシド又は水酸化アルミニウムと反応させることによって、アルミニウム錯体IAl−a5を形成することができ;
・2当量の塩基Nuの存在下でAlCl3、AlBr3、AlF3又はAl2(SO4)3と反応させることによって、IAl−a5アルミニウム錯体を形成することができる[ここで、NuはNuH+X-(Xはアルミニウム塩によって最初に提供されるアニオンの1つを表わす)を形成することによってアルコールタイプの水酸化物が2つの結合−CR1R2O−Alを形成することを可能にする塩基である]。
・3当量の酸の存在下でホウ酸アルキル若しくはホウ酸のようなホウ素源と反応させることによって、又はBF3若しくはBCl3のようなハロゲン化ホウ素を作用させることによって、又は三酢酸ホウ素B(CH3CO2)3を作用させることによって、錯体IB−a6を形成し;
・≡C(NCN)OHを遊離させることができる酸を添加した後にアルミニウムアルコキシド又は水酸化アルミニウムと反応させることによって、アルミニウム錯体IAl−a6を形成し、或は
・AlCl3、AlBr3、AlF3又はAl2(SO4)3と反応させることによって、対応するM1塩の沈殿を得て、アルミニウム錯体IAl−a6を形成する。
・−C[C(CN)2]OH基を遊離させるための1当量の酸の存在下でホウ酸アルキル又はホウ素のようなホウ素源と反応させることによって、錯体IB−a7を形成することができ;
・−C(NCN)OHを遊離させることができる酸を添加した後に、アルミニウムアルコキシド又は水酸化アルミニウムと反応させることによって、アルミニウム錯体IAl−a7を形成することができ;或は
・2当量の塩基Nuの存在下でAlCl3、AlBr3、AlF3又はAl2(SO4)3と反応させることによってIAl−a7アルミニウム錯体を形成することができる[ここで、NuはNuH+X-(Xはアルミニウム塩によって最初に提供されるアニオンの1つを表わす)を形成することによってアルコールタイプの水酸化物が2つの結合−CR1R2O−Alを形成することを可能にする塩基である]。
・2個の−C[C(CN)2OH]基を遊離させるための2当量の酸の存在下でホウ酸アルキル又はホウ素のようなホウ素源と反応させることによって、錯体IB−a8を形成することができ、前記の酸のアニオン及びカチオンMは、本発明の付加物を生成させるために随意に用いることができるものであり;
・−C(NCN)OHを遊離させることができる酸を添加した後にアルミニウムアルコキシド又は水酸化アルミニウムと反応させることによって、アルミニウム錯体IAl−a8を形成することができ;或は
・2当量の塩基Nuの存在下でAlCl3、AlBr3、AlF3又はAl2(SO4)3と反応させることによってIAl−a8アルミニウム錯体を形成することができる[ここで、NuはNuH+X-(Xはアルミニウム塩によって最初に提供されるアニオンの1つを表わす)を形成することによってアルコールタイプの水酸化物が2つの結合−CR1R2O−Alを形成することを可能にする塩基である]。
・3個の−C[C(CN)2OHを遊離させるための3当量の酸の存在下でホウ酸アルキル若しくはホウ酸のようなホウ素源と反応させることによって、錯体IB−a9を得ることができ、後者はまた、BF3若しくはBCl3のようなハロゲン化ホウ素又は三酢酸ホウ素B(CH3CO2)3を作用させることによって得ることもでき;
・−C(NCN)OHを遊離させることができる酸を添加した後にアルミニウムアルコキシド又は水酸化アルミニウムと反応させることによって、アルミニウム錯体IAl−a9を形成することができ;或は
・AlCl3、AlBr3、AlF3又はAl2(SO4)3と反応させることによって、対応するM1塩の沈殿を得て、アルミニウム錯体IAl−a9を形成することができる。
・低炭素原子数のアルコール、アセトニトリル、アセトン又はTHFのような溶媒中でホウ酸アルキルと反応させることによってIB−b1錯体を与えることができ;
・アルミニウムアルコキシド、アルキルアルミニウム、トリス(ジアルキル)アルミニウム又は水酸化アルミニウムと反応させることによってアルミニウム錯体IAl−b1を形成することができ;又は
・3当量の塩基Nuの存在下でAlCl3、AlBr3、AlF3又はAl2(SO4)3と反応させることによって、IAl−b1アルミニウム錯体を形成することができる(ここで、Nuは2つの結合−CH2−N(COCF3)−Alの形成を可能にする塩基である)。
・W. Stetter及びH. Bockmannによって報告された方法(Chemische Berichte, (1951), 84 834-9)に従った次式:
・THF中でのLiHとCF3CONH2との反応;
・水素を排出させた後の周囲温度におけるCH3C(CH2OSO2C6H4CH3)3の添加。
・非プロトン性溶媒中でホウ酸アルキルと接触させることによって、IB−b1タイプのホウ素錯体を得ることができ;
・アルミニウム源と接触させることによって、IAl−b1タイプのアルミニウム錯体を得ることができる。
に相当し、様々有機前駆体から得ることができ、有機前駆体をホウ素源(例えばホウ酸又はそのエステル)と反応させることによってIB−b3錯体が得られ、アルミニウム源と反応させることによってIAl−b3錯体が得られる。
・J. Dunhamらによって発表された方法[Synthesis, (2006), 680-686]により、ホウ水素化ナトリウムNaBH4をアルデヒドO=CHR1とマロノニトリルとの混合物と反応させることによる、アルキルマロノニトリルR1HC(CN)2の調製;
・R1C(CHR2OH)(CN)2(ここで、R2は上に与えた定義を有する)を得るための、DBUのような強塩基を触媒として用いたアルキルマロノニトリルR1HC(CN)2とアルデヒドO=CHR2との反応;
・ジアミンHOCH2C(R1)(CH2NHR2)2を得るためのR1C(CHR2OH)(CN)2とLiAlH4との反応、又は水素による還元。
・トリス(ヒドロキシメチル)アルカン(その2個のOHが例えばカーボネートの形で保護されたもの)とOHを脱離基に置き換える試薬との反応(R13はCl-、Br-、I-又はR''SO3を表わす)、及びガブリエル反応(例えばビス(ホルミル)イミドのアルカリ金属塩に対するもの)、
・アミノジオールを得るためのカーボネート及びホルミル結合の加水分解、
・トリフルオロアセチル基をアミンに結合させるためのCF3COOC2H5との反応。
・アルキルマロノニトリルR1HC(CN)2をメタノール源H2C=Oによってヒドロキシメチル化し;
・得られたヒドロキシメチル化モノアルキルマロノニトリルをH又はLiAlH4によって還元してジアミノアルコールを得て;
・このジアミノアルコールを、N−シアノイミダゾール(2当量)(これ自体は、CNBrとイミダゾールとの反応によってその場で得られる)と反応させる。
・化合物R1C(CH2OH)2[CH2R13](ここで、R13はCl-、Br-、I-又はR''SO3を表わす)を調製する;
・化合物R1C(CH2OH)2[CH2R13]と化合物MJ(ここで、JはアニオンR''SO2NH-を表わし、Mはアルカリ金属カチオン又はオニウムカチオンであり、このオニウムカチオンは、アミドR''SO2NH2と第3級塩基とを接触させることによって得られるカチオンである)と反応させる。
・X4は>C=O、>C=NCN又は>C=C(CN)2、>SO2又は>C=Sを表わす;
・Lは脱離基、例えばCl、Br、又はイミダゾリル、トリアゾリル若しくはスクシンイミジル基基を表わす。LがCl又はBrである場合には、塩基Nuを加えて除去が容易なNuH+Cl-又はNuH+Nu-を形成させるのが有利である;
・R'2、R'3及びX3は上で与えた意味を持つ;
・P1及びP2はそれぞれ、セグメントX1Y1及びX2Y2の前駆体基、例えばプロトン化された形X1Y1H及びX2Y2Hを表わす。
・リチウム金属箔(厚さ200μm、直径1.8cmのもの)から成るアノード;
・カーボンブラック48重量%、ジリチウムフタロシアニン2重量%、カーボンナノチューブ10重量%及びポリテトラフルオロエチレン(PTFE)ラテックス30重量%をエチレン/プロピレンランダムコポリマー(10%)をバインダーとして含有する多孔質複合材料から成るアノード(この複合材料は、シクロヘキサン中の溶液を用いて、Exmet(登録商標)拡張アルミニウムから作られたコレクター上に塗布される);
・N−メチル−N−プロピルピロリジニウム(MePrPy)+のビス(フルオロスルホンイミド)塩[(FSO2)2N]-に0.3MのIB−19ホウ素錯体が加えられて成るイオン性液体中のLi[(CF3SO2)2N]の0.8M溶液を含浸させたセパレータ(前記ホウ素錯体は、空気電極において酸素還元の生成物との錯体を形成させることが意図される):
を用いて、リチウム−空気バッテリーを製造した。
・「ブランク」の欄には、印●で溶媒の導電性を与え、
・「B」の欄には、印△(中を黒塗りしたもの。以下同じ。)にホウ素錯体の1M溶液の導電性を与え、
・LiFの欄には、印▽(中を黒塗りしたもの。以下同じ。)にLiFを飽和させた溶液の導電性、そして印◆にLiFを飽和させた1M錯体溶液の導電性を与え、
・NaFの欄には、印▽にNaFを飽和させた溶液の導電性、そして印◆にNaFを飽和させた1M錯体溶液の導電性を与え、
・KFの欄には、印▽にKFを飽和させた溶液の導電性、印◆にKFを飽和させた1M錯体溶液の導電性、そして印
にKFとアルミ錯体との付加物の1M溶液の導電性を与え、
・Li2Oの欄には、印▽にLi2Oを飽和させた溶液の導電性、そして印◆にLi2Oを飽和させた1M錯体溶液の導電性を与え、
・Li2O2の欄には、印▽にLi2O2を飽和させた溶液の導電性、そして印◆にLi2O2を飽和させた1M錯体溶液の導電性を与える。
・次の反応に従って触媒塩基(テトラメチルグアニジン)の存在下で商品として入手できるシアノ酢酸エチルを2当量のパラホルムアルデヒドで処理:
Claims (18)
- 次の一般式の1つに相当する多環式錯体。
(ここで、
Dはホウ素B又はアルミニウムAlを表わし;
R1はR、RF、NO2、CN、C(=O)OR、RSO2又はRFSO2を表わし;
−X1−、−X2−、−X3−及びX4基は互いに独立してそれぞれ>C=O、>C=NC≡N、>C=C(C≡N)2、>CR2R3又は>SO2二価基を表わし;
−Y1−、−Y2−及び−Y3−は互いに独立してそれぞれ−O−、>N(C≡N)、>N(CORF)、>N(SO2R4)、>NR4、>N(COR4)又は>N(SO2RF)二価基を表わし;
R、R2及びR3は互いに独立してそれぞれH、アルキル基、アリール基、アルキルアリール基、アリールアルキル基、オキサアルキル基又はアルケニル基を表わし;
R4はアルキル基、アリール基、アルキルアリール基、ヘテロアリール基、アリールアルキル基、オキサアルキル基、アルケニル基又はRFCH2−基を表わし;
RFはペルフルオロアルキル基若しくは一部フッ素化アルキル基、又は一部若しくは完全フッ素化フェニル基を表わし;
R'2及びR'3基はそれぞれR又はFを表わし;
複数のR又はRF基が互いに結合してオリゴマー又はポリマーのセグメントを形成することもでき;
X1、X2及びX3基がそれぞれCH2基である場合、Y基は>N(SO2CF3)、>N(COCF3)、>N(SO2R)、>N(C≡N)及び>NR4(ここで、R4はCN、NO 2 、CF 3 、OCF 3 から選択される少なくとも1個の電子求引性基を有するアリール若しくはヘテロアリールである)基から選択され、且つ/又はR1基はRFSO2−、NO2、RSO2−、−CN及び−C(=O)ORから選択され;
ID及びIID錯体において−X1−、−X2−及び−X3−の内の2個の基がそれぞれ>C=Oを表わす場合には、3つ目の基は>CR2R3基を表わす。) - Y1、Y2及びY3基のそれぞれがOを表わすことを特徴とする、請求項1に記載の錯体。
- Y1、Y2及びY3基の少なくとも1つがNR4を表わすことを特徴とする、請求項1に記載の錯体。
- R1がRFSO2−、NO2、RSO2−、−CN及び−C(=O)ORから選択され、且つ/又は−X1−、−X2−及び−X3−及び存在する場合に−X4−基の内の少なくとも1つが>C=O、>C=NC≡N、>C=C(C≡N)2及びSO2から選択される基を表わし、−X1−、−X2−及び−X3−基の内の1つだけがSO2であることを特徴とする、請求項2に記載の錯体。
- −X1−、−X2−及び−X3−及び存在する場合に−X4−基の少なくとも1つが>C=O、>C=NC≡N及び>C=C(C≡N)2から選択される基を表わすことを特徴とする、請求項3に記載の錯体。
- −X1−、−X2−及び−X3−及び存在する場合に−X4−基がそれぞれCR2R3基を表わすことを特徴とする、請求項1に記載の錯体。
- Y1、Y2及びY3基の少なくとも1つがN(C≡N)、>N(CORF)、>N(SO2R4)、>N(COR4)、>N(SO2RF)又は>NR4基(ここで、R4はCN、NO 2 、CF 3 、OCF 3 から選択される少なくとも1個の電子求引性基を有するアリール若しくはヘテロアリールである)から選択され、且つ/又はR1基がRFSO2−、NO2、RSO2−、−CN及び−C(=O)ORから選択されることを特徴とする、請求項1に記載の錯体。
- 請求項1〜7のいずれかに記載の錯体と塩Mz'Z'm(ここで、Mは原子価nが1〜3であるカチオンであり、Z'は原子価z'が1又は2であるアニオンである)とによって構成された付加物。
- Z'がアニオンF-、Cl-、Br-、OCN-、O2 ・-、OH-、RO-、N3 -、CN-、[O2-M'+]-、[O2 2-M'+]-及び[NCN2-M'+](ここで、M'はH又は一価カチオンである)から選択される一価アニオンであることを特徴とする、請求項8に記載の付加物。
- Z'がアニオンO2-、O2 2-、S2-、S2 2-及びNCN2-から選択される二価アニオンであることを特徴とする、請求項8に記載の付加物。
- Mがアルカリ金属カチオン、アルカリ土類金属カチオン、Ag+、Pb2+、イットリウムカチオン、ランタンカチオン又は有機カチオンを表わすことを特徴とする、請求項8に記載の付加物。
- Mがアンモニウム、ホスホニウム、テトラキス(ジアルキルアミノ)ホスホニウム、ビス[トリス(ジアルキルアミノ)]ジホスホニオアゼニウム、スルホニウム、ピリジニウム、アミジニウム、グアニジウム、イミダゾリウム、ピラゾリウム及びトリアゾリウムカチオンから選択される有機カチオン(該有機カチオンは、随意にアルキル、オキサアルキル、アリール、アルキルアリール及びアリールアルキル基から選択される置換基を有していてもよく、該カチオンは有機リンカーを介して互いに結合してオリゴマー又はポリマーを形成することもできる)であることを特徴とする、請求項11に記載の付加物。
- リチウムバッテリー中の電解質の添加剤としての、請求項1に記載の錯体の使用。
- Y1、Y2及びY3基の少なくとも1つがNR4以外の窒素含有基であり、又はX1、X2及びX3基の少なくとも1つがC=NCN又はC=C(CN)2基であることを特徴とする、請求項13に記載の使用。
- Cl又はBr原子を有する化合物を変性する方法であって、このCl又はBr原子を有する化合物と随意にその場で調製した請求項8に記載の付加物とを反応させて、Cl又はBrアニオンを求核置換反応によってF-、OCN-、O2-、[O2-M'+]-、O2 2-、[O2 2-M'+]-、O2 ・-、OH-、RO-、N3 -、CN-、NCN2-及び[NCN2-M'+]-から選択される原子価z'が1又は2であるZ'アニオンに置き換える工程を含むことを特徴とする、前記方法。
- 前記化合物が層状構造FeOCl、VOCl、BiOCl、BiONO3、TiNCl、TiNBr、ZrNCl若しくはZrNBrを有する無機化合物から選択される固体状化合物、又は{[CF3SO2NSO2Cl]-}nMn+、{[(ClSO2)2N]-}nMn+及び{[(Cl2PO)2N]-}nMn+から選択される液状化合物であることを特徴とする、請求項15に記載の方法。
- C−L結合{ここで、Cは炭素であり、LはCl、Br及びIから選択されるハロゲン、擬ハロゲン、エステル基−OSO2R'又は−N(SO2R')2基(ここで、R'はアルキル基、アルキルアリール基又はペルフルオロアルキル基である)である}を有する脂肪族又は芳香族有機化合物を変性する方法であって、前記有機化合物を請求項8に記載の付加物と反応させて、C−L結合をC−F、C−NCO、C−OCN、C−O-、C−O−C、C−OO-、C−O−O−C、C−OH、C−OR、C−N3又はC−CN結合に転化させることを特徴とする、前記方法。
- 有機化合物中のトリアルキルシラン基を脱保護する方法であって、該有機化合物をZがFである請求項8に記載の付加物と接触させてトリアルキルシラン基を水素原子に置き換えることから成ることを特徴とする、前記方法。
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FR0801506 | 2008-03-19 | ||
FR0801506A FR2928925B1 (fr) | 2008-03-19 | 2008-03-19 | Complexes de bore ou d'aluminium, et leurs utilisations. |
PCT/FR2009/000290 WO2009122044A2 (fr) | 2008-03-19 | 2009-03-19 | Complexes de bore ou d'aluminium |
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FR2963620B1 (fr) * | 2010-08-05 | 2012-07-27 | Rhodia Operations | Procede de preparation de l'acide difluoroacetique, ses sels ou ses esters |
US9431660B2 (en) | 2010-09-23 | 2016-08-30 | Robert Bosch Gmbh | Lithium battery with charging redox couple |
KR20120063163A (ko) * | 2010-12-07 | 2012-06-15 | 삼성전자주식회사 | 리튬 공기 전지 |
US9466431B2 (en) * | 2011-01-21 | 2016-10-11 | Nippon Shokubai Co., Ltd. | Ionic compound and process for production thereof, and electrolytic solution and electrical storage device each utilizing the ionic compound |
WO2013077863A1 (en) * | 2011-11-22 | 2013-05-30 | Robert Bosch Gmbh | Lithium battery with charging redox couple |
CN103420825A (zh) * | 2012-05-21 | 2013-12-04 | 上海品沃化工有限公司 | 二氟乙酸酯的合成方法 |
WO2014117028A1 (en) * | 2013-01-24 | 2014-07-31 | University Of South Florida | Acidic borate esters as 18f-labeled pet probes |
FR3009439B1 (fr) * | 2013-08-01 | 2017-08-25 | Renault Sas | Utilisation de borates comme inhibiteur de degradation des electrolytes organiques dans les accumulateurs electrochimiques |
EP3165528B1 (en) * | 2014-07-02 | 2021-08-18 | Central Glass Co., Ltd. | Ionic complex, electrolyte for nonaqueous electrolyte battery, nonaqueous electrolyte battery and ionic complex synthesis method |
US10424794B2 (en) | 2014-07-02 | 2019-09-24 | Central Glass Co., Ltd. | Ionic complex, electrolyte for nonaqueous electrolyte battery, nonaqueous electrolyte battery and ionic complex synthesis method |
AU2015346037A1 (en) * | 2014-11-14 | 2017-07-06 | Gemphire Therapeutics Inc. | Processes and intermediates for preparing alpha,omega-dicarboxylic acid-terminated dialkane ethers |
FR3038455B1 (fr) * | 2015-07-01 | 2020-03-13 | Renault S.A.S. | Compose utilise en tant qu'additif dans un electrolyte pour batterie a circulation d'ions |
JP2017022096A (ja) * | 2016-06-28 | 2017-01-26 | ロベルト・ボッシュ・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツングRobert Bosch Gmbh | 電気化学セル |
US10707531B1 (en) | 2016-09-27 | 2020-07-07 | New Dominion Enterprises Inc. | All-inorganic solvents for electrolytes |
KR102068759B1 (ko) * | 2018-09-18 | 2020-01-21 | 리켐주식회사 | 리튬이차전지용 전해질 첨가제 조성물 및 리튬이차전지용 전해질 첨가제 조성물의 제조 방법 |
CN109467539A (zh) * | 2018-10-31 | 2019-03-15 | 蒋玉贵 | 一种含有至少一种环状配体结构的化合物的制备方法和纯化方法 |
DE102019108288A1 (de) * | 2019-03-29 | 2020-10-01 | Technische Universität Darmstadt | Bicyclisches Triolborat und dessen Verwendung in einer Elektrolytzusammensetzung in einem Energiespeicher |
JP2023549011A (ja) | 2020-09-15 | 2023-11-22 | ヴァーヴ・セラピューティクス,インコーポレーテッド | 遺伝子編集のための脂質製剤 |
CN112670579B (zh) * | 2020-12-23 | 2022-02-25 | 东莞新能源科技有限公司 | 电解液、电化学装置及电子装置 |
WO2023214552A1 (ja) * | 2022-05-02 | 2023-11-09 | セントラル硝子株式会社 | トリフルオロメタンスルホニル化剤組成物、及び、トリフルオロメタンスルホニルオキシ化合物またはトリフルオロメタンスルホニル化合物の製造方法 |
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JPS59136364A (ja) * | 1983-01-25 | 1984-08-04 | Sankyo Yuki Gosei Kk | 防汚塗料 |
DE3807096A1 (de) | 1988-03-04 | 1989-09-14 | Bayer Ag | Verfahren zur herstellung von gummi/metall-verbundmaterialien mit hoher gummi/metall-haftung |
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JPH09297324A (ja) * | 1996-03-08 | 1997-11-18 | Sony Corp | 光学装置及び電解液 |
US6022643A (en) * | 1997-12-08 | 2000-02-08 | Brookhaven Science Associates | Boron compounds as anion binding agents for nonaqueous battery electrolytes |
JP2004511879A (ja) * | 2000-06-16 | 2004-04-15 | アリゾナ ボード オブ リージェンツ, ア ボディ コーポレイト アクティング オン ビハーフ オブ アリゾナ ステート ユニバーシティ | リチウム電池用伝導性ポリマー組成物 |
HUP0303945A2 (hu) | 2001-04-12 | 2004-03-29 | Rhodia Chimie | Nukleofil szubsztitúcióban alkalmazható katalizátorok, eljárás előállításukra, az ezeket tartalmazó készítmények és alkalmazásuk |
JP2004339475A (ja) * | 2003-02-03 | 2004-12-02 | Merck Patent Gmbh | フッ化物、オキシフッ化物、フルオロ硫化物および/またはオキシフルオロ硫化物に基づく真珠光沢顔料 |
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US8563761B2 (en) | 2013-10-22 |
US20110171112A1 (en) | 2011-07-14 |
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WO2009122044A2 (fr) | 2009-10-08 |
EP2276772B1 (fr) | 2014-08-20 |
EP2276772A2 (fr) | 2011-01-26 |
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JP2011515379A (ja) | 2011-05-19 |
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