CN100572385C - 具有氰基硼酸根阴离子的盐 - Google Patents
具有氰基硼酸根阴离子的盐 Download PDFInfo
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- CN100572385C CN100572385C CNB2007101361308A CN200710136130A CN100572385C CN 100572385 C CN100572385 C CN 100572385C CN B2007101361308 A CNB2007101361308 A CN B2007101361308A CN 200710136130 A CN200710136130 A CN 200710136130A CN 100572385 C CN100572385 C CN 100572385C
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- alkali metal
- salt
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- nmr
- reaction
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- 150000003839 salts Chemical class 0.000 title abstract description 28
- 125000004093 cyano group Chemical group *C#N 0.000 title abstract description 12
- URSLCTBXQMKCFE-UHFFFAOYSA-N dihydrogenborate Chemical compound OB(O)[O-] URSLCTBXQMKCFE-UHFFFAOYSA-N 0.000 title abstract description 7
- -1 organic cations salt Chemical class 0.000 claims abstract description 50
- 238000000034 method Methods 0.000 claims abstract description 18
- 229910052728 basic metal Inorganic materials 0.000 claims abstract description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 30
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical group [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 30
- 229910052744 lithium Inorganic materials 0.000 claims description 18
- 229910052700 potassium Inorganic materials 0.000 claims description 11
- 229910052708 sodium Inorganic materials 0.000 claims description 11
- 229910052792 caesium Inorganic materials 0.000 claims description 10
- 229910052701 rubidium Inorganic materials 0.000 claims description 10
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 claims description 5
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 claims description 4
- 238000003746 solid phase reaction Methods 0.000 claims description 4
- 238000010671 solid-state reaction Methods 0.000 claims description 4
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Inorganic materials [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 21
- 239000002608 ionic liquid Substances 0.000 abstract description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- 239000002904 solvent Substances 0.000 description 21
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000011734 sodium Substances 0.000 description 15
- 238000000921 elemental analysis Methods 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 239000007788 liquid Substances 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 230000004927 fusion Effects 0.000 description 12
- 239000003643 water by type Substances 0.000 description 12
- 238000004607 11B NMR spectroscopy Methods 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 10
- 150000002500 ions Chemical class 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000001035 drying Methods 0.000 description 9
- 238000000605 extraction Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 150000002892 organic cations Chemical class 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IBZJNLWLRUHZIX-UHFFFAOYSA-N 1-ethyl-3-methyl-2h-imidazole Chemical compound CCN1CN(C)C=C1 IBZJNLWLRUHZIX-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 238000004009 13C{1H}-NMR spectroscopy Methods 0.000 description 5
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 235000011167 hydrochloric acid Nutrition 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000013558 reference substance Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 4
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 3
- UIOWFYDMDBRHLM-UHFFFAOYSA-N 2-butyl-3-methylpyridine Chemical compound CCCCC1=NC=CC=C1C UIOWFYDMDBRHLM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- KVMPQUTWRWVTQP-UHFFFAOYSA-N cyanatoboronic acid Chemical compound OB(O)OC#N KVMPQUTWRWVTQP-UHFFFAOYSA-N 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000004570 mortar (masonry) Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000004834 15N NMR spectroscopy Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910019093 NaOCl Inorganic materials 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001449 anionic compounds Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000005496 eutectics Effects 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000002243 precursor Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- KAIPKTYOBMEXRR-UHFFFAOYSA-N 1-butyl-3-methyl-2h-imidazole Chemical compound CCCCN1CN(C)C=C1 KAIPKTYOBMEXRR-UHFFFAOYSA-N 0.000 description 1
- 101710134784 Agnoprotein Proteins 0.000 description 1
- FZSZOSZXHJXUJC-UHFFFAOYSA-N B(C#N)(O)OC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3 Chemical compound B(C#N)(O)OC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3 FZSZOSZXHJXUJC-UHFFFAOYSA-N 0.000 description 1
- RTFSLYLXYQIZMQ-UHFFFAOYSA-N B(O)(O)O.B(O)(O)O.B(O)(O)O.B(O)(O)O.C(#N)[Li] Chemical compound B(O)(O)O.B(O)(O)O.B(O)(O)O.B(O)(O)O.C(#N)[Li] RTFSLYLXYQIZMQ-UHFFFAOYSA-N 0.000 description 1
- MOOIJFDMRCXAKU-UHFFFAOYSA-N B([O-])([O-])[O-].C(#N)CC[N+](CC)(CC)CC.C(#N)CC[N+](CC)(CC)CC.C(#N)CC[N+](CC)(CC)CC Chemical compound B([O-])([O-])[O-].C(#N)CC[N+](CC)(CC)CC.C(#N)CC[N+](CC)(CC)CC.C(#N)CC[N+](CC)(CC)CC MOOIJFDMRCXAKU-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- LGMSMWWJASYYGR-UHFFFAOYSA-N C(C)N1CN(C=C1)C.B(O)(O)C#N Chemical compound C(C)N1CN(C=C1)C.B(O)(O)C#N LGMSMWWJASYYGR-UHFFFAOYSA-N 0.000 description 1
- SVZKTPAFWNRSET-UHFFFAOYSA-N C(CCC)N1CN(C=C1)C.B(O)(O)C#N Chemical compound C(CCC)N1CN(C=C1)C.B(O)(O)C#N SVZKTPAFWNRSET-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 238000006117 Diels-Alder cycloaddition reaction Methods 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- FVIGODVHAVLZOO-UHFFFAOYSA-N Dixanthogen Chemical compound CCOC(=S)SSC(=S)OCC FVIGODVHAVLZOO-UHFFFAOYSA-N 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 206010016825 Flushing Diseases 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 238000007341 Heck reaction Methods 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 229910013553 LiNO Inorganic materials 0.000 description 1
- XADZFWQMHPDWRY-UHFFFAOYSA-N NC#N.NC#N.NC#N.OB(O)O Chemical compound NC#N.NC#N.NC#N.OB(O)O XADZFWQMHPDWRY-UHFFFAOYSA-N 0.000 description 1
- 238000001237 Raman spectrum Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000009841 combustion method Methods 0.000 description 1
- HZXXSCOUSGLRRX-UHFFFAOYSA-N cyanoboronic acid Chemical compound OB(O)C#N HZXXSCOUSGLRRX-UHFFFAOYSA-N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- OKVJWADVFPXWQD-UHFFFAOYSA-N difluoroborinic acid Chemical compound OB(F)F OKVJWADVFPXWQD-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- JORQDGTZGKHEEO-UHFFFAOYSA-N lithium cyanide Chemical compound [Li+].N#[C-] JORQDGTZGKHEEO-UHFFFAOYSA-N 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000011255 nonaqueous electrolyte Substances 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 238000007430 reference method Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910001495 sodium tetrafluoroborate Inorganic materials 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 238000004454 trace mineral analysis Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- CCZXMDQFIVMWMF-UHFFFAOYSA-N trifluoromethoxyboronic acid Chemical compound OB(O)OC(F)(F)F CCZXMDQFIVMWMF-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/20—Quaternary compounds thereof
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—Quaternary ammonium compounds
- C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—Quaternary ammonium compounds
- C07C211/64—Quaternary ammonium compounds having quaternised nitrogen atoms bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
-
- 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
- C07F5/027—Organoboranes and organoborohydrides
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- 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
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| Application Number | Priority Date | Filing Date | Title |
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| DE10306617.9 | 2003-02-14 | ||
| DE10306617A DE10306617A1 (de) | 2003-02-14 | 2003-02-14 | Salze mit Cyanoborat-Anionen |
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| CNB2004800041330A Division CN100361997C (zh) | 2003-02-14 | 2004-01-15 | 具有氰基硼酸根阴离子的盐 |
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| CN2007101361295A Expired - Fee Related CN101108861B (zh) | 2003-02-14 | 2004-01-15 | 具有氰基硼酸根阴离子的盐 |
| CNB2004800041330A Expired - Fee Related CN100361997C (zh) | 2003-02-14 | 2004-01-15 | 具有氰基硼酸根阴离子的盐 |
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| CNB2004800041330A Expired - Fee Related CN100361997C (zh) | 2003-02-14 | 2004-01-15 | 具有氰基硼酸根阴离子的盐 |
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| Country | Link |
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| US (1) | US7645434B2 (https=) |
| EP (3) | EP1592696B1 (https=) |
| JP (1) | JP4718438B2 (https=) |
| KR (4) | KR20110110873A (https=) |
| CN (3) | CN100572385C (https=) |
| AT (3) | ATE368045T1 (https=) |
| CA (2) | CA2515856C (https=) |
| DE (4) | DE10306617A1 (https=) |
| ES (1) | ES2271837T3 (https=) |
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| WO2011085964A1 (en) | 2010-01-18 | 2011-07-21 | Merck Patent Gmbh | Electrolyte formulations |
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| CN102933082A (zh) * | 2010-04-22 | 2013-02-13 | 杰内塞斯实验室股份有限公司 | 用于防治白蛉和其它吸血昆虫的组合物和方法 |
| EP2388853A1 (en) | 2010-05-20 | 2011-11-23 | Fundacion Cidetec | Ionic liquid based electrolytes containing sulfide/polysulfide redox couple and uses thereof |
| JP5950916B2 (ja) * | 2010-09-28 | 2016-07-13 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | シアノ−アルコキシ−ボレートアニオンを含む電解質配合物 |
| AU2011307222B2 (en) * | 2010-09-30 | 2015-04-02 | Merck Patent Gmbh | Electrolyte formulations |
| EP2646487B1 (en) | 2010-11-30 | 2020-05-27 | Merck Patent GmbH | Particles for electrophoretic displays |
| EP2649625A1 (en) | 2010-12-08 | 2013-10-16 | Merck Patent GmbH | Additives for dye-sensitized solar cells |
| KR101814041B1 (ko) | 2011-01-21 | 2018-01-02 | 가부시기가이샤 닛뽕쇼꾸바이 | 이온성 화합물, 그 제조방법, 및, 이것을 사용한 전해액, 및, 축전 디바이스 |
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| DE102011103754A1 (de) * | 2011-05-31 | 2012-12-06 | Merck Patent Gmbh | Verfahren zur Herstellung von Dihydridodicyanoborat-Salzen |
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| KR102285708B1 (ko) | 2011-07-08 | 2021-08-04 | 패스트캡 시스템즈 코포레이션 | 고온 에너지 저장 장치 |
| EP2731955B1 (en) * | 2011-07-15 | 2017-01-11 | Merck Patent GmbH | Compounds containing alkyl-cyano-borate or alkyl-cyano-fluoroborate anions |
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| JP5813472B2 (ja) * | 2011-09-06 | 2015-11-17 | 株式会社日本触媒 | テトラシアノボレート塩の製造方法 |
| EP2623457A1 (en) | 2012-02-02 | 2013-08-07 | VTU Holding GmbH | Use of an ionic liquid for storing hydrogen |
| KR102093832B1 (ko) | 2012-02-08 | 2020-03-26 | 메르크 파텐트 게엠베하 | 전도성 첨가제를 포함하는 반응성 메소겐 제제 |
| WO2014029834A1 (en) * | 2012-08-24 | 2014-02-27 | Lonza Ltd | Method for the preparation of tetraalkylammonium tetracyanidoborates |
| WO2014029833A1 (en) * | 2012-08-24 | 2014-02-27 | Lonza Ltd | Method for the preparation of tetraalkylammonium or tetraalkylphosphonium|tricyanidofluoroborates |
| US9269958B2 (en) * | 2012-12-07 | 2016-02-23 | Samsung Electronics Co., Ltd. | Cathode and all-solid battery including the same |
| EP2772495A1 (en) * | 2013-03-01 | 2014-09-03 | Lonza Ltd | Method for preparation of tricyanidofluoroborates in 2 steps |
| DE102013009959A1 (de) | 2013-06-14 | 2014-12-31 | Julius-Maximilians-Universität Würzburg | Verfahren zur Herstellung von Salzen mit Hydridocyanoborat-Anionen |
| DE102013013502A1 (de) | 2013-08-16 | 2015-03-12 | Julius-Maximilians-Universität Würzburg | Hexacyanodiborate |
| US10872737B2 (en) | 2013-10-09 | 2020-12-22 | Fastcap Systems Corporation | Advanced electrolytes for high temperature energy storage device |
| JP2015103288A (ja) | 2013-11-21 | 2015-06-04 | ソニー株式会社 | 二次電池、電池パック、電動車両および電力貯蔵システム |
| WO2015186568A1 (ja) * | 2014-06-04 | 2015-12-10 | 株式会社トクヤマ | 非水電解液およびそれを用いた蓄電デバイス |
| DE102014008130A1 (de) | 2014-06-06 | 2015-12-17 | Julius-Maximilians-Universität Würzburg | Verfahren zur Herstellung von Tetracyanoboratsalzen |
| DE102014014967A1 (de) | 2014-10-14 | 2016-04-14 | Julius-Maximilians-Universität Würzburg | Verfahren zur Herstellung von Verbindungen mit Monofluorotricyanoborat-Anionen |
| KR20230164229A (ko) | 2015-01-27 | 2023-12-01 | 패스트캡 시스템즈 코포레이션 | 넓은 온도 범위 울트라커패시터 |
| DE102016001344A1 (de) | 2015-09-10 | 2017-03-16 | Julius-Maximilians-Universität Würzburg | Verfahren zur Herstellung von Kaliummonofluorotricyanoborat |
| KR102697024B1 (ko) | 2015-09-25 | 2024-08-20 | 닛뽄 가야쿠 가부시키가이샤 | 아조 화합물, 잉크 조성물, 잉크젯 기록 방법 및 착색체 |
| DE102015016400A1 (de) | 2015-12-18 | 2017-06-22 | Julius-Maximilians-Universität Würzburg | Verfahren zur Herstellung von Salzen mit Perfluoralkyltricyanoboratanionen oder Tetracyanoboratanionen |
| DE102015016401A1 (de) | 2015-12-18 | 2017-06-22 | Julius-Maximilians-Universität Würzburg | Verfahren zur Herstellung von Salzen mit Monofluorotricyanoboratanionen |
| DE102016009846A1 (de) | 2016-08-16 | 2018-02-22 | Julius-Maximilians-Universität Würzburg | Fluoralkylhydrido- und Fluoralkylcyanohydridoborate |
| EP4243122A3 (en) | 2016-12-02 | 2023-11-15 | Fastcap Systems Corporation | Composite electrode |
| JP2021141101A (ja) * | 2020-03-02 | 2021-09-16 | 日清紡ホールディングス株式会社 | 蓄電デバイス用電解液およびイオン液体 |
| CN115477308B (zh) * | 2022-08-28 | 2023-05-02 | 兰州理工大学 | 一种一步法常温制备四氟硼酸钠的方法 |
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| JPS5542292A (en) | 1978-09-18 | 1980-03-25 | Thiokol Chemical Corp | Method of synthesizing nabh3cn and related compounds |
| US4301129A (en) * | 1978-09-18 | 1981-11-17 | Thiokol Corporation | Synthesis of NaBH3 CN and related compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07116113B2 (ja) | 1987-05-14 | 1995-12-13 | 三菱化学株式会社 | 四級アンモニウム無機酸塩の製造方法 |
| US4892944A (en) * | 1987-05-13 | 1990-01-09 | Mitsubishi Petrochemical Co., Ltd. | Process for producing quaternary salts |
| DE10055811A1 (de) * | 2000-11-10 | 2002-05-29 | Merck Patent Gmbh | Tetrakisfluoroalkylborat-Salze und deren Verwendung als Leitsalze |
| CN1449069A (zh) * | 2002-04-02 | 2003-10-15 | 株式会社日本触媒 | 电解质溶液用材料及其用途 |
| JP4467247B2 (ja) | 2002-04-02 | 2010-05-26 | 株式会社日本触媒 | 新規溶融塩を用いたイオン伝導体 |
| JP4127788B2 (ja) * | 2002-11-22 | 2008-07-30 | 株式会社トクヤマ | オニウム塩 |
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2003
- 2003-02-14 DE DE10306617A patent/DE10306617A1/de not_active Withdrawn
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- 2004-01-15 US US10/545,690 patent/US7645434B2/en not_active Expired - Fee Related
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- 2004-01-15 JP JP2006501548A patent/JP4718438B2/ja not_active Expired - Fee Related
- 2004-01-15 KR KR1020127017205A patent/KR101287689B1/ko not_active Expired - Fee Related
- 2004-01-15 EP EP06016495A patent/EP1726594B1/de not_active Expired - Lifetime
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| JPS5542292A (en) | 1978-09-18 | 1980-03-25 | Thiokol Chemical Corp | Method of synthesizing nabh3cn and related compounds |
| US4301129A (en) * | 1978-09-18 | 1981-11-17 | Thiokol Corporation | Synthesis of NaBH3 CN and related compounds |
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| Synthesis of LiBC4N4,BC3N3,and Related C-N CompoundsofBoron:New Precursors to light Element Ceramics. Darrick Williams 等.Journal of the American Chemical Society,Vol.122 No.32. 2000 * |
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