CA2509226C - Ionic liquids having [n(cf3)2]- anions - Google Patents
Ionic liquids having [n(cf3)2]- anions Download PDFInfo
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- CA2509226C CA2509226C CA2509226A CA2509226A CA2509226C CA 2509226 C CA2509226 C CA 2509226C CA 2509226 A CA2509226 A CA 2509226A CA 2509226 A CA2509226 A CA 2509226A CA 2509226 C CA2509226 C CA 2509226C
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- carbon atoms
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- saturated
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- Prior art date
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 20
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 70
- 150000003839 salts Chemical class 0.000 claims abstract description 64
- -1 bis(trifluoromethyl)imide anions Chemical class 0.000 claims abstract description 44
- 238000000034 method Methods 0.000 claims abstract description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 67
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 66
- 125000004432 carbon atom Chemical group C* 0.000 claims description 66
- 229910052698 phosphorus Inorganic materials 0.000 claims description 49
- 229910052757 nitrogen Inorganic materials 0.000 claims description 48
- 125000001424 substituent group Chemical group 0.000 claims description 46
- 229910052717 sulfur Inorganic materials 0.000 claims description 43
- 229910052760 oxygen Inorganic materials 0.000 claims description 42
- 125000000623 heterocyclic group Chemical group 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 26
- 150000002367 halogens Chemical group 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 239000000460 chlorine Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 229910001515 alkali metal fluoride Inorganic materials 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229910052801 chlorine Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 239000003495 polar organic solvent Substances 0.000 claims description 6
- 229910052727 yttrium Inorganic materials 0.000 claims description 6
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- UFBJCMHMOXMLKC-UHFFFAOYSA-M 2,4-dinitrophenol(1-) Chemical compound [O-]C1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-M 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 238000005580 one pot reaction Methods 0.000 claims description 3
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000004973 liquid crystal related substance Substances 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 239000011255 nonaqueous electrolyte Substances 0.000 claims description 2
- 239000003444 phase transfer catalyst Substances 0.000 claims description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 2
- 239000011814 protection agent Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 150000003254 radicals Chemical class 0.000 claims 3
- 238000006467 substitution reaction Methods 0.000 claims 2
- 125000001814 trioxo-lambda(7)-chloranyloxy group Chemical group *OCl(=O)(=O)=O 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 1
- 235000013350 formula milk Nutrition 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
- 150000001768 cations Chemical class 0.000 description 16
- AHLATJUETSFVIM-UHFFFAOYSA-M rubidium fluoride Chemical compound [F-].[Rb+] AHLATJUETSFVIM-UHFFFAOYSA-M 0.000 description 12
- 125000004437 phosphorous atom Chemical group 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- JAAGVIUFBAHDMA-UHFFFAOYSA-M rubidium bromide Chemical compound [Br-].[Rb+] JAAGVIUFBAHDMA-UHFFFAOYSA-M 0.000 description 10
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 9
- 125000004429 atom Chemical group 0.000 description 9
- ZGLLUEAYLAHJKB-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethyl)methanamine Chemical compound FC(F)(F)NC(F)(F)F ZGLLUEAYLAHJKB-UHFFFAOYSA-N 0.000 description 8
- 125000004434 sulfur atom Chemical group 0.000 description 8
- 238000004293 19F NMR spectroscopy Methods 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 230000001376 precipitating effect Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- 229960005419 nitrogen Drugs 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Inorganic materials [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- SLVAEVYIJHDKRO-UHFFFAOYSA-N trifluoromethanesulfonyl fluoride Chemical compound FC(F)(F)S(F)(=O)=O SLVAEVYIJHDKRO-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 150000002829 nitrogen Chemical class 0.000 description 4
- 239000011698 potassium fluoride Substances 0.000 description 4
- NCCSSGKUIKYAJD-UHFFFAOYSA-N rubidium(1+) Chemical compound [Rb+] NCCSSGKUIKYAJD-UHFFFAOYSA-N 0.000 description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- 229910020008 S(O) Inorganic materials 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 150000002926 oxygen Chemical class 0.000 description 3
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 description 2
- 229910020261 KBF4 Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 235000003270 potassium fluoride Nutrition 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- FHDQNOXQSTVAIC-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;chloride Chemical compound [Cl-].CCCCN1C=C[N+](C)=C1 FHDQNOXQSTVAIC-UHFFFAOYSA-M 0.000 description 1
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 1
- NIHOUJYFWMURBG-UHFFFAOYSA-N 1-ethyl-1-methylpyrrolidin-1-ium Chemical compound CC[N+]1(C)CCCC1 NIHOUJYFWMURBG-UHFFFAOYSA-N 0.000 description 1
- KHJQQUGSPDBDRM-UHFFFAOYSA-M 1-ethyl-1-methylpyrrolidin-1-ium;bromide Chemical compound [Br-].CC[N+]1(C)CCCC1 KHJQQUGSPDBDRM-UHFFFAOYSA-M 0.000 description 1
- QGSALMLCNHOVOE-UHFFFAOYSA-N 3-ethyl-1,3-benzothiazol-3-ium Chemical compound C1=CC=C2[N+](CC)=CSC2=C1 QGSALMLCNHOVOE-UHFFFAOYSA-N 0.000 description 1
- XBWYYTURPBHPFJ-UHFFFAOYSA-M 3-ethyl-1,3-benzothiazol-3-ium;bromide Chemical compound [Br-].C1=CC=C2[N+](CC)=CSC2=C1 XBWYYTURPBHPFJ-UHFFFAOYSA-M 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- 229910017048 AsF6 Inorganic materials 0.000 description 1
- 229910015898 BF4 Inorganic materials 0.000 description 1
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 102000020897 Formins Human genes 0.000 description 1
- 108091022623 Formins Proteins 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 description 1
- 238000007341 Heck reaction Methods 0.000 description 1
- 229910014332 N(SO2CF3)2 Inorganic materials 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101100495923 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr2 gene Proteins 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- XHIHMDHAPXMAQK-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-butylpyridin-1-ium Chemical compound CCCC[N+]1=CC=CC=C1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F XHIHMDHAPXMAQK-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 238000012821 model calculation Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229960003903 oxygen Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 235000014786 phosphorus Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000007686 potassium Nutrition 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 150000003297 rubidium Chemical class 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- 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
- C07D213/18—Salts thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- 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
- C07D233/56—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 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Catalysts (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Primary Cells (AREA)
- Secondary Cells (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10258671A DE10258671A1 (de) | 2002-12-13 | 2002-12-13 | Ionische Flüssigkeiten mit [N(CF3)2]-Anionen |
| DE10258671.3 | 2002-12-13 | ||
| PCT/EP2003/012811 WO2004054991A1 (de) | 2002-12-13 | 2003-11-17 | Ionische flüssigkeiten mit [n(cf3)2]--anionen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2509226A1 CA2509226A1 (en) | 2004-07-01 |
| CA2509226C true CA2509226C (en) | 2012-05-01 |
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| Application Number | Title | Priority Date | Filing Date |
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| CA2509226A Expired - Fee Related CA2509226C (en) | 2002-12-13 | 2003-11-17 | Ionic liquids having [n(cf3)2]- anions |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7550491B2 (https=) |
| EP (1) | EP1569921A1 (https=) |
| JP (2) | JP4790270B2 (https=) |
| KR (1) | KR101222271B1 (https=) |
| CN (1) | CN1726200A (https=) |
| AU (1) | AU2003294712B2 (https=) |
| CA (1) | CA2509226C (https=) |
| DE (1) | DE10258671A1 (https=) |
| RU (1) | RU2351601C2 (https=) |
| WO (1) | WO2004054991A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0500029D0 (en) * | 2005-01-04 | 2005-02-09 | Univ Belfast | Basic ionic liquids |
| JP4766914B2 (ja) * | 2005-05-10 | 2011-09-07 | 関東電化工業株式会社 | Ｓを含む環状イオン液体およびその製造方法 |
| KR100866369B1 (ko) * | 2006-05-16 | 2008-10-31 | 도요타지도샤가부시키가이샤 | 실린더 헤드 개스킷 |
| DE102006023649A1 (de) * | 2006-05-17 | 2008-01-03 | Philipps-Universität Marburg | Hydrophobe ionische Flüssigkeiten |
| DE112009000286A5 (de) * | 2008-01-30 | 2010-10-28 | Technische Universität Dresden | Salze mit Aryl-Alkyl-substituierten Imidazolium- und Triazoliumkationen und deren Verwendung |
| CN101863855B (zh) * | 2010-06-29 | 2013-05-29 | 四川大学 | 温敏型酸性离子液体的制备及其催化醇酸酯化的方法 |
| JP5328745B2 (ja) * | 2010-10-25 | 2013-10-30 | 国立大学法人 名古屋工業大学 | リチウム二次電池 |
| ES2523689B1 (es) * | 2013-04-26 | 2019-06-19 | Consejo Superior Investigacion | Liquidos ionicos, procedimiento de preparacion y su uso como electrolitos para dispositivos electroquimicos de almacenamiento de energia |
| KR102690302B1 (ko) * | 2021-10-15 | 2024-07-30 | 단국대학교 천안캠퍼스 산학협력단 | 리튬 이차 전지용 전해질, 그 제조 방법 및 이를 포함하는 리튬 이차 전지 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5827602A (en) * | 1995-06-30 | 1998-10-27 | Covalent Associates Incorporated | Hydrophobic ionic liquids |
| DE19941566A1 (de) | 1999-09-01 | 2001-03-08 | Merck Patent Gmbh | Stabile (CF3)2N-Salze und Verfahren zu deren Herstellung |
| DE10026565A1 (de) * | 2000-05-30 | 2001-12-06 | Merck Patent Gmbh | Ionische Flüssigkeiten |
| JP4011830B2 (ja) * | 2000-06-20 | 2007-11-21 | 独立行政法人科学技術振興機構 | Ｎ−アルコキシアルキルイミダゾリウム塩、該イミダゾリウム塩からなるイオン液体ならびにイオン性ゲル |
| DE10107118A1 (de) * | 2001-02-14 | 2002-08-29 | Merck Patent Gmbh | Verfahren zur Herstellung von Bis(trifluormethyl)imido-Salzen |
-
2002
- 2002-12-13 DE DE10258671A patent/DE10258671A1/de not_active Withdrawn
-
2003
- 2003-11-17 JP JP2004559692A patent/JP4790270B2/ja not_active Expired - Fee Related
- 2003-11-17 CN CNA2003801059765A patent/CN1726200A/zh active Pending
- 2003-11-17 WO PCT/EP2003/012811 patent/WO2004054991A1/de not_active Ceased
- 2003-11-17 KR KR1020057010682A patent/KR101222271B1/ko not_active Expired - Fee Related
- 2003-11-17 RU RU2005121906/04A patent/RU2351601C2/ru not_active IP Right Cessation
- 2003-11-17 CA CA2509226A patent/CA2509226C/en not_active Expired - Fee Related
- 2003-11-17 US US10/538,847 patent/US7550491B2/en not_active Expired - Fee Related
- 2003-11-17 EP EP03785645A patent/EP1569921A1/de not_active Withdrawn
- 2003-11-17 AU AU2003294712A patent/AU2003294712B2/en not_active Ceased
-
2011
- 2011-03-30 JP JP2011074239A patent/JP2011201879A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2011201879A (ja) | 2011-10-13 |
| JP4790270B2 (ja) | 2011-10-12 |
| AU2003294712B2 (en) | 2010-08-12 |
| KR101222271B1 (ko) | 2013-01-15 |
| DE10258671A1 (de) | 2004-06-24 |
| CA2509226A1 (en) | 2004-07-01 |
| US20060079691A1 (en) | 2006-04-13 |
| RU2005121906A (ru) | 2006-01-27 |
| JP2006516123A (ja) | 2006-06-22 |
| CN1726200A (zh) | 2006-01-25 |
| AU2003294712A1 (en) | 2004-07-09 |
| WO2004054991A8 (de) | 2005-09-01 |
| EP1569921A1 (de) | 2005-09-07 |
| WO2004054991A1 (de) | 2004-07-01 |
| RU2351601C2 (ru) | 2009-04-10 |
| KR20050085577A (ko) | 2005-08-29 |
| US7550491B2 (en) | 2009-06-23 |
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