DE19610908A1 - Verfahren zur Herstellung heterocyclischer Carbene - Google Patents
Verfahren zur Herstellung heterocyclischer CarbeneInfo
- Publication number
- DE19610908A1 DE19610908A1 DE19610908A DE19610908A DE19610908A1 DE 19610908 A1 DE19610908 A1 DE 19610908A1 DE 19610908 A DE19610908 A DE 19610908A DE 19610908 A DE19610908 A DE 19610908A DE 19610908 A1 DE19610908 A1 DE 19610908A1
- Authority
- DE
- Germany
- Prior art keywords
- mmol
- nmr
- ppm
- mhz
- thf
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 26
- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 18
- 230000008569 process Effects 0.000 title claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 title abstract description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 78
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 39
- 238000006243 chemical reaction Methods 0.000 claims abstract description 35
- 239000000203 mixture Substances 0.000 claims abstract description 28
- 150000001412 amines Chemical class 0.000 claims abstract description 19
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000003880 polar aprotic solvent Substances 0.000 claims abstract description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 11
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 9
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 108
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 54
- -1 metal complex anions Chemical class 0.000 claims description 51
- 238000002360 preparation method Methods 0.000 claims description 41
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 29
- 229910021529 ammonia Inorganic materials 0.000 claims description 29
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 16
- 230000005595 deprotonation Effects 0.000 claims description 13
- 238000010537 deprotonation reaction Methods 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 150000003254 radicals Chemical class 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 5
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- 150000007942 carboxylates Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 3
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- DJMUYABFXCIYSC-UHFFFAOYSA-N 1H-phosphole Chemical group C=1C=CPC=1 DJMUYABFXCIYSC-UHFFFAOYSA-N 0.000 claims description 2
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000000707 boryl group Chemical group B* 0.000 claims description 2
- 150000001720 carbohydrates Chemical class 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 150000002527 isonitriles Chemical class 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- 125000002577 pseudohalo group Chemical group 0.000 claims description 2
- OKQKDCXVLPGWPO-UHFFFAOYSA-N sulfanylidenephosphane Chemical compound S=P OKQKDCXVLPGWPO-UHFFFAOYSA-N 0.000 claims description 2
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000001118 alkylidene group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 57
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 52
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 38
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 36
- 238000005160 1H NMR spectroscopy Methods 0.000 description 27
- 239000002904 solvent Substances 0.000 description 26
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 23
- 239000000047 product Substances 0.000 description 22
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 14
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000010948 rhodium Substances 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 229910052721 tungsten Inorganic materials 0.000 description 11
- 239000010937 tungsten Substances 0.000 description 11
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 238000001819 mass spectrum Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- 239000013256 coordination polymer Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- 238000000921 elemental analysis Methods 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 229910052703 rhodium Inorganic materials 0.000 description 7
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 7
- JBOIAZWJIACNJF-UHFFFAOYSA-N 1h-imidazole;hydroiodide Chemical compound [I-].[NH2+]1C=CN=C1 JBOIAZWJIACNJF-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 239000000306 component Substances 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 5
- FGNXWZNESBMJDB-UHFFFAOYSA-M 1-methyl-3-(2-phenylethyl)imidazol-1-ium;chloride Chemical compound [Cl-].C1=[N+](C)C=CN1CCC1=CC=CC=C1 FGNXWZNESBMJDB-UHFFFAOYSA-M 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 150000004693 imidazolium salts Chemical class 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 4
- OTDKPPZHTSYUFY-UHFFFAOYSA-N 1,2-bis(2-ethoxyethyl)-1h-imidazol-1-ium;chloride Chemical compound [Cl-].CCOCC[NH+]1C=CN=C1CCOCC OTDKPPZHTSYUFY-UHFFFAOYSA-N 0.000 description 4
- ACNNHRDJONEBAU-UHFFFAOYSA-N 1,3-bis(2-ethoxyethyl)imidazolidine-2-thione Chemical compound CCOCCN1CCN(CCOCC)C1=S ACNNHRDJONEBAU-UHFFFAOYSA-N 0.000 description 4
- XGJRZQHDLLMQMR-QJHJCNPRSA-M 1,3-bis[(1s)-1-phenylethyl]imidazol-1-ium;chloride Chemical compound [Cl-].C1([C@H](C)N2C=[N+](C=C2)[C@@H](C)C=2C=CC=CC=2)=CC=CC=C1 XGJRZQHDLLMQMR-QJHJCNPRSA-M 0.000 description 4
- UPJKDKOHHMKJAY-UHFFFAOYSA-M 1,3-dicyclohexylimidazol-1-ium;chloride Chemical compound [Cl-].C1CCCCC1N1C=[N+](C2CCCCC2)C=C1 UPJKDKOHHMKJAY-UHFFFAOYSA-M 0.000 description 4
- ARSMIBSHEYKMJT-UHFFFAOYSA-M 1,3-dimethylimidazolium iodide Chemical compound [I-].CN1C=C[N+](C)=C1 ARSMIBSHEYKMJT-UHFFFAOYSA-M 0.000 description 4
- BMSQFGRKCYMWOK-UHFFFAOYSA-M 1-(2-diphenylphosphorylethyl)-3-methylimidazol-3-ium;iodide Chemical compound [I-].C1=[N+](C)C=CN1CCP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 BMSQFGRKCYMWOK-UHFFFAOYSA-M 0.000 description 4
- UWSNRJHXDNLVTK-UHFFFAOYSA-N 3-hexyl-1H-imidazol-3-ium bromide Chemical compound [Br-].CCCCCC[n+]1cc[nH]c1 UWSNRJHXDNLVTK-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- WYURNTSHIVDZCO-SVYQBANQSA-N deuterated tetrahydrofuran Substances [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 4
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 4
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000010583 slow cooling Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- NUXHRJHNSNRMMO-UHFFFAOYSA-N 1-(2-ethoxyethyl)imidazole Chemical compound CCOCCN1C=CN=C1 NUXHRJHNSNRMMO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 101150046432 Tril gene Proteins 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000007717 exclusion Effects 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- GGHWXKOGMYDZMN-UHFFFAOYSA-M n,n-diethyl-2-(3-methylimidazol-3-ium-1-yl)ethanamine;chloride;hydrochloride Chemical compound Cl.[Cl-].CCN(CC)CC[N+]=1C=CN(C)C=1 GGHWXKOGMYDZMN-UHFFFAOYSA-M 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- JTDDTDXTQHFZST-UHFFFAOYSA-N potassium;imidazol-3-ide Chemical compound [K+].C1=C[N-]C=N1 JTDDTDXTQHFZST-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RWEKCIFYYHIVCL-UHFFFAOYSA-N (1,3-dicyclohexylimidazolidin-2-ylidene)rhodium Chemical compound C1(CCCCC1)N1C(N(CC1)C1CCCCC1)=[Rh] RWEKCIFYYHIVCL-UHFFFAOYSA-N 0.000 description 2
- RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 description 2
- ADEAKBPMDSUYCI-HOTGVXAUSA-N 1,3-bis[(1s)-1-phenylethyl]imidazole-2-thione Chemical compound C1([C@H](C)N2C(N([C@@H](C)C=3C=CC=CC=3)C=C2)=S)=CC=CC=C1 ADEAKBPMDSUYCI-HOTGVXAUSA-N 0.000 description 2
- MMYKTRPLXXWLBC-UHFFFAOYSA-N 1-bromo-2-ethoxyethane Chemical compound CCOCCBr MMYKTRPLXXWLBC-UHFFFAOYSA-N 0.000 description 2
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 2
- KGWVFQAPOGAVRF-UHFFFAOYSA-N 1-hexylimidazole Chemical class CCCCCCN1C=CN=C1 KGWVFQAPOGAVRF-UHFFFAOYSA-N 0.000 description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical group CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- WNELWRQHSXMDFH-UHFFFAOYSA-N [1-[2-(diethylamino)ethyl]-3-methylimidazolidin-2-ylidene]rhodium Chemical compound C(C)N(CCN1C(N(CC1)C)=[Rh])CC WNELWRQHSXMDFH-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 150000004696 coordination complex Chemical group 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229940015043 glyoxal Drugs 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- KMWHDCFJGZBQKB-UHFFFAOYSA-M n-ethyl-2-(3-methylimidazol-3-ium-1-yl)ethanamine;chloride;hydrochloride Chemical compound Cl.[Cl-].CCNCC[N+]=1C=CN(C)C=1 KMWHDCFJGZBQKB-UHFFFAOYSA-M 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- UKNZUHFKVZLMPG-UHFFFAOYSA-N (1,3-dimethylimidazolidin-2-ylidene)rhodium Chemical compound CN1CCN(C)C1=[Rh] UKNZUHFKVZLMPG-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- QGRBYPFRBRYULL-UHFFFAOYSA-N 1,3-dihexylimidazol-1-ium Chemical compound CCCCCCN1C=C[N+](CCCCCC)=C1 QGRBYPFRBRYULL-UHFFFAOYSA-N 0.000 description 1
- LSKGVMCYWOQFJO-UHFFFAOYSA-M 1,3-dihexylimidazol-1-ium bromide Chemical compound [Br-].CCCCCCN1C=C[N+](CCCCCC)=C1 LSKGVMCYWOQFJO-UHFFFAOYSA-M 0.000 description 1
- HLARWPSCENWPHP-UHFFFAOYSA-N 1,3-dihexylimidazolidine-2-thione Chemical compound CCCCCCN1CCN(CCCCCC)C1=S HLARWPSCENWPHP-UHFFFAOYSA-N 0.000 description 1
- HVVRUQBMAZRKPJ-UHFFFAOYSA-N 1,3-dimethylimidazolium Chemical compound CN1C=C[N+](C)=C1 HVVRUQBMAZRKPJ-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- STCBHSHARMAIOM-UHFFFAOYSA-N 1-methyl-1h-imidazol-1-ium;chloride Chemical compound Cl.CN1C=CN=C1 STCBHSHARMAIOM-UHFFFAOYSA-N 0.000 description 1
- 238000004009 13C{1H}-NMR spectroscopy Methods 0.000 description 1
- UYKMYYAYPVQDMM-UHFFFAOYSA-O 2,3-bis(2-ethoxyethyl)-1h-imidazol-3-ium Chemical compound CCOCCC=1NC=C[N+]=1CCOCC UYKMYYAYPVQDMM-UHFFFAOYSA-O 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- ZNPQLXDWQPMSMR-UHFFFAOYSA-N 2-chloro-n-ethylethanamine;hydrochloride Chemical compound [Cl-].CC[NH2+]CCCl ZNPQLXDWQPMSMR-UHFFFAOYSA-N 0.000 description 1
- RAGSWDIQBBZLLL-UHFFFAOYSA-N 2-chloroethyl(diethyl)azanium;chloride Chemical compound Cl.CCN(CC)CCCl RAGSWDIQBBZLLL-UHFFFAOYSA-N 0.000 description 1
- MNNZINNZIQVULG-UHFFFAOYSA-N 2-chloroethylbenzene Chemical compound ClCCC1=CC=CC=C1 MNNZINNZIQVULG-UHFFFAOYSA-N 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 238000007341 Heck reaction Methods 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- NKERFCKSIIOGTM-UHFFFAOYSA-N [2-chloroethyl(phenyl)phosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(CCCl)C1=CC=CC=C1 NKERFCKSIIOGTM-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229940095054 ammoniac Drugs 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000010692 aromatic oil Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910002094 inorganic tetrachloropalladate Inorganic materials 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 239000005048 methyldichlorosilane Substances 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000009419 refurbishment Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, 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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19610908A DE19610908A1 (de) | 1996-03-20 | 1996-03-20 | Verfahren zur Herstellung heterocyclischer Carbene |
| TW086102643A TW412530B (en) | 1996-03-20 | 1997-03-05 | Process for preparing heterocyclic carbenes by reacting azolium salts with a deprotonation reagent in pure liquid ammonia or in pure organic amine and organic polar aprotic solvent |
| ZA9702198A ZA972198B (en) | 1996-03-20 | 1997-03-13 | Process for preparing heterocylic carbenes. |
| IDP970808A ID16265A (id) | 1996-03-20 | 1997-03-13 | Proses pembuatan senyawa karben heterosiklik |
| AU22878/97A AU710591B2 (en) | 1996-03-20 | 1997-03-14 | Process for preparing heterocyclic carbenes |
| BR9708234A BR9708234A (pt) | 1996-03-20 | 1997-03-14 | Processo para a preparaçÃo de carbenos heterociclicos |
| PL97329010A PL329010A1 (en) | 1996-03-20 | 1997-03-14 | Method of obtaining heterocyclic carbenes |
| EP97915369A EP0888308A1 (de) | 1996-03-20 | 1997-03-14 | Verfahren zur herstellung heterocyclischer carbene |
| JP9533129A JP2000507239A (ja) | 1996-03-20 | 1997-03-14 | ヘテロ環式カルベンの製造方法 |
| PCT/EP1997/001296 WO1997034875A1 (de) | 1996-03-20 | 1997-03-14 | Verfahren zur herstellung heterocyclischer carbene |
| KR10-1998-0707423A KR100492653B1 (ko) | 1996-03-20 | 1997-03-14 | 헤테로사이클릭카벤의제조방법 |
| CN97193968A CN1216536A (zh) | 1996-03-20 | 1997-03-14 | 制备杂环碳烯的方法 |
| CA002250086A CA2250086A1 (en) | 1996-03-20 | 1997-03-14 | Process for preparing heterocyclic carbenes |
| US09/155,065 US6025496A (en) | 1996-03-20 | 1997-03-14 | Process for preparing heterocyclic carbenes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19610908A DE19610908A1 (de) | 1996-03-20 | 1996-03-20 | Verfahren zur Herstellung heterocyclischer Carbene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19610908A1 true DE19610908A1 (de) | 1997-09-25 |
Family
ID=7788826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19610908A Withdrawn DE19610908A1 (de) | 1996-03-20 | 1996-03-20 | Verfahren zur Herstellung heterocyclischer Carbene |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6025496A (enExample) |
| EP (1) | EP0888308A1 (enExample) |
| JP (1) | JP2000507239A (enExample) |
| KR (1) | KR100492653B1 (enExample) |
| CN (1) | CN1216536A (enExample) |
| AU (1) | AU710591B2 (enExample) |
| BR (1) | BR9708234A (enExample) |
| CA (1) | CA2250086A1 (enExample) |
| DE (1) | DE19610908A1 (enExample) |
| ID (1) | ID16265A (enExample) |
| PL (1) | PL329010A1 (enExample) |
| TW (1) | TW412530B (enExample) |
| WO (1) | WO1997034875A1 (enExample) |
| ZA (1) | ZA972198B (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1115491A4 (en) * | 1998-09-10 | 2002-11-20 | Univ New Orleans Foundation | CATALYST COMPLEX WITH CARBEN LIGAND |
| DE102004060247A1 (de) * | 2004-12-15 | 2006-06-29 | Studiengesellschaft Kohle Mbh | Neue N-heterocyclische Carbene und ihre Anwendung in der Katalyse |
| EP2261217A1 (en) * | 2009-06-10 | 2010-12-15 | Politecnico di Milano | Imidazolium salts having liquid crystal characteristics, useful as electrolytes |
| US8403044B2 (en) | 2009-05-05 | 2013-03-26 | Stepan Company | Sulfonated internal olefin surfactant for enhanced oil recovery |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19815275B4 (de) | 1998-04-06 | 2009-06-25 | Evonik Degussa Gmbh | Alkylidenkomplexe des Rutheniums mit N-heterozyklischen Carbenliganden und deren Verwendung als hochaktive, selektive Katalysatoren für die Olefin-Metathese |
| US7285593B1 (en) | 1998-05-19 | 2007-10-23 | Advanced Polymer Technologies, Inc. | Polyolefin compositions optionally having variable toughness and/or hardness |
| FR2778916B1 (fr) * | 1998-05-20 | 2000-06-30 | Rhone Poulenc Fibres | Nouveaux complexes organometalliques comprenant des carbenes heterocycliques cationiques et leur procede de preparation |
| GB9814282D0 (en) | 1998-07-01 | 1998-09-02 | Borealis As | Catalysts |
| US6316380B1 (en) * | 1998-09-10 | 2001-11-13 | University Of New Orleans Research & Technology Foundation | Catalyst system comprising transition metal and imidazoline-2-ylidene or imidazolidine-2-ylidene |
| JP2002536468A (ja) | 1999-02-05 | 2002-10-29 | マテリア インコーポレイテッド | 表面へのポリマー接着を増強するためのメタセシス活性接着剤及び方法 |
| US20140088260A1 (en) | 1999-02-05 | 2014-03-27 | Materia, Inc. | Metathesis-active adhesion agents and methods for enhancing polymer adhesion to surfaces |
| BR0008022A (pt) | 1999-02-05 | 2001-11-06 | Materia Inc | Composições de poliolefina com densidade variável e processos para sua produção e uso |
| DE60039166D1 (de) * | 1999-03-31 | 2008-07-24 | California Inst Of Techn | Mit triazolydin-liganden koordinierte rutheniummetall-alkyliden-komplexe die hohe olefin-metathese-aktivität aufweisen |
| US7329758B1 (en) | 1999-05-24 | 2008-02-12 | California Institute Of Technology | Imidazolidine-based metal carbene metathesis catalysts |
| DE10025623A1 (de) * | 2000-05-24 | 2001-12-06 | Bayer Ag | Immobilisierte Palladiumkomplexe |
| WO2002038566A2 (en) * | 2000-11-10 | 2002-05-16 | The University Of Akron | Carbene porphyrins and carbene porphyrinoids for use in medical diagnosis and treatment |
| GB0031078D0 (en) * | 2000-12-20 | 2001-01-31 | Borealis Tech Oy | Compounds |
| US6838489B2 (en) * | 2001-03-23 | 2005-01-04 | Cymetech, Llc | High activity metal carbene metathesis catalysts generated using a thermally activated N-heterocyclic carbene precursor |
| DE60238829D1 (de) * | 2001-03-23 | 2011-02-17 | California Inst Of Techn | Unter verwendung eines thermisch aktivierten n-heterocyclischen carbenvorläufers gebildete hochaktive metallcarbenmetathesekatalysatoren |
| AU2003217232A1 (en) | 2002-02-04 | 2003-09-02 | Massachusetts Institute Of Technology | Transition-metal-catalyzed carbon-nitrogen bond-forming methods using carbene ligands |
| CN1835958A (zh) * | 2003-08-11 | 2006-09-20 | 默克专利有限公司 | 可被固定的n－杂环碳烯 |
| CA2537677C (en) * | 2003-09-05 | 2016-08-09 | The University Of Akron | Metal complexes of n-heterocyclic carbenes as radiopharmaceuticals and antibiotics |
| US8519146B2 (en) * | 2004-09-07 | 2013-08-27 | The University Of Akron | Metal complexes of N-heterocyclic carbenes as antibiotics |
| JP4680519B2 (ja) * | 2004-02-25 | 2011-05-11 | 株式会社きもと | イミダゾールカルベン金属錯体の製造方法 |
| JP4680518B2 (ja) * | 2004-02-25 | 2011-05-11 | 株式会社きもと | イミダゾールカルベン付加体の製造方法 |
| AU2008260203B2 (en) * | 2007-05-31 | 2013-05-02 | The University Of Akron | Metal complexes incorporated within biodegradable nanoparticles and their use |
| EP2173357A4 (en) * | 2007-07-23 | 2013-01-09 | Univ Akron | INTEGRATED METAL COMPLEXES AND THEIR USE IN BIODEGRADABLE NANOPARTICLES |
| AU2010233109B2 (en) * | 2009-04-09 | 2014-10-30 | California Institute Of Technology | Molecular sieves and related methods and structure directing agents |
| US8227371B2 (en) | 2010-09-24 | 2012-07-24 | Exxonmobil Chemical Patents Inc. | Class of olefin metathesis catalysts, methods of preparation, and processes for the use thereof |
| US9181360B2 (en) | 2011-08-12 | 2015-11-10 | Exxonmobil Chemical Patents Inc. | Polymers prepared by ring opening / cross metathesis |
| JP7100312B2 (ja) * | 2018-02-23 | 2022-07-13 | 東ソー株式会社 | 新規セリウム錯体、及び発光材 |
| KR102291885B1 (ko) | 2018-10-10 | 2021-08-23 | 한국생명공학연구원 | 카벤 화합물, 카벤-금속나노입자 복합체 및 이의 제조방법 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4230466A1 (de) * | 1992-09-11 | 1994-03-17 | Basf Ag | Verfahren zur katalytischen Herstellung von Kondensationsprodukten des Formaldehyds |
| DE4447066A1 (de) * | 1994-12-29 | 1996-07-04 | Hoechst Ag | Heterocyclische Carbene enthaltende Metallkomplexverbindungen |
-
1996
- 1996-03-20 DE DE19610908A patent/DE19610908A1/de not_active Withdrawn
-
1997
- 1997-03-05 TW TW086102643A patent/TW412530B/zh active
- 1997-03-13 ZA ZA9702198A patent/ZA972198B/xx unknown
- 1997-03-13 ID IDP970808A patent/ID16265A/id unknown
- 1997-03-14 JP JP9533129A patent/JP2000507239A/ja not_active Ceased
- 1997-03-14 AU AU22878/97A patent/AU710591B2/en not_active Ceased
- 1997-03-14 US US09/155,065 patent/US6025496A/en not_active Expired - Fee Related
- 1997-03-14 PL PL97329010A patent/PL329010A1/xx unknown
- 1997-03-14 BR BR9708234A patent/BR9708234A/pt not_active Application Discontinuation
- 1997-03-14 EP EP97915369A patent/EP0888308A1/de not_active Withdrawn
- 1997-03-14 KR KR10-1998-0707423A patent/KR100492653B1/ko not_active Expired - Fee Related
- 1997-03-14 CN CN97193968A patent/CN1216536A/zh active Pending
- 1997-03-14 WO PCT/EP1997/001296 patent/WO1997034875A1/de not_active Ceased
- 1997-03-14 CA CA002250086A patent/CA2250086A1/en not_active Abandoned
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1115491A4 (en) * | 1998-09-10 | 2002-11-20 | Univ New Orleans Foundation | CATALYST COMPLEX WITH CARBEN LIGAND |
| US7622590B1 (en) | 1998-09-10 | 2009-11-24 | University Of New Orleans Foundation | Catalyst complex with carbene ligand |
| US7902389B2 (en) | 1998-09-10 | 2011-03-08 | Nolan Steven P | Catalyst complex with carbene ligand |
| US8859779B2 (en) | 1998-09-10 | 2014-10-14 | Materia, Inc. | Catalyst complex with carbene ligand |
| US9233365B2 (en) | 1998-09-10 | 2016-01-12 | Materia, Inc. | Catalyst complex with carbene ligand |
| US9339805B2 (en) | 1998-09-10 | 2016-05-17 | Materia, Inc. | Catalyst complex with carbene ligand |
| DE102004060247A1 (de) * | 2004-12-15 | 2006-06-29 | Studiengesellschaft Kohle Mbh | Neue N-heterocyclische Carbene und ihre Anwendung in der Katalyse |
| US8403044B2 (en) | 2009-05-05 | 2013-03-26 | Stepan Company | Sulfonated internal olefin surfactant for enhanced oil recovery |
| EP2261217A1 (en) * | 2009-06-10 | 2010-12-15 | Politecnico di Milano | Imidazolium salts having liquid crystal characteristics, useful as electrolytes |
| WO2010142445A3 (en) * | 2009-06-10 | 2011-02-17 | Daunia Solar Cell S.R.L. | New imidazolium salts having liquid crystal characteristics, useful as electrolytes |
| US9932316B2 (en) | 2009-06-10 | 2018-04-03 | Daunia Solar Cell S.R.L. | Imidazolium salts having liquid crystal characteristics, useful as electrolytes |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2287897A (en) | 1997-10-10 |
| KR100492653B1 (ko) | 2005-11-11 |
| EP0888308A1 (de) | 1999-01-07 |
| CA2250086A1 (en) | 1997-09-25 |
| US6025496A (en) | 2000-02-15 |
| PL329010A1 (en) | 1999-03-01 |
| BR9708234A (pt) | 1999-08-03 |
| JP2000507239A (ja) | 2000-06-13 |
| ZA972198B (en) | 1997-09-17 |
| ID16265A (id) | 1997-09-18 |
| CN1216536A (zh) | 1999-05-12 |
| TW412530B (en) | 2000-11-21 |
| KR20000064700A (ko) | 2000-11-06 |
| AU710591B2 (en) | 1999-09-23 |
| WO1997034875A1 (de) | 1997-09-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE19610908A1 (de) | Verfahren zur Herstellung heterocyclischer Carbene | |
| EP1726593B1 (de) | Salze mit Cyanoborat-Anionen | |
| DE60209814T2 (de) | Verfahren zur herstellung von ionischen flüssigkeiten | |
| EP1177199B1 (de) | Ionische flüssigkeiten, ihre herstellung und ihre verwendung | |
| WO2008052861A2 (de) | Verfahren zur herstellung von 1,3 -hetero-aromatischen carbonaten | |
| DE2528211A1 (de) | Verfahren zur herstellung von acylcyaniden | |
| WO2004035542A1 (de) | Funktionalisierte ionische flüssigkeiten und verfahren zu ihrer herstellung | |
| EP2079707B1 (de) | Verfahren zur umsetzung von 1,3-hetero-aromatischen 2-carboxylaten mit wasser | |
| DE2634663B2 (de) | Verfahren zur Herstellung eines optisch aktiven Alkylchrysanthemummonocarbonsäureesters | |
| DE10229040A1 (de) | Neue Erdalkalimetallkomplexe und ihre Verwendung | |
| EP2079705A1 (de) | Verfahren zur herstellung quarternärer carbonate | |
| DE102016206303A1 (de) | Katalysator zur Hydroformylierung von Olefinen und dessen Verwendung | |
| EP1028938B1 (de) | Herstellung von aminohalogencrotonaten | |
| EP1824827B1 (de) | Verfahren zur herstellung von onium-salzen mit alkyl- oder arylsufonat-anionen oder alkyl- oder arylcarboxylat-anionen mit geringen halogenid-gehalt | |
| EP2678344B1 (de) | Cyclopropenyl-yliden stabilisierte phospheniumkationen | |
| DE2648005C2 (de) | Verfahren zur Herstellung N-substituierter 2-Carbamoylphosphinsäuren | |
| EP2513123B1 (de) | Verbindungen mit (perfluoralkyl)fluorohydrogenphosphat-anionen | |
| EP1831179B1 (de) | Verfahren zur herstellung von onium-salzen mit tetrafluoroborat-anion mit reduziertem halogenid-gehalt | |
| DE102004060073A1 (de) | Verfahren zur Hertellung von Onium-Salzen mit Tetrafluoroborat-Anion mit reduziertem Halogenid-Gehalt | |
| EP4635964A1 (de) | Verfahren zur herstellung metallorganischer verbindungen | |
| EP2303902B1 (de) | Bis(perfluoralkyl)phosphinige säuren und derivate sowie deren anwendung | |
| EP2220100A2 (de) | Chirale cycloplatinierte komplexe, herstellungsverfahren sowie deren verwendung in medizin und katalyse | |
| EP0484855A2 (de) | Verfahren zur Herstellung von 3-Aminocrotonnitril | |
| DE3035549C2 (enExample) | ||
| EP3908589A1 (de) | Metallorganische verbindungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: CELANESE GMBH, 60439 FRANKFURT, DE |
|
| 8127 | New person/name/address of the applicant |
Owner name: CELANESE CHEMICALS EUROPE GMBH, 60439 FRANKFURT, D |
|
| 8141 | Disposal/no request for examination |