DE1593535A1 - Neue Komplexe von UEbergangsmetallen mit Cyclooctatetraen und Verfahren zu ihrer Herstellung - Google Patents
Neue Komplexe von UEbergangsmetallen mit Cyclooctatetraen und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1593535A1 DE1593535A1 DE19661593535 DE1593535A DE1593535A1 DE 1593535 A1 DE1593535 A1 DE 1593535A1 DE 19661593535 DE19661593535 DE 19661593535 DE 1593535 A DE1593535 A DE 1593535A DE 1593535 A1 DE1593535 A1 DE 1593535A1
- Authority
- DE
- Germany
- Prior art keywords
- cyclooctatetraene
- transition metals
- metals
- complexes
- vanadium
- 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- Withdrawn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 description 24
- 229910052723 transition metal Inorganic materials 0.000 title claims description 13
- 150000003624 transition metals Chemical class 0.000 title claims description 13
- KDUIUFJBNGTBMD-VXMYFEMYSA-N cyclooctatetraene Chemical compound C1=C\C=C/C=C\C=C1 KDUIUFJBNGTBMD-VXMYFEMYSA-N 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title description 3
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000011651 chromium Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- 229910052720 vanadium Inorganic materials 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 229910052804 chromium Inorganic materials 0.000 claims description 6
- 229910052750 molybdenum Inorganic materials 0.000 claims description 5
- 150000004945 aromatic hydrocarbons Chemical group 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 4
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- 239000010937 tungsten Substances 0.000 claims description 4
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 239000011733 molybdenum Substances 0.000 claims description 3
- 150000004292 cyclic ethers Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 2
- 235000019227 E-number Nutrition 0.000 claims 1
- 239000004243 E-number Substances 0.000 claims 1
- 108010000178 IGF-I-IGFBP-3 complex Proteins 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- KDUIUFJBNGTBMD-DLMDZQPMSA-N [8]annulene Chemical compound C/1=C/C=C\C=C/C=C\1 KDUIUFJBNGTBMD-DLMDZQPMSA-N 0.000 description 16
- 239000013078 crystal Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- HCVBQHPZZTZJFD-UHFFFAOYSA-N [Na].[Na].C1=CC=CC=CC=C1 Chemical compound [Na].[Na].C1=CC=CC=CC=C1 HCVBQHPZZTZJFD-UHFFFAOYSA-N 0.000 description 9
- XTAUTDONELMCTN-UHFFFAOYSA-N cyclooctatetraene;potassium Chemical compound [K].[K].C1=CC=CC=CC=C1 XTAUTDONELMCTN-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000002736 metal compounds Chemical class 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000010936 titanium Substances 0.000 description 4
- 229910021556 Chromium(III) chloride Inorganic materials 0.000 description 3
- 229960000359 chromic chloride Drugs 0.000 description 3
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 3
- -1 complex metal hydrides Chemical class 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 150000003623 transition metal compounds Chemical class 0.000 description 3
- 229910021551 Vanadium(III) chloride Inorganic materials 0.000 description 2
- 150000001339 alkali metal compounds Chemical class 0.000 description 2
- 229910001508 alkali metal halide Inorganic materials 0.000 description 2
- 150000008045 alkali metal halides Chemical class 0.000 description 2
- LGQRLOKNAKSVOX-UHFFFAOYSA-N cyclooctatetraene nickel Chemical compound [Ni].C1=CC=CC=CC=C1 LGQRLOKNAKSVOX-UHFFFAOYSA-N 0.000 description 2
- VHOUAJIBVFBZLU-UHFFFAOYSA-N cyclooctatetraene titanium Chemical compound [Ti].C1=CC=CC=CC=C1.C1=CC=CC=CC=C1 VHOUAJIBVFBZLU-UHFFFAOYSA-N 0.000 description 2
- 150000004306 cyclooctatetraenes Chemical class 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- HQYCOEXWFMFWLR-UHFFFAOYSA-K vanadium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[V+3] HQYCOEXWFMFWLR-UHFFFAOYSA-K 0.000 description 2
- MROJXXOCABQVEF-UHFFFAOYSA-N Actarit Chemical compound CC(=O)NC1=CC=C(CC(O)=O)C=C1 MROJXXOCABQVEF-UHFFFAOYSA-N 0.000 description 1
- GWKAILYHPJPIGY-UHFFFAOYSA-N C1=CC=CC=CC=C1.[Co] Chemical compound C1=CC=CC=CC=C1.[Co] GWKAILYHPJPIGY-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- IHAQLRVAXPKNCB-UHFFFAOYSA-N cyclooctatetraene iron Chemical compound [Fe].C1=CC=CC=CC=C1 IHAQLRVAXPKNCB-UHFFFAOYSA-N 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical compound [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- GICWIDZXWJGTCI-UHFFFAOYSA-I molybdenum pentachloride Chemical compound Cl[Mo](Cl)(Cl)(Cl)Cl GICWIDZXWJGTCI-UHFFFAOYSA-I 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 150000003112 potassium compounds Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 150000005672 tetraenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEST025089 | 1966-03-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1593535A1 true DE1593535A1 (de) | 1970-08-13 |
Family
ID=7460400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661593535 Withdrawn DE1593535A1 (de) | 1966-03-09 | 1966-03-09 | Neue Komplexe von UEbergangsmetallen mit Cyclooctatetraen und Verfahren zu ihrer Herstellung |
Country Status (8)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4120882A (en) * | 1959-12-22 | 1978-10-17 | Studiengesellschaft Kohle M.B.H. | Metal complexes |
| US3932477A (en) * | 1974-06-13 | 1976-01-13 | E. I. Du Pont De Nemours And Company | Cyclooctatetraene complexes of niobium and tantalum |
| GB2055838A (en) * | 1979-08-15 | 1981-03-11 | Inventa Ag | Process for the preparation of cobaltocene |
| DE3030055A1 (de) * | 1980-08-08 | 1982-03-25 | Basf Ag, 6700 Ludwigshafen | Verfahren zum herstellen von ethylen-homopolymerisaten sowie ethylen-copolymerisaten mit (alpha) -monoolefinen |
| GB2450878A (en) * | 2007-07-10 | 2009-01-14 | Nexia Solutions Ltd | Metal sandwich compounds and their use for binding gases |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3068258A (en) * | 1958-09-22 | 1962-12-11 | Union Carbide Corp | Process for producing arene hydrocarbon-transition metal compounds |
| US3297756A (en) * | 1963-07-19 | 1967-01-10 | Du Pont | Cyclononatetraenide salts and process of preparing |
-
1966
- 1966-03-09 DE DE19661593535 patent/DE1593535A1/de not_active Withdrawn
-
1967
- 1967-02-24 GB GB8941/67A patent/GB1128128A/en not_active Expired
- 1967-02-28 NL NL6703228A patent/NL6703228A/xx unknown
- 1967-03-02 CH CH308467A patent/CH483453A/de not_active IP Right Cessation
- 1967-03-06 BE BE695085D patent/BE695085A/xx unknown
- 1967-03-07 FR FR97824A patent/FR1513195A/fr not_active Expired
- 1967-03-07 US US621115A patent/US3450728A/en not_active Expired - Lifetime
- 1967-03-08 SE SE03188/67A patent/SE326956B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3450728A (en) | 1969-06-17 |
| NL6703228A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-09-11 |
| CH483453A (de) | 1969-12-31 |
| GB1128128A (en) | 1968-09-25 |
| FR1513195A (fr) | 1968-02-09 |
| SE326956B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-08-10 |
| BE695085A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-09-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |