CH633806A5 - Verfahren zur herstellung von doppelylid-komplexen von metallen und deren verwendung. - Google Patents
Verfahren zur herstellung von doppelylid-komplexen von metallen und deren verwendung. Download PDFInfo
- Publication number
- CH633806A5 CH633806A5 CH28378A CH28378A CH633806A5 CH 633806 A5 CH633806 A5 CH 633806A5 CH 28378 A CH28378 A CH 28378A CH 28378 A CH28378 A CH 28378A CH 633806 A5 CH633806 A5 CH 633806A5
- Authority
- CH
- Switzerland
- Prior art keywords
- dimethyl
- bis
- phosphorane
- methylene
- formula
- Prior art date
Links
- 229910052751 metal Inorganic materials 0.000 title claims description 14
- 239000002184 metal Substances 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 150000002739 metals Chemical class 0.000 title claims 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 33
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 claims description 32
- YOTZYFSGUCFUKA-UHFFFAOYSA-N dimethylphosphine Chemical compound CPC YOTZYFSGUCFUKA-UHFFFAOYSA-N 0.000 claims description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 14
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 239000011777 magnesium Substances 0.000 claims description 11
- 229910052763 palladium Inorganic materials 0.000 claims description 10
- 229910052793 cadmium Inorganic materials 0.000 claims description 9
- 229910052759 nickel Inorganic materials 0.000 claims description 9
- 239000011701 zinc Substances 0.000 claims description 9
- 229910052744 lithium Inorganic materials 0.000 claims description 8
- 229910052749 magnesium Inorganic materials 0.000 claims description 8
- 229910052697 platinum Inorganic materials 0.000 claims description 8
- 229910052725 zinc Inorganic materials 0.000 claims description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229910052733 gallium Inorganic materials 0.000 claims description 7
- 239000010931 gold Substances 0.000 claims description 7
- 229910052738 indium Inorganic materials 0.000 claims description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- 229910052737 gold Inorganic materials 0.000 claims description 5
- -1 M" for AI Inorganic materials 0.000 claims description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 9
- 238000002360 preparation method Methods 0.000 claims 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims 2
- 229910052716 thallium Inorganic materials 0.000 claims 2
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- 101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- VYFNWYLJPQZRCG-UHFFFAOYSA-N nickel;trimethylphosphane Chemical compound [Ni].CP(C)C.CP(C)C VYFNWYLJPQZRCG-UHFFFAOYSA-N 0.000 claims 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 5
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- XCZXGTMEAKBVPV-UHFFFAOYSA-N trimethylgallium Chemical compound C[Ga](C)C XCZXGTMEAKBVPV-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- KYHNNWWCXIOTKC-UHFFFAOYSA-L nickel(2+);trimethylphosphane;dichloride Chemical compound Cl[Ni]Cl.CP(C)C.CP(C)C KYHNNWWCXIOTKC-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- VYRLPDUIQPFWPC-UHFFFAOYSA-N trimethylthallane Chemical compound C[Tl](C)C VYRLPDUIQPFWPC-UHFFFAOYSA-N 0.000 description 2
- AUFHQOUHGKXFEM-UHFFFAOYSA-N C[Au]C Chemical compound C[Au]C AUFHQOUHGKXFEM-UHFFFAOYSA-N 0.000 description 1
- 229910003803 Gold(III) chloride Inorganic materials 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- RYLVUVITEOLDSM-UHFFFAOYSA-M bis(trimethyl-$l^{5}-phosphanylidene)azanium;chloride Chemical compound [Cl-].CP(C)(C)=[N+]=P(C)(C)C RYLVUVITEOLDSM-UHFFFAOYSA-M 0.000 description 1
- VQNPSCRXHSIJTH-UHFFFAOYSA-N cadmium(2+);carbanide Chemical group [CH3-].[CH3-].[Cd+2] VQNPSCRXHSIJTH-UHFFFAOYSA-N 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical group CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- RJHLTVSLYWWTEF-UHFFFAOYSA-K gold trichloride Chemical compound Cl[Au](Cl)Cl RJHLTVSLYWWTEF-UHFFFAOYSA-K 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- QWDJLDTYWNBUKE-UHFFFAOYSA-L magnesium bicarbonate Chemical compound [Mg+2].OC([O-])=O.OC([O-])=O QWDJLDTYWNBUKE-UHFFFAOYSA-L 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012982 x-ray structure analysis Methods 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2701143A DE2701143C2 (de) | 1977-01-13 | 1977-01-13 | Doppelylid-Komplexe von Metallen sowie Verfahren zu ihrer Herstellung und deren Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH633806A5 true CH633806A5 (de) | 1982-12-31 |
Family
ID=5998574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH28378A CH633806A5 (de) | 1977-01-13 | 1978-01-11 | Verfahren zur herstellung von doppelylid-komplexen von metallen und deren verwendung. |
Country Status (6)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4537982A (en) * | 1982-08-03 | 1985-08-27 | Bayer Aktiengesellschaft | Production of organic nickel compounds |
| DE3336500A1 (de) * | 1983-10-07 | 1985-04-25 | Bayer Ag, 5090 Leverkusen | Organische nickel-verbindungen deren herstellung und verwendung als katalysatoren bei der polymerisation von olefinen |
| US4906754A (en) * | 1985-10-15 | 1990-03-06 | E. I. Du Pont De Nemours And Company | Nickel catalysts for copolymerization of ethylene |
| US5030606A (en) * | 1985-10-15 | 1991-07-09 | E. I. Du Pont De Nemours And Company | Nickel-catalyzed copolymerization of ethylene |
| US4716205A (en) * | 1985-10-15 | 1987-12-29 | E. I. Du Pont De Nemours And Company | Nickel-catalyzed polymerization of ethylene |
| US5175326A (en) * | 1985-10-15 | 1992-12-29 | E. I. Du Pont De Nemours And Company | Nickel containing organo-metallic compound as catalyst |
| US4698403A (en) * | 1985-10-15 | 1987-10-06 | E. I. Du Pont De Nemours And Company | Nickel-catalyzed copolymerization of ethylene |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2998416A (en) | 1960-06-23 | 1961-08-29 | Cities Service Res & Dev Co | Ylide-transition metal compound catalyst system, process of making and method of using |
| US3414624A (en) * | 1967-03-01 | 1968-12-03 | Procter & Gamble | Alkali metalated tertiary phosphines and the preparation thereof |
| US3686159A (en) | 1969-12-19 | 1972-08-22 | Shell Oil Co | Ethylene polymerization |
| DE2557611A1 (de) * | 1975-12-20 | 1977-06-30 | Hoechst Ag | Trimethylphosphinimino-dimethylmethylen-phosphoran und verfahren zu seiner herstellung |
| CH630928A5 (de) * | 1976-03-25 | 1982-07-15 | Hoechst Ag | Verfahren zur herstellung von doppelylid-komplexen von metallen. |
-
1977
- 1977-01-13 DE DE2701143A patent/DE2701143C2/de not_active Expired
-
1978
- 1978-01-09 GB GB695/78A patent/GB1578584A/en not_active Expired
- 1978-01-11 CH CH28378A patent/CH633806A5/de not_active IP Right Cessation
- 1978-01-12 ZA ZA00780189A patent/ZA78189B/xx unknown
- 1978-01-12 US US05/868,830 patent/US4185028A/en not_active Expired - Lifetime
- 1978-01-13 FR FR7800982A patent/FR2377413A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB1578584A (en) | 1980-11-05 |
| US4185028A (en) | 1980-01-22 |
| FR2377413A1 (fr) | 1978-08-11 |
| DE2701143A1 (de) | 1978-07-20 |
| ZA78189B (en) | 1979-01-31 |
| FR2377413B1 (US06373033-20020416-M00071.png) | 1982-04-09 |
| DE2701143C2 (de) | 1985-08-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |