DE1102735B - Process for the production of organic complex compounds containing titanium and aluminum - Google Patents
Process for the production of organic complex compounds containing titanium and aluminumInfo
- Publication number
- DE1102735B DE1102735B DEB56437A DEB0056437A DE1102735B DE 1102735 B DE1102735 B DE 1102735B DE B56437 A DEB56437 A DE B56437A DE B0056437 A DEB0056437 A DE B0056437A DE 1102735 B DE1102735 B DE 1102735B
- Authority
- DE
- Germany
- Prior art keywords
- aluminum
- parts
- titanium
- complex compounds
- production
- 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.)
- Pending
Links
- 229910052782 aluminium Inorganic materials 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 title description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 title description 6
- 229910052719 titanium Inorganic materials 0.000 title description 5
- 239000010936 titanium Substances 0.000 title description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 4
- -1 aluminum halide Chemical class 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 7
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 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
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010792 warming 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/28—Titanium 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Verfahren zur Herstellung von Titan und Aluminium enthaltenden organischen Komplexverbindungen Die Herstellung von Titan und Aluminium enthaltenden organischen Komplexverbindungen der allgemeinen Formel (C5H5)2TiX2AlRmXn in der R einen Alkylrest, X Halogen, m = 1 oder 2, n = O oder 1 und m + n =2 bedeutet, durch Umsetzung von Bis-(cyclopentadienyl)-titanhalogeniden mit einem Überschuß an Aluminiumtrialkyl oder Aluminium alkylchloriden, ist bekannt. Process for the production of titanium and aluminum containing organic Complex compounds The production of titanium and aluminum containing organic Complex compounds of the general formula (C5H5) 2TiX2AlRmXn in which R is an alkyl radical, X signifies halogen, m = 1 or 2, n = O or 1 and m + n = 2, by reacting Bis (cyclopentadienyl) titanium halides with an excess of aluminum trialkyl or aluminum alkyl chlorides is known.
Dieses Verfahren benötigt als Ausgangssubstanzen die relativ schlecht darzustellenden Bis- (cyclopentadienyl) -titanhalogenide sowie einen großen Überschuß an Aluminiumalkylen. This process requires the relatively poor starting substances bis (cyclopentadienyl) titanium halides to be prepared and a large excess of aluminum alkyls.
Es wurde nun gefunden, daß man die obengenannten Komplexverbindungen, in denen m = O, 1 oder 2, n = 0, 1 oder 2 und n + m = 2 bedeutet, ohne Verwendung von Bis-(cyclopentadienyl)-titanhalogeniden in einfacher Weise und in sehr guten Ausbeuten erhält wenn man Titan(III)-halogenide mit (Alkyl)-aluminiumcyclopentadienylen bzw. deren Komplexverbindungen mit Alkalicyclopentadienylen umsetzt. It has now been found that the above complex compounds, in which m = 0, 1 or 2, n = 0, 1 or 2 and n + m = 2, without use of bis (cyclopentadienyl) titanium halides in a simple manner and in very good ways Yields are obtained when titanium (III) halides are obtained with (alkyl) aluminum cyclopentadienylene or their complex compounds with alkali cyclopentadienylene.
Da sich die Aluminiumcyclopentadienylverbindungen im Gegensatz zu den Titancyclopentadienylverbindungen sehr leicht aus den entsprechenden (Alkyl)-aluminiumhalogeniden und Natriumcyclopentadienyl bilden, ist es nicht notwendig, die Aluminiumcyclopentadienyle in isolierter Form einzusetzen, sondern man kann auch die Ausgangskomponenten verwenden. In diesem Falle verfährt man so, daß man zunächst Titan(III)-chlorid und Natriumcyclopentadienyl in einem indifferenten Lösungsmittel, wie Benzol, Heptan und Cyclohexan, suspendiert vorlegt. Anschließend setzt man die Aluminiumverbindung zu, wobei sich sofort in exothermer Reaktion in situ die Aluminiumcyclopentadienylverbindung bildet und aus dieser dann die Titan-Aluminium-Verbindung. Die Umsetzungen verlaufen also beispielsweise nach folgenden Gleichungen: Die Reaktionstemperatur kann zwischen etwa 10 und 1300C liegen. Da die entstehenden Komplexverbindungen in Kohlenwasserstoffen löslich sind, bereitet die Abtrennung des gebildeten Natriumchlorids keinerlei Schwierigkeiten.Since the aluminum cyclopentadienyl compounds, in contrast to the titanium cyclopentadienyl compounds, are formed very easily from the corresponding (alkyl) aluminum halides and sodium cyclopentadienyl, it is not necessary to use the aluminum cyclopentadienyls in isolated form; the starting components can also be used. In this case, the procedure is that titanium (III) chloride and sodium cyclopentadienyl are initially suspended in an inert solvent such as benzene, heptane and cyclohexane. The aluminum compound is then added, and the aluminum cyclopentadienyl compound is immediately formed in an exothermic reaction in situ and then the titanium-aluminum compound is formed from this. The conversions run according to the following equations, for example: The reaction temperature can be between about 10 and 130.degree. Since the complex compounds formed are soluble in hydrocarbons, the separation of the sodium chloride formed presents no difficulties whatsoever.
Die erfindungsgemäß hergestellten Verbindungen sind als Katalysatoren in der organischen Chemie geeignet, beispielsweise als Katalysatoren für die Polymerisation von Olefinen. The compounds prepared according to the invention are used as catalysts suitable in organic chemistry, for example as catalysts for polymerization of olefins.
Die in den folgenden Beispielen genannten Teile sind Gewichtsteile. The parts mentioned in the following examples are parts by weight.
Beispiel 1 Zu einer Suspension von 154 Teilen Titan(III)-chlorid in 300 Teilen Heptan läßt man unter Rühren sowie unter Luft- und Feuchtigkeitsausschluß 300 Teile Diäthyl- aluminiumcyclopentadienyl zufließen. Die Mischung erwärmt sich dabei, und das Titan(III)-chlorid geht mit blauer Farbe in Lösung. Man erwärmt noch 1 Stunde auf 80"C und kühlt dann auf -50"C ab. Es scheiden sich blaue Kristalle aus, die man abfiltriert und aus Heptan umkristallisiert. Man erhält etwa 300 Teile der Verbindung (C5 H5)2TiCl2Al(C2 H5)2 in Form blauer Kristalle, die einen Schmelzpunkt von 120 bis 121"C aufweisen. Example 1 To a suspension of 154 parts of titanium (III) chloride in 300 parts of heptane is left with stirring and with the exclusion of air and moisture 300 parts diethyl aluminum cyclopentadienyl flow into it. The mixture heats up at the same time, and the titanium (III) chloride goes into solution with a blue color. You are still warming up 1 hour to 80 "C and then cools to -50" C. Blue crystals separate from, which is filtered off and recrystallized from heptane. About 300 parts are obtained the compound (C5 H5) 2TiCl2Al (C2 H5) 2 in the form of blue crystals that have a melting point from 120 to 121 "C.
Beispiel 2 Wie im Beispiel 1 angegeben, werden 154 Teile Titan(III)-chlorid mit 186 Teilen Dicyclopentadienylaluminiumäthyl in 400 Teilen Heptan umgesetzt. Es werden 310 Teile (C5H5)2TiCl2Al(C2H5)Cl in Form grünblauer Kristalle erhalten. Example 2 As indicated in Example 1, 154 parts of titanium (III) chloride are used with 186 parts of dicyclopentadienylaluminum ethyl in 400 parts of heptane implemented. There are 310 parts of (C5H5) 2TiCl2Al (C2H5) Cl in the form of green-blue crystals obtain.
Beispiel 3 Zu 154 Teilen Titan(III)-chlorid, die in 400 Teilen Octan suspendiert sind, gibt man in drei bis vier Portionen 240 Teile Na[Al(C2H5)2(C5H5)2] in gepulverter Form. Nach jeder Zugabe setzt sofort die Reaktion ein. Nach Ende der Zugabe erhitzt man noch 1 bis 2 Stunden auf 80"C, filtriert heiß und kühlt die blaue Lösung auf -40 bis -50 C ab. Die erhaltenen Kristalle werden durch Umkristallisieren aus Octan gereinigt. Man erhält etwa 300 Teile (C5H5)2TiC12Al(C2H6)2 Beispiel 4 In einem Rührgefäß legt man 176 Teile Natriumcyclopentadienyl und 154 Teile Titan(III)-chlorid in 400 Teilen Heptan vor. Unter Rühren läßt man anschließend 125 Teile Diäthylaluminiumchlorid so schnell zulaufen, daß die Temperatur bei der sofort einsetzenden Reaktion nicht über 90°C ansteigt. Nach Aufarbeitung wie im Beispiel 3 erhält man etwa 300 Teile |(CoHs)2TiCl2Al(C2H)2 Beispiel 5 Wie im Beispiel 4 angegeben, werden 176 Teile Natriumcyclopentadienyl und 154 Teile Titan(III)-chlorid mit 134 Teilen Aluminiumchlorid umgesetzt. Anschließend zieht man das Lösungsmittel im Vakuum ab und extrahiert den grünblauen Rückstand mit heißem Heptan. Example 3 To 154 parts of titanium (III) chloride, that in 400 parts of octane are suspended, 240 parts of Na [Al (C2H5) 2 (C5H5) 2] are added in three to four portions. in powdered form. The reaction starts immediately after each addition. After the end The addition is heated to 80 "C for 1 to 2 hours, filtered hot and cooled blue solution to -40 to -50 C. The obtained crystals are made by recrystallization purified from octane. About 300 parts of (C5H5) 2TiC12Al (C2H6) 2 Example 4 are obtained 176 parts of sodium cyclopentadienyl and 154 parts of titanium (III) chloride are placed in a stirred vessel in 400 parts of heptane. 125 parts of diethylaluminum chloride are then left with stirring run up so quickly that the temperature does not occur in the reaction which starts immediately rises above 90 ° C. After working up as in Example 3, about 300 parts are obtained | (CoHs) 2TiCl2Al (C2H) 2 Example 5 As indicated in Example 4, 176 parts of sodium cyclopentadienyl are used and 154 parts of titanium (III) chloride reacted with 134 parts of aluminum chloride. Afterward the solvent is drawn off in vacuo and the green-blue residue is extracted with hot heptane.
Man erhält etwa 250 Teile (C5H5)2TiCl2AlCl2 in Form grünblauer Kristalle.About 250 parts of (C5H5) 2TiCl2AlCl2 are obtained in the form of green-blue crystals.
PATENTANSPROCHE: 1. Verfahren zur Herstellung von Titan und Aluminium enthaltenden organischen Komplexverbindungen der allgemeinen Formel (C5 H5)2Ti X2Al RmXn in der R einen Alkylrest, X Halogen, ni = 0, 1 oder 2, = = 0, 1 oder 2 und n + i71 = 2 bedeutet, dadurch gekennzeichnet, daß man Titan(III)-halogenide mit (Alkyl) - aluminiumcyclopentadienylen bzw. deren Komplexverbindungen mit Alkalicyclopentadienylen umsetzt. PATENT CLAIM: 1. Process for the production of titanium and aluminum containing organic complex compounds of the general formula (C5 H5) 2Ti X2Al RmXn in which R is an alkyl radical, X is halogen, ni = 0, 1 or 2, = = 0, 1 or 2 and n + i71 = 2 means, characterized in that titanium (III) halides are used with (Alkyl) aluminum cyclopentadienyls or their complex compounds with alkali cyclopentadienyls implements.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB56437A DE1102735B (en) | 1960-01-29 | 1960-01-29 | Process for the production of organic complex compounds containing titanium and aluminum |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB56437A DE1102735B (en) | 1960-01-29 | 1960-01-29 | Process for the production of organic complex compounds containing titanium and aluminum |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1102735B true DE1102735B (en) | 1961-03-23 |
Family
ID=6971330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB56437A Pending DE1102735B (en) | 1960-01-29 | 1960-01-29 | Process for the production of organic complex compounds containing titanium and aluminum |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1102735B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1153750B (en) | 1961-03-08 | 1963-09-05 | Basf Ag | Process for the production of organic complex compounds containing titanium (ó�) and aluminum |
-
1960
- 1960-01-29 DE DEB56437A patent/DE1102735B/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1153750B (en) | 1961-03-08 | 1963-09-05 | Basf Ag | Process for the production of organic complex compounds containing titanium (ó�) and aluminum |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1037446B (en) | Process for the production of organometallic titanium compounds | |
| DE1102735B (en) | Process for the production of organic complex compounds containing titanium and aluminum | |
| DE947475C (en) | Process for the preparation of new hexaorganoaethynyldisilanes | |
| DE1618677A1 (en) | Process for the preparation of tricyclohexyltin hydroxide | |
| DE1156809B (en) | Process for the preparation of cyanoalkylfluorosilanes | |
| DE1083819B (en) | Process for the preparation of tetraorganotin compounds | |
| EP0158163A1 (en) | Preparation of organo-tin halogenides by catalytic redistribution of higher alkylated organo-tin compounds with lower alkylated ones | |
| DE1178431B (en) | Process for the preparation of polymeric tin alkylene chlorides | |
| DE1172263B (en) | Process for the production of titanium (ó�) -aluminum halide aromatic complexes | |
| DE1154476B (en) | Process for the production of aluminum compounds of acetylene | |
| DE1200817B (en) | Process for the preparation of onium salt complex compounds | |
| DE2141765A1 (en) | 4-chloro-4-thiazolin-2-ones - with microbicidal properties | |
| DE1236518B (en) | Process for the preparation of tetraalkylammonium alanates | |
| DE622357C (en) | Process for the preparation of tertiary nitriles | |
| EP0010281B1 (en) | Process for preparing alpha, beta-dihalogeno-alkyl isocyanates | |
| DE877306C (en) | Process for the production of organosilicon compounds | |
| EP0718303A1 (en) | Process for the preparation of transition metal complexes with disubstituted cyclopentadiene ligands | |
| AT290531B (en) | Process for the preparation of new imidazolidine derivatives and their salts | |
| DE2429757C3 (en) | Process for the preparation of 3-hexyn-1-ol | |
| DE1153750B (en) | Process for the production of organic complex compounds containing titanium (ó�) and aluminum | |
| AT215429B (en) | Process for the production of new ferrocene derivatives | |
| DE1052986B (en) | Process for the preparation of organoboron compounds | |
| DE1140934B (en) | Process for the production of alkyl boron hydrocarbons | |
| DE1277258B (en) | Process for the preparation of mixtures of carbonylsulfonylimides | |
| DE1089382B (en) | Process for the preparation of titanium alkyl compounds |