DE1039055B - Polymerization catalysts and processes for their preparation - Google Patents
Polymerization catalysts and processes for their preparationInfo
- Publication number
- DE1039055B DE1039055B DEZ5928A DEZ0005928A DE1039055B DE 1039055 B DE1039055 B DE 1039055B DE Z5928 A DEZ5928 A DE Z5928A DE Z0005928 A DEZ0005928 A DE Z0005928A DE 1039055 B DE1039055 B DE 1039055B
- Authority
- DE
- Germany
- Prior art keywords
- polymerization catalysts
- preparation
- diesel oil
- processes
- titanium
- 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
- 239000002685 polymerization catalyst Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052719 titanium Inorganic materials 0.000 claims description 5
- 239000010936 titanium Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000002283 diesel fuel Substances 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- MXTOFRMIIQQSOE-UHFFFAOYSA-N butane;titanium(4+) Chemical compound [Ti+4].CCC[CH2-].CCC[CH2-].CCC[CH2-].CCC[CH2-] MXTOFRMIIQQSOE-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical class CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- ZGSOBQAJAUGRBK-UHFFFAOYSA-N propan-2-olate;zirconium(4+) Chemical compound [Zr+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-] ZGSOBQAJAUGRBK-UHFFFAOYSA-N 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Description
Polymerisationskatalysatoren und Verfahren zu deren Herstellung Die Erfindung bezieht sich auf die Herstellung von Poly merisationskatalysatoren.Polymerization catalysts and processes for their preparation Invention relates to the production of polymerization catalysts.
Der Erfinder hat bereits in zahlreichen. Patentschriften und Veröffentlichungen Katalysatoren beschrieben, die aus Verbindungen der Metalle der Untergruppen der IV. bis VI. Gruppe des Periodischen Systems einschließlich Thorium und Uran einerseits und aus metallorganischen Verbindungen insbesondere des Aluminiums, Magnesiums und. Zinks hergestellt werden. Diese großen Gruppen von Katalysatoren sind vornehmlich für die Herstellung von hochmolekularen kunststoffartigen Polymerisaten aus Olefinen, geeignet.The inventor has already worked in numerous. Patents and publications Catalysts described, which consist of compounds of the metals of the subgroups of IV. To VI. Group of the Periodic Table including Thorium and Uranium on the one hand and from organometallic compounds in particular of aluminum, magnesium and. Zinc are made. These large groups of catalysts are predominant for the production of high molecular weight plastic-like polymers from olefins, suitable.
Es wurde die überraschende Erfindung gemacht, daß sich unter dieser großen Gruppe von. Katalysatoren bestimmte eng begrenzte Kombinationen befinden, die zwar ebenfalls polymerisierend, jedoch selektiv derart wirken, daß sie Äthylen und andere Monoolefine nicht zu hochmolekularen Produkten, sondern nur zu dimeren oder niedrigpolymeren Produkten polymerisieren, während mit Diolefinen. hochmolekulare Polymerisate erhalten, werden.The surprising invention was made that under this large group of. Catalysts are in certain narrowly defined combinations, which also polymerize, but act selectively in such a way that they are ethylene and other monoolefins not to high molecular weight products, but only to dimeric ones or polymerize low polymer products while using diolefins. high molecular weight Polymers obtained are.
Die Herstellung dieser neuen Katalysatoren erfolgt dadurch, daß man Aluminiumtrialkyle mit Titan-oder Zirkonsäureestern unter Ausschluß von Luft zusammenbringt. Zweckmäßig werden diese Bestandteile in Gegenwart eines Lösungsmittels zusammengebracht, als welches aliphatische oder aromatische Kohlenwasserstoffe, z. B. ein Fischer-Tropsch-Dieselöl, Dieselöl oder auch Benzol verwendet werden können.The preparation of these new catalysts is carried out by Aluminum trialkyls with titanium or zirconic acid esters in the absence of air. These components are expediently brought together in the presence of a solvent, as which aliphatic or aromatic hydrocarbons, e.g. B. a Fischer-Tropsch diesel oil, Diesel oil or even benzene can be used.
Die neuen Ka:talvsatoren können beispielsweise zur Dimerisation von Äthylen zu Butylen, oder von Propylen zu 2- und 4-Methylpentenen-(1) oder zur Mischdimerisation von Äthylen. mit Propylen zu Gemischen von Methyl-butenen und -pentenen oder zur Polymerisation von Acetylen zu Cupren neben Benzol, von Propin zu öligen. und festen Produkten, von Butadien zu hochmolekulare : 1,2-Polymeren, von Isopren zu hochmolekularen 3,4-Polymeren Verwendung finden.The new Ka: talvsatoren can, for example, for the dimerization of Ethylene to butylene, or from propylene to 2- and 4-methylpentene- (1) or mixed dimerization of ethylene. with propylene to form mixtures of methyl butenes and pentenes or to Polymerization of acetylene to cuprene in addition to benzene, of propyne to oily. and fixed Products, from butadiene to high molecular: 1,2-polymers, from isoprene to high molecular Find 3,4-polymers use.
Die Verwendung der erfin.dungsgetnäßen Katalysatoren für diese Polymerisationen wird hier nicht beansprucht.The use of the catalysts according to the invention for these polymerizations is not claimed here.
Beispiel 1 250 ccm Fischer-Tropsch-Dieselöl (über 1N'atrium destilliert), 27,6 g Aluminiumtriäthyl und 8,5g Tita,nsäuretetrabutylester werden unter Stickstoff miteinander gemischt. Es entsteht eine klare, tiefrote Lösung, die für Polytnerisationen verwendet werden kann.Example 1 250 ccm Fischer-Tropsch diesel oil (distilled over 1N sodium), 27.6 g of aluminum triethyl and 8.5 g of tetrabutyl titanium are dissolved under nitrogen mixed together. The result is a clear, deep red solution that is used for polytnerizations can be used.
Beispiel 2 17 g Titansäuretetrabutylester werden mit 27 g Aluminiumtrihexyl in 250 ccm Dieselöl vermischt. Es entsteht ein Polymerisationska,talysator. Beispiel 3 9,6 g Zirkontetrabutylester, gelöst in 100 ccm Fischer-Tropsch-Dieselöl, werden in eine Lösung von 49,5 g Aluminiumtriisobutyl in 200 ccm Dieselöl eingerührt. Die Mischung färbt sich langsam über Gelb nach Braunschwarz. Sie kann für Polymerisationen verwendet werden.Example 2 17 g of tetrabutyl titanate are mixed with 27 g of aluminum trihexyl mixed in 250 cc diesel oil. A polymerization catalyst is created. example 3 9.6 g of zirconium tetrabutyl ester dissolved in 100 cc of Fischer-Tropsch diesel oil stirred into a solution of 49.5 g of aluminum triisobutyl in 200 cc of diesel oil. the Mixture slowly turns yellow to brown-black. They can be used for polymerizations be used.
Beispiel 4 6,7 g Zirkontetraisopropylat, gelöst in 100 ccm Fischer-Tropsch-Dieselöl, werden in eine Lösung von 25.5 g Alumin.iumtriäthyl in 150 ccm Dieselöl ein,-gerührt. Die Mischung färbt sich langsam über Gelb nach Braunrot. Sie wirkt polymerisierend auf Olefine. Beispiel 5 10g Titantetraäthylat, gelöst in, 100 ccm Fischer-Tropsch-Dieselöl, werden in eine Lösung von 25g Aluminiumtriäthyl in 150 ccm Dieselöl eingerührt. Die erhaltene schwarze Mischung wirkt polymerisierend auf Olefine.EXAMPLE 4 6.7 g of zirconium tetraisopropoxide dissolved in 100 cc of Fischer-Tropsch diesel oil are stirred into a solution of 25.5 g of aluminum triethyl in 150 cc of diesel oil. The mixture slowly turns from yellow to brownish-red. It has a polymerizing effect on olefins. Example 5 10 g of titanium tetraethylate, dissolved in 100 cc of Fischer-Tropsch diesel oil, are stirred into a solution of 25 g of aluminum triethyl in 150 cc of diesel oil. The black mixture obtained has a polymerizing effect on olefins.
Beispiel 6 18g Titantetrahexylat, gelöst in 100 ccm Fischer-Tropsch-Dieselöl, werden in einer Lösung von 62g Aluminiumtrioctyl in 150 ccm Dieselöl eingerührt. Die schwarze Mischung ist ein aktiver Polymerisationskatalvsator.Example 6 18 g of titanium tetrahexylate, dissolved in 100 cc of Fischer-Tropsch diesel oil, are stirred into a solution of 62 g of aluminum trioctyl in 150 cc of diesel oil. The black mixture is an active polymerization catalyst.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEZ5928A DE1039055B (en) | 1954-08-07 | 1954-08-07 | Polymerization catalysts and processes for their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEZ5928A DE1039055B (en) | 1954-08-07 | 1954-08-07 | Polymerization catalysts and processes for their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1039055B true DE1039055B (en) | 1958-09-18 |
Family
ID=7619598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEZ5928A Pending DE1039055B (en) | 1954-08-07 | 1954-08-07 | Polymerization catalysts and processes for their preparation |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1039055B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1113311B (en) * | 1959-06-19 | 1961-08-31 | Polymer Corp | Process for the polymerization of butadiene |
| DE1189985B (en) | 1962-06-21 | 1965-04-01 | Schering Ag | Process for the dimerization of terminal olefins with 5 to 7 carbon atoms |
| DE1468620B1 (en) * | 1962-03-22 | 1970-10-22 | Sunray Dx Oil Co | Process for the preparation of an aluminum and boron-containing catalyst suitable for the polymerization of olefins |
-
1954
- 1954-08-07 DE DEZ5928A patent/DE1039055B/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1113311B (en) * | 1959-06-19 | 1961-08-31 | Polymer Corp | Process for the polymerization of butadiene |
| DE1134202B (en) * | 1959-06-19 | 1962-08-02 | Polymer Corp | Process for the production of butadiene polymers with a cis-1,4 structure |
| DE1468620B1 (en) * | 1962-03-22 | 1970-10-22 | Sunray Dx Oil Co | Process for the preparation of an aluminum and boron-containing catalyst suitable for the polymerization of olefins |
| DE1189985B (en) | 1962-06-21 | 1965-04-01 | Schering Ag | Process for the dimerization of terminal olefins with 5 to 7 carbon atoms |
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