DE1078108B - Process for the trimerization of 2,3-dimethylbutadiene- (1,3) to an open-chain trimer - Google Patents
Process for the trimerization of 2,3-dimethylbutadiene- (1,3) to an open-chain trimerInfo
- Publication number
- DE1078108B DE1078108B DEST14119A DEST014119A DE1078108B DE 1078108 B DE1078108 B DE 1078108B DE ST14119 A DEST14119 A DE ST14119A DE ST014119 A DEST014119 A DE ST014119A DE 1078108 B DE1078108 B DE 1078108B
- Authority
- DE
- Germany
- Prior art keywords
- dimethylbutadiene
- trimerization
- open
- aluminum
- halides
- 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
- 239000013638 trimer Substances 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 7
- 238000005829 trimerization reaction Methods 0.000 title claims description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- -1 alkyl aluminum halides Chemical class 0.000 claims description 3
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000011651 chromium Substances 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 150000001845 chromium compounds Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 9
- CJSBUWDGPXGFGA-UHFFFAOYSA-N dimethyl-butadiene Natural products CC(C)=CC=C CJSBUWDGPXGFGA-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- AHXGRMIPHCAXFP-UHFFFAOYSA-L chromyl dichloride Chemical compound Cl[Cr](Cl)(=O)=O AHXGRMIPHCAXFP-UHFFFAOYSA-L 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- HZRYQRDWNVPWOO-UHFFFAOYSA-N 2,3,3,5,6,8,8,9-octamethyldeca-1,4,6,9-tetraene Chemical compound CC(=C)C(C=C(C(=CC(C(=C)C)(C)C)C)C)(C)C HZRYQRDWNVPWOO-UHFFFAOYSA-N 0.000 description 1
- RNHOSNRUSRHGRV-UHFFFAOYSA-N CC(=C)C(=CC=C(C(=CCC(C(C)C)C)C)C)C Chemical compound CC(=C)C(=CC=C(C(=CCC(C(C)C)C)C)C)C RNHOSNRUSRHGRV-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical class CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/38—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of dienes or alkynes
- C07C2/40—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of dienes or alkynes of conjugated dienes
- C07C2/403—Catalytic processes
- C07C2/406—Catalytic processes with hydrides or organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/132—Compounds comprising a halogen and chromium, molybdenum, tungsten or polonium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/135—Compounds comprising a halogen and titanum, zirconium, hafnium, germanium, tin or lead
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- C07C2531/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24
- C07C2531/34—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24 of chromium, molybdenum or tungsten
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24
- C07C2531/38—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24 of titanium, zirconium or hafnium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Trimerisation von 2,3-Dimethylbutadien- ,3) zu einem offenkettigen Trimeren In den belgischen Patentschriften 555 180 und 564 175 werden Verfahren geschildert, nach denen Diolefine, wie Butadien, Isopren und Piperylen mit Hilfe von metallorganischen Mischkatalysatoren in ringförmige Kohlenwasserstoffe mit mindestens 8 Kohlenstoffatomen, d. h. in Cyclododecatriene-(1,5,9) verwandelt werden können. Die ringförmigen Verbindungen dienen als wichtige Ausgangsprodukte zur Gewinnung bifunktioneller Derivate des n-Dodecans, z B. Dodecan-1,12-disäure und des 12-Aminododecansäurelactams. Process for the trimerization of 2,3-dimethylbutadiene, 3) to one open-chain trimers In the Belgian patents 555 180 and 564 175 are Process described by which diolefins such as butadiene, isoprene and piperylene with the help of organometallic mixed catalysts into ring-shaped hydrocarbons with at least 8 carbon atoms, d. H. converted into cyclododecatriene- (1,5,9) can be. The ring-shaped connections serve as important starting products to obtain bifunctional derivatives of n-dodecane, e.g. dodecane-1,12-diacid and 12-aminododecanoic acid lactam.
Es wurde im weiteren Verlauf der Untersuchungen die überraschende Beobachtung gemacht, daß das 2,3-Dimethylbutadtien-(1,3) bei einer analogen B handlung mit den metallorganisehen Mischkatalysatoren kein ringförmiges Trimerisat liefert, daß vielmehr ein offenkettiges Trimerer in hohen Ausbeuten gebildet wird. It became the most surprising in the further course of the investigations Observation made that the 2,3-dimethylbutadtiene- (1,3) acted in an analogous manner with the organometallic mixed catalysts does not produce a ring-shaped trimer, that rather an open-chain trimer is formed in high yields.
Das Trimere entspricht der Summenformel Cls H30 und hat den Siedepunkt 1300 C bei 5 mm und den Brechungsindex »2Do = 1,4973. Bei der katalytischen Hydrierung unter Druck wird die Vierdoppelbindungen äquivalente Menge Wasserstoff aufgenommen, was die offenkettige Struktur beweist Die offenkettige Konstitution wird auch durch das IR-Spektrum bestätigt. Im Spektrum tritt bei 890 cm-' eine starke Bande auf, die der endständig verzweigten Doppelbindung zuzuordnen ist. The trimer corresponds to the molecular formula Cls H30 and has the boiling point 1300 C at 5 mm and the refractive index »2Do = 1.4973. In catalytic hydrogenation under pressure the four double bonds equivalent amount of hydrogen is absorbed, what the open-chain structure proves The open-chain constitution is also through the IR spectrum is confirmed. A strong band appears in the spectrum at 890 cm- ', which is to be assigned to the terminally branched double bond.
Es handelt sich bei dieser Trimerisation offenbar um einen völlig neuen Typ der Reaktionen von konugierten Diolefinen mit metallorganischen Mischkatalysatoren, denn es läßt sich zeigen, daß das trimere Dimethylbutadien nicht durch die übliche 1,2- bzw. 1,4-Addition von 3 Molekülen des Monomeren entstehen kann, da das Reaktionsprodukt neben zwei endständig verzweigten Doppelbindungen zwei mittelständige, und zwar konjugilerte Doppelbindungen aufweist. This trimerization is evidently a complete one new type of reactions of conjugated diolefins with organometallic mixed catalysts, because it can be shown that the trimeric dimethylbutadiene is not by the usual 1,2- or 1,4-addition of 3 molecules of the monomer can occur as the reaction product in addition to two terminally branched double bonds, two central ones, namely has conjugated double bonds.
Das Paar konjugierter Doppelbindungen läßt sich einmal im IR-Spektrum nachweisen, zum anderen gelingt es ohne Schwierigkeit, ein Molekül Maleinsäureanhydrid nach Diels-Alder zu addieren. Das Additionsprodukt entspricht der Summenformel C22 H32 03. The pair of conjugated double bonds can be seen once in the IR spectrum On the other hand, it is possible to detect a molecule of maleic anhydride without difficulty according to Diels-Alder to be added. The addition product corresponds to the empirical formula C22 H32 03.
Dem trimeren Dimethylbutadien kann folgende Konstitutionsformel zugrunde
liegen:
Man arbeitet mit Vorteil in einem indifferenten Lösungsmittel, wie einem aliphatischen bzw. aromatischen bzw. halogenierten Kohlenwasserstoff, bevorzugt aber in Benzol. It is advantageous to work in an inert solvent, such as an aliphatic or aromatic or halogenated hydrocarbon, preferably but in benzene.
Als Reaktionstemperatur kommen Temperaturen von 0 bis 1000 C in Frage, bevorzugt zwischen 20 und 500 C. Temperatures from 0 to 1000 C come into consideration as the reaction temperature, preferably between 20 and 500 C.
Die Ausbeuten an Trimeren betragen 70 bis 90§/o. The yields of trimers are 70 to 90%.
Das trimere Dimethylbutadien dient als wertvolles Ausgangsprodukt für organische Synthesen, besonders aber zur Darstellung stark methylverzweigter a,co-bifunktioneller Verbindungen, die für die Gewinnung von Kunststoffen, wie Polyester und Polyamide, Bedeutung besitzen. The trimeric dimethylbutadiene serves as a valuable starting product for organic syntheses, but especially for the preparation of highly methyl-branched ones a, co-bifunctional compounds used in the production of plastics such as polyester and polyamides, are important.
Beispiel In 1 1 abs. Benzol werden 4,8 cm3 (0,059 Mol) Chromylchlorid gelöst. Unter Rühren tropft man zu dieser Lösung langsam 33 cm3 (0,24 Mol) Aluminiumtriäthyl, wobei sich die Mischung erwärmt und ein Niederschlag ausfällt. Man rührt t/2 Stunde weiter, erwärmt auf 500 C und tropft dann 323 g Dimethylbutadien im Verlaufe einer Stunde ein. Die Mischung wird 24 Stunden bei 500 C kräftig gerührt. Danach zersetzt man den Ansatz mit der dem Aluminium äquivalenten Menge Methanol und verdünnter Schwefelsäure. Die organische Schicht wird mit Wasser gewaschen, mit Ca C12 getrocknet. Bei der Destillation erhält man 220g des Trimeren, das bei Kp.5 = 1300 C übergeht, n2,0 = 1,4973. Ausbeute 820/o, bezogen auf umgesetztes Dimethylbutadien. Der Destillationsrückstand besteht zum größten Teil aus einem Tetrameren des Dimethylbutadiens. Example In 1 1 abs. Benzene becomes 4.8 cc (0.059 mol) of chromyl chloride solved. 33 cm3 (0.24 mol) of aluminum triethyl are slowly added dropwise to this solution while stirring, the mixture heats up and a precipitate separates out. The mixture is stirred for t / 2 hour further, heated to 500 ° C. and then 323 g of dimethylbutadiene are added dropwise in the course of a Hour one. The mixture is stirred vigorously at 500 ° C. for 24 hours. After that it decomposes one the approach with the aluminum equivalent amount of methanol and diluted Sulfuric acid. The organic layer is washed with water, dried with Ca C12. In the Distillation gives 220g of the trimer, which passes over at bp 5 = 1300 C, n2.0 = 1.4973. Yield 820 / o, based on converted dimethylbutadiene. The still residue consists for the most part of a tetramer of dimethylbutadiene.
Claims (4)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT1078108X | 1957-09-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1078108B true DE1078108B (en) | 1960-03-24 |
Family
ID=3685062
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEST14119A Pending DE1078108B (en) | 1957-09-02 | 1958-08-12 | Process for the trimerization of 2,3-dimethylbutadiene- (1,3) to an open-chain trimer |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1078108B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1212064B (en) * | 1961-06-07 | 1966-03-10 | Basf Ag | Process for the catalytic production of liquid, predominantly open-chain oligomers from 1,3-dienes |
| DE1216286B (en) * | 1961-09-01 | 1966-05-12 | Basf Ag | Process for the catalytic production of liquid, predominantly open-chain oligomers from 1,3-dienes |
| US4668838A (en) * | 1986-03-14 | 1987-05-26 | Union Carbide Corporation | Process for trimerization |
| US4853356A (en) * | 1986-03-14 | 1989-08-01 | Union Carbide Corporation | Process for trimerization |
-
1958
- 1958-08-12 DE DEST14119A patent/DE1078108B/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1212064B (en) * | 1961-06-07 | 1966-03-10 | Basf Ag | Process for the catalytic production of liquid, predominantly open-chain oligomers from 1,3-dienes |
| DE1216286B (en) * | 1961-09-01 | 1966-05-12 | Basf Ag | Process for the catalytic production of liquid, predominantly open-chain oligomers from 1,3-dienes |
| US4668838A (en) * | 1986-03-14 | 1987-05-26 | Union Carbide Corporation | Process for trimerization |
| US4853356A (en) * | 1986-03-14 | 1989-08-01 | Union Carbide Corporation | Process for trimerization |
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