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US 8,759,280 B2Granted
Method for producing trimethylcyclododecatriene
AssigneeEvonik Degussa GmbH
InventorsDirk Kuppert, Juergen Herwig, Norbert Wilczok, Anita Voelkel, Manfred Thiery
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Abstract
The present invention relates to the preparation of trimethylcyclododecatriene in a continuous or batchwise process by trimerizing isoprene in the presence of a catalyst system and of a solvent. It is possible to isolate the resulting crude trimethylcyclododecatriene by means of distillation. The dimethylcyclooctadiene formed as a by-product may likewise be isolated from the crude product.
Claims20
A process for preparing trimethylcyclododecatriene, comprising:
- first charging a solvent comprising 15-1000 ppm of a polar component to a reactor;
- charging a catalyst system and at least one organometallic compound to the reactor charged with a solvent comprising 15-1000 ppm of a polar compound;
- heating the charged reactor to a reaction temperature;
- admitting isoprene to the heated charged reactor;
- and
- reacting the isoprene in the presence of the solvent, catalyst system and at least one organometallic compound to obtain a product mixture comprising
- trimethylcyclododecatriene,
- wherein
- a yield of the trimethylcyclododecatriene is greater than 65% of a theoretical yield calculated on a mass of isoprene admitted to the reactor,
- the product mixture comprises linear C15 oligomers and a ratio of trimethylcyclododecatriene to the linear C15 oligomers is greater than or equal to 10:1,
- the catalyst system comprises nickel, titanium or a mixture thereof,
- a compound containing at least one element of main group 5 of the Periodic Table of the Elements is added to the catalyst system,
- the polar component is represented by formula (I)
- HO—R (I)
- wherein
- R is selected from the group consisting of branched and
- unbranched C1-C18-alkyl, C1-C18-cycloalkyl, C1-C18-aryl, C1-C18-aralkyl and H, and
- the reaction temperature, in the case of a nickel-containing catalyst system, is less than or equal to 140° C. and, in the case of a titanium-containing catalyst system, is less than or equal to 80° C.
15 more elements
Dependencies are inferred from the claim text.