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Method for producing trimethylcyclododecatriene

A technology of trimethylcyclododecatriene and isoprene, which is applied in the field of preparing trimethylcyclododecatriene, and can solve the problems such as the decrease of CDT yield

Inactive Publication Date: 2013-11-20
EVONIK DEGUSSA GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, Ube Industries reported that the yield of CDT decreased when water was used to split the catalyst

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1 (comparative example)

[0044] 0.5 liter of benzene with a water content of 15 ppm was filled into a 1.5 liter glass autoclave with a nitrogen atmosphere. Then add 42.5 ml ethyl aluminum sesquichloride (20% solution in benzene) and 13.2 ml TiCl 4 (5% solution in benzene). The autoclave was closed and the reaction mixture was warmed to 40 °C. At this temperature, 343 g of isoprene were added within 4 hours. During the addition of isoprene, the temperature inside the autoclave was kept constant at 40°C. Stirring of the reaction mixture was continued at 40° C. for 1 hour after the end of the addition, and finally the catalyst was decomposed by adding 25% aqueous sodium hydroxide solution. The organic reaction mixture contained 48.81% TMCDT, and 3.48% cyclic and linear C 10 Dimer and 4.85% linear trimer and 29.4% polymer component.

Embodiment 2

[0045] Embodiment 2 (according to the present invention)

[0046] 0.5 liter of benzene with a water content of 15 ppm was filled into a 1.5 liter glass autoclave with a nitrogen atmosphere. Then add 84.9 ml ethyl aluminum sesquichloride (20% solution in benzene) and 13.2 ml TiCl 4 (5% solution in benzene). The autoclave was closed and 201 mg of ammonia gas was added through a septum with stirring at room temperature. The reaction mixture was warmed to 40 °C. At this temperature, 170.5 g of isoprene were added within 4 hours. During the addition of isoprene, the temperature inside the autoclave was kept constant at 40°C. Stirring of the reaction mixture was continued at 40° C. for 1 hour after the end of the addition, and finally the catalyst was decomposed by adding 25% aqueous sodium hydroxide solution. The organic reaction mixture contained 60.27% TMCDT, and 14.07% cyclic and linear C 10 Dimer and 4.14% linear trimer and 13.35% polymer component.

Embodiment 3

[0047] Embodiment 3 (according to the present invention)

[0048] 4 liters of benzene having a water content of 15 ppm was filled into a 10 liter stainless steel autoclave with a nitrogen atmosphere. Then add 76.8 ml ethyl aluminum sesquichloride (20% solution in benzene) and 16.3 ml TiCl 4 (5% solution in benzene). The autoclave was closed and 296 mg of ammonia gas was added through a septum with stirring at room temperature. The reaction mixture was warmed to 40 °C. At this temperature, 2716 g of isoprene was added at a flow rate of 7 g / min. During the addition of isoprene, the temperature inside the autoclave was kept constant at 40°C. Stirring of the reaction mixture was continued at 40° C. for 2 hours after the end of the addition, and finally the catalyst was decomposed by adding 25% aqueous sodium hydroxide solution. The organic reaction mixture contained 53.12% TMCDT, and 9.85% cyclic and linear C 10 Dimers and 2.29% linear trimers.

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PUM

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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.

Description

[0001] This application is a divisional application of the invention patent application with the application number 200580046315.9 (PCT / EP2005 / 054541) and the application date of September 13, 2005. technical field [0002] The present invention relates to the preparation of cyclic isoprene trimers (i.e. 1,5,9- and 1,6,9-trimethylcyclododecatriene) using catalyst systems containing nickel and / or titanium - Continuous and discontinuous processes for (1,5,9) (TMCDT). Furthermore, the invention also includes the above-mentioned processes in which 1,5- and / or 1,6-dimethyl Cyclooctadiene (DMCOD), in which case it is preferred to use a nickel-containing catalyst system. In addition, the invention also includes a mixture of substances with a specific ratio of TMCDT to linear C15 oligomers. Said mixture of substances is based on the present invention obtained by the invented method. Background technique [0003] Numerous patents and literature are devoted to processes or experiment...

Claims

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Application Information

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IPC IPC(8): C07C13/277C07C2/46
CPCC07C2101/18C07C2523/755C07C2/465C07C2101/20C07C2521/06C07C2601/18C07C2601/20C07C13/263C07C13/277
Inventor D.库帕特J.赫维格N.威尔查克A.沃克尔M.蒂里
Owner EVONIK DEGUSSA GMBH