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Catalyst for catalyzing butadiene cyclization trimerization and application method thereof

A catalyst, butadiene technology, applied in the direction of organic compound/hydride/coordination complex catalyst, physical/chemical process catalyst, chemical instrument and method, etc., can solve the problem of low yield and low butadiene conversion rate , low selectivity, etc.

Inactive Publication Date: 2012-09-26
WUDI SINORANCE CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is the butadiene ring catalyzed by a very small amount of ZrCl4 and Ziegler-Natta catalyst in the prior art The selectivity of trans, trans, cis-1,5,9-cyclododecatriene is still low in the trimerization reaction, trans, trans, cis-1,5,9-cyclododecatriene The yield of high-value products is very low, and the conversion rate of butadiene is not high; thereby providing a kind of trans, trans, cis-1,5,9-cyclododecatriene with high selectivity, and can improve Catalyst for catalytic butadiene cyclotrimerization reaction of butadiene conversion and its use method

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Toluene, zirconium naphthenate, titanium naphthenate and AlEt 3 After dehydration treatment, the water content is less than 10ppm. Butadiene was purified with base and 5A molecular sieves, AlEt 3 For industrial products.

[0023] 691g of toluene, 0.0388g of zirconium naphthenate, 9.133g of AlEt 3 , 32.454kg of butadiene and 3.662g of titanium naphthenate were sequentially added into the reactor, mixed and reacted at 30°C for 40 hours. The pH value of the reaction product is adjusted to be weakly acidic, and after the reaction product is settled to remove impurities, the butadiene trimer is obtained after being fractionated and refined by a fractionating tower.

[0024] The conversion rate of butadiene is 90%, and the obtained butadiene trimer is measured with a gas chromatographic analyzer to measure anti, trans, cis-1,5,9-cyclododecatriene content 97%.

Embodiment 2

[0026] Toluene, zirconium naphthenate, titanium naphthenate, and AlEtCl 2 After dehydration treatment, the water content is less than 10ppm. Butadiene was purified with base and 5A molecular sieves, AlEtCl 2 For industrial products.

[0027] 921g toluene, 0.1163g zirconium naphthenate, 21.12gAlEt 3 , 37.863kg of butadiene and 10.988g of titanium naphthenate were sequentially added into the reactor, mixed and reacted at 90°C for 20 hours. The pH value of the reaction product is adjusted to be weakly acidic, and after the reaction product is settled to remove impurities, the butadiene trimer is obtained after being fractionated and refined by a fractionating tower.

[0028] The conversion rate of butadiene is 92%, and the obtained butadiene trimer is measured with a gas chromatographic analyzer, and the trans, trans, cis-1,5,9-cyclododecatriene content is measured therein 97.2%.

Embodiment 3

[0030] Toluene, zirconium naphthenate, titanium naphthenate and AlEt 1.46 Cl 1.54 After dehydration treatment, the water content is less than 10ppm. Butadiene was purified with base and 5A molecular sieves, AlEt 1.46 Cl 1.54 For industrial products.

[0031] 750g toluene, 0.093g zirconium naphthenate, 15.14gAlEtCl 2 , 36.78kg of butadiene and 7.643g of titanium naphthenate were sequentially added into the reactor, mixed and reacted at 40°C for 30 hours. The pH value of the reaction product is adjusted to be weakly acidic, and after the reaction product is settled to remove impurities, the butadiene trimer is obtained after being fractionated and refined by a fractionating tower.

[0032] The conversion rate of butadiene is 91%, and the obtained butadiene trimer is measured with a gas chromatographic analyzer, and the trans, anti, cis-1,5,9-cyclododecatriene content is measured therein 97.5%.

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Abstract

The invention relates to a catalyst for catalyzing butadiene cyclization trimerization and an application method thereof. The components of the catalyst include titanium naphthenate and AlRyZ3-y, wherein Z is a halogeno group, R is an alkyl group, and Y is more than 0 and less than or equal to 3; and the catalyst also includes a small amount of zirconium naphthenate. When the catalyst is used for catalyzing the butadiene cyclization trimerization, methylbenzene, the zirconium naphthenate, the AlRyZ3-y, the butadiene and the titanium naphthenate are added into a reaction kettle in sequence and then mixed; the mixture is reacted for 20-40 hours at the temperature of 30-90 DEG C to obtain a reaction product; and sedimentation, distillation and purification treatments are carried out on the reaction product to obtain a butadiene trimer. Through measuring, the conversion of the butadiene is 90-95%, and the content of trans, trans, cis-1,5,9-cyclododecatriene in the trimer is 99.99-100%.

Description

technical field [0001] The invention relates to a catalyst for catalyzing the cyclotrimerization reaction of butadiene and a use method thereof, belonging to the field of catalysts. Background technique [0002] Anti, anti, cis-1,5,9-cyclododecatriene is a macrocyclic intermediate with multiple uses, and it can be used to synthesize some valuable macrocyclic organic compounds and prepare musk, perfume, paint , adhesives, nylon and flame retardants and other chemical products, therefore, trans, trans, cis-1,5,9-cyclododecatriene is an indispensable raw material for the manufacture of industrial and daily products. The industrial preparation of trans, trans, cis-1,5,9-cyclododecatriene is generally made of butadiene as raw material, and Ziegler-Natta catalyst is used to catalyze the cyclotrimerization of butadiene. The cyclotrimerization products of butadiene are three different configurations of cyclododecatriene, and the Ziegler-Natta catalyst is effective for trans, trans,...

Claims

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Application Information

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IPC IPC(8): B01J31/14C07C13/277C07C2/46
Inventor 秦如新
Owner WUDI SINORANCE CHEM
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