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Catalyst and application of catalyst in catalyzing butadiene cyclization trimerization

A cyclization trimerization reaction, catalyst technology, applied in physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, organic chemistry and other directions, 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

[0006] The technical problem to be solved by the present invention is that although a very small amount of ZrCl in the prior art 4 with TiCl 4 / AlEt 1.46 Cl 1.54 Synergistically catalyzed butadiene cyclotrimerization has increased selectivity to trans, trans, cis-1,5,9-cyclododecatriene, but butadiene cyclotrimerization to trans, trans , the selectivity of cis-1,5,9-cyclododecatriene is still low, so that the yield of trans, trans, cis-1,5,9-cyclododecatriene, a high-value product Very low, the conversion rate of butadiene is not high; And then provide a kind of trans, trans, cis-1,5,9-cyclodecatriene has very high selectivity, and can improve the conversion rate of butadiene Catalyst and Its Application in Catalytic Cyclotrimerization of Butadiene

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Toluene, CP 2 ZrCl 2 、TiBr 4 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.

[0024] 691g toluene, 0.0146gCP 2 ZrCl 2 , 9.133gAlEt 3 , 32.454kg butadiene and 1.837gTiBr 4 Add them to the reaction kettle one by one, mix and react 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.

[0025] 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 96%.

Embodiment 2

[0027] Toluene, CP 2 ZrCl 2 、TiBr 4 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.

[0028] 921g toluene, 0.0438gCP 2 ZrCl 2 , 21.12gAlEt 3 , 37.863kg butadiene and 5.512gTiBr 4 Add them to the reaction kettle one by one, mix and react 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.

[0029] 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 95%.

Embodiment 3

[0031] Toluene, CP 2 ZrCl 2 、TiBr 4 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.

[0032] 750g toluene, 0.035gCP 2 ZrCl 2 , 15.14gAlEtCl 2 , 36.78kg butadiene and 3.834gTiBr 4 Add them to the reaction kettle one by one, mix and react 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.

[0033] 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 96.5%.

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Abstract

The invention relates to a catalyst and application of the catalyst in catalyzing butadiene cyclization trimerization. The components of the catalyst include TiX4 and AlRyZ3-y, wherein X and Z are halogeno groups; R is alkyl; Y is more than 0 and less than or equal to 3; the catalyst is characterized by also includin CP2ZrC12. When the catalyst is used for catalyzing the butadiene cyclization trimerization, toluene, CP2ZrC12, AlRyZ3-y, butadiene and TiX4 are added to a reaction kettle in sequence and then mixed; the mixture reacts for 20-40 hours at 30-90 DEG C to obtain a reaction product; and sedimentatin, distillation and purification treatments are carried out on the reaction product to obtain a butadiene trimer. Through measuring, the conversion rate 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 and its application in catalyzing the cyclotrimerization reaction of butadiene, belonging to the field of catalysts. Background technique [0002] Butadiene cyclotrimerization products include three different configurations of cyclododecatriene (referred to as butadiene trimer), among which trans, trans, cis-1,5,9-cyclododecatriene It is a special-purpose macrocyclic intermediate, which can be used to synthesize some macrocyclic organic compounds and prepare chemical products such as musk, perfume, paint, adhesive, nylon and flame retardant. Therefore, trans, trans, cis- 1,5,9-Cyclododecatriene is the one with the highest application value among the three different configuration products produced by the cyclotrimerization of butadiene. [0003] Industrially, the preparation of butadiene trimer is to use butadiene as raw material, and use Ziegler-Natta catalyst to catalyze, but because the catalyst is opposite to tra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/38C07C13/277C07C2/46
Inventor 秦如新
Owner WUDI SINORANCE CHEM
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