Catalyst composition for reducing normal-to-isomer ratio of hydroformylation products of olefin

A catalyst and composition technology, applied in the direction of organic compound/hydride/coordination complex catalyst, physical/chemical process catalyst, catalytic reaction, etc., can solve the lack of catalyst stability and reaction activity, shortening catalyst life, key influence Factors are not clear and other problems, to achieve the effect of improving catalytic conversion rate and conversion rate, strong catalytic activity and stability, and strong π electron accepting ability

Active Publication Date: 2019-09-20
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are corresponding problems in this catalyst system: for example, in order to reduce the positive-to-isotropic ratio of butyraldehyde, the adjustable means include adjusting the partial pressure of carbon monoxide, adjusting the partial pressure of olefins, adjusting the reaction temperature, etc., and the most effective way is to adjust the partial pressure of carbon monoxide. However, it will cause the problem of reduced reaction stability, reduced propylene conversion rate, and shortened catalyst life.
However, CO is a catalyst poison. Excessive CO partial pressure will cause rhodium atoms to bridge and reunite, reducing the catalytic activity and life of rhodium.
[0012] Obviously, the prior art has paid attention to the influence of reaction parameters and catalyst ligands on the positive-to-isotropic ratio of the product. However, due to the demand for high positive-to-isotropic ratio of the traditional butanol plant, the existing research mainly focuses on how to effectively improve the product positive-to-isotropic ratio. For There are few studies on reducing the positive-to-isotropic ratio, resulting in unclear key influencing factors, and lack of research on catalyst stability and reactivity under low positive-to-isotropic ratio conditions
[0013] In view of the lack of a catalytic system for reducing the normal isomerization ratio of olefin hydroformylation reaction products in the prior art, it is necessary to develop such a catalytic system

Method used

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  • Catalyst composition for reducing normal-to-isomer ratio of hydroformylation products of olefin
  • Catalyst composition for reducing normal-to-isomer ratio of hydroformylation products of olefin
  • Catalyst composition for reducing normal-to-isomer ratio of hydroformylation products of olefin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] With nitrogen, the catalyst preparation tank is replaced to an oxygen content lower than 0.1%, and in the preparation tank, 592.5 g of mixed butyraldehyde (normal isotropic ratio 5: 1) is added successively, rhodium Parker 0.63 g, co-catalyst triphenylphosphine 112.5 g, co-catalyst Add 37.5g of agent A (A1), 7.5g of auxiliary agent B, heat to 50°C, and stir for 120min.

[0054] Test rhodium content 168ppm, co-catalyst 15%, co-agent A (A1) 5%, co-agent B 1%.

[0055] Utilize propylene hydroformylation reaction to evaluate the catalytic system of the present embodiment:

[0056] The reaction was carried out in a tank reactor with a stirring paddle (the volume of the stirred tank was 0.5 L, and the stirring rate was 200 r / min), and 50 g of the prepared catalyst composition was added into the reactor in advance. Propylene (polymerization grade) and synthesis gas (the molar ratio of hydrogen to carbon monoxide is 1.05:1) are fed continuously from the bottom of the reactor i...

Embodiment 2

[0058] Use nitrogen to replace the catalyst preparation tank until the oxygen content is lower than 0.1%, add 652.5 g of mixed butyraldehyde (normal to isotropic ratio 5:1), 0.75 g of rhodium parka, 90 g of cocatalyst triphenylphosphine, and auxiliary agent A (A2) 3.75g, additive B 3.75g, heated to 50°C, and stirred for 120min.

[0059] Test rhodium content 200ppm, cocatalyst 12%, auxiliary agent A (A2) 0.5%, auxiliary agent B 0.5%.

[0060] Utilize propylene hydroformylation reaction to evaluate the catalytic system of the present embodiment:

[0061] The reaction was carried out in a tank reactor with a stirring paddle (the volume of the stirred tank was 0.5 L, and the stirring rate was 200 r / min), and 50 g of the prepared catalyst composition was added into the reactor in advance. Propylene (polymerization grade) and synthesis gas (the molar ratio of hydrogen to carbon monoxide is 1.05:1) are fed continuously from the bottom of the reactor in the gas phase, the reaction te...

Embodiment 3

[0063] Use nitrogen to replace the catalyst preparation tank until the oxygen content is lower than 0.1%, add 600 g of mixed butyraldehyde (normal to isotropic ratio 5:1), 0.91 g of rhodium parka, 75.12 g of cocatalyst triphenylphosphine, and additives in the preparation tank. A (A3) 60g, additive B 15g, heated to 50°C, stirred for 120min.

[0064] Test rhodium content 242ppm, co-catalyst 10%, co-agent A (A3) 8%, co-agent B 2%.

[0065] Utilize propylene hydroformylation reaction to evaluate the catalytic system of the present embodiment:

[0066] The reaction was carried out in a tank reactor with a stirring paddle (the volume of the stirred tank was 0.5 L, and the stirring rate was 200 r / min), and 50 g of the prepared catalyst composition was added into the reactor in advance. Propylene (polymerization grade) and synthesis gas (the molar ratio of hydrogen to carbon monoxide is 1.05:1) are fed continuously from the bottom of the reactor in the gas phase, the reaction tempera...

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Abstract

The invention discloses a catalyst composition for reducing the normal-to-isomer ratio of aldehyde products which are obtained through a hydroformylation reaction of olefin. The catalyst composition comprises a solvent, a catalyst active component, a cocatalyst, an assistant A and an assistant B, wherein the catalyst active component is a rhodium salt, the cocatalyst is triphenylphosphine, the assistant A is a phosphine-containing alkyl ligand, and the assistant B is indole structure-containing doped benzene. The catalyst composition is applied to hydroformylation of olefin, the normal-to-isomer ratio in the products can be reduced, and the selectivity and stability of a catalyst under the condition of a low normal-to-isomer ratio of less than 10 can be improved.

Description

technical field [0001] The invention belongs to the technical field of organic chemical industry, and in particular relates to a catalyst composition for reducing the normal isomerization ratio of olefin hydroformylation products. Background technique [0002] The hydroformylation reaction of propylene has important industrial significance, and its reaction products include n-butyraldehyde and isobutyraldehyde. The rhodium / triphenylphosphine complex catalyst system commonly used in industry has good stability and catalytic activity, and the products are n-butyraldehyde and isobutyraldehyde. Compared with design 7-10, it has a larger flexible adjustment space. [0003] N-butyraldehyde can be used for hydrogenation to produce butanol, which continues to be used as a downstream raw material; isobutyraldehyde, as a by-product of the reaction, has received less industrial attention. In recent years, with the vigorous development of the neopentyl glycol industry, isobutyraldehyde...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22B01J31/24B01J35/00C07C45/50C07C47/02
CPCB01J35/0006B01J31/2404B01J31/1815C07C45/50B01J2231/321B01J2531/822C07C47/02
Inventor 孔祥明徐艳飞梁健国欣张宏科华卫琦
Owner WANHUA CHEM GRP CO LTD
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