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Method for internal olefin hydroformylation reaction by using phosphine oxide polymer supported catalyst

A supported catalyst and olefin hydroformyl technology, which is applied in the direction of organic compound/hydride/coordination complex catalyst, catalytic reaction, carbon monoxide reaction preparation, etc., can solve the problems of low activity and poor conversion of internal olefins, and achieve High catalytic activity, stable air and moisture, and reduced production costs

Active Publication Date: 2022-06-07
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Internal olefins are relatively cheap olefins in industry, and are relatively easy to obtain in industry. For example, the product olefins produced by alkane dehydrogenation process are mainly internal olefins, but the hydroformylation of internal olefins has always been a hot topic in the field of hydroformylation research. Difficulties, mainly due to the low activity of internal olefins, which are not easy to convert
At present, there are no heterogeneous catalysts and processes specifically for the hydroformylation of internal olefins in the industry.

Method used

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  • Method for internal olefin hydroformylation reaction by using phosphine oxide polymer supported catalyst
  • Method for internal olefin hydroformylation reaction by using phosphine oxide polymer supported catalyst
  • Method for internal olefin hydroformylation reaction by using phosphine oxide polymer supported catalyst

Examples

Experimental program
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Effect test

Embodiment 1

[0045] The specific preparation steps of monomer B: 5°C, under the protection of Ar gas, 12.8g of 1-bromo-2-methyl-4-vinylbenzene (CAS No.: 90560-53-5) was dissolved in 50ml of tetrahydrofuran, stirred evenly and waited for use. 2.0g of Mg chips were put into the flask, the temperature of the flask was raised to 65°C, and 5 ml of the mixed solution of 1-bromo-2-methyl-4-vinylbenzene and tetrahydrofuran was added dropwise. into dark green, vigorously boiling) continue to add the remaining mixed solution dropwise, maintaining the dropwise temperature at 60°C. After the dropwise addition, the solution was incubated for 1 hour to obtain the Grignard reagent solution. After cooling to 0 degrees Celsius, a mixed solution of 4.5 g of diethyl phosphite and 50 ml of 2-methyltetrahydrofuran was added, and the reaction was continued for 1 h after the dropwise addition was completed. Add 10 ml of saturated ammonium chloride solution to annihilate the reaction, the mixture is divided int...

Embodiment 2

[0049] In Example 2, except that 50.0 g of the second component, divinylbenzene, was not added, the rest of the synthesis process and conditions were the same as those in Example 1.

Embodiment 3

[0051] In Example 3, except that 50.0 g of the second component tristyrylbenzene (ligand L3 in claim 3) was used instead of divinylbenzene (ligand L1), the rest of the synthesis process and conditions were the same as those in Example 1 same.

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Abstract

The invention discloses a method for carrying out internal olefin hydroformylation reaction by using a phosphine oxide polymer supported catalyst, and the catalyst takes one, two or more than two of metals Rh, Co, Ir, Ru, Pt, Pd and Fe as active components, and takes a phosphine oxide polymer as a carrier. The heterogeneous catalyst provided by the invention has good performance in internal olefin hydroformylation reaction, a hydroxyl functional group connected to P can be formed after the secondary phosphine oxide monomer in the catalyst body is coordinated with metal, the acidity of the hydroxyl functional group is beneficial to internal olefin isomerization, the ratio of normal aldehyde to isomerous aldehyde in a hydroformylated product is flexible and adjustable, and the catalyst has good catalytic activity. And the alkane content in the product is lower than 1%. The phosphine oxide polymer supported catalyst provided by the invention is simple and efficient to separate from reactants and products, the production cost of high-carbon aldehyde is greatly reduced, and a new industrial technology is provided for internal olefin hydroformylation reaction.

Description

technical field [0001] The invention belongs to the field of heterogeneous catalysis and fine chemical industry, and particularly relates to a method for performing hydroformylation reaction of internal olefins by utilizing a phosphine oxide polymer-supported catalyst. Background technique [0002] The product aldehydes of the hydroformylation of olefins are very useful intermediates, and the subsequent conversion products such as alcohols, acids, esters and amines have a wide range of applications. At present, the hydroformylation of olefins in industry is mainly carried out under homogeneous conditions. The catalysts used are mainly homogeneous complex catalysts of Rh and Co metals that are miscible with the reaction system. Faced with the loss of metals and ligands, the operation complex issues. Today, with the concept of green chemistry getting more and more attention, it is urgent to develop green and environmentally friendly heterogeneous processes and catalysts. [...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/50C07C47/02C07C47/14C07C47/27C07C47/19C07C47/12C07C47/198C07C67/347C07C69/67C07C253/30C07C255/17C07C51/373C07C59/147B01J31/24B01J35/10
CPCC07C45/50C07C67/347C07C253/30C07C51/373B01J31/2404B01J2231/321B01J2531/822B01J2531/845B01J2531/827B01J35/394B01J35/613B01J35/615B01J35/617B01J35/633B01J35/643B01J35/647B01J35/695C07C47/02C07C47/14C07C47/27C07C47/19C07C47/12C07C47/198C07C69/67C07C255/17C07C59/147Y02P20/584
Inventor 李存耀严丽丁云杰丁玉龙姜淼马雷姬广军钱磊磊
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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