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Method for preparing aldehyde through olefin hydroformylation

A technology of olefin hydroformyl and hydroformyl, which is applied in chemical instruments and methods, carbon monoxide reaction preparation, organic compound/hydride/coordination complex catalysts, etc. It can solve the problems of low positive-to-negative ratio and poor catalyst stability, etc. , to achieve the effect of prolonging service life, high catalytic activity and reducing energy consumption of separation

Inactive Publication Date: 2016-05-11
SHANGHAI HUAYI GRP CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The technical problem to be solved by the present invention is the problem of low positive-to-isotropic ratio and poor catalyst stability in the prior art, and a new method for preparing aldehydes by hydroformylation of olefins is provided

Method used

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  • Method for preparing aldehyde through olefin hydroformylation
  • Method for preparing aldehyde through olefin hydroformylation
  • Method for preparing aldehyde through olefin hydroformylation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Add [Rh(acac)(CO) to a 200mL stainless steel autoclave equipped with a pressure gauge under air atmosphere 2 ] (0.07mmol, 18.1mg) and 0.28mmol of triphenylphosphine L1 monophosphine ligand and 0.14mmol of L12 bidentate phosphite ligand, and 70mL of anhydrous toluene, connect the gas line to synthesis gas (hydrogen: Carbon monoxide = 1:1) After replacing the gas in the kettle three times, stir with an electromagnetically driven mechanical stirrer, heat up to the inner temperature of the kettle at 100°C, and feed synthesis gas until the total pressure is 2.0MPa, at 100°C, 2.0MPa After reacting for 1 h, the rhodium / (bidentate phosphite-monophosphine ligand) complex catalyst HRh(L12)(L1)(CO) was obtained. Its molecular structure is as follows:

[0050] 31 PNMR (Toluene, 162MHz) P1 coordinated by L12 and rhodium: δ177.9ppm, P2 coordinated by L12 and rhodium: δ175.1ppm, P3 coordinated by L1 and rhodium: 36.2ppm, 1 J RhP1 = 249Hz, 1 J RhP2 = 249Hz, 1 J RhP3 = 141Hz, ...

Embodiment 2

[0052] Add [Rh(acac)(CO) to a 200mL stainless steel autoclave equipped with a pressure gauge under air atmosphere 2 ] (0.07mmol, 18.1mg) and 0.28mmol of triphenylphosphine L1 monophosphine ligand and 0.14mmol of L11 bidentate phosphite ligand, and 70mL of anhydrous toluene, connect the gas line to synthesis gas (hydrogen: Carbon monoxide = 1:1) After replacing the gas in the kettle three times, stir with an electromagnetically driven mechanical stirrer, heat up to the inner temperature of the kettle at 100°C, and feed synthesis gas until the total pressure is 2.0MPa, at 100°C, 2.0MPa After reacting for 1 h, the rhodium / (bidentate phosphite-monophosphine ligand) complex catalyst HRh(L11)(L1)(CO) was obtained. Its molecular structure is as follows:

[0053] P1 coordinated by L11 and rhodium: δ177.0ppm, P2 coordinated by L11 and rhodium: δ173.8ppm, P3 coordinated by L1 and rhodium: 34.3ppm, 1 J RhP1 = 251Hz; 1 J RhP2 = 246Hz, 1 J RhP3 = 141Hz, 2 J P1P2 = 279Hz, 2 J P...

Embodiment 3

[0055] Add [Rh(acac)(CO) to a 200mL stainless steel autoclave equipped with a pressure gauge under air atmosphere 2 ] (0.07mmol, 18.1mg) and the L4 monophosphine ligand of 0.28mmol and the L12 bidentate phosphite ligand of 0.14mmol, and 70mL anhydrous toluene, connect the gas line, with synthesis gas (hydrogen: carbon monoxide=1: 1) After replacing the gas in the kettle three times, stir with an electromagnetically driven mechanical stirrer, heat up to 100°C inside the kettle, feed synthesis gas until the total pressure is 2.0MPa, and react at 100°C and 2.0MPa for 1 hour, The rhodium / (bidentate phosphite-monophosphine ligand) complex catalyst HRh(L12)(L4)(CO) was obtained. Its molecular structure is as follows:

[0056] 31 PNMR (Toluene, 162MHz) P1 coordinated by L12 and rhodium: δ177.5ppm, P2 coordinated by L12 and rhodium: δ175.4ppm, P3 coordinated by L4 and rhodium: 34.4ppm, 1 J RhP1 = 248Hz, 1 J RhP2 = 249Hz, 1 J RhP3 = 139Hz, 2 J P1P2 = 282Hz, 2 J P1P3 = 157...

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Abstract

The invention relates to a method for preparing aldehyde through olefin hydroformylation, aiming at mainly solving the problems in the prior art that the normal / isomeric ratio of the product is relatively low and the stability of a catalyst is poor. According to the method for preparing the aldehyde through adopting the olefin hydroformylation, in an olefin hydroformylation reaction, the catalyst is at least one of a complex catalyst I and a complex catalyst II. With the adoption of the technical scheme, the problems above are solved very well and the method can be used for the olefin hydroformylation reaction.

Description

technical field [0001] The invention relates to a method for preparing aldehydes by hydroformylation of olefins. Background technique [0002] Olefin hydroformylation is an important organic synthesis reaction and plays a pivotal role in modern industry. The product aldehyde is a very useful chemical intermediate, which can synthesize a variety of important chemical and chemical products. It is the largest homogeneous catalytic process in production so far. [Trzeciak, A.M.; Ziólkowski, J.J. Coord. Chem. Rev. 1999, 190-192, 883-900.]. Since the 1970s, rhodium catalysts modified with phosphorus-containing ligands have dominated the research on the hydroformylation of olefins due to their outstanding advantages such as high activity, excellent selectivity, and mild reaction conditions, and have become an industrial hydroformylation catalyst. Catalysts for the acylation process, international common hydroformylation process suppliers such as BASF, EvonikOXENO, Perstorp, DOW, e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/50C07C47/02B01J31/24
CPCC07C45/50B01J31/2442B01J2231/321B01J2531/0238B01J2531/822C07C47/02
Inventor 赖春波范曼曼杨旭石李媛高山林黄晓云廖本仁陈建伟高惠敏张春雷
Owner SHANGHAI HUAYI GRP CO
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