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A kind of propylene hydroformylation catalytic system and method

A technology of propylene hydroformylation catalysis and catalytic system, which is applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, physical/chemical process catalysts, etc. High, expensive epoxy compounds, accelerated butyraldehyde polymerization, etc., to achieve high activity and selectivity, prolong service life, and good stability

Inactive Publication Date: 2011-12-07
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Rh(I) / triphenylphosphine is a widely used catalyst system for the synthesis of butyraldehyde from propylene hydroformylation at present, but the problem is that the amount of noble metal Rh(I) (200mg / L) and triphenylphosphine is large (triphenyl The molar ratio of base phosphine to rhodium is generally 200:1), and the normal / iso ratio of the product butyraldehyde is not high (<20)
The disadvantage of this method is that it will inevitably cause a certain degree of catalyst loss when the ion exchange resin bed processes the reaction mixture, and it is necessary to supplement the catalyst in the reaction system to make it reach a suitable concentration; moreover, this method also needs to add A large additional equipment, which significantly increases the cost of investment and operation
However, epoxy compounds are relatively expensive, and controlling the reaction solution in a weakly alkaline environment will accelerate the polymerization of butyraldehyde, and the impact of the decomposition of epoxy compounds on product quality is not very clear

Method used

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  • A kind of propylene hydroformylation catalytic system and method
  • A kind of propylene hydroformylation catalytic system and method
  • A kind of propylene hydroformylation catalytic system and method

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Experimental program
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Effect test

Embodiment 2

[0041]

[0042] Synthesis of bidentate phosphite L2:

[0043] At -40°C, a solution of binaphthyldiol (1.43g, 5mmol) and triethylamine (5.6mL, 40mmol) in tetrahydrofuran was added dropwise to PCl 3 (0.43mL, 5mmol) in tetrahydrofuran solution, gradually warmed up to room temperature after the dropwise addition, cooled to -40°C after stirring for 2 hours, then added dropwise Compound B (0.82g, 2mmol) and triethylamine (2.8mL, 20mmol ) tetrahydrofuran solution, after the dropwise addition, the temperature was gradually raised to room temperature, and after stirring for 2 hours, it was processed and purified through a silica gel column to obtain the product L2, a white solid, with a yield of 67% (1.39g), 1 HNMR and 31 The structure was identified by PNMR, and the melting point was 249-251°C.

Embodiment 3

[0045]

[0046] Synthesis of bidentate phosphite L3: At room temperature, a toluene solution of compound B (1.0 g, 2.5 mmol) and triethylamine (2.8 mL, 20 mmol) was added dropwise to PCl 3 (0.22mL, 2.5mmol) in toluene solution, heat up and reflux for 2 hours, then cool to room temperature, then add dropwise the toluene solution of 2,2'-biphenol (0.18g, 1mmol) and triethylamine (1.4mL, 10mmol) , after the dropwise addition, the temperature was raised to reflux for 2 hours, cooled and processed, and purified through a silica gel column to obtain the product L3, a white solid, with a yield of 30% (0.31g), 1 HNMR and 31 The structure was identified by PNMR, and the melting point was 145-147°C.

Embodiment 4

[0048]

[0049] Synthesis of bidentate phosphite L4: Add compound C (0.69g, 2mmol) and triethylamine (2.8mL, 20mmol) in tetrahydrofuran dropwise to compound A (0.96g, 4mmol) in tetrahydrofuran at -20°C In the solution, after the dropwise addition, it was gradually raised to room temperature, and after stirring for 24 hours, it was processed, and acetonitrile was added for recrystallization to obtain the product L4, a white crystal, and the yield was 69% (1.05g). 1 HNMR and 31 The structure was identified by PNMR, and the melting point was 175-178°C.

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Abstract

The invention relates to a propylene hydroformylation catalyst system and a method for catalyzing synthesis of butyraldehyde. In the present invention, in the propylene hydroformylation reaction system catalyzed by triarylphosphine-Rh(I), by using appropriate types and quantities of additives, such as bisphosphite, the performance of the Rh(I) / triarylphosphine catalyst can be significantly improved The activity and the positive-iso ratio of butyraldehyde in the product (molar ratio of n-butyraldehyde / isobutyraldehyde>20), and significantly prolong the service life of the bisphosphite ligand, and significantly reduce the amount of triarylphosphine. This type of catalyst system is characterized by higher activity and selectivity than third-generation Rh(I) / triphenylphosphine catalysts and better stability than fourth-generation Rh(I) / bisphosphite catalysts, so The novel catalyst system provided by the present invention can overcome the shortcomings of the third and fourth generation catalysts, reduce the cost of industrialized production of propylene hydroformylation, and provide a new catalyst technology for its industrial application.

Description

[0001] This application is a divisional application of an invention patent application with an application date of December 22, 2006, an application number of 200610147735.2, and an invention title of "A Catalytic System and Method for Propylene Hydroformylation". technical field [0002] The invention uses rhodium salt, triaryl phosphine and bisphosphite additives to prepare a novel catalyst system for propylene hydroformylation, and is used in the method for catalyzing propylene hydroformylation to synthesize butyraldehyde. In the propylene hydroformylation reaction system catalyzed by triarylphosphine-Rh(I), the present invention finds that the efficiency of the Rh(I) / triarylphosphine catalyst can be significantly improved by using bisphosphite additives, such as bisphosphite. The activity and the butyraldehyde in the product are positively different (the molar ratio of n-butyraldehyde / isobutyraldehyde>20), and significantly prolong the service life of the bisphosphite li...

Claims

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Application Information

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IPC IPC(8): B01J31/24C07C47/02C07C45/50C07F9/145
Inventor 丁奎岭侯雪龙李欣朱霞珍吴良泉蒋文赖春波陈建伟
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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