Method for preparing aldehyde by olefin hydroformylation

A technology of olefin hydroformyl and hydroformyl, which is applied in the direction of carbon monoxide reaction preparation, chemical instruments and methods, organic chemistry, etc., can solve the problems of poor selectivity and low positive-to-isotropic ratio of products, and achieve lower reaction temperature and pressure, high Catalytic activity, the effect of improving catalyst activity

Active Publication Date: 2020-06-30
WANHUA CHEM GRP CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The purpose of the present invention is to provide a kind of α-olefin hydroformylation method in order to solve the problem of low positive difference ratio and poor selectivity in the product in the existing α-olefin hydroformylation technology. Good selectivity and yield, mild reaction conditions, etc.

Method used

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  • Method for preparing aldehyde by olefin hydroformylation
  • Method for preparing aldehyde by olefin hydroformylation
  • Method for preparing aldehyde by olefin hydroformylation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Preparation of NiPd Bimetallic Phosphine-1NiPdP

[0029] Weigh 2.38g NiCl 2 ·6H 2 O, 2.31g Pd(NO 3 ) 2 , 1.56g NaH 2 PO 4 2H 2 O was placed in a beaker, and then 100 mL of deionized water was added, and stirred at a constant temperature at 70°C to dissolve and evaporate to obtain a dehydrated product. The product was dried at 80°C for 10 h and then ground to obtain a solid precursor, which was placed in a tube-type atmosphere resistance furnace, N 2 Calcined at 500°C for 1 h under protection, the crude product was taken out, washed with water and absolute ethanol three times, and vacuum-dried at 80°C for 12 h to obtain the final product NiPdP.

[0030] Preparation of nickel-palladium bimetallic phosphine-2NiPdP

[0031] Weigh 2.38g NiCl 2 ·6H 2 O, 2.31g Pd(NO 3 ) 2 , 2.34g NaH 2 PO 4 2H 2 O was placed in a beaker, and then 100 mL of deionized water was added, and stirred at a constant temperature at 70°C to dissolve and evaporate to obtain a dehydrated pr...

Embodiment 2

[0033] 1-Butene Hydroformylation

[0034] Rh(acac)(CO) 2 (0.35mmol, 90.5mg), phosphine ligand 3.5mmol, nickel-palladium bimetallic phosphine-20.35mmol, 1-butene 5.0L add in the 10.0L reactor, use synthesis gas (H 2 / CO=1) After replacing the reactor three times, stir with an electromagnetically driven mechanical stirrer, heat up to 110°C inside the reactor, feed synthesis gas until the total pressure is 2.0MPa, and react for 2 hours under this condition, the reaction process keep the pressure constant. After the reaction was over, the reaction kettle was taken out and placed in cold water for rapid cooling to stop the reaction. The reaction products were qualitatively analyzed by chromatography-mass spectrometer, quantitatively analyzed by gas chromatography, and quantified by calibration and normalization method. The conversion rate of olefins is 100%, the selectivity of aldehyde is 99.2%, and the positive-to-isotropic ratio is 96:1.

Embodiment 3～6

[0036] Hydroformylation reaction

[0037]According to the experimental method of Example 2, the cocatalyst uses nickel-palladium bimetallic phosphine-1, and 1-butene is replaced by propylene, 1-pentene, 1-hexene, and 1-heptene respectively for hydroformylation. The reaction results are shown in Table 1.

[0038] Table 1 hydroformylation reaction results

[0039] Example Olefin Conversion rate / % selectivity / % Isotropic ratio 3 Acrylic 99 95 90:1 4 1-pentene 96 97 95:1 5 1-Hexene 98 96 93:1 6 1-heptene 97 98 98:1

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Abstract

The invention relates to a method for preparing aldehyde through olefin hydroformylation. The method comprises the steps: enabling alpha-olefin and synthesis gas to enter a hydroformylation reactor; carrying out a contact reaction on alpha-olefin and synthesis gas with a catalyst to generate an aldehyde-containing product, wherein the catalyst comprises a main catalyst and a co-catalyst, the maincatalyst is a complex catalyst and comprises a rhodium complex and a phosphine ligand, the phosphine ligand is tris[2,4-di-tert-butylphenyl]phosphite, and the co-catalyst is a nickel-palladium bimetallic phosphinate. The method has the advantages of high normal-to-abnormal ratio in the product, good selectivity and yield, mild reaction conditions and the like.

Description

technical field [0001] The invention relates to a method for preparing aldehydes by hydroformylation of olefins, belonging to the field of organic synthesis. Background technique [0002] Olefin hydroformylation is an important organic synthesis reaction, which plays a pivotal role in modern industry and is the largest homogeneous catalytic process in production so far. Aldehydes, the products of olefin hydroformylation, are useful chemical intermediates that can be used to synthesize a variety of important chemical and chemical products. [0003] 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. Catalyst for acylation process. Among them, the composition and structure of phosphorus-containing ligands are key factors...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/50C07C47/02B01J27/185
CPCC07C45/50B01J27/1856C07C47/04
Inventor 朱龙龙杨在刚张涛吕英东刘俊贤张明郭启赫石江山翟文超黎源
Owner WANHUA CHEM GRP CO LTD
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