Method for producing high carbon aldehyde through using olefin hydroformylation reaction

A technology for olefin hydroformylation reaction, which is applied to the preparation of carbon monoxide reaction, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of loss of homogeneous catalyst, decrease in activity, etc. Simple preparation process and high reactivity

Active Publication Date: 2015-06-17
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0016] To sum up, the general idea of ​​the above-mentioned studies on homogeneous heterogeneity is to make the organic functional group act as a homogeneous catalyst, so that the homogeneous catalyst can be immobilized on the heterogeneous carrier. The biggest problem in these methods is the homogeneous catalyst. The problem of the loss of the homogeneous catalyst and the decrease in the activity of the homogeneous catalyst on the carrier, these two problems are the biggest bottlenecks restricting the homogeneous solid support of hydroformylation

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  • Method for producing high carbon aldehyde through using olefin hydroformylation reaction
  • Method for producing high carbon aldehyde through using olefin hydroformylation reaction
  • Method for producing high carbon aldehyde through using olefin hydroformylation reaction

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Embodiment 1

[0055] In an ice-water bath and a nitrogen atmosphere, in a 100mL three-necked round-bottomed flask with a magnetic stirrer, add 0.5g of magnesium powder and 10mL of anhydrous ether in turn, and stir the resulting reaction mixture for 2 hours under these conditions, and then add 4g of A mixed solution of p-bromostyrene and 10mL of anhydrous ether, the resulting reaction mixture was stirred under these conditions for 2 hours, then a mixed solution of 6g of phosphorus trichloride and 10mL of anhydrous ether was added dropwise, and the resulting reaction mixture was stirred under these conditions After 2 hours, add 10 mL of water and stir for 1 hour, then extract the reaction mixture with 90 mL of diethyl ether solution for 3 times, combine the diethyl ether extracts, filter and remove the solvent by rotary evaporation, and the obtained primary product is purified by silica gel column chromatography, which is ready to use Silica gel was used as the stationary phase, and a mixed so...

Embodiment 2

[0057] Under 298K and a nitrogen gas protection atmosphere, 10.0 grams of tris (4-vinylphenyl) phosphine was dissolved in 100.0 ml of tetrahydrofuran solvent, and 1.0 grams of free radical initiator azobisisobutyronitrile was added to the above solution, stirred for 2 Hour. The stirred solution was moved to an autoclave, and polymerized by solvothermal polymerization at 373K under a nitrogen atmosphere for 24 hours. After the above-mentioned polymerized solution is cooled to room temperature, the solvent is vacuumed away at room temperature to obtain a large-surface-area hierarchical porous structure organic ligand polymer carrier formed by tris(4-vinylphenyl)phosphine polymerization. Figure 4 It is a schematic diagram of the technical route of tris(4-vinylphenyl)phosphine ligand polymer carrier polymerization. It is determined by analysis that the degree of polymerization n of the ligand polymer is 450-550, and it has macropores, mesopores and micropores. Hierarchical pore ...

Embodiment 3

[0059] Under 298K and a nitrogen gas protection atmosphere, weigh 3.14 mg of rhodium acetylacetonate dicarbonyl (I) and dissolve it in a three-necked flask of 100.0 ml of tetrahydrofuran solvent, stir and dissolve, add 1.0 g of tris(4-ethylene) prepared in Example 2 The organic ligand polymer formed by the polymerization of phenyl)-based phosphine, the mixture was stirred at 298K and nitrogen gas protection atmosphere for 24 hours, and then the solvent was vacuumed off at room temperature, and the organic ligand polymer self-loaded metal was obtained. Components of solid heterogeneous catalysts. The heterogeneous catalyst prepared above was applied to the hydroformylation reaction of 1-dodecene in a trickle bed. The trickle bed is a stainless steel tube reactor with an inner diameter of 9mm, the catalyst loading is 1.0ml, the synthesis gas pressure is 1.0MPa, and the volume space velocity is 5000h -1 . 1-Dodecene is injected into the reactor with a double plunger micropump, ...

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Abstract

The invention relates to a method for producing high carbon aldehyde through using an olefin hydroformylation reaction. The method is characterized in that the olefin hydroformylation reaction of a C6-C20 olefin raw material and synthetic gas is carried out in the presence of a solid heterogeneous catalyst in a trickle bed, the solid heterogeneous catalyst is composed of a metal component and an organic ligand polymer, the metal component is one or more of Rh, Ir and Co, the organic ligand polymer is a polymer having a large specific surface area and a hierarchical pore structure and formed by polymerizing an organic ligand monomer containing P, an alkylene group and optional N through a solvothermal polymerization technology, and the metal component and the P atom or N in the skeleton of the organic ligand polymer form a coordination bond and exist in a monoatomic dispersion state. The method has the advantages of simple and easy reaction process, suitableness for industrial large-scale production, excellent reaction activity and selectivity, and high normal/isomeric ratio of the product aldehyde.

Description

technical field [0001] The invention relates to a method for producing high-carbon aldehydes (that is, aldehydes with more than 6 carbons) by olefin hydroformylation, and belongs to the technical field of heterogeneous catalysis. Background technique [0002] The hydroformylation reaction is a typical atom economy reaction, and its catalytic process and catalyst research have a history of nearly 60 years. Currently, approximately more than 10 million tons of aldehydes and alcohols per year are produced worldwide using olefin hydroformylation technology. This reaction can generate aldehydes from raw material olefins under less severe conditions, and the product aldehydes can be further converted into alcohols by hydrogenation. Homogeneous catalytic systems have high catalytic activity and target product selectivity under mild reaction conditions, but the separation of catalysts and reaction materials is difficult, which hinders the large-scale industrial application of homog...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/50C07C47/02C07C47/228B01J31/24
CPCB01J31/24B01J2531/822C07C45/505C07C47/228C07C47/02Y02P20/50
Inventor 丁云杰严丽姜淼林荣和
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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