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Catalyst for producing aldehyde through hydroformylation of alkene and application thereof

A technology for alkene hydroformyl and catalyzing alkene hydroformyl, which is applied in physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, carbon monoxide reaction preparation, etc., can solve the problem that the activity of rhodium phosphine catalyst needs to be improved, Problems such as poor catalyst stability, to achieve the effect of simple separation, good catalytic performance, and guaranteed stability

Inactive Publication Date: 2012-09-12
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in industrial production, there are problems such as the activity of rhodium-phosphine catalysts to be improved, poor catalyst stability, catalyst separation and recycling, etc. These problems are the difficulties faced by the industry when adopting expensive rhodium-phosphine catalytic systems

Method used

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  • Catalyst for producing aldehyde through hydroformylation of alkene and application thereof
  • Catalyst for producing aldehyde through hydroformylation of alkene and application thereof
  • Catalyst for producing aldehyde through hydroformylation of alkene and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1: L1 Synthesis:

[0022] 1-Butyl-3-methylimidazolium hexafluorophosphate was dissolved in dry tetrahydrofuran, under nitrogen protection, at -78°C, 1.05 equivalents of n-butyllithium ( n -BuLi), reacted for 1 hour after the drop, then slowly added 1.05 equivalents of diphenylphosphine chloride dropwise, and slowly rose to room temperature overnight after the drop. The reaction solution was washed with water, dried over anhydrous magnesium sulfate, crystallized with dichloromethane and absolute ethanol, and dried in vacuum to obtain white crystals which were ligands L1 , with a structure such as L1 shown.

Embodiment 2

[0023] Example 2: L2 Synthesis:

[0024] N-ethylbenzimidazole was dissolved in dry tetrahydrofuran, and 1.05 equivalents of TMEDA and n -BuLi, reacted for 1 hour, then added diphenylphosphine chloride dropwise, slowly raised to room temperature after dropping, stirred overnight, and separated by column chromatography to obtain a yellow viscous liquid. The yellow liquid was dissolved in dry dichloromethane. Under nitrogen protection and at -78°C, 1.05 equivalents of methyl trifluoromethanesulfonate was added dropwise. After the drop was completed, it was slowly raised to room temperature, stirred overnight, and the solvent was removed by rotary evaporation. Washed with ether to give a white solid L2 , with a structure such as L2 shown.

Embodiment 3

[0025] Example 3: L3 Synthesis:

[0026] L3 synthetic method and L2 The synthetic method of is the same, and the starting material is replaced by N-methylimidazole. structure like structure L3 shown.

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Abstract

The invention discloses a catalyst for producing aldehyde through hydroformylation of alkene, wherein, the catalyst comprises ionic organic phosphorus ligands and rhodium compounds; the molar ratio of the ionic organic phosphorus ligands and the rhodium compounds is 1 to 20:1; the ionic organic phosphorus ligands are ionic compounds and comprise positive ions and negative ions; the rhodium compounds are neutral rhodium complexes or ionic rhodium compounds; the catalyst is used for catalyzing the reaction of aldehyde preparation through hydroformylation of alkene, wherein, the related alkene is Alpha-alkene that is a straight chain of C3 to C12; and an adopted solvent is room-temperature imidazolyl or pyridyl ionic liquid. The catalyst is characterized by favorable catalytic performance, prolonged service life and circulating application in the liquid phase reaction of aldehyde production through hydroformylation of alkene.

Description

technical field [0001] The present invention relates to olefins and synthesis gas (CO / H 2 ) A catalyst for preparing aldehyde by hydroformylation reaction, and the recycling of the catalyst. Background technique [0002] Under the action of a rhodium phosphine catalyst composed of an organophosphine ligand and a rhodium complex, olefins and synthesis gas (CO / H 2 ) to prepare aldehydes through hydroformylation, and then use aldehydes as intermediates to synthesize higher-carbon alcohols. It has developed into an important industrial process for the production of long-chain detergent alcohols, and has been widely used worldwide (US 6225507. 2001; US 4769498. 1988; WO 9733854. 1997; Eur Chem News, 1999, 70, (1845): 22; Chem Inno, 2001, 31 (7): 39) 47). However, in industrial production, there are problems such as the activity of rhodium-phosphine catalysts to be improved, poor catalyst stability, catalyst separation and recycling, etc. These problems are the difficulties face...

Claims

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Application Information

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IPC IPC(8): B01J31/24C07F19/00C07F15/00C07C45/50C07C47/02
Inventor 刘晔尤洪星姚卫民陈胜洁路勇
Owner EAST CHINA NORMAL UNIV
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