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Preparation and application of multiphase asymmetric hydroformylation catalyst

A hydroformylation catalyst and asymmetric technology, applied in the preparation of organic compounds, carbon monoxide reaction preparation, physical/chemical process catalysts, etc., can solve the problems of poor reuse of homogeneous catalysts, influence, unfavorable product purification, etc., to achieve The effect of optimization effect, high chemical stability, and simple synthesis method

Active Publication Date: 2018-05-25
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the homogeneous Rh / BINAP system gave only 25% enantioselectivity in the asymmetric hydroformylation of styrene
At the same time, the homogeneous catalyst has the problem of poor reuse, and its residue in the product also has a very adverse effect on the purification of subsequent products.

Method used

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  • Preparation and application of multiphase asymmetric hydroformylation catalyst
  • Preparation and application of multiphase asymmetric hydroformylation catalyst
  • Preparation and application of multiphase asymmetric hydroformylation catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Under the protective atmosphere of inert gas at 25°C, dissolve 5.0g (S)-5,5'-divinyl-BINAP ligand in 30mL tetrahydrofuran solvent, add 10.0g divinylbenzene monomer, stir evenly, slowly add 0.5 g of free radical initiator azobisisobutyronitrile was stirred for 0.5 h, and then the solution was transferred to a kettle with a polytetrafluoro lining, and solvothermally polymerized at 100° C. for 24 h. After the reaction, the reaction product was vacuum-dried at 65 °C for 10 h to obtain a porous chiral polymer. Take 0.044g Rh(CO) 2 (acac) was dissolved in 8 mL of N,N-dimethylformamide solvent, 2.4 g of polymer material was added, and the mixture was stirred at 100° C. for 3 h under an inert gas atmosphere. Then vacuum dried at 75°C for 10h. Namely the heterogeneous asymmetric hydroformylation catalyst 1.

Embodiment 2

[0018] In Example 2, except that 10.0 g of divinylbenzene was replaced with 10.0 g of styrene, the rest of the operations were the same as those in Example 1, and catalyst 2 was prepared.

Embodiment 3

[0020] In Example 3, except that 10.0 g of divinylbenzene was replaced with 10.0 g of 1,3,5-tris(p-vinylphenyl)benzene, the rest of the operations were the same as those in Example 1, and catalyst 3 was prepared.

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Abstract

The invention discloses a preparation method of a multiphase asymmetric catalyst and belongs to the field of synthesis and application of functional materials. The catalyst is prepared from a metal component and a support. A preparation method of the catalyst support comprises the step as follows: a chiral bidentate phosphine ligand BINAP (5, 5'-divinyl-BIANP) containing vinyl is auto-polymerizedor is co-polymerized with other vinyl monomers with high steric hindrance; the metal component in the multiphase catalyst is Rh element. The periphery of the chiral phosphine ligand in a polymer skeleton is modified with other groups, a chiral pocket shown in the description is formed, so that catalytic performance of the multiphase catalyst in asymmetric hydroformylation can be improved, and enantio-selectivity of a product of the catalyst is increased by about 70% as compared with that of a homogeneous catalyst.

Description

technical field [0001] The invention belongs to the field of functional material synthesis and application, and relates to the preparation and application of a heterogeneous hydroformylation catalyst. Background technique [0002] Asymmetric hydroformylation is one of the most efficient methods for preparing single optically active species. Aldehydes with a single optical activity can be easily reduced or oxidized to obtain alcohols or acids. Although asymmetric hydroformylation has been studied for more than 40 years, it is still a difficult problem in the field of catalysis. Because asymmetric hydroformylation reaction products involve not only enantioselectivity, but also chemoselectivity (hydroformylation vs hydrogenation) as well as stereoselectivity (branched vs linear aldehydes). [0003] The Rh-catalyzed system is mostly studied for asymmetric hydroformylation. When using phosphine-phosphite ligands or bisphosphite ligands, the Rh catalytic system can show higher ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/24C07C45/50C07C47/228
CPCB01J31/061B01J31/063B01J31/2447B01J31/2452B01J2231/321B01J2531/0266B01J2531/821C07B53/00C07B2200/07C07C45/505C07C47/228
Inventor 丁云杰王涛吕元
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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