Preparation and application of a heterogeneous asymmetric hydroformylation catalyst

A hydroformylation catalyst and asymmetric technology, which is applied in the direction of carbon monoxide reaction preparation, organic compound preparation, physical/chemical process catalyst, 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: 2020-09-01
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 a heterogeneous asymmetric hydroformylation catalyst
  • Preparation and application of a heterogeneous asymmetric hydroformylation catalyst
  • Preparation and application of a heterogeneous asymmetric hydroformylation catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Dissolve 5.0g of (S)-5,5'-divinyl-BINAP ligand in 30mL tetrahydrofuran solvent at 25°C under an inert gas atmosphere, add 10.0g of divinylbenzene monomer, stir well, then slowly add 0.5g free radical initiator azobisisobutyronitrile, stirred for 0.5h, then transferred the solution to a polytetrafluoro-lined kettle, and solvothermally polymerized at 100°C for 24h. 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 8mL of N,N-dimethylformamide solvent, 2.4g of polymer material was added, and stirred at 100°C for 3h under an inert gas atmosphere. Then vacuum dry at 75°C for 10 h. That is, heterogeneous asymmetric hydroformylation catalyst 1.

Embodiment 2

[0018] In Example 2, except that 10.0 g of divinylbenzene was replaced by 10.0 g of styrene, other operations were the same as in Example 1 to prepare Catalyst 2.

Embodiment 3

[0020] In Example 3, except that 10.0 g of divinylbenzene was replaced by 10.0 g of 1,3,5-tris(p-vinylphenyl)benzene, the rest of the operations were the same as in Example 1 to prepare Catalyst 3.

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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 synthesis and application of functional materials, and relates to the preparation and application of a heterogeneous hydroformylation catalyst. Background technique [0002] Asymmetric hydroformylation is one of the most effective methods for preparing single optically active substances. Because aldehydes with a single optical activity can be easily reduced or oxidized to give 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 not only involve enantioselectivity, but also include chemoselectivity (hydroformylation vs hydrogenation) and stereoselectivity (branched vs linear aldehydes). [0003] The most widely studied asymmetric hydroformylation reaction is the Rh catalytic system. When using phosphine-phosphite ligands or bisphosphite ligands, the Rh catal...

Claims

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Application Information

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Patent Type & Authority Patents(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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