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Application of a Chiral Polymer Catalyst in Asymmetric Reaction

A polymer and catalyst technology, applied in the field of the preparation of heterogeneous catalysts, can solve the problems of difficult catalyst recovery and low activity of heterogeneous asymmetric reaction catalysts, and achieve the effects of high stability, shortened reaction time, and improved activity.

Active Publication Date: 2019-09-27
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

[0006] In view of the above defects and improvement needs of the prior art, the present invention provides a preparation method and application of a chiral porous polymer, the purpose of which is to improve the catalytic activity and stability of heterogeneous asymmetric reactions by optimizing the synthesis raw materials and processes , in order to solve the problems of difficult recovery of existing homogeneous asymmetric reaction catalysts and low activity of heterogeneous asymmetric reaction catalysts

Method used

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  • Application of a Chiral Polymer Catalyst in Asymmetric Reaction
  • Application of a Chiral Polymer Catalyst in Asymmetric Reaction
  • Application of a Chiral Polymer Catalyst in Asymmetric Reaction

Examples

Experimental program
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Effect test

Embodiment 2

[0037] Dissolve 5.0g of (S)-5,5'-divinyl-BINAP ligand in 50mL tetrahydrofuran solvent at 25°C under an inert gas atmosphere, add 50.0g 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 [RuCl 2 (benzene)] 2 Dissolve in 8mL of N,N-dimethylformamide solvent, add 2.4g of polymer material, and stir at 100°C for 3h under an inert gas atmosphere. Then vacuum dry at 75°C for 10 h. The heterogeneous catalyst 1 for the asymmetric reaction of β-keto esters was obtained.

Embodiment 3

[0039] In Example 3, except that 5.0g (S)-5,5'-divinyl-BINAP ligand was replaced by 5.0g (S)-4,4'-divinyl-BINAP ligand, the rest of the operations were the same as in Example 2 Similarly, catalyst 2 was prepared.

Embodiment 4

[0041] In Example 4, except that 5.0g (S)-5,5'-divinyl-BINAP ligand was replaced with 12.5g (S)-5,5'-divinyl-BINAP, the rest of the operations were the same as in Example 2, Catalyst 3 was prepared.

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Abstract

The invention discloses the application of a chiral polymer catalyst in an asymmetric reaction, and belongs to the field of material synthesis and application. The phosphine-containing polymer consists of vinyl-containing chiral bidentate phosphine ligand BINAP (2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) and its derivatives and other vinyl groups It is formed by mixing comonomers. This type of vinyl polymer material has a high specific surface area and a large porosity, and at the same time has excellent thermal stability and chemical stability. One or more of metals Ru, Rh, Ir, Pa, Au and Cu are used as active components in the heterogeneous catalyst. Because the chiral ligands are uniformly embedded and highly dispersed in the polymer skeleton, the dispersion of the metal on the catalyst is higher, and higher catalytic activity is achieved. The heterogeneous catalyst is suitable for various reaction processes such as intermittent tank reaction, continuous fixed bed reaction and trickle bed reaction. When it is applied to catalytic tank type asymmetric hydrogenation reaction, high yield of target product and enantioselectivity greater than 96% can be obtained.

Description

technical field [0001] The invention belongs to the field of heterogeneous catalysis, and is suitable for the preparation method of heterogeneous catalysts of chiral phosphine-containing organic polymers loaded with metals which are suitable for catalyzing the asymmetric hydrogenation reaction of β-keto esters. Background technique [0002] Asymmetric hydrogenation of unsaturated compounds containing carbon-carbon double bonds (C=C), carbon-oxygen double bonds (C=O) and carbon-nitrogen double bonds (C=N) with hydrogen molecules catalyzed by transition metal complexes Reaction is an important method for the synthesis of optically active compounds. This method is highly efficient, highly atom-economical, and environmentally friendly. After more than 40 years of development, asymmetric catalytic hydrogenation has been successfully applied to various types of chiral amino acids, chiral alcohols, chiral amines, and chiral carboxylic acids. Asymmetric Synthesis of Sexual Compound...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/24C07C67/31C07C69/675C07C69/732
Inventor 丁云杰王涛吕元
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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