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Porous chiral organic polymer catalyst and preparation method thereof

A catalyst and polymer technology, applied in the field of porous chiral organic polymer catalysts and their preparation, can solve the problems of difficult catalyst recovery and industrial application, achieve excellent stability, reduce catalyst costs and subsequent product separation costs, and increase active effect

Active Publication Date: 2019-06-18
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

However, the phosphine ligand in the catalyst is very sensitive to air, and the preparation, storage, transportation and application of the catalyst require an anhydrous and oxygen-free environment, making industrial application difficult
[0005] In 2016, Szewczyk et al. (ChemCatChem, 2016, 8, 3575) reported a chiral 1,2-diphenylethylenediamine-based amine ligand. After coordinating it with a zinc complex, it Used in the asymmetric hydrogenation reaction of aryl ketones and imines, it shows high catalytic activity and chiral selectivity, but this homogeneous catalytic system faces the problem of difficult catalyst recovery

Method used

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  • Porous chiral organic polymer catalyst and preparation method thereof
  • Porous chiral organic polymer catalyst and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0033] Dissolve 0.7g N,N-bis(4-vinylbenzyl)-1,2-diphenylethylenediamine in 15mL N,N-dimethylformamide solvent at 298K and inert gas Ar protection atmosphere , while adding 0.6g of 1,3,5-tri-p-styrylbenzene, and then adding 0.0325g of azobisisobutylcyanide, and stirring for 1h. The stirred solution was moved to an autoclave, and stood at 373K for 24h. After cooling to room temperature, it was washed three times with methanol solvent, and then dried in vacuum at low temperature to obtain a white powdery solid. The solid was added to a two-necked flask, 30ml of dichloromethane was added, and after the air was removed through three cycles of liquid nitrogen freezing, vacuum and melting, 43.3mg of dichloro(p-methylcumene)ruthenium(II) dichloride was added. After polymerizing, heat to 323K under stirring. After 2 hours, the solvent was removed by rotary evaporation, and a dark gray solid powder was obtained after vacuum drying, which was a porous chiral organic polymer catalyst. ...

Embodiment 2

[0035] In Example 2, 0.26 g of divinylbenzene was weighed to replace 1,3,5-tri-p-styrylbenzene, and the rest of the catalyst synthesis process was the same as in Example 1.

Embodiment 3

[0037] The catalysis prepared in Example 1 was used in the chiral hydrogenation reaction of acetophenone, and 0.0853 g of the catalyst was placed in an autoclave, and 0.24 g of acetophenone, 10 ml of isopropanol, and 0.0059 g of potassium hydroxide were added, and hydrogen was replaced in the autoclave. Gas three times, stir, heat up to 323K, and react for 5h. It has a conversion rate of 59% and an ee value of 21.2%.

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Abstract

The invention discloses a porous chiral organic polymer heterogeneous catalyst based on a chiral 1,2-diphenylethylenediamine metal complex, and a preparation method thereof and belongs to the field ofsynthesis and application of functional materials. The heterogeneous catalyst takes chiral 1,2-diphenylethylenediamine and the coordinated metal thereof as active species, and can be obtained throughtwo methods: method 1, carrying out copolymerization between alkylene chiral 1,2-diphenylethylenediamine and another monomer to obtain a porous organic polymer, and coordinating with the metal complex; method 2, firstly coordinating alkylene chiral 1,2-diphenylethylenediamine with the metal complex, and copolymerizing with another monomer. The heterogeneous catalyst of this type is applied to reactors of a fixed bed, a slurry bed, a trickle bed and the like. According to the heterogeneous catalyst provided by the invention, the catalyst is applied to reaction technologies of chiral hydrogenation, chiral hydrogen transfer and chiral hydrosilylation of aromatic ketone or aromatic amine, and the advantages of high-activity and high selectivity of the homogeneous phase metal complex, and easyseparation of the heterogeneous catalyst are remained.

Description

technical field [0001] The field of the invention belongs to the field of synthesis and application of functional materials, and in particular relates to a porous chiral organic polymer catalyst and a preparation method thereof. Background technique [0002] In recent years, the design and synthesis of heterogeneous catalysts supported by porous organic polymers has gradually become a new research hotspot. Compared with traditional activated carbon, silica, alumina and other porous material supports, porous organic polymers can be designed to embed specific groups or ligands into stable polymer materials due to the diversity of organic chemical synthesis methods. So it can be applied in different fields. In addition, after the porous organic polymer is coordinated with different metal complexes, the metal can be highly dispersed in the porous organic polymer carrier, which greatly improves the utilization efficiency of the metal, and can inhibit the loss of the metal and im...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22B01J35/10C07B53/00C07C29/145C07C33/22
Inventor 丁云杰张岩吕元
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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