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Novel polymer chiral catalyst, preparation method, and applications thereof

A chiral catalyst and polymer technology, applied in chemical instruments and methods, physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, etc. Churn and other issues

Inactive Publication Date: 2013-12-18
NANJING UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above-mentioned supported catalysts graft L-proline onto the carrier through methods such as covalent bonds, ionic bonds or weak interactions. There are many problems in the catalysts prepared by these methods, such as the catalyst is unstable, easy to run off, and the load Quantity cannot be adjusted, etc.

Method used

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  • Novel polymer chiral catalyst, preparation method, and applications thereof
  • Novel polymer chiral catalyst, preparation method, and applications thereof
  • Novel polymer chiral catalyst, preparation method, and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] A kind of preparation method of polymer chiral catalyst

[0019] Take 2.54g of N-isopropylacrylamide and 0.56g of (s)-O-acryloyl-4-hydroxy-L-proline, 0.041g of initiator AIBN, and 15ml of solvent DMF into the reaction eggplant bottle in sequence, and stir Deoxygenate after dissolution. 80 DEG C of oil baths were reacted for 6 hours, after the end of the reaction, the product was precipitated with 120 ml of anhydrous ether as a precipitating agent, centrifuged, and the precipitate was placed in a vacuum oven for drying at 55 DEG C to obtain a catalyst, wherein m:n=9:1, ( 1 See HNMR figure 1 ).

Embodiment 2

[0021] A kind of preparation method of polymer chiral catalyst

[0022] Take 3.36g of N-isopropylacrylamide and 1.64g of (s)-O-acryloyl-4-hydroxy-L-proline, 0.061g of initiator AIBN, and 15m1 of solvent DMF into the reaction eggplant bottle in sequence, and stir Deoxygenate after dissolution. React in an oil bath at 80°C for 6 hours. After the reaction, use 120ml of anhydrous ether as a precipitant to precipitate the product, centrifuge, and dry the precipitate in a vacuum oven at 55°C to obtain a catalyst, wherein m:n=4:1.

Embodiment 3

[0024] Take by weighing 0.5g prepared catalyst, 0.0756g 4-nitrobenzaldehyde, measure 2ml cyclohexanone, 2mlH 2 O, react at 30°C for 24h (see Table 1 for catalytic performance data). After the reaction is completed, the system is heated to 70° C., and the catalyst is recovered by centrifugation while it is hot.

[0025] The reaction formula is:

[0026]

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Abstract

The invention provides a soluble temperature sensitive polymer chiral catalyst, namely a polymer material copolymerized by L-proline derivatives and N-isopropylacrylamide. The catalyst is prepared by following steps: taking azodiisobutyronitrile (AIBN) as the initiator, and N,N-dimethylformamide (DMF) as the solvent, and then carrying out copolymerization reactions between N-isopropylacrylamide and free radicals of (s)-O-acryloyl-4-hydroxy-L-proline. The catalyst is capable of being used to catalyze asymmetric aldol condensation reactions, and has the advantages of high catalytic activity and good stereo-selectivity. The catalyst is capable of being used in an ordinary organic solvent system; furthermore, because the catalyst has a temperature sensitive effect, the catalyst is easy to be separated from the water system and recycled, the catalyst is an important way to achieve green organic synthesis, and has a vast application prospect.

Description

1. Technical field: [0001] The invention relates to a polymer chiral catalyst and a preparation method thereof, which can be used to catalyze an asymmetric aldol condensation reaction, especially the temperature-sensitive effect of the catalyst can be used for the separation and recovery of the catalyst. 2. Background technology: [0002] Smart material is a new type of material that can sense and respond to the environment and has the ability to discover functions. It is a high-tech cutting-edge material that has attracted the attention of many scientists in recent years. It has good application prospects in the fields of medicine, civil engineering, aerospace, machinery industry, and national defense industry. [0003] Smart materials include temperature-sensitive materials, pH-sensitive materials, light-sensitive materials, etc. Among them, temperature-sensitive polymer materials are a popular category. Chinese invention patent (CN 86103237A) reports a high polymer temp...

Claims

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Application Information

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IPC IPC(8): B01J31/06B01J31/22
Inventor 仝庆董玉娇刘玉炳华林范以宁
Owner NANJING UNIV
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