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pH responsive block polymer immobilized with L-proline, and applications thereof

A block polymer and proline technology, which is applied in the preparation of organic compounds, organic compound/hydride/coordination complex catalysts, asymmetric synthesis, etc., can solve the problems of inconvenient operation and energy consumption, and achieve improved The effect of catalytic yield and selectivity

Active Publication Date: 2018-06-15
TAIYUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This temperature-responsive polymer with immobilized L-proline can not only achieve high conversion rate and high stereoselectivity of catalytic products, but also can be recycled, but the catalytic reaction needs to be carried out at a higher temperature, which not only consumes energy, but also Inconvenient to operate

Method used

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  • pH responsive block polymer immobilized with L-proline, and applications thereof
  • pH responsive block polymer immobilized with L-proline, and applications thereof
  • pH responsive block polymer immobilized with L-proline, and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Preparation of Macromolecular Chain Transfer Agent Polyvinyl Alcohol Trithiocarbonate PEG-DDMAT

[0023] Put 1 g of 2-(dodecyltrithiocarbonate)-2-methylpropionic acid DDMAT in a dry round bottom flask, add 5 mL of dichloromethane to dissolve it, and add it dropwise under nitrogen atmosphere 5 mL of dichloromethane solution dissolved with 1 mL of oxalyl chloride was stirred sufficiently at room temperature for 5 hours. After the reaction, the system was dissolved in 5 mL of dichloromethane and rotary steamed 3 times to ensure removal of excess oxalyl chloride. Add 5 mL of dichloromethane solution containing 1 g of polyvinyl alcohol PEG-OH (1000) into the flask with the product from the previous step, and fully react with magnetic stirring at room temperature for 24 hours. The reaction solution is concentrated by rotary evaporation, and 20 mL of n-hexane is added to precipitate A yellow product was obtained. The product was dissolved in 5 mL of dichloromethane, concentra...

Embodiment 2

[0032] Preparation of Macromolecular Chain Transfer Agent Polyvinyl Alcohol Trithiocarbonate PEG-DDMAT

[0033] Put 2g of 2-(dodecyltrithiocarbonate)-2-methylpropionic acid DDMAT in a dry round bottom flask, add 10mL of dichloromethane to dissolve it, and add it dropwise under nitrogen atmosphere 10 mL of dichloromethane solution dissolved with 1 mL of oxalyl chloride was stirred fully at room temperature for 10 h. After the reaction, the system was dissolved in 10 mL of dichloromethane and rotary steamed 5 times to ensure the removal of excess oxalyl chloride. Add 10 mL of dichloromethane solution containing 2 g of polyvinyl alcohol PEG-OH (1000) into the flask with the product from the previous step, and fully react with magnetic stirring at room temperature for 24 hours. The reaction solution is concentrated by rotary evaporation, and 20 mL of n-hexane is added to precipitate A yellow product was obtained. The product was dissolved in 5 mL of dichloromethane, concentrated ...

Embodiment 3

[0039] Add the pH responsive block polymer PEG-b-P (DEAEMA-co-ProlA) of immobilized L-proline that the embodiment 1 that adds the amount of substrate p-nitrobenzaldehyde substance 10% as catalyst , 0.15mml p-nitrobenzaldehyde, 0.081 cyclohexanone and 1 mL H2O, add NaOH to adjust the pH to 7~8, react at room temperature for 24 hours, after the reaction is completed, feed CO into the system 2 , adjust the pH of the system to acidic, extract the product three times with diethyl ether (3×10mL), combine the organic phases, concentrate, and dry. The conversion rate is 92% and the anti / syn value is 92 / 8 according to the H NMR spectrum.

[0040] The catalytic system after product separation, add 0.15mml p-nitrobenzaldehyde, 0.081 cyclohexanone, and use H 2 O is calibrated to 1mL, adjust the pH to 7~8, react at room temperature for 24 hours, and pass CO into the system after the reaction is completed. 2 , adjust the pH of the system to acidity, extract the product three times with eth...

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Abstract

The invention belongs to the field of high molecular catalyst and synthesis thereof, and more specifically relates to a pH responsive block polymer immobilized with L-proline, and applications thereof. According to a preparation method of the pH responsive block polymer immobilized with L-proline, synthesized methoxyl polyethylene glycol trithiocarbonate PEG-DDMAT is taken as a large molecular chain transferring agent, reversible addition fragmentation chain transfer polymerization method is adopted to realize copolymerization of amino group protected functionalized L-proline Boc-ProIA, and pHresponsive monomer diethylaminoethyl methacrylate DEAEMA; and at last amino deprotection of an obtained polymer is carried out so as to obtain the pH responsive block polymer PEG-b-P(DEAEMA-co-ProIA)immobilized with L-proline. The pH responsive block polymer immobilized with L-proline is used for direct catalysis of asymmetric Aldol reaction in a water phase.

Description

technical field [0001] The invention belongs to the field of polymer catalysts and their synthesis, in particular to a pH-responsive block polymer immobilized with L-proline and its application. Background technique [0002] As a typical small organic molecule catalyst, L-proline has the advantages of non-toxicity, harmlessness, wide sources, and low price. Its superior catalytic performance has been widely used in Aldol and other asymmetric carbon-carbon bond formation reactions. However, L-proline itself has disadvantages such as large amount of use, difficulty in recovery, and need to be catalyzed in an organic medium, which limit its application and development. To this end, the researchers immobilized the small molecule L-proline on the polymer material to solve the above problems. The block polymer immobilized with L-proline is capable of core-shell micelles in water, and its hydrophobicity Nuclear energy can effectively increase the local concentration of reaction su...

Claims

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Application Information

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IPC IPC(8): C08F293/00B01J31/06C07B53/00C07C201/12C07C205/45
CPCB01J31/061C07B53/00C07B2200/07C07C201/12C08F293/005C08F2438/03C07C205/45
Inventor 申迎华刘宽徐伟伟唐娱王琴雅邱丽杜海燕
Owner TAIYUAN UNIV OF TECH
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