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Catalytic rectification process and device for chiral resolution of 1-phenylethylamine by using lipase

A technology of phenylethylamine catalytic refinement and catalytic rectification tower, which is applied in the chemical industry, distillation separation, organic chemistry, etc., can solve problems such as difficult to obtain product conversion rate, and achieve reduced contact time, high reaction conversion rate, and optical purity high effect

Inactive Publication Date: 2018-07-17
TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional kinetic resolution process of racemic 1-phenylethylamine uses the tank reactor method, which has the advantages of simple operation and low equipment investment, but due to the equilibrium limitation in the reaction system, it is difficult to obtain higher products Conversion rate

Method used

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  • Catalytic rectification process and device for chiral resolution of 1-phenylethylamine by using lipase

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The operating pressure of the catalytic rectification column used was 300 mBar. 1-Phenylethylamine is continuously fed from the upper feed port of the reaction section after being preheated to 60°C. Ethyl butyrate is continuously fed from the feed port at the lower part of the reaction section after being preheated to 60°C. The molar ratio of feed 1-phenethylamine to ethyl butyrate is 1:3. 1-Phenylethylamine and ethyl butyrate react under the catalysis of the lipase catalyst loaded in the reaction section to generate R-amide and ethanol. The temperature of the tower kettle is 100-101°C, and the tower kettle reboiler provides the ascending gas phase for the upper sections. The top reflux ratio of the catalytic distillation tower is 3.4, and the temperature is 50-51°C. Ethanol is extracted from the top of the catalytic rectification tower, and R-amide and unreacted S-1-phenylethylamine and ethyl butyrate are extracted from the bottom of the tower.

[0024] After testin...

Embodiment 2

[0026] The operating pressure of the catalytic rectification column used was 500 mBar. 1-Phenylethylamine is continuously fed from the upper feed port of the reaction section after being preheated to 60°C. Methyl butyrate is fed continuously from the feed port at the lower part of the reaction section after being preheated to 60°C. The molar ratio of feed 1-phenylethylamine to methyl butyrate is 1:2. 1-Phenylethylamine and methyl butyrate react under the catalysis of the lipase catalyst loaded in the reaction section to generate R-amide and methanol. The temperature of the tower kettle is 98-99°C, and the tower kettle reboiler provides the rising gas phase for the upper sections. The top reflux ratio of the catalytic rectification tower is 2.2, the temperature is 47-48°C, and the methanol product is extracted from the top.

[0027] After testing, the conversion rate of R-1-phenylethylamine in the catalytic rectification tower is ≥99.5%, the mass fraction of methanol in the p...

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Abstract

The invention provides a chemical reaction separation device and method, and specifically relates to a catalytic rectification tower and process for catalyzing kinetic chiral resolution of 1-phenylethylamine by using lipase. The rectification tower comprises a condenser and a reboile; and the rectification tower is characterized in that a rectification tower reaction section is provided with a catalyst bag, and the interior of the catalyst bag is filled with the lipase supported on resin; and due to selective catalytic action of the lipase, a carboxylate ester is used as an acyl donor to reactwith R-type 1-phenylethylamine to form an R-type amide, and S-type 1-phenylethylamine does not participate in a reaction. The device and method provided by the invention can realize that a conversionrate of a reaction of the 1-phenylethylamine reaches 99% or more; the R-type amide product with enantiomeric excess (ee) of greater than 99% and the S-type 1-phenylethylamine product with enantiomeric excess (ee) of greater than 98% are obtained; and production processes are greatly simplified, and energy consumption and operating cost are reduced.

Description

technical field [0001] The present invention relates to a catalytic rectification process and device for dismantling chiral 1-phenylethylamine using lipase as a catalyst. Kinetic resolution of racemic 1-phenylethylamine to produce single-enantiomer chiral 1-phenylethylamine with an enantiomeric excess ee of over 98%. Background technique [0002] The molecular weight and molecular structure of chiral compounds are the same, but the left and right arrangements are opposite, such as the real object and its enantiomer in the mirror; its melting point, solubility, and types of chemical reactions that can occur are very similar. Although the physical and chemical properties are close, biochemical reactions occurring in organisms (such as immune recognition of antigens and antibodies, specific catalysis of enzymes for substrates, etc.) will recognize each molecule based on strict chiral matching. Therefore, although the chemical formula and molecular structure of a pair of chiral...

Claims

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Application Information

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IPC IPC(8): C07C209/88C07C211/27B01D3/00B01J8/00
CPCB01D3/009B01J8/008C07B2200/07C07C209/88C07C211/27Y02P20/10
Inventor 王红星王晓达王伟粲邱挺叶长燊黄智贤杨臣杨金杯陈锦溢王清莲李玲
Owner TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY
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