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Method for effectively separating raceme and preparing homochiral substance

A racemization and system technology, applied in chemical instruments and methods, molecular sieve catalysts, chemical/physical processes, etc., can solve problems affecting metal and enzyme catalytic activity, less application of phenethylamine racemization, low reaction selectivity, etc. , to achieve the effect of preventing mutual influence and poisoning, shortening the diffusion distance, and easy separation and recovery

Inactive Publication Date: 2012-03-28
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the main disadvantages of these catalysts are low reaction efficiency, low reaction selectivity, harsh reaction conditions, etc.
At the same time, the presence of metals may also cause interactions with enzymes, affecting the catalytic activity of metals and enzymes, and thus cannot effectively and highly selectively obtain pure chiral substances.
[0004] The noble metal Pt catalyst has good catalytic activity for hydrodehydrogenation, but because Pt will combine with sulfur-containing and nitrogen-containing substances in the enzyme, the enzyme and Pt will lose their activity at the same time, so it is rarely used in the racemization of phenethylamine. There are few reports

Method used

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  • Method for effectively separating raceme and preparing homochiral substance
  • Method for effectively separating raceme and preparing homochiral substance
  • Method for effectively separating raceme and preparing homochiral substance

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1 Reaction conditions: 0.15 mmol of phenylethylamine, 50 mg of immobilized enzyme CALB, 100 mg of microcapsule catalyst, and 0.35 mmol of esterification reagent were added to 2 mL of toluene. In a hydrogen atmosphere, the reaction temperature is 70 o C, reacted for 30 hours. The homochiral product R-phenethylamine was obtained with a yield of 80%.

Embodiment 2

[0021] Example 2 Using the same conditions as in Example 1, changing the amount of catalyst to 50 mg, and reacting for 60 hours, a homochiral product was obtained with a yield of 78%.

Embodiment 3

[0022] Example 3 Using the same conditions as in Example 1, changing the amount of catalyst to 150 mg, and reacting for 20 hours, a homochiral product was obtained with a yield of 75%.

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Abstract

The invention belongs to the technical field of chiral compound preparation, and specifically relates to a method for effectively separating raceme and preparing a homochiral substance. According to the invention, zeolite microcapsules (Pt@S1) with sealed catalytically active silicalite-1 are adopted as a catalyst; the catalyst is used in concerted catalysis with lipase (CALB), such that a homochiral substance is obtained. With the method, mutual influences between an active species Pt and enzyme, and intoxication are effectively prevented; one-step reaction of dynamic kinetic resolution can be realized with high efficiency; reaction efficiency can be improved; and reaction cost can be reduced. Also, according to the invention, with the tight protection of the zeolite microcapsules, loss of active species can be effectively prevented, and the catalyst can recycled and repeatedly used in practice, such that the service life of the catalyst can be improved. The applied catalyst is also characterized in adjustable shell thickness, adjustable catalytic active site number, easy separation, good stability, and the like. Therefore, the method is provided with better practicality and effectiveness.

Description

technical field [0001] The invention belongs to the technical field of preparation of chiral compounds, in particular to a method for one-step separation of racemates to prepare homochiral compounds. Background technique [0002] Pure optical enantiomers have important applications in chiral chemistry, agricultural chemistry, medicinal chemistry and other fields. At present, there are many methods to obtain pure chiral enantiomers, such as: chiral chromatographic separation technology, asymmetric synthesis method, kinetic resolution method and so on. Among them, the dynamic kinetic resolution (DKR) of amines is a relatively difficult subject. This is because the amine itself can be used as a ligand to combine with the active site of the metal, and the C-N bond may also be broken under the catalysis of the transition metal, which makes the hydrodehydrogenation and racemization of the amine difficult to proceed [Eur. J. Org. Chem. 2010, 999–1015], and the required conditions...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P41/00C12P13/00B01J29/035
CPCY02P20/584
Inventor 唐颐史静张亚红
Owner FUDAN UNIV
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