Modified synthesis method for L-theanine

A synthesis method and technology of theanine, applied in chemical instruments and methods, preparation of aminohydroxy compounds, preparation of carboxylic acid amides, etc., can solve the problems of side reaction products, deterioration of color, and reduction of yield, etc., to avoid oxidation The effect of reaction, convenient operation and short process

Inactive Publication Date: 2007-12-12
NANJING RALLY BIOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] During the experiment and pilot test of L-theanine, we found that the presence of oxygen in the air would cause side reactions in the amination reaction or oxidize the product, resulting in poor color. In order to make the produ

Method used

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  • Modified synthesis method for L-theanine
  • Modified synthesis method for L-theanine
  • Modified synthesis method for L-theanine

Examples

Experimental program
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Effect test

Embodiment 1

[0030] In a 500L stainless steel autoclave, add 60Kg of L-pyrrolidone acid and 0.6Kg of ethoxyquinoline, seal the autoclave, add 200Kg of liquid anhydrous ethylamine, heat slowly with a hot water bath, and keep the internal temperature at 30-59°C. Stir at a medium speed, keep the pressure at 0.4-5.9MPa, react for 48 hours, and when the reaction is over, recover excess ethylamine, which can be reused for feeding. The reaction product was decolorized with activated carbon and recrystallized from 95% ethanol to obtain 47.3Kg of refined product, yield: 58.5%, [α] 20 D +7.7~+8.5°(5%, H 2 O), purity: (HPLC) ≥ 98.5%.

Embodiment 2

[0032] In a 500L stainless steel autoclave, add 60Kg of L-pyrrolidone acid to a closed reaction autoclave, exhaust the air in the autoclave with dry ethylamine gas in the steel cylinder, then add 190Kg of liquid anhydrous ethylamine, slowly heat with a hot water bath, Keep the temperature at 30-59°C, stir at a medium speed, and keep the pressure at 0.4-5.9MPa. React for 60 hours. After the reaction is over, recover excess ethylamine, which can be reused for feeding. The reaction product was decolorized with activated carbon, recrystallized with 95% ethanol, and soaked in absolute ethanol to obtain a fine product of 38.9Kg, yield: 48.2%, [α] 20 D +7.7~+8.5°(5%, H 2 O), purity: (HPLC) ≥ 98.5%.

Embodiment 3

[0034] In a 1000L stainless steel autoclave, add 60Kg L-pyrrolidone acid and 0.6g quinoline as an antioxidant, seal the autoclave, exhaust the air in the autoclave with the dry gas in the steel cylinder, then add 380Kg of liquid anhydrous ethylamine, heat Slowly heat the water bath, keep the internal temperature at 30-59°C, stir at a medium speed, keep the pressure at 0.4-5.9MPa, react for 48 hours, the reaction crystallizes, recover excess ethylamine, and the recovered ethylamine can be fed repeatedly and used mechanically. The reaction product was decolorized with activated carbon, recrystallized from 95% ethanol, and 97.2Kg of fine product was obtained, yield: 60.1%, [α] 20 D +7.8~+8.5°(5%, H 2 O), purity: (HPLC) ≥ 98.5%.

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Abstract

The invention relates to a method for synthesizing L- theanine. It takes L- pyrrolidone acid and waterless ethlamine as raw material, carrying out reaction under anti- oxidizing agent existence and with air discharged by dried ethlamine gas condition. The reaction temperature is 30- 59 Deg. C, the pressure is 0.4- 5.9 Mpa, and the productivity is apparently higher than that of under condition without anti- oxidizing agent and with air.

Description

field of invention [0001] The invention relates to the fields of organic chemistry and medicinal chemistry, in particular, the invention relates to an improved synthesis method of L-theanine, a characteristic amino acid of tea. Background technique [0002] L-theanine (L-theanine) is a characteristic amino acid that exists in tea leaves in nature and is all L-type. The chemical name is: N-ethyl-L-glutamine (N-ethyl-L-glutamine), American Chemical Abstract registration number CAS: [3081-61-6], the pure product is white needle crystal, melting point: 217-218°C (decomposition), specific rotation: [α] 20 D : +7.7-+8.5°(5%, H 2 O). [0003] Its structural formula is as follows: [0004] [0005] Because the L-theanine contained in the tea leaves is only 2%, it is very difficult to obtain and mass-produce the high-purity L-theanine from the tea leaves. In order to meet the needs of the market, it is economically meaningful to prepare L-theanine by chemical synthesis. [0...

Claims

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Application Information

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IPC IPC(8): C07C229/26C07C213/00
CPCC07C231/14
Inventor 陈新王凯文
Owner NANJING RALLY BIOCHEM
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