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Method for synthesizing theanine

A synthesis method, theanine technology, applied in chemical instruments and methods, preparation of carboxylic acid amides, preparation of organic compounds, etc., can solve problems such as poor selectivity, slow reaction speed, and low yield

Inactive Publication Date: 2006-06-21
天津金耀氨基酸有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These synthetic methods have shortcomings such as high production cost, slow reaction speed, poor selectivity, and low yield to varying degrees; using the above-mentioned methods, a small amount of D-type product will be produced in the synthetic process, which cannot be removed by chemical methods, which affects product quality.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0074] Weigh in a 1000ml three-necked bottle, add 60g of L-glutamic acid, 600ml of absolute ethanol, cool to 10°C under stirring, add 30ml of concentrated sulfuric acid dropwise, after the dropwise reaction at room temperature for 8 hours, add dropwise Triethylamine was neutralized, filtered after cooling, and the filter cake was dried to obtain 50 grams of L-glutamic acid-γ-ethyl ester with a yield of 70%.

[0075] In a 1000ml three-necked flask, add 40g of L-glutamic acid-γ-ethyl ester, add 600ml of ethanol aqueous solution, add 60g of sodium bicarbonate, dissolve and cool to 10°C, add 40ml of acetic anhydride dropwise, and dropwise Afterwards, react at room temperature for 3 hours, concentrate and desalinate to obtain L-N-acetyltheanine solution, add 300 ml of 70% ethylamine aqueous solution, stir the reaction until the ammoniation reaction is complete, and obtain L-N-acetyltheanine solution.

[0076] The L-N-acetyltheanine solution is concentrated, check the solution to ne...

example 2

[0078] Example 1 Weigh in a 1000ml three-neck flask, add 60g of L-glutamic acid and 500ml of n-butanol, cool to below 10°C under stirring, add 30ml of concentrated sulfuric acid dropwise, and react at room temperature for 12 hours , dropwise added triethylamine to neutrality, filtered after cooling, and dried the filter cake to obtain 66.6 g of L-glutamic acid-γ-n-butyl ester with a yield of 80%.

[0079] In a 1000 ml three-necked flask, add 40 g of L-glutamic acid-γ-n-butyl ester, add 400 ml of ethanol aqueous solution, add 50 g of sodium bicarbonate, dissolve and cool below 10°C, add dropwise 50 ml of acetic anhydride, After dropping, react at room temperature for 2 hours, concentrate and desalt to obtain L-N-acetylglutamic acid-γ-n-butyl ester solution, add 400 ml of 70% ethylamine aqueous solution, stir and react until the ammoniation reaction is complete, and obtain L-N-acetylglutamate acid solution.

[0080] The L-N-acetyltheanine solution is concentrated, check the sol...

example 3

[0082] In a 1000 ml three-necked flask, add 60 grams of L-glutamic acid and 600 ml of absolute ethanol, cool to 10°C under stirring, add 30 ml of concentrated sulfuric acid dropwise, and react at room temperature for 8 hours, add triethyl ether dropwise The amine was neutralized, filtered after cooling, and the filter cake was dried to obtain 50 g of L-glutamic acid-γ-ethyl ester with a yield of 70%.

[0083] In a 1000ml three-neck flask, add 40g of L-glutamic acid-γ-ethyl ester, add 200ml of water, add 40g of sodium bicarbonate, dissolve and cool to 10°C, add 15ml of benzoyl chloride dropwise, and dropwise Afterwards, react at room temperature for 2 hours, concentrate and desalinate to obtain L-N-benzoylglutamate-γ-ethyl ester solution, add 400 ml of 70% ethylamine aqueous solution, stir the reaction until the ammoniation reaction is complete, and obtain L-N-benzoylglutamic acid-γ-ethyl ester solution. Theanine solution.

[0084] The L-N-benzoyltheanine solution is concentra...

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Abstract

The invention relates to a method for synthesizing theanine, which consists of ammonifying the L-N-acyl aminoglutaric acid-ª†-ester with aminoethane solution of 70% and getting L-N-acyl theanine, hydrolyzing with L-aminoacylase, and only L-N-acyl theanine is hydrolyzed to remove the acyl, and evoluting in alcohol solution to get the L-theanine of high quality. The invention combines the dominance of already industrialized L-aminoacylase hydrolyzing acyl, employing cheap acyl as protective group and reacting with aminoethane solution, then hydrolyzing acyl with L-aminoacylase to get L-theanine. The invention is characterized by the cheap raw material, low production cost, high selectivity, fast reaction speed and high productivity. The raw material and agent is suited for industrial production, the operation process is simple and the product quality can be guaranteed.

Description

technical field [0001] The present invention relates to the synthetic method of theanine. Background technique [0002] Theanine (L-Theanine) is a unique amino acid in tea, accounting for 50% of amino acids, and its structural formula is: CH 3 CH 2 NHCOCH 2 CH 2 CH(NH 2 )COOH. It is the most important taste substance in tea. Theanine is a safe, non-toxic, natural food additive with multiple physiological functions. In foreign countries, it has been widely used in food such as beverages, baked snacks, frozen snacks, etc., but the application of theanine in the food field in China is still blank. Japan approved L-theanine as a food additive in 1964, and the US FDA confirmed L-theanine as a generally recognized safe substance in 1985. Recent animal and human experiments have shown (Ling Guanting, L-theanine and its physiological functions, food and oils. 2003.5, 46-49): L-theanine is a safe, effective, and no side effects of stimulation accelerator , is an excellent su...

Claims

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Application Information

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IPC IPC(8): C07C231/02C07C237/06
CPCY02P20/55
Inventor 朱廷哲张金荣侯庆林
Owner 天津金耀氨基酸有限公司
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