The method of synthesizing theanine

A technology of theanine and glutamic acid, applied in chemical instruments and methods, preparation of organic compounds, preparation of carboxylic acid amides, etc., can solve the problems of affecting the quality of L-theanine, danger to life and environment, and many types of products. , to achieve the effect of low cost, high equipment requirements and high yield

Active Publication Date: 2011-12-28
SICHUAN TONGSHENG AMINO ACID CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004]Method 1, use L-glutamine and ethylamine derivatives to mix and then use glutaminase to convert and synthesize (CN 1977047A), this method can avoid D- The production of theanine, but the process is long, the operation is complicated, there are many types of products, it is not easy to separate, and the equipment requirements are high
[0005] Method 2, using ethylamine and L-pyroglutamic acid to react and synthesize (CN 1706816 A, CN 1690046A). The total yield of this method is higher, but it needs to use Anhydrous ethylamine and pressure equipment are used, which cause high equipment requirements for industrial production, and there is a greater risk to life and the env...

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  • The method of synthesizing theanine
  • The method of synthesizing theanine

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Experimental program
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Effect test

Embodiment 1

[0030] 1. Add ethanol to 1300L in a 1500L stainless steel reaction tank, add L-glutamic acid (HOOCOCH 2 CH 2 CH (NH 2 ) COOH) 300kg (N mol), cool the ice water to 0-5°C, add sulfuric acid 200kg (2N.mol), remove the ice water after the dropwise addition, control the temperature at 8-10°C, and react for 8-10 hours, the reaction formula is as follows :

[0031]

[0032] After the TLC monitoring is qualified, it is neutralized to pH 7.0-7.5 by passing through ethylamine, centrifuged, washed with ethanol until the centrifugate is colorless, and L-glutamic acid-5-ethyl ester (HOOCOCH) containing 20% ​​ethanol is obtained. 2 CH 2 CH (NH 2 ) COOC 2 h 5 )350kg. (Mother liquor can recover ethanol and detect and be used for this step reaction of next batch)

[0033] 2. Add 500L of ethanol to a 1500L stainless steel reverse tank, add 180kg of L-glutamic acid-5-ethyl ester under stirring, and add 70% ethylamine (C 2 h 7 N) 600L of aqueous solution, reacted at 20-25°C for 72 ho...

Embodiment 2

[0038] 1. Add ethanol to 1100L in a 1500L stainless steel reaction tank, add 300kg (N mol) of L-glutamic acid, cool down to 0-5°C with ice water, add 280kg (2N.mol) of sulfuric acid, and remove the ice water after the dropwise addition , control the temperature at 8-10°C, react for 8-10 hours, after TLC monitoring is qualified, pass through ethylamine to neutralize to pH 7.0-7.5, centrifuge, wash with ethanol until the centrifuge is colorless, and obtain 20% ethanol L-glutamic acid-5-ethyl ester 370kg.

[0039] 2. Add 600L of ethanol to a 1500L stainless steel reverse tank, add 175kg of L-glutamic acid-5-ethyl ester under stirring, add about 550L of 70% ethylamine under cooling, and react at 20-25°C for 48 hours until it is basically complete, and recover Excess ethylamine (recovered ethylamine can be used in the next batch of this step reaction) to obtain L-theanine ethylamine solution, recover ethylamine and ethanol, after concentration, add ethanol to precipitate crystals, ...

Embodiment 3

[0042] 1. get aforementioned embodiment one, the mother liquor that centrifuges gained in the second step of two is about 150L of feed liquid after reclaiming the ethanol concentration, add the ethanol 300L that reclaims, add aforementioned embodiment one, the second step that reclaims in two Amine 500L (contains a small amount of ethanol when recovered), reacted at 20-25°C for 48 hours until almost complete, recovered excess ethylamine (recovered ethylamine can be used in the next batch of this step reaction) to obtain L-theanine ethylamine solution of about 750L, after concentration, add ethanol to precipitate crystals, and centrifuge to obtain 80KG crude L-theanine. (The centrifuged mother liquor is to be detected after recovery of ethylamine and ethanol).

[0043] 2. Add 80KG of L-theanine crude product to 280L water, heat up and dissolve, add 1KG activated carbon for decolorization and filtration, add 95% edible ethanol twice (V / V), precipitate crystals, centrifuge to sep...

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Abstract

A method for synthesizing theanine comprises the following steps of: (1) suspending glutamic acid in C1-6 alcohol, performing a catalytic reaction under acidic condition, neutralizing to neutral by the use of an organic base, followed by centrifugation to obtain glutamic acid-5-ester; (2) suspending glutamic acid-5-ester in C1-4 alcohol, adding ethylamine for a reaction to obtain a theanine ethylamine solution; recovering ethylamine and ethanol by the use of the theanine ethylamine solution, followed by pressure reduction, condensation and crystallization, separating and collecting crystals; (3) dissolving the crystals in water, followed by refining and filtering, adding edible alcohol for crystallization, separating and collecting crystals to obtain theanine. High-purity L-theanine and D-theanine can be obtained by the adoption of the synthesis method provided by the invention. The corresponding isomer of the prepared theanine is less than 0.02%. The contents of two structures contained in the obtained high-purity DL-theanine are similar. In addition, the production technology of theanine is simple and short; the whole reaction process is carried out in normal pressure; in comparison with synthesis methods which require pressure, the synthesis method provided by the invention is safer and more environment-friendly to life and environment, is simple in operation, results in high yield, requires low cost, and has no high requirement on equipment.

Description

technical field [0001] The invention relates to a method for synthesizing amino acids, in particular to a method for synthesizing theanine. Background technique [0002] Tea is rich in a variety of amino acids, among which L-theanine (L-thiamine) has edible and health functions and is beneficial to the human body, while free D-theanine has many side effects on the human body. People rely on drinking tea to ingest L-theanine, but the L-theanine contained in tea is very limited, so a method of artificially synthesizing L-theanine was invented in order to obtain more high-purity L-tea amino acid, and claim that it is very low in D-theanine. [0003] At present, there are three main methods for artificially synthesizing L-theanine: [0004] Method 1, using L-glutamine and ethylamine derivatives to mix and then use glutaminase to convert and synthesize (CN 1977047A), this method can avoid the generation of D-theanine, but the process is long, the operation is complicated, and t...

Claims

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Application Information

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IPC IPC(8): C07C237/06C07C231/02
Inventor 伍万兵伍平陈纹锐王东洲
Owner SICHUAN TONGSHENG AMINO ACID CO LTD
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