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Synthesis and purification method for alpha-amino acid compound

An amino acid and purification method technology, which is applied in the field of synthesis and purification of α-amino acid compounds, can solve problems such as difficulty in separation, and achieve the effects of high purity, recycling and simple method.

Active Publication Date: 2015-09-09
HEBEI VEYONG BIO CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This process not only uses a large amount of acid and alkali, and forms a large amount of waste salt after neutralization, but also is not applicable to all amino acids, such as amino acids with high water solubility, and it is difficult to separate high-purity products after post-treatment.

Method used

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  • Synthesis and purification method for alpha-amino acid compound
  • Synthesis and purification method for alpha-amino acid compound
  • Synthesis and purification method for alpha-amino acid compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment example 1

[0061] Example 1: Synthesis of 2-amino-4-methylthiobutyric acid

[0062] Add 130g (1mol) of 2-amino-4-methylthiobutyronitrile into a 1L autoclave, add 68g of 25% ammonia water and 56g (1mol) of calcium oxide, 2g of tetrabutylammonium bisulfate, 500g of water, and heat to 180-190 o C, pressure 2.5-3.0MPa, react for 5h, cool down to room temperature, pass carbon dioxide under stirring until pH = 8, filter, concentrate the mother liquor under reduced pressure, add 150g methanol to the residue and reflux for 2h, cool down, and crystals precipitate out. Filtration, vacuum 120 o C dried for 4 hours to obtain 118.3 g of 2-amino-4-methylthiobutyric acid with a purity of 96% and a yield of 79.4%.

Embodiment example 2

[0063] Example 2: Synthesis of 2-amino-3-(4-imidazolyl)propionic acid

[0064] Add 180g (1mol) of 5-[(4-imidazolyl)methyl]hydantoin to a 1L autoclave, add 68g of 25% ammonia water and 110g (1.5mol) of calcium hydroxide, 500g of water, and heat to 160-170 o C, pressure 1.5~2.0MPa, react for 8h, cool down to room temperature, pass carbon dioxide under stirring until pH=8, filter, concentrate the mother liquor under reduced pressure, add 150g methanol to the residue and reflux for 2h, cool down, and crystals precipitate out. Filtration, vacuum 120 o C dried for 4 hours to obtain 124.2 g of 2-amino-3-(4-imidazolyl)propionic acid with a purity of 96% and a yield of 80.1%.

Embodiment example 3

[0065] Example 3: Synthesis of 2-amino-3-(4-imidazolyl)propionic acid

[0066] Add 180g (1mol) of 5-[(4-imidazolyl)methyl]hydantoin to a 1L autoclave, add 68g of 25% ammonia water and 110g (1.5mol) of calcium hydroxide, 3g of triethylbenzyl ammonium sulfate, and 500g of water , heated to 160-170 o C, pressure 1.5~2.0MPa, react for 3h, cool down to room temperature, pass carbon dioxide to pH=8, filter, concentrate the mother liquor under reduced pressure, add 150g methanol to the residue and reflux for 2h, cool down, and crystals precipitate out. Filtration, vacuum 120 o C dried for 4 hours to obtain 134.5 g of 2-amino-3-(4-imidazolyl)propionic acid with a purity of 96% and a yield of 86.8%.

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Abstract

The invention relates to a synthesis and purification method for an alpha-amino acid compound. The synthesis and purification method is characterized by comprising the following steps: (1) adding substituted alpha-amino nitrile or a substituted hydantoin-based compound into alkali M(OH)x or metal oxide MxO, adding water or an alcohol and water mixed solvent, and heating for reaction to obtain alpha-amino acid salt; (2) adding ammonium carbonate or ammonium bicarbonate or introducing carbon dioxide into the solution in the step (1), separating to obtain filter liquor and precipitates MxHyCO3, performing reduced pressure concentration on the filter liquor, and recrystallizing in an alcohol solvent to obtain the alpha-amino acid compound (I). The synthesis and purification method for the alpha-amino acid compound is simple, the yield and purity of the obtained alpha-amino acid compound are high; furthermore, recycling utilization and cleaning production of materials can be realized; the synthesis and purification method is especially suitable for synthesis of the alpha-amino acid compound with high water solubility.

Description

technical field [0001] The invention relates to a method for synthesizing and purifying α-amino acid compounds. Background technique [0002] Amino acid is the basic unit of biological functional macromolecular protein, and the basic substance that constitutes the protein required for animal nutrition. Carboxylic acids with an amino group attached to the α-carbon are α-amino acids. α-amino acid compounds are widely used in food, medicine, pesticide, daily chemical and other industries. At present, the main synthesis methods of amino acids mainly include microbial fermentation, chemical synthesis and enzymatic method. Among them, chemical synthesis methods mainly include: [0003] a) Method for introducing amino and carboxyl groups [0004] (1) Strecker method [0005] [0006] Add ammonia or ammonium salt to the aldehyde for cyanation reaction, add acid or alkali to hydrolyze the generated intermediate to synthesize α-amino acid. Ammonia and hydrocyanic acid can be ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/64C07C323/58C07C319/20C07C229/22C07C227/16C07F9/30
CPCC07C227/16C07C229/22C07C319/20C07C323/58C07D233/64C07F9/301
Inventor 贾成国王双珠史秀肖马彩霞范立攀张银霄杨达
Owner HEBEI VEYONG BIO CHEM
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