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Clean synthesis process of alpha-amino acid compounds

A technology of amino acid and synthesis process, which is applied in the preparation of organic compounds, compounds of group 5/15 elements of the periodic table, cyanide reaction preparation, etc. It can solve problems such as difficult separation and achieve good purity and high yield , the effect of very little amount of three wastes

Inactive Publication Date: 2015-11-11
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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  • Clean synthesis process of alpha-amino acid compounds
  • Clean synthesis process of alpha-amino acid compounds
  • Clean synthesis process of alpha-amino acid compounds

Examples

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Effect test

Embodiment example 2

[0046] Example 2: Synthesis of 2-amino-3-(4-imidazolyl)propionic acid

[0047] Add 90g (0.5mol) of 5-[(4-imidazolyl)methyl]hydantoin into a 1L autoclave, add 240g (2.5mol) of ammonium carbonate, 300g of water, and heat to 150-170 o C, pressure 5~8MPa, react for 5h, distill out ammonium carbonate at normal pressure, then distill out water under reduced pressure, add 150g methanol to the residue and reflux for 2h, cool down, and crystals are precipitated. Filtration, vacuum 120 o C dried for 4 hours to obtain 62.0 g of 2-amino-3-(4-imidazolyl)propionic acid with a purity of 96% and a yield of 80.0%.

Embodiment example 3

[0048] Example 3: Synthesis of 2-amino-3-(4-imidazolyl)propionic acid

[0049] Add 90g (0.5mol) of 5-[(4-imidazolyl)methyl]hydantoin to a 1L autoclave, add 197.5g (3mol) of ammonium bicarbonate, 170g (2mol) of 20% ammonia solution, triethylbenzyl chloride Ammonium chloride 3g, water 200g, heated to 150-170 oC, pressure 5~7MPa, react for 4 hours, distill ammonium bicarbonate and ammonia water under normal pressure, add 150g methanol to the residue and reflux for 2 hours, cool down, and crystals are precipitated. Filtration, vacuum 120 o C dried for 4 hours to obtain 62.7 g of 2-amino-3-(4-imidazolyl)propionic acid with a purity of 97% and a yield of 80.9%.

Embodiment example 4

[0050] Example 4: Synthesis of 2-amino-3-(4-imidazolyl)propionic acid

[0051] Add 90g (0.5mol) of 5-[(4-imidazolyl)methyl]hydantoin into a 1L autoclave, add 255g of 20% ammonia water (3mol), 3g of triethylbenzyl ammonium chloride, and 300g of water, and heat to 150- 170 o C, pressure 5~8MPa, react for 4h, drop to room temperature, concentrate the mother liquor under reduced pressure, add the residue to 150g ethanol and reflux for 2h, cool down, and crystals precipitate out. Filtration, vacuum 120 o C dried for 4 hours to obtain 53.5 g of 2-amino-3-(4-imidazolyl)propionic acid with a purity of 96% and a yield of 69.0%.

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Abstract

The invention relates to a clean synthesis process of alpha-amino acid compounds. The process specifically comprises the following steps of (1) adding one, two, or more of ammonia water / carbon dioxide, ammonium carbonate and ammonium bicarbonate into substituted alpha-amino nitrile or substituted hydantoin-based compounds in water or an alcohol-water mixture solvent, and carrying out heating for conducting a reaction; and (2) distilling the liquid to recover residual ammonium carbonate, ammonium bicarbonate or ammonia water after the reaction is finished, and enabling the distillation residue to crystallize in the alcohol solvent to obtain the alpha-amino acid compounds. The process provided by the invention is simple in operation, realizes recycling of materials, produces an extremely small amount of the three wastes, and is a truly clean process that should be vigorously promoted. The prepared alpha-amino acid compounds are high in yield and good in purity. The process is universally applicable to synthesis of multiple alpha-amino acid compounds.

Description

technical field [0001] The invention relates to a clean synthesis process of α-amino acid compounds. Background technique [0002] The carboxylic acid connected to the amino group on the α-carbon is called α-amino acid, and α-amino acid is the basic unit of biological functional macromolecular protein, and is the basic substance that constitutes the protein required for animal nutrition. 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 enzyme-catalyzed synthesis. [0003] The most important chemical synthesis method of α-amino acid compounds is the aminonitrile method or hydantoin method (respectively, reaction formulas 4 and 5) from aldehydes and ketones as starting materials, and the hydrolysis of aminonitrile or hydantoin to obtain α-amino acids. The hydrolysis of aminonitrile or hydantoin is usually...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B41/08C07C323/58C07C319/20C07D233/64C07C229/22C07C227/24C07F9/38C07C229/48
Inventor 贾成国史秀肖范立攀王双珠韩扶军李瑞范丽芳杨达张银霄
Owner HEBEI VEYONG BIO CHEM
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