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Preparation method for selenomethionine

The technology of selenomethionine and methionine is applied in the field of preparation of selenomethionine, which can solve the problems of high equipment requirements and difficult operation, and achieve the effects of simple equipment, improved yield and simple synthesis process.

Active Publication Date: 2016-12-14
SICHUAN SINYIML BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Adopt relatively cheap gamma-butyrolactone as starting material, what obtain is DL-selenomethionine, total yield is about 33%, this synthetic route needs to add highly toxic liquid bromine at the boiling point temperature close to bromine, operation Difficult and requires high equipment

Method used

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  • Preparation method for selenomethionine
  • Preparation method for selenomethionine
  • Preparation method for selenomethionine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] (a) Synthesis of L-α-amino-γ-butyrolactone hydrobromide: in a 50L reactor, add 3.4kgL-methionine, 2.8kg dimethyl carbonate, 12.5kg ethanol (density is 0.998g / cm 3 ) and 12.5kg of water, add 6.12kg of glacial acetic acid (with a density of 1.05g / cm 3 ) and 3.4kg of bromoacetic acid, then heated to 70°C for reflux for 5 hours, distilled under reduced pressure, and then added 6.8kg (density of 1.38g / cm 3 ) 40% hydrobromic acid, heated to 50°C for 2h, cooled to 20°C, cooled to crystallize, filtered to obtain white crystalline solid L-α-amino-γ-butyrolactone hydrobromide (intermediate 1), The yield is 95%;

[0036] (b) Synthesis of sodium methyl selenide: In a 50L reaction kettle, add 20kg of 20% sodium hydroxide solution, then add 4.7kg of selenium powder, 3.8kg of hydrazine hydrate, and stir for 48 hours at 20°C. Then add 5.7kg dimethyl carbonate, stir and react at 20°C for 12h, after the reaction is over, let it stand for stratification, separate the lower organic phase...

Embodiment 2

[0039] (a) Synthesis of L-α-amino-γ-butyrolactone hydrobromide: in a 50L reactor, add 5kgL-methionine, 4kg dimethyl sulfate, 10kg isopropanol (density is 0.998g / cm 3 ) and 10kg of water, add 6.5kg of glacial acetic acid (with a density of 1.05g / cm 3 ) and 3.5kg of bromoacetic acid, then heated to 90°C for reflux reaction for 1h, distilled under reduced pressure, and then added 2kg (with a density of 1.38g / cm 3 ) 40% hydrobromic acid, heated to 70°C for 0.5h, cooled to 25°C, cooled to crystallize, filtered to obtain white crystalline solid L-α-amino-γ-butyrolactone hydrobromide (intermediate 1) , the yield is 92%;

[0040] (b) Synthesis of sodium methyl selenide: In a 50L reaction kettle, add 12kg of 20% sodium hydroxide solution, then add 2.4kg of selenium powder, 2kg of hydrazine hydrate, and stir for 24 hours at 25°C. Then add 3kg of dimethyl sulfate, stir and react at 20°C for 4h, after the reaction is over, let it stand for stratification, separate the lower organic phas...

Embodiment 3

[0043] (a) Synthesis of L-α-amino-γ-butyrolactone hydrobromide: in a 100L reactor, add 15kgL-methionine, 12kg dimethyl carbonate, 15kg isopropanol (density is 0.998g / cm 3 ) and 15kg of water, add 28.8kg of glacial acetic acid (with a density of 1.05g / cm 3 ) and 16kg of bromoacetic acid, then heated to 80°C for reflux for 3h, distilled under reduced pressure, and then added 30kg (with a density of 1.38g / cm 3 ) 40% hydrobromic acid, heated to 60°C for 1.5h, cooled to 25°C, cooled to crystallize, filtered to obtain white crystalline solid L-α-amino-γ-butyrolactone hydrobromide (intermediate 1) , the yield is 90%;

[0044] (b) Synthesis of sodium methyl selenide: In a 100L reaction kettle, add 20kg of 20% sodium hydroxide solution, then add 4.8kg of selenium powder, 4kg of hydrazine hydrate, and stir for 26 hours at 23°C. Then add 6kg of dimethyl sulfate, stir and react at 23°C for 10h, after the reaction is over, let it stand for stratification, separate the lower organic phase...

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Abstract

The invention discloses a preparation method for selenomethionine, which includes the steps of: (a) performing a reaction to L-methionine and dimethyl carbonate to remove a methylthio group and meanwhile form a ring to generate L-[alpha]-amino-[gamma]-butyrolactone, and adding hydrobromic acid to carry out a reaction to obtain L-[alpha]-amino-[gamma]-butyrolactone hydrobromate; (b) performing a reaction to selenium with hydrazine hydrate to generate sodium diselenide, adding a methylation reagent, dimethyl carbonate, to carry out a reaction to generate dimethyl diselenide, and reducing the dimethyl diselenide with sodium borohydride to obtain sodium methylselenide; and (c) performing a heating reflux reaction to the L-[alpha]-amino-[gamma]-butyrolactone hydrobromate and sodium methyl selenol to obtain L-selenomethionine sodium salt, and regulating the pH of the reaction liquid to 5-6 with acetic acid, and dehydrating the reaction liquid to obtain the target product L-selenomethionine. The preparation method has high product yield and simple synthetic process, is prepared from easy-to-obtain raw materials, has mild reaction conditions and is easy to carry out industrially.

Description

technical field [0001] The invention belongs to the field of feed additives for poultry and livestock, and in particular relates to a preparation method of selenomethionine. Background technique [0002] As a feed additive for poultry and livestock, organic selenium has the characteristics of improving the quality of poultry and livestock products, enhancing animal reproductive ability, improving its immunity, high absorption rate, and strong biological activity, so it has become one of the hot spots in selenium research. [0003] At present, the common methods for synthesizing L-selenomethionine include liquid ammonia method, methyl lithium method, aminobutyrolactone hydrobromide method, methylselenopropionaldehyde method, dihaloethylpiperidinedione method, etc. The latest synthesis process of selenomethionine in the world is developed by T.Koch and O.Buchardt, and its synthesis process is shown in the following formula: [0004] [0005] The synthesis method starts fro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C391/00
CPCC07C391/00C07D307/33
Inventor 陈明剑张伟李俊虎刘棚
Owner SICHUAN SINYIML BIOTECH CO LTD
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