Methionine hydroxyl analogue isopropyl ester compound as well as preparation method and production system thereof

Abstract

The invention relates to the technical field of organic synthesis preparation, in particular to a methionine hydroxyl analogue isopropyl ester compound and a preparation method and a production system thereof. The methionine hydroxyl analogue isopropyl ester compound is a compound of methionine hydroxyl analogue isopropyl ester, methionine hydroxyl analogue dimer isopropyl ester, methionine hydroxyl analogue trimer isopropyl ester, methionine hydroxyl analogue calcium salt and calcium phosphate, and is in a solid powder shape. According to the preparation method disclosed by the invention, phosphoric acid, calcium hydrogen phosphate or monocalcium phosphate and a composition thereof are used as an esterification catalyst, a calcium compound is used for neutralization, and then direct concentration is performed, so that the step that the catalyst needs to be separated from a reaction solution is omitted, and the methionine hydroxyl analogue isopropyl ester product does not need to be washed, rectified and purified; the product purification energy consumption and the residual liquid incineration treatment process are saved, and the utilization rate of the methionine source is improved. The solid powdery methionine hydroxyl analogue isopropyl ester compound disclosed by the invention has the advantages of high stability and high rumen bypass rate of ruminants.

Description

technical field [0001] The invention relates to the technical field of organic synthesis preparation, in particular to a methionine hydroxyl analog isopropyl ester compound and a preparation method and production system thereof. Background technique [0002] The methionine hydroxy analog is an intermediate in the metabolism of methionine. Since it does not contain amino groups, deamination does not occur in the metabolism. When methionine is metabolized in the body, it will use the free ammonia in the rumen and blood to increase the nitrogen deposition in the body. The efficiency of nitrogen use is improved, the excretion of nitrogen is reduced, and the pollution to the environment is reduced. Although methionine hydroxy analogs can promote fiber degradation and acetic acid growth, they are easily degraded by microorganisms in vivo, and have short residence time and low utilization in vivo, so it is necessary to protect them. The protection of methionine hydroxy analogs mai...

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Problems solved by technology

In the recovery process of the by-product stream or the heavy recycle stream mentioned in the examples, the reaction and catalyst recovery steps still need to be carried out again, which is not conducive to continuous industrial production

[0006] U.S. Patent No. 3,761,518 and U.S. No. 3,850,987 disclose that under the catalysis of hydrogen chloride, D, L-2-hydroxyl-4-methylthiobutyrate (calcium salt, sodium salt, potassium salt, ammonium salt, etc.) , ethanol, isopropanol, butanol, etc.) to prepare high-purity D,L-2-hydroxy-4-methylthiobutyrate technical scheme; the process operation is complicated, especially the raw material D,L-2- Preparation of hydroxy-4-methylthiobutyrate, that is, D,L-2-hydroxy-4-methylthiobutyronitrile is hydrolyzed with sulfuric acid, neutralized with ammonia, and desalted to obtain 88% of D,L-2- Aqueous solution of monomer, dimer and multimer of hydroxy-4-methylthiobutyric acid, wherein monomer content is 65%, dimer and multimer content is 23%, water content is 12%, in order to obtain Monomer D,L-2-hydroxy-4-methylthiobutyric acid needs to be hydrolyzed by adding alkali to obtain D,L-2-hydroxy-4-methylthiobutyrate, while D,L- Under the action of hydrogen chloride, 2-hydroxy-4-methylthiobutyrate will be converted into D,L-2-hydroxy-4-methylthiobutyric acid, D,L-2-hydroxy-4-methylthio The butyric acid part is polymerized again to form dimers and polymers, which will lead to low purity of the product and low esterification rate of D, L-2-hydroxy-4-methylthiobutyric acid, D, L -2-Hydroxy-4-methylthiobutyrate in low yield

[0007] According to the existing technical analysis, there are the following problems: No matter which method is adopted in the above method, the final product obtained is a high-purity D,L-2-hydroxy-4-methylthiobutyrate monomer, which is viscous brown yellow liquid

In order to obtain high-purity monomers, it is unavoidable to produce a large amount of acid-containing and salt-containing wastewater, and because the dimer and multimer esterification reactivity of methionine hydroxyl analogs are low, even if they can be esterified, the obtained ester Due to the large molecular weight (greater than 300), the esterification products of dimers and multimers have high boiling points, which cannot be obtained by rectification. Finally, the esterification products of dimers and multimers are kept in rectification In the raffinate, the final treatment can only be incineration; moreover, the raffinate after the esterification of the monomeric methionine hydroxy analogs after rectification contains not only the esterification products of dimers and polymers, but also the catalyst inorganic acid , for the treatment of inorganic acid liquid, it is mainly recycled to the esterification reaction of the next batch of methionine hydroxyl analogues, or after neutralization with alkali, it is evaporated and concentrated, but no matter what the method is, the biggest problem in the end is: monomer methionine The yield of hydroxy analog ester is low, the processing energy consumption of product and raffinate is high, and the material loss is large, while the dimer and multimer in the raffinate, even unreacted methionine hydroxy analog monomer, etc. are animals that can Digested and absorbed high-quality methionine source, incineration treatment not only causes waste of resources, but also causes environmental pollution, producing a large amount of carbon emissions and sulfur oxides

[0009] The organic combination of methionine hydroxyl analogue isopropyl ester, liquid methionine calcium salt and calcium phosphate salt not only supplements high-quality methionine source for ruminants, increases the passage of methionine through the rumen, but also supplements high-quality organic calcium and phosphorus for animals , there are few reports on

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