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Synthesis process of (R)-3-hydroxybutyric acid and salts thereof

A technology of hydroxybutyric acid and hydroxybutyrate, applied in the synthesis process of magnesium salt, calcium salt, potassium salt, -3-hydroxybutyric acid and its sodium salt field, can solve the problem of large production input and enantiomeric excess value. Low cost, complex process and other problems, to achieve the effect of convenient post-processing, low cost and little environmental pollution

Inactive Publication Date: 2017-09-15
洛阳华荣生物技术有限公司
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  • Abstract
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  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented process produces certain chemicals that are very effective for use in various industries such as food production or medicine manufacturing processes. These compounds can be used with minimal amounts of harmful substances during their preparation. They also provide technical benefits over existing methods due to lower costs associated with them compared to other alternatives.

Problems solved by technology

This patented technical problem addressed in this patents relates to finding ways to improve chemosynthesis processes for producing specific types of molecules called beta -substances such as gamma amino acids, which serve different roles within biology like cardiovascular systems, muscle cells, bacterium cell walls, and other organs. These substituents include α-,β-unsaturated alkaloids, sterols, and certain organics. Previous attempts at making them were expensive because they require multiple steps involving complicated reaction techniques.

Method used

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  • Synthesis process of (R)-3-hydroxybutyric acid and salts thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1: synthetic (R)-3-hydroxybutyric acid methyl ester

[0037] Dichlorophenylruthenium(II) dimer [RuCl 2 (benzene) 2 ](80mg, 160umol), (R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-dibenzofuranyl-8,8'-dipotassium disulfonate Salt ligand (340umol) and methyl 3-oxobutanoate (74ml, 680mmol) were dissolved in methanol (600ml). After degassing under reduced pressure and purging the autoclave with nitrogen, the hydrogenation reaction was carried out at 60° C. and a hydrogen pressure of 10 bar for 16 hours. Cool to room temperature and concentrate to near dryness to obtain a mixture of catalyst and methyl (R)-3-hydroxybutyrate. Slowly heat up to 80°C and distill under reduced pressure to obtain colorless methyl (R)-3-hydroxybutyrate (76.0 g) with a yield of 94.7% and an ee value of 94%. The catalyst is recovered and can be reused after regeneration. The concentrated and recovered methanol can be directly reused.

[0038] MS:119(M+H)

Embodiment 2

[0039] Embodiment 2: synthetic (R)-3-hydroxybutyrate ethyl ester

[0040] Dichlorophenylruthenium(II) dimer [RuCl 2 (benzene) 2 ](80mg, 160umol), (R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-dibenzofuranyl-8,8'-dipotassium disulfonate Salt ligand (340umol) and ethyl 3-oxobutanoate (86ml, 680mmol) were dissolved in methanol (600ml). After degassing under reduced pressure and purging the autoclave with nitrogen, the hydrogenation reaction was carried out at 80° C. and a hydrogen pressure of 10 bar for 20 hours. Cool to room temperature and concentrate to near dryness to obtain a mixture of catalyst and ethyl (R)-3-hydroxybutyrate; slowly warm up to 85°C and distill under reduced pressure to obtain colorless ethyl (R)-3-hydroxybutyrate 88.4 g, yield 98.5%, ee value 94.5%. The catalyst is recovered and can be reused after regeneration. The methanol recovered by concentration can be used directly.

[0041] MS:133(M+H)

Embodiment 3

[0042] Embodiment 3: preparation (R)-3-hydroxybutyrate sodium

[0043] In a 500ml three-necked flask, add the (R)-3-hydroxybutyrate methyl ester (76.0g) obtained in Example 1, add 300ml of water, control the temperature to less than 30°C, and slowly add the hydroxide in batches within 3 hours Sodium (25.8g), control the temperature not higher than 10°C, continue to react for 3 hours until the reaction is complete. Add 0.3 g of activated carbon, continue to stir for 0.5 hours, filter, and concentrate the filtrate to 100 ml. At this time, a large amount of solids precipitate out, cool down to room temperature, stir and crystallize for 1 hour, centrifuge, and dry in vacuo to obtain white solid (R)-3-hydroxybutyrate Sodium acid 68.9g, yield 85.0%, ee value 91.5%.

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Abstract

The invention discloses a synthesis process for preparing (R)-3-hydroxybutyric acid and sodium salt, potassium salt, magnesium salt and calcium salt thereof. The process includes steps: adding 3-oxobutanoate and a ruthenium complex catalyst into organic solvent according to a mole ratio of 1:0.0005-0.005, and reacting at 20-80 DEG C for 12-24h under a hydrogen pressure of 1-20bar to obtain (R)-3-hydroxybutyrate; dissolving (R)-3-hydroxybutyrate into water, and subjecting to reaction with sodium hydroxide, potassium hydroxide or calcium hydroxide for 2-12h at a low temperature to obtain sodium salt, potassium salt, magnesium salt and calcium salt of (R)-3-hydroxybutyric acid; subjecting water solution of (R)-3-sodium hydroxybutyrate to 732 cation exchange resin treatment to remove sodium ions to obtain (R)-3-hydroxybutyric acid; subjecting (R)-3-hydroxybutyric acid to reaction with magnesium hydroxide to obtain (R)-3-magnesium hydroxybutyrate. Ee values of (R)-3-hydroxybutyric acid and sodium salt, potassium salt, magnesium salt and calcium salt thereof reach 90% or above. The method has advantages of low environment pollution, low cost and easiness in aftertreatment.

Description

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Claims

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Application Information

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Owner 洛阳华荣生物技术有限公司
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