A kind of processing method of s-(-)-lipoic acid recycling

A treatment method, lipoic acid technology, applied in chemical instruments and methods, carboxylate preparation, carboxylic acid halide preparation, etc., can solve the problem that S-6,8-dichlorooctanoic acid cannot be reused, S-(-) - Lipoic acid recovery and utilization is difficult, industrial mass production is difficult to repeat, etc., to achieve the effect of low process operation cost, good recycling effect, simple equipment and reagents

Active Publication Date: 2022-03-22
TECHNO (FUJIAN) FOOD INGREDIENTS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are shortcomings such as low product purity and difficulty in repeating industrial mass production.
[0005] 2. After hydrolysis with ethyl 6,8-dichlorooctanoate, 6,8-dichlorooctanoic acid was separated by S-phenethylamine to obtain R-6,8-dichlorooctanoic acid with higher purity, but the other half of S -6,8-Dichlorooctanoic acid cannot be reused
[0006] 3. Using α-lipoic acid as the raw material, using toluene as the solvent, and selecting chiral amines for resolution, the yield and purity are ideal, but after the separation is completed, the other half of the S-(-)-sulfur remains in the mother liquor It is more difficult to recycle octanoic acid
In the prior art, a part of S-(-)-lipoic acid is racemized under conditions of high temperature, high pressure and nitrogen protection, but the process conditions are harsh and easily lead to the polymerization of lipoic acid

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The processing method of a kind of S-(-)-lipoic acid recycling of the present embodiment, its steps are as follows:

[0024] (1) Dissolve 20.6g S-(-)-lipoic acid in 100mL ethyl acetate, then add 6.7g concentration of 30% KOH aqueous solution, stir and react at 45°C for 8h to obtain S-(-)- Lipoic acid reaction solution;

[0025] (2) Pass the above-mentioned S-(-)-lipoic acid reaction solution into an aeration device (aeration can be air, low-concentration oxygen), and aerate for 4 hours; then cool to 0°C, and add dropwise a concentration of 5% Sulfuric acid was added to a pH value of 4 to obtain a yellow paste;

[0026] (3) Dissolve the above yellow paste in toluene, add 7.8g of thionyl chloride dropwise, react at 60°C for 4h; then cool to 10°C, add 12mL of ethanol dropwise and continue to react for 3h to obtain 20.0g of 6, 8-Dichlorooctanoic acid ethyl ester.

[0027] In this example, the yield of ethyl 6,8-dichlorooctanoate was 83%.

Embodiment 2

[0029] The processing method of a kind of S-(-)-lipoic acid recycling of the present embodiment, its steps are as follows:

[0030] (1) Dissolve 20.6g S-(-)-lipoic acid in 100mL toluene, then add 8g concentration of 20% NaOH aqueous solution, stir and react at 50°C for 6h to obtain S-(-)-lipoic acid reaction solution;

[0031] (2) Pass the above-mentioned S-(-)-lipoic acid reaction solution into an aeration device (aeration can be air, low concentration oxygen), and aerate for 2 hours; hydrochloric acid until the pH value of the solution is 2 to obtain a yellow paste;

[0032] (3) Dissolve the above yellow paste in toluene, add 11.7g of thionyl chloride dropwise, react at 60°C for 3h; then cool to 5°C, add 20mL of ethanol dropwise and continue to react for 6h to obtain 21.5g of 6, 8-Dichlorooctanoic acid ethyl ester.

Embodiment 6

[0033] In this example, the yield of ethyl 6,8-dichlorooctanoate was 89%.

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PUM

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Abstract

The invention discloses a processing method for recycling S-(-)-lipoic acid, which comprises the following steps: (1) dissolving S-(-)-lipoic acid in an organic solvent, and then adding alkali for alkalization treatment, Obtain S-(-)-lipoic acid reaction solution; (2) carry out aeration treatment with described S-(-)-lipoic acid reaction solution, then carry out acidification treatment to obtain yellow paste; (3) described yellow The paste is dissolved in an organic solvent, and after adding thionyl chloride for chlorination reaction, adding ethanol to continue the esterification reaction to obtain ethyl 6,8-dichlorooctanoate. The present invention realizes the recycling of S-(-)-lipoic acid, obtains the raw material 6,8 dichlorooctanoic acid ethyl ester for the synthesis of α-lipoic acid, not only solves the recycling problem of S-(-)-lipoic acid, Material waste is avoided, and the cost of raw materials for synthesizing R-lipoic acid is greatly reduced, which provides a new way for industrial production of R-lipoic acid.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a treatment method for recycling S-(-)-lipoic acid. Background technique [0002] Alphalipoic acid is a coenzyme found in mitochondria, similar to vitamins, which can eliminate free radicals that lead to accelerated aging and disease. Lipoic acid enters the cells after being absorbed by the intestinal tract in the body. It has both fat-soluble and water-soluble properties, so it can pass through the whole body unimpeded, reach any cell site, and provide comprehensive efficacy for the human body. It is a fat-soluble and water-soluble universal antibiotic. oxidizing agent. Among them, the study found that lipoic acid plays a major role in the R-lipoic acid part. Therefore, the research on the synthesis of R-lipoic acid is of great significance for promoting the industrial production of R-lipoic acid. [0003] With the continuous deepening of the research on the synthe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/63C07C67/14C07C53/50C07C51/60
Inventor 钟锋刘玲玲李恒谢成杰
Owner TECHNO (FUJIAN) FOOD INGREDIENTS CO LTD
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