Method for preparing alpha-lipoic acid

A technology of lipoic acid and sodium lipoic acid, applied in directions such as organic chemistry, can solve the problems such as complicated synthesis steps, harsh conditions, and difficulty in increasing the yield, and achieve the effects of reducing the generation of impurities, being easy to operate, and improving the purity.

Active Publication Date: 2014-11-19
SHANDONG QIDU PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the 1960s, this research reached a certain stage, and several routes that could be industrialized were obtained, but it was difficult to increase the yield
The raw material cost of this method is low, but the yield is only 45%, the yield is low, and the conditions are relatively harsh, which is not conducive to the realization of industrialization
[0013]In short, the yield of each synthetic route of lipoic acid is not more than 50%, and most of the routes are extremely expensive and the synthetic steps are cumbersome

Method used

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  • Method for preparing alpha-lipoic acid
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  • Method for preparing alpha-lipoic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0045] Add 80 g of purified water into a 500 mL beaker, add 21.8 g of sodium sulfide under stirring, dissolve at 35° C., and prepare a sodium sulfide solution.

[0046] Into a 500 mL round bottom flask, 50 g of ethyl 6.8-dichlorooctanoate, 150 g of purified water, 8 g of sulfur, and 3.5 g of tetrabutylammonium bromide were added. Heat to 82°C under stirring, add sodium sulfide solution dropwise, and finish dropping in 1 hour, and the dropping temperature is kept at 70°C. After the dropwise addition, the reaction was continued for 5 hours, the temperature was lowered to 65° C., and the mixture was left to stand for about 60 minutes, and the layers were separated to obtain 48.3 g of ethyl lipoic acid. Then put ethyl lipoic acid, 1600g of drinking water, 24.2g of sodium hydroxide and 1.93g of tetrabutylammonium bromide into the hydrolysis kettle into a 3000mL reaction kettle, stir, heat to 70°C, keep it warm for 13 hours, and pump it out while it is hot. Filter it into a 5L reac...

Embodiment 2

[0050] Add 120g of purified water into a 500mL beaker, add 31.2g of sodium sulfide under stirring, dissolve at 40°C, and prepare a sodium sulfide solution.

[0051] In a 500 mL round bottom flask, 50 g of ethyl 6.8-dichlorooctanoate, 150 g of drinking water, 15 g of sulfur, and 3.5 g of tetrabutylammonium bromide were added. Heat to 84°C under stirring, add sodium sulfide solution dropwise, and finish dropping in 1.5 hours, and keep the dropping temperature at 86°C. After the dropwise addition, the reaction was continued for 5 hours, the temperature was lowered to 65° C., and the mixture was left to stand for about 60 minutes, and the layers were separated to obtain 48.1 g of ethyl lipoic acid. Then put ethyl lipoic acid, 1600g of drinking water, 48.1g of sodium hydroxide and 1.92g of tetrabutylammonium bromide into the hydrolysis kettle into a 3000mL reaction kettle, stir, heat to 50°C, keep it warm for 13 hours, and pump it out while it is hot. Filter into a 5L reaction ket...

Embodiment 3

[0055] Add 100 g of purified water into a 500 mL beaker, add 25 g of sodium sulfide under stirring, dissolve at 37°C, and prepare a sodium sulfide solution.

[0056] In a 500 mL round bottom flask, add 50 g of ethyl 6.8-dichlorooctanoate, 150 g of drinking water, 10 g of sulfur, and 3.5 g of tetrabutylammonium bromide. Heat to 83°C under stirring, add sodium sulfide solution dropwise, and finish dropping in 1.2 hours, the dropping temperature is kept at 84°C. After the dropwise addition, the reaction was continued for 5 hours, the temperature was lowered to 65° C., and the mixture was left to stand for about 60 minutes, and the layers were separated to obtain 47.7 g of ethyl lipoic acid. Then put ethyl lipoic acid, 1600g of drinking water, 54.8g of sodium hydroxide and 1.9g of tetrabutylammonium bromide into the hydrolysis kettle into a 3000mL reaction kettle, start stirring, heat to 80°C, and keep it warm for 13 hours. Suction filter into a 5L reaction kettle, add dropwise 5...

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Abstract

The invention discloses a method for preparing alpha-lipoic acid, comprising the following steps: preparing the sodium sulphide liquor, synthesizing lipoic acid ethyl ester, hydrolyzing the lipoic acid ethyl ester, acidizing the sodium thioctate, and purifying the crude product of the lipoic acid. The liquor adopted by the method during the preparation process has no pollution for human bodies, is safe and easy to operate, and has the performances of high lipoic acid purity, high reaction yield and gentle reaction conditions, so that the method is suitable for industrial production on large scales.

Description

technical field [0001] The invention relates to a preparation method of α-lipoic acid, which belongs to the technical field of medicine preparation. Background technique [0002] The chemical name of α-lipoic acid is (±)-5-[3'-(1',2'-dithiolane)-]pentanoic acid, and its structural formula is as follows: . [0003] α-lipoic acid (alpha lipoic acid) is an enzyme present in mitochondria, similar to vitamins, which can eliminate free radicals that accelerate aging and cause disease. Alpha-lipoic acid enters the cells after being absorbed by the intestines 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 performance for the human body. It is fat-soluble and water-soluble Universal antioxidant. Dr. Lester Packer of the University of California, Berkeley is the world's top authority on α-lipoic acid and antioxidants. Alpha-lipoic acid is used to prevent and even tr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D339/04
Inventor 李洁朱建益董旭郑亮刘明明宋彩香于长安张涛李福海李后涛
Owner SHANDONG QIDU PHARMA
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