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Method for synthesizing folic acid by oxidizing 6-R-tetrahydrofolic acid

A tetrahydrofolate, oxidation synthesis technology, applied in chemical recovery, organic chemistry, etc., can solve the problems of increasing production costs, and achieve the effects of reducing production costs, simplifying the product separation process, and simply recycling and reusing

Pending Publication Date: 2022-03-11
HARBIN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The by-product 6-R-tetrahydrofolate in the production process of 6-S-5-methyltetrahydrofolate is a kind of non-biologically active substance, which can only be treated as production waste at present. The treatment process not only increases the production cost, but also cause major environmental problems

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1. racemic tetrahydrofolate 9g (20mmol) is dissolved in 50ml water, adds p-toluic acid 3.8g (22mmol) as resolving agent, separates after 6-S-tetrahydrofolate benzoate crystal The remaining mother liquor is about 50ml (wherein the tetrahydrofolate is about 4.6g). Adjust the pH value to 7, add 140 mg of the supported composite catalyst, stir at 25°C, slowly add 40 ml of hydrogen peroxide with a concentration of 5% dropwise, react for 6 hours, monitor the consumption of all raw materials by TLC, continue stirring for 60 minutes, and filter and recover the composite catalyst. The reaction solution was concentrated in vacuo to 50ml, adjusted to pH 3-4 with dilute hydrochloric acid, left to cool, and filtered to obtain 4.5g of crude folic acid product. The purity of the crude product folic acid analyzed by HPLC was 95.2%, and 4.13 g of folic acid was refined after ethanol recrystallization, with a purity of 98.5%. Calculated according to the content of 6-R-tetrahy...

Embodiment 2

[0020] Embodiment 2. By the feeding amount and operating process of embodiment 1, just change the hydrogen peroxide consumption into 27ml. Filter to obtain 4.0 g of folic acid crude product. The purity of the crude product folic acid analyzed by HPLC was 91.2%, and the refined folic acid was 3.52 g after ethanol recrystallization, with a purity of 98.4%. Calculated according to the content of 6-R-tetrahydrofolate in the split mother liquor, the yield of refined folic acid is 76.7%.

Embodiment 3

[0021] Embodiment 3. press the charging capacity and operating process of embodiment 1, just change the hydrogen peroxide consumption into 50ml. Filtration obtained 4.4 g of folic acid crude product. The purity of the crude product folic acid analyzed by HPLC was 94.9%, and 4.02 g of folic acid was refined after ethanol recrystallization, with a purity of 98.6%. Calculated according to the content of 6-R-tetrahydrofolate in the split mother liquor, the yield of refined folic acid is 88.1%.

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Abstract

The invention mainly relates to a method for synthesizing folic acid by oxidizing 6-R-tetrahydrofolic acid. The process for synthesizing folic acid by oxidizing 6-R-tetrahydrofolic acid is realized by the following method: adding a certain amount of hydrogen peroxide and a nickel porphyrin / manganese porphyrin composite catalyst loaded on a macroporous molecular sieve into the remaining mother liquor obtained by resolving 6-S-tetrahydrofolic acid benzoate crystals by taking benzoate as a resolving agent, and reacting for a period of time at low temperature to obtain folic acid. And monitoring the reaction by TLC, and filtering and recovering the composite catalyst after the reaction is finished. And carrying out vacuum concentration on the reaction liquid, cooling and standing to obtain a folic acid crude product. According to HPLC analysis, the purity of the crude product folic acid is greater than 95.2%, the purity of the refined folic acid after ethanol recrystallization is greater than 98.5%, and the yield of the refined folic acid is greater than 90% according to the content of 6-R-tetrahydrofolic acid in the resolution mother liquor.

Description

technical field [0001] The invention relates to a process for oxidatively synthesizing folic acid from 6-R-tetrahydrofolate, and belongs to the technical field of fine chemicals. Background technique [0002] 6-S-5-Methyltetrahydrofolate is known as active folic acid. It has better biological activity than folic acid and overcomes a series of side effects in the process of folic acid metabolism. It is a replacement product of folic acid. It is often used as the main component of food additives and nutritional health products, and is gradually known by people. 6-S-5-Methyltetrahydrofolate participates in many important biochemical reactions in the body and has important pharmacological effects. These drugs can pass through the blood-brain barrier and can prevent Alzheimer's disease, cellular anemia and other symptoms. Compared with other drugs, S-5-methyltetrahydrofolate has the characteristics of remarkable curative effect, complete functions and less side effects, and has...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D475/04
CPCC07D475/04Y02P20/584
Inventor 由君王静雯武文菊喻艳超刘其业
Owner HARBIN UNIV OF SCI & TECH
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