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Caffeic acid synthesis and refining process

A caffeic acid and process technology, applied in the field of caffeic acid synthesis and refining process, can solve the problems of large amount of solvent, high production cost, and low product yield, and achieve the effects of avoiding organic solvent extraction, low cost, and easy recovery

Active Publication Date: 2019-01-01
DEZHOU DEYAO PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the addition reaction, pyridine is used as the reaction solvent and condensation catalyst, the amount of solvent is large, the operation is complicated and the production cost is high, the product yield is low (only about 70%), and the purity is poor
Therefore, its application is limited
In foreign patents, there is currently no patent on the chemical synthesis of caffeic acid. They are usually extracted from plants by means of traditional Chinese medicine extraction.

Method used

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  • Caffeic acid synthesis and refining process
  • Caffeic acid synthesis and refining process
  • Caffeic acid synthesis and refining process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1 prepares caffeic acid crude product

[0024] Take 30g of 3,4-dihydroxybenzaldehyde and 60.0g of malonic acid, add 300ml of N,N-dimethylformamide to dissolve, add 45mL of pyridine, and then raise the temperature to 70°C. Add 9 mL of aniline and react for 1 hour. After the reaction, the temperature of the reaction liquid was lowered to below 30°C, 1000ml of 2moL / L hydrochloric acid was added and stirred, and stirred at room temperature for 2h to crystallize. Suction filtration, the filter cake was washed twice with 300ml purified water. Blast drying at 50°C yielded 36.50 g of crude yellow caffeic acid, with a yield of 93.60%, a purity of 99.52%, and a content of 99.2%.

Embodiment 2

[0025] Embodiment 2 prepares caffeic acid crude product

[0026] Take 30g of 3,4-dihydroxybenzaldehyde, 60.0g of malonic acid and add 300ml of tetrahydrofuran to dissolve, add 45mL of pyridine, and then raise the temperature to 70°C. Add 9 mL of aniline and react for 1 hour. After the reaction, the temperature of the reaction liquid was lowered to below 30°C, 1000ml of 2moL / L hydrochloric acid was added and stirred, and stirred at room temperature for 2h to crystallize. Suction filtration, the filter cake was washed twice with 300ml purified water. Blast drying at 50°C yielded 36.38 g of crude yellow caffeic acid, with a yield of 93.28%, a purity of 99.61%, and a content of 99.0%.

Embodiment 3

[0027] Embodiment 3 prepares caffeic acid crude product

[0028] Take 30g of 3,4-dihydroxybenzaldehyde, 60.0g of malonic acid and add 300ml of methanol to dissolve, add 45mL of pyridine, and then raise the temperature to 70°C. Add 9 mL of aniline and react for 1 hour. After the reaction, the temperature of the reaction liquid was lowered to below 30°C, 1000ml of 2moL / L hydrochloric acid was added and stirred, and stirred at room temperature for 2h to crystallize. Suction filtration, the filter cake was washed twice with 300ml purified water. Blast drying at 50°C yielded 36.44 g of crude yellow caffeic acid, with a yield of 93.44%, a purity of 99.64%, and a content of 99.4%.

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Abstract

The invention relates to a caffeic acid synthesis and refining process, a raw material 3,4-dihydroxybenzaldehyde and a raw material propane diacid are condensed in a solvent under the effect of an organic base condensation catalyst and a decarboxylation catalyst to form caffeic acid, After the reaction is completed, the acid is added to obtain a caffeic acid crude product, the caffeic acid crude product is added to water to dissolve, and the activated carbon is added for decolouring, and the pale yellow solid is precipitated, filtered, and dried under vacuum to obtain the caffeic acid. The process improves the reaction yield, controls the generation of impurities, has simple operation, and mild reaction conditions, and the reaction time is greatly shortened; the process innovatively selects other solvents, reduces the amount of pyridine, and has the advantages of low cost and easy recovery, at the same time, the molar ratio, reaction temperature and reaction time of each initial raw material are further optimized, the organic solvent extraction is avoided, the post-treatment step is simplified, and the direct crystallization is performed after adding hydrochloric acid, and the pressure of the three-waste treatment can be reduced. The caffeic acid content is greater than 99.5%, and the single impurity of the caffeic acid which can stably controlled being not more than 0.1%.

Description

technical field [0001] The invention relates to the technical field of water body sterilization and disinfection, in particular to a process for synthesizing and refining caffeic acid. Background technique [0002] Caffeic acid is widely distributed in capillary, artichoke, honeysuckle and other traditional Chinese medicine plants. It belongs to phenolic acid compounds and has cardiovascular protection, anti-mutation and anti-cancer, anti-bacterial and anti-viral, lipid-lowering and hypoglycemic, anti-leukemia and immune regulation. , choleretic hemostasis and anti-oxidation and other pharmacological effects. Caffeic acid can shrink and strengthen microvessels, reduce permeability, increase blood coagulation function and the number of white blood cells and platelets. It is often used clinically for the prevention and treatment of various surgical and medical bleeding, and has a significant effect on gynecological bleeding diseases. It is also used for chemotherapy of tumor d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/38C07C51/42C07C51/43C07C59/52
CPCC07C51/38C07C51/42C07C51/43C07C59/52
Inventor 卞建钢李成文刘相国刘秀朋马浩张华巍刘伟
Owner DEZHOU DEYAO PHARMA
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