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Preparation method of caffeic acid

A technology of caffeic acid and hydrocyanic acid, which is applied in the direction of carboxylate preparation, organic compound preparation, chemical instruments and methods, etc., can solve the problems of harsh reaction conditions, low yield, long production cycle, etc., and shorten the reaction time , reduce production cost, reduce the effect of production cycle

Inactive Publication Date: 2012-10-31
湖北远成赛创科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Of the above three routes, route (1) is more reasonable, the process is more mature, and is suitable for industrial production, but the current route (1) still has the disadvantages of low yield, unsatisfactory caffeic acid purity, and long production cycle. , the impact of 4-dihydroxybenzaldehyde and malonic acid condensation into caffeic acid is more prominent. The reaction time of this step is long, the yield is low, and the stability of the product is affected; The disadvantage of being too low is not suitable for large-scale industrial production; and route (3) although the process is simple and the yield is high, the price of 3,4-dihydroxybenzaldehyde as a raw material is 3 to 3 of the price of caffeic acid. 4 times

Method used

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  • Preparation method of caffeic acid

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Experimental program
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Effect test

Embodiment 1

[0023] In the first step, 500Kg of 3,4-dihydroxyphenylacetaldehyde was dissolved in 0.5kg of DBU (1,8-diazabicyclo[ 5.4.0] Undec-7-ene) in PEG-200 (polyethylene glycol 200); at 35°C, 8Mpa, 1000kg of hydrogen cyanide gas is passed in within 3 hours; hydrogen cyanide gas is passed into After 1h, start to pass ScCO 2 (Supercritical carbon dioxide) extract the addition product to obtain the addition product;

[0024] In the second step, under the condition of microwave radiation with a power of 500w and a frequency of 2500Hz, the addition product is hydrolyzed at 90°C and pH value 3 for 2 hours, then distilled under reduced pressure to precipitate the hydrolyzate, and then rinsed with acidic water for 2-3 After drying under reduced pressure to obtain the hydrolyzate;

[0025] In the third step, under the condition of microwave radiation with a power of 1500w and a frequency of 2000Hz, the hydrolyzate is circulated through the solid acid complex γ-Al at 120°C and -0.1MPa. 2 o 3...

Embodiment 2

[0027] In the first step, under the condition of microwave radiation with a power of 1200w and a frequency of 1500Hz, 500Kg of 3,4-dihydroxyphenylacetaldehyde was dissolved in 5kg of DBNPA (2,2-dibromo-3-cyano Propionamide) in PEG-200 (polyethylene glycol 200); at 20°C, 10Mpa, 1200kg of hydrocyanic acid gas was introduced within 5 hours; after 1 hour of hydrocyanic acid gas, ScCO was introduced. 2 (Supercritical carbon dioxide) extract the addition product to obtain the addition product;

[0028] In the second step, under the condition of microwave radiation with a power of 700w and a frequency of 3500Hz, the addition product is hydrolyzed at 50°C and pH value 2 for 3 hours, then distilled under reduced pressure to precipitate the hydrolyzate, and then rinsed with acidic water for 2-3 hours. After drying under reduced pressure to obtain the hydrolyzate;

[0029] In the third step, under the condition of microwave radiation with a power of 800w and a frequency of 2500Hz, the h...

Embodiment 3

[0031] In the first step, under the conditions of microwave radiation with a power of 1800w and a frequency of 3000Hz, 500Kg of 3,4-dihydroxyphenylacetaldehyde was dissolved in PEG-200 (polyethylene glycol) pre-mixed with 1kg of tetrabutylammonium hydroxide. 200); under the conditions of 25°C and 16Mpa, 1500kg of hydrocyanic acid gas was introduced within 8 hours; after 1 hour of hydrogen cyanide gas, ScCO was introduced 2 (Supercritical carbon dioxide) extract the addition product to obtain the addition product;

[0032] In the second step, under the condition of microwave radiation with a power of 900w and a frequency of 3000Hz, the addition product was hydrolyzed at 60°C and pH value 3 for 1 hour, then distilled under reduced pressure to precipitate the hydrolyzate, and then washed with acidic water for 2-3 After drying under reduced pressure to obtain the hydrolyzate;

[0033] In the third step, under the condition of microwave radiation with a power of 1200w and a freque...

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Abstract

The invention provides a preparation method of caffeic acid, which comprises the following steps: step one: 3,4-dihydroxyphenylacetic acid is dissolved in polyethylene glycol 200 mixed with an entrainer, hydrocyanic acid is introduced to carry out the addition reaction under the condition of radiation of microwaves with power of 1,000 to 1,800 W, and then supercritical carbon dioxide is added to extract an addition product; step two: the addition product is hydrolyzed, separated and purified to obtain a hydrolysis product; and step three: the hydrolysis product is dehydrated to obtain caffeic acid. The method has the advantages of mild condition and less side reaction, is favorable to environmental protection, simplifies the production process, shortens the reaction time, reduces the production cost and the production period greatly, is simple and feasible under the industrial production condition, has more than 90% of yield, and is easy to achieve the industrial batch production; and the produced waste is less and easy to treat. Meanwhile, 3,4-dihydroxyphenylacetic acid can be prepared from pyrocatechol through a simple process route, so that the cost is reduced greatly.

Description

technical field [0001] The invention belongs to the field of drug synthesis, in particular to a preparation method of caffeic acid. Background technique [0002] Caffeic acid, English name: Caffeic acid, chemical name: 3-(3,4-dihydroxyphenyl)-acrylic acid, molecular formula: C9H8O4, molecular weight: 180.13, chemical structural formula as shown below: [0003] [0004] Caffeic acid is a component of chlorogenic acid contained in various Chinese herbal medicines such as ramie, capillary, and artichoke. It has been proved by pharmacological experiments that it has a wide range of antibacterial effects and antiviral activity; caffeic acid has shrinkage and strengthening properties. Microvessels, improve the function of coagulation factors, and increase the effect of white blood cells and platelets, which can be used to produce surgical operations to prevent bleeding or stop bleeding, as well as hemostatic drugs for bleeding diseases such as internal medicine, obstetrics and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C59/52C07C51/347
CPCY02P20/54
Inventor 叶思朱如慧杨启伟周艳丽
Owner 湖北远成赛创科技有限公司
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