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 low yield, long production cycle, harsh reaction conditions, etc., and reduce production cost , Simplify the production process, reduce the effect of production cycle

Inactive Publication Date: 2014-11-05
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
  • Preparation method of caffeic acid

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Experimental program
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Effect test

Embodiment 1

[0023] The first step is to dissolve 500Kg of 3,4-dihydroxyphenylacetaldehyde into 0.5kg of DBU(1,8-diazabicyclo[ 5.4.0] Undec-7-ene) in PEG-200 (polyethylene glycol 200); under the conditions of 35°C and 8Mpa, 1000kg of hydrogen cyanide gas is introduced within 3 hours; hydrogen cyanide gas is introduced Start to enter ScCO after 1h 2 (Supercritical carbon dioxide) Extract the addition product to obtain the addition product;

[0024] In the second step, under the conditions of microwave radiation with a power of 500w and a frequency of 2500Hz, the addition product is hydrolyzed at 90℃ and pH 3 for 2 hours, then vacuum distillation is used to precipitate the hydrolysate, and then rinsed with acidic water for 2-3 After drying under reduced pressure, the hydrolyzate is obtained;

[0025] In the third step, under the conditions of microwave radiation with a power of 1500W and a frequency of 2000Hz, the hydrolyzed product circulates through the solid acid complex γ-Al at 120°C and -0....

Embodiment 2

[0027] The first step is to dissolve 500Kg of 3,4-dihydroxyphenylacetaldehyde into 5kg of DBNPA (2,2-dibromo-3-cyanoacetaldehyde) under microwave radiation with a power of 1200w and a frequency of 1500Hz. Propionamide) in PEG-200 (polyethylene glycol 200); under the conditions of 20°C and 10Mpa, 1200kg of hydrocyanic acid gas is introduced within 5 hours; ScCO is introduced after 1 hour of hydrocyanic acid gas 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 power of 700w and frequency of 3500Hz, the addition product is hydrolyzed at 50℃, pH value 2 for 3h, then vacuum distillation is carried out to precipitate the hydrolysate, and then rinsed with acidic water for 2-3 After drying under reduced pressure, the hydrolyzate is obtained;

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

Embodiment 3

[0031] The first step is to dissolve 500Kg of 3,4-dihydroxyphenylacetaldehyde in PEG-200 (polyethylene glycol) premixed with 1kg of tetrabutylammonium hydroxide under microwave radiation with a power of 1800w and a frequency of 3000Hz. 200); Under the condition of 25℃ and 16Mpa, 1500kg of hydrocyanic acid gas is introduced within 8 hours; ScCO is introduced after 1 hour of hydrocyanic acid gas 2 (Supercritical carbon dioxide) Extract the addition product to obtain the addition product;

[0032] In the second step, under the conditions of microwave radiation with a power of 900w and a frequency of 3000Hz, hydrolyze the addition product at 60℃ and pH 3 for 1 hour, and then distill under reduced pressure to precipitate the hydrolysate, and then rinse with acidic water for 2-3 After drying under reduced pressure, the hydrolyzate is obtained;

[0033] In the third step, under the conditions of microwave radiation with a power of 1200w and a frequency of 3000Hz, the hydrolyzed product is...

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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, and specifically refers to a method for preparing 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, the chemical structure formula is shown in the figure below: [0003] [0004] Caffeic acid is a component of chlorogenic acid contained in many Chinese herbal medicines such as ramie, hemp, and artichoke. Pharmacological experiments have shown that it has a wide range of antibacterial effects and has antiviral activity; caffeic acid has contraction and firmness Capillaries, improve the function of coagulation factors, increase the role of white blood cells and platelets, can be used to produce surgical operations to prevent bleeding or hemostasis, and internal medicine, obstetrics and gynecology and other bleeding diseases hemostatic drugs, can also be used to produce...

Claims

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Application Information

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Patent Type & Authority Patents(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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