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Method for synthesizing ferulic acid by microwave radiation

A technology of microwave radiation and ferulic acid, which is applied in the field of synthesis of ferulic acid, can solve the problems of long reaction time and achieve the effects of short reaction time, expansion of the reaction system, and simple separation and purification operations

Inactive Publication Date: 2014-11-19
黄金凤
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The Knoevenagel reaction method is to add a small amount of organic base in the pyridine solvent as a catalyst, and the Knoevenagel reaction between vanillin and malonic acid produces ferulic acid, but the reaction time of this method is long, up to 3 weeks

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  • Method for synthesizing ferulic acid by microwave radiation
  • Method for synthesizing ferulic acid by microwave radiation
  • Method for synthesizing ferulic acid by microwave radiation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1 The method for the synthesis of ferulic acid by microwave radiation

[0035] Put 20mmol vanillin, a certain amount of acetic anhydride (that is, reactant is also solvent) and 20mmol Anhydrous Potassium Carbonate in dry round-bottomed flask, after shaking up, put into microwave chemical reactor, install reflux condenser, Under anhydrous conditions, under a certain microwave power, microwave radiation was continued for several minutes until the reaction mixture was completely melted into a liquid. The molten liquid was cooled to room temperature to obtain a solidified product, and about 70 mL of ice water was added to the obtained solid, shaken and mixed, left to stand for one day, fully washed with about 200 mL of ice water and suction filtered. The filter cake was hydrolyzed in 20% NaOH solution at 50°C for 20 minutes, and filtered with suction. The obtained filtrate was acidified with hydrochloric acid to pH = 2-3, filtered with suction to obtain a filter...

Embodiment 2

[0045] Embodiment 2 The influence of acetic anhydride consumption on productive rate

[0046] Carry out the method for synthesizing ferulic acid according to embodiment 1, vanillin consumption is 3.0g (20mmol), anhydrous potassium carbonate 2.8g (20mmol), microwave power 240W, microwave time 10min, investigate the influence of acetic anhydride consumption on productive rate , see the result Figure 4 . Depend on Figure 4 It can be seen that the productive rate increases with the increase of the amount of acetic anhydride. When the amount of acetic anhydride is 200mmol, the productive rate is the largest, and when it exceeds 200mmol, the productive rate decreases instead. This may be because the amount of acetic anhydride used is too much, which reduces the catalytic effect of the catalyst. The amount of acetic anhydride is too small, for example, when the acetic anhydride is 60mmol, the liquid after the reaction is black. This may be because there is no other solvent in th...

Embodiment 3

[0047] Example 3 Effect of Microwave Power on Productivity

[0048] Carry out the method for synthesizing ferulic acid according to embodiment 1, vanillin consumption is 3.0g (20mmol), anhydrous potassium carbonate 2.8g (20mmol), acetic anhydride 200mmol, microwave time 10min, investigate the influence of microwave power on productive rate, see results Figure 5 . Depend on Figure 5 It can be seen that with the increase of the radiation power, the yield increases, and the increase of the microwave power promotes the increase of the effective collision between the reactants, which is beneficial to the increase of the yield. Depend on Figure 5 It can also be seen that when the radiation power exceeds 400W, the yield increases slowly. From the consideration of saving energy, the microwave radiation power is more suitable for 400W.

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Abstract

The invention discloses a method for synthesizing ferulic acid by microwave radiation. The method comprises the following steps: adding vanillic aldehyde and anhydrous potassium carbonate to acetic anhydride, evenly mixing the raw materials, and carrying out microwave radiation until a reaction mixture is completely molten into liquid; cooling the molten liquid to room temperature and then adding ice water to mix evenly; standing the mixture for over 24 hours, adding ice water again, fully washing and carrying out suction filtration to obtain a filter cake; hydrolyzing the filter cake in an NaOH solution, and carrying out suction filtration; acidizing the obtained filtrate until the pH is 2-3, carrying out suction filtration, and recrystallizing the filtrate cake by using absolute ethyl alcohol, so as to obtain yellow needle crystal; drying the yellow needle crystal to obtain ferulic acid. Acetic anhydride is a reactant, and also is a solvent; acetic anhydride can react to the maximal extent; anhydrous potassium carbonate is non-toxic and pollution-free; acetic anhydride is taken as the solvent, and can be removed in a washing manner during impurity removal; the requirements of green chemistry are met, therefore, the method disclosed by the invention is short in reaction time, and easy in separation and purification, the productive rate can be up to 68%, and a new direction is provided for preparation of ferulic acid.

Description

technical field [0001] The invention relates to a synthesis method of ferulic acid, in particular to a method for synthesizing ferulic acid by microwave radiation. Background technique [0002] Ferulic acid (FA for short), chemically named 4-hydroxy-3-methoxyphenylacrylic acid, widely exists in plants and is one of the active ingredients of commonly used traditional Chinese medicines (angelica, chuanxiong, etc.). As a metabolite of oryzanol in the body, ferulic acid has anti-thrombotic, anti-inflammatory, analgesic, anti-oxidation, anti-ultraviolet radiation and anti-free radical effects. At present, ferulic acid is widely used in medicine, food, cosmetics and other fields. The content of ferulic acid in plants is generally about 0.03%, and the cost of extracting it from plants is relatively high. With the continuous improvement of pharmaceutical research and the quality of human life, the demand for ferulic acid in pharmaceutical synthesis, health care products and cosmet...

Claims

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Application Information

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IPC IPC(8): C07C59/64C07C27/02C07C67/293C07C69/157
CPCC07C51/09C07C67/293C07C69/157C07C59/64
Inventor 黄金凤童跃进
Owner 黄金凤
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