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Method for microwave-assisted fast and efficient preparation of phenethyl caffeate

A caffeic acid phenethyl ester and microwave-assisted technology are applied in the preparation of carboxylic acid esters, chemical instruments and methods, and the preparation of organic compounds. The effect of improving the utilization rate

Active Publication Date: 2015-01-07
INST OF OIL CROPS RES CHINESE ACAD OF AGRI SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the report on the synthesis of caffeic acid phenethyl ester, there are very few research reports on the enzymatic synthesis of caffeic acid phenethyl ester by means of microwave crop enhancement. Hydroxybenzaldehyde and phenylethyl acetate are catalyzed by organic bases to synthesize phenethyl caffeate by microwave radiation. The catalyst and solvent of this method are organic matter, which is not conducive to environmental protection
There is no report on the rapid and efficient synthesis of phenethyl caffeate using ionic liquids as catalysts and solvents under microwave-assisted conditions

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] A kind of microwave-assisted fast and efficient method for preparing phenethyl caffeate, it comprises the steps:

[0025] (1) Pretreatment of raw materials: reaction solvent [Bmim] [PF 6 ] and caffeic acid were vacuum-dried at 60° C. for 8 hours, respectively, and the moisture content was controlled below 1 wt %; phenylethanol was dehydrated by anhydrous sodium sulfate, and the moisture content was controlled below 0.2 wt %;

[0026] (2) Adding of reaction raw materials (the molar ratio of caffeic acid and phenylethyl alcohol is 1:1): mix 72g caffeic acid, 49g phenylethyl alcohol, 72g[Bmim][PF 6 ] and 4.8g molecular sieves are added in the reactor (the addition of molecular sieves is 50g / L, and 50g molecular sieves are added in every liter of reaction solvent), stir under normal temperature, obtain premixture, logical nitrogen deoxygenation 5min, obtain the deoxygenation after premix;

[0027] (3) Microwave-assisted transesterification reaction: add antioxidant L-asco...

Embodiment 2

[0030] A kind of microwave-assisted fast and efficient method for preparing phenethyl caffeate, it comprises the steps:

[0031](1) Pretreatment of raw materials: reaction solvent [Bmim] [Tf 2 N] and caffeic acid were vacuum-dried at 70° C. for 12 hours respectively, and the moisture content was controlled below 1 wt %; phenylethyl alcohol was dehydrated by anhydrous sodium sulfate, and the moisture content was controlled below 0.2 wt %;

[0032] (2) Adding of reaction raw materials (caffeic acid and phenylethyl alcohol molar ratio is 1:10): 36g caffeic acid, 245g phenylethyl alcohol, 360g[Bmim][Tf 2 N] and 28.6g molecular sieves are added in the reaction kettle (at this moment, the addition of molecular sieves is 60g / L, and 60g molecular sieves are added in every liter of reaction solvent), stir under normal temperature, obtain premixture, logical nitrogen removes oxygen 5min, obtains Deoxygenated premix;

[0033] (3) Microwave-assisted transesterification reaction: Add ant...

Embodiment 3

[0036] A kind of microwave-assisted fast and efficient method for preparing phenethyl caffeate, it comprises the steps:

[0037] (1) Pretreatment of raw materials: reaction solvent [Emim]PF 6 Vacuum-dried at 80°C for 12 hours; caffeic acid was vacuum-dried at 80°C for 12 hours, and the moisture content was controlled below 1wt%; phenylethanol was dehydrated with anhydrous sodium sulfate, and the moisture content was controlled below 0.2wt%;

[0038] (2) Adding of reaction raw materials (the molar ratio of caffeic acid to phenylethyl alcohol is 1:20): 14.4g caffeic acid, 195.5g phenylethyl alcohol, 288g [Emim]PF 6 and 30.5g molecular sieves (at this time, the addition of molecular sieves is 80g / L, and 80g molecular sieves are added to every liter of reaction solvent) into the reaction kettle, stirred evenly at normal temperature, to obtain a premix, and nitrogen to remove oxygen for 5min, to obtain oxygen removal After the premix;

[0039] (3) Microwave-assisted transesterifi...

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PUM

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Abstract

The invention relates to a preparation method of phenethyl caffeate. The preparation method is characterized by comprising the following steps: 1) putting reaction raw materials, namely adding caffeic acid, phenethyl alcohol, a reaction solvent and a molecular sieve into a reaction kettle, and uniformly stirring at normal temperatures to obtain a pre-mixture; introducing nitrogen to remove oxygen for 5 minutes to obtain the deoxidized pre-mixture, wherein the molar ratio of caffeic acid and phenethyl alcohol is (1:1)-(1:20), the mass ratio of caffeic acid and the reaction solvent is (1:1)-(1:20), and the addition amount of the molecular sieve is 50-80g / L; 2) carrying out microwave-assisted transesterification, namely adding 100-200ppm antioxidant into the deoxidized pre-mixture, controlling the temperature at 120-140 DEG C, stirring at an ordinary pressure for reaction for 5-20 minutes under a microwave-assisted condition, stopping microwave heating, and naturally cooling to 40 DEG C; and 3) carrying out post-treatment of a product to obtain phenethyl caffeate. The method has the characteristics of rapid reaction, simplicity in operation and mild reaction condition, the utilization ratio of raw materials can be effectively improved, and the prepared product phenethyl caffeate is high in purity and yield.

Description

technical field [0001] The present invention relates to a preparation method of caffeic acid phenethyl ester, in particular to a method for rapidly and efficiently preparing caffeic acid phenethyl ester by using ionic liquid as a solvent and a catalyst under the assistance of microwaves, which belongs to natural product molecular modification and lipid Deep processing field. Background technique [0002] Caffeic acid phenylethyl ester (CAPE), the chemical name is 3-(3', 4'-dihydroxyphenyl)-2-phenylethyl acrylate, is the main active ingredient in propolis, has anti-oxidation, anti-virus, anti-inflammatory DNA, inducing apoptosis, antibacterial, anti-inflammatory, anti-arteriosclerosis and improving immunity and other pharmacological activities, showing unique physiological and pharmacological effects in anti-tumor, anti-oxidation, anti-inflammation, immune regulation and other aspects. Among them, the anti-tumor activity is the most significant, and it has attracted much att...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/732C07C67/08
CPCC07C67/08C07C69/732
Inventor 黄凤洪郑明明黄清向霞邓乾春李文林时杰万楚筠
Owner INST OF OIL CROPS RES CHINESE ACAD OF AGRI SCI
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