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A kind of preparation method of plant polyphenol acylated derivative

A plant polyphenol and polyphenol acyl technology, applied in organic chemistry, carbonyl formation/introduction, etc., to achieve the effects of preventing oxidation, simple synthesis method, and easy industrial operation

Inactive Publication Date: 2016-04-13
RUGAO ZHONGCHANG CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method uses the gemini surfactant system as both a reaction medium and a catalyst, which simplifies the reaction operation, prevents the loss of phenolic hydroxyl groups of plant polyphenols, and improves the conversion rate of C-acylation reaction. It is a green chemical technology , has not yet been reported

Method used

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  • A kind of preparation method of plant polyphenol acylated derivative
  • A kind of preparation method of plant polyphenol acylated derivative

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Effect test

Embodiment 1

[0022] The preparation of embodiment 1 gemini surface active agent

[0023] 1) Alkylation Add 16.8g (0.1mol) of diphenylmethane, anhydrous AlCl 3 13g, fully stirred to disperse the catalyst evenly, at 45-50°C, add 34g (0.2mol) of dodecene dropwise, the dropping time is controlled at 20-30min to complete the dropwise addition, then gradually raise the reaction temperature to 70°C, and keep No change, react for 8 hours, after the reaction, adjust the reaction solution to neutral, extract with toluene, dry over anhydrous magnesium sulfate, filter, concentrate to obtain the alkylated product for the next step of sulfonation;

[0024] 2) Sulfonation In a four-necked reaction flask equipped with an electric stirrer, a thermometer, a reflux condenser, and a dropping funnel, add the alkylated product obtained above, and add 24 g (0.2 mol) of chlorosulfonic acid dropwise under vigorous stirring. ), the dropping time is 1h, the reaction temperature is controlled at 20-25°C, and the rea...

Embodiment 2

[0026] Embodiment 2 plant polyphenols react with decanoyl chloride

[0027] Under nitrogen protection, mix 17 grams of plant polyphenol extract (containing 0.01 moles of plant polyphenols) with 29 grams of decanoyl chloride (0.15 moles), and 46 grams of gemini surfactant, and react at 50 ° C for 20 hours. After the reaction, The reaction solution was dissolved in 100 ml of petroleum ether, washed with 30×3 ml of saturated brine, the petroleum ether phase was dried with anhydrous sodium sulfate, and the petroleum ether solvent was evaporated under reduced pressure to obtain a white waxy plant polyphenol acylated derivative 36 grams, yield 77%.

Embodiment 3

[0028] Embodiment 3 plant polyphenols react with hexanoyl chloride

[0029] Under the protection of nitrogen, mix 17 grams of plant polyphenol extract (containing 0.01 mole of plant polyphenol) with 27 grams of hexanoyl chloride (0.2 mole), 132 grams of gemini surfactant, and react at 100 ° C for 10 hours. After the reaction, the The reaction solution was dissolved in 100 ml of petroleum ether, washed with 30×3 ml of saturated brine, the petroleum ether phase was dried over anhydrous sodium sulfate, and the petroleum ether solvent was evaporated under reduced pressure to obtain a white waxy plant polyphenol acylated derivative 39 gram, yield 89%.

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Abstract

The invention discloses a preparation method of plant polyphenol acylation derivatives. The method includes: under protection of nitrogen, mixing a plant polyphenol extraction product and acyl chloride, and fully reacting at 50-200 DEG C in a dimeric surfactant medium shown as the formula (I) to obtain the plant polyphenol acylation derivatives. The synthetic method is simple and convenient, free of use of acid catalysts, high in product conversion rate and low in cost, and can effectively prevent oxidation of raw materials. The yield is 88%. The reaction system can be reused. The method is suitable for industrialized operation. The dimeric surfactant can be recycled and is safe, stable, and free of pollution to the environment. The method is an economical and practical environmental protection technology.

Description

(1) Technical field [0001] The invention relates to a preparation method of plant polyphenol acylated derivatives, and relates to a method for catalytically synthesizing plant polyphenol acylated derivatives in a gemini surfactant system. (2) Background technology [0002] Plant polyphenols are secondary metabolites of plants, which are composed of gallic acid (or its polymers), glucose (and its polyols) alcohols, polymers of flavanols and their derivatives, and a mixture of the two. Composition of plant polyphenols. So far, more than 8,000 kinds of phenolic compounds have been isolated and identified from plants, and more than 600 kinds of common plants contain more polyphenols. The content of plant polyphenols in the bark of many conifers is as high as 20-40%. Fruits, grains or their skins Contains high plant polyphenols, forming hundreds of millions of tons of renewable resources around the world. Plant polyphenols can combine with proteins, alkaloids, and polysaccharid...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B41/06C07G99/00
Inventor 裴文方苗利杨振平胡卫雅孙莉
Owner RUGAO ZHONGCHANG CHEM
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