Preparation method of gallic acid high grade alxoxide ester

A technology for acid higher alkanol ester and gallic acid, which is applied in the field of preparation of higher gallic acid alkanol ester, can solve the problems of difficult control of process conditions, difficult regeneration and recycling, difficulty in industrial application, etc. Programmatic, the effect of shortened response time

Inactive Publication Date: 2004-12-22
南京龙源天然多酚合成厂
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Japanese patent (JP Zhao 52-48966) uses dioxane as the water-carrying agent in the esterification reaction yield is higher, but uses anhydrous potassium carbonate as the dehydrating agent, the dehydration time is long, and it is not easy to regenerate and recycle
The steps of water-carrying, dehydration and solvent recovery in the above process are carried out intermittently, the process is complicated, the process conditions are difficult to control, the product quality is unstable, the yield is low, and the cost is high, so industrial application is difficult

Method used

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  • Preparation method of gallic acid high grade alxoxide ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] The reactor with stirring, thermometer and heating mantle is connected with condenser and alumina microporous ceramic tube in turn.

[0019] Put 96g of gallic acid, 88g of n-octanol, 28g of catalyst dodecylbenzenesulfonic acid and an appropriate amount of water-bearing solvent 1,4-dioxane into the reactor, stir and heat, and keep the temperature in the reactor at 108-110°C. reaction for 8 hours. During this process, the gaseous 1,4-dioxane in the reactor will take the water generated by the reaction from the top of the reactor in the form of steam, condense into a liquid phase through the condenser, and absorb the water through the alumina microporous ceramic tube Return to the reactor for recycling. After the reaction was finished, the reactant was distilled under reduced pressure to recover the solvent, then heated to dissolve with toluene, and the solution was recrystallized to obtain 148 g of octyl gallate, with a yield of 94%. The melting point of the product is ...

Embodiment 2

[0021] The device is the same as in Example 1, put into the reactor 96g of gallic acid, 215g of stearyl alcohol, 15g of catalyst p-toluenesulfonic acid, and an appropriate amount of solvent 1,4-dioxane, stir and heat, and keep the temperature in the device at 115-120°C. reaction for 14 hours. After the solvent was recovered from the reaction mixture, the crude product was dissolved in xylene and recrystallized to obtain 373 g of stearyl gallate (92% yield), with a melting point of 101-102°C. As determined by mass spectrometry, the molecular weight of the product was 422.

Embodiment 3

[0022] Example 3 The yields of various products of higher alkanol gallate prepared by the method of the present invention are shown in the following table.

[0023] sequence

[0024] Acids Alcohols Catalyst Water with water Solvent Product Yield%

[0025] No

[0026] 1 Gallic acid n-octanol Dodecylbenzenesulfonic acid 1,4-dioxane Octyl gallate 94

[0027] 2 Gallic acid Lauryl alcohol p-toluenesulfonic acid 1,4-dioxane Lauryl gallate 97

[0028] 3 gallic acid myristyl alcohol p-toluenesulfonic acid 1,4-dioxane tetradecyl gallate 94

[0029] 4 gallic acid cetyl alcohol p-toluenesulfonic acid 1,4-dioxane cetyl gallate 91

[0030] 5 gallic acid stearyl alcohol p-toluenesulfonic acid 1,4-dioxane octadecyl gallate 92

[0031] 6 gallic acid eicosanol p-toluenesulfonic acid 1,4-dioxane eicosyl gallate 93

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Abstract

A process for preparing the high-grade alkanol ester for gallic acid, whose chemical formula is (HO)3C6H2COOCnH2n+1, includes catalytic reaction between gallic acid, high-grade alkanol, and solvent at 105-125 deg.C, carrying to resultant vapour out of the reactor by the evaporated solvent, condensing, removing water by millpore ceramic column, returning solvent back to reactor, continuous circulation until reaction is terminated, and recrystallizing.

Description

(technical field) [0001] The present invention relates to molecular general formula is (HO) 3 C 6 h 2 COOC n h 2n+1 The preparation method of the higher alkanol gallic acid ester, especially the preparation method of the higher alkanol gallic acid ester with n=8,10,12,14,16,18,20. (Background technique) [0002] Higher alkanol gallate is white to off-white crystalline powder, and its molecular formula is: [0003] (HO) 3 C 6 h 2 COOC n h 2n+1 (n=8, 10, 12, 14, 16, 18, 20) [0004] Higher alkanol gallate is an oxygen free radical scavenger and antioxidant. Because this kind of substance has the effect of anti-platelet aggregation and dilating blood vessels, and its anti-oxidation effect is better than that of Vc, it is a kind of promising drug and excellent food antioxidant. Among them, lauryl gallate is more collected by British and American Pharmacopoeia, and it is a food antioxidant approved by FDA / WHO. [0005] Direct esterification method prepares the ch...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/76
Inventor 张宗和黄嘉玲秦清徐浩李丙菊仲崇茂
Owner 南京龙源天然多酚合成厂
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