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Method for preparing methyl hesperidin

A technology of methyl hesperidin and hesperidin, applied in the field of preparation of methyl hesperidin, can solve the problems of increased difficulty in disposal of three wastes, high cost of distillation solvent, increased solvent consumption, etc., so as to avoid treatment and reduce consumption. , the effect of improving yield

Inactive Publication Date: 2018-06-08
HANDAN ZHAODU FINE CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, this method needs to consume much more than the theoretical amount of dimethyl sulfate due to the reaction of dimethyl sulfate and water, which also correspondingly requires an additional large amount of alkali to neutralize the hydrolyzed dimethyl sulfate, which will inevitably lead to low raw material utilization. The difficulty of disposal of the three wastes has increased
In the separation stage of the reaction, limited by the solubility of the product, n-butanol can only be used as the extraction agent, and a large number of solvent extractions are required, which greatly increases the amount of solvent used, and the cost of distilling the solvent in the later stage is also very high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Add 10 L of anhydrous methanol, 200 g of sodium hydroxide, and 1.5 kg of hesperidin into a 20 L reactor, stir and dissolve at room temperature, then add 500 g of methyl trifluoromethanesulfonate dropwise for 1 hour. After stirring at room temperature for 6 hours, hydrogen chloride gas was introduced until the pH value in the system was 4 to 5, and the amount of hydrogen chloride gas introduced at this time was 85 grams. After continuing to stir for 1 hour, it was filtered, and the solvent was distilled off from the filtrate under reduced pressure to obtain a brown blocky solid. Dissolve the solid in 5L of ethanol, stir for 1 hour, make the insoluble matter completely become a loose suspension, filter, the filter cake is a yellow solid, and vacuum dry to obtain 1.34 kg of product with a purity of 95.7%, a combustion residue of 0.2%, and a yield of 87.4%. The filtrate was distilled under reduced pressure to a volume of 1 L, and 423 grams of white crystals of potassium tr...

Embodiment 2

[0023] Add 8L of DMF, 250g of potassium hydroxide, and 1.8kg of hesperidin into a 20L reactor, stir and dissolve at room temperature, then add 600g of methyl trifluoromethanesulfonate dropwise for 1 hour. After stirring at room temperature for 8 hours, add glacial acetic acid to acidify until the pH value in the system is 4~5, and the amount of glacial acetic acid added at this time is 164 grams. After continuing to stir for 1 hour, it was filtered, and the solvent was distilled off from the filtrate under reduced pressure to obtain a brown blocky solid. Dissolve this solid in 8L acetone, stir for 1 hour, make the insoluble matter completely become loose suspended matter, filter, the filter cake is a yellow solid, vacuum dry to obtain 1.66 kg of product, purity 94.8%, combustion residue 0.3%, yield 90.7%. The filtrate was distilled under reduced pressure to a volume of 2 L, and 567 g of white crystals of potassium trifluoromethanesulfonate were precipitated by cooling.

Embodiment 3

[0025] Add 10L of anhydrous tert-butanol, 425 grams of potassium tert-butoxide, and 1.5 kg of hesperidin into a 20L reactor. After stirring and dissolving at room temperature, add 480 grams of methyl trifluoromethanesulfonate dropwise for 1 hour. After stirring at room temperature for 7 hours, hydrogen chloride gas was introduced until the pH value in the system was 4 to 5. At this time, the amount of hydrogen chloride gas introduced was 44 grams. After continuing to stir for 1 hour, it was filtered, and the solvent was distilled off from the filtrate under reduced pressure to obtain a brown blocky solid. This solid was dissolved in 6.5L of acetonitrile, stirred for 1 hour, the insoluble matter was completely turned into a loose suspension, filtered, the filter cake was a yellow solid, and vacuum-dried to obtain 1.41 kg of product with a purity of 94.9% and a combustion residue of 0.2%. The rate is 92.0%. The filtrate was distilled under reduced pressure to a volume of 2.2 L,...

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Abstract

The invention provides a method for preparing methyl hesperidin. The method comprises the following steps: enabling hesperidin as a main raw material to react with trifluoro-methyl methanesulfonate inthe presence of an alkali, performing acidification, filtration and desolvation, further washing with an organic solvent, and filtering, thereby obtaining the methyl hesperidin, wherein the purity ofthe methyl hesperidin is 95% or greater, and the yield of the methyl hesperidin is greater than 90%. The byproduct trifluoro-mesylate is a raw material for synthesizing trifluoromethanesulfonic acid.Compared with the prior art, the method for preparing the methyl hesperidin is safe in reaction process, simple and convenient to operate, efficient and environmental-friendly and applicable to industrial production.

Description

technical field [0001] The invention designs a preparation method of methyl hesperidin. Background technique [0002] Methyl hesperidin, chemical name: 3'-methyl-7-(rhamnose-L-glucose) hesperidin. It is a yellow or light yellow solid, easily soluble in water, slightly soluble in ethanol, acetone, insoluble in ether. It has a vitamin P-like effect and enhances the action of vitamin C. Commonly used in whitening cosmetic products, prevention and redness repair products, food additives, and nutritional supplements, etc. The common synthesis method of methyl hesperidin is to dissolve hesperidin in alkaline aqueous solution and methylate it with dimethyl sulfate to obtain methyl hesperidin. After extraction with n-butanol, the organic phase is desolvated and recrystallized with 95% ethanol to obtain the refined product. Because the product contains a small amount of n-butanol, it often has the odor of n-butanol. The yield of methyl hesperidin prepared by this method is low, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/07C07H1/00C07C309/06C07C303/32
CPCC07C303/32C07H1/00C07H17/07C07C309/06
Inventor 赵永平丁金囤王运红时建刚司小东
Owner HANDAN ZHAODU FINE CHEM CO LTD
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