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Improved beta-arbutin preparation method

A technology of arbutin and high boiling point, which is applied in the preparation of sugar derivatives, chemical instruments and methods, organic chemistry, etc., can solve the problems of increasing raw material consumption and production costs, reduce the treatment of three wastes, increase the yield, and save consumption Effect

Active Publication Date: 2014-01-22
HUBEI ARTEC CARBOHYDRATE CHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Thereby greatly increasing the consumption of raw materials and production costs

Method used

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  • Improved beta-arbutin preparation method

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Effect test

example 1

[0022] The mixture of 30 grams of glucose, 100 milliliters of acetic anhydride, 5 grams of sodium acetate and 100 milliliters of dimethylformamide was reacted at 100 ° C for 3 hours under stirring conditions, and the reaction solution was cooled to room temperature, and 100 milliliters of toluene was added, and mixed well , standing for layering, extracting the dimethylformamide layer with 100 milliliters of toluene again, combining the toluene layers, washing the toluene layer with 100 milliliters of water, after azeotropic dehydration, adding 15 grams of phenol p-glycolate, and reacting Liquid temperature is cooled to 5 ℃, and 50 milliliters of boron trifluoride diethyl ethers are added dropwise, and after normal temperature reaction for 4 hours, 200 milliliters of ice waters are added to the reaction liquid, after layering, the aqueous phase is extracted twice with 400 milliliters of toluene again, and the combined The toluene layer was washed with water, concentrated, and r...

example 2

[0024]The mixture of 30 grams of glucose, 100 milliliters of acetic anhydride, 5 grams of sodium acetate and 100 milliliters of dimethyl sulfoxide was reacted at 110 ° C for 2 hours under stirring conditions, and the reaction solution was cooled to room temperature, extracted three times with 300 milliliters of toluene, Combine the toluene layers, wash the toluene layer with 100 ml of water, after azeotropic dehydration, add 15 grams of phenol p-glycolate, cool the temperature of the reaction solution to 5 ° C, add dropwise 50 ml of boron trifluoride ether, and then react at room temperature After 4 hours, 200 milliliters of ice water was added to the reaction solution, and the water phase was extracted twice with 400 milliliters of toluene after the layers were separated. The combined toluene layers were washed with water, concentrated, and recrystallized with methanol to obtain 63 grams of needle-like crystals. Calculate, total recovery is 79%. Recording crystal fusing point...

example 3

[0026] The mixture of 10 grams of glucose, 35 milliliters of acetic anhydride, 2 grams of sodium acetate and 50 milliliters of dimethylformamide was reacted at 100° C. for 3 hours under stirring conditions, and the reaction solution was cooled to room temperature, extracted three times with 150 milliliters of toluene, The toluene layers were combined, and the dimethylformamide layer was azeotropically distilled with toluene to remove acetic acid, then added 10 grams of glucose and 26 milliliters of acetic anhydride, and reacted at 100° C. for 3 hours under stirring conditions. After the reaction solution was cooled to room temperature, Extract three times with 150 ml of toluene, and combine the toluene. After repeating this operation five times, all the toluene layers were combined to about 750 ml. Wash with 300 milliliters of water, after azeotropic dehydration treatment, add 25 grams of phenol p-hydroxyacetate, cool the temperature of the reaction solution to 5° C., add drop...

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Abstract

The invention provides an improved environment-friendly beta-arbutin synthetic process which comprises the following steps of reacting glucose with acetic anhydride in the presence of sodium acetate in a high-boiling point polar aprotic solvent; after the reaction is finished, extracting by using a low-polarity aprotic solvent, wherein low-polarity aprotic solvent extract liquor is subjected to washing and dewatering treatment and then is directly used for glycosylation reaction with p-hydroxy phenyl acetate; carrying out azeotropic distillation on the raffinate of the high-boiling point polar aprotic solvent to remove acetic acid generated in the reaction, and then complementing the glucose and the acetic anhydride to further carry out the reaction of the next batch of penta-acetyl glucose synthesis. Compared with the traditional process, the new process provided by the invention omits the penta-acetyl glucose purifying procedure and omits the three-waste treatment of a penta-acetyl glucose synthesizing procedure, thereby greatly reducing the raw material cost and increasing the total yield of beta-arbutin.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and relates to a preparation method of β-arbutin, in particular to an improved preparation process of β-arbutin. Background technique [0002] Arbutin (4-hydroxyphenyl-β-D-glucopyranoside) was originally a natural active substance isolated from medicinal plants such as bearberry leaves. In addition to various medical applications, it is widely used in whitening cosmetics as a green, reliable and efficient skin whitening aid. Its whitening mechanism is that it can effectively inhibit the production of melanin by human tyrosinase. In addition to extracting from natural plants, there are mainly two ways to prepare arbutin: biological enzyme synthesis and organic synthesis. At present, arbutin prepared through organic synthesis has been widely used in the market. The structural formula of arbutin is shown in the following formula: [0003] [0004] The chemical synthesis of arbutin uses glucose as...

Claims

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Application Information

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IPC IPC(8): C07H15/203C07H1/00
Inventor 董海丁圣峰
Owner HUBEI ARTEC CARBOHYDRATE CHEM
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