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A kind of production method of ethyl vanillin glucoside

A technology of ethyl vanillin and glucoside, which is applied in the field of glycoside preparation, can solve the problems of large amount of catalyst, harsh reaction conditions, expensive catalyst, etc., and achieve the effect of easy-to-obtain raw materials, simple preparation process and high yield

Active Publication Date: 2019-03-19
重庆欣欣向荣精细化工股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Disadvantages: The reaction conditions are harsh, and strict anhydrous and light protection are required; the catalyst is more expensive, and the reaction steps are longer; heavy metal pollution, environmental protection pressure is high
[0009] Disadvantages: Haloglycosides are prone to elimination reactions; in most cases, the amount of the donor or acceptor in the reaction needs to be more than doubled, and the cost increases; the amount of catalyst is large, and it is not easy to recover; this method is not suitable for alkali-sensitive donors or acceptors. body glycosylation reaction

Method used

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  • A kind of production method of ethyl vanillin glucoside
  • A kind of production method of ethyl vanillin glucoside
  • A kind of production method of ethyl vanillin glucoside

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Embodiment 1

[0039] The present embodiment provides a kind of production method of ethyl vanillin glucoside, comprising the following production steps:

[0040] (1) Add a medium polar organic solvent in the reaction kettle and stir, the polarity of the medium polar organic solvent is 4.0, and the viscosity is 0.8;

[0041] (2) add bromotetraacetylglucose and ethyl vanillin in the reactor, the weight ratio of the bromotetraacetylglucose and ethylvanillin is 0.8;

[0042] (3) be heated up to between 35 ℃, then add basic catalyst;

[0043] (4) Continue to heat up to 60°C for reaction, keep the temperature constant for 2.5h;

[0044] (5) After the reaction finishes, remove the basic catalyst by filtration;

[0045] (6) the polar organic solvent in the filtration mother liquor is reclaimed by distillation;

[0046] (7) Using toluene and sodium hydroxide aqueous solution to carry out reflux treatment at 40 ° C, and keep the temperature for 30 minutes; the concentration of sodium hydroxide aqu...

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Abstract

The application discloses a production method of ethyl vanillin glucoside. The production method comprises the following production steps: (1) adding a solvent in a reaction vessel while performing stirring; (2) adding acetobromo-alpha-D-glucose and ethyl vanillin; (3) raising the temperature and adding a basic catalyst; (4) continuously carrying out the heating reaction; (5) performing filtration to remove the basic catalyst after the reaction is over; (6) recycling the moderate-polarity organic matter solvent; (7) performing reflux with toluene and a sodium hydroxide aqueous solution; (8) performing standing for layering to form an upper layer of a toluene solution and a lower layer of an aqueous phase containing impurities; (9) distilling the toluene solution, adding alcohol into the distilled residues, and performing filtering and washing to obtain ethyl vanillin tetra-acetyl glucoside; (10) adding methanol to the ethyl vanillin tetra-acetyl glucoside; and (11) performing filtering and drying to obtain white solid powder. The production method of ethyl vanillin glucoside is simple to operate, easy for industrial production, and high in yield.

Description

technical field [0001] The present invention relates to the preparation of a kind of glycoside (such as glycoside), in particular to a kind of production method of ethyl vanillin glucoside. Background technique [0002] The application of ethyl vanillin glucoside in cigarettes and baked foods can effectively improve the thermal stability of spices. At present, there are two main types of external-flavored cigarettes on the market: rose-flavored and biscuit-flavored, and the biscuit-flavored type has added ethyl vanillin. Ethyl vanillin is highly volatile, one is easy to be volatile and lost, and the other is easy to enter the mainstream smoke and cover up the natural tobacco aroma. Dube etc. cleverly utilized this property when making external-flavored cigarettes, reacted with glucose pentaacetate and HBr to obtain a-bromoglucose acetate, and this glucose tetraacetate was then reacted with ethyl vanillin React under weak base, and then deacetylate to obtain ethyl vanillin ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H1/00C07H15/203
CPCC07H1/00C07H15/203
Inventor 兰军季卫刚赵华文文泽平陈杰甘建强刘端唐凌
Owner 重庆欣欣向荣精细化工股份有限公司
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