Method for preparing anisaldehyde by using natural anethole as raw material

A technology of anethole and anisaldehyde, which is applied in the field of synthetic fragrances, can solve the problems of difficulty in industrialized production, environmental pollution, and troublesome preparation, and achieves the effects of improved compatibility, environmental friendliness, and low production cost.

Active Publication Date: 2014-05-28
NANCHANG HANGKONG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation of anisaldehyde by ozonation is a method that has been studied more in the past 30 years. Ozone has the characteristics of strong oxidizing power, good selectivity and fast reaction speed. Anethole is an unsaturated olefin with a benzene ring. Ozone can Bonds are oxidized and will not attack the benzene ring, but it is polluting to the environment, and it is cumbersome to prepare, requires a large amount of ozone, and is difficult to realize industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] (1) Mix 30 g of natural anethole, 160 g of ethanol, and 80 g of water to obtain the reaction raw materials; add the reaction raw materials into a 500 mL three-necked flask, and control the reaction temperature at 40°C. The flow rate of 0.1m3 / h is fed with oxygen, and the reaction is carried out for 40 minutes to obtain a mixed solution of anisaldehyde, ethanol and water;

[0015] (2) Separate the mixed liquid, take the upper liquid and distill off the organic solvent to obtain the crude anisaldehyde, extract the lower liquid with ethyl acetate, take the extract and distill the crude anisaldehyde, combine the crude anisaldehyde; rectify the crude product to obtain the anisaldehyde product . The content of anisaldehyde detected by GC was 99.0%, and the yield was 70.5% based on anisaldehyde.

Embodiment 2

[0017] (1) Mix 40 g of natural anethole, 220 g of ethanol, and 90 g of water to obtain the reaction raw materials; add the reaction raw materials into a 500 mL three-neck flask, control the reaction temperature at 45 °C, and use natural anethole per kilogram of reaction raw materials The flow rate of 0.2m3 / h is passed into oxygen, and the reaction is carried out for 50 minutes to obtain a mixed solution containing anisaldehyde, ethanol and water;

[0018] (2) Separate the mixed liquid, take the upper liquid and distill off the organic solvent to obtain the crude anisaldehyde, extract the lower liquid with ethyl acetate, take the extract and distill the crude anisaldehyde, combine the crude anisaldehyde; rectify the crude product to obtain the anisaldehyde product . The content of anisaldehyde detected by GC was 99.2%, and the yield was 72.7% based on anisaldehyde.

Embodiment 3

[0020] (1) Mix 50 g of natural anethole, 270 g of ethanol, and 80 g of water to obtain the reaction raw materials; add the reaction raw materials into a 500 mL three-neck flask, control the reaction temperature at 52 ° C, and use 0.3 g of natural anethole per kilogram of reaction raw materials The flow rate of m3 / h is fed into oxygen, and the reaction is carried out for 60 minutes to obtain a mixed solution containing anisaldehyde, ethanol and water;

[0021] (2) Separate the mixed liquid, take the upper liquid and distill off the organic solvent to obtain the crude anisaldehyde, extract the lower liquid with ethyl acetate, take the extract and distill the crude anisaldehyde, combine the crude anisaldehyde; rectify the crude product to obtain the anisaldehyde product . The content of anisaldehyde detected by GC is 99.4%, and the yield is 73.9% based on anisaldehyde

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Abstract

A method for preparing anisaldehyde by using natural anethole as a raw material comprises the following steps: 1, mixing natural anethole, ethanol and water to obtain a reaction raw material, adding the reaction raw material into a three-neck bottle, letting in a certain volume of oxygen, and carrying out an oxidation reaction to obtain a reaction product containing anisaldehyde; and 2, carrying out liquid separation treatment of a mixed solution, taking the obtained upper layer liquid, distilling the upper layer liquid to remove an organic solvent in order to obtain crude anisaldehyde, extracting the obtained lower layer liquid by an organic solvent, distilling the obtained extract liquid to obtain crude anisaldehyde, mixing the above obtained two groups of crude anisaldehyde, and rectifying the above obtained crude anisaldehyde mixture to obtain anisaldehyde. The method lays an environmentally friendly foundation for producing anisaldehyde.

Description

[0001] technical field [0002] The invention belongs to the field of synthetic perfumes, in particular to a method for preparing anisaldehyde by one-step oxidation of natural anethole using ethanol and water as solvents. Background technique [0003] Anisaldehyde (anisaldehyde; p-methoxybezaldehyde; aubepine) chemical name: p-methoxybenzaldehyde. Colorless or light yellow liquid, it can solidify when cooled. Relative density 1.119-1.123, refractive index 1.5710-1.5750, boiling point 246-248°C, melting point 1-2.5°C, flash point above 100°C, soluble in 2 volumes of 60% ethanol, miscible with oily spices, acid value <6.0 . Anisaldehyde has an anise-like aroma, like hawthorn flowers, and some bean aromas like vanilla beans, and some herbs, spicy and sweet, and the aroma is strong and long-lasting. [0004] Anisaldehyde is produced by oxidation of natural anethole. Anethole oxidation methods are mainly divided into three categories: traditional oxidation method, electro-...

Claims

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Application Information

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IPC IPC(8): C07C47/575C07C45/36
CPCC07C45/36C07C47/575
Inventor 谢宇潘建飞张秋根张二欢曾繁山凌云
Owner NANCHANG HANGKONG UNIVERSITY
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