Synthetic method of anethole

A synthesis method and technology of anethole, which is applied in the field of preparation of spice compounds, can solve the problems of long negative pressure continuous dehydration reaction time, high side reactions of acylation reaction, and reduced safety factor, so as to reduce purification costs, have few side reactions, The effect of energy consumption reduction

Inactive Publication Date: 2013-04-24
HUAIAN WAN BANG SPICE IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] (1) The side reaction of the acylation reaction is high, and the product must be separated and purified before it can be used for hydrogenation reduction, so the yield is low and the energy consumption is high;
[0008] (2) Although the cost of using hydrogen for the reduction reaction is low, but because there are many polymers, the product must be separated and purified before being used for the dehydration reaction, resulting in low yield and high energy consumption, and at the same time, the safety factor is reduced due to the pressurized reaction;
[0009] (3) The reaction time of negative pressure continuous dehydration is long, the requirements for vacuum, steam and other equipment working conditions are high, and the energy consumption is high;

Method used

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  • Synthetic method of anethole
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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Under stirring state, drop into 118.8kg anisole and 133.5kgAlCl in the reactor 3 , lower the temperature to 5°C, add 92.5kg of propionyl chloride dropwise, control the temperature at 5°C to 10°C during the dropwise addition, and keep the temperature at 5°C to 10°C for 3 hours to complete the reaction, and neutralize with sodium hydroxide until neutral. The crude product of p-methoxypropiophenone was obtained, and the chromatographically effective amount was 148kg.

[0039] Add 14.8 kg of sodium borohydride to the above-mentioned crude product of p-methoxypropiophenone, control the temperature at 20°C to 30°C for the reduction reaction, end the reaction when the content of p-methoxypropiophenone is less than 0.5%, and neutralize with acetic acid to neutralize properties, the crude product of 1-(4-methoxyphenyl)-1-propanol was obtained, and the effective amount for chromatographic analysis was 147kg.

[0040] In above-mentioned 1-(4-methoxyphenyl)-1-propanol crude produc...

Embodiment 2

[0043] Under stirring state, drop into 129.6kg anisole and 133.5kgAlCl in the reactor 3 , lower the temperature to 5°C, add 92.5kg of propionyl chloride dropwise, control the temperature at 5°C to 10°C during the dropwise addition, and keep the temperature at 5°C to 10°C for 3 hours to complete the reaction, and neutralize with sodium hydroxide until neutral. The crude product of p-methoxypropiophenone was obtained, and the chromatographically effective amount was 149kg.

[0044] Put 22.4kg of sodium borohydride into the above-mentioned crude product of p-methoxypropiophenone, control the temperature at 20°C to 30°C for reduction reaction, end the reaction when the content of p-methoxypropiophenone is lower than 0.5%, and neutralize with acetic acid to neutralize properties, the crude product of 1-(4-methoxyphenyl)-1-propanol was obtained, and the effective amount for chromatographic analysis was 148kg.

[0045] In above-mentioned 1-(4-methoxyphenyl)-1-propanol crude product,...

Embodiment 3

[0048] Under stirring state, drop into 140.4kg anisole and 133.5kgAlCl in the reactor 3 , lower the temperature to 5°C, add 92.5kg of propionyl chloride dropwise, control the temperature at 5°C to 10°C during the dropwise addition, and keep the temperature at 5°C to 10°C for 3 hours to complete the reaction, and neutralize with sodium hydroxide until neutral. Obtain p-methoxypropiophenone crude product, the chromatographic analysis effective amount is 146kg.

[0049] Put 29.2kg of sodium borohydride into the crude p-methoxypropiophenone, control the temperature at 20°C to 30°C for reduction reaction, end the reaction when the content of p-methoxypropiophenone is less than 0.5%, neutralize with acetic acid to properties, the crude product of 1-(4-methoxyphenyl)-1-propanol was obtained, and the effective amount for chromatographic analysis was 145kg.

[0050] In above-mentioned 1-(4-methoxyphenyl)-1-propanol crude product, drop into 362.5kg methyl alcohol, 1.45kg p-toluenesulfoni...

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Abstract

The invention discloses a synthetic method of anethole. Anisole and propionyl chloride serve as starting raw materials, are subjected to a friedel-crafts acylation reaction, then are restored through sodium borohydride, and then are catalyzed and dehydrated through organic acid and acid inorganic salt, and finally the anethole is manufactured through rectification. Side reaction is low through the adoption of acylation and reduction, a middle body is not needed to be purified and can be directly put into the next reaction, purification loss and purification cost of the middle body are reduced, yield coefficient is improved, and energy consumption is reduced. A chemical reduction method is utilized to replace a catalytic hydrogenation method, selectivity is high, response speed is fast, side reactions are small in number, and reduction yield coefficient can reach above 98%. Double catalysts are adopted to carry out ordinary pressure low temperature dehydration in dissolvent with a low boiling point, and compared with a negative pressure continuous dehydration method, dehydration time can be shortened by 90%, and the energy consumption is greatly reduced. The total yield coefficient of the method can reach 75%. A product quality index is higher than that of a natural product standard.

Description

technical field [0001] The present invention relates to a kind of preparation method of fragrance compound, specifically relates to a kind of preparation method of anethole. Background technique [0002] Anethole (English name: Anethole), also known as anethole, anethole, p-propenylanisole, etc., is an aromatic compound widely present in nature, with the appearance of colorless or light yellow liquid or crystal, molecular formula C 10 h 12 O, the molecular weight is 148.2, the melting point is 22.5oC, the boiling point is 235oC, there are cis and trans isomers, the CAS number of the cis and trans anethole mixture is 104-46-1, and the trans anethole CAS number is 4180-23-8. Anethole is sweet and has a special aroma of fennel. Regardless of whether it is a natural product or a synthetic product, anethole exists in a mixed form of trans and cis, but the trans form is the main one. [0003] Anethole is favored by people because of its unique fennel smell, and is widely ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/215C07C41/18
Inventor 陈文抗
Owner HUAIAN WAN BANG SPICE IND CO LTD
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