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Method for synthesizing alpha-methylcinnamaldehyde from phenylpropionaldehyde

A technology of methyl cinnamaldehyde and phenylpropionaldehyde, applied in chemical instruments and methods, preparation of organic compounds, preparation of carbon-based compounds, etc., can solve the problems of poor economic benefits, average yield, and high cost of phase transfer catalysts, etc. Achieve the effects of simple operation, improved selectivity, and good industrial application prospects

Active Publication Date: 2021-03-30
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] To sum up, the main synthesis method of α-methylcinnamaldehyde is the condensation of benzaldehyde and n-propionaldehyde. Since the water solubility of both is average, and benzaldehyde is prone to Cannizzaro reaction under the action of alkali catalyst, the yield is average.
At present, people have made many improvements to this synthetic route liquid, mainly adding phase transfer catalysts to increase the reaction yield, but phase transfer catalysts are expensive and have poor economic benefits.

Method used

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  • Method for synthesizing alpha-methylcinnamaldehyde from phenylpropionaldehyde
  • Method for synthesizing alpha-methylcinnamaldehyde from phenylpropionaldehyde

Examples

Experimental program
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Effect test

Embodiment 1

[0037] At room temperature, two 500mL autoclaves (effective volume: 430mL) were sealed and filled with 0.5MPa nitrogen gas to keep the pressure for 30min. The pressure in the autoclave did not decrease, which proved that the sealing was good. Fill and discharge nitrogen 3 times, 0.3MPa each time, and finally reduce the inside of the kettle to normal pressure. Turn on the external heat preservation of the autoclave, and when the internal temperature of the first kettle reaches 30°C and the internal temperature of the second kettle rises to 40°C, start to continuously feed phenylpropanal (2.85mL / min) and aqueous formaldehyde ( 37%, 1.8mL / min) and sodium hydroxide aqueous solution (10%, 0.16mL / min), the feed molar ratio is phenylpropionaldehyde: formaldehyde: sodium hydroxide = 100:110:2; while feeding, open 2 For the stirring of the two reactors, the two reactors all use turbine-type stirring paddles with a rotation speed of 600rpm to promote the mass transfer of water and oil t...

Embodiment 2

[0040]At room temperature, two 500mL autoclaves (effective volume: 430mL) were sealed and filled with 0.5MPa nitrogen gas to keep the pressure for 30min. The pressure in the autoclave did not decrease, which proved that the sealing was good. Fill and discharge nitrogen 3 times, 0.3MPa each time, and finally reduce the inside of the kettle to normal pressure. Turn on the external heat preservation of the autoclave, and when the internal temperature of the first kettle reaches 30°C and the internal temperature of the second kettle rises to 60°C, start to continuously feed phenylpropanal (5.49mL / min) and aqueous formaldehyde ( 37%, 3.75mL / min) and sodium hydroxide aqueous solution (20%, 0.13mL / min), the feed molar ratio is phenylpropionaldehyde: formaldehyde: sodium hydroxide = 100:120:2; while feeding, open 2 For the stirring of the two reactors, the two reactors all use turbine-type stirring paddles with a rotation speed of 600rpm to promote the mass transfer of water and oil t...

Embodiment 3

[0042] At room temperature, two 500mL autoclaves (effective volume: 430mL) were sealed and filled with 0.5MPa nitrogen gas to keep the pressure for 30min. The pressure in the autoclave did not decrease, which proved that the sealing was good. Fill and discharge nitrogen 3 times, 0.3MPa each time, and finally reduce the inside of the kettle to normal pressure. Turn on the external heat preservation of the autoclave, and when the internal temperature of the first kettle reaches 30°C and the internal temperature of the second kettle rises to 30°C, start to continuously feed phenylpropanal (2.06mL / min) and aqueous formaldehyde ( 37%, 1.4mL / min) and sodium hydroxide aqueous solution (5%, 0.12mL / min), the feed molar ratio is phenylpropionaldehyde: formaldehyde: sodium hydroxide = 100:120:1; while feeding, open 2 For the stirring of the two reactors, the two reactors all use turbine-type stirring paddles with a rotation speed of 600rpm to promote the mass transfer of water and oil tw...

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Abstract

The invention discloses a method for synthesizing alpha-methylcinnamaldehyde from phenylpropionaldehyde. The method comprises the following steps: 1) under the catalysis of alkali liquor, enabling phenylpropionaldehyde and an aqueous formaldehyde solution to pass through a continuous tank reactor, and conducting condensing to obtain a 2-benzylacrolein intermediate; and 2) carrying out hydroisomerization to obtain alpha-methylcinnamaldehyde. The raw materials, namely phenylpropionaldehyde and formaldehyde selected in the method are widely and readily available and low in price, so the method has a cost advantage; and the formaldehyde has good water solubility, the phenylpropionaldehyde is not easy to undergo the Cannizaro side reaction, and the intermediate prepared by condensation of the phenylpropionaldehyde and the phenylpropionaldehyde is easy to realize high yield.

Description

technical field [0001] The invention relates to a synthesis process, in particular to a method for synthesizing α-methylcinnamaldehyde from phenylpropionaldehyde. Background technique [0002] α-Methylcinnamaldehyde, also known as 2-methylcinnamaldehyde, is a yellow oily liquid with a cinnamon-like aroma and slightly sweet taste. It is widely used in cosmetics, soaps, food and other fields. In addition to being used as a spice, α-methylcinnamaldehyde is also an important pharmaceutical synthesis intermediate. [0003] At present, the main synthesis method of α-methylcinnamaldehyde is obtained by the condensation reaction of benzaldehyde and n-propionaldehyde, which is generally carried out in a water-oil two-phase manner with an aqueous alkali solution as a catalyst. Because the water solubility of benzaldehyde and n-propionaldehyde is all relatively poor, cause both can not contact with catalyzer well, not only reaction rate is slow, and reaction yield is also lower (gener...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/74C07C45/67C07C47/232
CPCC07C45/74C07C45/67C07C47/232Y02P20/584
Inventor 李雷益马文成黄文学陈江何光文
Owner WANHUA CHEM GRP CO LTD
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