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Synthesis method of p-isobutyl-beta-chloro-alpha-methyl allyl benzene aldehyde

A technology of methacrolein and a synthesis method, which is applied in the preparation of carbon-based compounds, chemical instruments and methods, and preparation of carbonyl compounds by condensation, etc., can solve the problems of high production cost, environmental pollution, large amount of waste water, etc. Control, high yield, and easy industrial-scale production effects

Inactive Publication Date: 2017-03-08
ANHUI HYEA AROMAS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The first is to use isobutylbenzene to react with methacrolein in the presence of a large amount of Lewis acid to prepare α-methyl-p-isobutylphenylpropionaldehyde in one step. The yield of this method is only 10%. Titanium chloride and boron trifluoride ether complex are used as reaction materials, and the amount of waste water produced after hydrolysis is huge, causing environmental pollution
[0008] The second is to use isobutylbenzene, butyric anhydride, and methacrolein to react under a large amount of trifluoroacetic acid, and then steam the mixture of isobutylbenzene+butyric acid+trifluoroacetic acid, and the reaction substance is alkaline hydrolyzed in methanol to obtain silver aldehyde , the production cost is too high due to the large use of very expensive trifluoroacetic acid and butyric anhydride

Method used

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  • Synthesis method of p-isobutyl-beta-chloro-alpha-methyl allyl benzene aldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] a) First add 140g of dichloroethane into a 500ml four-necked distillation flask, then put in 60g of aluminum trichloride, turn on the magnetic stirrer and constant temperature water bath, and cool down to -5±5°C;

[0045] b) Add 40 g of propionyl chloride dropwise to the distillation flask through the drop pump, control the drop time for 4 hours, control the reaction temperature to -5±5°C, and continue stirring for 0.5 h after the dropwise addition;

[0046] c) Continue to keep the temperature at -5±5°C, add 55g of isobutylbenzene dropwise through the dropping pump, and control the dropping time at 2h. After the dropping, raise the temperature to 20-30°C, and continue stirring for 0.5h;

[0047] d) Sampling detection, when the content of isobutylbenzene is ≤0.5%, reduce the temperature of the reaction system to -15~-10°C, increase the stirring rate, slowly add 175g of clear water for extraction, terminate the reaction, during the extraction process, control Reactor temper...

Embodiment 2

[0059] a) First add 700g of dichloroethane into a 2500ml four-necked distillation flask, then put in 300g of aluminum trichloride, turn on the magnetic stirrer and constant temperature water bath, and cool down to -5±5°C;

[0060] b) Add 200 g of propionyl chloride dropwise to the distillation flask through the drop pump, control the drop time for 6 hours, control the reaction temperature at -5±5°C, and continue stirring for 1 hour after the dropwise addition;

[0061] c) Continue to keep the temperature at -5±5°C, add 275g of isobutylbenzene dropwise through the dropping pump, control the dropping time at 2h, raise the temperature to 20-30°C after the dropping, and continue stirring for 1h;

[0062] d) Sampling and detection, when the content of isobutylbenzene is ≤0.5%, reduce the temperature of the reaction system to -15~-10°C, increase the stirring rate, slowly add 900g of clear water for extraction, terminate the reaction, and control Reactor temperature <40°C;

[0063] ...

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Abstract

The invention discloses a synthesis method of p-isobutyl-beta-chloro-alpha-methyl allyl benzene aldehyde and relates to the technical field of fine chemical engineering. The synthesis method includes: using isobutylbenzene and propionyl chloride as raw materials, and generating p-isobutyl propiophenone through acylation reaction; enabling p-isobutyl propiophenone to be in acylation reaction with phosphorus oxychloride to obtain a silver aldehyde precursor- p-isobutyl-beta-chloro-alpha-methyl allyl benzene aldehyde. The synthesis method is easy-to-get in raw materials, high in yield and convenient for industrial large-scale production; content of byproducts-ortho- and meta-isobutyl-beta-chloro-alpha-methyl allyl benzene aldehyde is controlled below 0.2%, and impurity content in a final silver aldehyde product prepared after hydrodechlorination is controlled effectively, so that flavoring requirements of essence and flavor are met.

Description

[0001] Technical field: [0002] The invention relates to the technical field of fine chemicals, in particular to a method for synthesizing p-isobutyl-β-chloro-α-methylphenylacrylaldehyde. [0003] Background technique: [0004] Silver aldehyde is one of the aromatic lily-of-the-valley fragrances, which has not been reported in nature. Silver aldehyde has a strong, lively lily-of-the-valley aroma, with a slight orange undertone and a fresh aldehyde scent. The chemical name of silver aldehyde is 2-methyl-3(4-(2-methylpropyl)phenyl) propanal, it is colorless to light yellow liquid, CAS No. 6658-48-6, EINECS No. 229-695- 0, soluble in ethanol and most organic solvents, insoluble in glycerin and water, almost insoluble in propylene glycol, relatively stable in alkaline solution, so it is similar to other lily-of-the-valley synthetic fragrances when used, suitable for high-end daily In the fragrance formula, it is used in beauty care, soap, laundry care and other household product...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/45C07C47/24
CPCC07C45/46C07C45/455C07C49/76C07C47/24
Inventor 王天义汪洋张政汪炎吴旭汪民富董金龙
Owner ANHUI HYEA AROMAS
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