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A kind of preparation method of 4-tert-butylphthalaldehyde

A technology of tert-butyl phthalaldehyde and xylene, which is applied in the field of preparation of 4-tert-butyl phthalaldehyde, can solve the problems of only 78% yield, high reaction temperature, complicated catalyst preparation and the like

Active Publication Date: 2020-10-27
重庆奥舍生物化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The current public literature reports that 4-tert-butyl-phthalaldehyde is obtained by bromination and hydrolysis of 4-tert-butyl-o-xylene (1996, JP 08245478). To bromine, the cost is higher, and the yield is only 78%
The structure similar to it is the preparation of o-phthalaldehyde. Although there are many reports in the literature on the preparation method, there are few direct oxidation of o-xylene.
The patent with the publication number CN 106552622A discloses the preparation of o-phthalaldehyde by using o-xylene as a raw material, and the prepared V-Ag-Si-O catalyst catalyzes the oxidation of o-xylene to prepare o-phthalaldehyde with a yield of 73%. Because the reaction temperature is too high, the catalyst preparation is more complicated

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] Add 162 g (1.0 mol) of 4-tert-butyl-o-xylene and mixed catalyst (silver carbonate: copper acetylacetonate: manganese acetate: cobalt acetate: nickel acetate: ammonium molybdate: selenium dioxide=0.5:1: 1:1:1:1:1, molar ratio) 32.4g, heated to 150°C for reaction, after the reaction was completed, dichloromethane solvent was added, insoluble matter was filtered out, and dichloromethane was recovered by distillation to obtain 4-tert-butylphthalaldehyde 162 g, yield 85%, purity 98.5%.

Embodiment 2

[0013] Add 162 g (1.0 mol) of 4-tert-butyl-o-xylene and mixed catalyst (silver carbonate: copper acetylacetonate: manganese acetate: cobalt acetate: nickel acetate: ammonium molybdate: selenium dioxide = 1:1: 1:1:1:1:2, molar ratio) 81 g, heated to 200°C for reaction, after the reaction was completed, dichloromethane solvent was added, insoluble matter was filtered out, and dichloromethane was recovered by distillation to obtain 4-tert-butylphthalaldehyde 152 g, yield 80%, purity 98.0%.

Embodiment 3

[0015] Add 162 g (1.0 mol) of 4-tert-butyl-o-xylene and mixed catalyst (silver carbonate: copper acetylacetonate: manganese acetate: cobalt acetate: nickel acetate: ammonium molybdate: selenium dioxide=0.8:1: 1:1:1:1:1.5, molar ratio) 45g, heated to 180°C for reaction, after the reaction was completed, dichloromethane solvent was added, insoluble matter was filtered out, and dichloromethane was recovered by distillation to obtain 4-tert-butylphthalaldehyde 165 g, yield 87%, purity 99.0%.

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Abstract

The invention discloses a preparation method of 4-tertiary butyl o-phthalaldehyde, and belongs to the field of organic synthesis. The technical scheme includes that the preparation method includes thesteps: taking the 4-tertiary butyl o-phthalaldehyde as a starting raw material; taking mixture of silver carbonate, copper acetylacetonate, manganese acetate, cobalt acetate, nickel acetate, ammoniummolybdate and selenium dioxide as a mixed catalyst; taking air as an oxidizing agent; reacting raw materials at the temperature of 150-200 DEG C to prepare the 4-tertiary butyl o-phthalaldehyde. Thepreparation method is mild in reaction condition, high in yield, low in cost and suitable for industrial production, and the synthesis method has industrial production values.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 4-tert-butylphthalaldehyde. Background technique [0002] Aldehyde group is an important functional group in organic chemistry. Aldehyde group can undergo many transformations, such as reduction of aldehyde group to obtain alcohol, oxidation to obtain acid, and dehydration after hydroxylamination to convert to cyano group. In the modern chemical industry, catalytic oxidation is one of the main technologies in organic synthesis and production, and it is also a key technology to promote my country's economic development. However, there are still some defects and deficiencies in the technologies currently used, which limit the application of these technologies in industrial production. There are many ways to prepare aldehyde groups, among which the method of selective oxidation of hydrocarbons to produce aldehydes is the most difficult ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/36C07C47/544
CPCC07C45/36C07C47/544
Inventor 崔振伟
Owner 重庆奥舍生物化工有限公司
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