The synthetic method of 2-methyl-3-hydroxyquinoline and the preparation method of quinone ketone disperse dye

The technology of a kind of hydroxyquinoline and synthetic method is applied in the preparation of quinone disperse dyes and the synthesis field of 2-methyl-3-hydroxyquinoline, which can solve the problem of increasing the preparation cost of quinone disperse dyes and reducing the 2- Methyl-3-hydroxyquinoline yield, instability and other issues

Active Publication Date: 2022-05-20
HUNAN NORCHEM PHARMACEUTICAL CO LTD
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Problems solved by technology

However, due to the instability of anthranilaldehyde and chloroacetone itself, a certain degree of side reactions will be accompanied in the ring-forming reaction process, which will reduce the yield of 2-methyl-3-hydroxyquinoline and increase the yield of quinoline Preparation cost of ketone disperse dyes

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  • The synthetic method of 2-methyl-3-hydroxyquinoline and the preparation method of quinone ketone disperse dye
  • The synthetic method of 2-methyl-3-hydroxyquinoline and the preparation method of quinone ketone disperse dye
  • The synthetic method of 2-methyl-3-hydroxyquinoline and the preparation method of quinone ketone disperse dye

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preparation example Construction

[0037] One embodiment of the present invention provides a synthesis method of 2-methyl-3-hydroxyquinoline, comprising the following steps S10-S20.

[0038] Step S10, mixing anthranilaldehyde, chloroacetone, base catalyst, phase transfer catalyst and solvent, and adjusting the pH value to 11-13 to obtain a mixed solution.

[0039] First, anthranilaldehyde, chloroacetone, alkali catalyst, phase transfer catalyst and solvent are mixed, and under the action of the phase transfer catalyst, all raw materials are fully contacted to obtain a homogeneously mixed solution, thereby improving the efficiency of subsequent reactions.

[0040] The technicians of the present invention have found through in-depth research: although o-aminobenzaldehyde and chloroacetone pass through the microchannel reaction under the effect of an alkali catalyst, the ring-forming reaction can occur rapidly to obtain 2-methyl-3-hydroxyquinoline; yet, During the microchannel reaction process, the reactivity of o...

Embodiment 1

[0089] 1) Anthranilaldehyde, chloroacetone and tetrabutylammonium bromide are dissolved in tetrahydrofuran to form a first solution; sodium hydroxide and zinc oxide are dissolved in water to form a second solution. The first solution and the second solution are then mixed to obtain a mixed solution. Wherein, the mass ratio of o-aminobenzaldehyde, chloroacetone, tetrabutylammonium bromide, sodium hydroxide and zinc oxide in the mixed solution is: 1:0.6:0.1:0.6:0.08. The pH value of the mixed solution = 12.1.

[0090] 2) Pump the mixed solution obtained in step 1) into a preheater to preheat to 30°C to obtain a preheated reaction solution; then pump the preheated reaction solution into a microchannel reactor, and keep warm at 30°C for reaction, wherein The flow rate of the mixed solution is 50mL / min; the product obtained by the reaction enters the separation tank for separation treatment to obtain 2-methyl-3-hydroxy-quinoline.

[0091] 3) Calculate the yield of 2-methyl-3-hydr...

Embodiment 2

[0095] 1) Dissolving o-aminobenzaldehyde, chloroacetone and tetrabutylammonium bromide in tetrahydrofuran to form a first solution; dissolving sodium hydroxide and zinc oxide in water to form a second solution. The first solution and the second solution are then mixed to obtain a mixed solution. Wherein, the mass ratio of o-aminobenzaldehyde, chloroacetone, tetrabutylammonium bromide, sodium hydroxide and zinc oxide in the mixed solution is: 1:0.6:0.2:0.9:0.08. The pH value of the mixed solution = 12.8.

[0096] 2) Pump the mixed solution obtained in step 1) into a preheater to preheat to 30°C to obtain a preheated reaction solution; then pump the preheated reaction solution into a microchannel reactor, and keep warm at 30°C for reaction, wherein The flow rate of the mixed solution is 50mL / min; the product obtained by the reaction enters the separation tank for separation treatment to obtain 2-methyl-3-hydroxy-quinoline.

[0097] 3) Calculate the yield of 2-methyl-3-hydroxyl...

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Abstract

The present invention relates to a kind of synthetic method of 2-methyl-3-hydroxyquinoline and the preparation method of quinone disperse dye; in the synthetic method of 2-methyl-3-hydroxyquinoline, first anthranil , chloroacetone, alkali catalyst, phase transfer catalyst and solvent are mixed, and the pH value is adjusted to 11-13. Under the action of the phase transfer catalyst, each raw material is fully contacted to obtain a uniformly mixed homogeneous mixed solution with a specific pH value; Then the mixed solution is subjected to a microchannel reaction. During the microchannel reaction, the reaction materials in the mixed solution can undergo micron or millimeter level micro-contact reactions, which improves the reaction speed and reaction selectivity, and reduces the amount of ortho-amino groups in the microchannel reaction process. The possibility of benzaldehyde or chloroacetone undergoing self-condensation, thereby improving the yield of 2-methyl-3-hydroxyquinoline.

Description

technical field [0001] The invention relates to the technical field of synthesis of quinone disperse dyes, in particular to a synthesis method of 2-methyl-3-hydroxyquinoline and a preparation method of quinone disperse dyes. Background technique [0002] With the development of society, people pay more and more attention to environmental protection issues. In the dye technology industry, the concept of "green dyes" has been proposed in recent years, while traditional azo-type disperse dyes have been gradually eliminated due to their carcinogenic effects; some disperse dyes synthesized from aromatic amines are harmful to human body or their production The preparation is not conducive to environmental protection and has been banned. Technologists have been working on developing green dyes. [0003] Quinone-based disperse dyes are a kind of superior light yellow disperse dyes with excellent performance, not only bright color, but also light fastness up to 6-7 grades, good col...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/20C09B57/00C09B67/38
CPCC07D215/20C09B57/00C09B67/008Y02P20/584
Inventor 曾春玲刘喜荣靳志忠孟浩
Owner HUNAN NORCHEM PHARMACEUTICAL CO LTD
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