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Preparation method of 8-hydroxyquinoline

A hydroxyquinoline and quinoline technology, applied in the field of preparation of 8-hydroxyquinoline, can solve the problems of high temperature, high pressure and strong alkali usage, high requirements for safe production, and high production costs, and achieves the reduction of dosage and waste liquid. Emissions, the effect of reducing equipment requirements

Inactive Publication Date: 2018-01-12
刘正信
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such process conditions undoubtedly have high requirements for equipment and safety in production, but in actual production, it is still inevitable to increase the risk and the production cost is high.
Compared with the reports in the existing domestic literature, the alkali fusion process also has the problems of high temperature and high pressure and the large amount of strong alkali used

Method used

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  • Preparation method of 8-hydroxyquinoline
  • Preparation method of 8-hydroxyquinoline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] First, put 250g of 65% fuming sulfuric acid into a 500ml three-necked flask, slowly add 100g of quinoline under stirring conditions, keep the temperature below 60℃, complete the addition within 3 hours, stir for another 30 minutes, slowly increase the temperature to After keeping at 120°C for 3 hours, cool to room temperature. The sulfonated liquid is slowly added to 400 g of ice water under stirring conditions, and after the dripping is completed, it is cooled to about 5° C., filtered, washed, and dried to obtain 140 g of 8-quinoline sulfonic acid.

[0044] Add 52g of 8-quinoline sulfonic acid obtained by the above method, 40g of water, 40g of sodium hydroxide and 5ml of catalyst methanol into the autoclave, seal and raise the temperature to 180℃, the pressure is 1.5MPa, carry out the alkali fusion reaction, and react for 7 hours Afterwards, the temperature was lowered to 60°C, the pressure was relieved, and 100ml of water was added to stir, then the reaction mixture was ...

Embodiment 2

[0046] First, put 300g of 65% fuming sulfuric acid into a 500ml three-necked flask. Under stirring conditions, slowly add 125g of quinoline, keep the temperature below 40℃, and complete the addition within 3 hours. After stirring for another 30 minutes, slowly heat up to After keeping at 115°C for 3 hours, cool to room temperature. The sulfonated liquid was slowly added to 425 g of ice water under stirring, and after the dripping was completed, it was cooled to about 5° C., filtered, washed, and dried to obtain 183 g of 8-quinoline sulfonic acid.

[0047] Add 52g of 8-quinoline sulfonic acid obtained by the above method, 60g of water, 57g of potassium hydroxide and 6ml of catalyst isopropanol into the autoclave, seal and raise the temperature to 170℃, the pressure is 1.4MPa, and carry out the alkali fusion reaction. After 7 hours, the temperature was lowered to 70°C, the pressure was relieved and 100ml of water was added to stir, then the reaction mixture was transferred to a 500...

Embodiment 3

[0049] First, put 300g of 65% fuming sulfuric acid into a 500ml three-necked flask. Under stirring conditions, slowly add 120g of quinoline, keep the temperature below 40℃, and complete the addition within 3 hours. After stirring for another 30 minutes, slowly increase the temperature to After holding at 110°C for 3 hours, cool to room temperature. The sulfonated liquid was slowly added to 425 g of ice water under stirring, and after the dripping was completed, it was cooled to about 5° C., filtered, washed, and dried to obtain 180 g of 8-quinoline sulfonic acid.

[0050] Add 52g of 8-quinoline sulfonic acid obtained by the above method, 50g of water, 40g of sodium hydroxide and 7ml of catalyst ethanol into the autoclave, seal and raise the temperature to 190℃, the pressure is 1.6MPa, carry out the alkali fusion reaction, and react for 8 hours Afterwards, the temperature was lowered to 70°C, the pressure was relieved, and 100ml of water was added to stir, then the reaction mixtur...

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Abstract

The invention relates to a preparation method of 8-hydroxyquinoline. The preparation method comprises the following steps: A), uniformly mixing quinoline and a sulfonating agent, performing a sulfonation reaction, and hydrolyzing to obtain a reaction solid and reaction liquid; B), under the action of a catalyst, heating the reaction solid obtained in the step A), water and inorganic strong alkali,and reacting to obtain the 8-hydroxyquinoline, wherein the catalyst is one or more of methanol, ethanol and isopropanol. By the preparation method, through addition of the catalyst during the reaction, the reaction temperature in an alkali-melting step in the production process of the 8-hydroxyquinoline is reduced, so that a requirement on equipment is reduced and the danger coefficient in actualproduction is also reduced, and thus a reaction condition is mild, operation is easy, and the purity and the yield are relatively high; meanwhile, through the addition of the catalyst, the using amount of the inorganic strong alkali is reduced, so that the production cost is reduced; in addition, the reaction liquid produced in the sulfonation reaction is recycled in a subsequent acidification process, so that discharge of waste liquid is reduced and clean production is achieved.

Description

Technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 8-hydroxyquinoline. Background technique [0002] 8-Hydroxyquinoline is an important organic synthesis intermediate. Its synthesis process, preparation of derivatives, and research on biological activity are currently one of the hot topics in chemistry, pharmacy, and medicine. As a metal ion chelating agent with excellent performance, 8-hydroxyquinoline has been widely used in chemical analysis of metal elements, extraction of metal ions, photometric analysis and metal anti-corrosion in the metallurgical industry and analytical chemistry. Since most of 8-hydroxyquinoline and its derivatives are biologically active, they are also widely used in the pharmaceutical industry. 8-Hydroxyquinoline is directly used as a disinfectant, and its halogenated derivatives, nitration and N-oxides are raw materials for the synthesis of drugs, and als...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/26
Inventor 刘正信宋江闯刘一筱戴安迪黄峰
Owner 刘正信
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