Production technique of 8-hydroxyquinoline

A production process, the technology of hydroxyquinoline, applied in the direction of organic chemistry, etc., can solve the problems of low reaction yield, limited source, expensive price, etc., and achieve simple feeding and post-processing, safe and mild reaction conditions, and low equipment investment Effect

Inactive Publication Date: 2008-04-16
CHIZHOU WANWEI CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw material quinoline used in the quinoline method has limited sources and is expensive, and the yield of this two-step reaction is not high, and the pollution is large, so it is not recommended

Method used

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  • Production technique of 8-hydroxyquinoline
  • Production technique of 8-hydroxyquinoline
  • Production technique of 8-hydroxyquinoline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 1) Mix 1 mole of 2-N-p-toluenesulfonamidophenol, 0.02 mole of triethylamine, and 1000 ml of methanol and cool, then add 1.0 mole of acrolein dropwise at -20°C for 1 hour; , continue to stir and react at -20°C for 1 hour; then add hydrochloric acid, raise the temperature to 20°C and stir for 1 hour to generate N-p-toluenesulfonyl-8-hydroxyhydroquinoline intermediate;

[0025] 2) Add solid sodium hydroxide to the above solution, heat up and reflux for 1 hour, cool down, and then adjust the pH to 7.5 with hydrochloric acid;

[0026] 3) Add water to the above solution, heat up and carry out steam distillation to obtain 0.75 mole of high-purity 8-hydroxyquinoline; based on 2-N-p-toluenesulfonamidophenol, the molar yield is 75%.

Embodiment 2

[0028] 1) Mix 1 mole of 2-N-p-toluenesulfonamidophenol, 0.2 moles of triethylamine, and 1000 ml of methanol and cool, then add 1.6 moles of acrolein dropwise at -5°C for 10 hours; , continue to stir and react at -5°C for 5 hours; then add hydrochloric acid, heat up to 50°C and stir for 5 hours to generate N-p-toluenesulfonyl-8-hydroxyhydroquinoline intermediate;

[0029] 2) Add solid sodium hydroxide to the above solution, heat up and reflux for 5 hours, then cool down, then adjust the pH to 8.5 with hydrochloric acid;

[0030] 3) Add water to the above solution, heat up and carry out steam distillation to obtain 0.80 mole of high-purity 8-hydroxyquinoline; based on 2-N-p-toluenesulfonamidophenol, the molar yield is 80%.

Embodiment 3

[0032] 1) Mix 1 mole of 2-N-p-toluenesulfonamidophenol, 0.05 mole of triethylamine, and 1000 ml of methanol and cool, then add 1.2 moles of acrolein dropwise at -10°C for 5 hours; , continue to stir and react at -20°C for 3 hours; then add hydrochloric acid, heat up to 30°C and stir for 3 hours to generate N-p-toluenesulfonyl-8-hydroxyhydroquinoline intermediate;

[0033] 2) Add solid sodium hydroxide to the above solution, heat up and reflux for 3 hours, cool down, and then adjust the pH to 8.0 with hydrochloric acid;

[0034] 3) Add water to the above solution, heat up and carry out steam distillation to obtain 0.85 mole of high-purity 8-hydroxyquinoline; based on 2-N-p-toluenesulfonamidophenol, the molar yield is 85%.

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Abstract

The present invention discloses a production technics for a 8-hydroxide quinoline, which includes the following synthetic procedures that: firstly 2-N- p-toluenesulfonyl amino phenol is mixed with ethylamine and methanol, cooled, and dripped with acrolein, after dripping, the mixture is stirred continuously for reaction, then added with hydrochloric acid, stirred for reaction under raised temperature to produce an intermediate of p-toluenesulfonyl-8-hydroxide hydrogenated quinoline, secondly, the solution as above is added with solid sodium hydroxide, the temperature of the mixed solution is raised, and then undergoes circumfluence cooling down, then hydrochloric acid is used to regulate the pH=7.5-7.8 and, thirdly, water is added into the solution as above, temperature is raised and water steam distillation is carried out to obtain the high-purity 8-hydroxide quinoline. Compared with the preparation method in the prior art, the present invention has simple operation, economized investment on the equipment, high yields, low fabrication cost, and suitability for industrialized fabrication. The actual molecular yield of 8-hydroxide can reach to more than 85 percent of that of 8-hydroxyl quinoline, based on the amount of 2-N- p-toluenesulfonyl amino phenol.

Description

technical field [0001] The invention relates to a production process of quinoline, in particular to a production process of 8-hydroxyquinoline. Background technique [0002] It is well known that the preparation of 8-hydroxyquinoline is mainly obtained by the Skraup reaction of o-aminophenol, o-nitrophenol and glycerol under the action of concentrated sulfuric acid, such as the records in P 175-177 of the textbook "Organic Chemistry Experiment" edited by Zeng Zhaoqiong. The reaction temperature of this method is high, the reaction is violent, and anhydrous glycerin is obtained in a large excess, the amount of by-product polymer is large, and the product separation and purification are difficult. The reaction formula is as follows: [0003] [0004] It is also reported in the literature that sulfuric acid or hydrochloric acid is used to catalyze the reaction of o-aminophenol, o-nitrophenol and acrolein to prepare 8-hydroxyquinoline, such as DE2545704, JP48012745, US4044011...

Claims

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Application Information

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IPC IPC(8): C07D215/26
Inventor 李伟军林旭锋
Owner CHIZHOU WANWEI CHEM
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