Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

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
View PDF3 Cites 4 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 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%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D215/26
Inventor 李伟军林旭锋
Owner CHIZHOU WANWEI CHEM
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com