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

Method of synthesis of N-alkyl p-toluene sulfonamide

A technology for p-toluenesulfonamide and p-toluenesulfonic acid, which is applied in the field of synthesizing N-alkyl p-toluenesulfonamide, can solve the problems of low catalyst reaction efficiency, difficult recycling, large environmental pollution, etc., and achieves high thermal stability and chemical stability. Stability, lower production cost, simple separation effect

Inactive Publication Date: 2017-04-19
南安创友日化有限公司
View PDF4 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The technical problem to be solved by the present invention is the problems of low catalyst reaction efficiency, difficult recycling, large environmental pollution, and high corrosiveness in the process of preparing N-alkyl p-toluenesulfonamides from anhydrous p-toluenesulfonic acid in the prior art. A kind of method that anhydrous p-toluenesulfonic acid synthesizes N-alkyl p-toluenesulfonamide

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Dissolve 3.5 g of anhydrous p-toluenesulfonic acid in 20 g of dichloromethane, add 0.20 g of catalyst SO 4 2- / PIM-1 (the molar ratio of covalent groups to ligands is 0.1), 4.5g 5A type molecular sieve, uniformly stirred at 20°C for 0.5h, and then added 2.2g n-butylamine. After keeping at 20°C for 6 hours, remove the molecular sieve and catalyst by filtration, and wash the filtrate once with 10 mL of 0.5 mol / L hydrochloric acid solution and 10 mL of 0.5 mol / L sodium hydroxide solution. After the organic phase was dried with anhydrous sodium sulfate, the desiccant was removed, the solvent dichloromethane was recovered by distillation, and the crude product of N-butyl-p-toluenesulfonamide was obtained. After the crude product was washed with 50% ethanol aqueous solution, 2.96 g of the product was obtained by drying. According to detection and analysis, the conversion rate of anhydrous p-toluenesulfonic acid can reach 79.91%, and the yield of N-butyl p-toluenesulfonamide ...

Embodiment 2

[0018] Dissolve 3.5 g of anhydrous p-toluenesulfonic acid in 20 g of dichloromethane, add 0.20 g of catalyst SO 4 2- / PIM-1 (the molar ratio of covalent group to ligand is 0.1), 4.5g 5A type molecular sieve, stirred uniformly at 20°C for 0.5h, and then added 2.2g n-propylamine. After keeping at 20°C for 6 hours, remove the molecular sieve and catalyst by filtration, and wash the filtrate once with 10 mL of 0.5 mol / L hydrochloric acid solution and 10 mL of 0.5 mol / L sodium hydroxide solution. After the organic phase was dried with anhydrous sodium sulfate, the desiccant was removed, the solvent dichloromethane was recovered by distillation, and the crude product of N-propyl p-toluenesulfonamide was obtained. After the crude product was washed with 50% ethanol aqueous solution, 3.10 g of the product was obtained by drying. According to detection and analysis, the conversion rate of anhydrous p-toluenesulfonic acid can reach 80.70%, and the yield of N-propyl p-toluenesulfonamide...

Embodiment 3

[0020] Dissolve 3.5 g of anhydrous p-toluenesulfonic acid in 20 g of dichloromethane, add 0.20 g of catalyst Cl - / PIM-1 (the molar ratio of covalent groups to ligands is 0.1), 4.5g 5A type molecular sieves, uniformly stirred at 20°C for 0.5h, and then added 2.2g n-butylamine. After keeping at 20°C for 6 hours, remove the molecular sieve and catalyst by filtration, and wash the filtrate once with 10 mL of 0.5 mol / L hydrochloric acid solution and 10 mL of 0.5 mol / L sodium hydroxide solution. After the organic phase was dried with anhydrous sodium sulfate, the desiccant was removed, the solvent dichloromethane was recovered by distillation, and the crude product of N-butyl-p-toluenesulfonamide was obtained. After the crude product was washed with 50% ethanol aqueous solution, 2.88 g of the product was obtained by drying. According to detection and analysis, the conversion rate of anhydrous p-toluenesulfonic acid can reach 78.52%, and the yield of N-butyl p-toluenesulfonamide can...

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 invention relates to a method of synthesis of N-alkyl p-toluene sulfonamide. In the presence of a PIMs supported solid super acid catalyst, a reaction between anhydrous p-toluene sulfonamide and a primary amine is carried out in the presence of a water absorber 5A-type molecular sieve to obtain a target product. The conversion rate of the anhydrous p-toluene sulfonamide reaches 81.90%, and the yield of the N-alkyl p-toluene sulfonamide can reach 70.53%. The method has high catalyst yield and mild reaction conditions. The catalyst is easy to recycle. The method is low in environment pollution.

Description

technical field [0001] The invention relates to a method for synthesizing N-alkyl p-toluenesulfonamide, a method for synthesizing N-alkyl p-toluenesulfonamide from p-toluenesulfonic acid and primary amine. Background technique [0002] N-Alkyl-p-toluenesulfonamides are widely used in plasticizers, polyamides, cellulose, hot-melt adhesives and plasticizing inks, and have considerable application value. At present, the main method for the synthesis of N-alkyl p-toluenesulfonamides is to react p-toluenesulfonyl chlorides with primary amines to obtain N-alkyl p-toluenesulfonamides. P-toluenesulfonyl chloride has high activity, but it is highly polluting to the environment. If N-alkyl p-toluenesulfonamide is directly prepared by anhydrous p-toluenesulfonic acid, the pollution caused by waste acid can be greatly reduced. At the same time, the activity of organic boric acid, Lewis acid catalyst and ionic liquid catalyst is not high, resulting in low conversion rate and yield, and...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/38C07C303/44C07C311/16B01J27/02B01J27/053B01J27/06B01J31/26B01J35/10B01J32/00B01J31/06
CPCC07C303/38C07C303/44B01J27/02B01J27/053B01J27/06B01J31/06B01J31/26B01J35/60C07C311/16Y02P20/584
Inventor 李翠锦
Owner 南安创友日化有限公司
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