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

Synthetic method of N-(1H,1H,2H,2H-perfluorinated octyl) acrylamide

A perfluorooctyl and acrylamide technology, which is applied in the field of preparation of fluorine-containing compounds, can solve the problems of sensitive heating conditions, explosion, and unsuitability for industrial production, and achieve the effects of easy industrialization, simple process, and avoiding the possibility of explosion

Inactive Publication Date: 2017-01-04
JUHUA GROUP TECH CENT
View PDF2 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Sodium azide or azide is usually sensitive to heating conditions and is prone to explosion, the reported method is not suitable for industrial production

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
  • Synthetic method of N-(1H,1H,2H,2H-perfluorinated octyl) acrylamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] A kind of synthetic method of N-(1H, 1H, 2H, 2H-perfluorooctyl) acrylamide comprises the following steps:

[0024] (1) Synthesis of 1H, 1H, 2H, 2H-perfluorooctyl azide

[0025] In a 20-liter reactor, add 1500 g (3.16 mol) of 1H, 1H, 2H, 2H-perfluorohexylethyl iodide, 3 L of dimethylformamide, and 230 g (3.5 mol) of sodium azide. The mixture was stirred at room temperature for 3 h, GC showed complete conversion, selectivity 99%, added 3 L of water, allowed to stand, separated layers, the aqueous layer was washed three times with methyl tert-butyl ether, and the three-time washed organic layer was washed three times with brine to obtain Crude 1H,1H,2H,2H-perfluorooctyl azide containing methyl tert-butyl ether.

[0026] (2) Synthesis of 1H, 1H, 2H, 2H-perfluorooctylamine

[0027] Take 442 grams of 1H, 1H, 2H, 2H-perfluorooctyl azide prepared by the method of step (1) and place it in an autoclave, and replace the air with hydrogen. 40 grams of Pd / C with a Pd mass percent...

Embodiment 2

[0031] (1) Synthesis of 1H, 1H, 2H, 2H-perfluorooctyl azide

[0032] In a 20-liter reactor, add 1500 g (3.16 mol) of 1H, 1H, 2H, 2H-perfluorohexylethyl iodide, 2 L of dimethyl sulfoxide, and 205.4 g (3.16 mol) of sodium azide. The mixture was stirred at room temperature for 5 h, GC showed complete conversion, selectivity 99%, added 6 L of water, allowed to stand, separated layers, the aqueous layer was washed three times with methyl tert-butyl ether, and the three-time washed organic layer was washed three times with brine to obtain Crude 1H,1H,2H,2H-perfluorooctyl azide containing methyl tert-butyl ether.

[0033] (2) Synthesis of 1H, 1H, 2H, 2H-perfluorooctylamine

[0034] Take 442 grams of 1H, 1H, 2H, 2H-perfluorooctyl azide prepared by the method of step (1) and place it in an autoclave, and replace the air with hydrogen. 40 grams of Pd / C with a Pd mass percentage of 10% was added, and hydrogen gas was introduced to carry out a hydrogenation reduction reaction at 2 MPa. ...

Embodiment 3

[0038] (1) Synthesis of 1H, 1H, 2H, 2H-perfluorooctyl azide

[0039] In a 5-liter reactor, add 375 g (0.79 mol) of 1H, 1H, 2H, 2H-perfluorohexylethyl iodide, 1 L of N-methylpyrrolidone, and 77 g (1.18 mol) of sodium azide. The mixture was stirred at room temperature for 7 h, GC showed complete conversion, selectivity 99%, added 1 L of water, allowed to stand, separated layers, the aqueous layer was washed three times with methyl tert-butyl ether, and the organic layer washed three times with brine three times to obtain Crude 1H,1H,2H,2H-perfluorooctyl azide containing methyl tert-butyl ether.

[0040] (2) Synthesis of 1H, 1H, 2H, 2H-perfluorooctylamine

[0041] Take 221 grams of 1H, 1H, 2H, 2H-perfluorooctyl azide prepared by the method of step (1) and place it in an autoclave, and replace the air with hydrogen. 40 grams of Pd / C with a Pd mass percentage of 8% was added, and hydrogen gas was introduced to carry out a hydrogenation reduction reaction at 1.5 MPa. The reaction ...

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 discloses a synthetic method of N-(1H,1H,2H,2H-perfluorinated octyl) acrylamide. The method includes the steps that 1H,1H,2H,2H-perfluorinated hexyl ethyl iodide, sodium azide and organic solvent are mixed to react, water is added after the reaction is finished, the mixture is still standing and layered, and the organic layer is washed to obtain 1H,1H,2H,2H-perfluorinated octyl azide; under the action of Pd / C catalyst, hydrogen is used for hydrogenation reduction, and 1H,1H,2H,2H-perfluorinated octylamine is obtained through filtration and concentration; 1H,1H,2H,2H-perfluorinated octylamine, triethylamine and acryloyl chloride react in solvent at room temperature, after reaction is finished, the N-(1H,1H,2H,2H-perfluorinated octyl) acrylamide product is obtained through washing, concentration and reduced pressure distillation. The possibility of explosion in the production process is avoided, and the synthetic method has the advantages of being simple in process, safe in production, high in yield and easy to industrialize.

Description

technical field [0001] The invention relates to a preparation method of fluorine-containing compounds, in particular to a synthesis method of N-(1H,1H,2H,2H-perfluorooctyl)acrylamide. Background technique [0002] As we all know, the compound containing acrylic acid structure is one of the commonly used monomers in material chemistry, and the polymers derived from it have a wide range of applications in coatings, adhesives, preservatives, building materials, etc. For example, fluorine-containing fabric finishing agents often use acrylates containing fluorocarbon chains as part of the composition, which not only has unique waterproof, oil-proof, and anti-fouling functions, but also keeps the fabric in its original style. However, acrylate compounds containing fluorocarbon chains have poor acid and alkali resistance. Through modification, the functional group of the traditional acrylic acid containing fluorine carbon chain is replaced by an amide bond. Since the amide bond is...

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): C07C231/02C07C233/13
CPCC07C231/02C07C209/42C07C247/04
Inventor 王志光姜赟
Owner JUHUA GROUP TECH CENT
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