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

Preparation method of 2-chlorine-4,6-diphenyl-1,3,5-triazine

A technology of diphenyl and phenylboronic acid, applied in the direction of organic chemistry, can solve the problems of lack of economic attractiveness, corrosion equipment, long synthesis route, etc., and achieve the effects of avoiding the pressure of three wastes treatment, mild reaction conditions, and overcoming poor selectivity

Inactive Publication Date: 2019-06-07
DALIAN RES & DESIGN INST OF CHEM IND
View PDF6 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method is two-step synthesis, the process is cumbersome, and a large amount of hydrogen chloride gas will still be produced during the chlorination process using thionyl chloride, which seriously corrodes the equipment
In the post-treatment process, the reaction solvent dimethyl sulfoxide is difficult to recycle after mixing with water, and the product yield is low, which is not suitable for industrial production
There is also the condensation synthesis ring method adopted by the patent US5705643, the raw materials used are highly toxic, the synthetic route is long, it is not suitable for industrial scale production, and it lacks economic attractiveness

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
  • Preparation method of 2-chlorine-4,6-diphenyl-1,3,5-triazine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Add 18.5g (0.1mol) 1,3,5-triazine, 24.4g (0.2mol) phenylboronic acid, 21.2g (0.2mol) sodium carbonate, 1.2g catalyst Ni(dppf)Cl into a 500ml reaction flask 2 , 50g of toluene, stirring to heat up to 80°C, heat preservation reaction for 8h, cooling to room temperature, adding 100ml of water dropwise to quench the reaction, then heating up and distilling to recover the solvent toluene, cooling and filtering after no toluene fractionation, washing the filter cake with water until neutral, to obtain 2-Chloro-4,6-diphenyl-1,3,5-triazine 24.4g, yield 91.3%, purity 98.5%, of which the monosubstitution content is 0.48%, and the trisubstitution content is 0.37%.

Embodiment 2

[0023] Add 18.5g (0.1mol) 1,3,5-triazine, 26.8g (0.22mol) phenylboronic acid, 34.5g (0.25mol) potassium carbonate, 1g catalyst Ni(pcy 3 ) 2 Cl 2 , 100g tetrahydrofuran, stir and heat up to 70°C, heat-retain for 12 hours, cool to room temperature, add 100ml of water dropwise to quench the reaction, then heat up and distill to recover solvent tetrahydrofuran, cool down and filter after no tetrahydrofuran is fractionated, wash the filter cake with water until neutral, and obtain 25.2 g of 2-chloro-4,6-diphenyl-1,3,5-triazine, the yield is 94.1%, the purity is 98.9%, the content of mono-substitution is 0.28%, and the content of tri-substitution is 0.56%.

Embodiment 3

[0025] Add 18.5g (0.1mol) 1,3,5-triazine, 23.2g (0.19mol) phenylboronic acid, 31.8g (0.3mol) sodium carbonate, 2g catalyst Ni (pph 3 ) 2 Cl 2 , 100g of toluene, stirring to heat up to 110°C, heat preservation reaction for 4h, cooling to room temperature, adding 100ml of water dropwise to quench the reaction, then heating up and distilling to recover the solvent toluene, cooling and filtering after no toluene fractionation, washing the filter cake with water until neutral, to obtain 24.8g of 2-chloro-4,6-diphenyl-1,3,5-triazine, the yield is 92.6%, the purity is 98.3%, the content of mono-substitution is 0.68%, and the content of tri-substitution is 0.14%.

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 preparation method of 2-chlorine-4,6-diphenyl-1,3,5-triazine. 1,3,5-triazine and phenylboronic acid are used as start materials, nickel-phosphine complex is used as the catalyst, and the 2-chlorine-4,6-diphenyl-1,3,5-triazine is generated by one-step reaction. The method has the advantages of simple process, convenient operation, mild reaction conditions and good selectivity, and can quantitatively generate disubstituents, thus overcoming the disadvantages of Friedel-Crafts alkylation method such as poor selectivity, avoiding the pressure of anhydrous aluminum trichloride catalyst on the treatment of three wastes and meeting the requirements of environmental protection.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and in particular relates to a preparation method of 2-chloro-4,6-diphenyl-1,3,5-triazine. Background technique [0002] Triazine UV absorber is a kind of UV absorber with high absorption performance, broad spectrum, strong heat resistance and good dispersibility. It is widely used in polymer materials such as plastics, polyurethanes, and coatings. It can effectively prevent products from being damaged by ultraviolet rays. The aging caused by it enhances the color stability of the product and prolongs the service life of the material. 2-Chloro-4,6-diphenyl-1,3,5-triazine ( ) is an important intermediate for the preparation of triazine UV absorbers UV-1577 and UV-1579. [0003] [0004] There are three main methods for preparing 2-chloro-4,6-diphenyl-1,3,5-triazine. Song Guangwei et al. used 1,3,5-triazine, bromobenzene, and magnesium as raw materials in "Synthesis and Characterization of ...

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): C07D251/22
Inventor 孟纪文刘威韩建国
Owner DALIAN RES & DESIGN INST OF CHEM IND
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