Method for catalytic synthesis of triazine herbicide

A herbicide and catalyst technology, which is applied in the synthesis field of triazine herbicides, can solve the problems of low raw material conversion rate, difficult wastewater treatment, and many side reactions, and achieve simple process flow, good economic and environmental benefits, and improved conversion rate effect

Active Publication Date: 2009-08-12
SHANDONG WEIFANG RAINBOW CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these processes have problems such as many side reactions, low conversion rate of raw materials, and high cost. A large number of by-products enter the wastewater in the form of hydrolyzate, which brings great difficulties and pressures to the later wastewater treatment. Therefore, the development of The new process of preparing triazine herbicides is of great significance

Method used

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  • Method for catalytic synthesis of triazine herbicide
  • Method for catalytic synthesis of triazine herbicide
  • Method for catalytic synthesis of triazine herbicide

Examples

Experimental program
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Effect test

Embodiment 1

[0046] Synthesis of 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine

[0047](1) In a 500ml four-neck flask, add 200ml of toluene, cool the temperature to -10°C with an ice-salt water bath, and quickly add 50g (0.2711mol) of cyanuric chloride to fully dissolve it; (2) at 5°C Add dropwise 60% isopropylamine solution 26.71g (containing isopropylamine 16.02g, 0.2711mol); after dropwise addition, continue to dropwise add 30% liquid caustic soda solution 37.93g (containing sodium hydroxide 11.38g, 0.2845mol); dropwise Complete, stir 20min; (3) add catalyst tetramethylammonium bromide 0.17g (content 99%, 0.0011mol) in reaction liquid, stir 10min; (4) rise reaction temperature to 25 ℃, dropwise add 70% Monoethylamine solution 17.46g (containing monoethylamine 12.22g, 0.2711mol), continue to dropwise add 30% liquid caustic soda solution 37.93g (containing sodium hydroxide 11.38g, 0.2845mol) after the dropwise addition; 30min; (5) Add 100ml of water to the reaction solution, stir...

Embodiment 2

[0049] Synthesis of 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine

[0050] (1) In a 500ml four-neck flask, add 200ml of toluene, cool the temperature to -5°C with an ice-salt water bath, quickly add 50g (0.2711mol) of cyanuric chloride, stir well, and (2) drop at 0°C Add 26.44g of 60% isopropylamine solution (containing 15.86g of isopropylamine, 0.2684mol); continue to dropwise add 36.15g of 30% liquid caustic soda solution (containing 10.84g of sodium hydroxide, 0.2711mol) after the dropwise addition; , stirred for 20min; (3) added 0.23g of tetraethylammonium bromide (content 99%, 0.0011mol) to the reaction solution, stirred for 10min; (4) raised the reaction temperature to 20°C, and added dropwise 70% of a 17.2 g of amine solution (containing 12.04 g of monoethylamine, 0.2670 mol), after the dropwise addition, 36.15 g of 30% liquid caustic solution (containing 10.84 g of sodium hydroxide, 0.2711 mol) was continued to be added dropwise. After the dropwise addition, s...

Embodiment 3

[0052] Synthesis of 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine

[0053] (1) In a 500ml four-neck flask, add 200ml of toluene, cool the temperature to -2°C with an ice-salt water bath, quickly add 50g (0.2711mol) of cyanuric chloride, and stir evenly; (2) Add dropwise at 5°C 60% isopropylamine solution 26.71g (containing isopropylamine 16.02g, 0.2711mol); after dropwise addition, continue to drip 30% liquid caustic soda solution 36.15g (containing sodium hydroxide 10.84g, 0.2711mol); dropwise, Stir for 20 min; (3) add 0.30 g of benzyltriethylammonium bromide (content 99%, 0.0011 mol) to the reaction solution, and stir for 10 min; (4) raise the reaction temperature to 35° C., and dropwise add 70% of Ethylamine solution 17.46g (containing monoethylamine 12.22g, 0.2711mol), after the dropwise addition, continue to dropwise add 30% liquid caustic soda solution 36.15g (containing sodium hydroxide 10.84g, 0.2711mol); after the dropwise addition, stir for 30min (5) Add 100...

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Abstract

The present invention relates to a method for catalytically synthesizing triazine herbicide. The cyanuric chloride and organic substituted amine are used as raw materials. The organic solvent is used as a media in the alkaline condition. The triazine herbicide is prepared through a two-step substitution. The second step of substitution reaction is executed in the condition of catalysis by catalyst. The catalyst is quaternary ammonium or phosphonium actericide phase transfer catalyst. Compared with the prior art, the method of the invention has the advantages of simple process flow, high security, effective increase of transformation efficiency of raw material, reduced generation of secondary reaction, reduced production cost, excellent economic benefit and environmental benefit, and suitability for the large-scale industrial production.

Description

technical field [0001] The present invention relates to a method for synthesizing triazine herbicides, in particular to a method for catalyzing and synthesizing triazine herbicides, including simazine, atrazine, terbuthylazine, permethazine and cyanazine, etc. A herbicide synthesized from cyanogen chloride and organic amines. technical background [0002] The triazine herbicide of the present invention mainly refers to 4,6-disubstituted amino-1,3,5-triazine derivatives, and its general formula is: [0003] [0004] (III) In the formula, R1 and R2 are alkyl groups with ≤12 carbon atoms, cycloalkyl groups with ≤8 carbon atoms or aryl groups with ≤10 carbon atoms. [0005] The method for synthesizing 4,6-disubstituted amino-1,3,5-triazine derivative herbicides is usually prepared from cyanuric chloride and amines with different substituents through multi-step substitution reactions. According to different solvents used in the reaction, it can be divided into aqueous phase ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N43/70C07D251/50A01P13/00
Inventor 杨雨建孙国庆陈琦侯永生王福雄侯殿保张剑
Owner SHANDONG WEIFANG RAINBOW CHEM
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