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Method for circularly producing nicosulfuron active compound by using byproduct phenol

A technology of nicosulfuron original drug and nicosulfuron, which is applied in the preparation of phosgene or haloformate, organic chemistry, etc., and can solve the problems of high toxicity, low production efficiency, and large amount of waste water.

Active Publication Date: 2021-09-14
ZIBO NAB AGROCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The current methods for treating nicosulfuron-methyl production wastewater have disadvantages such as complex production process, low production efficiency, large amount of wastewater, high production cost, and poor controllability of some processes.
Among them, the phenyl ester method has many advantages, such as mild reaction conditions, high product purity, high production efficiency, etc., but its outstanding disadvantage is that the last two steps of the reaction all produce phenol, which can pass through the respiratory tract, skin mucous membranes and digestion. Absorbed into the body, it is a highly toxic substance
Therefore, in terms of environmental protection, phenolic substances are strictly managed, and the environmental protection treatment measures are very complicated and costly.

Method used

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  • Method for circularly producing nicosulfuron active compound by using byproduct phenol
  • Method for circularly producing nicosulfuron active compound by using byproduct phenol
  • Method for circularly producing nicosulfuron active compound by using byproduct phenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Step a: Preparation of sulfonamido-phenyl formate intermediate

[0050] Add 23 grams (0.1mol) of N,N-dimethyl-2-aminosulfonyl-3-pyridinecarboxamide, then add 24 grams (0.11mol) of diphenyl carbonate and 5.6 grams (0.1mol) of potassium hydroxide, Add 150ml of acetone and 50ml of water, stir and heat to reflux for reaction, check the end point after 5 hours until the reaction is complete, distill out acetone and recover it, add 200g of tap water, control the temperature of the reaction solution at 30-35°C, add 30% hydrochloric acid dropwise Until the pH of the reaction solution reaches 1, after filtration, the mother liquor and filter cake containing by-product phenol are obtained, the filter cake is washed, and dried to a constant weight to obtain 35 grams of phenyl ester intermediate, which has a purity of 92.3% and a yield of 92.6%;

[0051] Step b: Preparation of Nicosulfuron

[0052] Take 18.9 grams (0.05mol) of the sulfonamido-phenylformate intermediate prepared in...

Embodiment 2

[0056] Step a: Preparation of sulfonamide-phenyl formate intermediate Add 23 grams (0.1mol) of N,N-dimethyl-2-aminosulfonyl-3-pyridinecarboxamide, then add 24 grams (0.11mol) of dicarbonate Phenyl ester and 5.6 gram (0.1mol) potassium hydroxide, add 150 milliliters of acetone and 50 milliliters of water, stir and heat reflux reaction, detect end point after 5 hours, until after reaction is finished, distill out acetone recovery and apply mechanically, add 200 grams of tap water, control The temperature of the reaction solution is 20-30°C, and 30% hydrochloric acid is added dropwise until the pH of the reaction solution reaches 1. After filtration, the mother liquor and filter cake containing by-product phenol are obtained. The filter cake is washed and dried to constant weight to obtain 35.2 grams of phenyl ester intermediate. Its purity is 92.5%, and its yield is 94.6%;

[0057] Step b: Preparation of Nicosulfuron

[0058] Take 18.9 grams (0.05mol) of the sulfonamido-phenylf...

Embodiment 3

[0062] Step a: Preparation of sulfonamido-phenyl formate intermediate

[0063] Add 23 grams (0.1mol) of N,N-dimethyl-2-aminosulfonyl-3-pyridinecarboxamide, then add 24 grams (0.11mol) of diphenyl carbonate and 5.6 grams (0.1mol) of potassium hydroxide, Add 150ml of acetone and 50ml of water, stir and heat to reflux reaction, check the end point after 5 hours, until the reaction is completed, distill out the acetone for recovery, add 200g of tap water, control the temperature of the reaction solution at 28-32°C, add 30% hydrochloric acid dropwise When the pH of the reaction liquid reached 1, the mother liquor and filter cake containing by-product phenol were obtained after filtration. The filter cake was washed and dried to constant weight to obtain 35.3 g of phenyl ester intermediate with a purity of 92.3% and a yield of 95.2%.

[0064] Step b: Preparation of Nicosulfuron

[0065] Take 18.9 grams (0.05mol) of the sulfonamido-phenylformate intermediate prepared in step a and a...

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Abstract

The invention relates to the technical field of production of a nicosulfuron active compound, in particular to a method for circularly producing the nicosulfuron active compound by using a byproduct phenol. The method for circularly producing the nicosulfuron active compound by using the byproduct phenol comprises the following steps: reacting diphenyl carbonate with sulfonamide to generate a phenyl ester intermediate and a byproduct phenol; reacting phenyl ester with pyrimidinamine to generate nicosulfuron and a byproduct phenol; extracting and collecting phenol as a byproduct of the reaction in the two steps, and conducting reacting with solid light to obtain diphenyl carbonate; and subjecting the diphenyl carbonate obtained by the reaction to reaction with sulfonamide, and then producing phenol as a byproduct for next cyclic utilization. According to the method for circularly producing the nicosulfuron active compound by utilizing the byproduct phenol, provided by the invention, the reaction steps are mild and controllable, the process equipment is simple, the wastewater amount is small, the production cost is low, the product quality meets the requirements of high-end customers, a wastewater device of the byproduct phenol is omitted, the energy is saved, the production environment is improved, and the comprehensive utilization rate of resources is high.

Description

technical field [0001] The invention relates to the technical field of producing nicosulfuron technical field, in particular to a method for producing nicosulfuron technical material by recycling phenol as a by-product. Background technique [0002] The trade name of Nicosulfuron is Yunongle. It is a high-efficiency selective post-emergence herbicide for corn fields. It is mainly used to control weeds in winter and spring corn fields. Its dosage is low, its effect is good, and it is safe for corn and the environment. The majority of farmers welcome that nicosulfuron is an important high-efficiency green herbicide, and its main synthesis methods are as follows: [0003] (1) Urethane method route: [0004] Using 2-chloronicotinic acid as the raw material, first react with thionyl chloride to generate 2-chloronicotinyl chloride, then react with dimethylamine to obtain the intermediate 2-chloronicotinamide; then react with sodium hydrosulfide to obtain mercapto The sulfhydryl ...

Claims

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Application Information

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IPC IPC(8): C07D401/12C07C68/02C07C69/96
CPCC07D401/12C07C68/02C07C69/96
Inventor 邵长禄崔元兴郑有奎
Owner ZIBO NAB AGROCHEM
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