Method for taking powder alkali as acid-binding agent in chloromethyl alkyl ether nitrogen-alkylation reaction

A technology of chloromethyl alkyl ether azane and powder alkali acid binding agent, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc. To solve problems such as large amount of alkali, to achieve the effect of improving equipment utilization, reducing emissions, and small material volume

Inactive Publication Date: 2012-05-09
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] There are some bibliographical reports to reduce the method of alkali consumption at present, as Zhang Fusheng etc. (Journal of Jilin Institute of Chemical Technology, 2001,18, p14-16) have improved condensation process in the production of acetochlor, be 42% sodium hydroxide with mass percent The solution replaces 47% sodium hydroxide solution and is directly used in production, which reduces the operation of preparing high-concentration alkali, but the conversion rate of synthesis is not ideal, and the effect of saving alkali is not obvious
The problem of using a large amount of alkali is one of the technological difficulties in the synthesis of acetochlor, butachlor and other bulk herbicides by the chloromethyl ether method

Method used

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  • Method for taking powder alkali as acid-binding agent in chloromethyl alkyl ether nitrogen-alkylation reaction
  • Method for taking powder alkali as acid-binding agent in chloromethyl alkyl ether nitrogen-alkylation reaction
  • Method for taking powder alkali as acid-binding agent in chloromethyl alkyl ether nitrogen-alkylation reaction

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Experimental program
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Effect test

Embodiment 1

[0024] Embodiment 1: powder alkali preparation

[0025] There are two methods for the preparation of powdered alkali, one is the ball milling method, the solid alkali is directly added to the ball mill, crushed into an appropriate particle size, sieved, and the powder alkali below 40 mesh is reserved for future use; the other is the liquid phase method, the solid alkali is added to the In solvents, such as xylene, toluene, etc., the mass ratio is solid alkali:solvent=1:10~1:1, and the high-speed emulsifier (DE-100L type) is used for shearing and pulverization, and the particle size is lower than 40 mesh and sealed for later use .

Embodiment 2

[0026] Embodiment 2: 2 times the amount of powdered alkali as an acid-binding agent to synthesize acetochlor

[0027]

[0028] Add 30ml of xylene and 3g (0.07mol, 60-100 mesh) of solid sodium hydroxide powder into a 100ml three-necked flask equipped with a thermometer, a constant pressure dropping funnel, and a mechanical stirrer, and add 8g (0.04mol) of amide under stirring. , temperature 15°C, add 4.9g (0.05mol) of chloromethyl ethyl ether dropwise under stirring, control the temperature not higher than 30°C for about 15min, continue to keep warm at 35°C for 20min, and the reaction is complete. 10 ml of water was added for washing, the liquid was separated, and the organic phase was concentrated to obtain 10.2 g (0.038 mol) of acetochlor with a purity of 96% and a yield of 96%.

Embodiment 3

[0029] Embodiment 3: 1.5 times the amount of powdered alkali as an acid-binding agent to synthesize acetochlor

[0030]

[0031] Add 30ml of xylene, 2.3g of solid sodium hydroxide powder (0.057mol, 60-100 mesh) into a 100ml three-necked flask equipped with a thermometer, a constant pressure dropping funnel, and a mechanical stirrer, and add 8g of amide (0.04mol ), the temperature is 15°C, add 4.9g (0.05mol) of chloromethyl ethyl ether dropwise under stirring, control the temperature not higher than 30°C, the time is about 15min, continue to keep warm at 35°C for 20min, and the reaction is completed. Add 10ml of water for washing, separate the liquid, and concentrate the organic phase to obtain acetochlor, with 0.8% of the amide raw material remaining, the product quality is 10g, the purity is 96%, and the yield is 95%.

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Abstract

The invention belongs to the technical field of organic synthesis and particularly relates to a method for carrying out a chloromethyl alkyl ether nitrogen-alkylation reaction by taking powder alkali with specified granularity as an acid-binding agent. Compared with a method for taking corresponding aqueous water as the acid-binding agent, the method disclosed by the invention has the characteristics of simleness, convenience and high yield. The method comprises the following steps of: dispersing acid amide and the power alkali as the acid-binding agent into a solvent, wherein in a reaction system, the concentration of the acid amide is 100-300mg / Ml and the mol ratio of the acid amide to the acid-binding agent is (1:1.5)-(1:3); controlling the temperature of the reaction system to be 10-20DEG C; dropping chloromethyl alkyl ether by stirring, wherein the mol ratio of the acid amide to the chloromethyl alkyl ether is (1:1)-(1:2); after dropping, controlling the temperature of the reaction system not to be higher than 30DEG C and reacting for 10-30 minutes; reacting at the temperature of 30-40DEG C for 15-30 minutes and finishing reaction; and adding water for washing a product to dissolve the generated salt; and after liquid separation, concentrating an organic phase to obtain alkoxy methylene-substituted acid amide.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a method for nitrogen alkylation of chloromethyl alkyl ethers using powdered alkali with a specific particle size as an acid-binding agent. Compared with the present invention, the method has the advantages of simplicity and high yield. Background technique [0002] Chloromethyl alkyl ethers are a class of very active organic synthesis reagents, such as chloromethyl methyl ether, chloromethyl ethyl ether, chloromethyl propyl ether, and chloromethyl n-butyl ether. As a protecting group or reaction reagent, it is widely used in various organic synthesis reactions. For example, as a protecting group, chloromethyl methyl ether is the most widely used hydroxyl protecting group. Generally, under alkaline conditions, chloromethyl methyl ether and hydroxyl compounds After reaction, the hydroxyl group after ether formation is protected. The removal of the protecting...

Claims

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Application Information

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Patent Type & AuthorityApplications(China)
IPC IPC(8): C07C231/12C07C233/18
Inventor张锁秦郑良玉吴坤刘庆文姜毅君田晓军王传林
OwnerJILIN UNIV