Preparation method of O-3-chloro-2-propenylhydroxylamine

A technology of chlorinated amines and hydroxylamine salts, applied in oxime preparation, organic chemistry, etc., can solve problems such as unfavorable industrial production, pollution, corrosion, etc., and achieve the effect of improving reaction rate and yield

Inactive Publication Date: 2019-03-08
江苏艾科维科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the use of a large amount of hydrogen chloride gas in the reaction process, the pollution and corrosion are relatively serious, which is not conducive to industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] The preparation method of present embodiment chlorinated amine, comprises the following steps:

[0020] Add hydroxylamine sulfate, water, and acetone into a three-necked flask, stir evenly, add sodium hydroxide solution with a mass fraction of 10%, and react at room temperature for 2 hours to obtain acetone oxime, then add 1,3-dichloropropene and phase transfer catalyst four Butyl ammonium bromide, heated in a water bath and controlled the temperature at 70°C for 8 hours, then allowed to stand to separate layers, separated and collected the oil phase, extracted the oil phase twice with ethyl acetate, dried the extract with anhydrous sodium sulfate, and then Remove the solvent under reduced pressure to obtain the product; the molar ratio of the hydroxylamine sulfate to acetone is 0.5:1; the molar ratio of the hydroxylamine sulfate to 1,3-dichloropropene is 0.5:1.

[0021] The yield of the chlorinated amines prepared in this embodiment is 90%, and the purity is 99%.

Embodiment 2

[0023] The preparation method of present embodiment chlorinated amine, comprises the following steps:

[0024] Add hydroxylamine sulfate, water, and acetone into a three-necked flask, stir evenly, add a sodium hydroxide solution with a mass fraction of 20%, and react at room temperature for 1 hour to obtain acetone oxime, and then add 1,3-dichloropropene and a phase transfer catalyst. Hexaalkyltrimethylammonium bromide, heating in a water bath and controlling the temperature at 90°C for 5 hours, then standing to separate layers, separating and collecting the oil phase, extracting the oil phase with ethyl acetate for 3 times, and using anhydrous sulfuric acid for the extract After drying with sodium, the solvent is removed under reduced pressure to obtain the product; the molar ratio of the hydroxylamine sulfate to acetone is 0.5:1.1; the molar ratio of the hydroxylamine sulfate to 1,3-dichloropropene is 0.5:1.2.

[0025] The yield of the chlorinated amines prepared in this emb...

Embodiment 3

[0027] The preparation method of present embodiment chlorinated amine, comprises the following steps:

[0028] Add hydroxylamine sulfate, water, and acetone into a three-necked flask, stir evenly, add sodium hydroxide solution with a mass fraction of 30%, and react at room temperature for 1 hour to obtain acetone oxime, then add 1,3-dichloropropene and phase transfer catalyst three Octyl ammonium chloride, heated in a water bath and controlled temperature at 80°C for 7 hours, then allowed to stand to separate layers, separated and collected the oil phase, extracted the oil phase 3 times with ethyl acetate, dried the extract with anhydrous sodium sulfate, and then Remove the solvent under reduced pressure to obtain the product; the molar ratio of the hydroxylamine sulfate to acetone is 0.5:1.1; the molar ratio of the hydroxylamine sulfate to 1,3-dichloropropene is 0.5:1.5.

[0029] The yield of the chlorinated amines prepared in this embodiment is 89%, and the purity is 99.3%. ...

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Abstract

The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of O-3-chloro-2-propenylhydroxylamine. The preparation method of the O-3-chloro-2-propenylhydroxylamine comprises the following steps: uniformly stirring hydroxylamine salt, water and acetone, adding a sodium hydroxide solution, reacting at room temperature for 1 to 2 hours, then adding 1,3-dichloropropene and a phase transfer catalyst, heating in water bath, controlling the temperature at 60 to 90 DEG C, reacting for 5 to 10 hours, standing still for stratification, separatingand collecting an oil phase, extracting the oil phase 2 to 3 times with an extractant, drying extract liquid with anhydrous sodium sulfate, and removing a solvent under reduced pressure to obtain theO-3-chloro-2-propenylhydroxylamine. According to the preparation method of the O-3-chloro-2-propenylhydroxylamine provided by the invention, acetone oxime is firstly prepared by taking the hydroxylamine salt and acetone as raw materials, and then 1,3-dichloropropene and the phase transfer catalyst are added for a reaction to prepare the O-3-chloro-2-propenylhydroxylamine; the O-3-chloro-2-propenylhydroxylamine prepared with the preparation method has the purity of 99% or more than 99% and the yield of 88% or more than 88%, and the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of chlorinated amines. Background technique [0002] Chloroamine, O-3-chloro-2-propenyl hydroxylamine, is a non-important pesticide and pharmaceutical intermediate, especially widely used in the synthesis of cyclohexenone herbicides, such as clethodim, pyroxen ketone, cycloxydone, benzotrione, butazone, cyclobenzotrione, etc. These herbicides are ACCase inhibitors and a post-emergence selective herbicide, which is effective for most annual and perennial grasses. Grass has special effects. [0003] The common method of existing synthetic chlorinated amines is to pass into a large amount of hydrogen chloride gas in the toluene solution of acetonitrile and dehydrated alcohol, form acetyl hydroxamate ethyl ester, bromide with tetrabutyl in sodium hydroxide solution again Ammonium is used as a phase transfer catalyst to produce products thr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C239/20C07C251/38C07C249/08
CPCC07C239/20C07C249/08C07C251/38
Inventor 叶茂伟刘建青汪俊杰李鲁祯
Owner 江苏艾科维科技股份有限公司
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