Industrialization method for synthesizing O-chloropropene hydroxylamine by virtue of one-pot method

Abstract

The invention discloses an industrialization method for synthesizing O-chloropropene hydroxylamine by virtue of a one-pot method and a catalyst utilized in the industrialization method. The industrialization method comprises the following steps: adding acetic ester, hydroxylammonium salt and a catalyst A into a reaction kettle, adding alkali metal hydroxide, and stirring to react at 0-50 DEG C for 0-10 hours so as to generate acetohydroxamic acid; continuing to add a catalyst B and dichloropropene into reaction liquid to generate etherification reaction at 20-80 DEG C for 0-20 hours, so as to obtain N-acetyl-O-chloropropene hydroxylamine; and continuing to add protonic acid to generate acidification at 20-100 DEG C for 0-10 hours, so as to prepare O-chloropropene hydroxylammonium salt, and finally carrying out neutralization, extraction and desolvation, so as to obtain dissociative O-chloropropene hydroxylamine. The product content is higher than 99%, and the total yield is over 90%. An intermediate can be utilized for preparing high-content cyclohexenone herbicides by virtue of further reaction, is applicable to large-scale industrial production, low in cost and high in product purity and yield, and the operation is easy.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to an industrial synthesis method of O-chloropropene hydroxylamine. Background technique [0002] O-Chloropropene hydroxylamine is widely used in the synthesis of cyclohexenone oxime herbicides, such as clethodim, sethoxydim, pyroxydim, cycloxydone, benzotrione, butabenzotrione, etc., such herbicides It is an ACCase inhibitor and a post-emergence selective herbicide, which has good effect on most annual and perennial grass weeds. Cyclohexenone herbicides were first discovered by Japan Soda Corporation. In 1967, the company discovered the acaricide benzate. On the basis of this structure, it introduced the pyrone structure in coumarin, and then used the pyrone compound with herbicidal activity as the precursor to carry out its research. The structure is optimized, and the oxime ether cyclohexenone herbicide with better selectivity is obtained. In 1977, the Hefenone res...

AI Technical Summary

Problems solved by technology

The addition of DMSO makes it more difficult to recover the solvent. Cyclohexane extracts and separates products, which easily leads to a decrease in solvent recovery rate and increased cost. Acidification and hydrolysis require rectification operations, which require high production equipment and are difficult to achieve industrialization.

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