Industrialized method for one-pot synthesis of o-chloropropene hydroxylamine

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, in particular to an industrial synthesis method of O-chloropropene hydroxylamine. Background technique [0002] O-chloropropenylhydroxylamine is widely used in the synthesis of cyclohexenone oxime herbicides, such as clethodim, clethodim, pyrazolone, cycloxydone, saflufenone, bufendidione, etc. It is an ACCase inhibitor, a post-emergence selective herbicide, and has a good effect on most annual and perennial grass weeds. Cyclohexenone herbicides were first discovered by Japan Soda Company. In 1967, the company discovered the acaricide benzite. On the basis of this structure, the pyrone structure in coumarin was introduced, and then the pyrone compound with herbicidal activity was used as the forerunner to carry out research on it. The structure was optimized, and the oxime ether cyclohexenone herbicides with better selectivity were obtained. In 1977, the cyclohexenone herbicide researched and ...

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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