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Method for synthesizing o-trans-(3-Cl-2-propenyl) hydroxylamine hydrochloride

A hydroxylamine hydrochloride and propylene-based technology, which is applied in the field of compound synthesis, can solve the problems of difficult industrialization and high requirements for production equipment, and achieve the effects of industrialized production, saving raw materials, and safe production process

Inactive Publication Date: 2010-02-17
NINGBO OCEAN CHEM NEW MATERIALS TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] US5585520 introduces a kind of O-(3-chloro-2-propenyl) acetone oxime ether at 40-50 ℃, 30-38mmHg with a certain reflux ratio rectification hydrolysis, distill acetone and some hydrochloric acid aqueous solution, and then The target product can be obtained by azeotropic dehydration, but this method requires high production equipment and is difficult to realize industrialization

Method used

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  • Method for synthesizing o-trans-(3-Cl-2-propenyl) hydroxylamine hydrochloride
  • Method for synthesizing o-trans-(3-Cl-2-propenyl) hydroxylamine hydrochloride

Examples

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Embodiment 1

[0039] (1) Add 174gDMSO, 26.4g (0.66mol) NaOH to a 250mL flask equipped with an electric stirrer, a thermometer, and a condenser at room temperature, stir and dissolve at room temperature, and then 43.5g (0.50mol) butanone oxime;

[0040] (2) Add 63.0g (0.55mol) trans-1,3-dichloropropene (96.0%) dropwise at 20-25°C;

[0041] (3) After the dropwise addition, react at a temperature of 20-30°C for 1 hour:

[0042](4) Then cool to room temperature, extract with cyclohexane 65g×4 (that is, the amount of each extraction is 65g, and extract 4 times in total), combine the upper layer extracts, and evaporate the cyclohexane in the extraction layer to separate O-(3 -Chloro-2-propenyl) ketone oxime ether obtains gross weight and is 338.2g;

[0043] (5) Then add 78.2g of 35% HCl (0.75mol) to the O-(3-chloro-2-propenyl)ketoxime ether obtained in step (4);

[0044] (6) Prepare a glass vacuum rectification column with an internal diameter of 20 mm and a height of 1600 mm with spring glass ...

Embodiment 2

[0046] Butanone oxime is changed into 36.5g (0.50mol) acetone oxime in step (1), other steps are with embodiment 1, the result is reclaiming O-(3-chloro-2-propenyl) acetone oxime ether 39.8g, O-reverse Formula-(3-chloro-2-propenyl)hydroxylamine hydrochloride 27.3g, yield 82.4%, product molar fraction is 99.0%.

Embodiment 3

[0048] In the step (1), the dimethyl sulfoxide consumption is changed to 220g, and other steps are with embodiment 1, the result is reclaiming O-(3-chloro-2-propenyl) butanone oxime ether 43.4g, O-trans-( 27.7 g of 3-chloro-2-propenyl) hydroxylamine hydrochloride, the yield is 83.1%, and the product molar fraction is 99.1%.

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Abstract

The invention discloses a method for synthesizing o-trans-(3-Cl-2-propenyl) hydroxylamine hydrochloride, which comprises the following steps: adding ketoxime, dimethyl sulfoxide and alkali metal hydroxide into a reaction vessel, wherein the dosage of the dimethyl sulfoxide is 3-20 times of the weight of the ketoxime, and the molar ratio of the alkali metal hydroxide and the ketoxime is 1.1-1.45:1;then dropwise adding trans-1,3-dichloropropylene; after the addition is finished, reacting at 20-50 DEG C for 1-3 hours; cooling to room temperature; adding an extracting agent to extract and separating o-(3-Cl-2-propenyl) ketoxime ether; mixing the o-(3-Cl-2-propenyl) ketoxime ether with hydrochloric acid, decompressing and rectifying to obtain the o-trans-(3-Cl-2-propenyl) hydroxylamine hydrochloride. The method for synthesizing the o-trans-(3-Cl-2-propenyl) hydroxylamine hydrochloride has low production cost, does not generate wastewater in the production process, is more safe and environmental-friendly and is easy to realize an industrialized synthesis.

Description

technical field [0001] The invention relates to the field of compound synthesis methods, in particular to a method for synthesizing O-trans-(3-chloro-2-propenyl) hydroxylamine hydrochloride. Background technique [0002] O-trans-(3-chloro-2-propenyl)hydroxylamine hydrochloride is widely used in the synthesis of cyclohexenone herbicides, such as clethodim, pyroxydone, cycloxydone, benzotrione , butazone, cyclobenzotrione, etc. These herbicides are ACCase inhibitors, a post-emergence selective herbicide, and have special effects on most annual and perennial grass weeds. The methods currently used for the synthesis of O-trans-(3-chloro-2-propenyl) hydroxylamine hydrochloride are: [0003] Wu Yingxiao etc. (pesticide, 2004, 43 (3), 113~114) introduced such a synthetic route: use ethyl acetate in the presence of sodium hydroxide, the nitrogen on the hydroxylamine is protected to generate N-acetyl hydroxylamine, and then in Under alkaline conditions, react with trans-1,3-dichlor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C239/20
CPCY02P20/582
Inventor 林勇罗署邵振平石园庆
Owner NINGBO OCEAN CHEM NEW MATERIALS TECH
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