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Synthetic process of O-3-chloro-2-propenyl hydroxylamine

A technology of propylene hydroxylamine and synthesis process, which is applied in the preparation of organic compounds, the preparation of carboxylate, chemical instruments and methods, etc., can solve the problems of being unsuitable for industrial production, cannot be recycled and applied, and is expensive, and achieves mild reaction conditions. , the effect of simple operation and cheap raw materials

Active Publication Date: 2016-02-24
SHANDONG KAISHENG NEW MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The amount of by-products is very large, which cannot be recovered and used mechanically; and anhydrous hydrazine is a highly toxic drug, which is expensive and not suitable for industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The synthetic technique of described O-3-chloro-2-propenyl hydroxylamine comprises the steps:

[0029] (1) Synthesis of phthaloyl chloride: add 50g phthalic acid and 107.5g thionyl chloride successively in the reactor, heat up to reflux, react for 5 hours, after the reaction is completed, excess oxychloride is removed by normal pressure distillation Sulfone, 57.8g of phthaloyl chloride was obtained;

[0030] (2) Synthesis of N-hydroxyphthalimide: 19.8g of hydroxylamine hydrochloride was dissolved in 80g of methylene chloride, and at -5°C, the phthaloyl chloride prepared in step (1) was added dropwise, After the dropwise addition was completed, the stirring reaction was continued. After the reaction was completed, dichloromethane was distilled off to obtain 44.6 g of N-hydroxyphthalimide;

[0031] (3) Synthesis of 2-(3-chloroallyloxy)indene-1,3-dione: the N-hydroxyphthalimide prepared in step (2) is dissolved in 5% Add 30.0 g of trans-1,3-dichloropropene dropwise to an...

Embodiment 2

[0036] The synthetic technique of described O-3-chloro-2-propenyl hydroxylamine comprises the steps:

[0037] (1) Synthetic of phthaloyl chloride: add 80g phthalic acid and 200.6g thionyl chloride successively in reactor, be warming up to reflux, react 5.5 hours, reaction is finished, distills off excess thionyl chloride, Obtain 89.9g of phthaloyl chloride;

[0038] (2) Synthesis of N-hydroxyphthalimide: 32.3g of hydroxylamine hydrochloride was dissolved in 120g of methylene chloride, and at 0°C, the phthaloyl chloride prepared in step (1) was added dropwise. After the addition was completed, the stirring reaction was continued. After the reaction was completed, dichloromethane was distilled off to obtain 71.5 g of N-hydroxyphthalimide;

[0039] (3) Synthesis of 2-(3-chloroallyloxy)isozaindene-1,3-dione: the N-hydroxyphthalimide prepared in step (2) was dissolved in 8% In aqueous sodium hydroxide solution, add 50.5 g of trans-1,3-dichloropropene dropwise at room temperature ...

Embodiment 3

[0044] The synthetic technique of described O-3-chloro-2-propenyl hydroxylamine comprises the steps:

[0045] (1) Synthetic of phthaloyl chloride: add 100g phthalic acid and 286.5g thionyl chloride successively in reactor, be warming up to reflux, react for 6 hours, after completion of reaction, distill and remove excessive thionyl chloride, 113.6 g of phthaloyl chloride was obtained;

[0046] (2) Synthesis of N-hydroxyphthalimide: 42.8g of hydroxylamine hydrochloride was dissolved in 150g of methylene chloride, and at 5°C, the phthaloyl chloride prepared in step (1) was added dropwise. After the addition was completed, the stirring reaction was continued. After the reaction was completed, dichloromethane was distilled off to obtain 89.0 g of N-hydroxyphthalimide;

[0047] (3) Synthesis of 2-(3-chloroallyloxy)indene-1,3-dione: the N-hydroxyphthalimide prepared in step (2) is dissolved in 10% Add 65.8 g of trans-1,3-dichloropropene dropwise to the aqueous sodium hydroxide sol...

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Abstract

The invention belongs to the technical field of organic synthesis, in particular relates to a synthetic process of O-3-chloro-2-propenyl hydroxylamine. The synthetic process comprises the following steps of (1) successively adding phthalic acid and thionyl chloride into a reactor, performing a temperature rising reaction, distilling and removing excessive thionyl chloride to obtain o-phthaloyl chloride; (2) dissolving hydroxylamine hydrochloride into dichloromethane, dropwise adding the o-phthaloyl chloride, continually stirring and reacting after dropwise adding, distilling and removing the dichloromethane after reaction completion, so as to obtain N-hydroxyl phathalicimide; (3) dissolving the N-hydroxyl phathalicimide into a sodium hydroxide aqueous solution, dropwise adding trans-1,3-dichloropropene for reaction, after reaction completion, filtering to obtain 2-(3-chloroallyloxy)-isopropyl indolizine-1,3-dione; (4) adding the 2-(3-chloroallyloxy)-isopropyl indolizine-1,3-dione into a hydrochloric acid solution for hydrolysis, filtering, collecting organic phases, and the O-3-chloro-2-propenyl hydroxylamine is obtained. The synthetic process provided by the invention has the advantages that raw materials are low in price and easy to obtain, the reaction condition is mild and the yield is high.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis process of O-3-chloro-2-propenyl hydroxylamine. Background technique [0002] O-3-chloro-2-propenyl hydroxylamine is an important pesticide and pharmaceutical intermediate, widely used in the synthesis of cyclohexenone herbicides, such as clethodim (clethodim), pyroxydim (tepraloxydim), Cycloxydim, tralkoxydim, butroxydim, clefoxidim, etc., these herbicides are ACCase inhibitors and belong to post-emergent selective herbicides. Most annual and perennial grass weeds are effective. [0003] At present, the synthesis process of O-3-chloro-2-propenyl hydroxylamine reported at home and abroad mainly contains the following three kinds: [0004] The first is to feed a large amount of hydrogen chloride gas into the toluene solution of acetonitrile and absolute ethanol to form ethyl acetylhydroxamate, then in aqueous sodium hydroxide solution, use tetra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C239/20
CPCC07C51/60C07C239/20C07D209/48C07C63/22
Inventor 杨德耀张泰铭毕义霞薛居强谢圣斌宋立伟
Owner SHANDONG KAISHENG NEW MATERIALS
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