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Preparation method and application of 3-methyl-3-amino-1-pentyne

A technology of methyl and pentyne, which is applied in the field of preparation of 3-methyl-3-amino-1-pentyne, can solve the problems of difficulty in layering, low yield and large amount, and achieves convenient process implementation and high yield. high rate effect

Pending Publication Date: 2022-04-01
HANGZHOU UDRAGON CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] This method improves the yield and content, but the disadvantage is that the alkyne chlorination reaction requires a large amount of saturated hydrochloric acid and hydrogen chloride gas, and it is not easy to separate after the reaction is completed. The ammoniation reaction uses concentrated alkali to easily produce hydrolysis side reactions, and the yield is low. , still need rectification purification

Method used

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  • Preparation method and application of 3-methyl-3-amino-1-pentyne
  • Preparation method and application of 3-methyl-3-amino-1-pentyne
  • Preparation method and application of 3-methyl-3-amino-1-pentyne

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1 Preparation of 3-methyl-3-chloro-1-pentyne

[0041] Put 90g of 30% industrial hydrochloric acid (0.74mol) into the reaction bottle, start stirring, cool down to -5°C in a cold bath, add 3g of catalyst cuprous chloride, control the temperature at -5°C to 5°C and add to the solution for 2 hours 60 g (0.60 mol) of 3-methyl-1-pentyn-3-ol raw material and 80 g (0.80 mol) of 98% concentrated sulfuric acid were added dropwise, and then kept at -5°C to 5°C for 2 hours.

[0042] After the reaction system was left to stand and separated, 73 g of the upper oil layer and 160 g of the lower acid layer were obtained. The oil layer was washed with 20 g of water to obtain 70 g of the product, namely 3-methyl-3-chloro-1-pentyne.

[0043] The content of the obtained product was confirmed to be 97% by GC detection (area normalization method), and the calculated yield was 95.3%.

Embodiment 2

[0044] Example 2 Preparation of 3-methyl-3-chloro-1-pentyne

[0045] Carry out identically with embodiment 1, difference is to replace cuprous sulfate with catalyst cuprous chloride, other conditions and technological operation are unchanged. As a result, 68 g of the product 3-methyl-3-chloro-1-pentyne were obtained.

[0046] GC detection confirmed that the product content was 97%, and the calculated yield was 92.6%.

Embodiment 3

[0047] Example 3 Preparation of 3-methyl-3-chloro-1-pentyne

[0048] Proceed in the same manner as in Example 1, except that the catalyst cuprous chloride is replaced by silver nitrate, and other conditions and process operations remain unchanged to obtain 67g of product 3-methyl-3-chloro-1-pentyne.

[0049] GC detection confirmed that the product content was 97%, and the calculated yield was 91.2%.

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Abstract

The invention provides a preparation method of 3-methyl-3-amino-1-pentyne, which comprises the following steps: firstly, in the presence of sulfuric acid, hydrochloric acid and a catalyst, or sulfuric acid and hydrochloric acid as well as hydrogen chloride gas and a catalyst, carrying out alkyne chlorination reaction on 3-methyl-1-pentyne-3-alcohol, and separating to obtain 3-methyl-3-chloro-1-pentyne; and then in the presence of ammonia water, introduced ammonia gas and a catalyst, carrying out ammoniation reaction on the 3-methyl-3-chloro-1-pentyne, and separating to obtain the 3-methyl-3-amino-1-pentyne. The preparation method disclosed by the invention is more convenient in process implementation and high in yield, and has an industrial application prospect. The content of the product obtained by the method is more than or equal to 95%, and the synthesis process of zoxamide can be met without purification or only by conventional reduced pressure distillation. In addition, the product is obtained through a standing separation method, an acid layer and an ammonia water layer obtained in the standing separation operation can be recycled or reused in an upstream process, and the method has environmental protection and economic significance.

Description

【Technical field】 [0001] The present invention relates to a preparation method of 3-methyl-3-amino-1-pentyne. [0002] 【technical background】 [0003] Benzamide, test code RH-7281, English common name zoxamide, is a benzamide protective fungicide developed by Rohm and Haas Company (now Dow Agricultural Sciences Company), with a novel mechanism of action. It can effectively control diseases caused by oomycete fungi on fruit trees and vegetables including grapes and potatoes, such as potato and tomato late blight, cucumber downy mildew and grape downy mildew, etc.; Special effects, the current compound patent protection has expired. [0004] U.S. Patent US005304572A discloses a synthetic process route of benzamid, wherein 3-methyl-3-amino-1-pentyne is an important key intermediate for the preparation of benzamid. Chinese invention patent CN1183074C discloses an improved method for preparing 3-methyl-3-amino-1-pentyne. The alkyne alcohol raw material is chlorinated by alkyne i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/08C07C211/23C07C17/16C07C21/22C07C233/76A01N37/20A01P1/00A01P3/00
Inventor 沈新良王海涛沈浩袁鸿威吴华龙
Owner HANGZHOU UDRAGON CHEMICAL CO LTD
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