Calixarene Phase Transfer Catalyst and Its Application in Prothioconazole Intermediate Production

A technology of phase transfer catalyst and prothioconazole, which is applied in the direction of catalytic reaction, physical/chemical process catalyst, organic compound/hydride/coordination complex catalyst, etc., which can solve the problem of unsatisfactory materials, high cost and unfavorable industrialization Application and other issues, to achieve the effect of saving equipment investment, reducing decomposition, good molecular recognition and inclusion ability

Active Publication Date: 2022-05-13
河北旭阳能源有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Obviously, these two methods have obvious effects on the heat control of the reaction, but, because the reaction process uses strong alkaline substances such as sodium hydroxide, the material of the general microreactor does not meet the requirements, causing the cost of this type of method to increase. Good for industrial application

Method used

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  • Calixarene Phase Transfer Catalyst and Its Application in Prothioconazole Intermediate Production
  • Calixarene Phase Transfer Catalyst and Its Application in Prothioconazole Intermediate Production
  • Calixarene Phase Transfer Catalyst and Its Application in Prothioconazole Intermediate Production

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Experimental program
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Effect test

Embodiment 1

[0044] The structural formula of raw material 3,5-dichloro-2-pentanone is shown in IV:

[0045]

[0046] The structural formula of 1-acetyl-1-chlorocyclopropane is shown in V:

[0047]

[0048] Set up mechanical stirring, reflux condenser and constant pressure dropping funnel above the 2L three-necked flask. At room temperature, add 500 mL of dichloromethane, 48 g (1.2 mol) of sodium hydroxide, 110 mL of water and 1.0 g of a calix[4]arene derivative phase transfer catalyst (structural formula shown in II). 155 g (1.0 mol) of 3,5-dichloro-2-pentanone was added within 45 min to the system at 40°C. Subsequently, at 40 °C. The reaction was continued for 1 hour, the system was lowered to room temperature, and the liquid was separated. After the organic phase was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the distillation was continued to obtain a light yellow oily liquid, which was the target product 1-acetyl-1-chlorocy...

Embodiment 2

[0050] Set up mechanical stirring, reflux condenser and constant pressure dropping funnel above the 2L three-necked flask. At room temperature, 500 mL of chlorobenzene, 48 g (1.2 mol) of sodium hydroxide, 110 mL of water and 1.0 g of a calix[4]arene derivative phase transfer catalyst (structural formula as shown in III) were added. 155 g (1.0 mol) of 3,5-dichloro-2-pentanone was added within 45 min to the system at 40°C. Subsequently, at 40 °C. The reaction was continued for 1 hour, the system was lowered to room temperature, and the liquid was separated. After the organic phase was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the distillation was continued to obtain a light yellow oily liquid, which was the target product 1-acetyl-1-chlorocyclopropane , yield 96%, GC content > 98%.

[0051] The aqueous phase obtained by the reaction is acidified with hydrochloric acid until the pH is about 3.0, extracted with chlorobenzen...

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Abstract

The invention discloses a calixarene phase transfer catalyst and its application in the production of prothioconazole intermediates, and relates to the technical field of phase transfer catalysts. The general structural formula of the calix[4]arene derivative phase transfer catalyst is shown in I: in the formula, R is -H or R 2 , at least one of the four R is R 2 ; 2 It is an alkyl chain of 1‑10 carbons with a hydrophilic group, or a polyoxyethylene group; R 1 is ‑H or tert-butyl. The application of the calix[4]arene derivative phase transfer catalyst is: the application in the production of prothioconazole intermediate 1-acetyl-1-chlorocyclopropane. As a phase transfer catalyst, the calix[4]arene derivative of the present invention has better molecular recognition and inclusion ability, can effectively promote the reaction, and reduce the decomposition of the product 1-acetyl-1-chlorocyclopropane in an alkaline environment , improve the product yield, the process is simple, and the efficiency of the reaction system is high.

Description

technical field [0001] The invention relates to the technical field of phase transfer catalysts, in particular to a calixarene phase transfer catalyst and its application in the production of prothioconazole intermediates. Background technique [0002] 1-Acetyl-1-chlorocyclopropane is a key intermediate for the production of the pesticide prothioconazole. In Bayer’s patent US2005022451, 3,5-dichloro-2-pentanone is reacted with about 30% and excess liquid alkali. It can be obtained through cyclization and dechlorination. [0003] There are certain problems with this reaction. At first, this reaction heat release is big, will generate a large amount of yellow-brown tar-like substances to poor temperature control; Secondly, product 1-acetyl group-1-chlorocyclopropane is unstable, and in the process of quenching reaction, excess Alkaline water will accelerate the decomposition of the product. Therefore, optimization can be considered from several aspects such as raw material ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/02B01J31/04C07C45/61C07C59/72C07C309/11C07C49/327C07C303/32C07C51/09
CPCB01J31/04B01J31/0229B01J31/0225C07C309/11C07C59/72C07C45/61B01J2231/4205C07C2603/92C07C49/327
Inventor 孟祥尹天长张捷闫英然何海娜杨克明闫晶红杨学林
Owner 河北旭阳能源有限公司
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