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Preparation method of high-purity prohexadione calcium

A high-purity technology of prohexadione calcium, which is applied in the field of preparation of high-purity prohexadione calcium, can solve problems such as difficulty in improving product purity, and achieve good industrialization prospects, low equipment requirements, and simple operation steps

Pending Publication Date: 2020-05-01
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This document uses diethyl maleate as the starting material to prepare prohexadione calcium through six steps including Michale addition, Claisen condensation, acylation reaction, rearrangement, hydrolysis, and salt formation. At present, this route is relatively mature. However, it is difficult to improve the purity of products produced by domestic enterprises through this route

Method used

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  • Preparation method of high-purity prohexadione calcium
  • Preparation method of high-purity prohexadione calcium
  • Preparation method of high-purity prohexadione calcium

Examples

Experimental program
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Effect test

Embodiment 1

[0029] According to the route provided in Example 1 of Chinese Patent CN 104140368 A, using maleic acid diester as the starting material, the rearrangement product 3,5-dioxo-4-propionylcyclohexanecarboxylic acid ethyl Crude product of the ester, labeled crude rearrangement product.

[0030] The crude product of the above-mentioned rearrangement product is used as the initial raw material to prepare high-purity prohexadione calcium, and the steps are as follows:

[0031] 1) Sodium hydride was dissolved in methanol to prepare a liquid B with a concentration of 2.53% sodium hydride by mass, and the liquid B was transferred to the dropping funnel;

[0032] 2) Weigh 20 g of the rearrangement product crude product, add it to 400 ml of methanol, stir and dissolve for 1 hour, let it settle for 2 hours, filter to remove insoluble impurities, and obtain a clear methanol solution of the rearrangement product, which is marked as liquid C;

[0033] 3) At room temperature, slowly add liqui...

Embodiment 2

[0036] According to the route provided in Example 1 of Chinese Patent CN 104140368 A, using maleic acid diester as the starting material, the rearrangement product 3,5-dioxo-4-propionylcyclohexanecarboxylic acid ethyl Crude product of the ester, labeled crude rearrangement product.

[0037] The crude product of the above-mentioned rearrangement product is used as the initial raw material to prepare high-purity prohexadione calcium, and the steps are as follows:

[0038] 1) Sodium hydride is dissolved in acetone to prepare a liquid B with a concentration of 2.53% by mass of sodium hydride, and transfer the liquid B to a dropping funnel;

[0039] 2) Weigh 20 g of the rearrangement product crude product, add it to 400 ml of acetone, stir and dissolve for 1 hour, let it settle for 2.3 hours, filter to remove insoluble impurities, and obtain a clear acetone solution of the rearrangement product, which is marked as liquid C;

[0040] 3) At room temperature, slowly add liquid B (rea...

Embodiment 3

[0043] According to the route provided in Example 1 of Chinese Patent CN 104140368 A, using maleic acid diester as the starting material, the rearrangement product 3,5-dioxo-4-propionylcyclohexanecarboxylic acid ethyl Crude product of the ester, labeled crude rearrangement product.

[0044] The crude product of the above-mentioned rearrangement product is used as the initial raw material to prepare high-purity prohexadione calcium, and the steps are as follows:

[0045]1) Sodium hydride was dissolved in methanol to prepare a liquid B with a concentration of 2.53% sodium hydride by mass, and the liquid B was transferred to the dropping funnel;

[0046] 2) Weigh 20 g of the crude product of the rearrangement product, add it to 200 ml of methanol, stir and dissolve it for 1 hour, let it settle for 2 hours, filter to remove insoluble impurities, and obtain a clear methanol solution of the rearrangement product, which is marked as liquid C;

[0047] 3) At room temperature, slowly ...

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Abstract

The invention discloses a preparation method of high-purity prohexadione calcium. The preparation method comprises the following steps: dissolving sodium hydride in an organic solvent A to prepare a liquid B; adding a rearranged product, i.e., a crude product of 3,5-dioxo-4-propionylcyclohexanecarboxylic acid ethyl ester into an organic solvent A, carrying out stirring and dissolving for 0.5 to 2hours, conducting standing for precipitation, performing filtering to remove insoluble impurities, dropwise and slowly adding the prepared liquid B into the formed solution for a reaction, and performing suction filtration after dropwise adding is finished so as to obtain a solid, namely a purified rearrangement product sodium salt; hydrolyzing the obtained rearrangement product sodium salt underan alkaline condition, and carrying out acidifying to obtain prohexadione; and finally reacting prohexadione with a calcium salt to prepare the target product, i.e., prohexadione calcium. The method is simple in reaction condition, convenient to operate, free of column chromatography separation, stable in yield, low in equipment requirement and friendly to environment, and has good industrial prospects.

Description

technical field [0001] The invention relates to the technical field of organic pesticide synthesis, in particular to a preparation method of high-purity prohexadione calcium. Background technique [0002] Plant growth regulators are a class of pesticides used to regulate plant growth and development, including synthetic compounds with similar effects to natural plant hormones and natural plant hormones extracted from organisms. Calcium prohexadione is a new type of cyclohexenone plant growth regulator first developed by Japan Combination Chemical Industry Company in 1983. It belongs to 2-acyl-1,3-cyclohexanedione compounds, and its chemical name is 3, Calcium 5-dioxo-4-propionylcyclohexanecarboxylate, the English name is Calcium 3,5-dioxo-4-propionylcyclohexanecarboxylic acid, its structural formula is shown in Formula 1: [0003] [0004] Calcium prohexadione is mainly used to control the growth of cereal crops. It can shorten the length of crop stems and enhance the pl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/41C07C62/38
CPCC07C51/412C07C51/09C07C67/30C07C2601/16
Inventor 谭成侠陶敏邹文倩马天扬胡剑锋沈学峰
Owner ZHEJIANG UNIV OF TECH