Preparation method of prohexadione calcium

A technology of prohexadione and dioxocyclohexanecarboxylate, which is applied in the field of preparation of prohexadione calcium

Inactive Publication Date: 2015-04-01
JIANGXI AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The object of the present invention is to provide a kind of preparation method of prohexadione calcium with low preparation cost, suitable for industrialized production, the method solves the preparation cost in the prior art High and difficult for industrial production

Method used

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  • Preparation method of prohexadione calcium
  • Preparation method of prohexadione calcium
  • Preparation method of prohexadione calcium

Examples

Experimental program
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Effect test

Embodiment 1

[0039] Place dioctyl maleate (680.00 g, 2.00 mol), acetone (84.00 g, 4.00 mol) and diethylamine (14.60 g, 0.20 mol) in an autoclave and react at 150 ℃ for 24 h. The solvent was spin-dried under reduced pressure to obtain product 1: Diisooctyl acetonyl succinate. Transfer diisooctyl acetonyl succinate to a three-necked round bottom flask, add dropwise the ethanol solution of sodium ethoxide (1 mol / L, 2.00 mol) with mechanical stirring and control the reaction temperature below 5 ℃. After the dripping is completed, continue to stir at 5 ℃ for 2 h, then rise to room temperature and stir for 12 h; after the solution is cooled below 5 ℃, add a quantitative amount of glacial acetic acid to neutralize the reaction solution, and recover ethanol under reduced pressure to obtain the product 2:3 , 5-Dioxocyclohexanecarboxylic acid isooctyl ester. Add 1,2-dichloroethane (2.7 L) into the reaction vessel containing isooctyl 3,5-dioxocyclohexane carboxylate, and add propionyl chloride (202...

Embodiment 2

[0041] Place dioctyl maleate (680.00 g, 2.00 mol), acetone (84.00 g, 4.00 mol) and diethylamine (14.60 g, 0.20 mol) in an autoclave and react at 150 ℃ for 24 h. The solvent was spin-dried under reduced pressure to obtain product 1: Diisooctyl acetonyl succinate. Transfer diisooctyl acetonyl succinate to a three-necked round bottom flask, add dropwise the ethanol solution of sodium ethoxide (1 mol / L, 2.00 mol) with mechanical stirring and control the reaction temperature below 5 ℃. After the addition is complete, continue to stir at 5 ℃ for 2 h, then warm to room temperature and stir for 12 h; after the solution is cooled below 5 ℃, add a quantitative amount of methanesulfonic acid to neutralize the reaction solution, and recover ethanol under reduced pressure to obtain product 2 :3,5-Dioxocyclohexanecarboxylic acid isooctyl ester. Add 1,2-dichloroethane (2.7 L) into the reaction vessel containing isooctyl 3,5-dioxocyclohexane carboxylate, and add propionyl chloride (202.40 g...

Embodiment 3

[0043] Place dioctyl maleate (680.00 g, 2.00 mol), acetone (84.00 g, 4.00 mol) and diethylamine (14.60 g, 0.20 mol) in an autoclave and react at 150 ℃ for 24 h. The solvent was spin-dried under reduced pressure to obtain product 1: Diisooctyl acetonyl succinate. Transfer diisooctyl acetonyl succinate to a three-necked round bottom flask, add dropwise the ethanol solution of sodium ethoxide (1 mol / L, 2.00 mol) with mechanical stirring and control the reaction temperature below 5 ℃. After the dripping is completed, continue to stir at 5 ℃ for 2 h, then warm to room temperature and stir for 12 h; after the solution is cooled below 5 ℃, add a quantitative amount of phosphoric acid to neutralize the reaction solution, and recover ethanol under reduced pressure to obtain the product 2:3, Isooctyl 5-dioxocyclohexane carboxylate. Add 1,2-dichloroethane (2.7 L) into the reaction vessel containing isooctyl 3,5-dioxocyclohexane carboxylate, and add propionyl chloride (202.40 g, 2.20 mo...

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Abstract

The invention discloses a preparation method of prohexadione calcium. Dialkyl maleate which is higher alkyl maleate having higher lipid solubility than dimethyl maleate and diethyl maleate is taken as the raw material,subjected to Michael addition under catalysis of diethylamine, then subjected to Claisencondensation under the action of organic base, and is acidized by anhydrous organic acid, anhydrous mineral acid, anhydrous phenols or inorganic diluted acid to obtain 3,5-dioxocyclohexanecarboxylate ester; then acylation under the action of an acid-binding agent, rearrangement, hydrolysis and a salt-forming reaction are performed to obtain the target productprohexadione calcium. The preparation method of prohexadione calcium has the advantages of simple operation, no need of column chromatographic separation, low preparation cost, environmental protection and suitability to industrialproduction.

Description

technical field [0001] The invention relates to the field of organic pesticide chemistry, in particular to a preparation method of prohexadione calcium. Background technique [0002] Prohexadione (calcium) [chemical name: 3,5-dioxo-4-propionylcyclohexanecarboxylic acid (calcium)], is a plant growth regulator. Its structural formula is as follows The formula shows: [0003] [0004] At present, among the synthesis routes of prohexadione calcium reported in the literature, the route described in EP123001 has the prospect of industrialization. This document uses diethyl maleate as the starting material to prepare prohexadione calcium through six steps of Michale addition, Claisen condensation, acylation reaction, rearrangement, hydrolysis, and salt formation. The synthetic route is as follows The formula shows: [0005] [0006] However, in the route reported in this document, column chromatography is used to purify the products in each step of the reaction, which is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C62/38C07C51/41
CPCC07C51/09C07C67/313C07C67/333C07C67/343C07C2601/14C07C2601/16
Inventor 黄建平
Owner JIANGXI AGRICULTURAL UNIVERSITY
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