Production method of 4-cyclopropyl (hydroxy) methylene -3,5-diketone ethyl cyclohexane carboxylate and recycling method thereof

A technology of ethyl cyclohexanecarboxylate and a recovery method is applied in the preparation of carboxylate, chemical instruments and methods, preparation of organic compounds, etc., and can solve the problems of reduced economic benefits, increased production costs, etc. The effect of improving economic efficiency and simple and easy recovery method

Active Publication Date: 2019-05-21
NUTRICHEM LAB CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the invention is to overcome the existing production of 4-cyclopropyl (hydroxyl) methylene-3,5-diketone cyclohexanecarboxylate in the production process of the mother liquor is treated as organic waste liquid treatment is easy to cause Due to the defects of increased production costs and reduced economic benefits, a recovery method for 4-cyclopropyl (hydroxy) methylene-3,5-diketone cyclohexanecarboxylate and 4-cyclopropyl (hydroxy) methylene The production method of ethyl methyl-3,5-diketone cyclohexanecarboxylate

Method used

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  • Production method of 4-cyclopropyl (hydroxy) methylene -3,5-diketone ethyl cyclohexane carboxylate and recycling method thereof
  • Production method of 4-cyclopropyl (hydroxy) methylene -3,5-diketone ethyl cyclohexane carboxylate and recycling method thereof
  • Production method of 4-cyclopropyl (hydroxy) methylene -3,5-diketone ethyl cyclohexane carboxylate and recycling method thereof

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Experimental program
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Effect test

Embodiment approach

[0058] According to a preferred embodiment of the present invention, the recovery method of described 4-cyclopropyl (hydroxyl) methylene-3,5-diketone cyclohexanecarboxylate ethyl ester comprises the following steps:

[0059] (1) under the condition of complexation reaction, will contain the liquid mixture of the compound shown in formula (1) and metal ion in the first organic solvent (can be a kind of in methanol, ethanol, Virahol and tert-butanol or multiple, preferably ethanol), and the contacted mixture is subjected to solid-liquid separation to obtain a solid phase and a liquid phase, and the obtained solid phase is washed and dried, wherein the metal is listed in column 9, column 1 of the periodic table of elements One or more of the metal elements in column 10, column 11, and column 12 (preferably, the metal ion is provided in the form of metal organic acid salt, and more preferably, the metal organic acid salt is copper acetate, acetic acid One or more of cobalt, nickel...

preparation example

[0139] This preparation example is used to illustrate the preparation method of the compound represented by the formula (2).

[0140] In a 3L stainless steel autoclave, 695 g (4.0 mol) of diethyl maleate (DM), 814 g (14 mol) of acetone and 73.5 g (1 mol) of diethylamine were added successively, and the nitrogen was replaced twice. The internal pressure was 0.55 MPa, and the reaction was maintained and pressured for 12 hours under this condition, and then the sample was sampled and detected by GC, and the content of DM was less than 1% by weight. Transfer the material to the distillation device, distill at atmospheric pressure, receive the distillate (acetone, diethylamine), when the kettle temperature rises to 60 ° C, change to negative pressure precipitation, the vacuum degree is -0.095MPa, collect 60 ~ 80 °C cut (transition cut). Then, high vacuum distillation was used with a vacuum degree of 6 mmHg, and 751 g of all fractions were collected, the purity of the compound (DOP...

Embodiment 1

[0143] Preparation of compound represented by formula (1):

[0144] (1) 1200g of toluene, 70g (1.5mol) of dehydrated alcohol and 225g (3.3mol) of solid sodium ethoxide were added successively in a 3L reaction flask, and the temperature was raised to 35° C. with stirring. The compound 690g (3.0mol) shown in formula (2) took 3 hours, and after the dropwise addition, the reaction was continued for 1 hour to obtain the ECOC reaction mixture;

[0145] (2) The ECOC reaction mixture obtained in step (1) was cooled to 20° C., and 76.5 g (0.75 mol) of triethylamine was added. After the triethylamine was completely dissolved, 345 g (3.3 g of cyclopropanecarbonyl chloride) was added dropwise to it. mol) was used for 2 hours, continued to react for 1 hour after the dropwise addition, then added tap water 800g, washed with water, left standstill, layered, separated the water layer, concentrated the toluene layer under negative pressure (-0.095MPa), and removed about 600g of toluene to obta...

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Abstract

The invention relates to the field of the organic synthesis, and discloses a production method of 4-cyclopropyl (hydroxy) methylene -3,5-diketone ethyl cyclohexane carboxylate and a recycling method thereof. The recycling method comprises the following steps: (1) enabling a liquid mixture containing the compound as shown in formula (1) to contact with metal ion in a first organic solvent under a complexation condition, and performing solid-liquid separation to obtain solid phase and liquid phase, wherein the metal is one or multiple metal elements in the ninth line, the tenth line, the eleventh line and the twelfth line of an element periodic table, and the pH value of the liquid mixture is greater than 6; (2) under a ligand dissociation condition, enabling the solid phase to contact withprotonic acid in the second organic solvent to obtain the organic phase and aqueous phase containing the compound as shown in formula (1), optionally separating the compound as shown in formula (1) from the organic phase. Through the method disclosed by the invention, the compound as shown in formula (1) with high purity can be recycled from the waste liquid in a comparatively high yield.

Description

technical field [0001] The present invention relates to the field of organic synthesis, in particular, to a recovery method of 4-cyclopropyl(hydroxy)methylene-3,5-dione cyclohexanecarboxylate, and 4-cyclopropyl(hydroxy)idene Production method of methyl-3,5-dionecyclohexanecarboxylate ethyl ester. Background technique [0002] 4-Cyclopropyl(hydroxy)methylene-3,5-dione cyclohexanecarboxylate The biosynthesis of hormones can control plant growth, and when it is applied to leaves, it can be transferred to growing branches and can reduce the elongation of internodes. Applied on cereal crops, sugarcane, rapeseed, castor, rice, sunflower grass, it can obviously inhibit the growth, and can prevent lodging after application. The current synthetic route is usually to use diethyl maleate as the starting material, through addition, ring closure, acylation and rearrangement to synthesize the target product, and finally crystallization and purification in an organic solvent to obtain 4-...

Claims

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Application Information

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IPC IPC(8): C07C69/757C07C67/60C07C67/58C07C67/313C07C69/716C07C67/327C07C67/31C07C67/343
Inventor 宋蕾王晓磊刘伟汪韬马浩杰
Owner NUTRICHEM LAB CO LTD
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