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Preparation method of tralkoxydim

A technology of trimethylphenone and trimethylphenyl, applied in oxime preparation, organic chemistry, etc., can solve the problems of high price of ethoxyamine hydrochloride, unfriendly environment, high production cost, etc., and achieve high reaction yield and product purity, optimized reaction conditions, and low production costs

Pending Publication Date: 2022-02-01
江苏省农用激素工程技术研究中心有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The disadvantages of this method are: (1) the price of ethoxyamine hydrochloride is relatively high, resulting in higher production costs; (2) the use of ethoxyamine hydrochloride will also generate more waste water, which is not friendly to the environment
(3) The product contains many impurities similar in physical properties to trimethylbenzone, which are difficult to purify by physical methods such as recrystallization, resulting in low purity [the literature obtained is a light yellow oil]

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0025] This example prepares 3-hydroxy-5-(2,4,6-trimethylphenyl)-2-propionyl-cyclohex-2-en-1-one [Intermediate 1] -(2,4,6-Trimethylphenyl)-2-propioxime-cyclohex-2-en-1-one [Intermediate 2], the specific method is as follows:

[0026] Add 28.6g (0.1mol) of intermediate 1, 8.34g (0.12mol) of hydroxylamine hydrochloride and 120g of isopropanol into a reaction device equipped with a thermometer, agitator, and reflux condenser, stir and dissolve, then raise the temperature to 80°C for 3 hours .

[0027] After the reaction was completed, the temperature was lowered to 0°C to precipitate a solid, and the filter cake was dried to obtain 28.4 g of intermediate 2 with a yield of 94.4% and a purity (HPLC) of 98.5%.

Embodiment 2～ Embodiment 4）

[0029] Each embodiment is basically the same as Embodiment 1, and the differences are shown in Table 1.

[0030] Table 1

[0031] Example 1 Example 2 Example 3 Example 4 Hydroxylamine hydrochloride 8.34g (0.12mol) 6.95g (0.10mol) 10.4g (0.15mol) 13.9g (0.20mol) Intermediate 2 28.4g 23.7g 28.5g 28.2g yield 94.4% 78.7% 94.7% 93.7% purity 98.5% 95.8% 98.4% 98.7%

Embodiment 5～ Embodiment 9）

[0033] Each embodiment is basically the same as Embodiment 1, and the differences are shown in Table 2.

[0034] Table 2

[0035] Example 1 Example 5 Example 6 Example 7 Example 8 Example 9 alcohol solvent Isopropanol Isopropanol Isopropanol ethanol Butanol Isoamyl alcohol temperature reflex 80℃ 65℃ 50℃ 75℃ 90℃ 90℃ Reaction time 3h 5h 7h 4h 2h 2h Intermediate 2 28.4g 26.9g 25.2g 24.8g 26.7g 25.9g yield 94.4% 89.4% 83.7% 82.4% 88.7% 86.0% purity 98.5% 97.8% 96.4% 96.0% 97.2% 96.7%

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PUM

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Abstract

The invention discloses a preparation method of tralkoxydim. The preparation method comprises the following steps: firstly, carrying out oximation reaction on 3-hydroxy-5-(2,4,6-trimethylphenyl)-2-propionyl-cyclohex-2-ene-1-one and hydroxylamine hydrochloride, so as to obtain 3-hydroxy-5-(2,4,6-trimethylphenyl)-2-propyloximido-cyclohex-2-ene-1-one; and carrying out ethylation reaction on the intermediate II and diethyl sulfate to prepare tralkoxydim. According to the method, on one hand, the use of ethoxylamine hydrochloride is avoided, so that the production cost is lower, and the method is more environment-friendly; on the other hand, reaction conditions are optimized through a large number of experiments, high reaction yield and product purity can be obtained; the method is suitable for industrial mass production.

Description

technical field [0001] The invention belongs to the technical field of preparation of herbicides, and in particular relates to a preparation method of trimethylbenzotrione. Background technique [0002] Trimethylbenzotrione, also known as saximazone, belongs to cyclohexanedione oxime ether herbicides. [0003] Trimethylbenzophenone is a post-emergence selective herbicide for cereal crops, which can be used to control gramineous weeds in wheat and barley fields, such as foxtail, chrysanthemum, windweed, wild oats and other gramineous weeds. [0004] The adsorption of benzotrione in soil was highly correlated with organic matter and corrosive matter, and had little correlation with coarse grain and other soil factors. It disappears mainly through microbial degradation in the soil, has a short residual period in the soil, and is safe for subsequent crops. [0005] The existing methods for preparing trimethylbenzalone all use 2,4,6-trimethylbenzaldehyde as the starting materia...

Claims

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Application Information

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IPC IPC(8): C07C249/12C07C251/42C07C249/08
CPCC07C249/12C07C249/08C07C2601/16C07C251/42
Inventor 高建红万里红邹佩佩刘晓佳陈新孙永辉
Owner 江苏省农用激素工程技术研究中心有限公司
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