Synthesis method of metolachlor

The technology of a kind of metolachlor and its synthesis method is applied in the field of synthesis of metolachlor, which can solve the problems of cumbersome production operation process and low product yield, and achieve the reduction of environmental pollution, high yield and purity, and easy The effect of recycling

CN105461580AActive Publication Date: 2016-04-06SHANGYU NUTRICHEM +2
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Patent Information

Authority / Receiving Office
CN · China
Current Assignee / Owner
Publication Date
2016-04-06

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Abstract

A synthesis method of metolachlor comprises the steps of: (1) hydrogenation alkylation: dissolving2-methyl-6-ethyl aniline and methoxy acetone with an organic solvent A, adding a hydrogenation catalyst, introducing hydrogen to conduct a hydrogenation alkylation reaction, and concentrating the solvent after the reaction to obtain a reaction product B, wherein the hydrogenation catalyst is a composition of palladium carbon, Raney nickel and phosphoric acid in the weight ratio of 1-2:4-10:2-5, and the temperature of the hydrogenation alkylation reaction is 30-90 DEG C; and (2) acylation: conducting an acylation reaction on the product B with chloroacetyl chloride under the catalysis of an acid-binding agent, and conducting post-treatment after the reaction to obtain refined metolachlor. The synthesis method of metolachlor provided by the present invention has the advantages of simple operation, short production cycle, small amount of organic reagent and emission, high yield and purity of the desired products, no additional solvent in the post-treatment process, reduction of "three wastes" emissions; and the production process is safe, environmentally friendly and applicable to mass industrial production.
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Description

Technical field

[0001] The invention relates to the technical field of pesticide production, in particular to a method for synthesizing metolachlor. Background technique

[0002] Metolachlor is the active ingredient of Dore. It is the most used highly selective amide herbicide in the United States and North America. Its chemical name is 2-methyl-6-ethyl-N-(1-methyl). -2-Methoxyethyl)-N-chloroacetylaniline, the structural formula is formula 1:

[0003]

[0004] Metolachlor is mainly absorbed through the base and buds of weeds, and conducts upwards. It inhibits the synthesis of germinated seed protein and inhibits the infiltration of choline to interfere with the synthesis of lecithin, thereby inhibiting the growth of sprouts and roots. The young shoots are killed to achieve the purpose of weed control. It can be applied to crop fields such as soybean, corn, cotton, and cotton. It can prevent weeds such as crabgrass, barnyardgrass, gooseweed, golden foxtail, etc. Broadleaf weeds su...

Examples

Embodiment 1

[0045] Synthesis of product B ((1-methoxypropyl-2-(2-methyl-6-ethylphenyl)amine)

[0046]

[0047] Put 100g of 2-methyl-6-ethylaniline and 98g (1.5eqv) of methoxyacetone into the autoclave, add 100mL of toluene and stir to dissolve, and then add 0.05eqv of hydrogenation catalyst to the reaction system. The weight ratio of palladium-carbon, Raney nickel, and phosphoric acid in the hydrogenation catalyst is 1:4:2. Under stirring, replace with nitrogen for three times, and then with hydrogen for three times. The reaction temperature is 60. ℃, pressure 1.5MPa, take the reaction solution every 30min for HPLC detection, control the reaction process, when the chromatographic purity of 2-methyl-6-ethylaniline is less than or equal to 0.5% (reaction end standard), cool, filter, and use the filtrate Process water is washed with water. After the water is washed, the water ring vacuum pump distills toluene under reduced pressure to obtain 144g of colorless (1-methoxypropyl-2-(2-methyl-6-ethy...

Embodiment 18

[0055] Synthesis of metolachlor (2-methyl-6-ethyl-N-(1-methyl-2-methoxyethyl)-N-chloroacetylaniline):

[0056]

[0057] Add 100g of the product B synthesized in Example 1, 28g of potassium hydroxide (1.0eqv), 100mL of toluene, stir and cool to -10°C into a 500mL three-necked flask, and start adding 37mL of chloroacetyl chloride (1.0 eqv). After the dripping is completed and the reaction is kept for 1 hour, the HPLC controls the reaction process. After the chromatographic content of product B is ≤1%, add 100mL of process water to the reaction system and stir to wash. Under water ring vacuum desolvation, 129 g of metolachlor content is 98%, and the yield is 92%.

[0058] Compared with Example 18, the acid binding agent and the feed equivalent, reaction temperature, and chloroacetyl chloride dose equivalent were screened, and the yield and chromatographic purity of metolachlor were the indicator parameters. The results are shown in Table 1:

[0059] Table 2

[0060]

[0061] It can be s...