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Preparation method of triclopyr butoxyethyl ester

A technology of butoxyethyl ester and butoxyethyl hydroxyacetate is applied in the field of preparation of triclopyr butoxyethyl ester, which can solve the problem of low content of final product, expensive recovery of acid binding agent and easy generation of isomers and other problems, to achieve the effect of high product yield, cheap raw materials and less side reactions

Inactive Publication Date: 2019-10-11
LIER CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Patent CN107325044A reports that sodium clopyridinate and chloroacetic acid are used as raw materials to react to produce sodium clopyroxy acetic acid, acidified to obtain clopyroxy acetic acid, and then dried with oxalyl chloride to generate clopyroxy acetyl chloride, finally in the acid-bound Reaction with ethylene glycol butyl ether under the action of an agent to obtain triclopyr butoxyethyl ester, the total yield is 85.6%, the product content is 95.2%, the product quality is on the low side, and 2mol of sodium chloride is produced simultaneously, and the acid-binding agent used is expensive And it needs to be recycled, the operation steps are lengthy, and it is not suitable for industrialization
[0006] Patent CN102295597A reports, generate chloroacetate butoxyethyl with chloroacetic acid and ethylene glycol butyl ether esterification reaction, then react with triclopyridin sodium to generate triclopyr butoxyethyl, although this method reduces alcohol Discharge of similar wastewater, but it is easy to produce isomers, the reaction yield is low, and the content of the final product is low

Method used

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  • Preparation method of triclopyr butoxyethyl ester

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preparation example Construction

[0025] The invention provides a preparation method of triclopyr butoxyethyl ester, comprising the steps of:

[0026] (a) glycolic acid and ethylene glycol monobutyl ether undergo an esterification reaction to obtain butoxyethyl glycolate;

[0027] (b) Butoxyethyl glycolate is reacted with tetrachloropyridine to obtain the target product triclopyr-butoxyethyl.

[0028] Wherein, the reaction process of step (a) is carried out in the presence of a catalyst, and the catalyst is an acidic catalyst, and the acidic catalyst can be selected from general acidic catalysts, solid acids, heteropolyacids or solid superacids, preferably sulfuric acid or p-toluenesulfonic acid.

[0029] Further, the mass ratio of catalyst to glycolic acid is 0.1%-5%:1, preferably 4%:1.

[0030] Wherein, in the present invention, the reaction temperature of step (a) is controlled at 80-110°C, the reaction temperature of step (b) is controlled at 60-110°C, preferably, the reaction temperature of step (b) is c...

Embodiment 1

[0044] Add 500g of toluene, 326.3g of ethylene glycol monobutyl ether, and 7.5g of sulfuric acid into a 2000mL reaction bottle, and add 250g of 70% glycolic acid dropwise at 80-85°C. Pour into water, wash with sodium bicarbonate until the water phase is neutral, separate phases, concentrate and recover toluene, and then distill to obtain 377.1 g (yield 93%) of butoxyethyl glycolate with a content of 96.8%;

Embodiment 2

[0046] Add 500g of cyclohexane, 326.3g of ethylene glycol monobutyl ether, and 7.5g of sulfuric acid into a 2000mL reaction flask, raise the temperature to 80°C and add 250g of 70% glycolic acid dropwise. Pour into water, wash with sodium bicarbonate until the water phase is neutral, separate phases, concentrate and recover cyclohexane, and then distill to obtain 364.9 g (yield 90%) of butoxyethyl glycolate with a content of 93%;

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Abstract

The invention relates to a preparation method of triclopyr butoxyethyl ester, and belongs to the technical field of organic synthesis. The to-be-solved technical problem is that the reaction yield oftriclopyr butoxyethyl ester prepared by taking sodium trichloro pyridinol as an intermediate is slightly low, thereby causing slightly low content of the finally product in the prior art. The invention discloses the preparation method of the triclopyr butoxyethyl ester. Firstly, ethylene glycol monobutyl ether and glycolic acid are subjected to an esterification reaction to obtain glycolic acid butoxyethyl ester, then tetrachloropyridine is added for a reaction, and the triclopyr butoxyethyl ester is obtained. The preparation method of the triclopyr butoxyethyl ester has the advantages that the purity and yield of a target product are effectively improved, the raw materials are cheap and easy to obtain, the selectivity is good, side effects are few, the product yield is high, the reactionconditions are mild and easy to control, and the process is simple in operation and easy to industrialize.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of triclopyr-butoxyethyl ester. Background technique [0002] Triclopyr butoxyethyl ester is the abbreviation of 3,5,6-trichloro-2-pyroxyacetic acid butoxyethyl ester, which is a pyridyloxycarboxylic acid herbicide. The compound can be absorbed by the leaves and roots of the plant and transferred to the plant. It can control weeds in rice fields and wheat fields, and can also be used to control cover plants in plantations and control unprofitable trees, shrubs and broad-leaved weeds in forests. [0003] In the prior art, triclopyr-butoxyethyl is usually prepared as an intermediate using clopyridinate sodium. [0004] Patent CN109180570A reports that the etherification reaction of sodium clopyridinate and ethyl chloroacetate produces ethyl clopyroxyacetate, which is transesterified with ethylene glycol monobutyl ether under acid catalysi...

Claims

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Application Information

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IPC IPC(8): C07D213/64
CPCC07D213/64
Inventor 晏三军曾柏清黄强雷建磊胡元春左翔
Owner LIER CHEM CO LTD
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