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Preparation method and application of 2, 6-diethyl-4-methylphenylmalonic acid diester

A technology of methyl phenyl malonate diester and methyl phenyl malononitrile, which is applied in the field of pinoxaden intermediate synthesis, can solve the problems of complex control parameters, plugged microchannel tubes, and large equipment investment, and achieves Good selectivity, good decomposition and high product yield

Pending Publication Date: 2021-08-31
LIER CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This process needs to use a microchannel reactor, and ammonium chloride salt is produced during the reaction process, which will cause the problem of blocking the microchannel tube, which requires a large investment in equipment and complicated control parameters.

Method used

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  • Preparation method and application of 2, 6-diethyl-4-methylphenylmalonic acid diester
  • Preparation method and application of 2, 6-diethyl-4-methylphenylmalonic acid diester
  • Preparation method and application of 2, 6-diethyl-4-methylphenylmalonic acid diester

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preparation example Construction

[0045] In some embodiments, the preparation method of the 2,6-diethyl-4-methylphenylmalonate diester comprises: 2,6-diethyl-4-methylphenylmalononitrile, Prepare a mixed solution with inorganic acid, water, organic solvent and alcohol, react at 70-130°C for 6h-11h, then cool, filter and concentrate to obtain the product.

[0046]In some preferred embodiments, the preparation method of the 2,6-diethyl-4 methylphenylmalonic acid diester comprises: 2,6-diethyl-4 methylphenylmalonate Nitrile, inorganic acid, water, organic solvent, alcohol to prepare a mixed solution, react at 80-110°C for 6h-11h, then cool, filter and concentrate to obtain the product.

[0047] In some more preferred embodiments, the preparation method of the 2,6-diethyl-4 methylphenylmalonate diester comprises: 2,6-diethyl-4 methylphenylpropane Dinitrile, inorganic acid, water, organic solvent, and alcohol are prepared to obtain a mixed solution, reacted at 80-95°C for 6h-8h, and then cooled, filtered and concen...

Embodiment 1

[0051] A kind of preparation method of 2,6-diethyl-4 methylphenylmalonate diester, its general reaction formula is as follows:

[0052]

[0053] In 500mL reactor, add xylene 220g, concentrated sulfuric acid (11g, 0.11mol), water (3.6g, 0.2mol), 2-(2,6-diethyl-4-methylbenzene) malononitrile (22g, 0.1mol), methanol (7.08g, 0.22mol) to start stirring, and stir until the system is clear. Turn on the heating to raise the temperature, keep the internal temperature of the reaction system at 80-95°C, and keep the reaction for 6 hours. After the reaction was completed, it was cooled to room temperature and filtered, and the filtrate was concentrated to obtain 2,6-diethyl-4-methylphenylmalonate with a weight of 26.4 g, a purity of 97.1%, and a yield of 92.1%.

[0054] The product is a white solid with a melting point of 54°C-55°C. 1 HNMR (CDCl 3 ): δ1.18(t, 6H), 2.30(s, 3H), 2.64(q, 4H), 3.73(s, 6H), 5.06(s, 1H), 6.93(s, 2H); 13 CNMR (CDCl 3 ):15.2,21.1,26.6,51.5,52.6,126.4 ,127...

Embodiment 2

[0056] A kind of preparation method of 2,6-diethyl-4 methylphenylmalonate diester, its general reaction formula is as follows:

[0057]

[0058] Add xylene 220g, water (3.6g, 0.2mol), 2-(2,6-diethyl-4-methylbenzene) malononitrile (22g, 0.1mol), ethanol (11.5 g, 0.25mol) to start stirring, stirring until the system is clear. Dry hydrogen chloride (8 g, 0.22 mol) was passed through. Turn on the heating to raise the temperature, keep the internal temperature of the reaction system at 95-110°C, keep the temperature for 8 hours, cool to room temperature after the reaction is completed, filter the filtrate, and obtain 2,6-diethyl-4-methylphenylmalonic acid di The weight of ethyl ester is 29.07g, the purity is 95.9%, and the yield is 91%.

[0059] The product is a colorless oil, 1 HNMR (CDCl 3 ): δ1.19(t, 6H), 1.27(t, 6H), 2.30(s, 3H), 2.6 5(q, 4H), 4.22(m, 4H), 5.02(s, 1H), 6.92(s , 2H).

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Abstract

The invention belongs to the technical field of pinoxaden intermediate synthesis, and particularly provides a preparation method of 2, 6-diethyl-4-methylphenylmalonic acid diester, which specifically comprises the following steps of: in the presence of an organic solvent, reacting 2, 6-diethyl-4-methylphenylmalononitrile as a raw material with inorganic acid, water and alcohol to obtain the 2, 6-diethyl-4-methylphenylmalonic acid diester. The reaction has the advantages of cheap and easily available reagent raw materials, good selectivity, few side reactions, high product yield, mild and easily controllable reaction conditions, simple process operation and easy industrialization and is a brand-new synthesis route, the generated ammonium sulfate solid can be used as a nitrogen fertilizer, and few three wastes are generated.

Description

technical field [0001] The invention belongs to the technical field of the synthesis of pinoxaden intermediates, and in particular relates to a preparation method of 2,6-diethyl-4-methylphenylmalonate diester. Background technique [0002] Pinoxaden is a new phenylpyrazoline herbicide developed by Syngenta Crop Protection Co., Ltd. in Switzerland. It is an acetyl-CoA carboxylase (ACC) inhibitor herbicide. The leaf absorbs it, and then conducts it to the meristem, causing fatty acid synthesis to be blocked, cell division to stop, cell membrane lipid-containing structure to be destroyed, and weeds to die. This variety is systemic and fast-acting. Generally, sensitive weeds stop growing within 48 hours after application, the weed leaves start to turn yellow within 1-2 weeks, and the weeds completely die within 3-4 weeks. The response speed of weed damage after pesticide application is related to climatic conditions, weed species, growth conditions and so on. The drug is highl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/22C07C69/612
CPCC07C67/22C07C69/612
Inventor 王福雄蔡佳李岳东晏三军闫潇旭程柯
Owner LIER CHEM CO LTD
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