Quinmerac and preparation method thereof

A technology of quinolinic acid and chloroquine, which is applied in the direction of organic chemistry, can solve the problems of difficult industrialization of waste acid and waste water, and achieve the effects of less side reactions, lower treatment costs of three wastes, and high purity

Active Publication Date: 2021-02-23
NUTRICHEM LAB CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a kind of method that adopts liquid phase catalytic oxidation to prepare quinclorac and the chlorine that produces a large amount of waste acid and waste water, be difficult to industrialization in the synthesis technique that existing technology exists Mequinolinic acid, through the method of the present invention, can avoid the large-scale production of waste acid and waste water, is green and environmentally friendly, and greatly reduces the cost of three wastes treatment; and, the reaction conditions are mild, the post-treatment is simple, and the product purity and yield are high, which is very suitable for Industrial production

Method used

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  • Quinmerac and preparation method thereof
  • Quinmerac and preparation method thereof
  • Quinmerac and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042]1) In a 2L four-neck glass flask, add 200 grams of 3,8-dimethyl-7-chloroquinoline, 800 grams of acetic acid, 9.26 grams of cobalt acetate (0.05 equivalents), 2.7 grams of sodium bromide (0.025 equivalents), and heat up To 100°C, wait until all the solids are dissolved, then feed the mixed gas of ozone and air at 0.4L / min, and detect the reaction in the liquid phase. After reacting for 12 hours, the temperature was lowered to 25° C., the solid was precipitated, filtered, rinsed with 30 g of acetic acid, the solid was dried, and the filtrate was used for the next batch of reactions. 214.7 g of quinclorac solid was obtained (NMR data as follows), with a purity of 98.9% by weight and a yield of 91.8%. After filtering the mother liquor, the corresponding 3,8-dimethyl-7-chloroquinoline was added, and the reaction was continued.

[0043] 1 H-NMR (500MHz, d6-DMSO) δ: 8.819(s, 1H), 8.128(s, 1H), 7.761-7.743(d, 1H, J=9Hz), 7.581-7.563(d, 1H, J=9Hz ), 2.763(s,3H), 2.497(s,3H). ...

Embodiment 2

[0049] 1) In a 2L four-necked glass flask, add 200 grams of 3,8-dimethyl-7-chloroquinoline, 1000 grams of acetic acid, 14 grams of manganese acetate (0.05 equivalents), 2.7 grams of sodium bromide (0.025 equivalents), and heat up To 100°C, wait until all the solids are dissolved, then feed the mixed gas of ozone and air at 0.4L / min, and detect the reaction in the liquid phase. After reacting for 12 hours, the temperature was lowered to 25° C., the solid was precipitated, filtered, rinsed with 50 g of acetic acid, the solid was dried, and the filtrate was used for the next batch of reactions. 215.8 grams of quinclorac solid were obtained, with a purity of 98.9% by weight and a yield of 92.2%. After filtering the mother liquor, the corresponding 3,8-dimethyl-7-chloroquinoline was added, and the reaction was continued.

[0050] The first application: In a 2L four-neck glass flask, add 200 grams of 3,8-dimethyl-7-chloroquinoline, 1010.4 grams of filtrate, heat up to 100 ° C, wait...

Embodiment 3

[0056] 1) In a 2L four-neck glass flask, add 200 grams of 3,8-dimethyl-7-chloroquinoline, 1000 grams of acetic acid, 9.3 grams of vanadium pentoxide (0.05 equivalents), and 2.7 grams of sodium bromide (0.025 equivalents) , the temperature was raised to 80°C, and when all the solids were dissolved, a mixed gas of ozone and air was introduced at 0.6 L / min, and the reaction was detected in the liquid phase. After reacting for 12 hours, the temperature was lowered to 25° C., the solid was precipitated, filtered, rinsed with 50 g of acetic acid, the solid was dried, and the filtrate was used for the next batch of reactions. 214 grams of quinclorac solid were obtained, with a purity of 98.7% by weight and a yield of 91.3%. After filtering the mother liquor, the corresponding 3,8-dimethyl-7-chloroquinoline was added, and the reaction was continued.

[0057] The first application: In a 2L four-neck glass flask, add 200 grams of 3,8-dimethyl-7-chloroquinoline, 1008.8 grams of filtrate...

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Abstract

The invention relates to the field of herbicide synthesis, particularly to quinmerac and a preparation method thereof. The method includes the steps: in the presence of a catalyst, carrying out an oxidation reaction on 3,8-dimethyl-7-chloroquine as a raw material, carboxylic acid as a solvent and oxygen-containing gas as an oxidizing agent, wherein the catalyst is one or more of a cobalt metal compound, a manganese metal compound and a vanadium metal compound. According to the method, a large amount of waste acid and waste water can be prevented from being generated, environmental protection is achieved, and the three-waste treatment cost is greatly reduced; and the method has the advantages of mild reaction conditions, simple post-treatment and high product purity and yield, and is very suitable for industrial production.

Description

technical field [0001] The invention relates to the field of herbicide synthesis, in particular to a kind of quinclorac and a preparation method thereof. Background technique [0002] Quinoracic acid is a quinoline carboxylic acid hormone-type selective herbicide, which is used in cereal crops, rapeseed and sugar beet fields to prevent and control swine worms, mother-in-law and other weeds. Also very sensitive. Its structural formula is as follows: [0003] [0004] Oxidation of methyl group to carboxylic acid is a key step in the synthesis of quinclorac. Patent US5006659 discloses the preparation of quinclorac by using 3,8-dimethyl-7-chloroquinoline as a raw material and oxidizing it with dilute nitric acid in sulfuric acid. However, this method produces a large amount of waste acid and waste water, the intermediates need to be extracted and distilled, the operation steps are many, and the yield is medium, so it is not suitable for industrial production. [0005] Pat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/48
CPCC07D215/48
Inventor 霍世勇路风奇涂俊清付裕张艳芳王晓刚
Owner NUTRICHEM LAB CO LTD
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