Method for preparing quinclorac through catalytic oxidation
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A technology of quinclorac and methylquinoline, applied in chemical instruments and methods, molecular sieve catalysts, physical/chemical process catalysts, etc., can solve the problems of severe oxidation reaction, high production cost, and high reaction temperature, and achieve a safety factor High, low cost, mild reaction conditions
Active Publication Date: 2018-04-03
NANJING UNIV OF TECH
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Problems solved by technology
[0006](1) Concentrated nitric acid is used as an oxidant, the oxidation reaction is violent, difficult to control, with many by-products, high production cost, a large amount of waste acid will be produced, and it will cause great harm to the environment
[0007](2) With concentrated sulfuric acid as the reaction medium, a large amount of waste acid will be produced during production, which will also cause equipment corrosion
[0008](3) The use of a large amount of metal salts in the reaction will produce waste liquid containing metal ions, which will cause serious environmental pollution
However, this method has disadvantages such as high reaction temperature and high pressure.
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Embodiment 1
[0019] In a 100mL three-neck round bottom flask, add 2.5g of 7-chloro-8-methylquinoline chloride, 0.024g of sodium tungstate dihydrate, 0.05g of tetrabutylammonium bromide, Add 0.1 g of molecular sieves, add 50 mL of acetonitrile, stir, add 4.1 mL of 30% hydrogen peroxide dropwise into the reaction flask, and react at 90° C. for 5 h. After the reaction was finished, the reaction solution was cooled to room temperature, and the material was discharged, and analyzed by HPLC, the yield of quinclorac was 68%.
Embodiment 2
[0021] In a 100mL three-neck round bottom flask, add 2.5g of 7-chloro-8-methylquinoline chloride, 0.024g of sodium tungstate dihydrate, 0.05g of tetrabutylammonium bromide, Add 0.1 g of molecular sieves, add 50 mL of acetonitrile, stir, add 4.1 mL of 30% hydrogen peroxide dropwise into the reaction flask, and react at 90° C. for 10 h. After the reaction was finished, the reaction solution was cooled to room temperature, and the material was discharged, and analyzed by HPLC, the yield of quinclorac was 76%.
Embodiment 3
[0023] In a 100mL three-neck round bottom flask, add 2.5g of 7-chloro-8-methylquinoline chloride, 0.024g of sodium tungstate dihydrate, 0.05g of tetrabutylammonium bromide, Add 0.1 g of molecular sieves, add 50 mL of acetonitrile, stir, add 4.1 mL of 30% hydrogen peroxide dropwise into the reaction flask, and react at 90° C. for 10 h. After the reaction was finished, the reaction solution was cooled to room temperature, and the material was discharged, and analyzed by HPLC, the yield of quinclorac was 78%.
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Abstract
The invention provides a method for preparing quinclorac through catalytic oxidation of 7-chloro-8-methylquinoline chloride. A synthetic route of the quincloac is shown in the description. The methodcomprises steps as follows: 7-chloro-8-methylquinoline chloride as a starting material, one or two of water, methanol and acetonitrile as solvents, oxygen, hydrogen peroxide or tert-butyl hydroperoxide as an oxidizing agent and transition metal salt as a catalyst form a compound catalysis system with a catalyst promoter molecular sieve in the description and quaternary ammonium salt, the compoundsynthesis system reacts at the temperature of 35-90 DEG C for 1-12 h, and quinclorac is obtained after conventional separation and has the yield range of 26%-28%. The transition metal salt is taken asthe catalyst, little transition metal salt is used, clean and cheap oxygen and hydrogen dioxide are used to replace high-cost concentrated nitric acid producing severe three wastes, environmental pollution is notably reduced, the production cost is reduced, the reaction condition is relatively mild, and the method is simple and convenient to operate, can be popularized to large-scale industrial production and has great significance in clean production.
Description
technical field [0001] The present invention relates to a method for preparing aromatic acid, in particular to a method for preparing quinclorac by catalytic oxidation of 7-chloro-8-methylquinoline chloride. Background technique [0002] Dichloroquinoline acid (Quinclorac), also known as 3,7-dichloro-8-quinoline carboxylic acid, the molecular formula is C 10 h 5 Cl 2 NO 2 , with a molecular weight of 242.1. Quinclorac is an effective selective herbicide for controlling barnyardgrass in paddy fields. It is a hormone-type quinoline carboxylic acid herbicide. The symptoms of weed poisoning are similar to those of auxins. It is mainly used to control barnyard grass and has a long application period. It is effective at the 1-7 leaf stage, and the rice has good safety. In recent years, the excellent herbicidal performance of quinclorac has been favored by the market, and the price of the original drug remains high. Therefore, it has great development value and good prospects ...
Claims
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