Preparation method of m-trifluoromethylphenol

A technology of sodium trifluoromethyl phenate and trifluoromethyl chlorobenzene, which is applied in the field of m-trifluoromethyl phenol preparation, can solve the problems of large environmental pollution, high equipment requirements, and high safety risks, and achieve low environmental pollution, High product yield and good selectivity

Active Publication Date: 2018-02-13
LIAONING TIANYU CHEM +3
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0019] The technical problem to be solved by the present invention is to overcome the problems of high equipment requirements, large environmental pollution, high production cost, high safety risk, low reaction yield and poor selectivity in the existing m-trifluoromethylphenol preparation method, Thereby a kind of preparation method of m-trifluoromethylphenol different from the prior art is provided, the preparation method of the present invention reacts with the raw material that is easier to buy in industry, the technique is simple, the aftertreatment is easy, and the conditions are relatively mild, The environmental pollution is relatively small, and m-trifluoromethylphenol with high purity can be produced in a high yield, and the cost is low, and it can be industrialized at the same time

Method used

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  • Preparation method of m-trifluoromethylphenol
  • Preparation method of m-trifluoromethylphenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] 1L autoclave, add 180.5g (1.0mol) m-trifluoromethylchlorobenzene, add 361g methanol, 80g (2.0mol) sodium hydroxide solid, 7.0g (0.02mol) 8-hydroxyquinoline copper, after adding, Close the kettle and heat up to 100~105℃, keep the kettle pressure at 0.8~1.0MPa, keep the temperature of the reaction system between 100~105℃, react for 5h, observe that the kettle pressure reaches 1.5~1.7MPa, centrally control sampling, check that the raw materials have reacted , M-trifluoromethyl phenol sodium HPLC=96.7%; the temperature of the reaction kettle is lowered, the reaction liquid is transferred to the normal pressure kettle, and the temperature of the kettle is raised to 35~40℃ under the vacuum degree of -0.03MPa, and the methanol is evaporated and recycled . After the steaming is completed, add 150 g of water to the system, adjust the pH of the reaction solution to between 7 and 8 with 36% hydrochloric acid, filter, and recover the catalyst. The mother liquor was filtered with 36...

Embodiment 2

[0054] 1L autoclave, add 180.5g (1.0mol) m-trifluoromethylchlorobenzene, add 361g methanol, 112g (2.0mol) potassium hydroxide solid, 7.3g (0.02mol) 4-methyl-8-hydroxyquinoline copper After the addition is complete, close the kettle and heat up to 100~105℃, keep the kettle pressure at 0.8~1.0MPa, keep the temperature of the reaction system between 100~105℃, react for 4h, observe that the kettle pressure reaches 1.5~1.7MPa, control sampling , The detection of raw material reaction is completed, m-trifluoromethyl phenol sodium HPLC = 94.5%; the temperature of the reaction kettle is lowered, the reaction liquid is transferred to the atmospheric kettle, and the temperature of the kettle is raised to 35-40°C under a vacuum of -0.03MPa, Distilled methanol is recycled and reused. After the steaming is completed, add 150 g of water to the system, adjust the pH of the reaction solution to between 7 and 8 with 36% hydrochloric acid, filter, and recover the catalyst. The mother liquor was...

Embodiment 3

[0056] 1L autoclave, add 180.5g (1.0mol) m-trifluoromethylchlorobenzene, add 361g n-propanol, 100g (2.5mol) sodium hydroxide solid, 5.2g (0.02mol) copper acetylacetonate, after adding, close The kettle is heated to 100~110℃, keep the kettle pressure at 0.8~1.0MPa, keep the temperature of the reaction system between 100~110℃, react for 6h, observe that the kettle pressure reaches 1.5~1.7MPa, centrally control sampling, check the raw material reaction is completed, Sodium m-trifluoromethylphenol HPLC=95.9%; the temperature of the reaction kettle is lowered, the reaction liquid is transferred to the atmospheric kettle, and the temperature of the kettle is raised to 35~40℃ under the vacuum degree of -0.03MPa, and the n-propanol is evaporated and recovered Apply. After the steaming is completed, add 150 g of water to the system, adjust the pH of the reaction solution to between 7 and 8 with 36% hydrochloric acid, filter, and recover the catalyst. The mother liquor was filtered with...

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Abstract

The invention discloses a preparation method of m-trifluoromethylphenol. A preparation method of the m-trifluoromethylphenol comprises the following steps of enabling m-trifluoromethylphenol and alkali metal hydroxide and / or alkali metal alcohol to hydrolyze in an alcohol solvent under the condition of existence of a copper complex catalyst, and acidifying a reaction solution; the copper complex catalyst is selected from one or multiple of 8-copper hydroxyquinoline, 2-methyl-8-copper hydroxyquinoline, 4-methyl-8-copper hydroxyquinoline, copper acetate, and copper acetylacetonate. The preparation method has the advantages that the raw materials which can be easily purchased in industry are used for reacting, the technology is simple, the post-treatment is easy, the conditions are relativelymoderate, the pollution to environment is smaller, the m-trifluoromethylphenol with higher purity can be prepared at higher yield rate, the cost is low, and the industrialization application is realized. (The formula is shown in the description.).

Description

Technical field [0001] The invention relates to a preparation method of m-trifluoromethyl phenol. Background technique [0002] As one of the main derivatives of m-aminobenzotrifluoride, m-trifluoromethylphenol is an intermediate widely used in medicine, low-toxic pesticides and dyes. In the field of pesticides, meta-trifluoromethylphenol is a key intermediate in the synthesis of the amido pesticide herbicides "diflufenican" and "penoxsulam", and its pyrimidine acrylate can also be used as a pesticide fungicide. In the field of medicine, m-trifluoromethyl phenol is mainly used in the important intermediates of antibiotics, 3-arylmethyl cephalosporin derivatives, synthetic anti-convulsant drugs, phenylphenoxyethyl sulfamate and anti-tuberculosis drugs N, Synthesis of N-diphenylurea derivatives. [0003] The synthesis methods of meta-trifluoromethyl phenol currently reported at home and abroad mainly include diazo hydrolysis, catalytic hydrogenation, trifluoromethylation, and hydro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/64C07C39/44C07C37/055C07C39/24
CPCC07C37/055C07C37/64C07C39/44C07C39/24Y02P20/52
Inventor 郭章红江朋陈庆忠杨晓敏
Owner LIAONING TIANYU CHEM
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