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Aminobenzotrifluoride solvent-free hydrogenation reduction process

The technology of m-aminotrifluorotoluene and aminotrifluorotoluene is applied in the field of solvent-free hydrogenation reduction process of m-aminotrifluorotoluene, which can solve the problems of affecting product purity, high energy consumption, environmental hazards, etc. The effect of safety and reliability of personnel, reduction of organic emissions, and improvement of product purity

Inactive Publication Date: 2018-09-07
JIANGSU DAHUA CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The substitute object of precious metal catalyst is in order to reduce production cost, bibliographical report lacquer former nickel is made catalyst, and dehydrated alcohol is solvent, and under 45 ℃ of normal pressures, m-nitrobenzotrifluorotoluene is hydrogenated and reduced to m-trifluoromethylaniline (Luo Xinxiang, Wen Ruiming. Synthesis of m-trifluoromethylaniline. Synthetic Chemistry. 2005, 13(5), 510-512) This method can realize atmospheric pressure hydrogenation, and the yield is high; but the preparation of the catalyst is inconvenient, and zinc powder, Nickel chloride hexahydrate reacts, the reaction is violently exothermic and hydrogen gas is released at the same time, there are safety problems, and the post-treatment requires a large amount of glacial acetic acid activation and a large amount of distilled water for washing
[0009] But above-mentioned catalytic hydrogenation reduction has following one or more shortcoming: 1, all need to use organic solvent methanol, ethanol as reaction medium, not only cause harm to a certain degree to surrounding environment, personnel; 2, solvents such as methanol and The reduced amino group reacts to generate amine toluene by-products, which affects the purity of the product; 3. The reaction needs to be carried out at 105-120°C, with high temperature and high energy consumption

Method used

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  • Aminobenzotrifluoride solvent-free hydrogenation reduction process
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Examples

Experimental program
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Effect test

Embodiment 1

[0024] First, continuously purge the 5000L reduction reactor with nitrogen (<1MPa) for 3 times, and discharge the purge gas through the vent pipe. Under solvent-free conditions, add 2000kg of m-nitrobenzotrifluoride into the reaction kettle, add 2kg of Raney nickel catalyst, heat up to 80°C with steam, feed in hydrogen, and keep the temperature and pressure (80~90°C, 2.5~4.0 Under MPa) condition, carry out hydrogenation reduction reaction 6 hours. After the reaction, use nitrogen (<1MPa) to continuously purse 3 times, 65°C, normal pressure filtration to recover the catalyst, and the filtrate is rectified by negative pressure (0.09MPa, 115~125°C) for 120 hours to obtain m-trifluoroform Aniline (120±2°C) 1600kg, o-trifluoromethylaniline (118±2°C) 20kg, p-trifluoromethylaniline (123±2°C) 60kg, and the distillation residue is handled by a qualified unit.

Embodiment 2

[0026] First, continuously purge the 5000L reduction reactor with nitrogen (<1MPa) for 3 times, and discharge the purge gas through the vent pipe. Under the condition of no solvent, add 2001kg of m-nitrobenzotrifluoride into the reaction kettle, add 4kg of Raney nickel catalyst, use steam to raise the temperature to 80°C, feed hydrogen, and keep the temperature and pressure (80~90°C, 2.5~4.0 Under MPa) condition, carry out hydrogenation reduction reaction 6 hours. After the reaction, purging with nitrogen (<1MPa) continuously for 3 times, at 65°C, the catalyst was recovered by normal pressure filtration, and the filtrate was rectified by negative pressure (0.09MPa, 120-125°C) for 120 hours to obtain m-trifluoroform Aniline (120±2°C) 1610kg, o-trifluoromethylaniline (118±2°C) 20kg, p-trifluoromethylaniline (123±2°C) 50kg, and the distillation residue is handled by a qualified unit.

Embodiment 3

[0028] First, continuously purge the 5000L reduction reactor with nitrogen (<1MPa) for 3 times, and discharge the purge gas through the vent pipe. Put 2002kg of m-nitrobenzotrifluoride into the reaction kettle, add 2.5kg of Raney nickel catalyst, use steam to raise the temperature to 80°C, feed hydrogen, and carry out under the conditions of heat preservation and pressure (80~90°C, 2.5~4.0MPa) The hydrogenation reduction reaction was carried out for 6 hours. After the reaction, use nitrogen (<1MPa) to continuously purse 3 times, 65°C, normal pressure filtration to recover the catalyst, and the filtrate is rectified by negative pressure (0.09MPa, 115~125°C) for 120 hours to obtain m-trifluoroform Aniline (120±2°C) 1620kg, o-trifluoromethylaniline (118±2°C) 20kg, p-trifluoromethylaniline (123±2°C) 40kg, and the distillation residue is handled by a qualified unit.

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Abstract

The invention relates to an aminobenzotrifluoride solvent-free hydrogenation reduction process and belongs to the field of pesticide chemical product preparation methods. The process mainly comprisesthe following steps: putting a raw material, namely nitryl benzotrifluoride, into a reaction kettle, performing a hydrogenation reduction reaction under conditions that no solvent is used and raney nickel is adopted as a catalyst, after the reaction is completed, cooling, filtering at normal pressure, recycling the catalyst, and performing negative pressure distillation on filtrate, thereby obtaining aminobenzotrifluoride. The whole process is carried out under a solvent-free process condition, so that emission of organic matters in the conventional production process is reduced; the consequence that a carbaryl byproduct is generated from reactions of solvents such as methanol with reduced amino is avoided, so that the product purity can be improved; compared with a conventional solvent method, the process is relatively low in temperature, relatively low in energy consumption, low in production cost and beneficial to energy conservation and emission reduction.

Description

technical field [0001] The invention belongs to the field of preparation methods of pesticide chemical products, in particular to a solvent-free hydrogenation reduction process of m-aminotrifluorotoluene. Background technique [0002] m-Aminotrifluorotoluene is an important fluorine-containing pharmaceutical intermediate widely used in recent years, and is widely used in pharmaceutical, pesticide and dye industries. It can synthesize dozens of new fluorine-containing drugs including anti-inflammatory drugs, tranquilizers, psychotropic drugs, diuretics, antineoplastic drugs, etc. It has the advantages of fast action, high curative effect, long drug effect, wide application range and small toxic and side effects; It can be used in the production of herbicides fluuron and fluroxydone. The synthetic method of existing m-aminobenzotrifluoride mainly contains several classes such as ammonification, dehalogenation reduction, nitro reduction: [0003] (1) Ammonia method. m-Chloro...

Claims

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Application Information

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IPC IPC(8): C07C209/36C07C211/52
CPCC07C209/36C07C211/52Y02P20/584
Inventor 郑龙洲张亮方东李付香
Owner JIANGSU DAHUA CHEM IND
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