Method for preparing p-trifluoromethylaniline by performing high pressure ammonolysis

A technology of trifluoromethylaniline and p-chlorobenzotrifluoride, which is applied in the field of high-pressure ammonolysis to prepare p-trifluoromethylaniline, can solve the problems of high cost of trifluoromethyl reagents, low conversion rate, and difficult post-processing, etc. Achieve the effects of avoiding side reactions of hydrolysis, convenient recycling, and reducing production costs

Active Publication Date: 2013-11-27
JIANGSU FENGHUA CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The mixture of PTFMA and o-trifluoromethylaniline generated in the reaction, the conversion rate of the reaction is low, and the cost of the trifluoromethyl reagent is too high
[0009] (5) The method of chlorination, fluorine substitution, and reduction after the reaction of p

Method used

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  • Method for preparing p-trifluoromethylaniline by performing high pressure ammonolysis
  • Method for preparing p-trifluoromethylaniline by performing high pressure ammonolysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] To the 3L autoclave, add 300g p-chlorotrifluorotoluene, 25g cuprous chloride, 10g copper powder, 90g sodium carbonate, 900g polyethylene glycol 300, seal the autoclave, and after three times of nitrogen replacement, feed into the autoclave. 150g of liquid ammonia was then heated to 200°C under a pressure of 10MPa, reacted at this temperature for 10h, then cooled to room temperature and filtered to remove insoluble solids, and the obtained liquid was rectified under reduced pressure to obtain 150g of unreacted raw material p-chlorotrifluorotoluene, And 102g of product p-trifluoromethylaniline. Unreacted raw materials can be recovered and recycled.

Embodiment 2

[0029] To the 3L autoclave, add 300g p-chlorotrifluorotoluene, 25g cuprous chloride, 10g copper powder, 90g sodium bicarbonate, 900g ethanol, seal the autoclave, and after three times of nitrogen replacement, feed 150g liquid ammonia into the autoclave , and then heated to 200°C under a pressure of 10MPa, reacted at this temperature for 12h, then cooled to room temperature and filtered to remove insoluble solids. The obtained liquid was rectified under reduced pressure to obtain 158g of p-chlorotrifluorotoluene and 92g of p-trifluoromethylaniline.

Embodiment 3

[0031] Into the 3L autoclave, add 300g p-chlorotrifluorotoluene, 2.5g cuprous chloride, 0.5g copper powder, 60g sodium hydroxide, 600g methanol, seal the autoclave, and after three times of nitrogen replacement, feed 240g into the autoclave The liquid ammonia was heated to 210°C and the pressure was 11MPa, and the reaction was carried out at this temperature for 12h, then cooled to room temperature and filtered to remove insoluble solids. The obtained liquid was rectified under reduced pressure to obtain 155g of p-chlorotrifluorotoluene, 95g of p-trifluoromethyl aniline.

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Abstract

The invention relates to a new method for preparing p-trifluoromethylaniline by performing high pressure ammonolysis. P-trifluoromethyl chlorobenzene serving as a raw material is subjected to high-temperature high pressure ammonolysis reaction in a solvent under the action of a catalyst, liquid ammonia and an acid-binding agent to generate p-trifluoromethyl phenylamine; the catalyst is a mixture of cuprous chloride and copper powder; the acid-binding agent is one or two of inorganic base mixtures of sodium hydroxide and the like, or one or two of organic base mixtures of pyridine and triethylamine; and the solvent is one or two of mixing solvents of methanol, ethanol, polyethylene glycol 300-3,000 and N,N-dimethylformamide. The method has the advantages that the inorganic base, serving as the acid-binding agent, with low cost and easy availability is adopted, the loss of liquid ammonia in the reaction process is greatly reduced, and the production efficiency is improved; and the catalyst can be prepared from organic solvents with the cost as low as that of ethanol and less harm, so that the generation of hydrolysis side reaction is avoided, the purity of the product is high and the quality is high; and raw materials without being totally reacted can be recycled.

Description

technical field [0001] The invention relates to a method for preparing p-trifluoromethylaniline by high-pressure ammonia hydrolysis, and belongs to the technical field of chemical material preparation. The method is suitable for the situation where p-chlorotrifluorotoluene is used as a raw material, and p-trifluoromethylaniline is prepared by high-pressure aminolysis in a solvent under the action of a catalyst, liquid ammonia and an acid binding agent. Background technique [0002] P-trifluoromethylaniline (p-trifluromethylaniline, abbreviated as PTFMA, CAS accession number is 455-14-1) is an important chemical raw material, especially widely used in pesticides and medicines. 2,6-dichloro-p-aminotrifluorotoluene can be obtained by chlorination of p-trifluoromethylaniline, which is an important intermediate. Special), cyflumethrin, flufenoxuron, herbicides buflunomide, butylenefluline, etc., are used in the pharmaceutical industry to synthesize new immunosuppressant drugs, s...

Claims

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Application Information

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IPC IPC(8): C07C211/52C07C209/10
Inventor 郑龙生李付香褚吉成
Owner JIANGSU FENGHUA CHEM IND
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