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Catalytic synthesis method of diphenylamine compound

A technology of phenolic compounds and synthesis methods, applied in chemical instruments and methods, metal/metal oxide/metal hydroxide catalysts, physical/chemical process catalysts, etc. Long route and other problems, to achieve the effect of convenient operation, high product yield and simple process

Inactive Publication Date: 2012-09-19
SHANGHAI LUCKY BIOLOGICAL & CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Although these synthetic methods are mature and widely used, they all have the disadvantages of long process route, complex process, low product yield and high discharge of three wastes.

Method used

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  • Catalytic synthesis method of diphenylamine compound
  • Catalytic synthesis method of diphenylamine compound

Examples

Experimental program
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Embodiment 1

[0024] With 93g (1.0mol) aniline, 470g (5.0mol) phenol, 9.8g (0.1mol) cyclohexanone, 10g5% palladium carbon (water content 60%) is placed in 1000ml autoclave, after nitrogen replacement, slowly heat up to 190 React at ℃ for 5 hours, cool to 60℃, filter the catalyst, wash the catalyst with water, and distill the filtrate under reduced pressure to recover unreacted phenol and cyclohexanone, and finally collect 159.7 g of diphenylamine, with a yield of 94.5%.

Embodiment 2

[0026] Put 107g (1.0mol) of o-toluidine, 470g (5.0mol) of phenol, 9.8g (0.1mol) of cyclohexanone, and 10g of 5% palladium carbon (60% water content) in a 1000ml autoclave, and slowly heat up after nitrogen replacement React at 200°C for 5 hours, cool to 60°C, filter the catalyst, and wash the catalyst with water before use. The filtrate was distilled under reduced pressure to recover unreacted phenol and cyclohexanone, and finally 175.9 g of 2-methyldiphenylamine was collected, with a yield of 96.1%.

Embodiment 3

[0028] 137g (1.0mol) 2-methyl-4-methoxyaniline, 470g (5.0mol) phenol, 9.8g (0.1mol) cyclohexanone, 10g 5% palladium carbon (water content 60%) are placed in 1000ml autoclave , after nitrogen replacement, slowly raise the temperature to 200°C-210°C to react for 6 hours, cool to 60°C, filter the catalyst, wash the catalyst with water before use. The filtrate was distilled under reduced pressure to recover unreacted phenol and cyclohexanone, and finally 198.7 g of 2-methyl-4-methoxydiphenylamine was collected, with a yield of 93.3%.

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Abstract

Disclosed is a catalytic synthesis method of a diphenylamine compound. According to the catalytic synthesis method, through a condensation-dehydrogenation-hydrogenation process in a system, an aniline compound and a phenol compound are directly synthesized into the diphenylamine compound under a high temperature and high pressure condition and in the presence of catalytic amount of cyclohexanone and metal catalyst. The catalytic synthesis method has the advantages of being simple in process, low in cost, high in yield of products, few in side reactions and suitable for industrial production.

Description

Technical field: [0001] The invention belongs to the field of organic chemistry, relates to the research of organic synthesis methods, and provides a simple and convenient synthesis method of diphenylamine compounds. Background technique: [0002] Diphenylamine compounds are basic organic chemical intermediates, which can be widely used in the synthesis of fine chemicals such as medicines, pesticides, dyes, etc., especially 2-methyl-4-methoxyaniline, as a benzofuran-type heat and pressure sensitive color It is the core intermediate of the agent, and the research on its synthesis method has been widely concerned. At present, the main synthetic methods of such compounds at home and abroad are as follows: [0003] [0004] Although these synthetic methods are mature in technology and widely used, they all have the disadvantages of long process route, complex process, low product yield and high discharge of three wastes. [0005] The present invention strives to provide a s...

Claims

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Application Information

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IPC IPC(8): C07C211/55C07C211/54C07C209/28B01J23/755B01J23/75B01J23/42B01J23/44B01J23/46
Inventor 罗纲张少刚杜军季成君张先南
Owner SHANGHAI LUCKY BIOLOGICAL & CHEM TECH