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Method for preparing p-aminodiphenylamine

A technology of p-aminodiphenylamine and nitrodiphenylamine, which is applied in the field of preparation of p-aminodiphenylamine, can solve problems such as difficult solvent recovery, long hydrogenation time, and hydrogenation of azobenzene, so as to avoid the control of moisture content, Simple operation and improved reaction efficiency

Active Publication Date: 2012-02-08
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

CN 1721390A mentions the use of nickel-aluminum alloy powder, CN 1207265C uses skeleton nickel catalyst for hydrogenation, and there are problems such as long hydrogenation time and difficult solvent recovery; CN 1167655C mentions hydrogenation with noble metal catalyst, but the azobenzene in the condensation product cannot be added Hydrogen, the by-product azobenzene needs to be separated, and hydrogenation is converted into aniline, which increases the cost

Method used

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  • Method for preparing p-aminodiphenylamine

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Example 1. 50g of powdered activated carbon was pretreated, soaked in 200g of 3% nitric acid solution at 30°C for 8 hours, washed with deionized water until neutral, then soaked in 3% hydrogen peroxide solution for 4 hours, washed, and dried at 105°C for 16 hours.

[0030] Get the treated activated carbon 20g for later use. Dissolve a certain amount of palladium chloride and lanthanum nitrate in 100mL of 2% hydrochloric acid solution, pour it into a container filled with carrier activated carbon, stir for 4 hours, take it out, add 10mL of 5% formaldehyde for reduction, and use 5% sodium hydroxide The pH of the solution was adjusted to 6-8, maintained for 4 hours, taken out, washed with deionized water, and vacuum-dried at 80°C for 8 hours to obtain the finished catalyst, which was designated as Cat1.

Embodiment 2

[0031] Example 2. 50g of powdered activated carbon was pretreated, soaked in 200g of 3% hydrochloric acid solution at 60°C for 8 hours, washed with deionized water until neutral, soaked in 5% hydrogen peroxide solution for 4 hours, washed, and dried at 105°C for 16 hours.

[0032] Get the treated activated carbon 20g for later use. Dissolve a certain amount of palladium nitrate and cerium nitrate in 100ml of 2% nitric acid solution, pour it into a container filled with carrier activated carbon, stir for 5 hours, take it out, add 10ml of 5% hydrazine hydrate for reduction, and use 5% sodium hydroxide The pH of the solution was adjusted to 6-8, maintained for 4 hours, taken out, washed with deionized water, and vacuum-dried at 80°C for 8 hours to obtain the finished catalyst, which was designated as Cat2.

Embodiment 3-6

[0033] Example 3-6. The catalyst was prepared by the method of Example 1, and the contents of each component were shown in the table.

[0034] Table 1 The content of each component in the catalyst

[0035] Example catalyst palladium rare earth element 1 Cat1 5% (added in the form of palladium chloride) La (added in the form of lanthanum nitrate) 0.05% 2 Cat2 7% (added in the form of palladium nitrate) La (added in the form of lanthanum chloride) 0.70% 3 Cat3 9% (added in the form of palladium acetate) Ce (added in the form of cerium chloride) 0.18% 4 Cat4 11% (added in the form of palladium chloride) Pr (added in the form of praseodymium chloride) 0.33% 5 Cat5 13% (added in the form of palladium nitrate) Nd (added as neodymium chloride) 0.65% 6 Cat6 15% (added in the form of palladium acetate) Sm (added as samarium chloride) 0.90%

[0036] Above-mentioned embodiment 1-6 is the preparation of h...

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Abstract

Belonging to the technical field of organic synthesis, the invention relates to a method for preparing p-aminodiphenylamine with aniline and nitrobenzene. The method comprises the steps of: adding a phase transfer catalyst and inorganic base in the form of solid into a reaction system, subjecting nitrobenzene and aniline to a condensation reaction for 2-24h at a temperature of 60-150DEG C so as to generate 4-nitrodiphenylamine and 4-nitrosodiphenylamine of high selectivity, then subjecting the 4-nitrodiphenylamine and 4-nitrosodiphenylamine to hydrogenation with the presence of a Pd / C catalyst, thus obtaining p-aminodiphenylamine. The Pd / C catalyst is prepared in the processes of: pretreating the activated carbon carrier by acid treatment and oxidation treatment; adding a rare earth metal into the active component palladium (Pd); employing an immersion adsorption technology; adjusting the pH with a sodium hydroxide solution and maintaining the pH at 6-8 for reduction and washing, and drying, thus obtaining the finished product of catalyst. With the method provided in the invention, high purity RT base can be prepared.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and relates to a preparation method of p-aminodiphenylamine. Background technique [0002] p-Aminodiphenylamine is an important antioxidant and stabilizer intermediate, and an important chemical product in the rubber industry and polymer industry. According to the different raw materials used, the current industrial production methods of 4-aminodiphenylamine include: diphenylamine method, aniline method, formanilide method, and nitrobenzene method. Compared with several other methods, the nitrobenzene method has the advantages of less three wastes and less by-products. The research hotspots mainly focus on the selection of condensation catalysts and hydrogenation catalysts. [0003] CN1307556A mentions that the catalyst used in the condensation process is usually tetraalkylammonium hydroxide, such as tetramethylammonium hydroxide, tetrapropylammonium hydroxide, trimethylbenzylammonium h...

Claims

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Application Information

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IPC IPC(8): C07C211/55C07C209/36C07C209/38
Inventor 李玉杰孙盛凯季峰崎金汉强黄伟
Owner CHINA PETROLEUM & CHEM CORP
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