Method for preparing N,N'-bi(alkyl)-p-phenylenediamine

A technology of p-phenylenediamine and alkyl, applied in the field of preparation of N,N'-bis-p-phenylenediamine, which can solve the problems of harsh preparation conditions and low yield

Active Publication Date: 2017-07-18
JIANGSU SINORGCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The present invention aims to provide a preparation method of N,N'-bis(alkyl)-p-phenylenediamine, to solve the preparation method of N,N'-bis(alkyl)-p-phenylenediamine in the prior art Technical problems with harsh conditions and low yield

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  • Method for preparing N,N'-bi(alkyl)-p-phenylenediamine

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[0024] As described in the background art section, the existing preparation method of N,N'-bis(alkyl)-p-phenylenediamine has harsh conditions and low yield. In order to solve this problem, the present invention provides a preparation method of N,N'-bis(alkyl)-p-phenylenediamine, which comprises the following steps: mixing raw material A and raw material B and reacting to obtain a reaction liquid, The reaction solution is dehydrated to obtain a Schiff base intermediate; hydrogen is introduced into the Schiff base intermediate, and a reduction reaction is carried out under the catalysis of a supported nanocomposite metal catalyst to obtain N,N'-bis(alkyl )-p-phenylenediamine; Wherein, raw material A is p-phenylenediamine and / or p-nitroaniline, and raw material B is alkyl ketone.

[0025] The above preparation method provided by the present invention adopts a two-step method to prepare N,N'-bis(alkyl)-p-phenylenediamine, specifically: first, p-phenylenediamine or p-nitroaniline a...

Embodiment 1

[0037] In this example, a supported nanocomposite metal catalyst Cu-Pd / TiO was prepared 2 (where TiO 2 For catalyst carrier, Pd and Cu are respectively the first active component and the second active component), and the preparation method is as follows:

[0038] Weigh 10 g of nanocrystalline titanium dioxide, add 150 ml of deionized water to stir, and prepare a slurry at a temperature of 80° C. after heating in a water bath. Slowly add 10ml of Cu(NO 3 ) 2 solution (Cu content is 0.27g / ml) and 6ml of H 2 PdCl 4 solution (Pd content is 0.01g / ml), stirring and impregnating at constant temperature for 5h. Then, NaOH solution with a mass concentration of 10% was added dropwise to the mixed solution, the pH value was adjusted to be between 8 and 10, and the temperature of the solution was kept and stirred for another 5 hours. Then filter the reaction solution, wash the filter cake with deionized water until neutral, vacuum dry at 90-150°C for 2 hours, then vacuum roast at 200...

Embodiment 2 to 5

[0040] All prepared supported nanocomposite metal catalyst Cu-Pd / TiO in this embodiment 2 , the process condition of preparation is the same as embodiment 1, and difference is the ratio and particle diameter of catalyst support, first active ingredient and second active ingredient, and concrete ratio is as follows:

[0041]

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Abstract

The invention discloses a method for preparing N,N'-bi(alkyl)-p-phenylenediamine. The method comprises the following steps: mixing a raw material A and a raw material B to react to obtain a reaction liquid, and performing dehydration treatment on the reaction liquid so as to obtain a Schiff base intermediate; and introducing hydrogen into the Schiff base intermediate, and performing reduction reaction under the catalysis action of a loaded nano composite metal catalyst, thus obtaining the N,N'-bi(alkyl)-p-phenylenediamine, wherein the raw material is p-phenylenediamine and / or paranitroaniline; and the raw material B is alkyl ketone. The method disclosed by the invention has the advantages of being gentle in reaction condition, high in selectivity, easy in reaction control, easy in product separation and high in yield, and industrial production is easily achieved.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of N,N'-bis(alkyl)-p-phenylenediamine. Background technique [0002] P-phenylenediamine antiaging agent is a kind of rubber antiaging agent with excellent performance, which is widely used in tires, tapes and other industrial rubber products. At present, the p-phenylenediamine antiaging agents sold on the market include N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (6PPD) and N-isopropyl-N' - Phenyl-p-phenylenediamine (IPPD), etc., all of which have good anti-oxidation, anti-ozone, anti-bending, anti-cracking, anti-heat aging and other properties. [0003] Among the phenylenediamine antiaging agents, N, N'-bis(alkyl) substituted p-phenylenediamine is an important class. For example, N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine (rubber anti-aging agent 77PD, also known as anti-aging agent 4030), is a new type of anti-ozone protection additive, its st...

Claims

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Application Information

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IPC IPC(8): C07C209/26C07C211/50
CPCC07C209/26C07C249/02C07C211/50C07C251/08
Inventor 陈新民李春生
Owner JIANGSU SINORGCHEM TECH CO LTD
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