Method for continuously preparing n,n'-bis(1,4-dimethylpentyl)-p-phenylenediamine

A technology of dimethylpentyl and p-phenylenediamine, applied in chemical instruments and methods, preparation of amino compounds, preparation of organic compounds, etc., can solve problems such as difficulties in recycling aliphatic ketones, low catalyst cost, and difficulties in recycling , to achieve the effect of saving labor costs, reducing labor intensity, reducing recycling and disposal costs

Active Publication Date: 2018-09-25
CHINA PETROCHEMICAL CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Using precious metals such as palladium or platinum as catalysts is costly and difficult to recycle. 5-10% of aliphatic ketones are converted into fatty alcohols in the presence of catalysts (hydrogenation reaction), and the product consumes a lot of aliphatic ketones. Add new catalysts and equipment
Using copper or nickel as the catalyst, the catalyst cost is low and can be used for a long time, but 80-95% of aliphatic ketones are converted into fatty alcohols in the presence of catalysts, and the recycling of aliphatic ketones is difficult

Method used

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  • Method for continuously preparing n,n'-bis(1,4-dimethylpentyl)-p-phenylenediamine
  • Method for continuously preparing n,n'-bis(1,4-dimethylpentyl)-p-phenylenediamine
  • Method for continuously preparing n,n'-bis(1,4-dimethylpentyl)-p-phenylenediamine

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The present embodiment includes the following 4 consecutive steps:

[0033] (1) To the reactor 1, according to the molar ratio of p-nitroaniline, 5-methyl-2-hexanone and acid is 1:4.5:0.008, continuously add, maintain the temperature of the reactor 1 at 120-125 ℃, and the mixed material is in the reaction The vessel 1 overflowed after staying for 1 hour, and the material 1 was obtained.

[0034] (2) Material 1 is continuously fed into still 1, unreacted 5-methyl-2-hexanone and water are extracted from the upper part of still 1, and the lower part of still 1 is continuously extracted to obtain material 2. After 24 hours, still 1 is taken Samples taken from the upper part, gas spectrum detection and analysis, the content of 5-methyl-2-hexanone is 92.33%, 5-methyl-2-hexanol is not detected, N,N'-bis(1,4-dimethyl pentyl) p-phenylenediamine was not detected.

[0035] (3) material 2 is continuously transported into the reactor 2 equipped with solid palladium-carbon catalyst...

Embodiment 2

[0038] The operating conditions are the same as in Example 1, but the acid used in step (1) is p-toluenesulfonic acid, and the catalyst used in step (3) is a reduced copper-based catalyst (CuO33W%, Cr 2 O 3 12W%, Al 2 O 3 , 55W%).

[0039] Results: The upper part of the distillation kettle 1 obtained in step (2) was sampled, and the gas spectrum detection and analysis showed that the content of 5-methyl-2-hexanone was 92.43%, 5-methyl-2-hexanone was not detected, N, N'-bis(1,4-dimethylpentyl)-p-phenylenediamine was not detected.

[0040]In step (3), reaction solution 3 is obtained. Gas spectrometry analysis, the content of 5-methyl-2-hexanone is 0.64%, 5-methyl-2-hexanol is 0.13%, N,N'-bis(1,4-dimethylpentyl)p-benzene Diamine content 95.01%.

[0041] The finished product obtained in step (4) was tested, and no p-nitroaniline was detected, and the content of N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine was 99.14%.

Embodiment 3

[0043] The operating conditions are the same as in Example 1, but the hydrogen pressure in step (3) is 2.0 MPa, and the residence time of the material in the reactor 2 is 1.5 h.

[0044] Results: The upper part of the distillation kettle 1 obtained in step (2) was sampled, and the gas spectrum detection and analysis showed that the content of 5-methyl-2-hexanone was 92.43%, 5-methyl-2-hexanone was not detected, N, N'-bis(1,4-dimethylpentyl)-p-phenylenediamine was not detected.

[0045] In step (3), reaction solution 3 is obtained. Gas spectrometry analysis, the content of 5-methyl-2-hexanone is 0.44%, 5-methyl-2-hexanol is 0.05%, N,N'-bis(1,4-dimethylpentyl)p-benzene The diamine content is 96.01%.

[0046] In the finished product obtained in step (4), no p-nitroaniline was detected, and the content of N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine was 99.70%.

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Abstract

A continuous preparation method of N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine includes the steps of: 1) performing a reaction to p-nitroaniline or p-phenylenediamine with 5-methyl-2-hexanone and acid in a first reactor to obtain a first material; 2) feeding the first material into a first distillation kettle, and withdrawing 5-methyl-2-hexanone from the top of the distillation kettle and withdrawing a kettle liquid to obtain a second material; 3) feeding the second material into a second reactor, in which palladium, platinum, nickel or the like solids or a supported catalyst thereof is disposed, and feeding hydrogen to perform a reaction to obtain a third reaction solution; and 4) feeding the third reaction solution into a second distillation kettle to perform distillation to obtain the N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine. The method can avoid a phenomenon that a large amount of alcohol is converted into ketones, which commonly exists in one-step reaction in a kettle reactor a fixed bed reactor, and greatly reduces recovery and treatment cost of the raw material ketone, thereby reducing material consumption and energy consumption.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and relates to a method for continuously preparing N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine by avoiding the conversion of raw material fatty ketones into fatty alcohols. Energy-efficient and efficient preparation process. Background technique [0002] N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine, commonly known as antioxidant 4030, is a high-efficiency anti-ozone antioxidant, mainly used in rubber compounds that work under static conditions for a long time. Such as aviation tires, engineering tires, agricultural equipment tires and vehicle structural brackets, fixed hoses, sealing strips, etc.; due to its excellent anti-ozone function, it is widely used as a stabilizer for colored solution-polymerized and emulsion-polymerized elastomers, such as some synthetic rubbers and elastomer stabilizers. In addition, the product is a liquid product, which is easy to disperse and facilitate rubber ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/78C07C211/51
CPCC07C209/78C07C211/51
Inventor 韦志强王天慧付春黄伟郁铭孙阿沁
Owner CHINA PETROCHEMICAL CORP
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