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Continuous preparation method of N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine

A technology of dimethylpentyl and p-phenylenediamine, which is applied in the field of energy-saving and high-efficiency preparation technology, can solve the problems of difficulty in recycling aliphatic ketones, difficulty in recycling and utilization, and high consumption of aliphatic ketones, saving labor costs and reducing recycling and utilization. and processing costs, the effect of reducing labor intensity

Active Publication Date: 2017-04-05
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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  • Continuous preparation method of N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine
  • Continuous preparation method of N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The present embodiment comprises 4 steps that carry out continuously as follows:

[0033] (1) Continuously add p-nitroaniline, 5-methyl-2-hexanone and acid into reactor 1 at a molar ratio of 1:4.5:0.008, maintain the temperature of reactor 1 at 120-125°C, and the mixed material is reacting The device 1 overflowed after staying for 1 h, and the material 1 was obtained.

[0034] (2) Material 1 enters still 1 continuously, unreacted 5-methyl-2-hexanone and water are extracted from the upper part of still 1, and the lower part of still is continuously extracted to obtain material 2. After 24 hours, take still 1 The upper sample was collected and analyzed by gas spectrometry. The content of 5-methyl-2-hexanone was 92.33%, 5-methyl-2-hexanol was not detected, and N,N'-bis(1,4-dimethyl Amyl amyl) p-phenylenediamine was not detected.

[0035] (3) The material 2 is continuously transported into the reactor 2 equipped with solid palladium-carbon catalyst, and at the same time, ...

Embodiment 2

[0038] Operating condition is the same as embodiment 1, but the used acid of step (1) is p-toluenesulfonic acid, and the used catalyzer of step (3) is the copper series catalyst that has been reduced (CuO33W%, Cr 2 o 3 12W%, Al 2 o 3 ,55W%).

[0039] Result: The sample from the upper part of the still 1 obtained in step (2) was detected and analyzed by gas chromatography. The content of 5-methyl-2-hexanone was 92.43%, and 5-methyl-2-hexanone was not detected. N, N'-bis(1,4-dimethylpentyl)-p-phenylenediamine was not detected.

[0040]Step (3) to obtain the reaction solution 3. Gas spectrum detection and 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-phenyl The diamine content is 95.01%.

[0041] The finished product obtained in step (4) was tested, but p-nitroaniline was not 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 2.0MPa, and the residence time of the material in the reactor 2 is 1.5h.

[0044] Result: The sample from the upper part of the still 1 obtained in step (2) was detected and analyzed by gas chromatography. The content of 5-methyl-2-hexanone was 92.43%, and 5-methyl-2-hexanone was not detected. N, N'-bis(1,4-dimethylpentyl)-p-phenylenediamine was not detected.

[0045] Step (3) to obtain the reaction solution 3. Gas spectrum detection and 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-phenyl The diamine content is 96.01%.

[0046] The finished product obtained in step (4) was tested, but p-nitroaniline was not 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 chemical industry, and relates to a method for continuously preparing N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine which avoids the conversion of aliphatic ketones into fatty alcohols. Energy-saving and efficient preparation process. Background technique [0002] N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine is commonly known as anti-aging agent 4030. It is a high-efficiency anti-ozone anti-aging agent. It is mainly used in rubber materials that work under static conditions for a long time. Such as aviation tires, engineering tires, agricultural equipment tires and vehicle structural supports, 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, this product is a liquid product, which is easy to disperse and...

Claims

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Application Information

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Patent Type & Authority Applications(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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