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Synthetic method of 1,1'-dicaprolactam disulfide

A technology of dithiodicaprolactam and caprolactam, which is applied to the synthesis of rubber vulcanizing agent 1,1'-dithiodicaprolactam (DTDC) and the synthesis field of 1,1'-dithiodicaprolactam, can solve the problem of product Low yield, complex material recovery process, waste of caprolactam, etc., to achieve the effect of simple production process, strong operability, and simple post-processing

Active Publication Date: 2019-08-20
SHANDONG YANGGU HUATAI CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The current DTDC synthesis technology uses caprolactam or other organic amines as acid-binding agents. There are problems such as long reaction time, a large amount of waste of caprolactam, complicated material recovery process, and difficult disposal of waste water generated.
For example, patent CN108658864A discloses a method for preparing rubber vulcanizing agent 1,1'-dithiobiscaprolactam. In this method, other organic amines such as triethylamine and pyridine are used instead of caprolactam as an acid-binding agent, and the acid-binding agent can be recycled. , to avoid a lot of waste of caprolactam, but the yield of the product obtained by this method is low, below 85%, and the acid-binding agent needs to be recovered through distillation, liquid separation and other operations, which increases the post-treatment process

Method used

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  • Synthetic method of 1,1'-dicaprolactam disulfide
  • Synthetic method of 1,1'-dicaprolactam disulfide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Add 200g of caprolactam to a 1L reactor and slowly raise the temperature to 130°C. At this time, the caprolactam is in a molten state. Turn on the stirring. Under the condition of 0.1MPa, the water in the system is pumped out under reduced pressure for about 10 minutes; the temperature is slowly raised to 140°C and 67.15 is added. g sodium hydroxide solid, continue to pump out the water generated by the reaction under the condition of 0.1MPa under reduced pressure. After about 30 minutes, no water is distilled out in the system and the liquid level of the system is calm and bubble-free. Pour out slowly and cool to room temperature , Store in a dry place for later use after crushing. If not enough, you can repeat this step to prepare more sodium caprolactam.

[0028] According to the same method as above, the solid sodium hydroxide is replaced with an equimolar solid potassium hydroxide to obtain the potassium caprolactam salt.

Embodiment 2

[0030] Add 80.42g of caprolactam sodium salt prepared in Example 1, 5.82g of caprolactam, 550g of 120# solvent naphtha into a 1L reaction kettle, control the temperature to 35°C, turn on the stirring, and slowly drop 38.32g of sulfur monochloride into the system, After about 2h, the dropwise addition of sulfur monochloride was completed, and the temperature was maintained to continue stirring for about 2.5h, and the reaction was completed. Add 200g of water for washing, stir for 15 minutes, filter with suction and then dry the filter cake to obtain 75.68g of white solid powder with a yield of 92.47%. The melting point is 132-136°C by DSC, which is measured by HPLC. The purity is 99.06%.

Embodiment 3

[0032] Add 89.41g of caprolactam sodium salt prepared in Example 1, 6.14g of caprolactam, 600g of 120# solvent naphtha into a 1L reaction kettle, control the temperature to 35°C, turn on the stirring, and slowly drop 42.53g of sulfur monochloride into the system, After about 2.5h, the dropwise addition of sulfur monochloride was completed. Keep the temperature and continue to stir for about 2.5h, and the reaction was completed. Add 200g of water for washing, stir for 15 minutes, filter with suction and then dry the filter cake to obtain 83.41g of white solid powder with a yield of 91.83%. The melting point is 133-137℃ by DSC, and it is measured by HPLC. The purity is 99.17%.

[0033] Regarding the recovery of caprolactam, the waste water containing caprolactam and sodium chloride produced by multiple reactions can be collected, concentrated, and then extracted with toluene for multiple times, and then distilled under reduced pressure to obtain caprolactam to complete the recovery...

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Abstract

The invention discloses a synthetic method of 1,1'-dicaprolactam disulfide. Caprolactam is used as an initiator, and sulfur monochloride and caprolactam inorganic salt are used as raw materials. Sulfur monochloride firstly reacts with caprolactam to form 1,1'-dicaprolactam disulfide and acid; caprolactam inorganic salt is continuously converted to caprolactam under the action of the acid formed bythe reaction; and caprolactam continuously reacts with sulfur monochloride to form 1,1'-dicaprolactam disulfide. According to the method, there is no need to add other types of acid-binding agents, and the raw material caprolactam can be synthesized by itself in the reaction process. The production technology is simple, has strong operationality and simple post-treatment, and has industrial application value. The product is white solid powder in the appearance, and the yield is 88% and above, the purity is 99% and above. The product meets the use requirements.

Description

Technical field [0001] The invention relates to a method for synthesizing rubber vulcanizing agent 1,1'-dithiodicaprolactam (DTDC), in particular to a method for synthesizing 1,1'-dithiodicaprolactam with low cost and little caprolactam waste. It belongs to the technical field of rubber additives synthesis. Background technique [0002] Rubber is currently widely used in our daily life, medical industry, rail transit industry and other industries, and has an irreplaceable role in people's lives. Natural rubber and synthetic rubber are widely used in the current society and life, and with the continuous development of the economy, the demand for rubber in all walks of life is also increasing. 1,1'-Dithiodicaprolactam (DTDC) is an important rubber vulcanization accelerator. Compared with the vulcanizing agent DTDM, DTDC has attracted attention because it does not produce nitrosamines during the vulcanization process. It can Replace all or part of sulfur to form an effective or se...

Claims

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Application Information

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IPC IPC(8): C07D223/10
CPCC07D223/10
Inventor 马德龙王庆振马松王才朋潘琳琳冉升亮孟祥克
Owner SHANDONG YANGGU HUATAI CHEM
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