Preparation method of dicyclohexyldisulfide

A technology of dicyclohexyl disulfide and sodium disulfide, which is applied in the preparation of hydrogenated polysulfide/polysulfide, organic chemistry, etc., and can solve problems such as impact, harsh environment, and river pollution

Active Publication Date: 2007-11-14
TORAY IND INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the waste liquid generated in the production process contains a large amount of sulfides, organic substances, sodium chloride, etc., and the bad smell and serious coloring of the waste liquid are serious problems.
In addition, since the waste liquid generated in the prod...

Method used

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Examples

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preparation example Construction

[0008] In the production method of dicyclohexyl disulfide of the present invention, when sodium disulfide and chlorocyclohexane are reacted, an aqueous solvent is used. The aqueous solvent is preferably an aqueous solvent. In order to make the mixed state of chlorocyclohexane and sodium disulfide in the water solvent favorable, the water-containing solvent may use a hydrophilic solvent other than water together with water. Alcohol is preferably used as the hydrophilic solvent. More preferably methanol is used.

[0009] The amount of the aqueous solvent used is usually 0.1 to 10 times by weight, preferably 0.5 to 5 times by weight, based on the chlorocyclohexane. When an aqueous solvent is used in the range of 0.1 to 10 times by weight relative to chlorocyclohexane, the yield and productivity of dicyclohexyl disulfide are high.

[0010] When alcohol is used as the hydrophilic solvent, the alcohol content is preferably 90% by weight or less, more preferably 20 to 80% by weigh...

Embodiment 1

[0047] 150g of 60% by weight sodium sulfide (60g of crystal water, 90g of sodium sulfide, 1.15 moles (molecular weight: 78.1)), 30g of sulfur (0.94 moles (atomic weight: 32.1)), 120g of methanol, and 100g of water were added to a 1L autoclave (AUTOCLAVE). , heated at 70°C and gauge pressure 80kPa for 1 hour to prepare sodium disulfide. After cooling, open the autoclave, add 250 g of 95% by weight of chlorocyclohexane (237 g of chlorocyclohexane, 2.00 moles (molecular weight: 118.6)) (650 g in total), and heat the reaction at 100 ° C and a gauge pressure of 180 kPa 11 hours. After cooling, the insoluble matter by-produced in the primary reaction was removed by filtration from the reaction mixture, which contained by-produced sodium chloride, and washed with 5 mL of methanol to obtain 120 g of insoluble matter.

[0048] Then, the filtrate was separated into 280 g of the first reacted water layer and 228 g of the oil layer. The water layer has a strong stench of sulfur compound...

Embodiment 2

[0062] In the same manner as in Example 1, the mixture solution of the by-produced insolubles in the initial reaction and the second reaction was prepared, and after adding 10 mL of n-hexane and fully mixing, the wastewater layer was black-green and translucent during liquid separation. The measured CODMn (oxygen consumption of potassium permanganate) was 4000ppm. 1 g of 30% by weight hydrogen peroxide was added to this waste water with stirring at room temperature. After a few minutes, the waste water became colorless and transparent. The stench of sulfur compounds disappears, the CODMn (oxygen consumption of potassium permanganate) is 800ppm, and the CODMn (oxygen consumption of potassium permanganate) of wastewater can be reduced to less than 1 / 5. In addition, the n-hexane oil layer after liquid separation can be used as fuel.

[0063] As described above, by-produced insoluble matter can be used as waste water with little adverse effect on the environment.

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Abstract

The invention provides a preparation method of dicyclohexyl disulphide without harm for environment. Sodium disulfide and chlorocyclohexane react by hydrosolvent to obtain dicyclohexyl disulphide, insoluble is exhausted from the mixture, and separates oil layer and leaves a part of or whole of water layer for the reaction of sodium disulfide and chlorocyclohexane.

Description

technical field [0001] The present invention relates to a preparation method of dicyclohexyl disulfide, which is a useful compound used as a raw material of rubber anti-scorch agent for tires and the like. More specifically, the present invention relates to a method for producing dicyclohexyl disulfide which has no adverse effect on the environment and is industrially advantageous. Background technique [0002] In general, as an industrial production method of dicyclohexyl disulfide, there is a method of reacting sodium disulfide and chlorocyclohexane. In this production method, in order to dissolve sodium disulfide for the reaction, an aqueous solvent is generally used. In order to increase the yield, there is a method of coexisting an alcohol or an alkali metal hydroxide (see Patent Document 1). This method has achieved very excellent results in improving productivity. However, the waste liquid generated in the production process contains a large amount of sulfides, org...

Claims

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Application Information

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IPC IPC(8): C07C321/22C07C319/22
Inventor 西村一明冈田勇雄
Owner TORAY IND INC
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