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Production method of n-(cyclohixylthio) phthalimide

A technology of phthalimide and cyclohexylthio, which is applied in the field of manufacturing N-phthalimide and N-phthalimide, can solve difficult, tetrachloro To avoid the carcinogenicity of carbon dioxide and other problems, achieve the effect of high yield and high productivity

Inactive Publication Date: 2006-12-20
TORAY FINE CHEMICALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, chlorinated hydrocarbons have a very large adverse effect on the environment, especially carbon tetrachloride has carcinogenicity, is a harmful substance in the Water Pollution Prevention Act, and is also a marine pollutant, an ozone layer depleting substance, etc. Problems with use as a solvent in industry

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] An example using a mixed solvent of 15% by weight of toluene and 85% by weight of cyclohexane will be described.

[0057] Into a 500 mL glass flask equipped with a stirrer and a thermometer, 127 g of a mixed solvent of 87 g of dicyclohexyl disulfide (purity 94%, 0.35 mol) and toluene (boiling point 111° C.) / cyclohexane (boiling point 81° C.) was added ( Toluene 15% by weight, density 0.79 g / mL, 160 mL), and cooled to -20°C with a cooling medium. Stir it, while blowing in 20mL (30g, 0.43mol) of chlorine that has been taken into the glass gas collector at the liquid temperature of -20~-10°C for 1.5 hours to chlorinate dicyclohexyl disulfide , a solution of cyclohexylsulfanyl chloride (0.70 mol) was obtained.

[0058] Then, 103 g (0.70 mol) of phthalimide, 129 mL (93 g, 0.92 mol) of triethylamine, and toluene / cyclohexane were added to a 1 L glass flask equipped with a stirrer, a thermometer, and a baffle. 127 g of a solvent (15% by weight of toluene) was heated to 60° C....

Embodiment 2

[0088] An example using a mixed solvent of 50% by weight of toluene and 50% by weight of cyclohexane will be described.

[0089] In the synthesis of dicyclohexyl disulfide and the synthesis solvent of N-(cyclohexylthio)phthalimide, 131 g of a mixed solvent of toluene / cyclohexane (toluene 50% by weight, density 0.82 g / mL, 160mL), except that, react in the same manner as in Example 1, and carry out post-treatment.

[0090] The liquid surface of the reaction mixture was rotated evenly, and the mixing state of the slurry was always good.

[0091] While stirring the oil layer remaining in the post-treatment, it was cooled to 10°C, and N-(cyclohexylthio)phthalimide was crystallized. The crystals were filtered and dried to obtain 121g of product (purity 97%, N-(cyclohexylthio)phthalimide content 117g, 0.45 mole) and 329g crystallization mother liquor (N-(cyclohexylthio) generation) phthalimide content 40g, 0.15 moles). The total yield of N-(cyclohexylthio)phthalimide relative to ...

Embodiment 3

[0094] An example using a mixed solvent of 20% by weight of toluene and 80% by weight of cyclohexane will be described.

[0095] In the synthesis of dicyclohexyl disulfide and the synthesis solvent of N-(cyclohexylthio)phthalimide, 127 g of a mixed solvent of toluene / cyclohexane (toluene 20% by weight, density 0.79 g / mL, 160mL), except that, react in the same manner as in Example 1, and carry out post-treatment.

[0096] The liquid surface of the reaction mixture was rotated evenly, and the mixing state of the slurry was always good.

[0097] While stirring the oil layer remaining in the post-treatment, it was cooled to 10°C, and N-(cyclohexylthio)phthalimide was crystallized. The crystals were filtered and dried to obtain 158g of product (purity 99%, N-(cyclohexylthio)phthalimide content 156g, 0.60 mole) and 280g crystallization mother liquor (N-(cyclohexylthio) Generation) phthalimide content 9g, 0.03 moles). The total yield of N-(cyclohexylthio)phthalimide relative to p...

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Abstract

One process of producing N-(cyclohexyl thio) phthalimide is provided, which uses hydrocarbon chloride and similar environment harming solvent and has high industrial yield and high production efficiency. The process of producing N-(cyclohexyl thio) phthalimide features the first synthesis of cyclohexyl sulfenyl chloride in the mixed solvent of aromatic hydrocarbon and saturated hydrocarbon and the subsequent reaction between the cyclohexyl sulfenyl chloride and phthalimide in the mixed solvent of aromatic hydrocarbon and saturated hydrocarbon.

Description

technical field [0001] The present invention relates to a method for producing N-(cyclohexylthio)phthalimide, a compound useful as a vulcanization retarder in a rubber vulcanization process. More specifically, it relates to an industrially advantageous method for producing N-(cyclohexylthio)phthalimide, which has little impact on the environment. Background technique [0002] Generally, N-(cyclohexylthio)phthalimide is produced by reacting cyclohexylthio chloride and phthalimide in the presence of a base. In this production method, first, cyclohexylsulfenyl chloride is synthesized under strongly acidic conditions using chlorine, and then cyclohexylsulfenyl chloride and phthalimide are condensed under strongly basic conditions. Therefore, a method of using solvents with different properties in the respective reactions is conceivable, but the method of using two types of solvents with different properties is industrially disadvantageous. Therefore, as a solvent stable under ...

Claims

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Application Information

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IPC IPC(8): C07D209/48
Inventor 西村一明冈田勇雄
Owner TORAY FINE CHEMICALS CO LTD
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