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Process for the production of a sulfone monomer

A kind of technology of diphenyl sulfone and dichlorodiphenyl sulfone, which is used in the field of preparing sulfone monomers

Inactive Publication Date: 2012-08-15
H R 班多德卡尔 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this process is the excessive use of dimethyl sulfate resulting in the toxic by-product diethyl pyrosulfate

Method used

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  • Process for the production of a sulfone monomer
  • Process for the production of a sulfone monomer
  • Process for the production of a sulfone monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0188] To prepare crude 4,4'-dichlorodiphenylsulfone, add sulfur trioxide to dimethyl sulfate in step 1.

[0189] 400 g of sulfur trioxide was added to 315 g of dimethyl sulfate over about 1 hour while maintaining the reaction mixture at 28°C-30°C for 30 minutes, followed by the addition of 1.0 g of boric acid and allowed to react for 30 minutes. The reaction mixture was added to 562 g of monochlorobenzene at 30°C-35°C over about 1 hour and held for 1 hour.

[0190] The reaction mixture was then added to 600 g of isopropanol to precipitate 4,4'-dichlorodiphenylsulfone. The precipitate was isolated and neutralized with caustic soda and washed repeatedly with water and dried to obtain 577 g of product (APHA 217). The yield was 80.4% relative to monochlorobenzene. HPLC analysis showed that the product composition was 98.99% of 4,4'-dichlorodiphenylsulfone, 0.39% of 3,4'-isomer and 0.68% of 2,4'-isomer. The yield of 4,4'-dichlorodiphenyl sulfone was 79.5% relative to monochloro...

Embodiment 2

[0192] Crude 4,4'-dichlorodiphenylsulfone was purified using a chelating agent.

[0193] 577 g of crude 4,4'-dichlorodiphenylsulfone was dissolved in a 1:1 mixture of 1160 g of chlorobenzene and water at 85°C-95°C. The resulting solution was treated with 1.2 g of chelating agent and the aqueous layer was separated. This step was repeated and the solvent layer was filtered off at 85°C-95°C. The filtrate was cooled to 30 °C to precipitate pure 4,4'-dichlorodiphenylsulfone, separated and washed with water and dried to obtain 542 g of product (APHA 8). The yield was 75.6% relative to monochlorobenzene. HPLC analysis showed that the product composition was 99.86% of 4,4'-dichlorodiphenylsulfone, 0.063% of 3,4'-isomer and 0.058% of 2,4'-isomer. The yield of 4,4'-dichlorodiphenyl sulfone was 75.5% relative to monochlorobenzene.

Embodiment 3

[0195] The crude 4,4'-dichlorodiphenylsulfone was purified by activated charcoal.

[0196] 400 g of sulfur trioxide was added to 315 g of dimethyl sulfate over about 1 hour while maintaining the reaction mixture at 28°C-30°C for 30 minutes, followed by the addition of 1.0 g of boric acid and allowed to react for 30 minutes. The reaction mixture was added to 562 g of monochlorobenzene at 30°C-35°C over about 1 hour and held for 1 hour.

[0197] The reaction mixture was then added to 600 g of isopropanol to precipitate 4,4'-dichlorodiphenylsulfone. The precipitate was isolated and neutralized with caustic soda and washed repeatedly with water and dried to obtain 570 g of product (APHA 237). The yield was 79.5% relative to monochlorobenzene. HPLC analysis showed that the product composition was 98.53% 4,4'-dichlorodiphenylsulfone, 0.40% 3,4'-isomer and 1.04% 2,4'-isomer. The yield of 4,4'-dichlorodiphenyl sulfone was 78.3% relative to monochlorobenzene.

[0198]570 g of crude...

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Abstract

The present invention provides an economic and environmentally friendly method for the preparation of polymer grade 4,4'-dichlorodiphenyl sulfone which is substantially free of 2,4' and 3,4'-isomers of dichlorodiphenyl sulfone with yield of over 90%, with substantially reduced reaction times without the use of impregnated catalysts. Further no toxic byproducts such as dimethyl pyrosulfate are formed thereby reducing the load on effluent treatment with the added advantage of substantially recycling the reactants and byproducts. Further the present invention discloses a process is disclosed in which isomeric mixture of 4,4'-, 3,4'-, and 2,4'-dichlorodiphenyl sulfone produced during the preparation of 4,4'-dichlorodiphenyl sulfone is converted to value added products such as diphenyl sulfone, 2,4'-dihydroxydiphenyl sulfone, 4,4'-dihydroxydiphenyl sulfone and 2-aminodiphenyl sulfone.

Description

technical field [0001] The present invention relates to an economical and environmentally friendly process for producing substantially pure polymer grade material 4,4'-dichlorodiphenyl sulfone (4,4'-dichlorodiphenyl sulfone) in high yield. Background technique [0002] As a starting material for polysulfone and polyethersulfone, 4,4'-dichlorodiphenylsulfone (DCDPS) is important. Polysulfone and polyethersulfone belong to the family of thermoplastics known as engineering plastics and are used in high temperature applications. Polysulfone is used in medical equipment (nebulizers and dialysis components), electrical appliances (coffee pots, humidifiers and microwave ovens), automotive parts (steering wheel lock switches, relay insulators and pistons), and electronic equipment (TV components and capacitor films) manufacture. DCDPS has also been shown to be as potent as dichlorodiphenyltrichloroethane (DDT) against the housefly (Musca nebulo). DCDPS has also been used as a pes...

Claims

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Application Information

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IPC IPC(8): C07C315/00C07C317/06C07C317/14
CPCC07C317/06C07C315/00C07C317/14C07C315/06B01J31/12
Inventor H·R·班多德卡尔D·C·塞万特
Owner H R 班多德卡尔
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