Preparation method for catalytic synthesis of 4,4'-dichlorophenylsulfone

A dichlorophenyl sulfone and chemical synthesis technology, applied in the field of compound preparation, can solve the problems of complex process, low product melting point, low conversion rate, etc., and achieve the effects of high product purity, good economic benefits, and low solubility

Inactive Publication Date: 2020-06-19
九江中星医药化工有限公司
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  • Application Information

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Problems solved by technology

The sulfuric acid method has low cost and simple raw materials, but the conversion rate is low, the reaction time is long, the melting point of the product is low, and the quality is not good
The chlorosulfonic acid process is relatively mature, and the product quality is good, but the pro

Method used

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  • Preparation method for catalytic synthesis of 4,4'-dichlorophenylsulfone
  • Preparation method for catalytic synthesis of 4,4'-dichlorophenylsulfone
  • Preparation method for catalytic synthesis of 4,4'-dichlorophenylsulfone

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preparation example Construction

[0016] A preparation method for catalyzing and synthesizing 4,4'-dichlorophenyl sulfone, the preparation process of the superparamagnetic nanoparticle-loaded ionic liquid catalyst used in the present invention:

[0017] Weigh respectively 3-chloropropyltriethoxysilane 1 (12ml, 50mmol), imidazole 2 (3.4g, 50mmol) in a reaction vessel, add 50ml of dry toluene, N 2 Under protection, reflux and stir the reaction for 24h, and obtain intermediate 3 through column chromatography (developing agent is EA); take 1g Fe 3 o 4 / SiO 2 Put the solid particles in the reaction vessel, add 50ml of anhydrous toluene, and ultrasonicate for 1h. After the ultrasonication is over, take 0.5g of intermediate 3 and dissolve it in 20ml of anhydrous toluene, then add it dropwise to the reaction system, N 2 Reflux and stir the reaction for 48 hours under protection. After the reaction, collect it with a magnet and wash it three times with ethanol, and dry it in a vacuum to obtain the solid particle 4; t...

Embodiment 1

[0024] In the four-necked flask, add chlorobenzene (1.0mol, 112.5g) first, then add the catalyst (0.34g, 0.2mmol), stir well and add thionyl chloride (0.2mol, 23.8g) dropwise, the reaction exothermic, control The temperature is 30°C. After adding the thionyl chloride dropwise, keep stirring for 1 h. After the reaction is over, add the catalyst recovered by the magnetic field, pour out the reaction solution, add a saturated sodium bicarbonate solution dropwise to the reaction solution to adjust the pH value to neutral, and stir for 0.5 h. Filtrate while it is hot, cool the filtrate to 0-5°C for crystallization, filter and dry to obtain solid 4,4'-dichlorodiphenylsulfoxide (0.19mol, 51.2g), heat and dissolve with glacial acetic acid (0.3mol, 18g), 60 Add 35% hydrogen peroxide (0.3mol, 30g) dropwise at ℃ for oxidation, keep warm for 2h, cool down, filter and dry to obtain 4,4'-dichlorodiphenylsulfone (0.18mol, 51.8g), the content is 99.5% (HPLC detection), The yield was 90.5%. ...

Embodiment 2

[0026] First add chlorobenzene (1.2mol, 135g) in the four-necked flask, then add the catalyst (0.34g, 0.2mmol), stir well and add thionyl chloride (0.2mol, 23.8g) dropwise, the reaction exothermic, control the temperature 30°C. After adding the thionyl chloride dropwise, keep stirring for 1 h. After the reaction is over, add the catalyst recovered by the magnetic field, pour out the reaction solution, add a saturated sodium bicarbonate solution dropwise to the reaction solution to adjust the pH value to neutral, and stir for 0.5 h. Filtrate while it is hot, cool the filtrate to 0-5°C to crystallize, filter and dry to obtain solid 4,4'-dichlorodiphenylsulfoxide (0.185mol, 50.0g), heat and dissolve with glacial acetic acid (0.3mol, 18g), 60 Add 35% hydrogen peroxide (0.3mol, 30g) dropwise at ℃ for oxidation, keep warm for 2h, cool down, filter and dry to obtain 4,4'-dichlorodiphenylsulfone (0.17mol, 50.0g), the content is 99.6% (HPLC detection), The yield was 87.5%.

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Abstract

The invention discloses a preparation method for catalytic synthesis of 4,4'-diaminostilbene. The preparation method comprises the following steps: with a superparamagnetic nanoparticle loaded ionic liquid as a catalyst, subjecting chlorobenzene and thionyl chloride to a Friedel-Crafts reaction under the action of the catalyst, after the reaction is completed, additionally adding a catalyst recovered by a magnetic field, pouring out a reaction solution, dropwise adding a saturated sodium bicarbonate solution into the reaction solution until the pH value of the solution is adjusted to be neutral, then carrying out stirring, filtering the material liquid while the material liquid is hot, cooling a filtrate to 0-5 DEG C for crystallizing, carrying out filtering so as to obtain 4,4'-dichlorodiphenyl sulfoxide, dissolving the 4,4'-dichlorodiphenyl sulfoxide into glacial acetic acid, adding hydrogen peroxide for an oxidation reaction, carrying out cooling after the reaction is finished, andcarrying out filtering so as to obtain 4,4'-dichlorodiphenyl sulfone. According to the invention, the chlorobenzene is used as a reaction raw material and a solvent; no solvent impurities are not mixed; meanwhile, simple process, low cost and few impurities are achieved; an obtained product is high in purity and has a content of 99.2% or above; the content of a 2,4'-isomer is smaller than 0.1%; the yield reaches 90% or above; and the preparation method provided by the invention is good in economic benefit and applicable to industrial production.

Description

technical field [0001] The invention relates to a compound preparation method, in particular to a green, high-efficiency method for preparing 4,4'-dichlorodiphenyl sulfone by using an ionic liquid loaded with superparamagnetic nanoparticles as a catalyst. Background technique [0002] 4,4’-Dichlorodiphenylsulfone (DDS) is an important organic synthesis product, the main raw material for the preparation of engineering plastics such as polysulfone and polyethersulfone, and an intermediate for medicines, dyes and pesticides. It can be used to prepare a variety of polymer products, such as resins such as bisphenol A polysulfone, polyphenylene ether sulfone, and polyamide sulfone, and can also be used to prepare 4,4'-diaminodiphenylsulfone, an intermediate of leprosy medicine. With the wide application of polymer materials, the demand for DDS is also increasing. [0003] There are many ways to produce DDS in industry, mainly including sulfuric acid method, chlorosulfonic acid me...

Claims

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Application Information

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IPC IPC(8): C07C315/04C07C315/02C07C317/14B01J31/22B01J31/02
CPCB01J31/0284B01J31/0295B01J31/2217B01J35/0013B01J35/0033B01J2231/4205B01J2531/0252B01J2531/824C07C315/02C07C315/04C07C317/14
Inventor 周以鸿赖立冬何文秀胡华南程龙进骆建轻邵辉锋
Owner 九江中星医药化工有限公司
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