Process for preparing high-pure 4-hydroxybenzophenone

A hydroxybenzophenone, high-purity technology, applied in the direction of condensation to prepare carbonyl compounds, organic chemistry, etc., can solve the problems of low recovery rate, insufficient product yield and purity, high cost, etc., to achieve increased purity and yield , Conducive to recycling and application, and the effect of reducing usage

Inactive Publication Date: 2010-04-14
JIANGSU POLYTECHNIC UNIVERSITY +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Chinese patent CN101298414 and document Synthetic Communications, 30 (9), 1605-1608; 2000, disclose a kind of with phenol and trichlorotoluene as raw material, with aluminum chloride as catalyst, in specific solvent (mainly still dichloromethane , dichloroethane, chloroform and other chlorinated aliphatic hydrocarbons), by Friedel-Crafts reaction, the method for making 4-hy

Method used

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  • Process for preparing high-pure 4-hydroxybenzophenone
  • Process for preparing high-pure 4-hydroxybenzophenone

Examples

Experimental program
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Effect test

Embodiment 1

[0022] In the 1000L reactor, add chlorobenzene 200KG and aluminum trichloride 426KG (3190mol). Start stirring, and add dropwise a mixed solution of 200KG (2127mol) of phenol and 100KG of chlorobenzene at 20°C to 25°C. After the addition is complete, stir for 30 minutes, and add 314KG (2235mol) of benzoyl chloride dropwise. Slowly raise the temperature, react at 40°C-45°C for 2 hours, and react at 60°C-70°C for 1 hour.

[0023] Slowly add the above reaction liquid into 1800KG cold water, and stir at 20°C to 30°C for 2 hours. Centrifuge, wash the solid with water until neutral, and dry to obtain crude 4-hydroxybenzophenone. Then recrystallized with 2 times the amount of crude toluene to obtain 376.8 kg of white 4-hydroxybenzophenone with a yield of 89.5% and a purity of 99.5% (HPLC value). The liquid is separated into the water layer, the oil layer is washed with water until neutral, dried with anhydrous calcium chloride and then distilled to recover chlorobenzene for recycli...

Embodiment 2

[0025] In the 1000L reactor, add chlorobenzene 200KG and aluminum trichloride 426KG (3190mol). Start stirring, and add dropwise a mixed solution of 200KG (2127mol) of phenol and 100KG of chlorobenzene at 20°C to 25°C. After the addition is complete, stir for 30 minutes, and add 448KG (3190mol) of benzoyl chloride dropwise. Slowly raise the temperature, react at 40°C-45°C for 2 hours, and react at 60°C-70°C for 1 hour.

[0026] Slowly add the above reaction liquid into 1800KG cold water, and stir at 20°C to 30°C for 2 hours. Centrifuge, wash the solid with water until neutral, and dry to obtain crude 4-hydroxybenzophenone. Then recrystallize with 2 times the amount of crude toluene to obtain 347.1 KG of white 4-hydroxybenzophenone with a yield of 82.5% and a purity of 98.5% (HPLC value). The liquid is separated into the water layer, the oil layer is washed with water until neutral, dried with anhydrous calcium chloride and then distilled to recover chlorobenzene for recyclin...

Embodiment 3

[0028] In the 1000L reactor, add chlorobenzene 200KG and aluminum trichloride 312KG (2337mol). Start stirring, and add dropwise a mixed solution of 200KG (2127mol) of phenol and 100KG of chlorobenzene at 20°C to 25°C. After the addition is complete, stir for 30 minutes, and add 314KG (2235mol) of benzoyl chloride dropwise. Slowly raise the temperature, react at 40°C-45°C for 2 hours, and react at 60°C-70°C for 1 hour.

[0029] Slowly add the above reaction liquid into 1800KG cold water, and stir at 20°C to 30°C for 2 hours. Centrifuge, wash the solid with water until neutral, and dry to obtain crude 4-hydroxybenzophenone. Recrystallize with twice the amount of crude toluene to obtain 330.8KG of white 4-hydroxybenzophenone, with a yield of 78.6% and a purity of 98.2% (HPLC value). The liquid is separated into the water layer, the oil layer is washed with water until neutral, dried with anhydrous calcium chloride and then distilled to recover chlorobenzene for recycling.

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Abstract

The invention relates to a process for preparing high-pure 4-hydroxybenzophenone, which belongs to the field of organic chemical synthesis. The process includes steps of adding and stirring chlorobenzene and aluminium choride in a reactor, dripping mixing fluid of phenol and chlorobenzene when at a temperature of 10DEG C-50 DEG C, stirring for 30 min again after dripping, dripping benzoyl, raising temperature slowly, reacting for 2h when at a temperature of 40DEG C-45DEG C, reacting for 1h when at a temperature of 60DEG C-70DEG C, slowing adding reaction fluid into cold water, stirring for 2hwhen at the temperature of 20-30DEG C, centrifuging, washing solid via water until being neutral, drying to obtain crude 4-hydroxybenzophenone, utilizing toluene with quantity double of that of the crude 4-hydroxybenzophenone to recrystallize to obtain white 4-hydroxybenzophenone, washing an oil layer via water until being neutral, distilling anhydrous calcium chloride after drying and then recycling chlorobenzene. Mole ratio of phenol and benzoyl chloride is 1: (1-1.5), mole ratio of phenol and aluminium choride is 1: (1-2), and mass ratio of phenol and chlorobenzene is 1: (1-5). The processutilizes the chlorobenzene as a reaction solvent, greatly increases purity and yield of products, and greatly reduces usage of the solvent.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis and relates to a preparation method of high-purity fine chemical product 4-hydroxybenzophenone. Background technique [0002] 4-Hydroxybenzophenone is an important fine chemical raw material, which is widely used in the fields of medicine and materials (especially photocurable materials). The preparation method of 4-hydroxybenzophenone mainly contains two kinds at present: [0003] A kind of is traditional synthetic route, promptly starts out with phenol and benzoyl chloride as raw material, is catalyst with aluminum trichloride, in specific solvent (mainly dichloromethane, chloroform, carbon tetrachloride, ethylene dichloride etc. Chlorinated aliphatic hydrocarbons), through two-step reaction of esterification and rearrangement, 4-hydroxybenzophenone product is obtained. This synthetic route is a synthetic method commonly used by manufacturers of 4-hydroxybenzophenone at present, but t...

Claims

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Application Information

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IPC IPC(8): C07C49/83C07C45/46
Inventor 张娜高学民宋国强姜飞曹引梅
Owner JIANGSU POLYTECHNIC UNIVERSITY
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