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Preparation method of 4,4'-dicarboxy diphenyl ketone

A technology of dimethyl benzophenone and benzophenone, which is applied in the field of preparation of 4,4'-dicarboxybenzophenone, can solve the problems of unmentioned synthesis conditions and operation process, and achieves mild conditions , Overcome the effect of low yield

Inactive Publication Date: 2015-04-01
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] Yuxiang Dong, Jacques Chollet, etc. mentioned that 4,4'-dicarboxybenzophenone can be obtained by oxidizing 4,4'-dimethylbenzophenone with potassium permanganate, but did not mention the specific synthesis conditions and operation process

Method used

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  • Preparation method of 4,4'-dicarboxy diphenyl ketone
  • Preparation method of 4,4'-dicarboxy diphenyl ketone
  • Preparation method of 4,4'-dicarboxy diphenyl ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Add 3g (0.014267mol) 4,4'-dimethylbenzophenone, 0.56g (0.00214mol) 18-crown -6, 48ml water, 8.58g (0.07133mol) anhydrous MgSO 4 , the water bath was gradually warmed up to 50°C, and 22.54g (0.14267mol) KMnO was added in batches 4 , KMnO 4 A part was added dropwise in the form of 50ml aqueous solution, and the remaining KMnO 4 Add in portions as a solid. When there is no purple in the system, the reaction ends. Use alkali to adjust the pH of the system to 9-10, filter while it is hot, wash the filter cake twice, filter and combine the filtrate, acidify at 60°C to pH 2-3, at this time, a large amount of white solids are precipitated in the filtrate. Filter, transfer the filter cake to a beaker, add ethanol to wash twice at 65°C, filter, and dry to obtain a white powder product 4,4'-dicarboxybenzophenone (2.56g, yield 66.54%, purity 75.02%).

Embodiment 2

[0038] Add 3g (0.014267mol) 4,4'-dimethyl benzophenone, 0.12g (0.000285mol) trioctyl Methylammonium chloride, 100ml water, 4.29g (0.03566mol) anhydrous MgSO 4 , the water bath was gradually warmed up to 95°C, and 11.27g (0.07133mol) KMnO was added in batches 4 , KMnO 4 A part was added dropwise in the form of 375ml aqueous solution, and the remaining KMnO 4Add in portions as a solid. When there is no purple in the system, the reaction ends. Use alkali to adjust the pH of the system to 9-10, filter while it is hot, wash the filter cake twice, filter and combine the filtrate, acidify at 60°C to pH 2-3, at this time, a large amount of white solids are precipitated in the filtrate. Filter, transfer the filter cake to a beaker, add ethanol to wash twice at 65°C, filter, and dry to obtain a white powder product 4,4'-dicarboxybenzophenone (3.43g, yield 89.11%, purity 98.07%).

Embodiment 3

[0040] Add 3g (0.014267mol) 4,4'-dimethylbenzophenone, 0.47g (0.001426mol) hexadecane Trimethylammonium chloride, 44ml water, 4.29g (0.03566mol) anhydrous MgSO 4 , the water bath was gradually warmed up to 70°C, and 11.27g (0.07133mol) KMnO was added in batches 4 , KMnO 4 A part is added dropwise in the form of 200ml aqueous solution, and the remaining KMnO 4 Add in portions as a solid. When there is no purple in the system, the reaction ends. Use alkali to adjust the pH of the system to 9-10, filter while it is hot, wash the filter cake twice, filter and combine the filtrate, acidify at 60°C to pH 2-3, at this time, a large amount of white solids are precipitated in the filtrate. Filter, transfer the filter cake to a beaker, add ethanol to wash twice at 65°C, filter, and dry to obtain the white powder product 4,4'-dicarboxybenzophenone (3.17g, yield 82.25%, purity 91.67%).

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Abstract

The invention discloses a preparation method of 4,4'-dicarboxy diphenyl ketone. The preparation method is characterized by comprising the following steps of: adding 4,4'-dimethyl diphenyl ketone, potassium permanganate, anhydrous magnesium sulfate, a phase transfer catalyst and water into a four-necked flask which is provided with a stirrer, a thermometer and a balance feeder, wherein the molar ratio of 4,4'-dimethyl diphenyl ketone to potassium permanganate to anhydrous magnesium sulfate is 1:(4-10):(2-5), the molar ratio of 4,4'-dimethyl diphenyl ketone to the phase transfer catalyst is 1:(0.01-0.15), and the molar ratio of 4,4'-dimethyl diphenyl ketone to water is 1:(380-2200); reacting at the temperature of 50-100 DEG C under the condition that the pH value of the solution is 7 until the reaction system is not purplish red; adjusting the pH value of the reaction system to 8-10 with an alkali; filtering when the reaction system is still hot, and washing a filter cake with deionized water for two times; mixing filtrates, acidifying with an acid at the temperature of 50-70 DEG C, and adjusting the pH value to 2-3, and filtering to obtain a crude product; washing the crude product with ethanol for two times at the temperature of 50-70 DEG C, filtering, and drying to obtain the pure 4,4'-dicarboxy diphenyl ketone.

Description

technical field [0001] The invention relates to a preparation method of 4,4'-dicarboxybenzophenone, which belongs to the technical field of organic synthesis. Background technique [0002] 4,4'-Dicarboxybenzophenone is an important intermediate in organic synthesis, widely used in organic coatings, dyes, plastics, medicine, daily chemicals, spices, food, pesticides and other fields. Its molecular formula is: [0003] [0004] In addition, the benzophenone structure and dicarboxyl structure contained in 4,4'-dicarboxybenzophenone can not only be used as a hydrogen abstraction type free radical initiator, but also can be used as a substitute for making photosensitive coatings and photosensitive resin plates. Material synthesis For example, in the process of plastic synthesis, a part of the monomer is added as the third monomer to modify the material. [0005] There are not many reports abroad about the synthesis of 4,4'-dicarboxybenzophenone, and there is no report in Chi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/16C07C65/34
CPCC07C51/16C07C65/34
Inventor 蒋文伟张彦杰
Owner SICHUAN UNIV
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