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Method for preparing 2-alkyl anthraquinone by taking solid super acids as catalysts

A technology of solid superacid and alkyl anthraquinone, which is applied in the direction of carboxylate preparation, carboxylic anhydride preparation, chemical instruments and methods, etc., can solve the problem of low conversion rate of 2-(benzoyl)benzoic acid and anthraquinone selectivity No high-level problems, to achieve the effect of reducing equipment maintenance and repair costs, high catalytic efficiency, and less usage

Inactive Publication Date: 2018-07-20
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the disadvantage is that the conversion rate of 2-(benzoyl)benzoic acid is low, and the selectivity of anthraquinone is not high

Method used

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  • Method for preparing 2-alkyl anthraquinone by taking solid super acids as catalysts
  • Method for preparing 2-alkyl anthraquinone by taking solid super acids as catalysts

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 5.0g of 2-(4'-ethylbenzoyl)benzoic acid into the reactor, liquefy at 130°C, add 1.0g of perfluorosulfonic acid resin, stir and heat up to 200°C, react for 1.0 hour, cool, add Chloroform completely dissolves the reaction product, filters and separates the catalyst and the reaction solution, washes the catalyst with chloroform, and recycles after drying; the reaction solution is washed with 0.1M sodium hydroxide solution, then washed with water until neutral, dried, and distilled off under reduced pressure. solvent to obtain 2-ethylanthraquinone. The composition of the solid product is analyzed by high performance liquid chromatography and the conversion rate of raw materials and catalyst selectivity are calculated. As a result, the conversion rate of 2-(4'-ethylbenzoyl) benzoic acid is 95.1%. The selection of 2-ethylanthraquinone Sex is 76.6%.

Embodiment 2

[0033] Add 5.0g of 2-(4'-ethylbenzoyl)benzoic acid into the reactor with reflux device, add 75mL of chlorobenzene to dissolve 2-(4'-ethylbenzoyl)benzoic acid, add 1.0g Perfluorosulfonic acid resin, stirred and heated to 140°C, refluxed for 3.0 hours. After cooling, filter and separate to obtain the catalyst and the reaction liquid. The catalyst was washed with chloroform and dried in vacuum before reuse. The reaction solution was washed with 0.1M sodium hydroxide solution, and then washed with water until neutral, dried with a desiccant, and evaporated under reduced pressure to remove the solvent to obtain 2-ethylanthraquinone. The composition of the solid product was analyzed by high performance liquid chromatography and the conversion of raw material and catalyst selectivity were calculated. The conversion rate of 2-(4'-ethylbenzoyl)benzoic acid was 98.2%, and the selectivity of 2-ethylanthraquinone was 73.5%.

Embodiment 3

[0035] Add 5.0g of 2-(4'-ethylbenzoyl)benzoic acid into the reactor, liquefy at 130°C, add 2.0g of phosphotungstic acid, stir and raise the temperature to 180°C, and react for 1.0 hour. After cooling, add chloroform to dissolve the reaction product completely, filter and separate to obtain the catalyst and the reaction solution, the catalyst is washed with chloroform, and the catalyst is recovered after vacuum drying, the reaction solution is washed with 0.1M sodium hydroxide solution, then washed with water until neutral, and dried The solvent was dried, and the solvent was distilled off under reduced pressure to obtain 2-ethylanthraquinone. The composition of the solid product was analyzed by high performance liquid chromatography and the conversion of raw material and catalyst selectivity were calculated. The conversion rate of 2-(4'-ethylbenzoyl)benzoic acid was 85.5%, and the selectivity of 2-ethylanthraquinone was 58.4%.

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Abstract

The invention provides a method for preparing 2-alkyl anthraquinone by taking solid super acids as catalysts. The 2-alkyl anthraquinone (alkyl is straight or branched alkyl with the number of carbon atoms of 1-6) is obtained by adopting the solid super acids like perfluorinated sulfonic acid resin and heteropoly acid as the catalysts, taking 2-(4'-alkyl benzoyl) benzoic acid as a raw material andperforming acylated dewatering closed loop through Friedel-Crafts reaction. The method provided by the invention is characterized in that traditional smoking sulfuric acid catalysts are replaced by the solid super acids, so that the environment is friendly, and no waste acid is discharged; the operation process is simple, and the solid catalysts are easy to recover; therefore, the method is a green pollution-free new process.

Description

technical field [0001] The invention belongs to the technical field of synthesis of fine chemical products, and in particular relates to a preparation method of 2-alkylanthraquinone. Background technique [0002] 2-Alkylanthraquinone is a series of important organic intermediates, among which 2-ethylanthraquinone is the main species in this series of products, and is used as the main raw material for the preparation of hydrogen peroxide working solution by anthraquinone method, and its demand increases with the production of hydrogen peroxide The expansion of installations is increasing year by year. Other 2-alkylanthraquinones with different substituents (alkyl groups include straight chain or branched chain alkyl groups with a carbon number of 1 to 6) are widely used as important organic intermediates or raw materials for the preparation of optical sieve resins and photosensitive polymerizers. and dye intermediates, etc. [0003] The traditional production process of 2-a...

Claims

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Application Information

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IPC IPC(8): C07C46/00C07C50/16
CPCC07C46/00C07C51/083C07C51/373C07C50/16C07C65/34
Inventor 冯拥军谢浩杰李殿卿李宏宇唐平贵
Owner BEIJING UNIV OF CHEM TECH
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