Reaction method for selectively synthesizing aromatic aldehyde or aromatic carboxylic acid

A technology for aromatic carboxylic acids and aromatic aldehydes, which is applied in the preparation of carboxylate salts, chemical instruments and methods, and the preparation of organic compounds. It can solve problems such as lack of atom economy, complicated catalyst preparation, and narrow substrate range. Good conversion rate, achieve repeated use, low price effect

Active Publication Date: 2020-11-20
NANJING UNIV OF TECH
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Problems solved by technology

[0005] In order to overcome the shortcomings of the traditional synthesis technology of aromatic aldehydes or aromatic carboxylic acids that do not have atom economy, many wastes, and high cost, and the existing photocatalytic oxidation technology has low selectivity, narrow substrate range, cumbersome or expensive catalyst preparation Shortcomings, the present invention provides a method for using ferric sulfate as a catalyst to synthesize aromatic aldehydes and aromatic carboxylic acids with high selectivity of air oxidation under ultraviolet light irradiation

Method used

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  • Reaction method for selectively synthesizing aromatic aldehyde or aromatic carboxylic acid

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Embodiment 1

[0021] Embodiment 1: the photocatalytic synthesis of p-chlorobenzaldehyde

[0022] In a 25mL colorless transparent glass test tube, add 0.5mmol p-chlorotoluene, 5mL acetonitrile, 1mmol ferric sulfate, and 5mL water. Air is introduced through the mouth of the test tube. Under the conditions of air cooling and vigorous stirring, the reaction solution was irradiated with a 50W ultraviolet light source with a wavelength of 350-370nm for 10h. Stop the reaction, extract with ethyl acetate (10mL × 3), combine the organic layers, dry with sodium sulfate, and remove the organic solvent by rotary evaporation to obtain a crude product, which is analyzed by normalized area method gas chromatography-mass spectrometry. For: p-chlorobenzyl alcohol 3%, p-chlorobenzaldehyde 90%, p-chlorobenzoic acid 2.5%, p-chlorotoluene 4%.

Embodiment 2

[0023] Embodiment 2: the photocatalytic synthesis of p-chlorobenzoic acid

[0024] In a 25mL colorless transparent glass test tube, add 0.5mmol p-chlorotoluene, 5mL acetonitrile, 0.25mmol ferric sulfate, and 5mL water. Air is introduced through the mouth of the test tube. Under the condition of vigorous stirring, the air was introduced, and the reaction solution was irradiated with a 50W ultraviolet light source with a wavelength of 350 to 370nm, and reacted for 16 hours to obtain a milky white yellowish solid-liquid mixture. The reaction solution was cooled down, extracted with ethyl acetate (10mL×3), the organic layers were combined, dried over sodium sulfate, the organic solvent was removed by rotary evaporation, and purified by column chromatography to obtain 0.071g of p-chlorobenzoic acid, melting point 240°C, yield 81 %.

Embodiment 3

[0025] Embodiment 3: the synthesis of benzaldehyde

[0026]In a 25mL colorless transparent glass test tube, add 0.5mmol toluene, 1mmol ferric sulfate, 5mL water, 5mL acetonitrile, and introduce air through the test tube mouth. The whole reaction system is sealed to prevent low yield due to volatilization of toluene. Under the condition of vigorous stirring, the reaction solution was irradiated with a 50W ultraviolet light source with a wavelength of 350-370nm for 12h. After the reaction, the reaction solution was extracted with dichloromethane (10mL×3), the organic layers were combined, dried over anhydrous sodium sulfate, and then the solvent was removed by rotary evaporation, and separated by column chromatography to obtain 0.041g of benzaldehyde with a yield of 77%.

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Abstract

The invention provides a reaction method for selectively synthesizing aromatic aldehyde or aromatic carboxylic acid. Toluene aromatic hydrocarbon without substituent or with substituent on a benzene ring is used as a raw material, an inorganic salt of ferric iron is used as a catalyst, air or oxygen is used as an oxidizing agent, a mixed solution of acetonitrile and water is used as a solvent, theraw material is oxidized by adjusting the dosage of the catalyst to obtain aromatic aldehyde or aromatic carboxylic acid, and the aromatic aldehyde or aromatic carboxylic acid is irradiated by ultraviolet light for 10-16 hours. Aromatic carboxylic acid obtained under the condition that the dosage of the catalyst is 5-50% mol of aromatic hydrocarbon is used as a main product, wherein the use amount of the catalyst is 70-200% mol of aromatic hydrocarbon. The reaction method provided by the invention has the characteristics of atom economy and high selectivity, uses the metal iron salt with richearth content for catalysis, and has the advantages of mild conditions, recyclable catalyst and solvent and the like.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a reaction method for selectively synthesizing aromatic aldehydes or aromatic carboxylic acids. Background technique [0002] Aromatic aldehydes and aromatic carboxylic acids are widely used organic intermediates. Among the traditional synthesis methods of aromatic formaldehyde, the methods with more application value mainly include: hydrolysis of dichlorobenzyl, chemical oxidant oxidation of phenyl ring methyl group, etc. In addition, the general pathways for the synthesis of aromatic carboxylic acids mainly include the hydrolysis of trichlorobenzyl and the complete oxidation of phenylcyclomethyl groups. These traditional methods for the synthesis of aromatic aldehydes and aromatic carboxylic acids are not atom-economical, require a large amount of material consumption and generate a lot of inherent waste, and are likely to have adverse effects on the environment. In recent y...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/55C07C45/36C07C63/70C07C51/265C07C47/54C07C63/06C07C47/542C07C63/04
CPCC07C45/36C07C51/265C07C47/55C07C63/70C07C47/54C07C63/06C07C47/542C07C63/04Y02P20/584
Inventor 李玉峰马鸿飞顾洁凡卜洪忠吴杰庆王晨万雨婷
Owner NANJING UNIV OF TECH
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