Bifunctional catalyst and application of bifunctional catalyst in preparation of benzil by benzoin dehydrogenation/oxidation

A dual-function catalyst and catalyst technology, which is applied in the direction of oxidative preparation of carbonyl compounds, carbon-based compound preparation, and organic compound preparation, can solve the problems of expensive reaction solvents, large emissions of environmental pollutants, and difficult separation and purification. Recyclable process, high conversion rate of raw materials, and the effect of reducing environmental pollution

Active Publication Date: 2012-05-30
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Domestic benzil industrial production methods usually use nitric acid as an oxidizing agent for metered oxidation, but the reaction is intense, and a large amount of nitrogen oxide gas is released to pollute the environment. It is harmful to human health, and a large amount of waste acid is produced after the reaction. Recycling will increase costs, and emissions will pollute the environment. ; For this situation, people have carried out extensive research in the past two decades, and the research methods reported mainly include DMSO/(COCl) 2 /CH 2 Cl 2 , (PhCH 2 Et 3 N)Br - /(PhCO) 2 o 2 /MeCN, NBS/CCl 4 Oxidation method, H 2 o 2 Oxidation method, a dir

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] by Co 2+ It is immobilized on a macroporous styrene-based anion exchange resin through chemical bonds and used as a catalyst for the dehydrogenation-oxidation of benzoin to generate benzil.

[0025] Take by weighing 20 grams of macroporous strong basic quaternary ammonium anion-exchange resin (D261 type) that Tianjin Nankai University Resin Co., Ltd. produces, soak with the NaOH aqueous solution of 0.5mol / L first after 30 minutes, then wash with deionized water, finish pretreatment Treatment process: put the processed resin into a three-necked flask with a reflux condenser and a stirrer, add 80mL of dimethylformamide (DMF), and 5 grams of p-aldehyde benzoic acid, start the stirrer to stir, and heat to reflux 5h, cooled to room temperature, the resin was filtered off and washed with DMF. Add the reacted resin, 80 mL of xylene and 5 g of cobalt acetylacetonate into a three-necked flask. After heating to reflux for 3 hours, the resin was filtered out, fully soaked and wa...

Embodiment 2

[0028] by Cu 2+ It is immobilized on the super-strong gel type strong acid cationic resin through chemical bonds and used as a catalyst for the dehydrogenation-oxidation of benzoin to generate benzil.

[0029] Take by weighing 20 grams of super-strong gel type strong acid cationic resin (D-61 type) produced by Tianjin Nankai University Resin Co., Ltd., first use 0.5mol / L of HCl aqueous solution to soak for 30 minutes, and then wash with deionized water to complete the pre-treatment. Processing process: put the processed resin into a three-necked flask with a reflux condenser and a stirrer, add 80mL of deionized water, and 8 grams of copper acetate, start the stirrer to stir, heat and reflux for 5h, cool to room temperature, and filter out After the resin is filtered out, it is fully soaked and washed with deionized water and absolute ethanol respectively, and dried at 80°C. The copper content of the resin was determined to be 7.5%.

[0030] Above-mentioned resin is packed in...

Embodiment 3

[0032] The vanadyl anion is immobilized on the macroporous styrenic anion exchange resin through a chemical bond and used as a catalyst for the dehydrogenation-oxidation of benzoin to generate benzil.

[0033] Take by weighing 20 grams of macroporous strong basic quaternary ammonium anion-exchange resin (D261 type) that Tianjin Nankai University Resin Co., Ltd. produces, soak with the NaOH aqueous solution of 0.5mol / L first after 30 minutes, then wash with deionized water, finish pretreatment Treatment process: put the treated resin into a three-necked flask with a reflux condenser and a stirrer, add 70mL of deionized water, 10mL of ammonia water, and 5 grams of ammonium metavanadate, start the stirrer to stir, heat and reflux for 5h, and cool to At room temperature, after filtering out the resin, fully soak and wash with dimethylformamide (DMF) and absolute ethanol respectively, and dry at 80°C. The vanadium content of the resin was determined to be 3.4%.

[0034] Above-ment...

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PUM

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Abstract

The present invention relates to a bifunctional catalyst and an application of the bifunctional catalyst in preparation of benzil by benzoin dehydrogenation/oxidation. According to the catalyst, an anion exchange resin or a cation exchange resin is adopted as a carrier; a variable-valence transition metal or a rare earth metal element is bonded on the carrier in a chemical bonding manner, whereinthe binding amount of the variable-valence transition metal or the rare earth metal element is 0.5-10% of the weight of the catalyst; the metal element on the carrier is bonded with an acidic ion exchange resin or an alkaline ion exchange resin through chemical bonds, wherein the metal element on the carrier is adopted as an oxidation catalyst; under a certain reaction condition, benzoin is subjected to a dehydrogenation/oxidation process, hydroxyl is transformed into carbonyl, and the measured water is generated. The catalyst has the following advantages that: the use conditions are mild, the product is easy to separate, the catalyst can be used many times, and the like.

Description

technical field [0001] The present invention develops a catalyst for the preparation of benzil by dehydrogenation / oxidation of benzoin. The catalyst is composed of transition metal elements supported by resin. Under certain reaction conditions, the hydroxyl group on the benzoin is converted into a carbonyl group. Simultaneously generate the process of metered water. The catalyst has the characteristics of mild use conditions, easy separation of products, and repeated use. Background technique [0002] Benzil, also known as diphenyl ethylene dione, also known as dibenzoyl, bibenzoyl, is an important organic chemical raw material. It is used in the synthesis of photosensitizers, curing agents, insecticides, pharmaceuticals and various functional materials, and is also suitable for the production of printing inks for food, etc., and has broad application prospects. Domestic benzil industrial production methods usually use nitric acid as an oxidizing agent for metered oxidatio...

Claims

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Application Information

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IPC IPC(8): B01J31/28B01J31/36B01J31/32B01J31/26B01J31/34C07C49/784C07C45/29C07C45/39
Inventor 高进徐杰杜中田张展马红
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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