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Preparation method for synthesizing carboxylic acid by oxidizing aldehyde through using bimetallic catalyst

A bimetallic catalyst and aldehyde oxidation technology, which is applied in the preparation of organic compounds, carboxylate preparation, chemical instruments and methods, etc., can solve the problems of harsh reaction conditions, narrow substrate applicability, difficult coordination, etc., and achieve high yield , mild reaction conditions, simple operation

Active Publication Date: 2020-05-08
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still some problems in the existing catalytic system, mainly reflected in: relatively harsh reaction conditions, narrow substrate applicability (J.Org.Chem.2013,9,602; RSC.Adv.2013,3,6334)
The reason for these problems is speculated that it is difficult for a single metal catalyst to coordinate the simultaneous completion of aldehyde oxidation and oxidant activation, especially the activation of oxygen, so harsh conditions are usually required, or the effects on different substrates are not the same

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Under normal pressure oxygen condition, water (2mL), benzaldehyde (1mmol), Cu(OAc) 2 ·H 2 O (0.003mmol, 0.3% mole fraction), Co(OAc) 2 4H 2 O (0.003mmol, 0.3% mole fraction) and a magnetic stirrer were added to a 15mL glass reaction tube, and an oxygen bulb was connected. The reaction tube was placed in an oil bath preheated to 70° C. and stirred for 9 h. After the reaction was completed, the temperature was lowered, and the solid solid of the crude product was separated by centrifugation, then ultrasonically washed with 3 mL of water, centrifuged, and dried (to constant weight) to obtain the target product, and the separation yield was 97%. The product is a white solid with a melting point of 122°C. The NMR data of the product are as follows: 1 H NMR (500MHz, CDCl 3 ) δ 11.47 (s, 1H), 8.15 (d, J=7.8 2H), 7.63 (t, J=7.6Hz 1H), 7.49 (t, J=8.0Hz, 2H). Embodiment 2 p-methoxybenzaldehyde is oxidized to prepare p-methoxybenzoic acid

Embodiment 2

Embodiment 3

[0017] Under atmospheric oxygen conditions, 1,4-dioxane (2mL), p-methoxybenzaldehyde (1mmol), Cu(OAc) 2 ·H 2 O (0.02mmol, 2% mole fraction) and Co(OAc) 2 4H 2 O (0.02mmol, 2% mole fraction) was added into a 15mL glass reaction tube, and an oxygen bulb was connected. The reaction tube was placed in an oil bath pre-heated to 70°C and stirred for 12 hours. After the reaction was completed, the temperature was lowered, and the solid product was centrifuged to separate the crude product solid, then ultrasonically washed with 3 mL of water, centrifuged, and dried to constant weight to obtain the target product. %. The product is an off-white solid with a melting point of 184°C. The NMR data of the product are as follows: 1 H NMR (500MHz, DMSO) δ 12.62 (s, 1H), 7.89 (d, J = 8.5Hz 2H), 7.01 (d, J = 8.5Hz 2H), 3.82 (s, 3H). Example 3 Oxidation of m-methoxybenzaldehyde to prepare m-methoxybenzoic acid Under normal pressure oxygen conditions, 1,4-dioxane (2mL), m-methoxybenzaldehyde...

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Abstract

The invention discloses a preparation method for synthesizing carboxylic acid by oxidizing aldehyde through using a bimetallic catalyst. The method comprises the following steps: an aldehyde compoundtaken as a substrate is reacted for 1-12 h in a reaction solvent under a normal-pressure oxygen condition at the temperature of 10-90 DEG C under the action of the bimetallic catalyst under a stirringcondition, the reaction system is cooled to room temperature after the reaction conversion is completed, and the obtained reaction solution is centrifuged, filtered and dried to constant weight to obtain the carboxylic acid compound, wherein the aldehyde compound is aromatic aldehyde, fatty aldehyde or alicyclic aldehyde. The method has the advantages of mild reaction conditions and simplicity inoperation; and Cu(OAc)2. H2O and Co(OAc)2. 4H2O in a molar ratio of 1:1 are used as the bimetallic catalyst, high-yield carboxylic acid products can be obtained by adjusting the reaction temperature,the solvent and the catalyst dosage aiming at different types of raw material aldehydes, and the highest yield can reach 98%.

Description

technical field [0001] The invention relates to a preparation method for oxidizing aldehydes to synthesize carboxylic acids with a bimetallic catalyst, which belongs to the technical field of homogeneous catalysis. Background technique [0002] Carboxylic acid is a class of important fine chemicals and intermediates (Org.Geochem.1993,20,973; J.Org.Chem.2005,70,4272; Med. Chem. Lett. 2005, 15, 3430). There are many ways to prepare carboxylic acids, among which the oxidation of aldehydes is one of the most commonly used effective methods. Theoretically speaking, the transition metal-catalyzed aldehyde oxidation reaction has the advantages of easy operation, easy adjustment of catalyst performance, and the use of green and environmentally friendly oxidants such as oxygen and hydrogen peroxide, and has attracted more and more attention from academia and industry. However, there are still some problems in the existing catalytic system, mainly reflected in: relatively harsh reac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/235C07C63/06C07C65/21C07C63/04C07C63/36C07C57/30C07C63/70C07C53/126C07C53/128C07C61/08B01J31/04
CPCC07C51/235B01J31/04C07C2601/14B01J2231/70B01J35/19C07C63/06C07C65/21C07C63/04C07C63/36C07C57/30C07C63/70C07C53/126C07C53/128C07C61/08Y02P20/584
Inventor 胡信全王聪巫珂靳立群
Owner ZHEJIANG UNIV OF TECH
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