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A kind of triphenylamine-based cobalt porphyrin catalyst and its preparation method and application

A technology of triphenylamine-based cobalt porphyrins and catalysts, which is applied in the field of electrocatalytic oxygen reduction to produce hydrogen peroxide, can solve the problems of changing the proton concentration of the catalytic interface, increasing the explosion risk, and the influence of oxygen adsorption, and achieves good electrocatalysis. Oxygen reduction activity, improvement of hydrogen peroxide selectivity, effect of high hydrogen peroxide selectivity

Active Publication Date: 2022-06-21
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, industrial hydrogen peroxide is mainly produced by anthraquinone method. The disadvantages of this production method are 1) large infrastructure investment and high energy consumption, 2) excessive hydrogenation in the production process makes anthraquinone continuously degrade, 3 ) The coexistence of organic solvents and high-concentration hydrogen peroxide will increase the risk of explosion in production
The exocyclic substituents of cobalt porphyrin will affect the catalytic performance of ORR: 1) The electron donating and withdrawing effects of substituents will change the electron cloud density of the central metal, which will affect the adsorption of oxygen; 2) Substituents with proton management effects will change the proton concentration at the catalytic interface

Method used

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  • A kind of triphenylamine-based cobalt porphyrin catalyst and its preparation method and application
  • A kind of triphenylamine-based cobalt porphyrin catalyst and its preparation method and application
  • A kind of triphenylamine-based cobalt porphyrin catalyst and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] (1) Synthesis of the first intermediate 6-(4-(diphenylamino)phenyl)-9-ethylcarbazole-3-carbaldehyde (Suzuki coupling reaction):

[0063] 1.5mmol (455mg) of 6-bromo-9-ethyl-9H-carbazole-3-carbaldehyde and 2mmol (579mg) of 4-(diphenylamino)phenylboronic acid were dissolved in 35mL of toluene, 5mL of sodium carbonate solution (2M) was added, After stirring for 1 minute, 200 mg of tetrakis(triphenylphosphine)palladium(0) was added. The system was refluxed at 95°C for 45 hours under nitrogen protection. Then the mixed solution was washed with saturated salt solution, acid washed with dilute hydrochloric acid, and extracted with dichloromethane. The organic phase was separated, dried over anhydrous sodium sulfate and spun dry, and the crude product was purified by silica gel column chromatography with dichloromethane / n-hexane (2:1) as eluent. 608.9 mg of yellow solid product was obtained in 87% yield.

[0064] (2) Synthesis (condensation reaction) of the second intermediat...

Embodiment 2

[0076] (1) Synthesis of the first intermediate: 4-(4-(diphenylamino)phenyl)-benzaldehyde (Suzuki coupling reaction): the synthesis method is the same as that of step (1) in Example 1, and the yield is 90%.

[0077] (2) The third intermediate: 5,15-bis(1-(4-(diphenylamino)phenyl)-(phenyl-4-yl))-10,20-bis(2,4,6- Synthesis (condensation reaction) of trimethylphenyl) porphyrin: the synthesis method is the same as the step (3) of Example 1. Yield 8.0%, purple solid.

[0078] (3) Compound TPA-Ph-CoPor: 5,15-bis(1-(4-(diphenylamino)phenyl)-(phenyl-4-yl))-10,20-bis(2,4, Synthesis of 6-trimethylphenyl)cobalt(II) porphyrin (coordination reaction): the synthesis method is the same as that of the compound TPA-Cb-CoPor in Example 1, the yield is 94.0%, and it is a dark red solid.

[0079] The specific process is as follows:

[0080]

[0081] Preparation of carbon material-supported triphenylamine-based cobalt porphyrin composite catalyst: Disperse a mixture of 3 mg of compound TPA-Ph...

Embodiment 3

[0085] (1) The first intermediate: 7-(4-(diphenylamino)phenyl)benzo[c][1,2,5]thiadiazole-4-carbaldehyde (g): the synthesis method is the same as that in Example 1 of step (1) in 88% yield.

[0086] (2) The third intermediate: 5,15-bis(3-(4-(diphenylamino)phenyl)-(2,1,3-benzothiadiazol-4-yl))-10,20 -Two (2,4,6-trimethylphenyl) porphyrin (condensation reaction): the synthetic method is the same as the step (3) of embodiment 1. Yield 12.3%, purple solid.

[0087] (3) Compound TPA-BTD-CoPor: 5,15-bis(3-(4-(diphenylamino)phenyl)-(2,1,3-benzothiadiazol-4-yl))-10 , 20-bis(2,4,6-trimethylphenyl) cobalt (II) porphyrin synthesis (coordination reaction): the synthesis method is the same as the compound TPA-Cb-CoPor of Example 1, the yield is 89%, dark red solid,

[0088] The specific process is as follows:

[0089]

[0090] Preparation of carbon material-supported triphenylamine-based cobalt porphyrin composite catalyst: Disperse a mixture of 3 mg of compound TPA-BTD-CoPor and 10...

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Abstract

The invention belongs to the technical field of electrocatalytic oxygen reduction to produce hydrogen peroxide, and in particular relates to a triphenylamine-based cobalt porphyrin catalyst and a preparation method thereof, a triphenylamine-based cobalt porphyrin-modified carbon material composite catalyst, a preparation method and application thereof. The invention provides a triphenylamine-based cobalt porphyrin catalyst. Different conjugated linking groups can be inserted between the triphenylamine and the porphyrin ring. According to the electron donating and withdrawing characteristics of the linking group, the interface of the cobalt porphyrin molecule will be The state of charge changes. The catalyst provided by the invention contains a triphenylamine group and a cobalt porphyrin ring at the same time, and the catalyst with this structure can enhance the ORR performance of the triphenylamine-based cobalt porphyrin composite catalyst supported on carbon materials, and improve the selectivity of hydrogen peroxide.

Description

technical field [0001] The invention belongs to the technical field of electrocatalytic oxygen reduction to produce hydrogen peroxide, and in particular relates to a triphenylamine-based cobalt porphyrin catalyst and a preparation method thereof, a triphenylamine-based cobalt porphyrin modified carbon material composite catalyst, and a preparation method and application thereof. Background technique [0002] As a commercial chemical product, hydrogen peroxide is widely used in the fields of organic synthesis, pharmaceutical disinfection, pulp bleaching, wastewater treatment and new clean energy. At present, industrial hydrogen peroxide is mainly produced by the anthraquinone method. The disadvantages of this production method are 1) large investment in infrastructure and high energy consumption, 2) excessive hydrogenation in the production process to continuously degrade anthraquinone, 3 ) The coexistence of organic solvents and high concentrations of hydrogen peroxide will ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C25B11/095C25B1/30C07D487/22
CPCC25B11/095C25B1/30C07D487/22
Inventor 赵龙徐庆祥马雨涵袁蕊
Owner JIANGSU UNIV
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