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Triphenylamine cobalt porphyrin catalyst and preparation method and application thereof

A triphenylamine-based cobalt porphyrin and catalyst technology, applied in the field of electrocatalytic oxygen reduction to produce hydrogen peroxide, can solve the problems of changing the concentration of protons on the catalytic interface, increasing the risk of explosion, and the impact of oxygen adsorption, and achieve good electrocatalysis Oxygen reduction activity, enhanced hydrogen peroxide selectivity, high hydrogen peroxide selectivity effect

Active Publication Date: 2021-09-21
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • Triphenylamine cobalt porphyrin catalyst and preparation method and application thereof
  • Triphenylamine cobalt porphyrin catalyst and preparation method and application thereof
  • Triphenylamine cobalt porphyrin catalyst and preparation method and application thereof

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, and 5mL of sodium carbonate solution (2M) was added, Stir for 1 minute, then add 200 mg tetrakis(triphenylphosphine)palladium(0). The system was refluxed at 95° C. for 45 hours under the protection of nitrogen. Then the mixed solution was washed with saturated saline solution, acid-washed with dilute hydrochloric acid, and extracted with dichloromethane. The organic phase was separated, dried over anhydrous sodium sulfate and spin-dried, and the crude product was purified by silica gel column chromatography, and the eluent was dichloromethane / n-hexane (2:1). 608.9 mg of a yellow solid product was obtained with a yield of 87%.

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

Embodiment 2

[0076] (1) The first intermediate: the synthesis of 4-(4-(diphenylamino)phenyl)-benzaldehyde (Suzuki coupling reaction): the synthesis method is the same as the step (1) of 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- The synthesis (condensation reaction) of trimethylphenyl) porphyrin: synthetic method is with the step (3) of embodiment 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 (coordination reaction) of 6-trimethylphenyl) cobalt (II) porphyrin: the synthesis method is the same as that of the compound TPA-Cb-CoPor in Example 1, with a yield of 94.0%, dark red solid.

[0079] The specific process is as follows:

[0080]

[0081] Preparation of carbon material-loaded triphenylamine-based cobalt porphyrin composite catalysts: respectively disperse a mixture of 3mg compound TPA-Ph-CoP...

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 in Example 1 Step (1), yield 88%.

[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): synthetic method is the same as embodiment 1 step (3). 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 , the synthesis (coordination reaction) of 20-two (2,4,6-trimethylphenyl) cobalt (II) porphyrin: synthetic method is the same as embodiment 1 compound TPA-Cb-CoPor, productive rate 89%, dark red solid,

[0088] The specific process is as follows:

[0089]

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

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Abstract

The invention belongs to the technical field of production of hydrogen peroxide through electrocatalytic oxygen reduction, and particularly relates to a triphenylamine cobalt porphyrin catalyst and a preparation method thereof, and a triphenylamine cobalt porphyrin modified carbon material composite catalyst and a preparation method and application thereof. According to the triphenylamine cobalt porphyrin catalyst provided by the invention, different conjugated linking groups can be inserted between triphenylamine and a porphyrin ring, and the interface charge state of cobalt porphyrin molecules can be changed according to the electron supply and withdrawing characteristics of the linking groups. The catalyst provided by the invention simultaneously contains a triphenylamine group and a cobalt porphyrin ring, and the catalyst with the structure can enhance the ORR performance of the carbon material loaded triphenylamine cobalt porphyrin composite catalyst and improve the hydrogen peroxide selectivity.

Description

technical field [0001] The invention belongs to the technical field of hydrogen peroxide production by electrocatalytic oxygen reduction, 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. Background technique [0002] As a commercial chemical product, hydrogen peroxide is widely used in organic synthesis, medical disinfection, pulp bleaching, wastewater treatment and new clean energy. 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...

Claims

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Application Information

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Patent Type & Authority Applications(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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