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Method for preparing aromatic aldehyde/ketone compound based on photoelectrocatalysis

A technology of photoelectric catalysis and ketone compounds, which is applied in the field of synthesis of aromatic aldehyde/ketone compounds to achieve the effects of reducing pollution, mild reaction conditions, and low requirements for reaction equipment

Active Publication Date: 2016-04-06
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there is no relevant literature report on the preparation of aromatic aldehyde / ketone compounds based on photoelectric indirect catalysis.

Method used

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  • Method for preparing aromatic aldehyde/ketone compound based on photoelectrocatalysis
  • Method for preparing aromatic aldehyde/ketone compound based on photoelectrocatalysis
  • Method for preparing aromatic aldehyde/ketone compound based on photoelectrocatalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] reaction system:

[0038] Anolyte: mix 5uL p-methylanisole with 65mL of 0.12mol / L Ce 2 (SO 4 ) 3 Nitric acid solution (nitric acid concentration 1.0mol / L) mixed; wherein, 0.12mol / L of Ce 2 (SO 4 ) 3 The preparation method of the nitric acid solution is as follows: at 25° C., weigh 68.2 g of cerous sulfate octahydrate, and measure 69 ml of concentrated nitric acid (65 wt %) to prepare a 1.0 L aqueous solution.

[0039] Catholyte: 1.0mol / L nitric acid solution;

[0040] Anode: TiO 2 / FTO thin film electrode;

[0041] TiO 2 / Preparation of FTO film electrode: Mix 30mL ultrapure water and 30mL concentrated hydrochloric acid, then add 2.0mL isopropyl titanate dropwise and transfer them to a hydrothermal kettle together, then put the washed FTO glass slide. The hydrothermal kettle was hydrothermally heated at 155°C for 4 hours. After cooling, take out the FTO and wash it, and heat it in a muffle furnace at 200°C for 2 hours to obtain TiO 2 / FTO.

[0042] Cathode: ...

Embodiment 2

[0048] reaction system:

[0049] Anolyte: mix 5uL p-chlorotoluene with 65mL of 0.12mol / L Ce 2 (SO 4 ) 3 Nitric acid solution mixed (nitric acid concentration 1.0mol / L);

[0050] Catholyte: 1.0mol / L nitric acid solution;

[0051] Anode: TiO 2 / FTO thin film electrode;

[0052] Cathode: Pt;

[0053] Reference electrode: mercury-mercurous sulfate;

[0054] Reactor such as figure 2 As shown, the cathode was exhausted with nitrogen gas for 10 minutes, and the above reaction system was subjected to a bias voltage of 0.7V, a reaction temperature of 25°C, a light source of 300W xenon lamp to simulate sunlight, and a reaction time of 2 hours. After the reaction, the anolyte was extracted, and the organic phase was purified to obtain p-chlorobenzaldehyde (structural formula is shown below), the inorganic phase was recycled, and the cathode product was hydrogen.

[0055] Structural formula:

[0056]

Embodiment 3

[0058] reaction system:

[0059] Anolyte: mix 5uL ethylbenzene with 65mL of 0.12mol / L Ce 2 (SO 4 ) 3 Nitric acid solution mixed (nitric acid concentration 1.0mol / L);

[0060] Catholyte: 1.0mol / L nitric acid solution;

[0061] Anode: TiO 2 / FTO thin film electrode;

[0062] Cathode: Pt;

[0063] Reference electrode: mercury-mercurous sulfate;

[0064] Reactor such as figure 2 As shown, the cathode was exhausted with nitrogen gas for 10 minutes, and the above reaction system was subjected to a bias voltage of 0.7V, a reaction temperature of 25°C, a light source of 300W xenon lamp to simulate sunlight, and a reaction time of 2 hours. After the reaction, the anolyte is extracted, the organic phase is purified to obtain acetophenone (the structural formula is shown below), the inorganic phase is recycled, and the cathode product is hydrogen.

[0065] Structural formula:

[0066]

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Abstract

The invention relates to a method for preparing an aromatic aldehyde / ketone compound based on photoelectrocatalysis. A reaction system is included and comprises an anode solution obtained by mixing a compound in formula I and an acid solution of metal ions, a cathode solution, namely, an acid solution, an anode, namely, a photocatalyst film electrode, a cathode Pt and a reference electrode, namely, mercury-mercurous sulfate; the reaction system carries out a reaction for 1-8 h at the bias voltage of -0.3 V-0.9 V and at the temperature of 10-70 DEG C, then the anode solution is extracted, an organic phase is purified to obtain the compound in formula II, an inorganic phase is utilized cyclically, and a cathode product is hydrogen. The formulas are shown in the specification. Alkylated aromatic is indirectly and selectively oxidized into corresponding aldehyde / ketone through the photoelectrocatalysis technology and meanwhile hydrogen is generated by the cathode. Photoproduction electrons are separated from a hole through an optical excitation semiconductor, and the hole has the strong oxidizing property. Ce3+ or Mn2+ is oxidized into Ce4+ or Mn3+ in an aqueous solution through the photoproduction hole, the alkylated aromatic is oxidized into corresponding aldehyde / ketone through high-valence Ce4+ or Mn3+, and Ce4+ or Mn3+ is reduced into Ce3+ or Mn2+ to form a cycle. Meanwhile, H+ of H2O can be reduced into H2 through the photoproduction electrons.

Description

technical field [0001] The invention belongs to the technical field of synthesis of aromatic aldehyde / ketone compounds, in particular to a method for preparing aromatic aldehyde / ketone compounds based on photoelectric catalysis. Background technique [0002] In recent years, the use of semiconductor photocatalysis to prepare new energy sources and deal with environmental pollution has attracted worldwide attention. Since photocatalytic technology can directly use solar energy for reaction, there is almost no consumption of other energy sources, so more and more attention has been paid to organic synthesis, especially photocatalytic selective oxidation. However, the valence bands of general photocatalysts are relatively deep, and it is easy to directly mineralize organic matter. Many methods have been proposed to solve this problem. For example, the specific crystal facet of the catalyst is highly exposed to improve the selectivity of the catalyst; or the loaded noble metal...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/02C25B3/23
CPCC25B3/23
Inventor 朱建陆景鹏李丹金怡晨李和兴
Owner SHANGHAI NORMAL UNIVERSITY
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