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Electrochemical regeneration method of chloranil by taking halogen ions as electric catalyst

A technology of tetrachlorobenzoquinone and electrocatalyst, which is applied in the field of electrochemical regeneration of tetrachlorobenzoquinone, can solve the problems of no domestic and foreign literature reports on regeneration of tetrachlorobenzoquinone, complicated post-treatment, and high equipment requirements, and achieves low cost, The effect of simple and convenient post-processing and simple reaction equipment

Active Publication Date: 2018-11-13
BEIJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009](1) The use of double-chamber electrolyzers requires high equipment;
[0010](2) Using acetonitrile as a solvent, the cost is high and the post-treatment is complicated;
[0011](3) Using expensive lithium perchlorate as a supporting electrolyte, the cost is high, and a large amount of high-salt wastewater is produced after electrolysis
[0012] At present, the method of electrochemical regeneration of chlorobenzoquinone by halide ion as electrocatalyst has not yet been reported in domestic and foreign literature

Method used

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  • Electrochemical regeneration method of chloranil by taking halogen ions as electric catalyst
  • Electrochemical regeneration method of chloranil by taking halogen ions as electric catalyst
  • Electrochemical regeneration method of chloranil by taking halogen ions as electric catalyst

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Embodiment 1: take the halide ion as the electrochemical regeneration method of the chlorobenzoquinone of electrocatalyst

[0031] In a 50ml single-chamber electrolytic cell, 1240mg (5.0mmol) of tetrachlorohydroquinone and 1030mg (10mmol) of sodium bromide were added to 15ml of methanol solvent, and a small amount of hydrobromic acid was added to make the pH of the reaction system 1-2. With graphite sheet electrode as anode and stainless steel mesh as cathode, at 9mA / cm 2 Electrolyze at a constant current and stir at 25°C. When the energized amount reaches about 4.0 F / mol, the raw materials are basically reacted, and the electrolysis is stopped. The reaction solution is filtered to obtain a yellow solid, which is the product chlorobenzoquinone. Yield: 75%.

Embodiment 2

[0032] Embodiment 2: take the halide ion as the electrochemical regeneration method of the chlorobenzoquinone of electrocatalyst

[0033] In a 50ml single-chamber electrolytic cell, 1240mg (5.0mmol) of tetrachlorohydroquinone and 515mg (5.0mmol) of sodium bromide were added to 15ml of methanol solvent, and a small amount of hydrobromic acid was added to make the pH of the reaction system 1-2. With graphite sheet electrode as anode and stainless steel mesh as cathode, at 9mA / cm 2 Electrolyze at a constant current and stir at 25°C. When the energized amount reaches about 4.0 F / mol, a large amount of raw materials remain, stop the electrolysis, and filter the reaction solution to obtain a yellow solid, which is the product chloranil. Yield: 10%.

Embodiment 3

[0034] Embodiment 3: take the halide ion as the electrochemical regeneration method of the chlorobenzoquinone of electrocatalyst

[0035] In a 50 ml single-chamber electrolytic cell, 1240 mg (5.0 mmol) of tetrachlorohydroquinone and 515 mg (5.0 mmol) of sodium bromide were added to 15 ml of methanol solvent. With graphite sheet electrode as anode and stainless steel mesh as cathode, at 9mA / cm 2 Electrolyze at a constant current and stir at 25°C. When the energized amount reaches about 4.0 F / mol, the raw materials are basically reacted, and the electrolysis is stopped. A dark green solid is attached to the cathode. The reaction solution is filtered to obtain a yellow solid, which is the product Chlorobenzoquinone. Yield: 81%.

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Abstract

The invention relates to an electrochemical regeneration method of chloranil by taking halogen ions as an electric catalyst, and belongs to the technical field of chloranil. The method mainly uses alkali metal halide as the electric catalyst and alcohol as a solvent, and the chloranil is regenerated by indirect electrooxidation recovery of tetrachloro hydroquinone. According to the electrochemicalmethod of the chloranil, the cost is low, the required reaction equipment is simple, the post-treatment is simple and convenient, and when a theoretical electric quantity is introduced, the yield ofthe chloranil can reach about 50%, when the electric quantity is increased by 2 times, raw materials can be basically completely reacted, and the yield is over 80%, the reaction solvent can be repeatedly recycled, no sewage is generated, green and environment-friendly effects are achieved, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for electrochemically regenerating chloranil when a halide ion is an electrocatalyst, and belongs to the technical field of chloranil. Background technique [0002] Quinones are important redox-active organic molecules that can be applied in different redox processes, including the manufacture of industrial chemicals, oxidation reactions in organic synthesis, and also as electron carriers, antioxidants, and cofactors in biological processes. Quinone has three readily accessible oxidation states, fully oxidized quinone, one-electron reduced semiquinone, and two-electron reduced hydroquinone, and they are able to neutralize both closed-shell and open-shell redox processes as follows: [0003] [0004] Quinone oxidants, such as DDQ, chloranil, etc., are widely used in medicinal chemistry and synthetic chemistry. They have a very wide range of uses in the activation of C-H bonds and the dehydrogenation of saturated C-C,...

Claims

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Application Information

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IPC IPC(8): C25B3/02C25B11/06C25B3/23
CPCC25B11/04C25B3/23Y02P20/584
Inventor 曾程初李勇
Owner BEIJING UNIV OF TECH
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