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Synthetic method for preparing diphenyl sulfoxide-containing compound through electrochemical catalytic oxidation

A diphenyl sulfoxide, catalytic oxidation technology, applied in electrolysis process, electrolysis components, electrolysis organic production, etc., can solve the problems of long reaction time, low conversion rate, unsuitable for industrial production, etc., to achieve improved conversion rate, low energy Consumption, improve the effect of atomic utilization

Pending Publication Date: 2022-03-29
NINGBO NATA OPTO ELECTRONICS MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method requires inert gas protection, the reaction time is long, the conversion rate is low, and it is not suitable for industrial production (see Synthesis, 2017, vol.49, #21, p.4769-4774 for details)

Method used

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  • Synthetic method for preparing diphenyl sulfoxide-containing compound through electrochemical catalytic oxidation
  • Synthetic method for preparing diphenyl sulfoxide-containing compound through electrochemical catalytic oxidation
  • Synthetic method for preparing diphenyl sulfoxide-containing compound through electrochemical catalytic oxidation

Examples

Experimental program
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Effect test

Embodiment 1

[0061] The electrochemical catalytic oxidation of the present embodiment prepares the synthetic method that contains diphenyl sulfoxide compound, reaction equipment such as figure 1 middle:

[0062] 1) A is the substrate (i) solution, and the substrate is dissolved in an organic solvent, wherein the organic solvent is: methanol, ethanol, isopropanol, ethyl acetate, isopropyl acetate, tert-butyl acetate, sec-butyl acetate One of ester, dimethyltetrahydrofuran, tetrahydrofuran, acetonitrile, acetone, butanone, cyclohexanone, tert-butyl methyl ether, ethylene glycol monomethyl ether, ethylene glycol dimethyl ether, anisole, NMP, toluene or Several kinds. Preference is given to acetonitrile, methanol, dichloromethane, acetone and small amounts of catalysts.

[0063] The oxidant is: one or more of hydrogen peroxide, sodium hypochlorite, sodium chlorobromide, oxygen, ozone, air, peroxide, and potassium dichromate. Preferably hydrogen peroxide, oxygen, sodium hypochlorite, air;

...

Embodiment 2

[0090] The electrochemical catalytic oxidation of this embodiment prepares the synthetic method of containing diphenyl sulfoxide compound, and equipment is the same as embodiment 1, and only difference is, A in the figure is feed inlet: substrate is 10% diphenyl sulfide For the methanol solution of ether, 10% refers to the mass ratio of the substrate weight to the solvent, F is the inlet of the mixed gas, and the mixed gas is air. Enter the electrochemical device at a gas velocity of 1.0 m / s. Electrode C is the graphite anode electrode of DC power supply, adjust the appropriate voltage, under the action of the mixed gas, the oxygen content is reduced from 18%-21% (volume) to 13%-15% (volume), and the single oxygen consumption is 30%, finally collect the reaction solution and add a reducing agent such as: sodium thiosulfate, sodium dithionite, sodium sulfite, potassium sulfite, sodium borohydride, etc.) to quench the reaction, and the reaction solution HPLC detection: Agilent 1...

Embodiment 3

[0092]

[0093]The electrochemical catalytic oxidation of the present embodiment prepares the synthetic method of the compound containing diphenyl sulfoxide, and the equipment is used in Example 1. The only difference is that A in the figure is the feed port: the substrate is diphenyl sulfide Methanol solution, where the substrate concentration needs to be controlled within the concentration range of 3-20%, the substrate concentration is the mass ratio of the substrate to the solvent, F is the inlet of the mixed gas, and the mixed gas is oxygen and nitrogen. Enter the electrochemical device at a gas velocity of 0.1 m / s. Electrode C is a graphite anode electrode of DC power supply, adjust the appropriate voltage, under the action of the mixer, the oxygen content is reduced from 80%-82% (volume) to 28-51% (volume), and the single oxygen consumption is 37.5 %, the final mobile phone reaction solution was added a reducing agent to quench the reaction, and the reaction solution ...

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Abstract

The invention discloses a synthetic method for preparing a compound containing diphenyl sulfoxide through electrochemical catalytic oxidation, which is characterized in that the synthetic reaction formula is as follows: R1 and R2 are hydrogen, alkyl or alkyl; the catalyst is a compound composed of a metal catalyst and a ligand thereof; the oxidizing agent comprises peroxide, chlorate, dichromate, inorganic acid and a mixture of one or two of oxygen, ozone and air; the reaction is carried out in an organic solvent. The method is high in conversion rate and low in cost.

Description

technical field [0001] The invention relates to a synthesis method for preparing diphenyl sulfoxide-containing compounds by electrochemical catalytic oxidation. Background technique [0002] Triphenylsulfonium salt and its derivative photoacid generators have high acid production efficiency and good thermal stability due to their special structure, and are extremely important in photoresists and photosensitive materials. Applications. Diphenyl sulfoxide compound is an important key raw material for the preparation of triphenylsulfonium salts. The existing technology for preparing diphenyl sulfoxide-containing compounds is to use phenyl sulfide as a starting material. Under the action of a catalyst, the The solution is mixed and reacted with an oxidizing agent to obtain a reaction solution containing phenylsulfoxide compound. The defects in the scheme of preparing diphenylsulfoxide-containing compounds in the prior art are as follows: [0003] Example 1) Preparation of 4,4...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/07C25B3/01C25B3/23
CPCC25B3/07C25B3/01C25B3/23
Inventor 夏力顾大公马潇陈鹏许从应毛智彪
Owner NINGBO NATA OPTO ELECTRONICS MATERIAL CO LTD
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