Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for catalyzing oxidation of phenol and hydrogen peroxide with selenium-containing catalyst for synthesis of p-benzoquinone

A technology for catalyzing phenol and oxidative synthesis with a catalyst, which is applied in the preparation of quinone oxide, chemical instruments and methods, catalysts for physical/chemical processes, etc., and can solve the problems of manganese sulfate and ammonium sulfate waste liquid being difficult to handle, equipment corrosion, and increasing production costs. , to achieve the effect of solving difficult separation and easy loss, mild process conditions and low equipment requirements

Active Publication Date: 2017-04-26
JIANGSU YANGNONG CHEM GROUP +2
View PDF5 Cites 9 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the problem of this method is that the consumption of pyrolusite is large, and a large amount of manganese sulfate and ammonium sulfate waste liquid are difficult to handle during the production process, which seriously pollutes the environment; on the other hand, the acidic system has a corrosive effect on equipment and increases production costs.
CN103420803B, using ozone as an oxygen source also has safety risks
[0005] There are also researchers exploring the phenol hydrogen peroxide oxidation method, such as CN103570506B, using phenol and hydrotalcite (catalyst), adding hydrogen peroxide, but in addition to obtaining p-benzoquinone, there is also o-benzoquinone in the product, which requires the separation of isomers and subsequent treatment relatively cumbersome;
[0006] There are also researchers who use hydroquinone as a raw material to synthesize p-benzoquinone, such as CN104844439A, etc., because the price of hydroquinone is quite different from p-benzoquinone, so this method is not economical

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for catalyzing oxidation of phenol and hydrogen peroxide with selenium-containing catalyst for synthesis of p-benzoquinone

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0018] Preparation process of supported selenium catalyst

[0019] In order to better illustrate the preparation process of the supported selenium catalyst, its preparation process is briefly introduced now (see J.Mater.Chem.A, 2016,4,10828-10833): under nitrogen protection, 4g polystyrene resin in 30mL ring Soak in hexene, then add tetramethylethylenediamine (37.2mmol, 5.6ml) and n-butyllithium (48mmol, 26.7ml), stir, heat up to 65-70°C, react for 4hr, filter, filter cake with 30mL Wash with THF, transfer the filter cake to a reaction flask, add 40ml THF, cool to 0°C, add dimethyl diselenide (5mmol), stir for 20min, add 3mL water, the polymer gradually changes from brown to yellow, filter , the filter cake was washed successively with THF, water and methanol, and then dried under vacuum at 65° C. for 24 hrs to obtain a pure polymer-supported methylselenide resin.

[0020] Under nitrogen protection, soak 4g of methylselenide-based resin in 60ml of chloroform, then add bromine...

Embodiment 1

[0023] Add 1.65g of phenol, 11g of ethanol, 9.9g of 30wt% hydrogen peroxide and 16.5mg of phenylselenous acid into a 30ml glass reaction vial, and raise the temperature in a water bath to 60°C under magnetic stirring for 2 hours. After cooling down to room temperature, 21.5 g of oxidizing solution was obtained. Sampling and analyzing the composition of the oxidizing solution showed 4.97% phenol and 2.58% p-benzoquinone. As a result, the conversion rate of phenol was 35.24%, and the selectivity to p-benzoquinone was 83.03%.

Embodiment 2

[0025] Add 1.8g of phenol, 10g of acetonitrile, 10g of 25wt% hydrogen peroxide and 12mg of diphenyldiselenide into a 30ml glass reaction vial, and raise the temperature to 70°C in a water bath under magnetic stirring for 1.5 hours. After cooling down to room temperature, 20.4 g of oxidizing solution was obtained. Sampling and analyzing the composition of the oxidizing solution showed 5.16% phenol and 3.59% p-benzoquinone. As a result, the conversion rate of phenol was 41.52%, and the selectivity to p-benzoquinone was 85.29%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
melting pointaaaaaaaaaa
Login to View More

Abstract

The invention relates to a method for catalyzing oxidation of phenol and hydrogen peroxide with a selenium-containing catalyst for synthesis of p-benzoquinone. The method is mild in reaction conditions and can be implemented at normal pressure. According to a technical scheme in the invention, the method comprises the following steps: adding phenol, a solvent, the selenium-containing catalyst and hydrogen peroxide into a glass reaction bottle and carrying out a reaction at a certain temperature, wherein analysis results of oxidized liquid show that the conversion rate of phenol is about 30 to 50%, the selectivity of p-benzoquinone is 80 to 90% and resorcinol and ortho-isomers are not produced. High-selectivity preparation of hydroquinone can be realized through hydrogenation reduction of p-benzoquinone.

Description

technical field [0001] The invention relates to a method for synthesizing p-benzoquinone by catalyzing the oxidation of phenol hydrogen peroxide by a selenium-containing catalyst. Background technique [0002] p-Benzoquinone, yellow crystal. Flammable, melting point 116°C, relative density 1.318g / ml, soluble in ethanol, ether and alkali, slightly soluble in water. Can sublime, its vapor is volatile and partially decomposed. Has a pungent chlorine-like odor. It is an important dye and pharmaceutical intermediate, used as a raw material for the manufacture of hydroquinone and rubber anti-aging agents, as acrylonitrile and vinyl acetate polymerization initiators and oxidants. [0003] The production process of p-benzoquinone is mainly the aniline oxidation method. Aniline in H 2 SO 4 MnO 2 or Na 2 Cr 2 o 7 Oxidation to p-benzoquinone, the advantage of this method is that the process is mature. However, the problem of this method is that the consumption of pyrolusite ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C46/06C07C50/04B01J31/06
CPCB01J31/06B01J2231/70C07C46/06C07C50/04
Inventor 王芳孙诚俞磊徐林邹爱宗陶文波吴宇冰
Owner JIANGSU YANGNONG CHEM GROUP
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com