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Oxidation of Phenols to Quinones

Oxidation of Phenols to Quinones

In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...

Radical Chain-Growth Polymerization: Overview

Radical Chain-Growth Polymerization: Overview

Chain-growth or addition polymerization is successive addition reactions of monomers with a polymer chain. In radical chain-growth polymerization, the reaction proceeds via a free-radical intermediate. The free radical is formed from radical initiators, which spontaneously generate free radicals by homolytic fission. Organic peroxides (such as dibenzoyl peroxide, as shown in Figure 1) or azo compounds are popular radical initiators. A low concentration ratio of radical initiator to monomer is...

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is...

Reactions at the Benzylic Position: Oxidation and Reduction

Reactions at the Benzylic Position: Oxidation and Reduction

The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.

Benzene to Phenol via Cumene: Hock Process

Benzene to Phenol via Cumene: Hock Process

The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene...

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Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Published on: November 21, 2017

Oxidative Depolymerization of Polyphenylene Oxide into Benzoquinone.

Yoshihiro Shimoyama¹, Yumiko Nakajima^1,2

¹Interdisciplinary Research Center for Catalytic Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), 1-1-1 Higashi, Tsukuba, Ibaraki, 305-8565, Japan.

|September 29, 2023

Summary

This summary is machine-generated.

Chemical recycling of Poly(2,6-dimethyl-1,4-phenylene oxide) (PPO) yields 2,6-dimethyl-p-benzoquinone (26DMBQ) via oxidative depolymerization. This upgraded PPO recycling process creates a valuable intermediate for polyimide synthesis.

Keywords:

Hydrogen Peroxide Oxidative Depolymerization Polyphenylene Oxide Silicotungstic acid Yttrium Nitrate

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Development of Efficient OLEDs from Solution Deposition

Development of Efficient OLEDs from Solution Deposition

Published on: November 4, 2022

Area of Science:

Polymer Chemistry
Green Chemistry
Materials Science

Background:

Poly(2,6-dimethyl-1,4-phenylene oxide) (PPO) is a widely used engineering plastic.
Efficient and sustainable recycling methods for PPO are crucial for resource management.

Purpose of the Study:

To develop a chemical recycling process for PPO.
To achieve oxidative depolymerization of PPO into valuable aromatic compounds.
To demonstrate an upgrade pathway for recycled PPO.

Main Methods:

Oxidative depolymerization of PPO using nitronium ions (NO2+) as a mild oxidant.
Generation of NO2+ from silicotungstic acid and nitrate salts.
Purification of the product via sublimation.

Main Results:

Achieved a 66% yield of 2,6-dimethyl-p-benzoquinone (26DMBQ) as the sole aromatic product.
Mechanistic studies elucidated the C-O bond cleavage pathway.
Obtained pure 26DMBQ through sublimation.

Conclusions:

Developed an effective oxidative depolymerization method for PPO recycling.
Demonstrated the successful conversion of PPO into 26DMBQ.
Showcased the potential of 26DMBQ for synthesizing high-performance polyimides, establishing an upgrade recycling process.