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Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...

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...

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

Reduction of Alkenes: Catalytic Hydrogenation

Reduction of Alkenes: Catalytic Hydrogenation

Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

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...

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Recent progress on selective hydrogenation of phenol toward cyclohexanone or cyclohexanol.

Guangxin Xue¹, Linlin Yin^1,2, Shengxian Shao^1,3

¹CAS Key Laboratory of Nanosystem and Hierarchical Fabrication, CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology, Beijing 100190, People's Republic of China.

|November 10, 2021

Summary

Selective hydrogenation of phenol to cyclohexanone and cyclohexanol is crucial for nylon production. This review summarizes nanocatalyst progress, mechanisms, and scale-up challenges for industrial application.

Keywords:

cyclohexanol cyclohexanone metal nanocatalysts selective hydrogenation of phenol synergistic catalysis

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Hydrogen Production and Utilization in a Membrane Reactor

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Published on: March 10, 2023

Area of Science:

Catalysis
Materials Science
Chemical Engineering

Background:

Phenol is a vital platform molecule for chemical synthesis.
Selective hydrogenation of phenol yields cyclohexanone and cyclohexanol (KA oil), key nylon precursors.
Industrial application of phenol hydrogenation remains challenging.

Purpose of the Study:

To review recent advancements in selective phenol hydrogenation using nanocatalysts.
To analyze the relationship between catalyst properties (active components, supports) and performance.
To discuss reaction mechanisms, scale-up strategies, and future outlooks for phenol hydrogenation.

Main Methods:

Literature review of selective hydrogenation of phenol.
Analysis of various nanocatalysts, including active components and supports.
Discussion of reaction mechanisms and scale-up feasibility.

Main Results:

Summary of different nanocatalysts for selective phenol hydrogenation.
Exploration of structure-performance relationships in nanocatalysts.
Identification of challenges and opportunities for industrial implementation.

Conclusions:

Nanocatalysts offer promising routes for selective phenol hydrogenation.
Understanding catalyst-support interactions is key for optimizing performance.
Further research is needed to overcome scale-up hurdles and enable industrialization.