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Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

Preparation of Alcohols via Addition Reactions

Preparation of Alcohols via Addition Reactions

Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.

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...

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...

Electrophilic Aromatic Substitution: Sulfonation of Benzene

Electrophilic Aromatic Substitution: Sulfonation of Benzene

Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.

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Related Experiment Video

Updated: Jan 11, 2026

Proof-of-Concept for Gas-Entrapping Membranes Derived from Water-Loving SiO2/Si/SiO2 Wafers for Green Desalination

Proof-of-Concept for Gas-Entrapping Membranes Derived from Water-Loving SiO2/Si/SiO2 Wafers for Green Desalination

Published on: March 1, 2020

Liquid Sorption-Enhanced Haber-Bosch Process.

Nicholas E Thornburg¹, Jacob H Miller², William Xi³

¹Energy Conversion and Storage Systems Center, National Renewable Energy Laboratory, 15013 Denver West Parkway, Golden, Colorado 80401, United States.

Industrial & Engineering Chemistry Research

|November 10, 2025

Summary

A novel liquid sorbent using phosphoric acid effectively absorbs and releases ammonia in the Haber-Bosch process. This innovation promises significant energy savings and cost reductions for ammonia synthesis.

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Area of Science:

Chemical Engineering
Materials Science
Sustainable Chemistry

Background:

The Haber-Bosch process is crucial for ammonia synthesis but is highly energy-intensive.
Traditional ammonia separation methods contribute significantly to the process's energy demands.

Purpose of the Study:

To develop and validate a liquid sorption system for ammonia separation in the Haber-Bosch process.
To improve the energy efficiency and reduce the cost of ammonia production.

Main Methods:

Investigated reactions between ammonia and phosphoric acid to form a reversible sorbent (MAP/DAP).
Conducted proof-of-concept absorption and desorption experiments in batch reactors.
Developed thermodynamic relationships and validated them with ReaxFF simulations and process modeling.

Main Results:

Demonstrated a liquid sorbent system capable of absorbing and releasing ammonia under process-relevant conditions.
Established thermodynamic principles governing the novel separation strategy.
Process modeling indicated potential for enhanced energy efficiency compared to traditional methods.

Conclusions:

The liquid sorption approach offers a promising pathway to significantly improve the energy efficiency of the Haber-Bosch process.
This method provides a regenerable and efficient means for ammonia separation, contributing to sustainable chemical production.