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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...

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.

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

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...

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A Simple, Low-cost, and Robust System to Measure the Volume of Hydrogen Evolved by Chemical Reactions with Aqueous Solutions

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Published on: August 17, 2016

Ruthenium and Platinum-Modified Titanium Dioxide Support for NaBH₄ Hydrolysis.

Cigdem Tuc Altaf¹, Valentina G Minkina², Stanislav I Shabunya²

¹Micro and Nanotechnology Graduate Program, TOBB University of Economics and Technology, Sogutozu Caddesi no. 43, Sogutozu 06560, Ankara, Turkey.

|October 9, 2023

Summary

Highly stable platinum and ruthenium catalysts on titanium dioxide nanoparticles efficiently generate hydrogen from sodium borohydride hydrolysis, achieving 95% productivity. Catalyst performance varied with solution alkalinity and sodium hydroxide concentration.

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Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes

Published on: June 24, 2022

Area of Science:

Materials Science
Catalysis
Chemical Engineering

Background:

Hydrogen generation is crucial for clean energy. Sodium borohydride hydrolysis offers a promising route.
Developing efficient and stable catalysts is key for practical hydrogen production.

Purpose of the Study:

To prepare and characterize platinum (Pt) and ruthenium (Ru)-based catalysts supported on titanium dioxide (TiO2) nanoparticles.
To investigate the hydrogen generation rate (HGR) and activation energy of sodium borohydride (NaBH4) hydrolysis using these catalysts.
To evaluate the effect of alkaline conditions and NaOH concentration on catalyst performance.

Main Methods:

Synthesis of Pt/TiO2 and Ru/TiO2 nanoparticle catalysts.
Hydrogen generation experiments using NaBH4 hydrolysis.
Kinetic analysis including activation energy determination.
Systematic variation of NaOH concentration (0.5-2 M) to study its impact on HGR.

Main Results:

High hydrogen generation productivity (up to 95%) was achieved with the prepared catalysts.
Ru/TiO2 catalysts showed activation energies of 62.00 kJ mol-1 (aqueous) and 64.65 kJ mol-1 (alkaline).
Pt/TiO2 catalysts exhibited a decrease in activation energy from 60.5 kJ mol-1 (aqueous) to 53.2 kJ mol-1 (alkaline).
HGR with Ru/TiO2 decreased as NaOH concentration increased.
HGR with Pt/TiO2 increased with increasing NaOH concentration.

Conclusions:

Pt/TiO2 and Ru/TiO2 catalysts demonstrate high efficiency for hydrogen generation from NaBH4 hydrolysis.
Catalyst performance is significantly influenced by solution pH and NaOH concentration.
Pt/TiO2 shows enhanced activity in alkaline media with increasing NaOH concentration, while Ru/TiO2 performance degrades.