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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.

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.

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

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...

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Updated: Apr 26, 2026

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

Efficient and selective hydrogen generation from bioethanol using ruthenium pincer-type complexes.

Peter Sponholz¹, Dörthe Mellmann, Christoph Cordes

¹Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany), Fax: (+49) 381-1281-5000.

|August 5, 2014

Summary

This study demonstrates efficient hydrogen production from bioethanol using a ruthenium catalyst. The process selectively yields acetic acid and hydrogen suitable for proton exchange membrane fuel cells.

Keywords:

acetic acid homogeneous catalysis hydrogen generation renewable resources ruthenium

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The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

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Hydrogen Production and Utilization in a Membrane Reactor

Hydrogen Production and Utilization in a Membrane Reactor

Published on: March 10, 2023

Area of Science:

Catalysis
Green Chemistry
Renewable Energy

Background:

Hydrogen production is crucial for clean energy.
Ethanol dehydrogenation offers a sustainable pathway.
Pincer-type catalysts show promise for efficient reactions.

Purpose of the Study:

To investigate catalytic hydrogen generation from aqueous ethanol.
To optimize catalyst performance and selectivity.
To assess the direct use of bioethanol in the process.

Main Methods:

Utilized a pincer-type ruthenium complex ([Ru(H)(Cl)(CO)(iPr2PEtN(H)EtPiPr2)]) as a catalyst.
Conducted dehydrogenation of aqueous ethanol solutions in the presence of base.
Analyzed reaction products for hydrogen, acetic acid, and carbon monoxide.

Main Results:

Achieved high catalyst turnover number (TON 80,000).
Generated up to 70% acetic acid selectively.
Demonstrated direct utilization of unpurified bioethanol, eliminating water removal steps.
Produced hydrogen with very low carbon monoxide content.

Conclusions:

The developed catalytic system efficiently produces hydrogen from bioethanol.
The process is suitable for direct use of fermentation-derived bioethanol.
The generated hydrogen is compatible with proton exchange membrane fuel cells.