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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.

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Hydrogen Production and Utilization in a Membrane Reactor

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Published on: March 10, 2023

Chemoselective and Continuous Flow Hydrogenations in Thin Films Using a Palladium Nanoparticle Catalyst Embedded in

Jessica M Phillips¹, Muneer Ahamed¹, XiaoFei Duan²

¹Flinders Institute for NanoScale Science and Technology, College of Science and Engineering, Flinders University, Bedford Park, South Australia 5042, Australia.

ACS Applied Bio Materials

|January 12, 2022

Summary

Simple, fast preparation of cellulose-supported palladium nanoparticles enables efficient, scalable catalytic hydrogenation of various organic compounds. This reusable catalyst offers high yields under mild conditions for fine chemical synthesis.

Keywords:

catalysis cellulose hydrogenation palladium vortex fluidics

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Published on: June 24, 2022

Area of Science:

Catalysis
Materials Science
Green Chemistry

Background:

Developing efficient and scalable catalytic systems is crucial for industrial chemical synthesis.
Palladium nanoparticles (PdNPs) are widely used catalysts, but their immobilization and reusability can be challenging.
Flow chemistry offers advantages for scalable and controlled reactions.

Purpose of the Study:

To develop a simple, fast, and scalable method for preparing cellulose-immobilized palladium (0) nanoparticles (PdNPs).
To evaluate the catalytic performance of the prepared PdNPs in various hydrogenation reactions.
To demonstrate the stability, reusability, and chemoselectivity of the catalyst for synthesizing fine chemicals.

Main Methods:

Drop-casting a palladium acetate solution onto cellulose paper.
Rapid reduction of palladium acetate to Pd(0) nanoparticles using hydrogen gas for 90 seconds.
Testing the catalyst in hydrogenation of alkenes, nitroarenes, ketones, and enamides under ambient conditions.
Evaluating transfer hydrogenation using ammonium formate as a hydrogen source.

Main Results:

Successfully prepared cellulose-immobilized Pd(0) nanoparticles through a simple and rapid 90-second process.
Achieved high yields in the hydrogenation of alkenes, nitroarenes, ketones, and enamides.
Demonstrated excellent catalyst stability and reusability over multiple reaction cycles.
Showcased chemoselective synthesis of industrially relevant fine chemicals, including biobased cyrene.

Conclusions:

Cellulose-immobilized PdNPs offer a highly efficient, stable, and reusable catalytic system for scalable hydrogenation.
The straightforward preparation method and mild reaction conditions align with green chemistry principles.
This catalyst is suitable for the sustainable synthesis of valuable fine chemicals in flow processes.