Alkene Isomerization Using a Solid Acid as Activator and Support for a Homogeneous Catalyst

Author Contact: A.J.Seen@utas.edu.au

Summary

In this laboratory experiment, students explore the use of an immobilized Ni[P(OEt)₃]₄-H₂SO₄ catalyst system to study the isomerization of 1-octene to trans- and cis- 2-octene. Nafion-H⁺ is a solid acid ion exchange polymer that both activates the air-sensitive transition metal catalyst and immobilizes the cationic species that can be characterized by UV-vis spectroscopy within the polymer matrix. The isomerization is performed under nitrogen at room temperature and can be completed in two three- or four-hour lab sessions. The product ratio changes throughout the reaction and can be used to illustrate the equilibrium distribution of kinetic vs. thermodynamically stable products.

Supplemental materials are provided on the J. Chem. Educ. website and include student instructions and procedures for preparation of the catalyst and characterization of the Nafion immobilized species.

Summary prepared May 2005 by Julie A. Haack, Department of Chemistry at the University of Oregon.

Category Descriptors

Chemistry Concepts

• Alkenes
• Catalysis
• Coordination Chemistry
• Equilibrium
• Kinetics
• Solid-Support Reagents

Laboratory Techniques

• Air-Sensitive Compounds
• Assembly of Reaction Apparatus
• Distillation
• Gas-Liquid Chromatography
• UV-Vis Spectroscopy

Green Chemistry Principles

• Design Less Hazardous Chemical Syntheses
• Increase Energy Efficiency
• Minimize the Potential for Accidents
• Prevent Waste
• Use Catalysts
• Use Safer Solvents/Reaction Conditions

Chemistry Subdiscipline

• Inorganic chemistry
• Organic Chemistry

Target Audience

• Colleges/Universities

Source

• Journal Articles