Contact Information
Green Chemistry in the Organic Teaching Laboratory: An Environmentally Benign Synthesis of Adipic Acid
Author Contact: hutch@uoregon.edu
Summary
Industrial production of adipic acid involves the oxidation of cyclohexanol, cyclohexanone, or both by nitric acid. An inevitable byproduct of this reaction is nitrous oxide, implicated in the process of global warming and ozone depletion. In this experiment, students synthesize adipic acid using sodium tungstate-catalyzed oxidation of cyclohexene by hydrogen peroxide in water.
This method replaces a hazardous oxidizing agent with an environmentally benign one, uses water as the solvent, and teaches the benefits of using a recyclable catalyst. The experiment introduces important laboratory techniques including recrystallization and phase-transfer catalysis while providing an opportunity to introduce polymer chemistry.
Supplemental materials are provided on the J. Chem. Educ. website and include laboratory procedures and a student report template.
Summary prepared May 2005 by Julie A. Haack, Department of Chemistry at the University of Oregon.
Source
Reed, S. M.; Hutchison, J. E. J. Chem. Educ., Print 2002, 77, pp 1627-1629.
Category Descriptors
- Chemistry Concepts
- Alkenes
- Catalysis
- Oxidation/Reduction Chemistry
- Laboratory Techniques
- Assembly of Reaction Apparatus
- IR Spectroscopy
- Melting Points and Melting Ranges
- NMR Spectroscopy
- Recrystallization
- Green Chemistry Principles
- Design Less Hazardous Chemical Syntheses
- Maximize Atom Economy
- Prevent Waste
- Use Catalysts
- Use Safer Solvents/Reaction Conditions
- Chemistry Subdiscipline
- Environmental Chemistry
- Organic Chemistry
- Polymer Chemistry
- Target Audience
- Colleges/Universities
- Source
- Journal Articles
