Contact Information

Author
  • James E. Hutchison
  • Professor
  • Chemistry
  • Univ. of Oregon
  • Eugene, OR 97403
Email
Phone
(541) 346 - 4228
Website

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.

J. Chem. Educ. (Abstract only)

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