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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.
Reed, S. M.; Hutchison, J. E. J. Chem. Educ., Print 2002, 77, pp 1627-1629.