Green Chemistry in the Organic Teaching Laboratory: An Environmentally Benign Synthesis of Adipic Acid

• Published in: Journal of chemical education Vol. 77; no. 12; p. 1627
• Main Authors: Reed, Scott M, Hutchison, James E
• Format: Journal Article
• Language: English
• Published: Easton Division of Chemical Education 01.12.2000; American Chemical Society
• Subjects: Adipic acid; Chemical reactions; Chemicals; Chemistry; Classrooms; Cyclohexene; Environmental protection; Experiments; Green chemistry; Inhalants; Laboratory Experiments; Lecture Method; Organic chemistry; Oxidation; Reaction Time; Recycling; Research Methodology; Student Evaluation; Teaching Methods; Oregon; United States > US; Catalysis; Organic Chemistry
• ISSN: 0021-9584; 1938-1328
• DOI: 10.1021/ed077p1627

Environmentally benign ("green") chemical techniques are growing in importance in academic and industrial research laboratories. Such chemistry has been slow to appear in teaching laboratories, owing in part to a lack of published material on this subject. Recent developments in green synthesis provide opportunities to introduce this material in teaching laboratories. We present a synthesis of adipic acid that utilizes green reagents (hydrogen peroxide as the oxidant), solvents (water), and methods (phase-transfer catalysis, catalyst recycling). The synthesis works well and provides an excellent forum for emphasizing green chemical concepts while teaching laboratory skills. It demonstrates reuse of a product, synthesis using a nonhazardous solvent, elimination of deleterious by-products, and use of a recyclable catalyst. It can be carried out on either the macroscale or microscale and generates little waste if the catalyst solution is recycled. This experiment fits well in a sophomore organic sequence; it covers the topics of oxidation, phase-transfer catalysis, and the technique of recrystallization, reinforces lecture topics such as alkene synthesis and reactivity, and provides an opportunity to introduce polymer chemistry.