Evaluating Sustainability: Soap versus Biodiesel Production from Plant Oils

Herein we describe a series of experiments for the undergraduate organic laboratory curriculum in which various plant oils (soybean, rapeseed, and olive) are subjected to saponification and transesterification reactions to create a set of compounds that can function as soaps or as fuels. The experiments introduce students to and asks them to critically evaluate concepts of sustainability and green chemistry, microwave versus conventional heating, and their understanding of chirality prochirality, and stereochemistry. Unexpectedly, because of the comparison between soap and biodiesel production, the experiment also revealed misunderstandings about catalysis.