Scent Transmutation: A New Way To Teach on Chemical Equilibrium, Distillation, and Dynamic Combinatorial Chemistry

Esters are volatile and pleasantly smelling compounds, commonly used as food additives. Using Ti­(OBu)4-catalyzed acyl exchange, we demonstrate a scent transmutation experiment, in which two fragrant esters swap their acyl and alkoxy substituents and are, during the course of a reactive distillation, quantitatively converted into two different esters with distinct fragrance properties. We view this simple and appealing experiment as highly suitable for instructional use, since it can be used to teach the concepts of chemical equilibrium, distillation, transesterification, dynamic combinatorial chemistry, and the industrially relevant process of reactive distillation.