Lubricating and Waxy Esters, V: Synthesis, Crystallization, and Melt and Flow Behaviors of Branched Monoesters Incorporating 9-Decenol and 9-Decenoic Acid

Branched derivatives of waxy monoesters incorporating 9-decenol and 9-decenoic acid were synthesized using epoxidation and ring-opening esterification. The reactions were conducted at two different temperatures and monitored over time. The crystallization, melting, and viscosity of the compounds were all controlled strongly as a function of incremental branching. Isomerism was shown to be critically important: an OH group at the end of the hydrocarbon chain completely suppressed crystallization, whereas its isomer with a terminal acyl chain did not. The structure of the linear monoesters were shown to provide the templates for crystallization, melting, and flow behavior, whereas the branching effect extended but could not erase the effect of the base molecular architecture. These compounds present a large range of properties that are suitable for a variety of applications ranging from waxes to lubricants.