The temperature dependency of the polymerization of 2-phenyl-2-oxazoline was investigated utilizing a commercially available automated synthesizer equipped with individually heatable reactors. Kinetic investigations resulted in an optimal polymerization temperature and activation energy determination for the polymerizations initiated with methyl tosylate. Moreover, the in situ generation of benzyl iodide (more reactive initiator) from benzyl chloride and sodium iodide is described, whereby solid sodium iodide was automatically dosed into the reactors.