Diphenyl disulfide is a common agent used in the devulcanization of sulfur-vulcanized goods. Its activity has been tested both in real rubber samples and in model molecules but, to the best of our knowledge, always under normal heating conditions. Moreover, there is a lack of information about how the vulcanizing potential of the molecule can affect the devulcanization yield. In this study, the diphenyl disulfide behavior has been studied in model compound vulcanization, with squalene used as a model molecule of natural rubber. Microwaves have been used as a heating source, and the vulcanization/devulcanization behavior of the molecules has been characterized. The results have shown that it is possible to tailor the diphenyl disulfide activity by controlling the reaction temperature and also through microwave power control.