Mechanisms and Kinetics Studies of Butylated Hydroxytoluene Degradation to Isobutene

2,6-Di-tert-butyl-hydroxytotulene (BHT) is a widely used antioxidant in various fields. In this study, we explored comprehensively the mechanisms and kinetics of BHT degradation to produce isobutene using the density functional theory method. Furthermore, the intrinsic chemical reactivity of BHT was investigated using the electrostatic potential, average local ionization energy, and Fukui function, and the most likely reaction site with OH radical was predicted. Two initiation pathways of BHT with OH radicals were reported. The OH addition pathways at the C2 site of BHT was found more likely to occur than the pathways of H abstracts from the t-butyl group due to the lower energy barrier. Rate constants of two initiation pathways were calculated by transition state theory, and they were promoted by the temperature rise. Mayer bond order and localized molecular orbitals analysis were conducted to reveal the variation of the chemical bonds in the reaction process. The tertiary butyl radical that had been generated in the OH-addition reaction was more likely to generate isobutene with the participation of oxygen. Overall, this research could help to reveal the transformation mechanism of isobutene produced by BHT degradation.