Automobile tires require functional rubber additives including curing agents and antioxidants, which are potentially environmentally available from tire and road wear particles (TRWP) deposited in soil and sediment. A novel methodology was employed to evaluate the environmental fate of three commonly-used tire chemicals (N-cyclohexylbenzothiazole-2-sulfenamide (CBS), N-(1,3-dimethylbutyl)-N′-phenyl-1,4-phenylenediamine (6-PPD) and 1,3-diphenylguanidine (DPG)), using a road simulator, an artificial weathering chamber, column leaching tests, and OECD 308 sediment/water incubator studies. Environmental release factors were quantified for curing (f_C), tire wear (f_W), terrestrial weathering (f_S), leaching from TRWP (f_L), and environmental availability from TRWP (f_A) by liquid chromatography–tandem mass spectroscopy (LC/MS/MS) analyses. Cumulative fractions representing total environmental availability (F_T) and release to water (F_R) were calculated for the tire chemicals and 13 transformation products. F_T for CBS, DPG and 6-PPD inclusive of transformation products for an accelerated terrestrial aging time in soil of 0.1 years was 0.08, 0.1, and 0.06, respectively (equivalent to 6 to 10% of formulated mass). In contrast, a wider range of 5.5 × 10^− 4 (6-PPD) to 0.06 (CBS) was observed for F_R at an accelerated age of 0.1 years, reflecting the importance of hydrophobicity and solubility for determining the release to the water phase. Significant differences (p < 0.05) in the weathering factor, f_S, were observed when chemicals were categorized by boiling point or hydrolysis rate constant. A significant difference in the leaching factor, f_L, and environmental availability factor, f_A, was also observed when chemicals were categorized by log K_ow. Our methodology should be useful for lifecycle analysis of other functional polymer chemicals.