Environmental modelling of hexamethoxymethylmelamine, its transformation products, and precursor compounds: An emerging family of contaminants from tire wear

Hexamethoxymethylmelamine (HMMM) is a polymer crosslinking agent used commercially to manufacture tires. HMMM is a ubiquitous contaminant in urban surface waters due to its presence in tire-wear particles and its tendency to be transported into receiving waters during rain events through road runoff. It has recently been determined that this chemical readily transforms into numerous other compounds, several of which have also been detected in the aquatic environment. However, there is limited knowledge about the fate and distribution of HMMM and its likely transformation products and precursor compounds. COSMO-RS solvation theory was used to estimate the physico-chemical properties of HMMM and 24 related derivatives, including their aqueous solubility, various partitioning properties, vapour pressure, and melting point. Using these properties as inputs to the Equilibrium Criterion (EQC) fugacity-based multimedia model, three different emission scenarios were modeled. Overall, these compounds were predicted to readily partition into aqueous media, with distributions in water increasing with the loss of methoxymethyl groups. In addition, the persistence of the transformation products of HMMM was predicted to decline with the extent of these transformations. The EQC model predictions indicate that these compounds are subject to overland transport into surface waters. This study provides insights into the fate and behaviour of HMMM and its transformation compounds and contributes to the growing literature on the hazards of organic chemicals derived from tire wear. [Display omitted] •Properties of hexamethoxymethylmelamine (HMMM) and its derivatives are estimated.•Property trends amongst the transformation and precursor compounds are discussed.•The environmental fate of each chemical is predicted using the EQC model.•Compounds are predicted to partition into water upon increased transformation.