Persistent organic pollutants are a well-known threat to the environment. Substances such as polycyclic aromatic hydrocarbons and chlorinated organic compounds in contaminated soil and groundwater can have severe and long-lasting effects on health in animals and humans. There is an urgent need for the development of safe technologies for their effective removal. Originally developed for mineral processing, mechanical treatment by ball milling is an extremely versatile technique for the degradation of toxic compounds. Reactive milling can rapidly destroy organic compounds without producing hazardous wastes. Complete breakdown of the organic molecules is achieved after relatively short milling times. Successful tests were conducted on polychlorobiphenyls (PCBs), DDT, DDD, DDE, Dieldrin and hexachlorobenzene with a conversion yield in the of greater than 99% (Hall et al., 1996; Monagheddu et al., 2000; Zhang et al., 2001; Zhang et al., 2002; Tanaka and Zhang, 2003; Pizzigallo et al., 2004; Nomura et al., 2005; Bellingham, 2006).In this study reactive ball milling was used to investigate the destruction of two classes of persistent organic pollutants environmental contaminants. The compounds studied are either known environmental pollutants or simple analogues. These were chosen as being representative of pollutants to investigate the pathway using ball milling destruction and in most cases were relatively small molecules so that the intermediates could be more easily identified. The first class of compounds was polycyclic aromatic compounds. Some smaller members of this class such as naphthalene, anthracene were investigated. The second class of compounds were some analogues of environmentally hazardous hydroxylated and halogenated compounds such as chloronaphthalene, bromonaphthalene, 1- naphthol, 2-naphthol and pentachlorophenol under reactive milling using GCMS analysis of the degradation pathway. Destruction efficiencies greater than 99% have been achieved for a number of organic compounds. Several different intermediates have been identified during the milling degradation. There was also some evidence from this study that halogens could be transferred between compounds during milling. The final products of the milling destruction of these compounds are an amorphous carbon residue and inorganic chloride or bromides. It was proposed that large amounts of halogens could be found however the results showed that small amounts detected. At early stages of milling a number of intermediate breakdown products were detected which were destroyed on extended milling. The core objective of this research was to clarify the reaction mechanisms pathways used of more complex polycyclic aromatic hydrocarbons and aromatic organ halogen compounds. This study is a part of a long-term research project on the destruction of toxic organic compounds by reactive milling.