Halogenated Aromatic Hydrocarbons.ppt

Halogenated Aromatic Hydrocarbons PCBs (polychlorinated biphenyls) , PCDDs (dioxin) Introduction Important because provides a classic example of chemicals developed and used with no thought to environmental consequences For first 40 years of manufacture many were thought to be biologically inactive! A large problem because of wide-spread use and persistence Dioxin – discharged from paper mills, coal fired utilities, metal smelting, diesel trucks, land application of sewage sludge, burning treated wood, trash burn barrels PCBs - used in transformers, capacitors, hydraulic fluids Natural follow-up topic to pesticides because PCBs have toxicological properties that are similar to pesticides (although never designed to be released into the environment) Chemistry Very complex because have multiple congeners (different attachment points to base molecules) ? 209 different PCBs Most environmentally important are PCBs (polychlorinated biphenyls) and PCDDs (polychlorinated dibenzo-p-dioxin) Formed by covalent bonding of halogens (Cl, Br, F, etc) to 6 carbon ring structures (benzene, biphenyls (two fused benzenes) Easy (cheap) to form bonds, hard to break bonds Halogenation changes properties of parent structure both above useful for cheaply making lots of compounds that do not break down. Chemistry (con’t) Halogenation - location/type of halogen changes properties a. Increases MW – increases specific gravity, melting/boiling point – many industrial applications. b. Increases stability (C - halogen stronger than C - H) = persistent Lipophilicity - tend to accumulate in fatty tissue Note: high persistence + high lipophilicity = high bioconcentration potential Amounts and Uses Amounts - 1.3 billion lbs produced between 1930 and 1976 – 1.25 billion in U.S. by Monsanto Uses - heat exchange and hydraulic fluids, lubricants, dielectric fluids in transformers/capacitors, plasticizers Widely used, especially industrial countries Partially banned in US in ‘76, full