1. Organic Chemicals and Water

2. Synthetic Organic Chemicals Dioxins Pesticides PCBs Cleaning agents Chlordane Dioxin PBDE DDT Organochlorines Flame Retardants Principally Carbon, Hydrogen and Oxygen

3. Viktor Yushchenko Ukrainian President Potential Toxicity 6,000 times the usual concentration in his body July November the second highest dioxin level ever measured in a human 2004

4. Water Solubility Organochlorines as well as many other synthetic organic compounds are poorly soluble in water

5. NaClNa + + Cl - Na +

6. Dioxin

7. PCB 10-31 µg/L (50% Cl ) 0.2 µg/L Sodium Chloride350 g/L Potassium Chloride280 g/L Ionic compounds are about 1 billion times more water soluble than neutral organics

8. Organic Solvents Improving Solubility Hexane Structural/chemical similarity between the chemical and the solvent. Soap/detergents

9. Structural/chemical similarity between the chemical and the solvent. Lipids and Solubility

10. Solubility A chemical’s solubility in lipids is inversely proportional to its solubility in water. Carbon/hydrogen Lipid (Carbon/hydrogen) water

11. Seawater Arctic cod muscle Narwhal blubber 14 - 46 ppb 0.0003 ppb 2440 - 9160 ppb Toxaphene Biomagnification BAF = 8 million

12. What’s been done?

13. PCBs used extensively in electrical equipment, especially transformers Electrical equipment plasticizers in paints, plastics and rubber products pigments, dyes and carbonless copy paper Solubility: 10-31 µg/L PCBs were “banned” in 1979 PCBs, valued for chemical stability and fire resistance, were manufactured and processed primarily for use as insulating fluids and coolants in electrical equipment and machinery from 1929-1977.

14. [EPA press release - April 19, 1979] The Environmental Protection Agency today issued final regulations banning the manufacture of polychlorinated biphenyls (PCBs) and phasing out most PCB uses. PCBs are toxic and persistent chemicals primarily used as insulating fluids in heavy-duty electrical equipment in power plants, industries, and large buildings across the country. The EPA rules will gradually end many industrial uses of PCBs over the next five years, but will allow their continued use in existing enclosed electrical equipment under carefully controlled conditions. EPA estimates that 150 million pounds of PCBs are dispersed throughout the environment, including air and water supplies; an additional 290 million pounds are located in landfills in this country

15. Spokane River Nov. 2002

16. Lake Michigan µ g PCB/Kg sediment EPA, 2004 N Concentration PCBs

17. Lake Erie Sediments PCBs After 25 years, PCBs continue to persist in the Environment EPA, 2004

18. Poor water solubility High solubility in Lipids and Organic Solvents Potentially long half lives Persistent Organic Pollutants PCB DDTDioxin

19. Half Life

20. ½ Life The time it takes for a chemical to degrade To ½ of its original concentration. Ci ½ Ci time t 1/2

21. DDT 28 days 15 – 20 years PCBs 1 month 2-6 years > 60 years up to 150 years ½ Life and Organochlorines Dioxin 1 - 30 years (7 years in humans)

22. Water Column Sediments (longer half-life) Environmental Persistence Solubility of < 0.2 μg/L Short Half life

23. Environmental Persistence, Half Life and Solubility

24. An Important Organic Solvent:Octanol C 8 H 18 O Neutral organic chemicals are soluble in organic solvents

25. The Octanol-Water Partitioning coefficient Octanol and water are immiscible Density: 0.824 g/cm3 octanol water C 8 H 18 O

26. Octanol (Carbon/Hydrogen) water Carbon/hydrogen Partitioning C 10 H 20

27. 1 L Octanol 1L Water Add 10 mg chemical separate chemical Analyze the water phase for the chemical. Difference between initial amount and amount in water = amount in octanol The ratio between the two yields the K ow

28. Add 10 mg chemical separate chemical 0.01 mg L 9.99 mg L Water phase octanol phase Kow = 9.99 mg L 0.01 mg L = 999 1 L Octanol 1L Waterl

29. K ow of some Organochlorine Compounds PCBs 2,000,000 DDT 4,000,000 Dieldrin 158,000 Toxaphene316,000

30. Water Column Sediments (Carbon) Environmental Persistence Solubility of < 0.2 μg/L Short Half life