Manmade Organic Compounds in the Surface Waters of the United States-A Review of Current Understanding

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Manmade Organic Compounds in the Surface Waters of the United States-A Review of Current Understanding U.S. GEOLOGICAL SURVEY CIRCULAR 1007 Manmade Organic Compounds in the Surface Waters of the United States-A Review of Current Understanding Manmade Organic Compounds in the Surface Waters of the United States-A Review of Current Understanding By JAMES A. SMITH, PATRICK j. WITKOWSKI and THOMAS V. FUSILLO U.S. GEOLOGICAL SURVEY CIRCULAR 1007 U.S. DEPARTMENT OF THE INTERIOR BRUCE BABBITT, Secretary U.S. GEOLOGICAL SURVEY GORDON P. EATON, Director Any use of trade, product, or firm names in this publication is for descriptive purposes only and does not imply endorsement by the U.S. Government First printing 1988 Second printing 1993 Third printing 1996 UNITED STATES GOVERNMENT PRINTING OFFICE:1988 Free on application to the Books and Open-File Reports Section, U.S. Geological Survey, Federal Center, Box 25425, Denver, CO 80225 Ubrary of Congress Cataloging In Publication Data Smith, James A. (James Albert) Manmade organic compounds in the surface waters of the United States. (U.S. Geological Survey circular ; 1007) Bibliography: p; Supt. of Docs. no.: I 19.4/2:1007. 1. Organic water pollutants-United States. 2. Organic compounds. I. Witkowski, P.J. (Patrick J.) II. Fusillo, Thomas V. Ill. Title. IV. Series. T0427.07S55 1988 363.7'394 87-600258 CONTENTS Abstract 1 Introduction 1 Background 1 Purpose and scope 2 Processes affecting the fate and distribution of organic compounds 2 Sorption 2 Definitions 2 Adsorption and partitioning 3 Sorption of nonionic organic compounds 3 Importance of particulate organic matter 6 Importance of dissolved organic matter 8 Sorption of ionic organic compounds 8 Organic acids 9 Organic bases 9 Bioaccumulation 11 Importance of biological lipid reservoirs 11 Biomagnification 14 Transformation processes 1S Photolysis 16 Hydrolysis 18 Biodegradation 19 Volatilization 21 Polychlorinated biphenyls and chlorinated insecticides · 25 Uses, production, properties, and regulatory limits 25 Environmental fate 27 Environmental distribution 32 Carbamate and organophosphorus insecticides 36 Uses, production, properties, and regulatory limits 36 Environmental fate 37 Environmental distribution 39 Herbicides 39 Uses, production, properties, and regulatory limits 39 Environmental fate 40 Environmental distribution 43 Phenols 44 Uses, production, properties, and regulatory limits 44 Environmental fate 45 Environmental distribution 49 Halogenated aliphatic and monocyclic aromatic hydrocarbons 50 Uses, production, and properties 50 Environmental fate 52 Environmental distribution 55 Phthalate esters 56 Uses, production, and properties 56 Environmental fate 57 Environmental distribution 59 Contents Ill Polychlorinated dibenzo-p-dioxins 60 Uses, production, and properties 60 Environmental fate 62 Environmental distribution 63 Polycyclic aromatic hydrocarbons 64 Uses, production, and properties 64 Environmental fate 66 Environmental distribution 70 Summary 73 Selected references 74 FIGURES 1-10. Plots showing: 1. Correlation of octanol-water partition coefficient with water solubility for selected aromatic liquids and solids at 25 oc 4 2. Soil-water equilibrium isotherms of some neutral organic compounds at 20 oc 4 3. Typical soil-water equilibrium isotherms for 1,3-dichlorobenzene and 1 ,2,4-trichlorobenzene as single solutes and as binary solutes on a Woodburn silt loam soil at 20 oc 5 4. Soil organics-water sorption coefficients plotted as a function of the aqueous solubilities of selected neutral organic compounds 5 5. Sorption coefficient normalized for organic-carbon content as a function of compound water solubility and octanol-water partition coefficient 7 6. Adsorption isotherms of paraquat in soils 10. 7. Correlation of bioconcentration factor versus octanol-water partition coefficient showing the correlations of Veith and others (1979), Neely and others (1974), and Mackay (1982a) 12 8. Relation between log water solubility of pesticides and log bioconcentration factor for Triaenodes tardus egg masses 13 9. Correlation of log bioconcentration factor on the basis of fish lipid content with log triolein-water partition coefficient for a variety of nonionic organic compounds 14 10. Relation between microbial specific growth rate and substrate concentration 20 11. Structural diagrams of selected chlorinated insecticides and a polychlorinated biphenyl 25 12. Plot showing relation of summer mean polychlorinated biphenyl (PCB) concentrations in water and lipid-bas~ PCB concentrations in fiiiets of whole yearling pumpkinseed collected September 1977-83 at Stillwater, N.Y 35 13. Frequency of detection of organochlorine insecticides in water and bed-material samples from stations in the U.S. Geological Survey-U.S. Environmental Protection Agency Pesticide Monitoring Network, 1975-80 35 14. Structural diagrams of selected carbamate and organophosphorus insecticides 36 IV Contents 15, 16. Plots showing: 14 15. Cumulative C02 (percentage of added ring-labeled 14C-insecticide) emlved in a soil planted to rice under flooded and nonflooded conditions 38 16. Trends in national use of herbicides and insecticides on major crops, 1964-82 40 17, 18. Structural diagrams of: 17. Selected herbicides 40 18. Selected phenolic compounds 44 19. Structural diagrams showing degradation pathway of pentachlorophenol in soils 48 20. Structural diagrams of selected halogenated aliphatic and monocyclic aromatic hydrocarbons 51 21. Graph of predicted volatilization rates of methylene chloride and dichlorobenzene in the Rio Grande River, N.Mex. 55 22. Structural diagrams of some common phthalate esters 57 23, 24. Structural diagrams showing: 23. Degradation of di-n-butyl phthalate, mono-n-butyl phthalate, and phthalic acid by different microorganisms: organisms isolated with di-n-butyl phthalate as carbon source for enrichment, stock cultures, and bacteria isolated from phthalic acid enrichment medium 59 24. Formation of 2,3,7,8-tetrachlorodibenzo-p-dioxin as a byproduct in the synthesis of 2,4,5-trichlorophenoxyacetic acid 60 25. Structural diagrams of selected polycyclic aromatic hydrocarbons 66 26. Structural diagrams showing proposed degradation pathway of phenanthrene by soil pseudomonads 70 TABLES 1. Contrasting characteristics of adsorption and partition processes 3 2. Selected anionic and cationic organic compounds of environmental significance 9 3. Approximate molecular composition of some Aroclor mixtures 26 4. Some uses of polychlorinated biphenyls suggested by the manufacturer 27 5. Detection limits, water-quality criteria, and use data for selected organo­ chlorine insecticides 28 6. Experimentally determined octanol-water partition coefficients, solubilities, and vapor pressures of selected polychlorinated biphenyls and chlorinated insecti­ cides at room temperature 29 7. Experimentally determined sorption coefficients for some polychlorinated biphenyls and organochlorine insecticides 30 8. Experimentally determined bioconcentration factors for some polychlorinated biphenyls and organochlorine insecticides 31 9. Means and ranges of detectable sediment residues of polychlorinated biphenyls and organochlorine insecticides 33 10. Detectable residues of polychlorinated biphenyls and organochlorine insecti­ cides in biota 34 11. Experimentally determined octanol-water partition coefficients, solubilities, and vapor pressures of selected organophosphorus and carbamate insecticides at room temperature 36 Contents V 12. Detection limits, water-quality criteria, and use data for selected organophosphorus insecticides 37 13. Characteristics of selected carbamate insecticides 38 14. Approximate persistence of pesticides in soils 38 15. Detection limits, water-quality criteria, and use data for some common herbicides 40 16. List of and magnitude of application of herbicides in 11 agricultural water­ sheds in Ontario, 1975 41 17. Experimentally determined aqueous solubilities and vapor pressures of selected herbicides at room temperature 41 18. Structural groupings of selected herbicides 41 19. Herbicide residues in North American surface waters 43 20. World production of phenol in 1978 45 21. Experimentally determined physicochemical properties of selected phenolic compounds at room temperature 46 22. Phenol bacteria present during the winter and (or) summer season in St. Lawrence River water and maximum phenol levels that could be tolerated 47 23. Time required for bacteria to use 95 percent of parent substrate 48 24. Photolysis of phenols and their degradation products 48 25. Experimentally determined sorption coefficients of nonionized chlorinated phenols for different natural sorbents 49 26. Concentration of phenol and some of its chlorinated derivatives in municipal and industrial wastewater 50 27. U.S. production of selected halogenated aliphatic and monocyclic aromatic hydrocarbons 51 28. Uses of selected halogenated aliphatic and monocyclic aromatic hydro­ carbons 52 29. Experimentally determined octanol-water partition coefficients, solubilities, and vapor pressures of selected halogenated aliphatic and monocyclic aromatic hydrocarbons at room temperature 53 30. Evaporation times for 50 and 90 percent removal of chlorinated aliphatic hydrocarbons (1 milligram per liter) at 25 oc, 200 revolutions per minute of stirring, and a depth of 6.5 centimeters 54 31. Ratios of overall transfer coefficients for selected aliphatic and monocyclic aromatic hydrocarbons to overall transfer coefficients for oxygen 54 32. Uses of phthalate esters in the United States 57 33. Solubilities and vapor pressures of selected phthalate esters 58 34. Selected
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