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And Octanol-Water Partition Coefficient (Kow) Data for Hydrophobic Organic Compounds: DDT and DDE As a Case Study U.S. Department of the Interior U.S. Geological Survey The Search for Reliable Aqueous Solubility (Sw) and Octanol-Water Partition Coefficient (Kow) Data for Hydrophobic Organic Compounds: DDT and DDE as a Case Study By James Pontolillo and Robert P. Eganhouse U.S. Geological Survey Water-Resources Investigations Report 01-4201 Reston, Virginia 2001 U.S. DEPARTMENT OF THE INTERIOR BRUCE BABBITT, Secretary U.S. GEOLOGICAL SURVEY Charles G. Groat, Director The use of firm, trade, and brand names in this report is for identification purposes only and does not constitute endorsement by the U.S. Government. For additional information write to: Copies of this report can be purchased from: Branch Chief U.S. Geological Survey Branch of Regional Research Branch of Information Services Eastern Region Box 25286, Federal Center U.S. Geological Survey Denver, CO 80225-0286 12201 Sunrise Valley Drive Telephone: 1-888-ASK-USGS Mail Stop 432 Reston, VA 20192 This report can be accessed at: http://pubs.water.usgs.gov/wri01-4201/ CONTENTS Abstract............................................................................................................................................................................... 1 Introduction ........................................................................................................................................................................ 2 Background............................................................................................................................................................... 2 Acknowledgments .................................................................................................................................................... 3 Methodology....................................................................................................................................................................... 3 Literature Errors ................................................................................................................................................................. 4 Types......................................................................................................................................................................... 4 Extent........................................................................................................................................................................ 6 Effects....................................................................................................................................................................... 9 Published Original Data...................................................................................................................................................... 9 Data Quality.............................................................................................................................................................. 18 Assessment of DDT/DDE Sw and Kow Original Data Sources................................................................................ 19 Effect of Methodology.............................................................................................................................................. 20 Summary and Conclusions ................................................................................................................................................. 23 References Cited................................................................................................................................................................. 24 Appendix A: Data of Uncertain Origin .............................................................................................................................. 36 Appendix B: Assessment of DDT/DDE Sw and Kow Original Data Sources using a Criteria-based Rating System ..................................................................................................................................... 41 Figures 1. Reference tree showing original O’Brien (80) publication and secondary, tertiary, and higher references as an example of multi-level referencing ....................................................................................................................... 5 2. Plots of percent of citations in compilation articles and databases that are original data sources, multi-level references, citation errors or data errors by date of publication/acquisition ...................................... 7 3. Plots of citation categories for four compilation articles with Sw (unfilled bars) and Kow (filled bars) data ....... 8 4. Plots of aqueous solubility (Sw) and log octanol-water partition coefficient (log Kow) data for DDT and DDE in references reported by Mackay and others (1).................................................................................. 10 5. DDT and DDE Sw and Kow original data generation plots as a function of publication date along with a timeline of important historical events.................................................................................................................. 12 6. Original Sw data for DDT and DDE plotted as a function of publication date ..................................................... 16 7. Original log Kow data for DDT and DDE plotted as a function of publication date............................................. 17 8. Original DDT log Kow data plotted according to method of determination/estimation by date of publication and irrespective of date of publication .................................................................................................................. 22 B1. Sw rating scheme (after Heller and others, 1994) ................................................................................................. 43 B2. Log Kow rating scheme (after Heller and others, 1994; Kollig, 1988) ................................................................. 44 Contents III Tables 1. Numbers, types and sizes of erroneous data strings reported in compilation of Mackay and others (1) .............. 11 2. Contribution of erroneous data to overall database in compilation of Mackay and others (1).............................. 11 3. Statistical comparison of Sw and log Kow data reported in compilation of Mackay and others (1)...................... 12 4. Published original DDT Sw and log Kow data ....................................................................................................... 13 5. Published original DDE Sw and log Kow data ....................................................................................................... 15 6. Basic statistics for uncensored original Sw and Kow DDT/DDE data ................................................................... 18 7. ARS/NIST ratings system (after Heller and others, 178) ...................................................................................... 19 8. DDT/DDE Sw and log Kow original data sources that received the highest rating (rating=1) using criteria-based data source quality evaluation schemes ......................................................................................... 20 9. Statistical information on uncensored original DDT/DDE Sw and log Kow data by method of determination .... 21 A1. DDT Sw and log Kow data of uncertain origin ...................................................................................................... 36 A2. DDE Sw and log Kow data of uncertain origin ...................................................................................................... 38 B1. ARS/NIST ratings system (after Heller and others, 1994).................................................................................... 42 B2. DDT Sw and log Kow original data source ratings ................................................................................................ 45 B3. DDE Sw and log Kow original data source ratings ................................................................................................ 47 Units and Acronyms g/L grams per liter mg/L milligrams per liter mol/L moles per liter oC temperature in degrees Celsius ARS U.S. Agricultural Research Service ASTM American Society for Testing and Materials BAF bioaccumulation factor BCF bioconcentration factor CAS Chemical Abstracts Service CASSI Chemical Abstracts Search Service Index DDE dichlorodipheyldichloroethylene, (ClC6H4)2C=CC12 DDTdichlorodiphenyltrichloroethane, (ClC6H4)2CHCC13 EPA U.S. Environmental Protection Agency IUPAC International Union of Pure and Applied Chemistry Koc organic carbon-normalized partition coefficient Kow octanol-water partition coefficient log Kow base-10 logarithm of octanol-water partition coefficient NISTNational Institute of Standards and Testing OECD Organisation for Economic Co-operation and Development POPs persistent organic pollutants p,p’-DDE primary metabolite of p,p’-DDT p,p’-DDTdominant isomer in technical DDT PPR property-property relation QSAR quantitative structure-activity relation Soct solubility in n-octanol SPARC SPARC Performs Automated Reasoning in Chemisty SPR structure-property relation Sw aqueous solubility RP-HPLC reversed phase-high performance liquid chromatography IV Contents The Search for Reliable Aqueous Solubility (Sw) and Octanol- Water Partition Coefficient (Kow) Data for Hydrophobic Organic Compounds: DDT and DDE as a Case Study by James Pontolillo and Robert P. Eganhouse ABSTRACT tion of the methods of determination used by the authors.
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