modern models for predicting partitioning ... toro_oct_2015_final.pdf · modern models for...
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Modern Models for Predicting Partitioning,
Bioconcentration, and Toxicity of Organic Chemicals
The End of the Age of Octanol
Dominic M. Di ToroEdward C. Davis Professor of
Civil and Environmental Engineering
University of Delaware, Newark, DE
2015 HDC SETAC Fall Workshop
Porewater: The Interactions between Sediment, Biota and Water
D&R Greenway Land Trust
Johnson Education Center
Princeton, NJ 08540 1
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Difficulty
Environmental Engineering Model Parameters
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(1)
(2)
(3)
Difficulty
Environmental Engineering Model Parameters
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Karickhoff, S. W., Brown, D. S., & Scott, T. A. (1979). Wat. Res, 13, 241-248.
KOC = KP / fOC
The Age of OctanolKOC – KOW - Discovered 1979
Log KOC = a0 + a1 Log KOW
KOC
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Nguyen TH, Goss K-U, Ball WP. 2005. Environ Sci Technol 39:913-924.
The Age of Octanol - KOC - 2000’s
a1 = 0.84
a1 = 1.14
a1 = 0.94
a1 = 0.73
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The End of the Age of Octanol
The Age of the Polyparameter LFER Model
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Abraham Parameters QuantifyChemical Interactions
Abraham MH, Chadha HS, Whiting GS, Mitchell RC J. Pharmaceutical Sciences 83(8) 1994 Goss, K., & Schwarzenbach, R. P. (2001). Environ. Sci. Technol., 35(1), 1-9. 7
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Kipka,U & Di Toro, D.M. (2011) Environ Toxicol Chem, 30(9), 20138
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Kipka,U & Di Toro, D.M. (2011) Environ Toxicol Chem, 30(9), 2033 9
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Wei‐Haas, M. L.; Hageman, K. J.; Chin, Y. P., Partitioning of Polybrominated Diphenyl Ethers to Dissolved Organic Matter Isolated from Arctic Surface Waters. ES&T 2014, 48, (9), 4852‐4859. 10
Comparison Kow and ppLFER Models
Burkhard, L. P., ES&T 2000, 34, (22), 4663
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Predictions using ppLFER Model
Kipka, U., Di Toro, D. M. (2011). Environ Toxicol Chem, 30(9), 2013-2022
HMX
RDX
TNT11
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Predictions using EPI Suite Model
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Plant BCF ModelWorm BCF Model
Kuo, D. T. F., & Di Toro, D. M. In preparation 2015
Torralba-Sanchez, T.L. & Di Toro, D. M. PhD Thesis University of Delaware 2015
Earthworm BCF Barley Shoots BCF
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Predictions using ppLFER Model
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Why Use the Abraham Model?
Many Useful Models Exist
Partitioning Environmental Phase/Water
Particulate Organic CarbonDissolved Organic CarbonCoal Tar
Environmental Phase/Air Aerosol Diesel Soot Mineral Surfaces WaterWater Surface Snow Surface
Biological Phases/WaterStorage LipidPhospholipid Membrane Serum AlbuminMuscle Protein
Biological Phases/Blood LungFatKidneyHeartBrain
Toxicity/Aquatic Species Baseline Narcosis Polar Narcosis
Toxicity/Mammals Water-Skin Permeation Eye Irritation Nasal Pungency Resp. Irritation Mice Odor Thresholds
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Endo, S.; Goss, K. U., Environmental Science & Technology 2014, 48, (21), 12477. 15
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Abraham Parameters
Estimates Using Absolv
http://www.acdlabs.com/products/percepta/predictors/absolv/
RDX
TNT
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Experimental and Absolv Solvent-Water Partition Coefficients
Yuzhen Eva Liang University of Delaware PhD Thesis 201618
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Solvent-Water Partition Coefficients
Absolv and COSMO-SAC Based Abraham Parameters
COSM
O‐SAC
Yuzhen Eva Liang University of Delaware PhD Thesis 201619
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Acknowledgements
• UNIVERSITY OF DELAWAREHerbert E. Allen PIDominic M. Di Toro PIStanley T. SandlerOlga DmitrenkoPost-Doctoral Fellows: Dave Kuo; Alauddin AhmedGraduate Students: Rosalina Gonzalez, Andrew Miglino;
Tifany Torralba; Yuzhen Liang
• EDGEWOOD CB CENTER Ronald T. CheckaiRoman Kuperman, Carlton Phillips, Michael SiminiPost-Doctoral Fellow: Morgan Maynard
• BIOTECHNOLOGY RESEARCH INSTITUTE – NRCCJalal HawariGeoffrey SunaharaSabine Dodard
ER-1688 Improving Understanding of the Fate and Transport of Munitions Constituents to Enhance Sustainability of Operational Ranges
ER-1734 Developing Quantum Chemical and Polyparameter Models for Predicting Environmentally Significant Parameters for New Munitions Compounds
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