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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

(1)

(2)

(3)

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

Kipka,U & Di Toro, D.M. (2011) Environ Toxicol Chem, 30(9), 20138

Kipka,U & Di Toro, D.M. (2011) Environ Toxicol Chem, 30(9), 2033 9

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

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

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

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

Solvent-Water Partition Coefficients

Absolv and COSMO-SAC Based Abraham Parameters

COSM

O‐SAC

Yuzhen Eva Liang University of Delaware PhD Thesis 201619

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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