Ion-exchange affinity of organic cations to natural organic matter: Influence of amine type and nonionic interactions at two different pHs

Environmental Science and Technology

Volumn 47, Issue 2, 2013, Pages 798-806

  Droge, Steven T J ^a   Goss, Kai Uwe ^a,b  

^a HELMHOLTZ CENTRE FOR ENVIRONMENTAL RESEARCH UFZ   (Germany)

^b MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL CHAIN LENGTHS; AQUEOUS MEDIUM; AROMATIC RINGS; CATIONIC SPECIES; CHARGED GROUPS; CHEMICAL MOIETIES; EFFECT OF PH; EMPIRICAL CORRECTION FACTOR; EQUAL SIZES; FLOWTHROUGH; HYDROXYL GROUPS; IONIC SPECIES; MOLECULAR FORMULA; NATURAL ORGANIC MATTERS; NEUTRAL COMPOUNDS; NEUTRAL SPECIES; NONIONIC INTERACTIONS; ORGANIC CATIONS; PARTITION COEFFICIENT; POLAR FUNCTIONAL GROUPS; SOIL ORGANIC MATTERS; SORPTION AFFINITY; SORPTION COEFFICIENTS; SORPTION DATA; SORPTION MODELS; STANDARD ERRORS; WEAK BASIS;

AMMONIUM COMPOUNDS; BIOLOGICAL MATERIALS; ION EXCHANGE; ORGANIC COMPOUNDS; POSITIVE IONS;

SORPTION;

AMINE; CATION; FUNCTIONAL GROUP; HYDROXYL GROUP; SOIL ORGANIC MATTER;

AQUEOUS SOLUTION; CATION; CORRECTION; EMPIRICAL ANALYSIS; ION EXCHANGE; ORGANIC MATTER; PARTITION COEFFICIENT; PH; SOIL ORGANIC MATTER; SORPTION;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; ION EXCHANGE; PH;

ADSORPTION; AMINES; CATIONS; HYDROGEN-ION CONCENTRATION; ION EXCHANGE; MODELS, CHEMICAL; ORGANIC CHEMICALS; QUATERNARY AMMONIUM COMPOUNDS; SOIL; SOIL POLLUTANTS;

EID: 84872579635     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es3033499     Document Type: Article

References (48)

1. Alder, A. C.; Schaffner, C.; Majewsky, M.; Klasmeier, J.; Fenner, K. Fate of [beta]-blocker human pharmaceuticals in surface water: Comparison of measured and simulated concentrations in the Glatt Valley Watershed, Switzerland Water Res. 2010, 44 (3) 936-948
2. Zuccato, E.; Castiglioni, S.; Bagnati, R.; Chiabrando, C.; Grassi, P.; Fanelli, R. Illicit drugs, a novel group of environmental contaminants Water Res. 2008, 42 (4-5) 961-968
3. Martínez-Carballo, E.; Sitka, A.; González-Barreiro, C.; Kreuzinger, N.; Fürhacker, M.; Scharf, S.; Gans, O. Determination of selected quaternary ammonium compounds by liquid chromatography with mass spectrometry. Part I. Application to surface, waste and indirect discharge water samples in Austria Environ. Pollut. 2007, 145 (2) 489-496
4. Martínez-Carballo, E.; González-Barreiro, C.; Sitka, A.; Kreuzinger, N.; Scharf, S.; Gans, O. Determination of selected quaternary ammonium compounds by liquid chromatography with mass spectrometry. Part II. Application to sediment and sludge samples in Austria Environ. Pollut. 2007, 146 (2) 543-547
5. Li, X.; Brownawell, B. J. Quaternary ammonium compounds in urban estuarine sediment environments-A class of contaminants in need of increased attention? Environ. Sci. Technol. 2010, 44 (19) 7561-7568
6. Ishiguro, M.; Tan, W.; Koopal, L. K. Binding of cationic surfactants to humic substances Colloids Surf. A 2007, 306 (1-3 SPEC. ISS.) 29-39
7. Durjava, M. K.; ter Laak, T. L.; Hermens, J. L. M.; Struijs, J. Distribution of PAHs and PCBs to dissolved organic matter: High distribution coefficients with consequences for environmental fate modeling Chemosphere 2007, 67 (5) 990-997
8. Sibley, S. D.; Pedersen, J. A. Interaction of the macrolide antimicrobial clarithromycin with dissolved humic acid Environ. Sci. Technol. 2008, 42 (2) 422-428
9. Bronner, G.; Goss, K.-U. Sorption of organic chemicals to soil organic matter: influence of soil variability and pH dependence Environ. Sci. Technol. 2011, 45 (4) 1307-1312
10. Ter Laak, T. L.; Durjava, M.; Struijs, J.; Hermens, J. L. M. Solid phase dosing and sampling technique to determine partition coefficients of hydrophobic chemicals in complex matrixes Environ. Sci. Technol. 2005, 39 (10) 3736-3742
11. EU Technical Guidance Document on Risk Assessment, Part II (Chapter 3) Environmental Risk Assessment; European Chemicals Bureau: Ispra, 2006.
12. Bi, E.; Schmidt, T. C.; Haderlein, S. B. Environmental factors influencing sorption of heterocyclic aromatic compounds to soil Environ. Sci. Technol. 2007, 41 (9) 3172-3178
13. Beaulieu, J. J.; Tank, J. L.; Kopacz, M. Sorption of imidazolium-based ionic liquids to aquatic sediments Chemosphere 2008, 70, 1320-1328
14. MacKay, A. A.; Seremet, D. E. Probe compounds to quantify cation exchange and complexation interactions of ciprofloxacin with soils Environ. Sci. Technol. 2008, 42 (22) 8270-8276
15. Stepnowski, P.; Mrozik, W.; Nichthauser, J. Adsorption of alkylimidazolium and alkylpyridinium ionic liquids onto natural soils Environ. Sci. Technol. 2007, 41 (2) 511-516
16. Brownawell, B. J.; Chen, H.; Collier, J. M.; Westall, J. C. Adsorption of organic cations to natural materials Environ. Sci. Technol. 1990, 24 (8) 1234-1241
17. Ramil, M.; El Aref, T.; Fink, G.; Scheurer, M.; Ternes, T. A. Fate of beta blockers in squatic-sediment systems: sorption and biotransformation Environ. Sci. Technol. 2009, 44 (3) 962-970
18. Polubesova, T.; Nir, S. Modeling of organic and inorganic cation sorption by Illite Clays Clay Miner. 1999, 47 (3) 366-374
19. Polubesova, T.; Rytwo, G.; Nir, S.; Serban, C.; Margulies, L. Adsorption of benzyltrimethylammonium and benzyltriethylammonium on montmorillonite: Experimental studies and model calculations Clays Clay Miner. 1997, 45 (6) 834-841
20. Droge, S. T. J.; Goss, K.-U. Effect of sodium and calcium cations on the ion-exchange affinity of organic cations for soil organic matter Environ. Sci. Technol. 2012, 46 (11) 5894-5901
21. Karthikeyan, K. G.; Chorover, J. Humic acid complexation of basic and neutral polycyclic aromatic compounds Chemosphere 2002, 48 (9) 955-964
22. Richter, M. K.; Sander, M.; Krauss, M.; Christl, I.; Dahinden, M. G.; Schneider, M. K.; Schwarzenbach, R. P. Cation binding of antimicrobial sulfathiazole to Leonardite humic acid Environ. Sci. Technol. 2009, 43 (17) 6632-6638
23. Matsuda, M.; Kaminaga, A.; Hayakawa, K.; Takisawa, N.; Miyajima, T. Surfactant binding by humic acids in the presence of divalent metal salts Colloids Surf. A 2009, 347 (1-3) 45-49
24. Chen, Y.; Droge, S. T. J.; Hermens, J. L. M. Analyzing freely dissolved concentrations of cationic surfactant utilizing ion-exchange capability of polyacrylate coated solid-phase microextraction fibers J. Chromatogr., A 2012, 1252, 15-22
25. Cheng, S. L.; Yan, H. S.; Zhao, C. Q. The synergistic effect between hydrophobic and electrostatic interactions in the uptake of amino acids by strongly acidic cation-exchange resins J. Chromatogr., A 2006, 1108 (1) 43-49
26. Murakami, F. Quantitative structure-retention relationships in cation-exchange chromatography J. Chromatogr., A 1980, 198 (3) 241
27. Tolls, J. Sorption of veterinary pharmaceuticals in soils: A review Environ. Sci. Technol. 2001, 35 (17) 3397-3406
28. Franco, A.; Trapp, S. Estimation of the soil-water partition coefficient normalized to organic carbon for ionizable organic chemicals Environ. Toxicol. Chem. 2008, 27 (10) 1995-2004
29. Holten-Lutzhoft, H.-C.; Vaes, W. H. J.; Freidig, A. P.; Halling-Sorensen, B.; Hermens, J. L. M. Influence of pH and other modifying factors on the distribution behavior of 4-quinolones to solid phases and humic acids studied by ″negligible-depletion″ SPME-HPLC Environ. Sci. Technol. 2000, 34 (23) 4989-4994
30. Arnold, C. d. G.; Ciani, A.; Müller, S. R.; Amirbahman, A.; Schwarzenbach, R. P. Association of triorganotin compounds with dissolved humic acids Environ. Sci. Technol. 1998, 32 (19) 2976-2983
31. Hörsing, M.; Ledin, A.; Grabic, R.; Fick, J.; Tysklind, M.; Jansen, J. l. C.; Andersen, H. R. Determination of sorption of seventy-five pharmaceuticals in sewage sludge Water Res. 2011, 45 (15) 4470-4482
32. Bronner, G.; Goss, K.-U. Predicting sorption of pesticides and other multifunctional organic chemicals to soil organic carbon Environ. Sci. Technol. 2011, 45 (4) 1313-1319
33. Tülp, H. C.; Fenner, K.; Schwarzenbach, R. P.; Goss, K.-U. pH-Dependent sorption of acidic organic chemicals to soil organic matter Environ. Sci. Technol. 2009, 43 (24) 9189
34. Trapp, S.; Franco, A.; Mackay, D. Activity-based concept for transport and partitioning of ionizing organics Environ. Sci. Technol. 2010, 44 (16) 6123-6129
35. Schenzel, J.; Goss, K.-U.; Bucheli, T.; Schwarzenbach, R. P.; Droge, S. T. J. Experimentally determined soil organic matter-water sorption coefficients for different classes of natural toxins and comparison with estimated numbers Environ. Sci. Technol. 2012, 46 (11) 6118-6126
36. Lyon, W. G. Swelling of peats in liquid methyl, tetramethylene and propyl sulfoxides and in liquid propyl sulfone Environ. Toxicol. Chem. 1995, 14 (2) 229-236
37. Gustafsson, Ö.; Bucheli, T. Soot sorption of non-ortho and ortho substituted PCBs Chemosphere 2003, 53, 515-522
38. Ter Laak, T. L.; Gebbink, W. A.; Tolls, J. The effect of pH and ionic strength on the sorption of sulfachloropyridazine, tylosin, and oxytetracycline to soil Environ. Toxicol. Chem. 2006, 25 (4) 904-911
39. Schimpf, M. E.; Petteys, M. P. Characterization of humic materials by flow field-flow fractionation Colloids Surf. A 1997, 120 (1-3) 87-100
40. Kalinichev, A. G.; Kirkpatrick, R. J. Molecular dynamics simulation of cationic complexation with natural organic matter Eur. J. Soil Sci. 2007, 58 (4) 909-917
41. Siripinyanond, A.; Worapanyanond, S.; Shiowatana, J. Field-flow fractionation-inductively coupled plasma mass spectrometry: An alternative approach to investigate metal-humic substances interaction Environ. Sci. Technol. 2005, 39 (9) 3295-3301
42. Milne, C. J.; Kinniburgh, D. G.; Tipping, E. Generic NICA-Donnan model parameters for proton binding by humic substances Environ. Sci. Technol. 2001, 35 (10) 2049-2059
43. Nielsen, T.; Siigur, K.; Helweg, C.; Jørgensen, O.; Hansen, P. E.; Kirso, U. Sorption of polycyclic aromatic compounds to humic acid as studied by high-performance liquid chromatography Environ. Sci. Technol. 1997, 31 (4) 1102-1108
44. Endo, S.; Grathwohl, P.; Haderlein, S. B.; Schmidt, T. C. LFERs for soil organic carbon-water distribution coefficients (Koc) at environmentally relevant sorbate concentrations Environ. Sci. Technol. 2009, 43 (9) 3094-3100
45. Trapp, S.; Horobin, R. W. A predictive model for the selective accumulation of chemicals in tumor cells Eur. Biophys. J. 2008, 34, 959-966
46. Franco, A.; Wenjing, F. U.; Trapp, S. Influence of soil pH on the sorption of ionizable chemicals: Modeling advances Environ. Toxicol. Chem. 2009, 28 (3) 458-464
47. Abraham, M.; Acree, W. E., Jr Equations for the transfer of neutral molecules and ionic species from water to organic phases J. Org. Chem. 2010, 75 (4) 1006-1015
48. Aristilde, L.; Sposito, G. Molecular modeling of metal complexation by a fluoroquinolone antibiotic Environ. Toxicol. Chem. 2008, 27 (11) 2304-2310