New insight into adsorption mechanism of ionizable compounds on carbon nanotubes

Environmental Science and Technology

Volumn 47, Issue 15, 2013, Pages 8334-8341

  Li, Xiaoyun ^a,b   Pignatello, Joseph J ^c   Wang, Yiquan ^a   Xing, Baoshan ^b  

^a NORTHWEST A F UNIVERSITY   (China)

^b UNIVERSITY OF MASSACHUSETTS   (United States)

^c Connecticut Agricultural Experiment Station ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 ,6-DICHLORO-4-NITROPHENOL; ADSORPTION MECHANISM; CARBONACEOUS MATERIALS; CARBONACEOUS SURFACE; IONIZABLE COMPOUNDS; IONIZABLE ORGANIC COMPOUNDS; LIGAND EXCHANGE REACTIONS; NATURAL ORGANIC MATTERS;

ASSOCIATION REACTIONS; CARBON NANOTUBES; CARBOXYLATION; GRAPHITIZATION; IONS; STOICHIOMETRY; SURFACES;

ADSORPTION;

BENZOIC ACID; CARBON NANOTUBE; CARBOXYLIC ACID; HYDROXIDE; NATURAL ORGANIC MATTER; ORGANIC COMPOUND; PHTHALIC ACID; PROTON;

ADSORPTION; CARBOXYLIC ACID; COMPARATIVE STUDY; FUNCTIONAL GROUP; ION EXCHANGE; IONIZATION; LIGAND; ORGANIC MATTER; PH; PHENOL; REACTION KINETICS;

ADSORPTION; ANION EXCHANGE; ARTICLE; DERIVATIZATION; DISSOCIATION CONSTANT; DISSOLUTION; ENVIRONMENTAL IMPACT; HYDROPHOBICITY; IONIZATION; POLLUTANT; PROTON TRANSPORT; STEREOSPECIFICITY; STOICHIOMETRY; STRUCTURE ACTIVITY RELATION; THERMODYNAMICS; ZETA POTENTIAL;

ADSORPTION; HYDROGEN BONDING; IONS; NANOTUBES, CARBON;

EID: 84881399949     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es4011042     Document Type: Article

References (43)

1. Chen, W.; Duan, L.; Wang, L. L.; Zhu, D. Q. Adsorption of hydroxyl- and amimo-substituted aromatics to carbon nanotubes Environ. Sci. Technol. 2008, 42 (18) 6862-6868
2. Yang, K.; Wu, W. H.; Jing, Q. F; Zhu, L. Z. Aqueous adsorption of aniline, phenol, and their substitutes by multi-walled carbon nanotubes Environ. Sci. Technol. 2008, 42 (21) 7931-7936
3. Chen, J.; Chen, W.; Zhu, D. Q. Adsorption of nonionic aromatic compounds to single-walled carbon nanotubes: Effects of aqueous solution chemistry Environ. Sci. Technol. 2008, 42 (19) 7225-7230
4. Pyrzynska, K.; Stafiej, A.; Biesaga, M. Sorption behavior of acidic herbicides on carbon nanotubes Microchim. Acta 2007, 159 (3-4) 293-298
5. 3 Carbon 2008, 46 (3) 553-555
6. Müller, G.; Radke, C. J.; Prausnitz, J. M. Adsorption of weak organic electrolytes from aqueous solution on activated carbon. Effect of pH J. Phys. Chem. 1980, 84, 369-376
7. Müller, G.; Radke, C. J.; Prausnitz, J. M. Adsorption of weak organic electrolytes from dilute aqueous solution onto activated carbon. Part I. Single-solute systems J. Colloid Interface Sci. 1985, 103, 466-483
8. Radovic, L. R.; Moreno-Castilla, C.; Rivera-Utrilla, J. In Chemistry and Physics of Carbon: A Series of Advances; Radovic, L. R., Ed.; Marcel Dekker, Inc.: New York, 2001; Vol. 27, pp 227-405.
9. Moreno-Castilla, C. Adsorption of organic molecules from aqueous solutions on carbon materials Carbon 2004, 42, 83-94
10. Li, Q.; Snoeyink, V. L.; Mariãas, B. J.; Campos, C. Elucidating competitive adsorption mechanisms of atrazine and NOM using model compounds Water Res. 2003, 37, 773-784
11. Müller, E. A.; Hung, F. R.; Gubbins, K. E. Adsorption of water vapor-methane mixtures on activated carbons Langmuir 2000, 16, 5418-5424
12. Zhu, D.; Kwon, S.; Pignatello, J. J. Adsorption of single-ring organic compounds to wood charcoals prepared under different thermochemical conditions Environ. Sci. Technol. 2005, 39, 3990-3998
13. Moreno-Castilla, C. Adsorption of organic molecules from aqueous solutions on carbon materials Carbon 2004, 42, 83-94
14. Ni, J.; Pignatello, J. J.; Xing, B. S. Adsorption of aromatic carboxylate ions to charcoal black carbon (biochar) is accompanied by proton exchange with water Environ. Sci. Technol. 2011, 45 (21) 9240-9248
15. Teixido, M.; Pignatello, J. J.; Beltran, J. L.; Granados, M.; Peccia, J. Speciation of the ionizable antibiotic sulfamethazine on black carbon Environ. Sci. Technol. 2011, 45 (23) 10020-10027
16. Gilli, G.; Gilli, P. Towards an unified hydrogen-bond theory J. Mol. Struct. 2000, 552 (1-3) 1-15
17. Gilli, P.; Pretto, L.; Bertolasi, V.; Gilli, G. Predicting hydrogen-bond strengths from acid-base molecular properties. The pK(a) slide rule: Toward the solution of a long-lasting problem Acc. Chem. Res. 2009, 42 (1) 33-44
18. Cleland, W. W.; Kreevoy, M. M. Low-barrier hydrogen bonds and enzymic catalysis Science 1994, 264, 1887-1890
19. Jesus, A. J. L.; Redinha, J. S. Charge-assisted intramolecular hydrogen bonds in disubstituted cyclohexane derivatives J. Phys. Chem. A 2011, 115, 14069-14077
20. Liang, J.; Horton, J. H. Interactions of benzoic acid and phosphates with iron oxide colloids using chemical force titration Langmuir 2005, 21, 10608-10614
21. Méndez-Díaz, J. D.; Abdel-Daiem, M. M.; Rivera-Utrilla, J.; Sánchez-Polo, M. Adsorption/bioadsorption of phthalic acid, an organic micropollutant present in landfill leachates, on activated carbons J. Colloid Interface Sci. 2012, 369, 358-365
22. Gluck, S. J.; Benkö, M. H.; Hallberg, R. K.; Steele, K. P. Indirect determination of octanol-water partition coefficients by microemulsion electrokinetic chromatography J. Chromatogr., A 1996, 744, 141-146
23. Cronin, M. T. D.; Manga, N.; Seward, J. R.; Sinks, G. D.; Schultz, T. W. Parametrization of electrophilicity for the prediction of the toxicity of aromatic compounds Chem. Res. Toxicol. 2001, 14, 1498-1505
24. Behera, S. K.; Oh, S. Y.; Park, H. S. Sorption of triclosan onto activated carbon, kaolinite and montmorillonite: Effect of pH, ionic strength, and humic acid J. Hazard. Mater. 2010, 179 (1-3) 684-691
25. Hyun, S.; Lee, L. S. Hydrophilic and hydrophobic sorption of organic acids by variable-charge soil: Effect of chemical acidity and acidic functional group Environ. Sci. Technol. 2004, 38 (20) 5413-5419
26. Dubus, I. G.; Barriuso, E.; Calvet, R. Sorption of weak organic acids in soils: Clofencet, 2,4-D and salicylic acid Chemosphere 2001, 45 (6-7) 767-774
27. Aquino, A. J. A.; Tunega, D.; Haberhauer, G.; Gerzabek, M. H.; Lischka, H. Interaction of the 2, 4-diclorophenoxyacetic acid herbicide with soil organic matter moieties: A theoretical study Eur. J. Soil Sci. 2007, 58, 889-899
28. Aristilde, L.; Sposito, G. Binding of ciprofloxacin by humic substances: A molecular dynamics study Environ. Toxicol. Chem. 2010, 29 (1) 90-98
29. Iskrenova-Tchoukova, E.; Kalinichev, A. G.; Kirkpatrick, R. J. Metal cation complexation with natural organic matter in aqueous solutions: Molecular dynamics simulations and potentials of mean force Langmuir 2010, 26 (20) 15909-15919
30. MacKay, A. A.; Canterbury, B. Oxytetracycline sorption to organic matter by metal-bridging J. Environ. Qual. 2005, 34, 1964-1971
31. Fontecha-Camara, M. A.; Lopez-Ramon, M. V.; Alvarez-Merino, M. A.; Mereno-Castilla, C. Effects of surface chemistry, solution pH, and ionic strength on the removal of herbicides diuron and amitrole from water by an activated carbon fiber Langmuir 2007, 23 (3) 1242-1247
32. Vinu, A.; Hossain, K. Z.; Kumar, G. S.; Ariga, K. Adsorption of l -histidine over mesoporous carbon molecular sieves Carbon 2006, 44 (3) 530-536
33. Cho, H. H.; Huang, H. O.; Schwab, K. Effects of solution chemistry on the adsorption of ibuprofen and triclosan onto carbon nanotubes Langmuir 2011, 27 (21) 12960-12967
34. Zhang, S. J.; Shao, T.; Bekaroglu, S. S. K.; Karanfil, T. Adsorption of synthetic organic chemicals by carbon nanotubes: Effects of background solution chemistry Water Res. 2010, 44, 2067-2074
35. Chernyshova, I. V.; Ponnurangam, S.; Somasundaran, P. Adsorption of fatty acids on iron (hydr) oxides from aqueous solution Langmuir 2011, 27, 10007-10018
36. Norén, K.; Persson, P. Adsorption of monocarboxylates at the water/goethite interface: The importance of hydrogen bonding Geochim. Cosmochim. Acta 2007, 71, 5717-5730
37. Thomas, J. E.; Kelley, M. J. Interaction of mineral surfaces with simple organic molecules by diffuse reflectance IR spectroscopy (DRIFT) J. Colloid Interface Sci. 2008, 322, 516-526
38. Maity, N.; Payne, G. F. Adsorption from aqueous solutions based on a combination of hydrogen bonding and hydrophobic interactions Langmuir 1991, 7, 1247-1254
39. Lide, D. R. Handbook of Chemistry and Physics, 85 th ed.; CRC Press: Boca Raton, FL, 2004.
40. Tolstoy, P. M.; Schah-Mohammedi, P.; Smirnov, S. N.; Golubev, N. S.; Denisov, G. S.; Limbach, H. H. Characterization of fluxional hydrogen-bonded complexes of acetic acid and acetate by NMR: Geometries and isotope and solvent effects J. Am. Chem. Soc. 2004, 126 (17) 5621-5634
41. Han, J.; Deming, R. L.; Tao, F. M. Theoretical study of hydrogen-bonded complexes of chlorophenols with water or ammonia: Correlations and predictions of p K a values J. Phys. Chem. A 2005, 109, 1159-1167
42. Nielsen, M. F. A model for quantitative evaluation of equilibrium constants for hydrogen bonding in polar aprotic solvents based on incomplete data sets related to different solvents Acta Chem. Scand. 1992, 46, 533-548
43. Zhao, Y. H.; Abraham, M. H.; Zissimos, A. M. Fast calculation of van der Waals volume as a sum of atomic and bond contributions and its application to drug compounds J. Org. Chem. 2003, 68 (19) 7368-7373