The sorption/desorption behavior in soil/water systems of $ sp{14}$C-radiolabeled naphthalene and nine of its nitrogen-substituted derivatives; quinoline, isoquinoline, quinoxaline, 1-aminonaphthalene, 2-aminonaphthalene, 1-amino-2-methylnaphthalene, 1-nitronaphthalene, 2-nitronaphthalene and 1-nitro-2-methylnaphthalene were investigated with respect to their physico-chemical properties and the type of interaction they form with soil organic and mineral matter. In turn, an investigation into the effect that sorption/desorption has on the bioavailability of these organic compounds and their mineralization kinetics was conducted. / The non-polar naphthalene, the slightly polar quinoxaline and the three nitronaphthalene compounds sorbed through hydrophobic interaction giving rise to linear sorption isotherms that are typical of partitioning processes in which organic matter functions as a partition medium. Amino-naphthalenes, being polar and slightly basic, adsorbed through cation exchange, hydrogen bonding and formed coordination complexes at soil organic and mineral matter surfaces. Quinoline and isoquinoline, due to their relatively high dipole moment, intercalated the interlamellar space of layered-soil minerals. However, quinoline did not exhibit a specific type of interaction in the interlamellar region, while isoquinoline molecules adsorbed specifically, probably through surface protonation or coordinate covalent bonding with metal ions, and produced micelles upon sorption between the basal planes of clay particles. The discrepancy between the sorption behavior of quinoline and that of isoquinoline is attributed, in part, to the stronger hygroscopic nature of the former compound, its lower acidity constant and to the asymmetric shape of its molecules. / The desorption behaviors of naphthalene and 1-nitro-2-methylnaphthalene, both yielding concave up desorption isotherms, show a readily reversible component that gradually gives way to an irreversible one. The -CH$ sb3$ group, in the case of 1-nitro-2-methylnaphthalene, reduced hysteresis which is attributed to an increase in the hydrophobicity of the molecule and the steric effect that the methyl substitution has on hydrogen bonding. Desorption of quinoline and isoquinoline followed a hysteresis loop (concave down desorption isotherm) such that reversibility increased with decreasing soluble concentrations in the aqueous phase. Amino-naphthalenes adsorbed irreversibly at soil surfaces which is suggestive of strong interaction forces resembling those of a chemical reaction. / The mineralization of all studied compounds gave rise to hyperbolic mineralization curves comprising two phases; an initial fast one followed by a second slow phase with gradually declining rates. / Quinoline maximum mineralization rates were first order with respect to soluble concentrations and the amounts of quinoline mineralized initially coincided with the soluble fraction. In contrast, the amounts of isoqoinoline mineralized during the fast phase exceeded its corresponding fractions in solution. Mineralization exhibited saturation-type kinetics (Michaelis-Menten type) which probably indicates that the biodegradation of isoquinoline was mediated by its sorption in the micellar form. / Finally, naphthalene maximum mineralization rates correlated linearly with total concentrations (soluble and sorbed) and the total amounts mineralized during the fast phase exceeded substantially the soluble fraction. (Abstract shortened by UMI.)
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.28654 |
| Date | January 1994 |
| Creators | Al-Bashir, Bilal. |
| Contributors | Leduc, Ronald (advisor) |
| Publisher | McGill University |
| Source Sets | Library and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada |
| Language | English |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Format | application/pdf |
| Coverage | Doctor of Philosophy (Department of Civil Engineering and Applied Mechanics.) |
| Rights | All items in eScholarship@McGill are protected by copyright with all rights reserved unless otherwise indicated. |
| Relation | alephsysno: 001448223, proquestno: NN05659, Theses scanned by UMI/ProQuest. |
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