Assessing the Fate of Organic Contaminants in Aquatic Environments: Mechanism and Kinetics of Hydrolysis of a Carboxylic Ester
Jorg Klausen, Markus A. Meier , and Rene P. Schwarzenbach Swiss Federal Institute for Environmental Science and Technology (EAWAG), Environmental Organic Chemistry, Ueberlandstrasse 133, DŸbendorf CH-8600 SWITZERLAND
An integrated experiment is proposed for an upper level under-graduate environmental chemistry laboratory. Using 2,4-dinitrophenylacetate (DNPA) as an example, the mechanisms of the abiotic hydrolysis of carboxylic esters are presented and the kinetic expressions are derived. The proposed experimental set-up uses isocratic reversed phase HPLC with UV detection to follow the decrease of DNPA concentration during hydrolysis experiments. The Arrhenius parameters of the rate constants for the neutral and base-catalyzed abiotic hydrolysis are evaluated using hydrolysis rates obtained at various pH values and temperatures. With these parameters, the half-life of the compound under given environmental conditions can be assessed. The experiment is very well suited to introduce or repeat important basic concepts of kinetics and instrumental analysis and to sensitize the students for the often complex nature of environmental processes.
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Citation
Klausen, Jorg; Meier, Markus A.; Schwarzenbach, Rene P. J. Chem. Educ.1997 74 1440.
Keywords
Laboratory Instruction, Physical Chemistry, Environmental Chemistry, Kinetics, Mechanisms, and Chromatography
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