Date of Award

Summer 1991

Document Type


Degree Name

Master of Science (MS)


Chemistry & Biochemistry



Committee Director

Frank E. Scully, Jr.

Committee Member

Robert L. Ake

Committee Member

Patricia A. Pleban

Call Number for Print

Special Collections LD4331.C45C66


Model solutions of the amino acid phenylalanine were chlorinated to seven Cl/N mole ratios. The by-products were characterized using gas chromatography, high performance liquid chromatography, GC/MS, infrared spectroscopy, and nuclear magnetic resonance spectroscopy. At the lower Cl/N ratios N-chlorophenylalanine and phenylacetaldehyde were identified as the main products while phenylacetonitrile and N-chlorophenylacetaldimine were the major products at Cl/N ratios of 2.0 and beyond. The concentration of phenylalanine in a municipal wastewater was determined. Using a radiotracer the chlorination products of phenylalanine in the wastewater at the 7 Cl/N ratios were identified as those seen in the model solutions. The distribution of the byproducts in the wastewater supports the idea that organic monochloramines may represent a significant percentage of the chlorine-containing oxidants present in wastewater at low chlorination levels used in treatment plants.


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