Date of Award

Fall 1991

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry & Biochemistry

Program/Concentration

Chemistry

Committee Director

Frank E. Scully, Jr.

Committee Member

Robert L. Ake

Committee Member

Charles E. Bell

Call Number for Print

Special Collections LD4331.C45M33

Abstract

Solutions of the amino acid valine were chlorinated to seven chlorine-to-nitrogen mole (Cl/N) ratios and analyzed by high performance liquid chromatography, gas chromatography/mass spectroscopy, infrared spectroscopy, and nuclear magnetic resonance spectroscopy. The chlorination products found were N-chlorovaline, isobutyraldehyde, isobutyronitrile, and N-chloroisobutyraldimine. Their product distribution depends on the level of chlorination and pH. The main products identified at the lower CI/N mole ratios were N-chlorovaline and isobutyraldehyde, whereas at the higher CI/N mole ratios isobutyronitrile and N-chloroisobutyraldimine were identified as the main products. The concentration and the chlorination products of valine in municipal wastewater were also determined. The chlorination products of valine in wastewater were detected with the aid of a radiotracer and were found to be similar to those found in the model solutions. A scheme is proposed for the formation of the chlorination products of valine. At Cl/N mole ratios < 1, N-chlorovaline is the major by-product present in valine solutions 30 min after chlorination. At higher Cl/N mole ratios N-chloroisobutyraldimine and isobutyronitrile are the two major products of the chlorination of valine in both model solutions and in wastewaters. N-Chloroisobutyraldimine is stable in aqueous solutions with a half-life of 34 hrs.

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