High molecular weight – polycyclic aromatic hydrocarbons (HMW-PAH) are often found where air, water, and soil are subject to higher levels of industrial pollutants. These molecules are environmentally concerning due to their carcinogenic, mutagenic, and tumorigenic propensities. Furthermore, the isomers in this family are challenging to separate due to similar retention parameters, spectroscopic fingerprints, and mass spectral patterns. The primary purpose of this dissertation is to expand on the methodology for separation and analysis of the molecular mass 302 Da six-ring isomers using High Performance Liquid Chromatography. Retention behaviors of 21 commercially available isomers in synthetic mixture were collected via two different approaches. The first approach utilized normal phase chromatography with an aminopropyl stationary phase. This column type has been used in prior PAH research to perform fractionation of complex samples. The subsequent approach utilized chiral chromatography with a cellulose tris (3,5-dimethylphenylcarbamate) column. Chiral columns are used predominantly to separate chiral enantiomers. While chiral based separation is known and expected for enantiomeric molecules, the capacity for separating achiral isomers using this approach remains largely unexplored, and use described herein for separation of PAHs in this manner has not been published to date. The work includes the extensive separation of the isomeric family of MM 302 Da PAHs. Factor calculations given in EPA chromatographic guidance are included to improve qualitative identification of the raw retention data for the 21 isomers. Quantitative data for 14 of the isomers is presented. The research provides comparison of the chiral chromatographic method to the aminopropyl stationary phase method, illustrating advantages each method may have over the other. This method also provides a foundation for future separation strategies of HMW-PAHS using chiral stationary phases. The dissertation concludes with the proposal of combining both methods within a two-dimensional approach. The use of the aminopropyl stationary phase would perform the initial fractionation needed to separate a complex environmental sample. The primary fractions are followed by a chiral secondary separation for quantitation. This approach could potentially save the analyst time and resources while identifying and quantifying a challenging family of industrial pollutants.
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Doctor of Philosophy (Ph.D.)
College of Sciences
Length of Campus-only Access
Doctoral Dissertation (Open Access)
Janesko, James, "A Developmental Investigation of Separation and Analysis of Molecular Mass 302 Da Polyaromatic Hydrocarbons using High Performance Liquid Chromatography and Chiral Stationary Phase" (2023). Electronic Theses and Dissertations, 2020-. 1582.