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Advancements in Liquid Chromatography for the Determination of Polycyclic Aromatic Compounds in Environmental Samples

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Advancements in Liquid Chromatography for the Determination of Polycyclic Aromatic Compounds in Environmental Samples University of Central Florida STARS Electronic Theses and Dissertations, 2004-2019 2018 Advancements in Liquid Chromatography for the Determination of Polycyclic Aromatic Compounds in Environmental Samples Hugh Hayes University of Central Florida Part of the Chemistry Commons Find similar works at: https://stars.library.ucf.edu/etd University of Central Florida Libraries http://library.ucf.edu This Doctoral Dissertation (Open Access) is brought to you for free and open access by STARS. It has been accepted for inclusion in Electronic Theses and Dissertations, 2004-2019 by an authorized administrator of STARS. For more information, please contact [email protected]. STARS Citation Hayes, Hugh, "Advancements in Liquid Chromatography for the Determination of Polycyclic Aromatic Compounds in Environmental Samples" (2018). Electronic Theses and Dissertations, 2004-2019. 5951. https://stars.library.ucf.edu/etd/5951 ADVANCEMENTS IN LIQUID CHROMATOGRAPHY FOR THE DETERMINATION OF POLYCYCLIC AROMATIC COMPOUNDS IN ENVIRONMENTAL SAMPLES by HUGH V. HAYES B.S. Chemistry Stevenson University, 2012 M.S. Forensic Chemistry Stevenson University, 2013 M.S. Analytical Chemistry University of Central Florida, 2015 A dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the Department of Chemistry in the College of Sciences at the University of Central Florida Orlando, Florida Summer Term 2018 Major Professor: Andres D. Campiglia © 2018 Hugh V. Hayes ii ABSTRACT The purpose of this dissertation is to provide a new and improved analytical methodology for the analysis of polycyclic aromatic hydrocarbons (PAHs) and polycyclic aromatic sulfur heterocycles (PASHs) in environmental samples. Hundreds of PAHs and PASHs are present in the environment and have great toxicological importance and the chemical determination of these components is a priority. The complete normal-phase liquid chromatography (NPLC) retention behavior has been explored for these compounds. Retention indices were determined for 124 PAHs, 62 methyl-PAHs (MePAHs), 67 PASHs, and 80 alkyl-PASHs on an aminopropyl (NH2) stationary phase which represents the most comprehensive study of polycyclic aromatic compounds in normal phase conditions to date. NPLC retention behavior for PAHs and PASHs directly correlated to the total number of aromatic carbons in the parent structures. The normal-phase retention behavior information was used to develop an NPLC fractionation procedure to aid in the sample cleanup for complex environmental matrices which can later be analyzed by gas chromatography/mass spectrometry (GC/MS). Standard Reference Material (SRM) 1597a (complex mixture of PAHs in coal tar), SRM 1991 (coal tar/petroleum extract), and SRM 1975 (diesel particulate extract) were analyzed before and after NPLC fractionation by using GC/MS. In SRM 1597a, the NPLC-GC/MS method allowed for the identification of 72 PAHs, 56 Me-PAHs, 35 PASHs, and 59 alkyl-PASHs. The NPLC-GC/MS procedure also provided the tentative identification of 74 PAHs and 117 MePAHs based on the molecular ion peak only. Furthermore, this method allowed for the following identification breakdown: SRM 1991–31 PASHs and 58 alkyl-PASHs; and SRM 1975–13 PASHs and 25 alkyl- PASHs. iii Additional work related to the NPLC fractionation of SRM 1597 included the collection of room-temperature fluorescence spectra for the 21 PAHs with molecular mass (MM) 302 Da known to be in SRM 1597a during reversed-phase liquid chromatography (RPLC) separation. Adding spectral features to a chromatographic run provided the tentative identification of 20 PAHs based on retention times and the presence of 18 were confirmed on the basis of spectral profiles. The advancements in liquid chromatography presented in this dissertation via NPLC fractionation along with RPLC stop-flow fluorescence spectra collection shows potential for becoming routine methodologies for PAC determination in complex environmental samples. iv To my niece, Presley Rose v ACKNOWLEDGMENTS I would like to give special thanks to my advisor Dr. Andres D. Campiglia for everything he has provided for me throughout my time pursuing a Ph.D. in Chemistry at University of Central Florida. His support, experience, knowledge, and guidance has helped me become not only a better chemist, but a better scientist and person overall. His advice for me has led to amazing opportunities that I cannot see possible without his enthusiasm towards my success. I would also like to thank my dissertation committee: Dr. Cherie L. Yestrebsky, Dr. James K. Harper, Dr. Andrew Frazer, and Dr. Kevin R. Coffey for their support throughout my graduate career at UCF. It is an honor to have them as my dissertation committee members. Throughout my time at UCF, I had the privilege to meet and work with some amazing people. Foremost, I want to give a special shout-out to Dr. Madeline Johnson. Our time together during the long laborious hours over the past several years in the lab has formed a friendship that I will cherish for the rest of my life. I would also like to thank Dr. Walter B. Wilson for all his mentoring and valuable input in my research and career aspirations. I want to thank the National Institute of Standards and Technology for having me as a guest researcher at their Maryland campus for a total of 6 months and the Gulf of Mexico Research Initiative for financially making this possible. Gratitude is also expressed to Dr. Lane C. Sander, Dr. Stephen A. Wise, Dr. Erin K. H. Saitta, Dr. Tracey M. Mason, Dr. Jason L. Sonnenberg, Dr. Anthony F. T. Moore, Dr. Bassam F. Alfarhani, Dr. Alaa A. Fadhel, Dr. Nirvani Mujumdar, Dr. Maha Al-Tameemi, Dr. Stacey Wise, Khang Trieu, Anthony Santana, Jim Janesko, Ahmed Comas, Reza Chehelamirani, Sadia Arif, Wansakkarage Chandana, Brooke Bayer, Keven Moldenhauer, and Mandi Sheroke. I would also like to thank my parents, sister, and especially my niece, Presley Rose, for their unconditional love, support, and encouragement for me to follow my dreams. While it is difficult being so far away from my family, their support means more than words can describe. Last but certainly not least, I want to thank my best friends Joel Nelson, Scott Kinlein, Wes Morales, and Matt Logan. I am truly grateful to have a group of friends that I can call brothers who push me to be the best. Thank you. vi TABLE OF CONTENTS LIST OF FIGURES ...................................................................................................................... xii LIST OF TABLES ....................................................................................................................... xxi INTRODUCTION....................................................................................................... 1 1.1 Polycyclic aromatic compounds....................................................................................... 1 1.2 Toxicity of polycyclic aromatic hydrocarbons ................................................................. 3 1.3 Polycyclic aromatic sulfur heterocycles ........................................................................... 9 1.4 Chromatography ............................................................................................................. 10 1.4.1 NPLC ...................................................................................................................... 11 1.4.2 GC/MS .................................................................................................................... 13 1.4.3 RPLC....................................................................................................................... 14 1.5 Fluorescence detection ................................................................................................... 18 1.6 Standard reference materials .......................................................................................... 19 1.7 Dissertation objectives ................................................................................................... 21 1.8 References ...................................................................................................................... 21 NORMAL-PHASE LIQUID CHROMATOGRAPHY BEHAVIOR OF PAHS AND THEIR METHYL-DERIVATIVES ON AN AMINOPROPYL STATIONRY PHASE ............ 37 2.1 Introduction .................................................................................................................... 37 2.2 Experimental .................................................................................................................. 38 vii 2.2.1 Chemicals ................................................................................................................ 38 2.2.2 Thickness calculations ............................................................................................ 38 2.2.3 NPLC retention index data...................................................................................... 39 2.2.4 Statistical t-test calculations .................................................................................... 41 2.3 Results and Discussion ................................................................................................... 41 2.3.1 Two-ring and three-ring PAHs ............................................................................... 51 2.3.2 Four-ring PAHs ....................................................................................................... 55 2.3.3 Five-ring PAHs ......................................................................................................
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