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Abstract STABILITY of POLYCYCLIC AROMATIC HYDROCARBONS

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Abstract STABILITY of POLYCYCLIC AROMATIC HYDROCARBONS Abstract STABILITY OF POLYCYCLIC AROMATIC HYDROCARBONS AND BENZOIC ACID DERIVATIVES UNDER SUBCRITICAL WATER CONDITIONS By Edward J. Lindquist March 2011 Chair: Dr. Rickey P. Hicks Major Department: Chemistry The development of green environmental remediation, chromatography, and extraction techniques using subcritical water is the focus of our research group. The polarity of subcritical water can be manipulated by increasing its temperature in the range of 25 to 374 ºC while keeping it in the liquid state under moderate pressure. At elevated temperatures liquid water becomes less polar and behaves more like an organic solvent. The goal of this research is to determine the conditions under which certain polycyclic aromatic hydrocarbons (PAHs) and benzoic acid derivatives degrade in subcritical water. The stability of two PAHs (pyrene and naphthalene) and benzoic acid and three of its derivatives (anthranilic acid, syringic acid, and salicylic acid) under subcritical water conditions was investigated and the results are discussed in this thesis. PAHs are pollutants widely formed as a result of incomplete combustion of organic materials. The effects of temperatures ranging from 200 to 350 ºC and heating times of 30 and 300 min on the degradation of pyrene and naphthalene in solutions of water and 3% hydrogen peroxide were determined. Our results show that PAHs can be degraded under subcritical water conditions, and thus, this technique may be applied to the environmental remediation of these pollutants. Benzoic acid and its derivatives are found in medicinal herbs and other plants. While the extraction of these active ingredients from herbs using subcritical water is non-toxic and preferred, the decomposition of these compounds under subcritical water conditions has to be examined. The stability studies of this group of analytes were carried out at temperatures ranging from 50 to 250 ºC with heating times of 10 and 30 min. The degradation of the benzoic acid derivatives increased with rising temperature and additional heating time. The degradation products of benzoic acid and the three derivatives were identified and quantified by high-performance liquid chromatography (HPLC) and confirmed by gas chromatography/mass spectrometry (GC/MS). Under subcritical water conditions anthranilic acid, syringic acid, salicylic acid, and benzoic acid underwent decarboxylation to form aniline, syringol, phenol, and benzene, respectively. STABILITY OF POLYCYCLIC AROMATIC HYDROCARBONS AND BENZOIC ACID DERIVATIVES UNDER SUBCRITICAL WATER CONDITIONS A Thesis Presented To The Faculty of the Department of Chemistry East Carolina University In Partial Fulfillment of the Requirements for the Degree Master of Science By Edward J. Lindquist March 2011 ©Copyright 2011 Edward J. Lindquist STABILITY OF POLYCYCLIC AROMATIC HYDROCARBONS AND BENZOIC ACID DERIVATIVES UNDER SUBCRITICAL WATER CONDITIONS By Edward J. Lindquist APPROVED BY: DIRECTOR OF THESIS: Yu Yang, PhD COMMITTEE MEMBER: Colin S. Burns, PhD COMMITTEE MEMBER: Anthony Kennedy, PhD COMMITTEE MEMBER: Cindy Putnam-Evans, PhD CHAIR OF THE DEPARTMENT OF CHEMISTRY: Rickey P. Hicks, PhD DEAN OF THE GRADUATE SCHOOL: Paul J. Gemperline, PhD DEDICATION This thesis is dedicated to my wife, Cher Lindquist. Without her love, support, and patience I would not have been able to succeed in this endeavor. ACKNOWLEDGMENTS I would like to thank my family for their support and encouragement over the years it has taken me to reach this goal. I am grateful for Dr. Yu Yang’s guidance throughout the course of my research. His enthusiasm kept me moving forward even when things got difficult. I would like to express my thanks to Dr. Colin Burns, Dr. Anthony Kennedy, and Dr. Cindy Putnam-Evans for being on my thesis committee and challenging me to better understand the results of my experiments. I appreciate the assistance given by the members of our research group: Zack Strickland, Leena Gujjar, Ann Marie Toebes, Marina Rybnikova, Bryan Pate, Chris Baker, Heather Anderson, Chris Jones, and Brett Weed. Their friendship and the camaraderie of my fellow graduate students made the late nights in the lab bearable. I would like to thank Dr. Rickey Hicks and Dr. Brian Love for answering questions about my research that were in their areas of expertise. I am thankful for the metal work done by Jim Saupe in the Department of Physics and the wooden vial trays made by Steve Simonds. I appreciate the advice on HPLC instrumentation and method development from Phil Hodges, Jennifer Warren, Nicole Wilkerson, Kevin Jones, Elizabeth Boswell, Fallon O’Neal, Kym Rispress, and John Arnold of Metrics, Inc. I also thank Dr. Arpie Korkin of Phenomenex, Inc. for her suggestions on HPLC column selection. TABLE OF CONTENTS LIST OF TABLES................................................................................................... xi LIST OF FIGURES................................................................................................. xii LIST OF SYMBOLS AND ABBREVIATIONS.................................................... xiv CHAPTER 1: INTRODUCTION............................................................................ 1 1.1 Chemistry Using Subcritical Water......................................................... 1 1.1.1 Subcritical Water Extraction....................................................... 1 1.1.2 Subcritical Water Chromatography............................................ 2 1.1.3 Chemical Reactions in Subcritical Water................................... 2 1.2 Organic Degradation in Subcritical Water.............................................. 3 1.3 The Goal of This Research...................................................................... 4 CHAPTER 2: BACKGROUND.............................................................................. 5 2.1 Polycyclic Aromatic Hydrocarbons......................................................... 5 2.2 Benzoic Acid and Derivatives................................................................. 7 2.3 Organic Degradation in Subcritical Water and Its Mechanism…........... 10 CHAPTER 3: EXPERIMENTAL........................................................................... 19 3.1 Chemicals and Materials.......................................................................... 19 3.2 Reaction and Analytical Systems............................................................ 20 3.3 Experimental Procedures......................................................................... 23 3.3.1 Pyrene......................................................................................... 23 3.3.2 Naphthalene................................................................................ 25 3.3.3 Benzoic Acid and Derivatives.................................................... 27 3.4 Experimental Conditions......................................................................... 30 3.4.1 GC Analysis for Pyrene.............................................................. 30 3.4.2 GC Analysis for Naphthalene..................................................... 31 3.4.3 HPLC Analysis for Benzoic Acid and Derivatives.................... 32 3.4.4 GC/MS Analysis for Benzoic Acid and Derivatives.................. 32 CHAPTER 4: RESULTS AND DISCUSSION...................................................... 34 4.1 Polycyclic Aromatic Hydrocarbons......................................................... 34 4.2 Benzoic Acid and Derivatives................................................................. 37 4.2.1 Effects of Temperature and Heating Time on Degradation........ 38 4.2.2 Degradation Products and Mechanism....................................... 46 CHAPTER 5: CONCLUSIONS.............................................................................. 59 REFERENCES........................................................................................................ 60 LIST OF TABLES 1. Decomposition of Naphthalene (Reaction time 60 min).................................... 12 2. Decomposition of Phenanthrene (Sample size 0.1 g)......................................... 13 3. Decomposition of Pyrene (Sample size of 0.1 g, 6 vol% H 2O2)........................ 14 4. Temperature Effect on Phenanthrene Degradation in Deionized Water............ 16 5. Temperature Effect on Phenanthrene Degradation in 3% Hydrogen Peroxide-97% Water Mixture............................................................................. 16 6. Summary of Pyrene Degradation after 30-min Heating..................................... 34 7. Summary of Pyrene Degradation after 300-min Heating................................... 35 8. Summary of Naphthalene Degradation after 30-min Heating............................ 36 9. Summary of Naphthalene Degradation after 300-min Heating.......................... 37 10. Temperature Effect on Organic Acid Degradation in Degassed Water after 10-min Heating......................................................................................... 39 11. Temperature Effect on Organic Acid Degradation in Degassed Water after 30-min Heating......................................................................................... 40 12. Effects of Temperature and Heating Time on Benzoic Acid Degradation in Degassed Water................................................................................................ 41 13. Quantification of Degradation Products for Anthranilic Acid, Syringic Acid, and Salicylic Acid............................................................................................
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