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Environmental Fate, (Bio)Transformation, and Toxicology of 2,4-Dinitroanisole (DNAN) in Soils and Wastewater Sludge

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Environmental Fate, (Bio)Transformation, and Toxicology of 2,4-Dinitroanisole (DNAN) in Soils and Wastewater Sludge Environmental Fate, (Bio)transformation, and Toxicology of 2,4-dinitroanisole (DNAN) in Soils and Wastewater Sludge Item Type text; Electronic Dissertation Authors Olivares Martinez, Christopher Ignacio Publisher The University of Arizona. Rights Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author. Download date 04/10/2021 03:28:39 Link to Item http://hdl.handle.net/10150/596139 ENVIRONMENTAL FATE, (BIO)TRANSFORMATION, AND TOXICOLOGY OF 2,4-DINITROANISOLE (DNAN) IN SOILS AND WASTEWATER SLUDGE by Christopher I. Olivares Martinez ______________________________________ Copyright © Christopher I. Olivares Martinez 2016 A Dissertation Submitted to the Faculty of the DEPARTMENT OF CHEMICAL AND ENVIRONMENTAL ENGINEERING In Partial Fulfillment of the Requirements For the Degree of DOCTOR OF PHILOSOPHY WITH A MAJOR IN ENVIRONMENTAL ENGINEERING In the Graduate College THE UNIVERSITY OF ARIZONA 2016 THE UNIVERSITY OF ARIZONA GRADUATE COLLEGE As members of the Dissertation Committee, we certify that we have read the dissertation prepared by Christopher I. Olivares Martinez, titled Environmental Fate, (Bio)transformation, and Toxicology of 2,4-dinitroanisole (DNAN) in Soils and Wastewater Sludge and recommend that it be accepted as fulfilling the dissertation requirement for the Degree of Doctor of Philosophy. _______________________________________________________________________ Date: 12/08/2015 Jim A. Field _______________________________________________________________________ Date: 12/08/2015 Reyes Sierra-Alvarez _______________________________________________________________________ Date: 12/08/2015 Robert Arnold _______________________________________________________________________ Date: 12/08/2015 Jon Chorover _______________________________________________________________________ Date: 12/08/2015 Leif Abrell Final approval and acceptance of this dissertation is contingent upon the candidate’s submission of the final copies of the dissertation to the Graduate College. I hereby certify that I have read this dissertation prepared under my direction and recommend that it be accepted as fulfilling the dissertation requirement. ____________________________________________________ Date: 12/08/2015 Dissertation Director: Jim A. Field ____________________________________________________ Date: 12/08/2015 Dissertation Director: Reyes Sierra-Alvarez 2 STATEMENT BY AUTHOR This dissertation has been submitted in partial fulfillment of the requirements for an advanced degree at the University of Arizona and is deposited in the University Library to be made available to borrowers under rules of the Library. Brief quotations from this dissertation are allowable without special permission, provided that an accurate acknowledgement of the source is made. Requests for permission for extended quotation from or reproduction of this manuscript in whole or in part may be granted by the head of the major department or the Dean of the Graduate College when in his or her judgment the proposed use of the material is in the interests of scholarship. In all other instances, however, permission must be obtained from the author. SIGNED: Christopher I. Olivares Martinez 3 ACKNOWLEDGMENTS I would like to thank Dr. Jim A. Field and Dr. Reyes Sierra-Alvarez for all their guidance, encouragement, patience, and trust that has let me grow as a researcher and as a person during these years of doctoral work. I would like to thank Dr. Jon Chorover and Dr. Leif Abrell for their invaluable intellectual support and guidance in this project. I am very grateful to Dr. Robert Arnold for being part of my committee and encouragement. Many thanks to the Superfund Program at the University of Arizona, especially Dr. Raina Maier, Rocío Estrella, Denise Moreno, and Sarah Wilkinson. Being a Superfund Trainee has been a unique and defining experience as a graduate student, in particular for the community engagement and science translation opportunities. I am extremely grateful to Dr. Robert Tanguay and his laboratory at Oregon State University for all the support and encouragement to dive into the world of ecotoxicology during the summer of 2014. Heartfelt thanks to past and current members of the SERDP group from the Chemical Environmental and Soil, Water & Environmental Science departments: Dr. Jidong Liang, Cristina Alvarez-Nieto, Camila Madeira, Dr. Mark Krzmarzick, Dr. David Silva, Sofía Tenorio, Raju Khatiwada, Billy Linker, Dr. Héctor Amezquita, Dr. Stephan Cameron, and Warren Kadoya. This dissertation could not have been completed without the generous support of many institutions: The Mexican Council for Science and Technology (CONACyT), The Strategic Environmental Research and Development Program (SERDP), The University of Arizona Superfund Program, The National Institute of Environmental Health Sciences (NIEHS) KC Donnelly Externship 2014 Award, and The University of Arizona Water Resources Research Center Water Sustainability Graduate Student Fellowship Program. Finally, I would like to deeply thank my family and friends for their encouragement; your smiles, love, and energy everyday encourage me to be the very best I can be. 4 DEDICATION A mi mamá (Ruth) y tía Many, mis hermanas Aranza y Sofía, a mi sobrina Zuley y mis abuelitas Gloria y Trini. que encontremos los electroncitos. 5 TABLE OF CONTENTS LIST OF FIGURES 11 LIST OF TABLES 23 ABSTRACT 25 CHAPTER 1 INTRODUCTION 27 Nitroaromatic explosives as environmental toxicants ..................................27 Insensitive Munitions (IMs) and 2,4-dinitroanisole ......................................27 (Bio)transformation of DNAN ......................................................................29 Nitroreduction ......................................................................................29 Formation of azo-oligomers .................................................................29 Parallel pathways of (bio)transformation.............................................30 (Bio)transformation implications from a similar compound, TNT ..............31 Implications of (bio)transformation to the fate of DNAN ...................31 Toxicity of nitroaromatic compounds and (bio)transformation products .....33 Microbial toxicity of DNAN ................................................................33 Ecotoxicity of DNAN ..........................................................................34 Toxicity of primary (bio)transformation products ...............................35 DNAN and TNT toxicity .....................................................................36 Toxicity implications of (bio)transformation products and mixtures ..36 Assessing toxicity of (bio)transformation mixtures .............................37 CHAPTER 2 MOTIVATION AND RESEARCH QUESTIONS 39 CHAPTER 3 PATHWAYS OF REDUCTIVE 2,4-DINITROANISOLE (DNAN) BIOTRANSFORMATION IN SLUDGE 41 ABSTRACT ...........................................................................................................41 Introduction ...................................................................................................42 Materials and Methods ..................................................................................43 Inocula and Basal Medium ..................................................................43 DNAN Biotransformation Assays .......................................................44 6 Analytical Methods ..............................................................................46 HPLC-DAD ................................................................................46 UHPLC-MS ................................................................................47 TOF-MS ......................................................................................48 Chemicals .............................................................................................48 Results ...........................................................................................................49 DNAN Biotransformation under Aerobic, Microaerophilic, and Anaerobic Conditions .................................................................49 Aerobic Biotransformation .........................................................49 Microaerophilic Biotransformation ............................................52 Anaerobic Biotransformation......................................................54 Comparison of DNAN Conversion Rates under Different Redox Conditions ...................................................................................56 Identification of Anaerobic Biotransformation Products from DNAN with H2 as Cosubstrate ................................................................57 Discussion .....................................................................................................61 Reductive Biotransformation ...............................................................61 Biotransformation Pathways ................................................................63 Reduction of DNAN to Aryl Amines .........................................64 Dimerization of Reduced DNAN Intermediates .........................64 Reduction of Azo Compounds ....................................................65 Methylation and Acetylation Reactions ......................................66 O-demethylation
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