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Degradation of Hydrazine and Monomethylhydrazine for Fuel Waste Streams Using Alpha-Ketoglutaric Acid

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Degradation of Hydrazine and Monomethylhydrazine for Fuel Waste Streams Using Alpha-Ketoglutaric Acid University of Central Florida STARS Electronic Theses and Dissertations, 2004-2019 2014 Degradation of Hydrazine and Monomethylhydrazine for Fuel Waste Streams using Alpha-ketoglutaric Acid Carolina Franco 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 Franco, Carolina, "Degradation of Hydrazine and Monomethylhydrazine for Fuel Waste Streams using Alpha-ketoglutaric Acid" (2014). Electronic Theses and Dissertations, 2004-2019. 4605. https://stars.library.ucf.edu/etd/4605 DEGRADATION OF HYDRAZINE AND MONOMETHYLHYDRAZINE IN FUEL WASTE STREAMS USING ALPHA-KETOGLUTARIC ACID by CAROLINA FRANCO B.S. University of Central Florida, 2011 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 Science at the University of Central Florida Orlando, Florida Fall Term 2014 Major Professor: Cherie L. Yestrebsky © Carolina Franco 2014 ii ABSTRACT Alpha-ketoglutaric acid (AKGA) is an organic acid important for the metabolism of essential amino acids as well as for the transfer of cellular energy. It is a precursor of glutamic acid which is produced by the human body during the Krebs Cycle. AKGA has a specific industrial interest as it can be taken as a dietary supplement and is also widely used as a building block in chemical synthesis. Collectively termed as hydrazine (HZs), hydrazine (HZ) and monomethylhydrazine (MMH) are hypergolic fuels that do not need an ignition source to burn. Because of the particular HZs’ characteristics the National Aeronautics and Space Administration (NASA) at Kennedy Space Center (KSC) and the US Air Force at Cape Canaveral Air Force Station (CCAFS) consistently use HZ and MMH as hypergolic propellants. These propellants are highly reactive and toxic, and have carcinogenic properties. The handling, transport, and disposal of HZ waste are strictly regulated under the Resource Conservation and Recovery Act (RCRA) to protect human health and the environment. Significant quantities of wastewater containing residuals of HZ and MMH are generated at KSC and CCAFS that are subsequently disposed off-site as hazardous waste. This hazardous waste is shipped for disposal over public highways, which presents a potential threat to the public and the environment in the event of an accidental discharge in transit. NASA became aware of research done using AKGA to neutralize HZ waste. This research indicated that AKGA transformed HZ in an irreversible reaction potentially leading to the disposal of the hypergols via the wastewater treatment facility located at CCAFS eliminating the need to transport most of the HZ waste off-site. New Mexico Highlands University (NMHU) has researched this transformation of HZ by reaction with AKGA to form stabilized pyridazine derivatives. NMHU’s research suggests that the treatment of HZ and MMH using AKGA is an irreversible reaction; once the reaction takes place, HZ and/or MMH cannot re-form from the byproducts obtained. However, further knowledge relating to the iii ultimate end products of the reaction, and their effects on human health and the environment, must still be addressed. The known byproduct of the AKGA/HZ neutralization reaction is 6-oxo-1,4,5,6-tetrahydro- pyridazine-3-carboxylic acid (PCA), and the byproduct of the AKGA/MMH reaction is 1-methyl-6-oxo- 4,5-dihydro-pyridazine-3-carboxylic acid (mPCA). This research addressed several primary areas of interest to further the potential use of AKGA for HZ and MMH neutralization: 1) isolation of the end-product of the MMH-AKGA degradation process, 1- methyl-6-oxo-4,5-dihydro-pyridazine-3-carboxylic acid (mPCA), and determination of several physical properties of this substance, 2) evaluation of the kinetics of the reaction of AKGA with HZ or MMH, 3) verification of the chemical mechanism for the reaction of the individual hypergols with AKGA, 4) determination of whether the addition of a silicone-based antifoaming agent (AF), citric acid (CA) and/or isopropyl alcohol (IPA) to the AKGA and HZ or MMH solution interferes with the degradation reaction, 4) application of laboratory bench scale experiments in field samples, and 5) determination of the reaction enthalpy of these reactions. iv DEDICATION All the efforts of these years of work are especially dedicated to my little Valeria. Daughter, thanks for your unconditional love, for always being there with a smile, a kiss, and a hug when I needed it the most. Thanks for teaching me to be a better person, and mostly a better mom. This was not an easy journey but you helped me achieving this important step in our lives. Always remember, who perseveres conquers; never give up your dreams. You are the reason for everything I do! I love you with all my heart. v ACKNOWLEDGMENTS I would like to thank the URS team and Chuck Davis from NASA for providing me with the opportunity to do this research that has truly expanded my knowledge of science. Without their trust and funding, this dissertation would never have come true. Thanks to Rodolfo Martinez and David Glass from New Mexico Highlands University for all their support. I also have an special gratitude to Steve Cobert from URS-Orlando who allowed me to demonstrate and apply the the knowledge I gained during these years of research. Moreover, I am infinitely thankful to my primary advisor Dr. Cherie Yestrebsky for believing in me and giving me the opportunity to prove what I am capable of. Thanks to her guidance, patience, trust and support I was able to work hard and come this far in my academic career. I would like to also thank my committee members: Dr. Christian Clausen, Dr. Steven Duranceau, Dr. Matthew Rex, and Dr. James Harper for their guidance and support. Last but most important, thanks to my dad, mom, and sisters for their unconditional love. You were always there when I needed; you pushed me to give the best of me and never give up. Papi THANKS! I would never be able to come this far without your help. vi TABLE OF CONTENTS LIST OF FIGURES ...................................................................................................................................... x LIST OF TABLES ..................................................................................................................................... xvi LIST OF EQUATIONS ........................................................................................................................... xviii HYPOTHESIS .............................................................................................................................................. 1 EXPERIMENTAL METHODS .................................................................................................................... 2 CHAPTER 1: INTRODUCTION ................................................................................................................. 5 1.1 Chemical Structure and Physical Properties of HZ, MMH, and AKGA ...................................... 5 1.1.1 HZs ............................................................................................................................................... 5 1.1.2 AKGA .......................................................................................................................................... 6 1.2 History of HZ and Current Applications ....................................................................................... 7 1.3 Hazards of HZ and Its Exposure Limits ........................................................................................ 9 1.4 Environmental Release ............................................................................................................... 11 1.5 Environmental Fate ..................................................................................................................... 12 1.5.1 Air .............................................................................................................................................. 12 1.5.2 Water .......................................................................................................................................... 12 1.5.3 Soil and Sediment ...................................................................................................................... 13 1.6 Remediation Techniques ............................................................................................................. 13 1.7 Suggested Remediation Technique ............................................................................................. 17 1.8 Research Objectives .................................................................................................................... 18 CHAPTER 2: MPCA ISOLATION AND CHARACTERIZATION ......................................................... 20 2.1 Introduction ....................................................................................................................................... 20 2.2 Experimental Procedure .................................................................................................................... 20 2.3 Results
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