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Biodegradation of Fluorinated Telomer Compounds As a Source of Perfluorinated Acid Formation in the Environment

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Biodegradation of Fluorinated Telomer Compounds As a Source of Perfluorinated Acid Formation in the Environment BIODEGRADATION OF FLUORINATED TELOMER COMPOUNDS AS A SOURCE OF PERFLUORINATED ACID FORMATION IN THE ENVIRONMENT by Mary Joyce Dinglasan-Panlilio A thesis submitted in conformity with the requirements for the degree Doctor of Philosophy Department of Chemistry University of Toronto © Copyright by Mary Joyce Dinglasan-Panlilio, 2008 Library and Bibliotheque et 1*1 Archives Canada Archives Canada Published Heritage Direction du Branch Patrimoine de I'edition 395 Wellington Street 395, rue Wellington Ottawa ON K1A0N4 Ottawa ON K1A0N4 Canada Canada Your file Votre reference ISBN: 978-0-494-39784-8 Our file Notre reference ISBN: 978-0-494-39784-8 NOTICE: AVIS: The author has granted a non­ L'auteur a accorde une licence non exclusive exclusive license allowing Library permettant a la Bibliotheque et Archives and Archives Canada to reproduce, Canada de reproduire, publier, archiver, publish, archive, preserve, conserve, sauvegarder, conserver, transmettre au public communicate to the public by par telecommunication ou par Plntemet, prefer, telecommunication or on the Internet, distribuer et vendre des theses partout dans loan, distribute and sell theses le monde, a des fins commerciales ou autres, worldwide, for commercial or non­ sur support microforme, papier, electronique commercial purposes, in microform, et/ou autres formats. paper, electronic and/or any other formats. The author retains copyright L'auteur conserve la propriete du droit d'auteur ownership and moral rights in et des droits moraux qui protege cette these. this thesis. Neither the thesis Ni la these ni des extraits substantiels de nor substantial extracts from it celle-ci ne doivent etre imprimes ou autrement may be printed or otherwise reproduits sans son autorisation. reproduced without the author's permission. In compliance with the Canadian Conformement a la loi canadienne Privacy Act some supporting sur la protection de la vie privee, forms may have been removed quelques formulaires secondaires from this thesis. ont ete enleves de cette these. While these forms may be included Bien que ces formulaires in the document page count, aient inclus dans la pagination, their removal does not represent il n'y aura aucun contenu manquant. any loss of content from the thesis. Canada Biodegradation of Fluorinated Telomer Compounds as a Source of Perfluorinated Acid Formation in the Environment Doctor of Philosophy Degree 2008 Mary Joyce Dinglasan-Panlilio Department of Chemistry, University of Toronto ABSTRACT The widespread detection of PFCAs in environmental matrices, along with their observed persistence and potential toxicity, has prompted investigation into their sources. The goal of this research was to determine whether biodegradation of various telomer compounds leads to formation of PFCAs and to assess the overall contribution of this class of compounds to the global contamination of PFCAs. The biodegradation of the 8:2 FTOH (CF3(CF2)7CH2CH2OH) was investigated under aerobic conditions in a mixed microbial system. 8:2 FTOH was rapidly degraded forming perfluorooctanoic acid (PFOA) as the terminal metabolite. Other metabolites detected were the 8:2 telomer aldehyde (8:2 FTAL) along with the saturated and unsaturated telomer acids (8:2 FTCA and 8:2 FTUCA). It was proposed that a (3-oxidation type of mechanism maybe involved in the degradation. Investigations into sources of FTOHs to the environment were also pursued. Residual unbound FTOHs in varying chain lengths (C6-C14) were measured in significant amounts from several commercially available and industrially applied fluorinated polymeric and surfactant materials. It was suggested that application of these materials is likely to release these compounds to the environment, which can degrade ultimately leading to PFCA production. Additional sources of FTOH release to the environment were demonstrated from the biodegradation of ester type fluorinated telomer monomers. The telomer alcohol produced from the aerobic degradation of these monomers was observed to further degrade forming previously determined FTOH metabolites including PFOA. A model fluorotelomer acrylate polymer was synthesized and subjected to biodegradation experiments to determine whether they are also potential sources of PFCAs to the environment. The lack of FTOH and PFOA formation from these experiments suggest that these macromolecules are more stable than FTOHs and ester telomer monomers. This research confirms the formation of PFCAs from the biodegradation of telomer alcohols and monomers and suggests that these compounds make an important contribution to the environmental contamination of PFCAs. Future experiments were proposed to better investigate the biodegradation potential of telomer polymers. - in - ACKNOWLEDGEMENTS First and foremost, I would like to acknowledge my primary supervisor, Dr. Scott Mabury, to whom I owe so much. For providing me with that initial spark of interest in research, for showing me the joys and rewards of teaching, and for always inspiring me to raise the bar in everything I do, for all of these I am truly grateful. I aspire to be the great educator and researcher that you are. To my other supervisor, Dr. Elizabeth Edwards, your continued support and guidance have been integral in my years as a graduate student. I would like to acknowledge members of the Mabury Group, past and present. It has been a privilege working with such a talented group of people. Thanks also goes to all the students and alumnus of the Environmental Chemistry program, you have shared in this great adventure. To the soon to be Dr. Nana Kwamena, it has been a joy to collaborate with you. Thank you for your never-ending support and above all, for your friendship. I would never have gotten through these past couple of years without you. Thank you to the administrative and research staff of the Chemistry Department who have helped me along the way. Special thanks to Penny Ashcroft Moore, Dan Mathers, of the ANALEST facility and Alex Young of the AIMS facility. Funding support from National Science and Engineering Research Council and OMNOVA foundation is greatly appreciated. To my entire family, Mom, Dad, Allan and the boys, "Sparky and Philo", you've all shaped who I am today. Thank you for loving me despite my faults and for being proud of what I do. You have instilled in me a great love for education and a passion for learning. Despite all my years studying, it is you who taught me that what matters most is family. - iv - To my husband, Joel, you are my strength. Thank you for following me to Toronto and to our next adventure. This achievement is as much yours as it is mine. Your infinite love, support, patience and understanding are what got me through. You have always made me laugh when I needed it the most and you have always been there with a shoulder to cry on when frustration got to me. I can't wait to start the next chapter of our life together. - v - PREFACE This thesis is organized as a series of manuscripts that have been published, have been submitted to, or in preparation for submission to scientific peer reviewed journals. As a result, some repetition of introductory material and description of methods used in the series of studies is unavoidable. As identified by primary authorship, all manuscripts were prepared by Mary Joyce Dinglasan-Panlilio with critical comments by Elizabeth A. Edwards and Scott A. Mabury. The list of manuscripts along with contributions of authors is outlined below. Chapter I - Biodegradation of Aliphatic Organohalogen Contaminants Chapter II - Fluorotelomer Biodegradation Yields Poly- and Perfluorinated Acids Published in - Environ. Sci. Technol. 2004, 38, 2857-2864 Author list - Mary Joyce A. Dinglasan, Yun Ye, Elizabeth A. Edwards and Scott A Mabury Contributions - Mary Joyce Dinglasan carried out the experimental design and set-up along with gas chromatographic (GC) analysis of volatile analytes of interest. Yun Ye performed liquid chromatography tandem mass spectrometry (LCMSMS) analysis of non-volatile metabolites. Overall data analysis and interpretation was done by Mary Joyce Dinglasan. All versions of the manuscript were prepared by Mary Joyce Dinglasan with critical comments provided by Elizabeth A. Edwards and Scott A. Mabury. Chapter III - Significant Residual Fluorinated Alcohols Present in Various Fluorinated Materials Published in - Environ. Sci. Technol. 2006, 40, 1447-1453 Author list - Mary Joyce A. Dinglasan-Panlilio and Scott A Mabury Contributions — Mary Joyce A. Dinglasan-Panlilio designed and conducted the experiments. All data analysis, interpretation and manuscript preparation were also carried out by Mary Joyce A. Dinglasan-Panlilio. Intellectual input and critical comments were provided by Scott A. Mabury. - vi - Chapter IV - Biodegradation of Fluorotelomer Based Monomers as a Source of Fluorotelomer Alcohols To be submitted to - Environ. Sci. Technol. Author list - Mary Joyce A. Dinglasan, Elizabeth A. Edwards and Scott A Mabury Contributions — Mary Joyce A. Dinglasan-Panlilio designed and conducted all experiments. Data analysis, interpretation and all versions of the manuscript was prepared by Mary Joyce A. Dinglasan-Panlilio. Scott A. Mabury and Elizabeth A. Edwards provided critical comments. Chapter V - Investigation into the Biodegradation of Fluorinated Telomer Polymers Chapter VI - Summary, Conclusions and Future Research Perspectives - vn - Other publication during PhD: MacDonald, M.M., Dinglasan-Panlilio, M.J.A, Mabury, S.A., Solomon, K.R. and Sibley, P.K. Fluorotelomer
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