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Reaction Pathways in the Chlorination of Amino Acids

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Reaction Pathways in the Chlorination of Amino Acids Department of Chemistry Reaction Pathways in the Chlorination of Amino Acids Zuo Tong How This thesis is presented for the Degree of Doctor of Philosophy Of Curtin University June 2016 Declaration To the best of my knowledge and belief this thesis contains no material previously published by any other person except where due acknowledgment has been made. This thesis contains no material which has been accepted for the award of any other degree or diploma in any university. Signature: ____________ Zuo Tong How Date: 30/06/2016 Acknowledgments I am very grateful to many individuals for the help and support that I’ve received over the past years. Especially to the following people: My Principal Supervisor, A/Prof. Cynthia Joll, for her continual guidance and insights for the project; for her support and encouragement; and for her thorough review of this Thesis. My Co-Supervisor, Dr. Kathryn Linge, for her guidance and encouragement throughout my PhD program; for her advice on experimental planning and design; and her insightful feedback on this Thesis. My Co-Supervisor, Dr. Francesco Busetti, for his helpful insight and technical advice on LC-MS; for his contribution to experimental planning and design; and his helpful feedback on the Thesis. Mr. Geoff Chidlow, for his invaluable technical assistance and advice on the operation of GC-MS instrumentation. The staff and my fellow students in the Department of Chemistry, past and present, for their support, assistance and companionship over the years, particularly Ina Kristiana, Deborah Liew, Jace Tan, Mark Maric, Patrick Fritz, Krishnan Murugappan and Rhys Tilbury. The staff of the Water Corporation of Western Australia, for assistance in the provision of samples and operational information for my project. Ms. Carolyn Bellamy and Mr. Gareth Roeszler from Water Research Australia for their wonderful support and encouragement throughout the course of my project. My Water Research Australia mentor, Ms. Mary Drikas, for her invaluable advice and insight for my project. i I would also like to acknowledge the following institutions for financial support: Curtin University (Curtin International Postgraduate Research Scholarship) and Water Research Australia (WaterRA PhD Top-Up Scholarship). I also thank the Australian Research Council (LP110100548 and LP130100602) and the Water Corporation of Western Australia for their support of this project. Last, but not least, I would like to thank my family and friends for their support, understanding and encouragement throughout the years. Special thanks to Michelle Wong for encouraging me to apply for the PhD program, as all this would not be possible without taking that first step. ii Abstract Water disinfection is a crucial step in the production of safe drinking water. In water disinfection, pathogenic microorganisms are removed or deactivated by means of physical or chemical methods. Chlorination and chloramination are the most widely used disinfection techniques as they are effective, inexpensive, and provide disinfectant residual within the distribution system for a considerable length of time. When chlorination and chloramination are used, the disinfectant is measured as free or combined chlorine. Although combined chlorine is used as the measurement for inorganic monochloramine, combined chlorine in fact includes all species of inorganic and organic chloramines. Organic chloramines are compounds that contain at least one chlorine atom directly bonded to an amine nitrogen atom in an organic molecule. In water chemistry, organic chloramines can also be used as a collective term for species like N-chloramines, N-chloramino acids, N-chloraldimines and N-chloramides, due to the fact that these species are included in the measurement of combined chlorine. Organic chloramines are known to form when chlorine-based disinfectants react with dissolved organic nitrogen or dissolved organic carbon, however minimal information on the occurrence of organic chloramines in drinking water is available, resulting in unknown health risks. In vitro studies and structural assessment of the toxicity of organic chloramines suggest that organic chloramines are potential carcinogens and mutagens. The formation of organic chloramines can also cause adverse effects in water treatment. The formation of organic chloramines has been found to increase the chlorine demand of treated water, and reduce germicidal efficiency of both chlorine and inorganic monochloramine. Most importantly, organic chloramines interfere in all analytical methods used to determine combined chlorine residuals, which can result in the overestimation of inorganic monochloramine concentrations in disinfected waters. In addition, N-chloramino acids are known to degrade into odorous aldehydes and N-chloraldimines, which could potentially result in odour issues in drinking water. This Thesis focuses on better understanding the reaction of amino acids with chlorine, the reaction thought to be the main contributor to the formation of organic chloramines. Chapter 2 presents a critical review of previously published information on the iii formation of organic chloramines and their impact on water treatment processes. The development of analytical methods for amino acids and organic chloramines is presented in Chapter 3. In Chapter 4, studies of the formation and stability of organic chloramines are reported, while the speciation and degradation of organic chloramines, specifically N-chloramino acids, are described in Chapter 5. Finally, the occurrence of free amino acids and the odorous degradation products of N-chloramino acids in both drinking waters and wastewaters is presented in Chapter 6. The conclusions and recommendations of this Thesis are summarised in Chapter 7. The critical review on organic chloramines presented in Chapter 2 highlighted that one of the biggest challenges for the study of organic chloramines in water systems was the absence of analytical standards, resulting in difficulties in the identification and quantification of organic chloramines in water systems. In addition, many of the organic chloramines formed during disinfection were found to be unstable, which resulted in difficulties in sampling and detection using mass spectrometric methods. The review also indicated that the formation of organic monochloramines and dichloramines should be considered during water disinfection, as it is a common strategy to achieve breakpoint chlorination during disinfection. The practice of breakpoint chlorination involves a high chlorine to precursor molar ratio, making it more likely that organic dichloramines would be formed. Finally, the review found that organic chloramines can be formed from many different precursors and pathways. Therefore, by understanding the occurrence and concentrations of the precursors in water systems, better prediction of the formation of organic chloramines can be achieved. Analytical methods developed for the analysis of amino acids and to monitor the degradation of organic chloramines are presented in Chapter 3. A novel analytical method for the analysis of 18 amino acids in natural waters, which utilised solid-phase extraction (SPE) for sample clean-up and extraction, followed by liquid chromatography-electrospray tandem mass spectrometry (LC-MS/MS) operated in multiple reaction monitoring mode, was developed and validated. The method limits of quantification (MLQ) for the SPE LC-MS/MS method in ultrapure water ranged from 0.1 to 100 µg L-1 as N for the different amino acids. The developed method was successfully applied for the analysis of free amino acids in three surface waters and iv was used in Chapter 4 for the analysis of residual amino acids after chlorination and for the survey of free amino acids in drinking waters and wastewaters in Chapter 6. To study the formation and degradation of organic chloramines, a direct UV method and a modified standard iodometric method for colorimetric measurement were used. The modified standard iodometric method was only used for organic chloramines not suitable for direct UV detection due to interference peaks in the 250 to 280 nm range from either the precursors of the organic chloramines or from the degradation products of the organic chloramines. The combination of direct UV detection and the modified standard iodometric method allowed the stability of more organic chloramines to be investigated than in previous studies. This research is presented in Chapter 4. The formation and stability of organic chloramines, from chlorination of three amines and 21 amino acids, and organic chloramides from two amides, and the competition between 20 of the amino acids (the proteinogenic amino acids) during chlorination, were studied and the results presented in Chapter 4. After chlorination at a chlorine to precursor (amine, amino acid or amide) molar ratio of 0.2 to 2, all three amines and 18 out of the 21 amino acids formed organic chloramines, while the amides and three amino acids (cysteine, methionine and tryptophan) did not form organic chloramides/chloramines. These three amino acids did not form organic chloramines at these low molar ratios because they have a second functional group which is more reactive to chlorine than the amine group. Among the 20 proteinogenic amino acids tested for their competitive reactivity towards chlorination, cysteine, methionine and tryptophan were the most reactive amino acids towards chlorination, however they did not form organic chloramines at the chlorine to precursor ratios
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