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Application of Liquid Chromatography-Mass Spectrometry for the Analysis of Endocrine Disrupting Chemical Transformation Products in Advanced Oxidation Processes and Their Reaction Mechanisms

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Handbook of Environmental Materials Management

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Abstract

Advanced oxidation processes (AOPs) have gained a great deal of attention as they held great promise for the treatment of wastewater contaminated with noneasily removable organic pollutants. The assessment of transformation products allowed the overall efficiency of AOPs to be better understood since some transformation products possessed higher toxicity than the mother compounds. Liquid chromatography coupled to mass spectrometry has been heavily used as an analytical tool in the environmental field as it allowed the best performance in assigning the identity of the transformation products detected. This chapter reviews liquid chromatography-mass spectrometry for the identification of endocrine disrupting chemical (EDC) transformation products formed from several AOPs such as photolysis, photocatalysis, sonolysis, and Fenton treatment. EDCs are a group of special interest due to their ability to exert hormonal imbalance activity and consequently caused adverse health effects in an organism or its progeny. Data concerning to the mechanism of AOP-mediated reactions on the EDCs degradation are also discussed in this chapter. Finally, the future prospects of AOPs on EDCs degradation are summarized and discussed.

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References

  • Acero JL, Benitez FJ, Real FJ, Roldan G (2010) Kinetics of aqueous chlorination of some pharmaceuticals and their elimination from water matrices. Water Res 44:4158–4170

    Article  Google Scholar 

  • Al-Hamdi AM, Sillanpää M, Bora T, Dutta J (2016) Efficient photocatalytic degradation of phenol in aqueous solution by SnO2:Sb nanoparticles. Appl Surf Sci 370:229–236

    Article  Google Scholar 

  • Al-Rifai JH, Khabbaz H, Schäfer AI (2011) Removal of pharmaceuticals and endocrine disrupting compounds in a water recycling process using reverse osmosis systems. Sep Purif Technol 77:60–67

    Article  Google Scholar 

  • Avasarala BK, Tirukkovalluri SR, Bojja S (2011) Photocatalytic degradation of monocrotophos pesticide – an endocrine disruptor by magnesium doped titania. J Hazard Mater 186:1234–1240

    Article  Google Scholar 

  • Ayoub K, Hullebusch EDV, Cassir M, Bermond A (2010) Application of advanced oxidation processes for TNT removal: a review. J Hazard Mater 178:10–28

    Article  Google Scholar 

  • Ba-Abbad MM, Takriff MS, Kadhum AAH, Mohamad AB, Benamor A, Mohammad AW (2017) Solar photocatalytic degradation of 2-chlorophenol with ZnO nanoparticles: optimisation with D-optimal design and study of intermediate mechanisms. Environ Sci Pollut Res 24:2804–2819

    Article  Google Scholar 

  • Bagal MV, Gogate PR (2012) Sonochemical degradation of alachlor in the presence of process intensifying additives. Sep Purif Technol 90:92–100

    Article  Google Scholar 

  • Burkhardt-Holm P (2010) Endocrine disruptors and water quality: a state-of-the-art review. Int J Water Resour Dev 26:477–493

    Article  Google Scholar 

  • Caliman FA, Gavrilescu M (2009) Pharmaceuticals, personal care products and endocrine disrupting agents in the environment – a review. Clean-Soil Air Water 37:277–303

    Article  Google Scholar 

  • Chen XJ, Dai YZ, Wang XY (2015) Methods and mechanism for improvement of photocatalytic activity and stability of Ag3PO4: a review. J Alloys Compd 649:910–932

    Article  Google Scholar 

  • Chowdhury P, Viraraghavan T (2009) Sonochemical degradation of chlorinated organic compounds, phenolic compounds and organic dyes – a review. Sci Total Environ 407:2474–2492

    Article  Google Scholar 

  • Dai F, Fan XR, Stratton GR, Bellona CL, Holsen TM, Crimmins BS, Xia XY, Thagard SM (2016) Experimental and density functional theoretical study of the effects of Fenton’s reaction on the degradation of Bisphenol A in a high voltage plasma reactor. J Hazard Mater 308:419–429

    Article  Google Scholar 

  • Dang TTT, Le STT, Channei D, Khanitchaidecha W, Nakaruk A (2016) Photodegradation mechanisms of phenol in the photocatalytic process. Res Chem Intermed 42:5961–5974

    Article  Google Scholar 

  • Eertmans F, Dhooge W, Stuyvaert S, Comhaire F (2003) Endocrine disruptors: effects on male fertility and screening tools for their assessment. Toxicol In Vitro 17:515–524

    Article  Google Scholar 

  • Entezari MH, Pétrier C, Devidal P (2003) Sonochemical degradation of phenol in water: a comparison of classical equipment with a new cylindrical reactor. Ultrason Sonochem 10:103–108

    Article  Google Scholar 

  • Eslami A, Bahrami H, Asadi A, Alinejad A (2016) Enhanced sonochemical degradation of tetracycline by sulfate radicals. Water Sci Technol 73:1293–1300

    Google Scholar 

  • Esplugas S, Bila DM, Krause LGT, Dezotti M (2007) Ozonation and advanced oxidation technologies to remove endocrine disrupting chemicals (EDCs) and pharmaceuticals and personal care products (PPCPs) in water effluents. J Hazard Mater 149:631–642

    Article  Google Scholar 

  • Golash N, Gogate PR (2012) Degradation of dichlorvos containing wastewaters using sonochemical reactors. Ultrason Sonochem 19:1051–1060

    Article  Google Scholar 

  • Gu L, Song FY, Zhu NW (2011) An innovative electrochemical degradation of 1-diazo-2-naphthol-4-sulfonic acid in the presence of Bi2Fe4O9. Appl Catal B Environ 110:186–194

    Article  Google Scholar 

  • Guo CS, Gao SW, Lv JP, Hou S, Zhang Y, Xu J (2017) Assessing the photocatalytic transformation of norfloxacin by BiOBr/iron oxides hybrid photocatalyst: kinetics, intermediates, and influencing factors. Appl Catal B Environ 205:68–77

    Article  Google Scholar 

  • Huang WY, Luo MQ, Wei CS, Wang YH, Hanna K, Mailhot G (2017) Enhanced heterogeneous photo-Fenton process modified by magnetite and EDDS: BPA degradation. Environ Sci Pollut Res 24:10421–10429

    Article  Google Scholar 

  • Ifelebuegu AO, Onubogu J, Joyce E, Mason T (2014) Sonochemical degradation of endocrine disrupting chemicals 17β-estradiol and 17α-ethinylestradiol in water and wastewater. Int J Environ Sci Technol 11:1–8

    Article  Google Scholar 

  • Jiao SJ, Zheng SR, Yin DQ, Wang LH, Chen LY (2008) Aqueous photolysis of tetracycline and toxicity of photolytic products to luminescent bacteria. Chemosphere 73:377–382

    Article  Google Scholar 

  • Khataee A, Gholami P, Sheydaei M (2016) Heterogeneous Fenton process by natural pyrite for removal of a textile dye from water: effect of parameters and intermediate identification. J Taiwan Inst Chem Eng 58:366–373

    Article  Google Scholar 

  • Kondrakov AO, Ignatev AN, Frimmel FH, Bräse S, Horn H, Revelsky AL (2014) Formation of genotoxic quinones during bisphenol A degradation by TiO2 photocatalysis and UV photolysis: a comparative study. Appl Catal B Environ 160–161:106–114

    Article  Google Scholar 

  • Laganà A, Bacaloni A, De Leva I, Faberi A, Fago G, Marino A (2004) Analytical methodologies for determining the occurrence of endocrine disrupting chemicals in sewage treatment plants and natural waters. Anal Chim Acta 501:79–88

    Article  Google Scholar 

  • Lam SM, Sin JC, Abdullah AZ, Mohamed AR (2013) Photocatalytic degradation of resorcinol, an endocrine disrupter, by TiO2 and ZnO suspensions. Environ Technol 34:1097–1106

    Article  Google Scholar 

  • Lam SM, Sin JC, Mohamed AR (2016) A review on photocatalytic application of g-C3N4/semiconductor (CNS) nanocomposites towards the erasure of dyeing wastewater. Mater Sci Semicond Process 47:62–84

    Article  Google Scholar 

  • Lau TK, Chu W, Graham N (2007) Reaction pathways and kinetics of butylated hydroxyanisole with UV, ozonation, and UV/O3 processes. Water Res 41:765–774

    Article  Google Scholar 

  • Lesko T, Colussi AJ, Hoffmann MR (2006) Sonochemical decomposition of phenol: evidence for a synergistic effect of ozone and ultrasound for the elimination of total organic carbon from water. Environ Sci Technol 40:6818–6823

    Article  Google Scholar 

  • Liu ZH, Kanjo Y, Mizutani S (2009) Removal mechanisms for endocrine disrupting compounds (EDCs) in wastewater treatment – physical means, biodegradation, and chemical advanced oxidation: a review. Sci Total Environ 407:731–748

    Article  Google Scholar 

  • Liu YQ, He XX, Fu YS, Dionysiou DD (2016) Degradation kinetics and mechanism of oxytetracycline by hydroxyl radical-based advanced oxidation processes. Chem Eng J 284:1317–1327

    Article  Google Scholar 

  • López-Muñoz MJ, Revilla A, Aguado J (2013) Heterogeneous photocatalytic degradation of isoproturon in aqueous solution: experimental design and intermediate products analysis. Catal Today 209:99–107

    Article  Google Scholar 

  • Marković M, Jović M, Stanković D, Kovačević V, Roglić G, Gojgić-Cvijović G, Manojlović D (2015) Application of non-thermal plasma reactor and Fenton reaction for degradation of ibuprofen. Sci Total Environ 505:1148–1155

    Article  Google Scholar 

  • Medana C, Calza P, Baiocchi C, Pelizzetti E (2005) Liquid chromatography tandem mass spectrometry as a tool to investigate pesticides and their degradation products. Curr Org Chem 9:859–873

    Article  Google Scholar 

  • Mena E, Rey A, Rodríguez EM, Beltrán FJ (2017) Reaction mechanism and kinetics of DEET visible light assisted photocatalytic ozonation with WO3 catalyst. Appl Catal B Environ 202:460–472

    Article  Google Scholar 

  • Mennigen JA, Zamora JM, Chang JP, Trudeau VL (2017) Endocrine disrupting effects of waterborne fluoxetine exposure on the reproductive axis of female goldfish, Carassius auratus. Comp Biochem Physiol C: Toxicol Pharmacol 202:70–78

    Google Scholar 

  • Moon BR, Kim TK, Kim MK, Choi JW, Zoh KD (2017) Degradation mechanisms of Microcystin-LR during UV-B photolysis and UV/H2O2 processes: byproducts and pathways. Chemosphere 185:1039–1047

    Article  Google Scholar 

  • Papadopoulos C, Frontistis Z, Antonopoulou M, Venieri D, Konstantinou I, Mantzavinos D (2016) Sonochemical degradation of ethyl paraben in environmental samples: statistically important parameters determining kinetics, by-products and pathways. Ultrason Sonochem 31:62–70

    Article  Google Scholar 

  • Park JS, Her NG, Yoon YM (2011) Sonochemical degradation of chlorinated phenolic compounds in water: effects of physicochemical properties of the compounds on degradation. Water Air Soil Pollut 215:585–593

    Article  Google Scholar 

  • Patil AB, Patil KR, Pardeshi SK (2010) Ecofriendly synthesis and solar photocatalytic activity of S-doped ZnO. J Hazard Mater 183:315–323

    Article  Google Scholar 

  • Peller J, Wiest O, Kamat PV (2001) Sonolysis of 2,4-dichlorophenoxyacetic acid in aqueous solutions. Evidence for •OH radical-mediated degradation. J Phys Chem A 105:3176–3181

    Article  Google Scholar 

  • Qiang ZM, Dong HY, Zhu B, Qu JH, Nie YF (2013) A comparison of various rural wastewater treatment processes for the removal of endocrine-disrupting chemicals (EDCs). Chemosphere 92:986–992

    Article  Google Scholar 

  • Romero V, González O, Bayarri B, Marco P, Giménez J, Esplugas S (2016) Degradation of Metoprolol by photo-Fenton: comparison of different photoreactors performance. Chem Eng J 283:639–648

    Article  Google Scholar 

  • Salma A, Thoröe-Boveleth S, Schmidt TC, Tuerk J (2016) Dependence of transformation product formation on pH during photolytic and photocatalytic degradation of ciprofloxacin. J Hazard Mater 313:49–59

    Article  Google Scholar 

  • Sasi S, Rayaroth MP, Devadasan D, Aravind UK, Aravindakumar CT (2015) Influence of inorganic ions and selected emerging contaminants on the degradation of methylparaben: a sonochemical approach. J Hazard Mater 300:202–209

    Article  Google Scholar 

  • Shen JH, Horng JJ, Wang YS, Zeng YR (2017) The use of reactive index of hydroxyl radicals to investigate the degradation of acid orange 7 by Fenton process. Chemosphere 182:364–372

    Article  Google Scholar 

  • Simsek EB (2017) Solvothermal synthesized boron doped TiO2 catalysts: photocatalytic degradation of endocrine disrupting compounds and pharmaceuticals under visible light irradiation. Appl Catal B Environ 200:309–322

    Article  Google Scholar 

  • Sin JC, Lam SM, Mohamed AR, Lee KT (2012) Degrading endocrine disrupting chemicals from wastewater by TiO2 photocatalysis: a review. Int J Photoenergy 2012:185159

    Article  Google Scholar 

  • Sin JC, Lam SM, Lee KT, Mohamed AR (2013) Self-assembly fabrication of ZnO hierarchical micro/nanospheres for enhanced photocatalytic degradation of endocrine-disrupting chemicals. Mater Sci Semicond Process 16:1542–1550

    Article  Google Scholar 

  • Sin JC, Lam SM, Satoshi I, Lee KT, Mohamed AR (2014) Sunlight photocatalytic activity enhancement and mechanism of novel europium-doped ZnO hierarchical micro/nanospheres for degradation of phenol. Appl Catal B Environ 148–149:258–268

    Article  Google Scholar 

  • Sirtori C, Agüera A, Carra I, Sanchéz-Pérez JA (2014) Identification and monitoring of thiabendazole transformation products in water during Fenton degradation by LC-QTOF-MS. Anal Bioanal Chem 406:5323–5337

    Article  Google Scholar 

  • Skinner MK, Manikkam M, Guerrero-Bosagna C (2011) Epigenetic transgenerational actions of endocrine disruptors. Reprod Toxicol 31:337–343

    Article  Google Scholar 

  • Souissi Y, Bourcier S, Bouchonnet S, Genty C, Sablier M (2012) Estrone direct photolysis: by-product identification using LC-Q-TOF. Chemosphere 87:185–193

    Article  Google Scholar 

  • Stalter D, Magdeburg A, Wagner M, Oehlmann J (2011) Ozonation and activated carbon treatment of sewage effluents: removal of endocrine activity and cytotoxicity. Water Res 45:1015–1024

    Article  Google Scholar 

  • Tay KS, Rahman NA, Abas MRB (2011) Fenton degradation of dialkylphthalates: products and mechanism. Environ Chem Lett 9:539–546

    Article  Google Scholar 

  • Torres RA, Abdelmalek F, Combet E, Pétrier C, Pulgarin C (2007) A comparative study of ultrasonic cavitation and Fenton’s reagent for bisphenol A degradation in deionised and natural waters. J Hazard Mater 146:546–551

    Article  Google Scholar 

  • Torres RA, Pétrier C, Combet E, Carrier M, Pulgarin C (2008) Ultrasonic cavitation applied to the treatment of bisphenol A. Effect of sonochemical parameters and analysis of BPA by-products. Ultrason Sonochem 15:605–611

    Article  Google Scholar 

  • Tran N, Drogui P, Zaviska F, Brar SK (2013) Sonochemical degradation of the persistent pharmaceutical carbamazepine. J Environ Manag 131:25–32

    Article  Google Scholar 

  • Trovó AG, Nogueira RFP, Agüera A, Fernandez-Alba AR, Malato S (2011) Degradation of the antibiotic amoxicillin by photo-Fenton process – chemical and toxicological assessment. Water Res 45:1394–1402

    Article  Google Scholar 

  • Vallejo M, Román MFS, Ortiz I, Irabien A (2015) Overview of the PCDD/Fs degradation potential and formation risk in the application of advanced oxidation processes (AOPs) to wastewater treatment. Chemosphere 118:44–56

    Article  Google Scholar 

  • Wang FL, Chen P, Feng YP, Xie ZJ, Liu Y, Su YH, Zhang QX, Wang YF, Yao K, Lv WY, Liu GG (2017) Facile synthesis of N-doped carbon dots/g-C3N4 photocatalyst with enhanced visible-light photocatalytic activity for the degradation of indomethacin. Appl Catal B Environ 207:103–113

    Article  Google Scholar 

  • Weber AS, Grady AM, Koodali RT (2012) Lanthanide modified semiconductor photocatalysts. Cat Sci Technol 2:683–693

    Article  Google Scholar 

  • Weidauer C, Davis C, Raeke J, Seiwert B, Reemtsma T (2016) Sunlight photolysis of benzotriazoles–identification of transformation products and pathways. Chemosphere 154:416–424

    Article  Google Scholar 

  • Wongniramaikul W, Liao CH, Kanatharana P (2007) Diisobutyl phthalate degradation by Fenton treatment. J Environ Sci Heal A 42:567–572

    Article  Google Scholar 

  • Zhang A, Li YM (2014) Removal of phenolic endocrine disrupting compounds from waste activated sludge using UV, H2O2, and UV/H2O2 oxidation processes: effects of reaction conditions and sludge matrix. Sci Total Environ 493:307–323

    Article  Google Scholar 

  • Zhang J, Sun B, Guan XH (2013) Oxidative removal of bisphenol A by permanganate: kinetics, pathways and influences of co-existing chemicals. Sep Purif Technol 107:48–53

    Article  Google Scholar 

  • Zhou KF, Xie XD, Chang CT (2017) Photocatalytic degradation of tetracycline by Ti-MCM-41 prepared at room temperature and biotoxicity of degradation products. Appl Surf Sci 416:248–258

    Article  Google Scholar 

  • Zhu NW, Gu L, Yuan HP, Lou ZY, Wang L, Zhang X (2012) Degradation pathway of the naphthalene azo dye intermediate 1-diazo-2- naphthol-4-sulfonic acid using Fenton’s reagent. Water Res 46:3859–3867

    Article  Google Scholar 

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Acknowledgments

This work was supported by the Universiti Tunku Abdul Rahman (UTARRF/2016–C2/S03 and UTARRF/2017-C1/L02) and Ministry of Higher Education of Malaysia (FRGS/1/2015/TK02/UTAR/02/2 and FRGS/1/2016/TK02/UTAR/02/1).

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Authors and Affiliations

  1. Department of Petrochemical Engineering, Faculty of Engineering and Green Technology, Universiti Tunku Abdul Rahman, Kampar, Perak, Malaysia

    Jin-Chung Sin

  2. Department of Environmental Engineering, Faculty of Engineering and Green Technology, Universiti Tunku Abdul Rahman, Kampar, Perak, Malaysia

    Sze-Mun Lam

  3. School of Chemical Engineering, Universiti Sains Malayisia, Engineering Campus, Nibong Tebal, Pulau Pinang, Malaysia

    Abdul Rahman Mohamed

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  1. Jin-Chung Sin
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  2. Sze-Mun Lam
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  3. Abdul Rahman Mohamed
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Correspondence to Jin-Chung Sin .

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Editors and Affiliations

  1. Dept. of Chemistry and EVSC, New Jersey InstTech, 151 D Tiernan-NJIT Dept. of Chemistry and EVSC, Newark, New Jersey, USA

    Chaudhery Mustansar Hussain

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  1. Department of Chemistry and Environmental Sciences, New Jersey Institute of Technology, Newark, NJ, USA

    Chaudhery Mustansar Hussain

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Sin, JC., Lam, SM., Mohamed, A.R. (2018). Application of Liquid Chromatography-Mass Spectrometry for the Analysis of Endocrine Disrupting Chemical Transformation Products in Advanced Oxidation Processes and Their Reaction Mechanisms. In: Hussain, C. (eds) Handbook of Environmental Materials Management. Springer, Cham. https://doi.org/10.1007/978-3-319-58538-3_90-1

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  • DOI: https://doi.org/10.1007/978-3-319-58538-3_90-1

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  • Print ISBN: 978-3-319-58538-3

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