Aqueous chlorination of acebutolol: kinetics, transformation by-products, and mechanism

详细信息    查看全文

• 作者：Wan Nor Adira Wan Khalit ; Kheng Soo Tay
• 关键词：Beta ; blockers ; Chlorination ; Water treatment ; Degradation by ; products ; Pharmaceuticals ; QTOF
• 刊名：Environmental Science and Pollution Research
• 出版年：2016
• 出版时间：February 2016
• 年：2016
• 卷：23
• 期：3
• 页码：2521-2529
• 全文大小：783 KB
• 参考文献：Abia L, Armesto XL, Canle ML, Garcia MV, Santaballa JA (1998) Oxidation of aliphatic amines by aqueous chlorine. Tetrahedron 54:521–530CrossRef
  Acero JL, Benitez FJ, Real FJ, Roldan G (2010) Kinetics of aqueous chlorination of some pharmaceuticals and their elimination from water matrices. Water Res 44:4158–4170CrossRef
  Adam LC, Gordon G (1995) Direct and sequential potentiometric determination of hypochlorite, chlorite, and chlorate ions when hypochlorite ion is present in large excess. Anal Chem 67:535–540CrossRef
  Babic S, Horvat AJM, Pavlovic DM, Macan MK (2007) Determination of pKa values of active pharmaceutical ingredients. Trends Anal Chem 26:1043–1061CrossRef
  Bedner M, MacCrehan WA (2006) Reactions of the amine-containing drugs fluoxetine and metoprolol during chlorination and dechlorination processes used in wastewater treatment. Chemosphere 65:2130–2137CrossRef
  Cai MQ, Feng L, Jiang J, Qi F, Zhang LQ (2013) Reaction kinetics and transformation of antipyrine chlorination with free chlorine. Water Res 47:2830–2842CrossRef
  Chamberlain E, Adams C (2006) Oxidation of sulfonamides, macrolides, and carbadox with free chlorine and monochloramine. Water Res 40:2517–2526CrossRef
  Daneshvar A, Svanfelt J, Kronberg L, Prѐvost M, Weyhenmeyer GA (2010) Seasonal variations in the occurrence and fate of basic and neutral pharmaceuticals in a Swedish river-lake system. Chemosphere 80:301–309CrossRef
  Deborde M, Gunten UV (2008) Reactions of chlorine with inorganic and organic compounds during water treatment-Kinetics and mechanism: a critical review. Water Res 42:13–51CrossRef
  Dodd MC, Shah AD, Gunten UV, Huang CH (2005) Interactions of fluoroquinolone antibacterial agents with aqueous chlorine: reaction kinetics, mechanism, and transformation pathways. Environ Sci Technol 39:7065–7076CrossRef
  El Najjar NM, Deboede M, Journel R, Vel Leitner NK (2013) Aqueous chlorination of levofloxacin: kinetics and mechanistic study, transformation product identification and toxicity. Water Res 47:121–129CrossRef
  Gabet-Giraud V, Miege C, Choubert JM, Ruel SM, Coquery M (2010) Occurrence and removal of estrogens and beta blockers by various wastewater treatment plants. Sci Total Environ 408:4257–4269CrossRef
  Gabet-Giraud V, Miege Jacquet R, Coquery M (2014) Impact of wastewater treatment plants on receiving surface waters and a tentative risk evaluation: the case of estrogens and beta blockers. Environ Sci Pollut Res 21:1708–1722CrossRef
  Gallard H, Gunten UV (2002) Chlorination of phenols: kinetics and formation of chloroform. Environ Sci Technol 36:884–890CrossRef
  Garcia SAO, Pinto GP, Encina PAG, Mata RI (2014) Ecotoxicity ad environmental risk assessment of pharmaceuticals and personal care products in aquatic environments and wastewater treatment plants. Ecotoxicology 23:1517–1533CrossRef
  Ge F, Zhu L, Wang J (2008) Distribution of chlorination products of phenols under various pHs in water disinfection. Desalination 225:156–166CrossRef
  Glassmeyer ST, Shoemaker JA (2005) Effects of chlorination on the persistence of pharmaceuticals in the environment. Bull Environ Contam Toxicol 74:24–31CrossRef
  Kibbey TCG, Paruchuri R, Sabatini DA, Chen L (2007) Adsorption of beta blockers to environmental surfaces. Environ Sci Technol 41:5349–5356CrossRef
  Kim SD, Cho J, Kim IS, Vanderford BJ, Synder SA (2007) Occurrence and removal of pharmaceuticals and endocrine disruptors in South Korean surface, drinking, and waste waters. Water Res 41:1013–1021CrossRef
  Kosma CI, Lambropoulou DA, Albanis TA (2010) Occurrence ad removal of PPCPs in municipal and hospital wastewaters in Greece. J Hazard Mater 179:804–817CrossRef
  Lahti M, Oikari A (2011) Pharmaceuticals in settleable particulate material in urban and non-urban waters. Chemosphere 85:826–831CrossRef
  Luo Y, Guo W, Ngo HH, Nghiem LD, Hai FI, Zhang J, Liang S, Wang XC (2014) A review on the occurrence of micropollutants in the aquatic environment and their fate and removal during wastewater treatment. Sci Total Environ 473–474:619–641CrossRef
  Osachoff HL, Mohammadali M, Skirrow RC, Hall ER, Brown LYL, Aggelen GCV, Kennedy CJ, Helbing CC (2014) Evaluating the treatment of a synthetic wastewater containing a pharmaceutical and personal care product chemical cocktail: compound removal efficiency and effects on juvenile rainbow trout. Water Res 62:271–280CrossRef
  Padhye LP, Yao H, Kung’u FT, Huang C (2014) Year-long evaluation on the occurrence and fate of personal care products, and endocrine disrupting chemicals in an urban drinking water treatment plant. Water Res 51:266–276CrossRef
  Pinkston KE, Sedlak DL (2004) Transformation of aromatic ether and amine-containing pharmaceuticals during chlorine disinfection. Environ Sci Technol 38:4019–4025CrossRef
  Quintana JB, Rodil R, Cela R (2012) Reaction of β-blockers and β-agonist pharmaceuticals with aqueous chlorine. Investigation of kinetics and by-products by liquid chromatography quadrupole time-of-flight mass spectrometry. Anal Bioanal Chem 403:2385–2395CrossRef
  Salem AA, Wasfi IA, Al-Nassibi SS (2012) Trace determination of β-blockers and β2-agonists in distilled and waste-waters using liquid chromatography-tandem mass spectrometry and solid-phase extraction. J Chromatogr B 908:27–38CrossRef
  Sharma VK (2008) Oxidative transformations of environmental pharmaceuticals by Cl2, CIO2, O3, and Fe(VI): kinetics assessment. Chemosphere 73:1379–1386CrossRef
  Soufan M, Deborde M, Delmont A, Legube B (2013) Aqueous chlorination of carbamazepine: kinetic study and transformation product identification. Water Res 47:5076–5087CrossRef
  Sun Q, Lv M, Hu A, Yang X, Yu CP (2014) Seasonal variation in the occurrence and removal of pharmaceuticals and personal care products in a wastewater treatment plant in Xiamen, China. J Hazard Mater 277:69–75CrossRef
  Szabo J, Minamyer S (2014) Decontamination of chemical agents from drinking water infrastructure: a literature review and summary. Environ Int 72:119–123CrossRef
  Tay KS, Madehi N (2014) Ozonation of acebutolol in aqueous solution: ozonation by-products and degradation pathway. Sep Purif Technol 135:48–63CrossRef
  Tay KS, Rahman NA, Abas MRB (2010) Ozonation of parabens in aqueous solution: kinetics and mechanism of degradation. Chemosphere 81:1446–1453CrossRef
  Tian F, Liu W, Guo G, Qiang Z, Zhang C (2014) Kinetics and mechanism of dimethoate chlorination during drinking water treatment. Chemosphere 103:181–187CrossRef
  Zarelli A, DellaGreca M, Parollisi A, Iesce MR, Cermola F, Temussi F, Isidori M, Lavorgna M, Passananti M, Previtera L (2012) Chemical fate and genotoxic risk associated with hypochlorite treatment of nicotine. Sci Total Environ 426:132–138CrossRef
  Zhang TY, Xu B, Hu CY, Li M, Xia SJ, Tian FX, Gao NY (2013) Degradation kinetics and chloropicrin formation during aqueous chlorination of dinoseb. Chemosphere 93:2662–2668CrossRef
  Zhang Y, Zhuang Y, Geng J, Ren H, Zhang Y, Ding L, Xu K (2015) Inactivation of antibiotic resistance genes in municipal wastewater effluent by chlorination and sequential UV/chlorination disinfection. Sci Total Environ 512–513:125–132CrossRef
  
• 作者单位：Wan Nor Adira Wan Khalit (1)
  Kheng Soo Tay (1)
  
  1. Environmental Research Group, Department of Chemistry, Faculty of Science, University of Malaya, 50603, Kuala Lumpur, Malaysia
  
• 刊物类别：Earth and Environmental Science
• 刊物主题：Environment
  Environment
  Atmospheric Protection, Air Quality Control and Air Pollution
  Waste Water Technology, Water Pollution Control, Water Management and Aquatic Pollution
  Industrial Pollution Prevention
  
• 出版者：Springer Berlin / Heidelberg
• ISSN：1614-7499

文摘

This study investigated the reaction kinetics and the transformation by-products of acebutolol during aqueous chlorination. Acebutolol is one of the commonly used β-blockers for the treatment of cardiovascular diseases. It has been frequently detected in the aquatic environment. In the kinetics study, the second-order rate constant for the reaction between acebutolol and chlorine (k _app) was determined at 25 ± 0.1 °C. The degradation of acebutolol by free available chlorine was highly pH dependence. When the pH increased from 6 to 8, it was found that the k _app for the reaction between acebutolol and free available chlorine was increased from 1.68 to 11.2 M−1 min−1. By comparing with the reported k _app values, the reactivity of acebutolol toward free available chlorine was found to be higher than atenolol and metoprolol but lower than nadolol and propranolol. Characterization of the transformation by-products formed during the chlorination of acebutolol was carried out using liquid chromatography-quadrupole time-of-flight high-resolution mass spectrometry. Seven major transformation by-products were identified. These transformation by-products were mainly formed through dealkylation, hydroxylation, chlorination, and oxidation reactions.