Biomaterial Database

[Chlorination of ethynyl estradiol: a kinetic and mechanistic study]. 2013

Bin-Nan Wang, and Guo-Qiang Liu, and De-Yang Kong, and Jun-He Lu

College of Resource and Environmental Sciences, Nanjing Agricultural University, Nanjing 210095, China. njwangbinnan@qq.com

The objective of this research is to explore the fundamentals of reactions between chlorine and ethynyl estradiol (EE2), which is expected to occur during the drinking water treatment. The first step of EE2 chlorination was shown to follow the second-order kinetics with the first order to concentrations of both target compound and chlorine, respectively. Apparent rate constants of EE2 chlorination exhibit the pH-dependent profile which indicates that the phenolic ring is the preferred site of attack by Cl. The transformation of EE2 is governed by 3 elementary reactions between different species of EE2 and HClO. The deprotonated EE2 anion is significantly more reactive than its neutral conjugate. HPLC/MS analysis revealed that several Cl atoms can be incorporated into this site via complex multi-step pathways, resulting in the formation of mono and di-chlorine substituted EE2. The incorporation of the third Cl is accompanied by immediate broken down of the ring via hydrolysis. The results of this study are helpful to fully understand the behavior of EE2 in chlorinated drinking water disinfection, provide the basis for evaluating the potential exposure of this contaminant to human. The data of this work also give insights to the formation of chlorinated drinking water disinfection by-products (DBPs).

UI	MeSH Term	Description	Entries
D007700	Kinetics	The rate dynamics in chemical or physical systems.
D010636	Phenols	Benzene derivatives that include one or more hydroxyl groups attached to the ring structure.
D002713	Chlorine	An element with atomic symbol Cl, atomic number 17, and atomic weight 35, and member of the halogen family.	Chlorine Gas,Chlorine-35,Cl2 Gas,Chlorine 35,Gas, Chlorine,Gas, Cl2
D003198	Computer Simulation	Computer-based representation of physical systems and phenomena such as chemical processes.	Computational Modeling,Computational Modelling,Computer Models,In silico Modeling,In silico Models,In silico Simulation,Models, Computer,Computerized Models,Computer Model,Computer Simulations,Computerized Model,In silico Model,Model, Computer,Model, Computerized,Model, In silico,Modeling, Computational,Modeling, In silico,Modelling, Computational,Simulation, Computer,Simulation, In silico,Simulations, Computer
D004997	Ethinyl Estradiol	A semisynthetic alkylated ESTRADIOL with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally, and is often used as the estrogenic component in ORAL CONTRACEPTIVES.	19-Norpregna-1,3,5(10)-trien-20-yne-3,17-diol, (17alpha)-,Ethynyl Estradiol,Estinyl,Ethinyl Estradiol Hemihydrate,Ethinyl Estradiol, (8 alpha)-Isomer,Ethinyl Estradiol, (8 alpha,17 alpha)-Isomer,Ethinyl Estradiol, (8 alpha,9 beta,13 alpha,14 beta)-Isomer,Ethinyl Estradiol, (9 beta,17 alpha)-Isomer,Ethinyl-Oestradiol Effik,Ethinylestradiol Jenapharm,Ethinyloestradiol,Lynoral,Microfollin,Microfollin Forte,Progynon C,Estradiol, Ethinyl,Estradiol, Ethynyl,Ethinyl Oestradiol Effik,Hemihydrate, Ethinyl Estradiol,Jenapharm, Ethinylestradiol
D014874	Water Pollutants, Chemical	Chemical compounds which pollute the water of rivers, streams, lakes, the sea, reservoirs, or other bodies of water.	Chemical Water Pollutants,Landfill Leachate,Leachate, Landfill,Pollutants, Chemical Water
D052244	Endocrine Disruptors	Exogenous agents, synthetic and naturally occurring, which are capable of disrupting the functions of the ENDOCRINE SYSTEM including the maintenance of HOMEOSTASIS and the regulation of developmental processes. Endocrine disruptors are compounds that can mimic HORMONES, or enhance or block the binding of hormones to their receptors, or otherwise lead to activating or inhibiting the endocrine signaling pathways and hormone metabolism.	Endocrine Disrupting Chemical,Endocrine Disrupting Chemicals,Endocrine Disruptor,Endocrine Disruptor Effect,Endocrine Disruptor Effects,Chemical, Endocrine Disrupting,Chemicals, Endocrine Disrupting,Disrupting Chemical, Endocrine,Disruptor Effect, Endocrine,Disruptor Effects, Endocrine,Disruptor, Endocrine,Disruptors, Endocrine,Effect, Endocrine Disruptor,Effects, Endocrine Disruptor
D054879	Halogenation	Covalent attachment of HALOGENS to other compounds.	Bromination,Chlorination,Fluorination,Iodination,Iodation
D060766	Drinking Water	Water that is intended to be ingested.	Bottled Water,Potable Water,Water, Bottled,Water, Drinking,Water, Potable