Chlorine disinfection chemistry of aromatic compounds. Polynuclear aromatic hydrocarbons: rates, products, and mechanisms

Abstract

Kinetic expressions for the aqueous reactions of chlorine with phenanthrene (pH 3-10), fluorene (pH 3-5), and fluoranthene (pH 3-5) have been developed. At pH 3-5 the rate of reaction of each PAH studied could be related to the chlorine concentration (-d[PAH]). Phenanthrene, also studied at high pH values (pH >8.8), followed a rate expression consistent with pseudo-first-order kinetics (-d[phen]). The overall rate expression that was developed for phenanthrene is suggested as a model for correlating the rates of reaction of chlorine with polynuclear aromatic compounds in water over the entire pH range (pH 3-10) that might reasonably be encountered during disinfection. This overall expression is Cl•, and O" (24).The arene oxide (phenanthrene 9,10-oxide) was the predominant phenanthrene product at pH 54 while phenanthrene-9,10-dione and 9-chlorophenanthrene were the major products at pH S4.

Photochlorination of Polycyclic Aromatic Hydrocarbons in Acidic Brine Solution

“…Shiraishi et al (1985) reported that the ClPAHs were present in tap waters at 0.01-0.1 ng/L levels, suggested that the ClPAHs were produced in the tap water supply system by reaction of the parent PAHs with residential chlorine. Indeed, the production of ClPAHs were confirmed by the aqueous reactions of chlorine treatment with PAHs (Oyler et al 1978(Oyler et al , 1983. For other treatment of PAHs in aqueous condition, formations of ClPAHs have been confirmed by the electrochemical treatment in saline solutions (Muff and Søgaard 2011).…”

Behaviour of pyrene and its decomposition by-products in chlorination

“…In the pH range of 5.1-7.1, the main species of chlorine is the same (i.e. HOCl, pKa ¼ 7.58, Oyler et al 1983), but pyrene was decomposed faster at higher pH.…”

“…Oyler et al (1983) reported that at pH # 4, the decomposition rates of fluorene, phenanthrene and fluoranthene in chlorination increased with decreasing pH. Reactions (1) and (2) below were associated with the decompositions.…”

Analysis of Halogenated Polycyclic Aromatic Hydrocarbons in the Air

“…In the late 1970s to 1980s, Oyler et al identified various chlorinated PAHs with 2~4-ring as the products of aqueous chlorination reactions of PAHs using reversed phase HPLC with UV detector, GC equipped with photoionization detector, and GC/MS [19,20]. The study would be first report that ClPAHs were detected from environmental sample, whereas that would be artificial environment of watertreatment including chlorination reaction of PAHs.…”

“…Nilsson and Colmsjo investigated in detail the analytical methods of not only chlorosubstituted PAHs, here defined as ClPAHs, but also chloro-added PAHs using normal (20) phase HPLC [21,22]. In the study, three stationary phases, i.e.…”