Chlorine dioxide oxidation of aromatic hydrocarbons commonly found in water

Aqueous reactions of chlorine dioxide with hydrocarbons

“…(3) the stoichiometry, 2 mol of C102 reacting with 1 mol of olefin at pH 7.0, and the indene:C102 ratio of 1:1 for pH 4.0 (4) a first-order reaction with respect to both the olefin and the C102 and, therefore, second order overall (5) the isotope effect of 1 found for allylic hydrogens replaced by deuterium (6) the solvent effect, indicating charge development in the transition state of the rate determining step All these observations are consistent with the mechanistic scheme demonstrated in Figure 7 for the indene-C102 reaction at pH 4.0, for which the product distribution is described in Table II. The rate-determining step is the oxidation of the double bond to form the cation radical la.…”

“…Saturated aliphatic hydrocarbons and phenyl-substituted aliphatic side chains (4), as well as aliphatic olefins (5), were reportedly unreactive under typical water conditions. When naphthalene and methyl-substituted naphthalenes were reacted with very high concentrations of C102, however, oxidative and chlorinated naphthalene derivatives could be detected (6). Lindgren and co-workers (7,8) found both oxidative and chlorinated products from the reactions of C102 with some olefins and proposed a mechanism whereby allylic hydrogen is abstracted by C102, giving free-radical intermediates.…”

Influence of humic substances on the formation of chlorinated polycyclic aromatic hydrocarbons during chlorination of polycyclic aromatic hydrocarbon polluted water

“…The formation of chlorinated and oxygenated PAH during chlorination of PAH-polluted water has been shown by several authors (22,23). Some chlorinated derivatives of pyrene and benzo[a]pyrene have been found to show high mutagenic activity in the Salmonella TA-100 test (24).…”

Facile incorporation of bromine into aromatic systems under conditions of water chlorination

“…In addition, earlier studies had examined in detail the reactions of aqueous solutions of naphthalene with chlorine dioxide (13) and biphenyl and naphthalene (14,15) with chlorine in the absence of bromide. In addition, earlier studies had examined in detail the reactions of aqueous solutions of naphthalene with chlorine dioxide (13) and biphenyl and naphthalene (14,15) with chlorine in the absence of bromide.…”

“…Naphthalene and biphenyl were chosen for study because of their significance as industrial products, their presence in environmental settings, the interest in their halogenated derivatives, their differing reactivity to electrophilic aromatic substitution (e.g., naphthalene > biphenyl), and the availability of halogenated product standards. In addition, earlier studies had examined in detail the reactions of aqueous solutions of naphthalene with chlorine dioxide (13) and biphenyl and naphthalene (14,15) with chlorine in the absence of bromide.…”