Aqueous Chlorination of Resorcinol

Abstract

An investigation of the aqueous chlorination (NaOCl) of resorcinol is reported. The following intermediates were detected in moderate to high yield at different pH values and varying percentages of chlorination: 2-chloro-, 4-chloro-, 2,4-dichloro-, 4,6-dichloro-and 2,4,6-trichlororesorcinol. Only trace amounts of the intermediates were detected when the chlorination was conducted in the presence of phosphate buffer. This result has significant implications since resorcinol in phosphate buffer has been used as a model compound in several recent studies on the formation of chlorinated hydrocarbons during chlorination of drinking water. Relative rates of chlorination were determined for resorcinol and several of the chlorinated resorcinols. Resorcinol was found to chlorinate only three times faster than 2,4,6-trichlororesorcinol. The structure 2,4,6-trichlororesorcinol was established as a monohydrate even after sublimation. A tetrachloro or pentachloro intermediate was not detected, suggesting that the ring-opening step of such an intermediate must be rapid.

Understanding fungal functional biodiversity during the mitigation of environmentally dispersed pentachlorophenol in cork oak forest soils

“…All LC and MS solvents, as well as those required in the fast‐solvent extractions, were of the highest analytical grade. Chlorinated derivatives of resorcinol, hydroquinone and catechol were produced through an aqueous chlorination methodology (Heasley et al ., ) and 2,3,5,6‐tetrachloro‐4‐methoxyphenol (Dro A) was synthesized as described before (Hiebl et al ., ).…”

Chlorination of Phenols Revisited: Unexpected Formation of α,β-Unsaturated C4-Dicarbonyl Ring Cleavage Products

“…The formation of chlorinated and non-chlorinated -unsaturated dicarbonyl compounds from the reactions of chlorine with phenolic compounds has not been previously reported and cannot be explained by reaction pathways postulated in literature. 65,67,68 However, a potentially relevant reaction pathway involving the formation of a radical intermediate via one-electron transfer has been indicated previously based on the detection of chlorinated phenyl-phenols when phenol and alkylphenols react with chlorine. [69][70][71][72] Furthermore, the formation of BDA has been reported previously for the reaction of phenol with hydroxyl radicals ( • OH), which also suggests the potential involvement of phenoxy radical intermediates, which can form from BDA via an endoperoxide intermediate.…”

Coagulation of Iodide-Containing Resorcinol Solution or Natural Waters with Ferric Chloride Can Produce Iodinated Coagulation Byproducts

“…According to previous studies, halogenated resorcinol is the dominant halogenation byproducts of resorcinol when resorcinol is present at a high dose. 46,47 As shown in Figure 2c, no significant peak was observed in the absence of iodide, indicating that iodide played a crucial role in the formation of halogenated compounds.…”