Reactions of resorcinol and its chlorinated derivatives with monochloramine: Identification of intermediates and products

• Published in: Environmental toxicology and chemistry Vol. 18; no. 11; pp. 2406 - 2409
• Main Authors: Heasley, Victor L., Alexander, Michael B., Deboard, Ryan H., Hanley Jr, John C., McKee, Tawnya C., Wadley, Brian D., Shellhamer, Dale F.
• Format: Journal Article
• Language: English
• Published: Hoboken Wiley Periodicals, Inc 01.11.1999; SETAC
• Subjects: Applied sciences; chlorinated compounds; Chloroform; Drinking water and swimming-pool water. Desalination; Exact sciences and technology; Intermediates; Mechanisms; Monochloramine; monochloramines; Pollution; Resorcinol; Water treatment and pollution; Drinking water treatment; Chlorination; Chlorine Organic compounds; Model compound; Reaction product; Reaction mechanism; Disinfection; Experimental study; Humic acid; Resorcinol
• ISSN: 0730-7268; 1552-8618
• DOI: 10.1002/etc.5620181104

An investigation of the reaction of resorcinol (compound 1) and its chlorinated derivatives 4‐chlororesorcinol (compound 4), 4,6‐dichlororesorcinol (compound 5), and 2,4,6‐trichlororesorcinol (compound 2) with monochloramine (NH2Cl) in ether and aqueous solution (pH 7) is reported. NH2Cl reacted with compounds 1, 2, 4, and 5 to give the pentachloro intermediate, 2,2,4,4,6‐pentachloro‐5‐cyclohexen‐1,3‐dione (compound 3), which underwent ring opening with H2O and loss of CO2 in the presence of NH2Cl to produce the following: 1,1,3,5,5‐pentachloro‐3‐penten‐2‐one (compound 6), 1,1,1,3,5,5‐hexachloro‐3‐penten‐2‐one (compound 7), and 1,1,3,5,5,5‐hexachloro‐3‐penten‐2‐one (compound 8). Compound 6 reacted further with NH2Cl to give compounds 7 and 8; in the presence of NH2Cl, compound 7 rearranged to compound 8. Mechanisms for the preceding reactions are analyzed in detail. Another aspect of the investigation involved a determination of the amounts of chloroform, CHCl3, which is produced from compound 3 with NH2Cl (4%) and with NaOCl (50%). The low production of CHCl3 from compound 3 and NH2Cl is discussed in connection with the probable reactions of compounds 7 and 8 with NH2Cl and H2O.