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Reactions of resorcinol and its chlorinated derivatives with monochloramine: Identification of intermediates and products
Author(s) -
Heasley Victor L.,
Alexander Michael B.,
Deboard Ryan H.,
Hanley John C.,
McKee Tawnya C.,
Wadley Brian D.,
Shellhamer Dale F.
Publication year - 1999
Publication title -
environmental toxicology and chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.1
H-Index - 171
eISSN - 1552-8618
pISSN - 0730-7268
DOI - 10.1002/etc.5620181104
Subject(s) - resorcinol , chemistry , chloroform , medicinal chemistry , ether , aqueous solution , organic chemistry
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 (NH 2 Cl) in ether and aqueous solution (pH 7) is reported. NH 2 Cl 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 H 2 O and loss of CO 2 in the presence of NH 2 Cl 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 NH 2 Cl to give compounds 7 and 8; in the presence of NH 2 Cl, 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, CHCl 3 , which is produced from compound 3 with NH 2 Cl (4%) and with NaOCl (50%). The low production of CHCl 3 from compound 3 and NH 2 Cl is discussed in connection with the probable reactions of compounds 7 and 8 with NH 2 Cl and H 2 O.