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- Title
Reactions of resorcinol and its chlorinated derivatives with monochloramine: identification of intermediates and products
- Authors
Heasley, V. L.; Alexander, M. B.; DeBoard, R. H.; Hanley, Jr., J. C.; McKee, T. C.; Shellhamer, D. F.; Wadley, B. D.
- Abstract
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 ofchloroform, CHCl3, which is produced from compound 3 withNH2Cl (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.
- Subjects
CHEMISTRY; RESORCINOL; WATER quality
- Publication
Environmental Toxicology & Chemistry, 1999, Vol 18, Issue 11, p2406
- ISSN
0730-7268
- Publication type
Article
- DOI
10.1002/etc.5620181104