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

✍ Scribed by Victor L. Heasley; Michael B. Alexander; Ryan H. Deboard; John C. Hanley Jr.; Tawnya C. McKee; Brian D. Wadley; Dale F. Shellhamer

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 64 KB
• Volume: 18
• Category: Article
• ISSN: 0730-7268
• DOI: 10.1002/etc.5620181104

✦ Synopsis

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, 2,2,4,4,6pentachloro-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.