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Aqueous chlorination of resorcinol

Environmental Toxicology and Chemistry

By:
, , , , , , ,

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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. ?? 1989.

Additional Publication Details

Publication type:
Article
Publication Subtype:
Journal Article
Title:
Aqueous chlorination of resorcinol
Series title:
Environmental Toxicology and Chemistry
Volume
8
Issue:
12
Year Published:
1989
Language:
English
Larger Work Type:
Article
Larger Work Subtype:
Journal Article
First page:
1159
Last page:
1163
Number of Pages:
5