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Chlorination in dilute aqueous systems; 2,4,6-trichlorophenol.

J G Smith, S F Lee, A Netzer

    Environmental Letters
    |January 1, 1975
    PubMed
    Summary
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    Chlorinating phenol in wastewater produces 2,6-dichloroquinone and 2,4,4,6-tetrachloro-2,5-cyclohexadienone. Further chlorination creates minor polychlorinated byproducts, clarifying reaction pathways.

    Area of Science:

    • Environmental Chemistry
    • Organic Chemistry
    • Water Treatment

    Background:

    • Chlorination is a common wastewater treatment method.
    • The transformation of organic contaminants during chlorination is not fully understood.
    • Phenol, a common organic contaminant, undergoes complex reactions when chlorinated.

    Purpose of the Study:

    • To elucidate the reaction pathway of 2,4,6-trichlorophenol during chlorination.
    • To identify the major and minor products formed.
    • To understand the role of hypochlorous acid in these transformations.

    Main Methods:

    • Treatment of 2,4,6-trichlorophenol in dilute aqueous solution.
    • Use of excess hypochlorous acid.
    • Control of reaction pH between 3.5 and 6.

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    Main Results:

    • Formation of 2,6-dichloroquinone as a major product.
    • Formation of 2,4,4,6-tetrachloro-2,5-cyclohexadienone as a major product.
    • Generation of minor amounts of additional polychlorinated species via addition reactions.

    Conclusions:

    • The chlorination of 2,4,6-trichlorophenol yields specific quinone and cyclohexadienone products.
    • Further addition of chlorine or hypochlorous acid to the aromatic ring results in minor polychlorinated byproducts.
    • This study clarifies key aspects of phenol transformation during wastewater chlorination.