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    Dioxins: Dioxin

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    Dioxins: Dioxin

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    Dioxins: Dioxin

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    6

    Dioxins
    The term dioxin is a generalization of a family of chlorinated organic
    compounds, some of which have been found to be extremely hazardous
    to life in minute quantities. There has been public concern that these
    compounds may be generated from incineration processes.

    Dioxin Family
    The dioxin molecular framework consists of two benzene rings con-
    nected by two oxygen bridges, as shown in Figure 6-1. Also indicated
    in this illustration are the basic molecular frameworks of the related
    compounds polychlorinated dibenzofurans (PDFFS) and polychlori-
    nated biphenols (PCBs).
    At least two chlorine atoms occurring at two or more of the eight
    numbered locations define a dioxin, and there are 73 different combi-
    nations, as noted in Table 6-1. These are all known as polychlorinated
    dibenzo-p-dioxins, (PCDDs). There are two dioxin isomers possible with

    Table 6-1 Dioxin Analyses


    Average
    Polychlorinated Molecular Molecular No. of
    Dibenzo-p-dioxin Formula Weight Isomers
    Dichloro-dibenzo-p-dioxin C12H,;CI20 2 253.1 10
    (DCDD)
    Trichloro-dibenzo-p-dioxin C12HsCl302 287.5 14
    (Tri-CDD)
    Tetrachloro-dibenzo-p-dioxin C12H4 C40 2 322.0 22
    (TCDD)
    Pentachloro-dibenzo-p-dioxin C12H3Cls0 2 356.4 14
    (Penta-CDD)
    Hexachloro-dibenzo-p-dioxin C12H2Cl.;02 390.9 10
    (Hexa-CDD)
    Heptachloro-dibenzo-p-dioxin C12HCl70 2 425.3 2
    (Hepta-CDD)
    Octachloro-dibenzo-p-dioxin C12Cl.02 459.8 1
    (OCDD)
    Total Isomers 73

    54
    C. R. Brunner, Hazardous Air Emissions from Incineration
    © Chapman and Hall 1985
    Dioxins 55

    a~0:Q' I
    I~O ,
    •
    DIBENZO-P-DIOXIN

    a¢C¢1
    I
    I
    ,

    DIBENzorURAIi

    ~
    '

    • ~- 4'

    a J'

    POLYCHLORINATED BYPH£NYL (With the addition of at lea.t two ato••


    of chlorine)
    Figure 6-1 Polycyclic organic compounds.

    only one chlorine atom, monochlorinated dibenzo-p-dioxin. The general


    term, which includes the mono- and poly- chlorinated dioxins, is chlor-
    inated dibenzo-p-dioxin, (COD).
    Of these varieties of dioxins, the most toxic dioxin found to date is
    2,3,7,8-TCOO, which has the molecular structure illustrated in Figure
    6-2 and an average molecular weight of approximately 322. This com-
    pound is a solid at standard conditions with a melting point in the range
    of 57rF to 581°F. At 77°F its solubility in water is 0.0002 mgll, 57 mgll
    in benzene, 4.8 mgll in octanol and 1.0 mgll in methanol.
    PCOOs are thermally stable up through 1300°F. Above this temper-
    ature they will start to decompose. Their vapor pressure is extremely
    low, less than one millionth of a millimeter of mercury at standard
    conditions.
    This low vapor pressure indicates that a PCOO compound will not
    readily volatilize from a surface at ambient temperatures. This physical

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