Dioxin

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Not to be confused with dioxane or digoxin.
For the chemical compounds which are environmental pollutants, see polychlorinated dibenzodioxins.
1,4-Dioxin
IUPAC name 1,4-dioxin
Other names p-dioxin, dioxin
Identifiers
CAS number [290-67-5]
Properties
Molecular formula C4H4O2
Molar mass 84.07 g/mol
Appearance Colorless liquid
Boiling point

75°C (348°K)

Hazards
EU classification Toxic (T)
Main hazards highly flammable
Related compounds
Related compounds dibenzodioxin
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox references

Dioxin is a heterocyclic, organic, antiaromatic compound with the chemical formula C4H4O2. There are two isomers, 1,2-dioxin (or o-dioxin) and 1,4-dioxin (or p-dioxin). Their chemical structures are shown at right. The ortho isomer 1,2-dioxin is very unstable due to its peroxide-like characteristics. The known properties of 1,4-dioxin are listed in the infobox to the right.

1,4-dioxin can be prepared by cycloaddition, namely by the Diels-Alder reaction.

Dioxin is used as a blanket term for a family of chemical compounds that are formed through combustion, chlorine bleaching and manufacturing processes. The combination of heat and chlorine creates dioxin. Since chlorine is often a part of the earth's environment, natural ecological activity such as volcanic activity and forest fires can lead to the formation of dioxin. Nevertheless, dioxin, a highly carcinogenic and toxic compound, is mostly created by human activity.

Contents

Other meanings

Skeletal formulas and substituent numbering schemes of Dioxin isomers Skeletal formulas and substituent numbering schemes of Dioxin isomers The skeletal formula and substituent numbering scheme of dibenzo-1,4-dioxin, the parent compound of PCDDs The skeletal formula and substituent numbering scheme of dibenzo-1,4-dioxin, the parent compound of PCDDs

The word dioxin can also in a general way refer to compounds whose molecules have a dioxin core skeletal structure with substituent molecular groups attached to it. For example, dibenzo-1,4-dioxin is a compound whose structure consists of two benzo- groups fused onto a 1,4-dioxin ring as shown below (see also Dibenzodioxin).

Because of their extreme importance as environmental pollutants, current scientific literature uses the name dioxins commonly for simplification to denote the chlorinated derivatives of dibenzo-1,4-dioxin, more precisely the polychlorinated dibenzodioxins (PCDDs), among which TCDD, a tetrachlorinated derivative, is the best known. The polychlorinated dibenzodioxins, which can also be classified in the family of halogenated organic compounds, have been shown to bioaccumulate in humans and wildlife due to their lipophilic properties, and are known teratogens, mutagens, and carcinogens. References under the main article on polychlorinated dibenzodioxins.

Additionally, sometimes with dioxins a similar, but unrelated compound type the polychlorinated dibenzofurans of like importance are also implied.

Toxicity

Some dioxin derivatives are carcinogenic, and directly correllated with an increase in the likelihood of attaining cancer (see above). Scientists are working to establish their exact toxicity. The job is made difficult because we are not dealing with pure chemicals, but a mixture, and toxicity depends on the particular molecular arrangement of the compound, that of the highest toxicity is the 2,3,7,8-tetrachlorodibenzo-1,4-dioxin (pictured here as well). When people say dioxins, they often refer to these chlorinated derivatives, not the compound described in this article. These cases are discussed in detail in the article on Polychlorinated dibenzodioxin or PCDD but the toxicity of even some of these is disputed. The Vietnamese Veterans case, the Seveso case, and Viktor Yushchenko's chloracne case and more are all discussed in that article. Another group of compounds of similar toxicity to that of the PCDD's are the polychlorinated dibenzofurans, their toxicity is also discussed with Dioxin derivatives, sometimes calling them all erroneously dioxins.

Health and Safety

Preventing dioxin release into the environment

In January, 1997, The U.S. Environmental Protection Agency's New England office and the Maine Department of Environmental Protection announced a precedent-setting program to control levels of dioxin in waste water discharges from Lincoln Pulp & Paper Company of Lincoln Maine. Per EPA, "The dioxin limits in the Lincoln permit are the most stringent ever required of a paper mill by EPA anywhere in the country. Lincoln, an integrated bleached kraft paper mill making recycled products from waste sawdust, has agreed to the terms of federal and state waste water discharge permits that will require the company to achieve the following:

Per EPA: "It sets a high standard for other mills and substantially advances our efforts to achieve Governor King's goal of lifting dioxin related fish consumption advisories and ultimately eliminating the discharge of dioxin."

References

  1. ^ R. Alan Aitken, J. I. G. Cadogan and Ian Gosneya (1994). "Effect of ring strain on the formation and pyrolysis of some Diels–Alder adducts of 2-sulfolene (2,3-dihydrothiophene 1,1-dioxide) and maleic anhydride with 1,3-dienes and products derived therefrom". J. Chem. Soc., Perkin Trans. 1: 927–931. doi:10.1039/p19940000927. 
  2. ^ a b c d Dioxin from State of Maine's Department of Environmental Protection
  3. ^ a b c Most Stringent Dioxin Effluent Limits Ever Issued Included In Lincoln Pulp and Paper Permits Issued by EPA AND MEDEP from United States Environmental Protection Agency (EPA)


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