1,4-dioxin

Structural formula
General
Surname	1,4-dioxin
other names	Dioxin; p -dioxin;
Molecular formula	C 4 H 4 O 2
External identifiers / databases
PubChem	78968
Wikidata	Q161534
properties
Molar mass	84.07 g mol −1
Physical state	liquid
boiling point	75 ° C
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1,4-Dioxin , also p-dioxin , is an oxygen-containing heterocyclic organic compound, which can be understood formally as a closed double ether of the dihydric alcohol ethenediol (HO – CH = CH – OH) or as an oxygen heterocycle of cyclohexadiene: 1, 4-dioxa-2,5-cyclohexadiene. In addition to 1,4-dioxin, there is the isomer 1,2-dioxin ( o -dioxin ).

Dioxin isomers: 1,2-dioxin on the left, 1,4-dioxin on the right.

The toxic, carcinogenic and long-lasting polychlorinated dibenzodioxins and furans are derived from the structure of dioxin and the chemically related furan . The term dioxin is widely used outside experts for this class, which includes the so-called Seveso 2,3,7,8-Tetrachlorodibenzodioxin (TCDD) is one that the chemical accident in Seveso , the Seveso disaster was released.

Extraction and presentation

1,4-Dioxin can be prepared by epoxidizing the double bond of the product of the Diels-Alder reaction of furan and maleic anhydride and cleaving it to maleic anhydride and 1,4-dioxin by a retro-Diels-Alder reaction .

Individual evidence

↑ CRC Handbook of Data on Organic Compounds, 2nd Edition, Weast, RC and Grasselli, JG, ed (s)., CRC Press, Inc., Boca Raton, FL, 1989, 1.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ R. Alan Aitken, JIG Cadogan, Ian Gosneya: Effect of ring strain on the formation and pyrolysis of some Diels-Alder Adducts of 2-sulfolenes (2,3-dihydrothiophenes 1,1-dioxide) and maleic anhydride with 1.3 -services and products derived therefrom . In: J. Chem. Soc., Perkin Trans. 1 . 1994, pp. 927-931. doi : 10.1039 / p19940000927 .

[1] CRC Handbook of Data on Organic Compounds, 2nd Edition, Weast, RC and Grasselli, JG, ed (s)., CRC Press, Inc., Boca Raton, FL, 1989, 1.

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[3] R. Alan Aitken, JIG Cadogan, Ian Gosneya: Effect of ring strain on the formation and pyrolysis of some Diels-Alder Adducts of 2-sulfolenes (2,3-dihydrothiophenes 1,1-dioxide) and maleic anhydride with 1.3 -services and products derived therefrom . In: J. Chem. Soc., Perkin Trans. 1 . 1994, pp. 927-931. doi : 10.1039 / p19940000927 .