602:
613:
278:
60:
51:
38:
464:
817:
Aitken, R. Alan; Cadogan, J. I. G. & Gosneya, Ian (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".
717:, natural ecological activity such as volcanic activity and forest fires can lead to the formation of PCDDs. Nevertheless, PCDDs are mostly produced by human activity.
477:
601:
670:(TCDD), a tetrachlorinated derivative, is the best known. The polychlorinated dibenzodioxins, which can also be classified in the family of
327:
807:
Science of
Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 16: Six-Membered Hetarenes with Two Identical Heteroatoms
792:
472:
292:
667:
590:
484:
159:
663:
653:
594:
558:
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processes. The combination of heat and chlorine creates dioxin. Since chlorine is often a part of the Earth's
751:
658:
Because of their extreme importance as environmental pollutants, current scientific literature uses the name
90:
662:
commonly for simplification to denote the chlorinated derivatives of dibenzo-1,4-dioxin, more precisely the
235:
852:
256:
776:
273:
773:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
754:
are a related class compounds to PCDDs which are often included within the general term "dioxins".
574:
511:
636:" can refer in a general way to compounds which have a dioxin core skeletal structure with
244:
199:
78:
644:
is a compound whose structure consists of two benzo- groups fused onto a 1,4-dioxin ring.
8:
714:
612:
179:
135:
125:
557:
The term "dioxin" is most commonly used for a family of derivatives of dioxin, known as
277:
641:
625:
788:
745:
729:
519:
883:
827:
780:
725:
617:
582:
523:
515:
350:
224:
741:
784:
455:
855:. Department of Environmental Protection, State of Maine. 2005. Archived from
877:
733:
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675:
570:
440:
391:
721:
59:
831:
737:
695:
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621:
17:
50:
702:
687:
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671:
543:
436:
373:
190:
454:
Except where otherwise noted, data are given for materials in their
706:
691:
679:
551:
158:
445:
211:
856:
633:
586:
539:
24:
578:
170:
148:
37:
261:
597:, forming 1,4-dioxin and regenerating maleic anhydride.
816:
647:
589:formed has a carbon-carbon double bond, which is
550:-dioxin). 1,2-Dioxin is very unstable due to its
875:
223:
134:
640:molecular groups attached to it. For example,
276:
198:
243:
764:
611:
272:
876:
847:
845:
843:
841:
396:75 °C (167 °F; 348 K)
304:Key: KVGZZAHHUNAVKZ-UHFFFAOYSA-N
178:
301:InChI=1S/C4H4O2/c1-2-6-4-3-5-1/h1-4H
838:
720:Famous PCDD exposure cases include
314:Key: KVGZZAHHUNAVKZ-UHFFFAOYAD
311:InChI=1/C4H4O2/c1-2-6-4-3-5-1/h1-4H
214:
13:
58:
49:
14:
895:
668:2,3,7,8-tetrachlorodibenzodioxin
600:
462:
36:
23:For other dioxin compounds, see
724:sprayed over vegetation by the
593:. The epoxide then undergoes a
458:(at 25 °C , 100 kPa).
810:
801:
777:The Royal Society of Chemistry
664:polychlorinated dibenzodioxins
654:polychlorinated dibenzodioxins
648:Polychlorinated dibenzodioxins
628:, the parent compound of PCDDs
607:
569:1,4-Dioxin can be prepared by
564:
559:polychlorinated dibenzodioxins
408:Occupational safety and health
1:
757:
752:Polychlorinated dibenzofurans
672:halogenated organic compounds
95:1,4-Dioxacyclohexa-2,5-diene
7:
820:J. Chem. Soc., Perkin Trans
785:10.1039/9781849733069-FP001
45:
10:
900:
686:properties, and are known
651:
595:retro-Diels–Alder reaction
22:
15:
701:PCDDs are formed through
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425:
405:
400:
378:84.07 g/mol
343:
323:
288:
118:
101:
89:
77:
72:
44:
35:
16:Not to be confused with
744:, and the poisoning of
591:converted to an epoxide
554:-like characteristics.
736:in Vietnam during the
629:
63:
54:
779:. 2014. p. 147.
728:in Malaya during the
674:, have been shown to
666:(PCDDs), among which
615:
91:Systematic IUPAC name
62:
53:
853:"Dioxin Information"
832:10.1039/p19940000927
624:numbering scheme of
575:Diels–Alder reaction
542:form of 1,4-dioxin,
79:Preferred IUPAC name
32:
642:dibenzo-1,4-dioxin
630:
626:dibenzo-1,4-dioxin
499:(also referred as
485:Infobox references
426:Related compounds
64:
55:
30:
794:978-0-85404-182-4
746:Viktor Yushchenko
730:Malayan Emergency
493:Chemical compound
491:
490:
432:Related compounds
421:highly flammable
386:Colorless liquid
257:CompTox Dashboard
160:Interactive image
113:1,4-Dioxaannulene
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771:"Front Matter".
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726:British military
618:skeletal formula
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583:maleic anhydride
573:, namely by the
524:chemical formula
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351:Chemical formula
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742:Seveso disaster
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518:, non-aromatic
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480: ?)
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335:O\1/C=C\O/C=C/1
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826:(8): 927–931.
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709:bleaching and
678:in humans and
652:Main article:
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616:Figure 1: The
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566:
563:
538:. There is an
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456:standard state
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859:on 2009-06-15
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734:U.S. military
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711:manufacturing
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682:due to their
681:
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676:bioaccumulate
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571:cycloaddition
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441:dibenzodioxin
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392:Boiling point
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861:. Retrieved
857:the original
823:
819:
812:
803:
772:
766:
750:
722:Agent Orange
719:
700:
659:
657:
631:
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512:heterocyclic
505:
504:
500:
496:
495:
444:
417:Main hazards
406:
180:CHEBI:134044
119:Identifiers
108:
102:Other names
738:Vietnam War
715:environment
696:carcinogens
638:substituent
622:substituent
608:Derivatives
565:Preparation
411:(OHS/OSH):
383:Appearance
344:Properties
83:1,4-Dioxine
31:1,4-Dioxin
18:1,4-Dioxane
863:2008-08-10
758:References
703:combustion
688:teratogens
684:lipophilic
632:The word "
544:1,2-dioxin
497:1,4-Dioxin
437:1,2-dioxin
374:Molar mass
245:ZD32358XMG
191:ChemSpider
147:3D model (
126:CAS Number
104:1,4-Dioxin
561:(PCDDs).
522:with the
878:Category
732:and the
707:chlorine
692:mutagens
680:wildlife
552:peroxide
540:isomeric
520:compound
401:Hazards
136:290-67-5
884:Dioxins
660:dioxins
516:organic
510:) is a
508:-dioxin
478:what is
476: (
446:dithiin
368:
212:PubChem
111:-Dioxin
791:
740:, the
694:, and
634:dioxin
587:adduct
585:. The
501:dioxin
473:verify
470:
328:SMILES
106:Dioxin
73:Names
25:dioxin
579:furan
293:InChI
225:78968
200:71301
171:ChEBI
149:JSmol
789:ISBN
620:and
581:and
546:(or
236:UNII
828:doi
781:doi
577:of
503:or
262:EPA
215:CID
880::
840:^
822:.
787:.
748:.
705:,
698:.
690:,
514:,
439:,
866:.
834:.
830::
824:1
797:.
783::
548:o
536:2
534:O
532:4
530:H
528:4
526:C
506:p
468:N
366:2
364:O
362:4
360:H
358:4
356:C
264:)
260:(
151:)
109:p
27:.
20:.
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
