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{{Distinguish|1,4-Dioxane}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{For|other dioxin compounds|dioxin}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 399104661 |
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| verifiedrevid = 477206346 |
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| Name = 1,4-Dioxin |
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| Name = 1,4-Dioxin |
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| ImageFileL1 = 1,4-Dioxin.svg |
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| ImageFile = 1,4-Dioxin.svg |
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| ImageSizeL1 = 100px |
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| ImageSize = 120px |
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| ImageFileR1 = 1,4-dioxin-3D-balls.png |
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| ImageFileL1 = 1,4-Dioxin-3D-balls 2.png |
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| ImageFileR1 = 1,4-Dioxin-3D-spacefill.png |
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| ImageSizeR1 = 120px |
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| PIN = 1,4-Dioxine<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 147 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref> |
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| IUPACName = 1,4-Dioxine |
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| SystematicName = 1,4-Dioxacyclohexa-2,5-diene |
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| OtherNames = ''p''-dioxin, dioxin |
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| OtherNames = 1,4-Dioxin<br />Dioxin<br />''p''-Dioxin<br />1,4-Dioxaannulene |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 71301 |
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| ChemSpiderID = 71301 |
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| InChI = 1/C4H4O2/c1-2-6-4-3-5-1/h1-4H |
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| InChI = 1/C4H4O2/c1-2-6-4-3-5-1/h1-4H |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = KVGZZAHHUNAVKZ-UHFFFAOYSA-N |
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| StdInChIKey = KVGZZAHHUNAVKZ-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 290-67-5 --> |
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| CASNo = 290-67-5 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| Section2 = {{Chembox Properties |
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| UNII = ZD32358XMG |
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| Formula = C<sub>4</sub>H<sub>4</sub>O<sub>2</sub> |
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| PubChem = 78968 |
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| MolarMass = 84.07 g/mol |
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| ChEBI = 134044 |
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| Appearance = Colorless liquid |
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|Section2={{Chembox Properties |
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| Formula = C{{sub|4}}H{{sub|4}}O{{sub|2}} |
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| MolarMass = 84.07 g/mol |
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| BoilingPtC = 75 <!-- CRC Handbook of Data on Organic Compounds, 2nd Edition, Weast, R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. --> |
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| Appearance = Colorless liquid |
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| BoilingPtC = 75 <!-- CRC Handbook of Data on Organic Compounds, 2nd Edition, Weast, R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. --> |
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| Section7 = {{Chembox Hazards |
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| MainHazards = highly flammable |
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| MainHazards = highly flammable |
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| Section8 = {{Chembox Related |
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| OtherCpds = ], ]}} |
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| OtherCompounds = ], ]<br> |
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'''1,4-Dioxin''' (also referred as '''dioxin''' or '''''p''-dioxin''') is a ], ], non-aromatic<ref>Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 16: Six-Membered Hetarenes with Two Identical Heteroatoms</ref> ] with the ] C{{sub|4}}H{{sub|4}}O{{sub|2}}. There is an ]ic form of 1,4-dioxin, ] (or ''o''-dioxin). 1,2-Dioxin is very unstable due to its ]-like characteristics. |
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The term "dioxin" is most commonly used for a family of derivatives of dioxin, known as ] (PCDDs). |
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==Preparation== |
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1,4-Dioxin can be prepared by ], namely by the ] of ] and ]. The ] formed has a carbon-carbon double bond, which is ]. The epoxide then undergoes a ], forming 1,4-dioxin and regenerating maleic anhydride.<ref>{{cite journal | doi = 10.1039/p19940000927 | journal = J. Chem. Soc., Perkin Trans. |volume=1 |issue=8 | year = 1994 | pages = 927–931 | title = 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 | first=R. Alan |last=Aitken |first2=J. I. G. |last2=Cadogan |name-list-style=amp |first3=Ian |last3=Gosneya }}</ref> |
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] |
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==Derivatives== |
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] and ] numbering scheme of ], the parent compound of PCDDs]] |
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The word "]" can refer in a general way to compounds which have a dioxin core skeletal structure with ] molecular groups attached to it. For example, ] is a compound whose structure consists of two benzo- groups fused onto a 1,4-dioxin ring. |
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===Polychlorinated dibenzodioxins=== |
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{{Main|polychlorinated dibenzodioxins}} |
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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 ] (PCDDs), among which ] (TCDD), a {{Not a typo|tetrachlorinated}} derivative, is the best known. The polychlorinated dibenzodioxins, which can also be classified in the family of ], have been shown to ] in humans and ] due to their ] properties, and are known ], ], and ]. |
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PCDDs are formed through ], ] bleaching and ] processes.<ref name="mgov">{{Cite web |url=http://maine.gov/dep/dioxin/ |title=Dioxin Information |archiveurl=https://web.archive.org/web/20090615124630/http://maine.gov/dep/dioxin/ |archivedate=2009-06-15 |publisher=Department of Environmental Protection, State of Maine |year=2005 |url-status=dead |access-date=2008-08-10 }}</ref> The combination of heat and chlorine creates dioxin.<ref name="mgov"/> Since chlorine is often a part of the Earth's ], natural ecological activity such as volcanic activity and forest fires can lead to the formation of PCDDs.<ref name="mgov"/> Nevertheless, PCDDs are mostly produced by human activity.<ref name="mgov"/> |
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Famous PCDD exposure cases include ] sprayed over vegetation by the ] in Malaya during the ] and the ] in Vietnam during the ], the ], and the poisoning of ]. |
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] are a related class compounds to PCDDs which are often included within the general term "dioxins". |
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==References== |
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{{reflist}} |
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{{DEFAULTSORT:Dioxin, 1, 4-}} |
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] |