1,4-Dioxane
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220035219
2008-06-17T23:52:32Z
Edgar181
491706
/* Safety and environmental concerns */ ref fix; cap.
<div>
{{Chembox new
| Name = 1,4-Dioxane
| ImageFileL1 = 1-4-Dioxane.svg
| ImageNameL1 = Chemical structure of dioxane
| ImageSizeL1 = 100px
| ImageFileR1 = 1,4-dioxane-3D-vdW.png
| ImageSizeR1 = 120px
| ImageNameR1 = 1,4-dioxane
| IUPACName = 1,4-Dioxane<br />1,4-Dioxacyclohexane
| OtherNames = [1,4]Dioxane<br />''p''-Dioxane<br />[6]-crown-2
| Section1 = {{Chembox Identifiers
| CASNo = 123-91-1
| EINECS = 204-661-8
| SMILES = C1OCCOC1
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>4</sub>H<sub>8</sub>O<sub>2</sub>
| MolarMass = 88.11 g/mol
| MeltingPt = 11.8°C
| BoilingPt = 101.1°C
| Density = 1.033 g/cm³
}}
| Section4 = {{Chembox Thermochemistry
| DeltaHf = -354 kJ/mol
| DeltaHc = -2363 kJ/mol
| Entropy = 196.6 J.K<sup>–1</sup>.mol<sup>–1</sup>
}}
| Section7 = {{Chembox Hazards
| EUClass = Flammable ('''F''')<br />[[Carcinogen|Carc. Cat. 3]]<br />Irritant ('''Xn''')
| RPhrases = {{R11}}, {{R19}}, {{R36/37}},<br />{{R40}}, {{R66}}
| SPhrases = {{S2}}, {{S9}}, {{S16}},<br />{{S36/37}}, {{S46}}
| FlashPt = 12 °C
}}
}}
</div>
''Not to be confused with [[dioxin]].''
'''1,4-Dioxane''', often just called '''dioxane''', is a clear, colorless [[heterocyclic]] [[organic compound]] which is a [[liquid]] at room [[temperature]] and [[pressure]]. It has the [[molecular formula]] C<sub>4</sub>H<sub>8</sub>O<sub>2</sub> and a boiling point of 101°C. It is commonly used as an [[aprotic solvent]]. 1,4-Dioxane has a weak [[odor|smell]] similar to that of [[diethyl ether]]. There are also two other less common [[isomer]]ic compounds, '''1,2-dioxane''' and '''1,3-dioxane'''. 1,2-Dioxane is a [[peroxide]] which forms naturally in old bottles of [[tetrahydrofuran]].
1,4-Dioxane is classified as an [[ether]], with each of its two [[oxygen]] [[atom]]s forming an ether [[functional group]]. It is more [[Polar molecule|polar]] than [[diethyl ether]], which also has four [[carbon]]s, but only one ether functional group. Diethyl ether is rather insoluble in water, but 1,4-dioxane is [[miscible]] with [[Water (molecule)|water]] and is [[hygroscopic]]. Its higher polarity and slightly higher [[molecular mass]] also gives it a substantially higher [[boiling point]] than diethyl ether. When used as a solvent for a [[Grignard]] reaction, Dioxane favorably affects the formation of magnesium halide salts in the [[Schlenk equilibrium]].
The name ''dioxane'' should not be confused with ''[[dioxin]]'', which is a different compound but is also a diether (two ether functional groups).
[[Image:Dioxane isomers.PNG|frame|left|<center>'''Isomers of Dioxane'''</center><br />Small blue numbers show numbering of atoms in rings.]]
<br clear=left/>
==Uses==
1,4-Dioxane is primarily used in solvent applications for the manufacturing sector; however, it is also found in fumigants and automotive coolant. Additionally, the chemical is also used as a [[foaming agent]] and appears as an accidental byproduct of the ethoxylation<ref>{{cite web
| title = Occurrence of 1,4-Dioxane in Cosmetic Raw Materials and Finished Cosmetic Products
| author = Roderick E. Black
| publisher = Journal of IAOC International
| url = http://www.atypon-link.com/AOAC/doi/abs/10.5555/jaoi.2001.84.3.666
| volume: 84
| Issue: 3
| Cover date: May 2001
| page(s): 666-670
| accessdate = 2006-02-02}}</ref> process in cosmetics manufacturing. It may contaminate cosmetics and personal care products such as deodorants, shampoos, toothpastes and mouthwashes.<ref>{{cite web
| title = CHEC Chemical Summary: 1,4-dioxane
| publisher = Children's Health Environmental Coalition
| url = http://www.checnet.org/HealtheHouse/chemicals/chemicals-detail.asp?Main_ID=273
| accessdate = 2006-02-02}}</ref>
It is also commonly used as an internal standard for calibrating chemical shifts in [[NMR]], as [[tetramethylsilane]] (the compound to which all chemical shifts are ultimately referenced) is not soluble in [[D2O]].
==Safety and environmental concerns==
Dioxanes combine with atmospheric oxygen on standing to form explosive [[peroxide]]s, similar to many other ethers. [[Distillation]] of dioxanes concentrates these peroxides increasing the danger. Appropriate precautions should be taken.
1,4-Dioxane is a known eye and respiratory tract irritant. It is suspected of causing damage to the central nervous system, liver and kidneys.<ref>{{cite web
| title = International Chemical Safety Card
| publisher = National Institute for Occupational Safety and Health
| url = http://www.cdc.gov/niosh/ipcsneng/neng0041.html
| accessdate = 2006-02-02}}</ref>
Accidental worker exposure to 1,4-dioxane has resulted in several deaths.<ref>{{cite web
| title = OPPT Chemical Fact Sheets 1,4-Dioxane (CAS No. 123-91-1)
| publisher = United States Environmental Protection Agency
| url = http://www.epa.gov/opptintr/chemfact/dioxa-fs.txt
| accessdate = 2006-02-02}}</ref> Dioxane is classified by the [[International Agency for Research on Cancer|IARC]] as a [[List of IARC Group 2B carcinogens|Group 2B carcinogen]]: ''possibly carcinogenic to humans'' due to the fact that it is a known carcinogen in animals.<ref>{{cite web
| title = Eleventh Report on Carcinogens
| publisher = United States Department of Health and Human Services’ National Toxicology Program
| url = http://ntp-server.niehs.nih.gov/ntp/roc/eleventh/profiles/s080diox.pdf
| accessdate = 2006-02-02}}</ref>
The State of California, under [[proposition 65]], listed 1,4-dioxane as a chemical known to cause cancer on January 1, 1988.<ref> {{ cite web| title = Proposition 65 Chemicals | url=http://www.oehha.ca.gov/prop65/prop65_list/files/032108list.pdf}}</ref>
Like many solvents, 1,4-dioxane forms [[contamination plumes]] in [[groundwater]] when released to the environment. Groundwater supplies have been adversely impacted in several areas.
1,4-Dioxane is highly soluble in groundwater, does not readily bind to soils, and readily leaches to groundwater. It is also
resistant to naturally occurring biodegradation processes. Due to these properties, a 1,4-dioxane plume is often much larger
(and further downgradient) than the associated solvent plume.<ref>{{cite web
| title = Crawford, Scott. "Down N' Dirty With 1,4-Dioxane."
| publisher = XDD, LLC's Xpert Solutions Newsletter (Fall 2007/Winter 2008)
| url = http://xdd-llc.com/images/XDD_Newsletter_Fall-Winter_2007.pdf
| accessdate = 2008-01-16}}</ref>
==See also==
* [[Ether]]
* [[Crown ether]]
==References==
<references/>
==External links==
* [http://physchem.ox.ac.uk/MSDS/DI/1,4-dioxane.html Safety (MSDS) data for 1,4-dioxane]
* [http://www.evol.nw.ru/labs/lab38/spirov/hazard/dioxane.html Hazard Database]
<!-- Dead link * [http://www-cie.iarc.fr/htdocs/monographs/vol71/019-dioxane.html IARC Monograph: "1,4-Dioxane"] -->
* [http://ptcl.chem.ox.ac.uk/MSDS/DI/1,3-dioxane.html Safety (MSDS) data for 1,3-dioxane]
* [http://www.safecosmetics.org/newsroom/press.cfm?pressReleaseID=21 Press conference on 1,4-dioxane found in children's bath products (2/8/07)]
* [http://www.organicconsumers.org/bodycare/DioxaneRelease08.cfm Press conference on 1,4-dioxane found in personal care products labeled "natural" or "organic" (3/14/08)]
* [http://www.organicconsumers.org/articles/article_12797.cfm California Attorney General sues companies with personal care products containing 1,4-dioxane (6/10/08)]
* [http://www.xdd-llc.com XDD, LLC: Developers of remediation options for 1,4-dioxane.]
{{DEFAULTSORT:Dioxane, 1,4-}}
[[Category:Oxygen heterocycles]]
[[Category:Ethers]]
[[Category:IARC Group 2B carcinogens]]
[[Category:Ether solvents]]
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