1,4-Dioxane 1572944 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]] [[cs:1,4-dioxan]] [[de:1,4-Dioxan]] [[et:Dioksaan]] [[es:Dioxano]] [[fr:Dioxane]] [[it:Diossano]] [[lv:Dioksāns]] [[nl:1,4-Dioxaan]] [[ja:ジオキサン]] [[pl:Dioksan]] [[ru:Диоксан]] [[sv:1,4-Dioxan]]