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Dioxane is used in a variety of applications as a versatile [[aprotic solvent]], e. g. for inks, adhesives, and cellulose esters. It is substituted for [[tetrahydrofuran]] (THF) in some processes, because of its lower toxicity and higher boiling point (101 °C, versus 66 °C for THF).<ref name=weiss>Klaus Weissermel, Hans-Jürgen Arpe (2003) "Industrial Organic Chemistry". John Wiley & Sons, page 158. {{ISBN|3527305785}}, 9783527305780.</ref>
While diethyl ether is rather insoluble in water, dioxane is [[miscible]] and in fact is [[hygroscopic]]. At standard pressure, the mixture of water and dioxane in the ratio 17.9:82.1 by mass is a positive [[azeotrope]] that boils at 87.6 C.<ref>Schneider, C. H.; Lynch, C. C.: ''The Ternary System: Dioxane-Ethanol-Water'' in [[J. Am. Chem. Soc.]], 1943, vol. 65, pp 1063–1066. {{
The oxygen atoms are [[Lewis base|Lewis-basic]], and so dioxane is able to solvate many inorganic compounds and serves as a chelating diether ligand. It forms 1:1 adducts with a variety of Lewis acids such as I<sub>2</sub>, phenols, alcohols, and bis(hexafloroacetylacetonato)copper(II). It is classified as a [[HSAB theory|hard base]] and its base parameters in the [[ECW model]] are E<sub>B</sub> =1.86 and C<sub>B</sub> = 1.29. It reacts with [[Grignard reaction|Grignard reagents]] to precipitate the magnesium dihalide. In this way, dioxane is used to drive the [[Schlenk equilibrium]].<ref name=Ullmann /> [[Dimethylmagnesium]] is prepared in this manner:<ref>{{cite journal |title=The Preparation of Dialkylmagnesium Compounds from Grignard Reagents|last1=Cope |first1=Arthur C. |journal=Journal of the American Chemical Society |volume=57 |page=2238 |year=1935 |doi=10.1021/ja01314a059 |issue=11}}</ref><ref>{{cite journal |last1=Anteunis |first1=M. |title=Studies of the Grignard Reaction. II. Kinetics of the Reaction of Dimethylmagnesium with Benzophenone and of Methylmagnesium Bromide-Magnesium Bromide with Pinacolone |journal=The Journal of Organic Chemistry |volume=27 |page=596 |year=1962 |doi=10.1021/jo01049a060 |issue=2}}</ref>
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|url-status = dead}}</ref> It is also 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'' because it is a known carcinogen in other animals.<ref>{{cite book |title= IARC Monographs Volume 71 |publisher= International Agency for Research on Cancer |url= http://monographs.iarc.fr/ENG/Monographs/vol71/mono71-25.pdf|access-date =11 July 2014}}</ref> The [[United States Environmental Protection Agency]] classifies dioxane as a probable human [[carcinogen]] (having observed an increased incidence of cancer in controlled animal studies, but not in epidemiological studies of workers using the compound), and a known irritant (with a no-observed-adverse-effects level of 400 milligrams per cubic meter) at concentrations significantly higher than those found in commercial products.<ref name="U.S.EPA_Dioxane">1,4-Dioxane (1,4-Diethyleneoxide). Hazard Summary. ''U.S. Environmental Protection Agency''. Created in April 1992; Revised in January 2000. [http://www.epa.gov/ttn/atw/hlthef/dioxane.html Fact Sheet].</ref> Under [[California Proposition 65 (1986)|California Proposition 65]], dioxane is classified in the U.S. State of California to cause cancer.<ref name="prop 65">{{cite web |title=Chemicals Known to the State to Cause Cancer or Reproductive Toxicity |url=http://www.oehha.org/prop65/prop65_list/files/P65single040210.pdf |date=2 April 2010 |quote=1,4-Dioxane CAS#123-91-1 (Listed 1 January 1988) |publisher=Office of Environmental Health Hazard Assessment |access-date=14 December 2013 |archive-url= https://web.archive.org/web/20100524160032/http://www.oehha.org/prop65/prop65_list/files/P65single040210.pdf |archive-date= 24 May 2010}}</ref> Animal studies in rats suggest that the greatest health risk is associated with inhalation of vapors in the pure form.<ref>{{cite journal |doi=10.2131/jts.33.141 |last1=Kano |first1=Hirokazu |last2=Umeda |first2=Yumi |last3=Saito |first3=Misae |last4=Senoh |first4=Hideki |last5=Ohbayashi |first5=Hisao |last6=Aiso |first6=Shigetoshi |last7=Yamazaki |first7=Kazunori |last8=Nagano |first8=Kasuke |last9=Fukushima |first9=Shoji |title=Thirteen-week oral toxicity of 1,4-dioxane in rats and mice |journal=The Journal of Toxicological Sciences |volume=33 |issue=2 |pages=141–53 |year=2008 |pmid=18544906|doi-access=free }}</ref><ref>{{cite journal |last1=Kasai |first1=T |last2=Saito |first2=M |last3=Senoh |first3=H |last4=Umeda |first4=Y |last5=Aiso |first5=S |last6=Ohbayashi |first6=H |last7=Nishizawa |first7=T |last8=Nagano |first8=K |last9=Fukushima |first9=S |title=Thirteen-week inhalation toxicity of 1,4-dioxane in rats |journal=Inhalation Toxicology |volume=20 |issue=10 |pages=961–71 |year=2008 |pmid=18668411 |doi=10.1080/08958370802105397|s2cid=86811931 }}</ref><ref>{{cite journal |last1=Kasai |first1=T. |last2=Kano |first2=H. |last3=Umeda |first3=Y. |last4=Sasaki |first4=T. |last5=Ikawa |first5=N. |last6=Nishizawa |first6=T. |last7=Nagano |first7=K. |last8=Arito |first8=H. |last9=Nagashima |first9=H. |last10=Fukushima |first10=S.|title=Two-year inhalation study of carcinogenicity and chronic toxicity of 1,4-dioxane in male rats |journal=Inhalation Toxicology |volume=21 |issue=11 |pages=889–97 |year=2009 |doi=10.1080/08958370802629610 |pmid=19681729 |s2cid=45963495 }}</ref> The State of New York has adopted a first-in-the-nation drinking water standard for 1,4-Dioxane and set the maximum contaminant level of 1 part per billion.<ref>{{Cite web |url=https://www.governor.ny.gov/news/governor-cuomo-announces-first-nation-drinking-water-standard-emerging-contaminant-14-dioxane |title = Governor Cuomo Announces First in the Nation Drinking Water Standard for Emerging Contaminant 1,4-Dioxane {{!}} Governor Andrew M. Cuomo |access-date=30 October 2020 |archive-date=29 October 2020 |archive-url=https://web.archive.org/web/20201029142313/https://www.governor.ny.gov/news/governor-cuomo-announces-first-nation-drinking-water-standard-emerging-contaminant-14-dioxane |url-status=dead }}</ref>
It tends to concentrate in the water and has little affinity for soil. It is resistant to abiotic degradation in the environment, and was formerly thought to also resist [[biodegradation]]. However, more recent studies since the 2000s have found that it can be biodegraded through a number of pathways, suggesting that [[bioremediation]] can be used to treat 1,4-dioxane contaminated water.<ref>{{cite journal |last1=Zenker |first1=Matthew J. |last2=Borden |first2=Robert C. |last3=Barlaz |first3=Morton A. |title=Occurrence and Treatment of 1,4-Dioxane in Aqueous Environments |journal=Environmental Engineering Science |date=September 2003 |volume=20 |issue=5 |pages=423–432 |doi=10.1089/109287503768335913}}</ref><ref>{{cite journal |last1=Zhang |first1=Shu |last2=Gedalanga |first2=Phillip B. |last3=Mahendra |first3=Shaily |title=Advances in bioremediation of 1,4-dioxane-contaminated waters |journal=Journal of Environmental Management |date=December 2017 |volume=204 |issue=Pt 2 |pages=765–774 |doi=10.1016/j.jenvman.2017.05.033|pmid=28625566 }}</ref>
=== Explosion hazard ===
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