Editing Diethyl ether peroxide

{{chembox
|Watchedfields = changed
|verifiedrevid = 445507000
|Name = Diethyl ether hydroperoxide
|ImageFile = Diethyl ether peroxide.svg
|ImageSize = 136px
|ImageFile1 = Diethyl Ether Peroxide.png
|ImageSize1 = 160
|Section1={{Chembox Identifiers
|InChI = 1/C4H10O3/c1-3-6-4(2)7-5/h4-5H,3H2,1-2H3
|InChIKey = CXWWPQGYBJCHJL-UHFFFAOYAS
|SMILES1 = CC(OCC)OO
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C4H10O3/c1-3-6-4(2)7-5/h4-5H,3H2,1-2H3
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = CXWWPQGYBJCHJL-UHFFFAOYSA-N
|CASNo_Ref = {{cascite|correct|??}}
|CASNo = 18321-53-4
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID =19985446
|PubChem = 126387
|SMILES = CCOC(OO)C
}}
|Section2={{Chembox Properties
|C=4|H=10|O=3
|Appearance = colorless liquid
|Density = 1.005 g/cm<sup>3</sup>
|BoilingPtC = 62 to 64
|BoilingPt_notes = at 18.7 hPa (reduced pressure)
}}
|Section3={{Chembox Hazards
|MainHazards = Explosive
|NFPA-F = 4 | NFPA-H = 2 | NFPA-R = 4 | NFPA-S =
}}
}}
'''Diethyl ether hydroperoxide''' is the [[organic compound]] with the formula C<sub>2</sub>H<sub>5</sub>OCH(OOH)CH<sub>3</sub>. It is a colorless liquid. Diethyl ether hydroperoxide and its condensation products are responsible for the explosive [[organic peroxide]]s that slowly form upon exposure of [[diethyl ether]] to ambient air and temperature conditions.<ref name=jacs>{{cite journal |doi=10.1021/ja01638a012|title=Organic Peroxides. XIX. α-Hydroperoxyethers and Related Peroxides|year=1954|last1=Milas|first1=Nicholas A.|last2=Peeler|first2=Robert L.|last3=Mageli|first3=Orville L.|journal=Journal of the American Chemical Society|volume=76|issue=9|pages=2322–2325|bibcode=1954JAChS..76.2322M }}</ref><ref>{{cite journal | author = A. Rieche, R. Meister | title = Modellversuche zur Autoxidation der Äther | journal = [[Angewandte Chemie]] | volume = 49 | issue = 5 | pages = 101–103 | year = 1936 | doi = 10.1002/ange.19360490502 | bibcode = 1936AngCh..49..101R | language = de}}</ref>

==Synthesis and reactions==
Diethyl ether hydroperoxide can be formed by the [[photooxygenation]] of diethyl ether. This is a radical process, driven by UV excitation of molecular oxygen into a more reactive form. Its formation is usually undesirable due to the associated risk of explosion. For this reason commercial samples of diethyl ether will usually contain [[antioxidant]]s such as [[Butylated hydroxytoluene|BHT]] and be contained in a material able to block UV rays, such as amber glass.

:[[File:Ether-autoxidation.png|400px]]

It can be intentionally prepared in high yield by the acid-catalyzed addition of [[hydrogen peroxide]] to [[ethyl vinyl ether]]:<ref name=jacs/>
:C<sub>2</sub>H<sub>5</sub>OCH=CH<sub>2</sub> + H<sub>2</sub>O<sub>2</sub> → C<sub>2</sub>H<sub>5</sub>OCH(OOH)CH<sub>3</sub>
Related hydroperoxides can be produced similarly.

Diethyl ether hydroperoxide, upon heating in water, decomposes to [[acetaldehyde]]:
:C<sub>2</sub>H<sub>5</sub>OCH(OOH)CH<sub>3</sub> → CH<sub>3</sub>CHO + C<sub>2</sub>H<sub>5</sub>OH + H<sub>2</sub>O<sub>2</sub>

Diethyl ether hydroperoxide forms polymers known as '''diethyl ether peroxide''', or '''ethylidene peroxide''':

[[Image:Diethylether peroxide.png|Formation of diethyl ether peroxide]]

The peroxide is a colorless oil that is an extremely [[Brisance|brisant]] and [[friction]] sensitive [[explosive material]], however the polymeric materials are solid making them more dangerous as evaporation of the volatile diethyl ether can leave thin films of pure explosive.

== Tests ==
Diethyl ether peroxides can be detected with a [[potassium iodide]] (KI) solution in acetic acid or [[potassium iodide]]/[[starch]] paper. A positive test results in the formation of [[iodine]] (I<sub>2</sub>) that causes a yellow or brown color of the ether phase or a dark bluish spot on the paper strip.<ref>{{cite web|url=http://www.sigmaaldrich.com/chemistry/solvents/learning-center/peroxide-formation.html |title=Peroxide Forming Solvents|website=Sigma-Aldrich|accessdate=2014-07-09}}</ref>

== References ==
{{Reflist}}

[[Category:Organic peroxides]]
[[Category:Ethers]]
[[Category:Liquid explosives]]
[[Category:Organic peroxide explosives]]
[[Category:Ethoxy compounds]]