Editing Ethylene oxide (section)

{{Short description|Cyclic compound (C2H4O)}}
{{Redirect|Oxirane|oxiranes as a class of molecules|epoxide}}{{Distinguish|Ethylene dione|Ethyl oxide}}
{{Use dmy dates|date=January 2022}}
{{Chembox
| Watchedfields  = changed
| verifiedrevid  = 446701253
| ImageFileL1    = Ethylene oxide.svg
| ImageSizeL1    = 100 px
| ImageClassL1   = skin-invert
| ImageFileR1    = Ethylene-oxide-from-xtal-3D-balls.png
| ImageSizeR1    = 150 px
| PIN            = Oxirane<ref>{{cite book |author=[[International Union of Pure and Applied Chemistry]] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=[[Royal Society of Chemistry|The Royal Society of Chemistry]] |pages=714 |isbn=978-0-85404-182-4 |doi=10.1039/9781849733069}}</ref>
| SystematicName = Epoxyethane<br>Oxacyclopropane
| OtherNames     = Ethylene oxide<br>Dimethylene oxide<br>1,2-Epoxyethane<br>[3]-crown-1<br>Epoxide
| Section1       = {{Chembox Identifiers
|Abbreviations = EO, EtO
|Beilstein = 102378
|ChEMBL = 1743219
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 6114
|Gmelin = 676
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = JJH7GNN18P
|UNNumber = 1040
|InChIKey = IAYPIBMASNFSPL-UHFFFAOYAX
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C2H4O/c1-2-3-1/h1-2H2
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = IAYPIBMASNFSPL-UHFFFAOYSA-N
|CASNo = 75-21-8
|CASNo_Ref = {{cascite|correct|CAS}}
|EINECS = 200-849-9
|PubChem = 6354
|SMILES = O1CC1
|InChI = 1/C2H4O/c1-2-3-1/h1-2H2
|RTECS = KX2450000
|MeSHName = Ethylene+Oxide
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI = 27561
|KEGG_Ref = {{keggcite|correct|kegg}}
|KEGG = D03474
}}
| Section2       = {{Chembox Properties
|Formula = {{chem2|C2H4O}}
|MolarMass = 44.052{{nbsp}}g·mol<sup>−1</sup><ref name=r3430>[[#Haynes|Haynes]], p. 3.430</ref>
|Appearance = Colorless gas
|Odor = Like diethyl ether<ref>Ethylene oxide, odor</ref>
|Density = 0.8821{{nbsp}}g·cm<sup>−3</sup><ref name=r3430/>
|Dipole = 1.94{{nbsp}}D<ref name=r1520/>
|MeltingPtC = −112.46
|MeltingPt_ref =<ref name=r3430/>
|BoilingPtC = 10.4
|BoilingPt_ref =<ref name=r3430/>
|Solubility = Miscible
|VaporPressure = 1.46{{nbsp}}atm (20{{nbsp}}°C)<ref name=PGCH/>
|RefractIndex = 1.3597 (589{{nbsp}}nm)<ref name=r3430/>
|MagSus = −30.5·10<sup>−6</sup>{{nbsp}}cm<sup>3</sup>/mol<ref>[[#Haynes|Haynes]], p. 3.576</ref>
}}
| Section3       = {{Chembox Thermochemistry
|DeltaHf = −52.6{{nbsp}}kJ·mol<sup>−1</sup><ref name=r522>[[#Haynes|Haynes]], p. 5.22</ref>
|DeltaGf = −13.0{{nbsp}}kJ·mol{{sup|−1}}<ref name=r522/>
|Entropy = 242.5{{nbsp}}J·mol<sup>−1</sup>·K<sup>−1</sup><ref name=r522/>
|HeatCapacity = 47.9{{nbsp}}J·mol<sup>−1</sup>·K<sup>−1</sup><ref name=r522/>
}}
| Section4       = {{Chembox Hazards
|ExternalSDS = [https://www.inchem.org/documents/icsc/icsc/eics0155.htm ICSC 0155]
|GHSPictograms = {{GHS flame}}{{GHS skull and crossbones}}{{GHS health hazard}}
|MainHazards = [[Carcinogen]]<br>Extremely flammable
|NFPA-H = 3
|NFPA-F = 4
|NFPA-R = 3
|HPhrases = {{H-phrases|220|230|301|314|331|335|336|340|350|360FD|372}}
|PPhrases = {{P-phrases|202|210|260|280|301+310+330|303+361+353|305+351+338+310|410+403}}<ref name="sigmaaldrich 2020">{{cite web |title=Ethylene oxide 387614 |url=https://www.sigmaaldrich.com/catalog/product/aldrich/387614?lang=en&region=GB |website=Sigma-Aldrich |access-date=1 September 2020 |archive-url=https://web.archive.org/web/20201205212012/https://www.sigmaaldrich.com/catalog/product/aldrich/387614?lang=en&region=US |archive-date=5 December 2020 |url-status=live}} [https://archive.org/download/ethylene-oxide-msds/Ethylene%20oxide%20MSDS.pdf Alt URL]</ref>
|FlashPtC = −20
|FlashPt_ref =<ref name=r1520>[[#Haynes|Haynes]], p. 15.20</ref>
|AutoignitionPtC = 429
|AutoignitionPt_ref=<ref name=r1520/>
|ExploLimits = 3 to 100%
|PEL = TWA 1{{nbsp}}ppm 5{{nbsp}}ppm [15-minute excursion]<ref name=PGCH>{{PGCH|0275}}</ref>
|REL = Ca TWA <0.1{{nbsp}}ppm (0.18{{nbsp}}mg/m<sup>3</sup>) C 5{{nbsp}}ppm (9{{nbsp}}mg/m<sup>3</sup>) [10-min/day]<ref name=PGCH/>
|IDLH = Ca [800{{nbsp}}ppm]<ref name=PGCH/>
|LC50 = 836{{nbsp}}ppm (mouse, 4{{nbsp}}hr)<br>4000{{nbsp}}ppm (rat, 4{{nbsp}}hr)<br>800{{nbsp}}ppm (rat, 4{{nbsp}}hr)<br>819{{nbsp}}ppm (guinea pig, 4{{nbsp}}hr)<br>1460{{nbsp}}ppm (rat, 4{{nbsp}}hr)<br>835{{nbsp}}ppm (mouse, 4{{nbsp}}hr)<br>960{{nbsp}}ppm (dog, 4{{nbsp}}hr)<ref>{{IDLH|75218|Ethylene oxide}}</ref>
}}
| Section5       = {{Chembox Related
|OtherFunction = [[Aziridine]],<br>[[thiirane]],<br>[[borirane]]
|OtherFunction_label = heterocycles
}}
}}

'''Ethylene oxide''' is an [[organic compound]] with the [[chemical formula|formula]] {{chem2|C2H4O}}. It is a cyclic [[ether]] and the simplest [[epoxide]]: a three-membered [[ring (chemistry)|ring]] consisting of one [[oxygen]] atom and two [[carbon]] atoms. Ethylene oxide is a colorless and [[flammable]] gas with a faintly sweet odor. Because it is a [[strained ring]], ethylene oxide easily participates in a number of [[addition reaction]]s that result in ring-opening. Ethylene oxide is [[isomer]]ic with [[acetaldehyde]] and with [[vinyl alcohol]]. Ethylene oxide is industrially produced by [[oxidation]] of [[ethylene]] in the presence of a [[silver]] [[catalyst]].

The reactivity that is responsible for many of ethylene oxide's hazards also makes it useful. Although too dangerous for direct household use and generally unfamiliar to consumers, ethylene oxide is used for making many consumer products as well as non-consumer chemicals and intermediates. These products include detergents, thickeners, solvents, plastics, and various organic chemicals such as [[ethylene glycol]], ethanolamines, simple and complex [[glycols]], [[polyglycol ether]]s, and other compounds. Although it is a vital raw material with diverse applications, including the manufacture of products like [[polysorbate 20]] and [[polyethylene glycol]] (PEG) that are often more effective and less toxic than alternative materials, ethylene oxide itself is a very hazardous substance. At room temperature it is a very flammable, [[carcinogenic]], [[mutagenicity|mutagenic]], irritating, and [[anaesthetic]] gas.<ref name=Ullmann/>

Ethylene oxide is a surface [[disinfectant]] that is widely used in hospitals and the medical equipment industry to [[sterilization (microbiology)#Ethylene oxide|replace steam in the sterilization]] of heat-sensitive tools and equipment, such as disposable plastic syringes.<ref>{{cite book |page=309 |title=Encyclopedia of Chemical Processing and Design |volume=20 |author1=McKetta, John J. |author2=Cunningham, William A. |publisher=CRC Press |year=1984 |isbn=0-8247-2470-4 |url=https://books.google.com/books?id=oJy5wdzi0yUC&pg=PA309}}</ref> It is so flammable and extremely explosive that it is used as a main component of [[thermobaric weapon]]s;<ref name=e1/><ref name=e2/> therefore, it is commonly handled and shipped as a refrigerated liquid to control its hazardous nature.<ref name=Ullmann>Rebsdat, Siegfried and Mayer, Dieter (2005) "Ethylene Oxide" in ''Ullmann's Encyclopedia of Industrial Chemistry''. Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a10_117}}.</ref><ref>[https://www.superfoodly.com/ethylene-oxide-sterilization-non-eto-spices/ ''Ethylene Oxide Sterilization: Are ETO Treated Spices Safe?''], SuperFoodly, 10 April 2017</ref>