View source for Ethylene oxide

{{Redirect|Oxirane|oxiranes as a class of molecules|epoxide}}
{{chembox
| Watchedfields = changed
| verifiedrevid = 267280175
| ImageFileL1 = Ethylene-oxide-2D-skeletal.png
| ImageSizeL1 = 100 px 
| ImageFileR1 = Ethylene-oxide-from-xtal-3D-balls.png
| ImageSizeR1 = 150 px
| IUPACName = oxirane [http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6354&loc=ec_rcs]
| SystematicName = 
| OtherNames = epoxyethane, ethylene oxide, dimethylene oxide,oxacyclopropane
| Section1 = {{Chembox Identifiers
| Abbreviations = EO, EtO
| CASNo = 75-21-8
| CASNo_Ref = {{cascite}}
| EINECS = 200-849-9
| EINECSCASNO = 
| PubChem = 6354
| SMILES = C1CO1
| InChI = 1/C2H4O/c1-2-3-1/h1-2H2
| RTECS = KX2450000
| MeSHName = Ethylene+Oxide
| ChEBI = 27561
| KEGG = C06548
| ATCCode_prefix = 
| ATCCode_suffix = 
| ATC_Supplemental =}}
| Section2 = {{Chembox Properties
| Formula = C<sub>2</sub>H<sub>4</sub>O
| MolarMass = 44.05 g mol<sup>−1</sup>
| Appearance = colorless gas
| Density = 0.882 g/mL, 7.360 lbs/gallon
| MeltingPt = −111.3 °C
| Melting_notes = 
| BoilingPt = 10.7 °C
| Boiling_notes = 
| Solubility = miscible
| SolubleOther = 
| Solvent = 
| LogP = 
| VaporPressure = 
| HenryConstant = 
| AtmosphericOHRateConstant = 
| pKa = 
| pKb =}}
| Section3 = {{Chembox Structure
| CrystalStruct = 
| Coordination = 
| MolShape =}}
| Section4 = {{Chembox Thermochemistry
| DeltaHf = −52.6 kJ mol<sup>−1</sup>
| DeltaHc = 
| Entropy = 243 J mol<sup>−1</sup> K<sup>−1</sup>
| HeatCapacity =}}
| Section5 = {{Chembox Pharmacology
| AdminRoutes = 
| Bioavail = 
| Metabolism = 
| HalfLife = 
| ProteinBound =
| Excretion = 
| Legal_status = 
| Legal_US = 
| Legal_UK = 
| Legal_AU = 
| Legal_CA = 
| PregCat = 
| PregCat_AU = 
| PregCat_US =}}
| Section6 = {{Chembox Explosive
| ShockSens = 
| FrictionSens = 
| ExplosiveV = 
| REFactor =}}
| Section7 = {{Chembox Hazards
| EUClass = 
| EUIndex = 
| MainHazards = [[carcinogen]]
| NFPA-H = 3
| NFPA-F = 4
| NFPA-R = 3
| NFPA-O = 
| RPhrases = 
| SPhrases = 
| RSPhrases = 
| FlashPt = −20 °C
| Autoignition = 
| ExploLimits = 3 to 100%
| PEL =}}
| Section8 = {{Chembox Related
| OtherAnions = 
| OtherCations = 
| OtherFunctn = [[Aziridine]],<br> [[Ethylene sulfide]],<br> [[Borirane]]
| Function = heterocycles
| OtherCpds =}}
}}

'''Ethylene oxide''', also called '''oxirane''', is the [[organic compound]] with the [[chemical formula|formula]] C<sub>2</sub>H<sub>4</sub>O. This colorless flammable gas with a faintly sweet odor is the simplest [[epoxide]], a three-membered ring consisting of two carbon and one oxygen atom. Because of its special molecular structure, ethylene oxide easily participates in the [[addition reaction]], opening its cycle, and thus easily [[polymerisation|polymerizes]]. Ethylene oxide is [[isomer]]ic with [[acetaldehyde]]. It  is a strong poison to humans, showing carcinogenic, [[mutagenicity|mutagenic]], irritating and narcotic effects. 

The major application of ethylene oxide is for producing many chemicals and intermediates, such as [[ethylene glycol]], ethanolamines, simple and complex glycols, polyglycol ethers and other compounds. It is also a common gas-phase [[disinfectant]] which is widely used in hospitals to sterilize heat-sensitive tools and equipment.<ref>{{cite book|url=http://books.google.com/?id=oJy5wdzi0yUC&pg=PA309|page=309|title=Encyclopedia of Chemical Processing and Design|volume=20|author=John J. McKetta, William A. Cunningham|publisher=CRC Press|year=1984|isbn=0824724704}}</ref> Ethylene oxide is industrially produced by direct [[oxidation]] of [[ethylene]] in the presence of [[silver]] [[catalyst]]. It is extremely flammable and explosive and 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.<ref name=Ullmann>Siegfried Rebsdat, Dieter Mayer "Ethylene Oxide" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005.{{DOI|10.1002/14356007.a10_117}}.</ref> 

==History==
Ethylene oxide was first reported in 1859 by the [[France|French]] chemist [[Charles-Adolphe Wurtz]],<ref>{{cite journal|author=Wurtz, A.|journal= Compt. Rend.|volume= 48|pages= 101–104 |year=1859| title=}}</ref> who prepared it by treating [[2-chloroethanol]] with [[potassium hydroxide]]: 

:Cl–CH<sub>2</sub>CH<sub>2</sub>–OH + KOH → (CH<sub>2</sub>CH<sub>2</sub>)O + KCl + H<sub>2</sub>O

Wurtz measured the [[boiling point]] of ethylene oxide as 13.5 °C, slightly higher than the present value, and discovered the ability of ethylene oxide to react with acids and salts of metals.<ref name="oe1">{{cite book
|chapter = Part I. Structure and properties of ethylene oxide. Features of the reactivity of ethylene oxide and the structure of its molecules
|title = Ethylene oxide
| editor= PV Zimakova and Ph. O. Dymenta
|publisher = Khimiya
|year = 1967
|pages = 15–17}}</ref> Wurtz mistakenly assumed that ethylene oxide has the properties of an organic base. This delusion lasted until 1896 when [[Georg Bredig]] found that ethylene oxide is not an [[electrolyte]].<ref name="oe1" /> Its distinct difference with [[ether]]s, in particular, its propensity to join the addition reactions typical of unsaturated compounds, had long been a matter of debate. Only in 1893, the heterocyclic triangular structure of ethylene oxide had been proposed.<ref name="oe1" />

The first synthesis method had long remained the only, despite numerous attempts of scientists, including Wurtz himself, to produce ethylene oxide directly from [[ethyl]].<ref name="ect">{{cite book
| chapter = Etylene Oxide
|title = Kirk-Othmer Encyclopedia of Chemical Technology. Elastomers, synthetic to Expert Systems
| edition = 4| location = New York
|publisher = John Wiley & Sons
|year = 1994
|volume = 9
|pages = 450–466}}</ref> Only in 1931, French chemist Theodore Lefort developed a method of direct oxidation of ethylene in the presence of [[silver]] [[catalyst]].<ref>{{cite web
|author = Lefort, T.E.
|year = 1935
|url = http://www.freepatentsonline.com/1998878.pdf
|title = Process for the production of ethylene oxide. United States Patent 1998878
|accessdate = 2009-09-23}}</ref> Since 1940, almost all ethylene oxide produced industrially uses this method.<ref>{{cite journal|title= Manufacture and Uses of Ethylene Oxide and Ethylene Glycol| author= P. P. McClellan| journal= Ind. Eng. Chem.|year= 1950| volume= 42|pages= 2402–2407| doi= 10.1021/ie50492a013}}</ref> Sterilization by ethylene oxide for the preservation of [[spice]]s was patented in 1938 by the [[United States|American]] chemist [[Lloyd Hall]]. Ethylene oxide achieved industrial importance during [[World War I]] as a precursor to both the coolant [[ethylene glycol]] and the [[chemical weapon]] [[Sulfur mustard|mustard gas]]. 

==Molecular structure and properties==
[[File:Ethylene-oxide.png|250px|thumb|right]]

The epoxy cycle of ethylene oxide is an almost regular triangle with bond angles of about 60° and a significant angular stress corresponding to the energy of 105 kJ/mol.<ref>{{cite book
|chapter= Voltage molecules
|title = Chemical Encyclopedia 
| editor = Knunyants, IL 
|publisher = "Soviet encyclopedia"
|year = 1988
|volume = 3
|pages = 330–334}}</ref><ref name="traven">
{{cite book|author = Traven VF
|title = Organic chemistry: textbook for schools| editor = VFTraven
|publisher = ECC "Academkniga"
|year = 2004
|volume = 2
|pages = 102–106
|isbn = 5946281720}}</ref> For comparison, in [[alcohol]]s the C–O–H angle is about 110°; in [[ether]]s, the C–O–C angle is 120°. The [[moment of inertia]] about the principal axes are ''I<sub>A</sub>'' = 32.921×10<sup>−40</sup> g·cm², ''I<sub>B</sub>'' = 37.926×10<sup>−40</sup> g·cm² and ''I<sub>C</sub>'' = 59.510×10<sup>−40</sup> g·cm².<ref>{{cite journal
|author = Cunningham G. L., Levan W. I., Gwinn W. D.
|title = The Rotational Spectrum of Ethylene Oxide
|doi=10.1103/PhysRev.74.1537
|journal = Phys. Rev.
|year = 1948
|volume = 74| page = 1537
}}</ref> The [[dipole moment]] at a temperature in the range 17–176 °C is 6.26×10<sup>−30</sup> C·m.<ref>{{cite web
|date = 1 April 2009
|url = http://chemanalytica.com/book/novyy_spravochnik_khimika_i_tekhnologa/12_obshchie_svedeniya/6106
|title = The dipole moments of certain substances
|publisher = ChemAnalitica.com
|accessdate = 2009-09-21}}</ref> 

The relative instability of the carbon-oxygen bonds in the molecule is revealed by the comparison in the table of the energy required to break two C–O bonds in the ethylene oxide or one C–O bond in [[ethanol]] and [[dimethyl ether]]:<ref>{{cite book
|title = Energy of chemical bonds. Ionization potentials and electron affinity
|editor =Kondrat'ev, VN 
|publisher = Nauka
|year = 1974
|pages = 77–78}}</ref>
{| Class = "wikitable" style="text-align:center"
 ! Reaction
 ! ΔH°<sub>298</sub>, kJ/mol
 ! Method
|-
| '''(C<sub>2</sub>H<sub>4</sub>)O → C<sub>2</sub>H<sub>4</sub> + O''' (cleavage of two bonds)
|354.38
|Calculated, from atomic enthalpies
|-
|'''[[Ethanol|C<sub>2</sub>H<sub>5</sub>OH]] → C<sub>2</sub>H<sub>5</sub> + OH''' (breaking one bond)
|405.85
|Electron impact
|-
|'''[[Dimethyl ether|CH<sub>3</sub>OCH<sub>3</sub>]] → CH<sub>3</sub>O + CH<sub>3</sub>''' (breaking one bond)
|334.72
|Calculated using enthalpies of radicals formation
 |}

This instability determines the chemical activity of ethylene oxide and explains the ease of opening its cycle in [[addition reaction]]s (see [[Ethylene oxide#Chemical properties|Chemical properties]]).

==Physical properties==
Ethylene oxide is a colorless gas at 25 °C and is a mobile liquid at 0 °C – viscosity of liquid ethylene oxide at 0 °C is about 5.5 times lower than that of water. The gas has a characteristic sweet odor of ether, noticeable when its concentration in air exceeds 500 ppm.<ref name="atsdr">{{cite web
|url = http://www.atsdr.cdc.gov/MHMI/mmg137.html
|title = Medical Management Guidelines for Ethylene Oxide
|work = Medical Management Guidelines (MMGs)
|publisher = Agency for Toxic Substances and Disease Registry
|accessdate = 2009-09-29}}</ref> Ethylene oxide is readily soluble in water, [[ethanol]], [[diethyl ether]] and many organic solvents.<ref>{{cite web
|url = http://slovari.yandex.ru/~%D0%BA%D0%BD%D0%B8%D0%B3%D0%B8/%D0%91%D0%A1%D0%AD/%D0%AD%D1%82%D0%B8%D0%BB%D0%B5%D0%BD%D0%B0%20%D0%BE%D0%BA%D0%B8%D1%81%D1%8C/
|title = Ethylene oxide
|publisher = [[Great Soviet Encyclopedia]]
|accessdate = 2009-09-25
|language =Russian}}</ref>

Main thermodynamical constants are:<ref name="sch1">{{cite web| date = 1 April 2009 года| url= http://chemanalytica.com/book/novyy_spravochnik_khimika_i_tekhnologa/12_obshchie_svedeniya/6084
|title = Термодинамические показатели органических соединений
|publisher = ChemAnalitica.com
|accessdate = 2009-09-21}}</ref>
* Standard molar [[heat capacity]], C<sub>p</sub>° = 48.19 J/(mol·K);
* Standard [[enthalpy]] of formation, ΔH°<sub>298</sub> = –51.037 kJ/mol;
* Standard [[entropy]], S°<sub>298</sub> = 243.4 J/(mol·K);
* [[Gibbs free energy]], ΔG°<sub>298</sub> = –11.68 kJ/mol;
* [[Heat of combustion]], ΔH<sub>c</sub>° = –1306 kJ/mol.<ref name="en">{{cite book
|chapter= Ethylene oxide|title=Chemical encyclopedia|editor=Knunyants, I. L.|year=1988|pages=990–991|volume=5}}</ref>

The [[surface tension]] of liquid ethylene oxide, at the interface with its own steam, is 35.8 mJ/m<sup>2</sup> at –50.1 °C and 27.6 mJ/m<sup>2</sup> at –0.1 °C.<ref>{{cite web
|date = 1 April 2009
|url = http://chemanalytica.com/book/novyy_spravochnik_khimika_i_tekhnologa/12_obshchie_svedeniya/6118
|title = Surface tension of liquefied gas at the border with its own steam
|publisher = ChemAnalitica.com
|accessdate = 2009-09-21}}</ref> 

The boiling point increases with the vapor pressure as follows:<ref>{{cite web
|date = 1 April 2009
|url = http://chemanalytica.com/book/novyy_spravochnik_khimika_i_tekhnologa/12_obshchie_svedeniya/6061
|title = boiling point or sublimation (°C) organic matter in the vapor pressure above 101.3 kPa
|publisher = ChemAnalitica.com
|accessdate = 2009-09-21
}}</ref> 
57.7 (2 atm), 83.6 (5 atm) and 114.0 (10 atm). 

[[Viscosity]] decreases with temperature with the values of 0.577 kPa·s at –49.8 °C, 0.488 kPa·s at –38.2 °C, 0.394 kPa·s at –21.0 °C and 0.320 kPa·s at 0 °C.<ref>{{cite web
|date = 1 April 2009
|url = http://chemanalytica.com/book/novyy_spravochnik_khimika_i_tekhnologa/12_obshchie_svedeniya/6112
|title = viscosity of organic compounds
|publisher = ChemAnalitica.com
|accessdate = 2009-09-21
}}</ref> 

Between –91 °C and 10.5 °C, vapor pressure ''p'' (in mmHg) varies with temperature (T in °C) as lg ''p'' = 6.251 – 1115.1/(244.14 + T).<ref>{{cite web
|date = 1 April 2009
|url = http://chemanalytica.com/book/novyy_spravochnik_khimika_i_tekhnologa/12_obshchie_svedeniya/6063
|title = vapor pressure of organic compounds
|publisher = ChemAnalitica.com
|accessdate = 2009-09-21
}}</ref> 

{| Class = "wikitable" style="text-align:center"
|+Properties of liquid ethylene oxide<ref name="ect" /> 
 ! Temperature, °C
 ! Steam pressure, kPa
 ! Enthalpy of the liquid,<br/> J/g
 ! Enthalpy of vaporization,<br/> J/g
 ! Density, kg/L
 ! [[Heat capacity]], J/(kg·K)
 ! [[Thermal conductivity]], W/(m·K)
|-
| –40 °C
| 8.35
| 0
| 628.6
| 0.9488
| 1878
| 0.20
|-
| –20 °C
| 25.73
| 38.8
| 605.4
| 0.9232
| 1912
| 0.18
|-
| 0 °C
| 65.82
| 77.3
| 581.7
| 0.8969
| 1954
| 0.16
|-
| 20 °C
| 145.8
| 115.3
| 557.3
| 0.8697
| 2008
| 0.15
|-
| 40 °C
| 288.4
| 153.2
| 532.1
| 0.8413
| 2092
| 0.14
|-
| 60 °C
| 521.2
| 191.8
| 505.7
| 0.8108
| 2247
| 0.14
|-
| 80 °C
| 875.4
| 232.6
| 477.4
| 0.7794
| 2426
| 0.14
|-
| 100 °C
| 1385.4
| 277.8
| 445.5
| 0.7443
| 2782
| 0.13
|-
| 120 °C
| 2088
| 330.4
| 407.5
| 0.7052
| 3293
| N/A* 
|-
| 140 °C
| 3020
| 393.5
| 359.4
| 0.6609
| 4225
| N/A
|-
| 160 °C
| 4224
| 469.2
| 297.1
| 0.608
| N/A
| N/A
|-
| 180 °C
| 5741
| 551.2
| 222.5
| 0.533
| N/A
| N/A
|-
| 195.8 °C
| 7191
| N/A
| N/A
| N/A
| N/A
| N/A
 |}
<nowiki>*</nowiki>N/A – data not available.

{| Class = "wikitable" style="text-align:center"
|+Properties of ethylene oxide vapor <ref name="ect" />
 ! Temperature, K
 ! Entropy, J/(mol·K)
 ! Heat of formation, kJ/mol
 ! Free energy of formation, kJ/mol
 ! Viscosity Pa·s
 ! Thermal conductivity, W/(m·K)
 ! Heat capacity, J/(mol·K)
|-
| 298
| 242.4
| –52.63
| –13.10
| N/A
| N/A
| 48.28
|-
| 300
| 242.8
| –52.72
| –12.84
| 9.0
| 0.012
| 48.53
|-
| 400
| 258.7
| –56.53
| 1.05
| 13.5
| 0.025
| 61.71
|-
| 500
| 274.0
| –59.62
| 15.82
| 15.4
| 0.038
| 75.44
|-
| 600
| 288.8
| –62.13
| 31.13
| 18.2
| 0.056
| 86.27
|-
| 700
| 302.8
| –64.10
| 46.86
| 20.9
| 0.075
| 95.31
|-
| 800
| 316.0
| –65.61
| 62.80
| N/A
| 0.090
| 102.9
|}
<nowiki>*</nowiki>N/A – data not available.

==Chemical properties==
Ethylene oxide readily reacts with various compounds, breaking a C–O bond and opening the cycle. Its typical reactions are with nucleophiles which proceed via the [[Nucleophilic substitution|'''S<sub>N</sub>2''']] mechanism both in acidic (weak nucleophiles: water, alcohols) and alkaline media (strong nucleophiles: OH<sup>–</sup>, RO<sup>–</sup>, NH<sub>3</sub>, RNH<sub>2</sub>, RR'NH, etc.).<ref name="traven" /> The general reaction scheme is

: [[File:Eoractions.png|500px|Mechanism of reaction with ethylene oxide]]

and more specific reactions are described below. 

===Addition of water and alcohols===
Aqueous solutions of ethylene oxide are rather stable and can exist for a long time without any noticeable chemical reaction, but adding a small amount of acid, such as strongly diluted [[sulfuric acid]], immediately leads to the formation of [[ethylene glycol]], even at room temperature:

: (CH<sub>2</sub>CH<sub>2</sub>)O + H<sub>2</sub>O → HO–CH<sub>2</sub>CH<sub>2</sub>–OH

The reaction also occurs in the gas phase, in the presence of a [[phosphoric acid]] salt as a catalyst.<ref name="oe3">{{cite book
|chapter= Chapter III. Review of the individual reactions of ethylene oxide
|title = Ethylene oxide
|editor=PV Zimakova and Mr. O. Dymenta
| location = M.
|publisher = Khimiya
|year = 1967
|pages = 90–120}}</ref>

The reaction is usually carried out at about 60 °C with a large excess of water, in order to prevent the reaction of the formed ethylene glycol with ethylene oxide that would form di- and [[triethylene glycol]]:<ref>{{cite web
|url = http://www.chemguide.co.uk/organicprops/alkenes/epoxyethane.html
|title = Epoxyethane (Ethylene Oxide)
|work = Alkenes menu
|publisher = Chemguide
|accessdate = 2009-10-05
}}</ref>
 
:2 (CH<sub>2</sub>CH<sub>2</sub>)O + H<sub>2</sub>O → HO–CH<sub>2</sub>CH<sub>2</sub>–O–CH<sub>2</sub>CH<sub>2</sub>–OH

:3 (CH<sub>2</sub>CH<sub>2</sub>)O + H<sub>2</sub>O → HO–CH<sub>2</sub>CH<sub>2</sub>–O–CH<sub>2</sub>CH<sub>2</sub>–O–CH<sub>2</sub>CH<sub>2</sub>–OH

The use of alkaline catalysts may lead to the formation of [[polyethylene glycol]]:

:n (CH<sub>2</sub>CH<sub>2</sub>)O + H<sub>2</sub>O → HO–(–CH<sub>2</sub>CH<sub>2</sub>–O–)<sub>n</sub>–H

Reactions with [[alcohol]]s proceed similarly yielding ethylene glycol ethers:

: (CH<sub>2</sub>CH<sub>2</sub>)O + C<sub>2</sub>H<sub>5</sub>OH → HO–CH<sub>2</sub>CH<sub>2</sub>–OC<sub>2</sub>H<sub>5</sub>

:2 (CH<sub>2</sub>CH<sub>2</sub>)O + C<sub>2</sub>H<sub>5</sub>OH → HO–CH<sub>2</sub>CH<sub>2</sub>–O–CH<sub>2</sub>CH<sub>2</sub>–OC<sub>2</sub>H<sub>5</sub>

Reactions with lower alcohols occur less actively than with water and require more severe conditions, such as heating to 160 °C and pressurizing to 3 MPa and adding an acid or alkali catalyst.

Reactions of ethylene oxide with fatty alcohols proceed in the presence of [[sodium]] metal, [[sodium hydroxide]] or [[boron trifluoride]] and are used for the synthesis of [[surfactants]].<ref name="oe3" />

===Addition of carboxylic acids and their derivatives===
Reactions of ethylene oxide with [[carboxylic acid]]s in the presence of a catalyst results in incomplete and with [[anhydrides]] in complete glycol esters:

: (CH<sub>2</sub>CH<sub>2</sub>)O + CH<sub>3</sub>COOH → HO–CH<sub>2</sub>CH<sub>2</sub>–OCOCH<sub>3</sub>

: (CH<sub>2</sub>CH<sub>2</sub>)O + (CH<sub>3</sub>CO)<sub>2</sub>O → CH<sub>3</sub>COO–CH<sub>2</sub>CH<sub>2</sub>–OCOCH<sub>3</sub>

The addition of acid [[amide]]s proceeds similarly:

: (CH<sub>2</sub>CH<sub>2</sub>)O + CH<sub>3</sub>CONH<sub>2</sub> → HO–CH<sub>2</sub>CH<sub>2</sub>–NHCOCH<sub>3</sub>

Addition of ethylene oxide to higher carboxylic acids is carried out at elevated temperatures (typically 140–180 °C) and pressure (0.3–0.5 MPa) in an inert atmosphere, in presence of an alkaline catalyst (concentration 0.01–2%), such as hydroxide or carbonate of sodium or potassium.<ref>{{cite book
|title = Nonionic surfactants: organic chemistry
|editor=N. M. van Os
|publisher = CRC Press
|year = 1998
|pages = 129–131|url=http://books.google.com/?id=YoZ6CjYNLoQC&pg=PA129
|isbn = 9780824799977}}</ref> The carboxylate ion acts as [[nucleophile]] in the reaction:

:RCOOH + OH<sup>–</sup> → RCOO<sup>–</sup> + H<sub>2</sub>O

: (CH<sub>2</sub>CH<sub>2</sub>)O + RCOO<sup>–</sup> → RCOOCH<sub>2</sub>CH<sub>2</sub>O<sup>–</sup>

:RCOOCH<sub>2</sub>CH<sub>2</sub>O<sup>–</sup> + RCOOH → RCOOCH<sub>2</sub>CH<sub>2</sub>OH + RCOO<sup>–</sup>

===Adding ammonia and amines===
Ethylene oxide reacts with [[ammonia]] forming a mixture of mono-, di- and triethanolamine. The reaction is stimulated by adding a small amount of water.

: (CH<sub>2</sub>CH<sub>2</sub>)O + NH<sub>3</sub> → HO–CH<sub>2</sub>CH<sub>2</sub>–NH<sub>2</sub>

:2 (CH<sub>2</sub>CH<sub>2</sub>)O + NH<sub>3</sub> → HO–CH<sub>2</sub>CH<sub>2</sub>)<sub>2</sub>NH<sub>2</sub>

:3 (CH<sub>2</sub>CH<sub>2</sub>)O + NH<sub>3</sub> → HO–CH<sub>2</sub>CH<sub>2</sub>)<sub>3</sub>N

Similarly proceed the reactions with primary and secondary amines:

: (CH<sub>2</sub>CH<sub>2</sub>)O + RNH<sub>2</sub> → HO–CH<sub>2</sub>CH<sub>2</sub>–NHR

Dialkylamino ethanols can further react with ethylene oxide, forming amino polyethylene glycols:<ref name="ect" />

:n (CH<sub>2</sub>CH<sub>2</sub>)O + R<sub>2</sub>NCH<sub>2</sub>CH<sub>2</sub>OH → R<sub>2</sub>NCH<sub>2</sub>CH<sub>2</sub>O–(–CH<sub>2</sub>CH<sub>2</sub>O–)<sub>n</sub>–H

Trimethylamine reacts with ethylene oxide in the presence of water, forming [[choline]]:<ref>{{cite book
|author = Petrov, AA, Balian HV, Troshchenko AT
|chapter= Chapter 12. Amino alcohol
|title = Organic chemistry| editor= Stadnichuk
|edition = 5|location = St. Petersburg.
|year = 2002
|page = 286
|isbn = 5819400674}}</ref>

: (CH<sub>2</sub>CH<sub>2</sub>)O + (CH<sub>3</sub>)<sub>3</sub>N + H<sub>2</sub>O → [HOCH<sub>2</sub>CH<sub>2</sub>N (CH<sub>3</sub>)<sub>3</sub>]<sup>+</sup>OH<sup>–</sup>

Aromatic primary and secondary amines also react with ethylene oxide, forming the corresponding arylamino alcohols.

===Halide addition===
Ethylene oxide readily reacts with aqueous solutions of [[hydrochloric acid|hydrochloric]], [[hydrobromic acid|hydrobromic]] and [[hydroiodic acid]]s to form [[halohydrin]]s. The reaction occurs easier with the last two acids:

: (CH<sub>2</sub>CH<sub>2</sub>)O + HCl → HO–CH<sub>2</sub>CH<sub>2</sub>–Cl

The reaction with these acids competes with the acid-catalyzed hydration of ethylene oxide; therefore, there is always a by-product of ethylene glycol with an admixture of diethylene glycol. For a cleaner product, the reaction is conducted in the gas phase or in an organic solvent.

Ethylene fluorohydrin is obtained differently, by boiling [[hydrogen fluoride]] with a 5–6% solution of ethylene oxide in [[diethyl ether]]. The ether normally has a water content of 1.5–2%; in absence of water, ethylene oxide polymerizes.<ref>{{cite book
|author = William A. Sheppard, Clay M. Sharts
|title = Organic Fluorine Chemistry
|publisher = W.A. Benjamin
|year = 1969
|page= 98
|isbn = 0805387900}}</ref>

Halohydrins can also be obtained by passing ethylene oxide through aqueous solutions of metal halides:<ref name="oe3" />
 
:2 (CH<sub>2</sub>CH<sub>2</sub>)O + CuCl<sub>2</sub> + 2 H<sub>2</sub>O → 2 HO–CH<sub>2</sub>CH<sub>2</sub>–Cl + Cu(OH)<sub>2</sub>↓

===Metalorganic addition===
Interaction of ethylene oxide with organomagnesium compounds, which are [[Grignard reaction|Grignard reagents]], can be regarded as [[nucleophilic substitution]] influenced by [[carbanion]] organometallic compounds. The final product of the reaction is a primary alcohol:

: <math>\mathsf{(CH_2CH_2)O+RMgBr}\rightarrow\mathsf{R\!\!-\!\!CH_2CH_2\!\!-\!\!OMgBr\ \xrightarrow{H_2O}\ R\!\!-\!\!CH_2CH_2\!\!-\!\!OH}</math>

Similar mechanism is valid for other organometallic compounds, such as alkyl lithium:

: <math>\mathsf{(CH_2CH_2)O+RLi}\rightarrow\mathsf{R\!\!-\!\!CH_2CH_2\!\!-\!\!OLi\ \xrightarrow{H_2O}\ R\!\!-\!\!CH_2CH_2\!\!-\!\!OH}</math>

===Other addition reactions===
====Addition of hydrogen cyanide====
Ethylene oxide easily reacts with the [[hydrogen cyanide]] forming ethylene cyanohydrin:

: (CH<sub>2</sub>CH<sub>2</sub>)O + HCN → HO–CH<sub>2</sub>CH<sub>2</sub>–CN

A slightly chilled (10–20 °C) aqueous solution of [[calcium cyanide]] can be used instead of HCN:<ref>{{cite journal
|url = http://www.orgsyn.org/orgsyn/pdfs/cv1p0256.pdf
|title = Ethylene cyanohydrin
|journal = Organic Syntheses|volume= 1|page=256|year=1941}}</ref>

:2 (CH<sub>2</sub>CH<sub>2</sub>)O + Ca(CN)<sub>2</sub> + 2 H<sub>2</sub>O → 2 HO–CH<sub>2</sub>CH<sub>2</sub>–CN + Ca(OH)<sub>2</sub>

Ethylene cyanohydrin easily loses water, producing [[acrylonitrile]]:

:HO–CH<sub>2</sub>CH<sub>2</sub>–CN → CH<sub>2</sub>=CH–CN + H<sub>2</sub>O

====Addition of hydrogen sulfide and mercaptans====
When reacting with the [[hydrogen sulfide]], ethylene oxide forms 2-mercaptoethanol and thiodiglycol, and with alkylmercaptans it produces 2-alkyl mercaptoetanol:

: (CH<sub>2</sub>CH<sub>2</sub>)O + H<sub>2</sub>S → HO–CH<sub>2</sub>CH<sub>2</sub>–HS

:2 (CH<sub>2</sub>CH<sub>2</sub>)O + H<sub>2</sub>S → (HO–CH<sub>2</sub>CH<sub>2</sub>)<sub>2</sub>S

: (CH<sub>2</sub>CH<sub>2</sub>)O + RHS → HO–CH<sub>2</sub>CH<sub>2</sub>–SR

The excess of ethylene oxide with an aqueous solution of hydrogen sulfide leads to the tris-(hydroxyethyl) sulfonyl hydroxide:

:3 (CH<sub>2</sub>CH<sub>2</sub>)O + H<sub>2</sub>S → [(HO–CH<sub>2</sub>CH<sub>2</sub>)<sub>3</sub>S<sup>+</sup>]OH<sup>–</sup>

====Addition of nitrous and nitric acids====
Reaction of ethylene oxide with aqueous solutions of [[barium nitrite]], [[calcium nitrite]], [[magnesium nitrite]], [[zinc nitrite]] or [[sodium nitrite]] leads to the formation of 2-nitroethanole:<ref>{{cite journal
|url = http://www.orgsyn.org/orgsyn/pdfs/CV5P0833.pdf
|title = 2-Nitroethanol
|journal = Organic Syntheses|volume=5|page=833|year=1973}}</ref>

:2 (CH<sub>2</sub>CH<sub>2</sub>)O + Ca(NO<sub>2</sub>)<sub>2</sub> + 2 H<sub>2</sub>O → 2 HO–CH<sub>2</sub>CH<sub>2</sub>–NO<sub>2</sub> + Ca(OH)<sub>2</sub>

With [[nitric acid]], ethylene oxide forms mono- and [[Ethylene glycol dinitrate|dinitroglycol]]s:<ref>{{cite book
|author = Orlova, EY
|title = Chemistry and technology of high explosives: Textbook for high schools
|edition = 3
|publisher = Khimiya
|year = 1981
|page= 278}}</ref>

: <math>\mathsf{(CH_2CH_2)O+HNO_3}\rightarrow\mathsf{HO\!\!-\!\!CH_2CH_2\!\!-\!\!ONO_2\ \xrightarrow[-H_2O]{+\ HNO_3}\ O_2NO\!\!-\!\!CH_2CH_2\!\!-\!\!ONO_2}</math>

====Reaction with compounds containing active methylene groups====
In the presence of alcoholates, reactions of ethylene oxide with compounds containing active methylene group leads to the formation of [[gamma-Butyrolactone|butyrolactone]]s:<ref>{{cite book
|author = Vogel A.I.
|title = Vogel's Textbook of practical organic chemistry
|edition = 5|location = UK
|publisher = Longman Scientific & Technical
|year = 1989
|page = 1088
|isbn = 0582462363}}</ref>

: [[File:2-ACETYLBUTYROLACTONE-SYNTHESIS.png|550px|Synthesis of 2-acetylbutyrolactone]]

====Additions with aromatic compounds====
Ethylene oxide enters into the [[Friedel-Crafts reaction]] with benzene to form [[phenethyl alcohol]]:

: [[File:Oxirane+benzene.png|400px|Friedel-Crafts reaction with ethylene oxide]]

[[Styrene]] can be obtained in one stage if this reaction is conducted at elevated temperatures (315–440 °C) and pressures (0.35–0.7 MPa), in presence of an aluminosilicate catalyst.<ref>{{cite web
|url = http://www.freepatentsonline.com/4443643.pdf
|title = United States Patent 4443643. Reaction of benzene with ethylene oxide to produce styrene
|accessdate = 2009-10-13}}</ref>

====Synthesis of crown ethers====
A series of polynomial [[heterocyclic compound]]s, known as [[crown ether]]s, can be synthesized with ethylene oxide. One method is the cationic cyclopolymerization of ethylene oxide, limiting the size of the formed cycle:<ref name="crown">{{cite book
|author = Hiraoka M.
|title = Crown Compounds. Their Characteristics and Applications
|publisher = Kodansha
|year = 1982
|pages= 33–34
|isbn =4061394444}}</ref>

:n (CH<sub>2</sub>CH<sub>2</sub>)O → (–CH<sub>2</sub>CH<sub>2</sub>–O–)<sub>n</sub>

To suppress the formation of other linear polymers the reaction is carried out in a highly dilute solution.<ref name="crown" />

Reaction of ethylene oxide with [[sulfur dioxide]] in the presence of caesium salts leads to the formation of an 11-membered heterocyclic compound which has the complexing properties of crown ethers:<ref name>{{cite journal
|author = Roesky H. W., Schmidt H. G.
|title = Reaction of Ethylene Oxide with Sulfur Dioxide in the Presence of Cesium Ions: Synthesis of 1,3,6,9,2 λ <sup>4</sup>-Tetraoxathia-2-cycloundecanone
| journal = Angewandte Chemie International Edition
|year = 1985|doi=10.1002/anie.198506951
|volume = 24
|page = 695
}}</ref>

: [[File:Tetraoxathia-2-cycloundecanone.png|350px|Synthesis of 1,3,6,9,2 λ <sup>4</sup>-Tetraoksatia-2-tsikloundekanona]]

===Isomerization===
When ethylene oxide is heated to about 400 °C, or to 150–300 °C in the presence of a catalyst ([[aluminium oxide|Al<sub>2</sub>O<sub>3</sub>]], [[phosphoric acid|H<sub>3</sub>PO<sub>4</sub>]], etc.), it [[isomerization|isomerizes]] into [[acetaldehyde]]:<ref name="petrov">{{cite book
|author = Petrov, AA, Balian HV, Troshchenko AT
|chapter= Chapter 4. Ethers
|title = Organic chemistry| edition=5
|location = St. Petersburg.
|year = 2002
|pages = 159–160
|isbn = 5819400674}}</ref>

: <math>\mathsf{(CH_2CH_2)O\ \xrightarrow{200\ ^oC,\ Al_2O_3}\ CH_3CHO}</math>

The radical mechanism was proposed by Sidney W. Benson to explain this reaction in the gas phase; it comprises the following stages:<ref name="benson">{{cite journal
|author = Benson S. W.
|title = Pyrolysis of Ethylene Oxide. A Hot Molecule Reaction
|doi=10.1063/1.1729851| journal = The Journal of Chemical Physics
|year = 1964
|volume = 40
| page = 105
}}</ref>

1) (CH<sub>2</sub>CH<sub>2</sub>)O ↔ •CH<sub>2</sub>CH<sub>2</sub>O• → CH<sub>3</sub>CHO*

2) CH<sub>3</sub>CHO* → CH<sub>3</sub>• + CHO•

3) CH<sub>3</sub>CHO* + M → CH<sub>3</sub>CHO + M*

In reaction 3), '''M''' refers to the wall of the reaction vessel or to a heterogeneous catalyst. 
The moiety CH<sub>3</sub>CHO* represents a short-lived (lifetime of 10<sup>–8.5</sup> seconds), activated molecule of acetaldehyde. Its excess energy is about 355.6 kJ/mol, which exceeds by 29.3 kJ/mol the [[binding energy]] of the C-C bond in acetaldehyde.<ref name="benson" />

In absence of a catalyst, the thermal isomerization of ethylene oxide is never selective and apart from acetaldehyde yields significant amount of by-products (see section [[Ethylene oxide#Thermal decomposition|Thermal decomposition]]).<ref name="oe2"/>

===Reduction reaction===
Ethylene oxide can be hydrogenated into ethanol in the presence of a catalyst, such as [[nickel]], [[platinum]], [[palladium]],<ref name="oe2" /> [[borane]]s, [[lithium aluminium hydride]] and some other [[hydride]]s.<ref name="reduction">{{cite book
|author = Hudlický M.
|title = Reductions in Organic Chemistry
|location = Chichester
|publisher = Ellis Horwood Limited
|year = 1984
|page = 83
|isbn = 0853123454}}</ref>

: <math>\mathsf{(CH_2CH_2)O+H_2\ \xrightarrow{80\ ^oC,\ Ni}\ C_2H_5OH}</math>

Conversely, with some other catalysts, ethylene oxide may be ''reduced'' by hydrogen to ethylene with the yield up to 70%. The reduction catalysts include mixtures of zinc dust and [[acetic acid]], of lithium aluminium hydride with [[titanium trichloride]] (the reducing agent is actually [[Titanium(II) chloride|titanium dichloride]], formed by the reaction between LiAlH<sub>4</sub> and TiCl<sub>2</sub>) and of [[iron(III) chloride]] with [[butyllithium]] in [[tetrahydrofuran]].<ref name="reduction" />

: <math>\mathsf{(CH_2CH_2)O+H_2\ \xrightarrow{Zn\ +\ CH_3COOH}\ CH_2\!\!=\!\!CH_2+H_2O}</math>

===Oxidation===
Ethylene oxide can further be oxidized, depending on the conditions, to [[glycolic acid]] or [[carbon dioxide]]:

: <math>\mathsf{(CH_2CH_2)O+O_2\ \xrightarrow{AgNO_3}\ HOCH_2COOH}</math>

Deep gas-phase reactor oxidation of ethylene oxide at 800–1000 K and a pressure of 0.1–1 MPa yields a complex mixture of products containing O<sub>2</sub>, H<sub>2</sub>, [[carbon monoxide|CO]], [[carbon dioxide|CO<sub>2</sub>]], [[methane|CH<sub>4</sub>]], [[acetylene|C<sub>2</sub>H<sub>2</sub>]], [[ethylene|C<sub>2</sub>H<sub>4</sub>]], [[ethane|C<sub>2</sub>H<sub>6</sub>]], [[propylene|C<sub>3</sub>H<sub>6</sub>]], [[propane|C<sub>3</sub>H<sub>8</sub>]] and [[acetaldehyde|CH<sub>3</sub>CHO]].<ref>{{cite journal
|author = Dagaut P., Voisin D., Cathonnet M., Mcguinness M., Simmie J. M.
|title = The oxidation of ethylene oxide in a jet-stirred reactor and its ignition in shock waves
|journal = Combustion and Flame
|year = 1996
|volume = 156
| pages = 62–68
}}</ref>

===Dimerization===
In the presence of acid catalysts, ethylene oxide can be dimerized into [[dioxane]]:

: [[File:Dioxane-synthesis.png|250px|Synthesis of dioxane]]

The reaction mechanism is as follows:<ref name="oe2" />

: [[File:Dioxan-HerstellungCZ.png|650px|Mechanism of dimerization]]

The dimerization reaction is not selective, and there are always by-products, such as [[acetaldehyde]] (due to [[Ethylene oxide#Isomerization|isomerization]]). The selectivity and speed of dimerization can be increased by adding a catalyst, such as platinum, platinum-palladium or [[iodine]] with [[sulfolan]]; however, 2-methyl-1,3-[[dioxolane]] is formed as a side product in the last case.<ref>{{cite web
|url = http://www.freepatentsonline.com/3998848.pdf
|title = United States Patent 3998848. Cyclodimerization of ethylene oxide}}</ref>

===Polymerization===
Liquid ethylene oxide can form a [[polyethyleneglycol]]s. The polymerization can proceeds via radical and ionic mechanisms, but only the latter has a wide practical application.<ref name="glycol">{{cite book
|author = Dyment, ON, Kazanskii, KS, Miroshnikov AM
|title = glycol and other derivatives of ethylene oxide and propylene
|editor = ON Dymenta
|publisher = Khimiya
|year = 1976
|pages = 214–217}}</ref> [[Cationic polymerization]] of ethylene oxide is assisted by protonic acids ([[perchloric acid|HClO<sub>4</sub>]], [[hydrochloric acid|HCl]]), Lewis acids ([[Tin(IV) chloride|SnCl<sub>4</sub>]], [[boron trifluoride|BF<sub>3</sub>]], etc.), [[organometallic compound]]s or more complex reagents:<ref name="glycol" />

: <math>\mathsf{n(CH_2CH_2)O\ \xrightarrow{SnCl_4}\ (-\!CH_2CH_2\!\!-\!\!O\!-)_n}</math>

The reaction mechanism is as follows.<ref name="poly">{{cite book
|title = Polymeric materials encyclopedia
|editor= Joseph C. Salamone
|publisher = CRC Press
|year = 1996
|volume = 8
|pages = 6036–6037
|isbn = 9780849324703}}</ref> At the first stage, the catalyst (MX<sub>m</sub>) is initiated by alkyl-or acylhalogen or by compounds with active hydrogen atoms, usually water, alcohol or glycol:

:MX<sub>m</sub> + ROH → MX<sub>m</sub>RO<sup>–</sup>H<sup>+</sup>

The resulting active complex reacts with ethylene oxide via the '''S<sub>N</sub>2''' mechanism:

: (CH<sub>2</sub>CH<sub>2</sub>)O + MX<sub>m</sub>RO<sup>–</sup>H<sup>+</sup> → (CH<sub>2</sub>CH<sub>2</sub>)O•••H<sup>+</sup>O<sup>–</sup>RMX<sub>m</sub>

: (CH<sub>2</sub>CH<sub>2</sub>)O•••H<sup>+</sup> O<sup>–</sup>RMX<sub>m</sub> → HO–CH<sub>2</sub>CH<sub>2</sub><sup>+</sup> + MX<sub>m</sub>RO<sup>–</sup><sub>2</sub>

:HO–CH<sub>2</sub>CH<sub>2</sub><sup>+</sup> + n (CH<sub>2</sub>CH<sub>2</sub>)O → HO–CH<sub>2</sub>CH<sub>2</sub>–(O–CH<sub>2</sub>CH<sub>2</sub>)<sub>n</sub><sup>+</sup>

The chain breaks as

:HO–CH<sub>2</sub>CH<sub>2</sub>–(O–CH<sub>2</sub>CH<sub>2</sub>)<sub>n</sub><sup>+</sup> + MX<sub>m</sub>RO<sup>–</sup> → HO–CH<sub>2</sub>CH<sub>2</sub>–(O–CH<sub>2</sub>CH<sub>2</sub>)<sub>n</sub>–OR + MX<sub>m</sub>

:H(O–CH<sub>2</sub>CH<sub>2</sub>)<sub>n</sub>–O–CH<sub>2</sub>–CH<sub>2</sub><sup>+</sup> + MX<sub>m</sub>RO<sup>–</sup> → H(O–CH<sub>2</sub>CH<sub>2</sub>)<sub>n</sub>–O–CH=CH<sub>2</sub> + MX<sub>m</sub> + ROH

[[Anionic polymerization]] of ethylene oxide is assisted by bases, such as [[alcoholates]] [[hydroxide]]s, [[carbonate]]s or other compounds of alkali or [[alkaline earth metal]]s.<ref name="glycol" /> The reaction mechanism is as follows:<ref name="poly" />

: (CH<sub>2</sub>CH<sub>2</sub>)O + RONa → RO–CH<sub>2</sub>CH<sub>2</sub>–O<sup>–</sup>Na<sup>+</sup>

:RO–CH<sub>2</sub>CH<sub>2</sub>–O<sup>–</sup>Na<sup>+</sup> + n (CH<sub>2</sub>CH<sub>2</sub>)O → RO–(CH<sub>2</sub>CH<sub>2</sub>–O)<sub>n</sub>–CH<sub>2</sub>CH<sub>2</sub>–O<sup>–</sup>Na<sup>+</sup>

:RO–(CH<sub>2</sub>CH<sub>2</sub>–O)<sub>n</sub>–CH<sub>2</sub>CH<sub>2</sub>–O<sup>–</sup>Na<sup>+</sup> → RO–(CH<sub>2</sub>CH<sub>2</sub>–O)<sub>n</sub>–CH=CH<sub>2</sub> + NaOH

:RO–(CH<sub>2</sub>CH<sub>2</sub>–O)<sub>n</sub>–CH<sub>2</sub>CH<sub>2</sub>–O<sup>–</sup>Na<sup>+</sup> + H<sub>2</sub>O → RO–(CH<sub>2</sub>CH<sub>2</sub>–O)<sub>(n+1)</sub>OH + NaOH

===Thermal decomposition===
Ethylene oxide is relatively stable to heating – in the absence of a catalyst, it does not dissociate up to 300 °C, and only above 570 °C there is a major [[exothermic]] decomposition, which proceeds through the radical mechanism.<ref name="oe2">{{cite book
|chapter= Chapter II. Chemical properties of ethylene oxide
|title = Ethylene oxide
|editor=PV Zimakova and Mr. O. Dymenta
|publisher = Khimiya
|year = 1967
|pages = 57–85}}</ref> The first stage involves [[Ethylene oxide#Isomerization|isomerization]], however high temperature accelerated the radical processes. They result in a gas mixture containing acetaldehyde, ethane, ethyl, methane, hydrogen, carbon dioxide, [[ketene]] and [[formaldehyde]].<ref>{{cite journal
|author = Neufeld L.M., Blades A.T.
|title = The Kinetics of the Thermal Reactions of Ethylene Oxide
|journal = Canadian Journal of Chemistry
|year = 1963|url=http://article.pubs.nrc-cnrc.gc.ca/ppv/RPViewDoc?issn=1480-3291&volume=41&issue=12&startPage=2956|doi=10.1139/v63-434
|volume = 41
|page = 2956}}</ref> High-temperature [[pyrolysis]] (830–1200 K) at elevated pressure in an inert atmosphere leads to a more complex composition of the gas mixture, which also contains [[acetylene]] and [[propane]].<ref name="Lifshitz">{{cite journal|author = Lifshitz A., Ben-Hamou H.
|title = Thermal reactions of cyclic ethers at high temperatures. 1. Pyrolysis of ethylene oxide behind reflected shocks
|journal = The Journal of Physical Chemistry
|year = 1983|doi=10.1021/j100233a026
|volume = 87
|page = 1782
}}</ref> Contrary to the isomerization, initiation of the chain occurs mainly as follows:<ref name="Lifshitz" />

: (CH<sub>2</sub>CH<sub>2</sub>)O → •CH<sub>2</sub>CH<sub>2</sub>O• → CH<sub>2</sub>O + CH<sub>2</sub>:

When carrying the thermal decomposition of ethylene oxide in the presence of transition metal compounds as catalysts, it is possible not only to reduce its temperature, but also to have [[ethyl]] as the main product, that is to reverse the ethylene oxide synthesis reaction. 

===Other reactions===
[[Thiocyanate]] ions or [[thiourea]] transform ethylene oxide into [[thiirane]]s (ethylene sulfides):<ref>{{cite book
|author = Gilchrist T.
|title = Heterocyclic Chemistry
|publisher = Pearson Education
|year = 1985
|pages = 411–412
|isbn = 8131707938}}</ref>

: (CH<sub>2</sub>CH<sub>2</sub>)O + (NH<sub>2</sub>)<sub>2</sub>C=S → (CH<sub>2</sub>CH<sub>2</sub>)S + (NH<sub>2</sub>)<sub>2</sub>C=O

: [[File:Thiirane-synthesis.jpg|550px|mechanism synthesis thiiranes of ethylene oxide under the influence of thiocyanate ion]]

Reaction of [[phosphorus pentachloride]] with ethylene oxide produces [[ethylene dichloride]]:<ref name="oe3" />

: (CH<sub>2</sub>CH<sub>2</sub>)O + PCl<sub>5</sub> → Cl–CH<sub>2</sub>CH<sub>2</sub>–Cl + POCl<sub>3</sub>

Other dichloro derivatives of ethylene oxide can be obtained by combined action of [[sulfuryl chloride]] (SOCl<sub>2</sub>) and [[pyridine]] and of [[triphenylphosphine]] and [[carbon tetrachloride]].<ref name="march2">
{{cite book
|author = Michael Smith, Michael B. Smith, Jerry March
|title = Advanced organic chemistry. Reactions, Mechanisms and Structure
|publisher = Wiley-Interscience
|year = 2007|url=http://books.google.com/?id=JDR-nZpojeEC
|isbn =0471720917}}</ref>

[[Phosphorus trichloride]] reacts with ethylene oxide forming chloroethyl esters of phosphorous acid:<ref name="oe3" />

: (CH<sub>2</sub>CH<sub>2</sub>)O + PCl<sub>3</sub> → Cl–CH<sub>2</sub>CH<sub>2</sub>–OPCl<sub>2</sub>

:2 (CH<sub>2</sub>CH<sub>2</sub>)O + PCl<sub>3</sub> → (Cl–CH<sub>2</sub>CH<sub>2</sub>–O)<sub>2</sub>PCl

:3 (CH<sub>2</sub>CH<sub>2</sub>)O + PCl<sub>3</sub> → Cl–CH<sub>2</sub>CH<sub>2</sub>–O)<sub>3</sub>P

The reaction product of ethylene oxide with [[acyl chloride]]s in the presence of [[sodium iodide]] is a complex iodoethyl ether:<ref name="march2" />

: (CH<sub>2</sub>CH<sub>2</sub>)O + RCOCl + NaI → RC(O)–OCH<sub>2</sub>CH<sub>2</sub>–I + NaCl

Heating ethylene oxide to 100 °C with [[carbon dioxide]], in a non-polar solvent in the presence of ''bis''-(triphenylphosphine)-nickel(0) results in [[ethylene carbonate]]:<ref>{{ cite book|author = L. Fieser, M. Fieser
|title = Reagents for Organic Synthesis
|publisher =Wiley
|volume = 7|year=1979
|page= 545
|isbn =9780471029182}}</ref>

: [[File:Ethylene-carbonate-syn.png|380px|Synthesis of ethylene carbonate]]

In industry, a similar reaction is carried out at high pressure and temperature in the presence of quaternary ammonium or phosphonium salts as a catalyst.<ref>{{cite book
|author = Sheldon RA
|title= Chemicals from synthesis gas: catalytic reactions of CO and, Volume 2
|url=http://books.google.com/?id=s1_rjRUlu1EC&pg=PA193|page=193
|publisher = Springer
|year = 1983
|isbn=9027714894}}</ref>

Reaction of ethylene oxide with [[formaldehyde]] at 80–150 °C in the presence of a catalyst leads to the formation of [[dioxolane|1,3-dioxolane]]:<ref name="fiser">{{cite book
|author = L. Fieser, M. Fieser
|title = Reagents for Organic Synthesis
|publisher = Wiley
|year = 1977|isbn=9780471258735
|volume = 6
|page= 197}}</ref>

: [[File:Dioxolane.png|330px|Synthesis of 1,3-dioxolane]]

Substituting formaldehyde by other aldehydes or ketones results in a 2-substituted 1,3-dioxolane (yield: 70–85%, catalyst: tetraetilammoniybromid).<ref name="fiser" />

Catalytic [[hydroformylation]] of ethylene oxide results in hydroxypropanal and further in propane-1,3-diol:<ref>{{cite web
|url = http://www.freepatentsonline.com/20030032845.pdf
|title = United States Patent 20030032845. Hydroformylation of ethylene oxide}}</ref>

: <math>\mathsf{(CH_2CH_2)O+CO+H_2}\rightarrow\mathsf{CHO\!\!-\!\!CH_2CH_2\!\!-\!\!OH\ \xrightarrow{+H_2}\ HO\!\!-\!\!CH_2CH_2CH_2\!\!-\!\!OH}</math>

==Laboratory synthesis==
===Dehydrochlorination of ethylene and its derivatives===
Dehydrochlorination of [[2-chloroethanol]], developed by Wurtz back in 1859, still remains one of the most common laboratory methods of producing ethylene oxide:

:Cl–CH<sub>2</sub>CH<sub>2</sub>–OH + NaOH → (CH<sub>2</sub>CH<sub>2</sub>)O + NaCl + H<sub>2</sub>O

The reaction is carried out at elevated temperature, and beside [[sodium hydroxide]] or [[potassium hydroxide]], [[calcium hydroxide]], [[barium hydroxide]], [[magnesium hydroxide]] or [[carbonate]]s of alkali or alkaline earth metals can be used.<ref name="oe5">{{cite book
|chapter= Chapter V. Producing ethylene oxide through ethylene
|title = Ethylene oxide
|editor=PV Zimakova and O. Dymenta
|publisher = Khimiya
|year = 1967
|pages = 155–182}}</ref>

Chloroethanol, in turn, is synthesized using one of the following methods:<ref name="oe5" />

By reacting ethylene glycol hydrochloric acid:

:OH–CH<sub>2</sub>CH<sub>2</sub>–OH + HCl → OH–CH<sub>2</sub>CH<sub>2</sub>–Cl + H<sub>2</sub>O

By reacting ethylene with [[hypochlorous acid]]:

:CH<sub>2</sub>=CH<sub>2</sub> + HOCl → OH–CH<sub>2</sub>CH<sub>2</sub>–Cl

or by chlorination of ethylene

:CH<sub>2</sub>=CH<sub>2</sub> + Cl<sub>2</sub> + H<sub>2</sub>O → OH–CH<sub>2</sub>CH<sub>2</sub>–Cl + HCl

Another convenient and old method of ethylene oxide synthesis is reaction of an [[alkali]] with chloroethyl acetate:<ref name="oeII">{{cite book
|chapter = Part II. Synthesis of ethylene oxide. Overview of reactions of formation of ethylene oxide and other α-oxides
|title = Ethylene oxide
|editor=PV Zimakova and Mr. O. Dymenta
|publisher = Khimiya
|year = 1967
|pages = 145–153}}</ref>

:Cl–CH<sub>2</sub>CH<sub>2</sub>–OCOCH<sub>3</sub> + 2 KOH → (CH<sub>2</sub>CH<sub>2</sub>)O + KCl + CH<sub>3</sub>COOK + H<sub>2</sub>O

With a high yield (90%) ethylene oxide can be produced by reacting [[calcium oxide]] with ethyl hypochlorite; substituting calcium by other alkaline earth metals reduces the reaction yield:<ref name="oeII" />

:2 CH<sub>3</sub>CH<sub>2</sub>–OCl + CaO → 2 (CH<sub>2</sub>CH<sub>2</sub>)O + CaCl<sub>2</sub> + H<sub>2</sub>O

In turn, ethylhypochlorite is synthesized as follows:

:Cl<sub>2</sub> + NaOH + CH<sub>3</sub>CH<sub>2</sub>OH → CH<sub>3</sub>CH<sub>2</sub>OCl + NaCl + H<sub>2</sub>O

===Direct oxidation of ethylene by peroxy acids===
Ethylene can be directly oxidized into ethylene oxide using [[peroxy acid]]s, for example, [[peroxybenzoic acid|peroxybenzoic]] or ''meta''-chloro-peroxybenzoic acid:<ref>{{cite book
|author = McMurry J.
|title = Organic chemistry
|edition = 7
|publisher = Thomson
|year = 2008
|page= 661
|isbn = 0495112585}}</ref>

: [[File:Epoxides-synthesis.png|500px|Oxidation of ethylene by peroxy acids]]

Oxidation by peroxy acids is efficient for higher alkenes, but not for ethylene. The above reaction is slow and has low yield, therefore it is not used in the industry.<ref name="oeII" />

===Other preparative methods===
Other synthesis methods include<ref name="oeII" /> reaction of diiodo ethane with [[silver oxide]]:

:I–CH<sub>2</sub>CH<sub>2</sub>–I + Ag<sub>2</sub>O → (CH<sub>2</sub>CH<sub>2</sub>)O + 2 AgI

and decomposition of ethylene carbonate at 200–210 °C in the presence of [[hexachloroethane]]:

: [[File:Ethylenecarbonate-distruction.png|350px|Decomposition of ethylene carbonate]]

==Industrial synthesis==
===History===
Commercial production of ethylene oxide dates back to 1914 when [[BASF]] built the first factory which used the chlorohydrin process (reaction of ethylene chlorohydrin with calcium hydroxide). The chlorohydrin process was unattractive for several reasons, including low efficiency and loss of valuable chlorine into [[calcium chloride]].<ref>{{cite journal
|author = Norris J.F.
|title = The Manufacture of War Gases in Germany
|journal = Journal of Industrial and Engineering Chemistry
|year = 1919
|volume = 11
|page = 817}}</ref> More efficient direct oxidation of ethylene by air was invented by Lefort in 1931 and in 1937 [[Union Carbide]] opened the first plant using this process. It was further improved in 1958 by Shell Oil Co. by replacing air with oxygen and using elevated temperature of 200–300 °C and pressure (1–3 MPa).<ref name = "industrial"/> This more efficient routine accounted for about half of ethylene oxide production in the 1950s in the U.S., and after 1975 it completely replaced the previous methods.<ref name = "industrial" >{{cite book
|author = Weissermel K., Arpe H-J.
|title = Industrial organic chemistry
| edition = 4
|location = Weinheim
|publisher = Wiley-VCH
|year = 2003
|pages = 145–148
|isbn = 9783527305780}}</ref>

===Chlorohydrin process of production of ethylene oxide===
Although the chlorohydrin process is almost entirely superseded in the industry by the direct oxidation of ethylene, the knowledge of this method is still important for educational reasons and because it is still used in the production of [[propylene oxide]].<ref>{{cite web
|date = February 1985
|url = http://www.sriconsulting.com/PEP/Public/Reports/Phase_84/RP002D/
|title = Process Economics Program Report 2D
|work = PEP Report
|publisher = SRI Consulting
|accessdate = 2009-11-19}}</ref> The process consists of three major steps: synthesis of ethylene chlorohydrin, dehydrochlorination of ethylene chlorohydrin to ethylene oxide and purification of ethylene oxide. Those steps are carried continuously. In the first column, hypochlorination of ethylene is carried out as follows:<ref name="uk">{{cite book
|author = Yukelson II
|title = The technology of basic organic synthesis
|publisher = Khimiya
|year = 1968
|pages = 554–559}}</ref>

:Cl<sub>2</sub> + H<sub>2</sub>O → HOCl + HCl

:CH<sub>2</sub>=CH<sub>2</sub> + HOCl → OH–CH<sub>2</sub>CH<sub>2</sub>–Cl

:CH<sub>2</sub>=CH<sub>2</sub> + Cl<sub>2</sub> → Cl–CH<sub>2</sub>CH<sub>2</sub>–Cl

To suppress the conversion of ethylene into the [[ethylene dichloride]] (the last reaction), the concentration of ethylene is maintained at about 4–6%, and the solution is heated by steam to the boiling point.<ref name="uk" />

Next, aqueous solution of ethylene chlorohydrin enters the second column, where it reacts with a 30% solution of calcium hydroxide at 100 °C:<ref name="uk" />

:2 OH–CH<sub>2</sub>CH<sub>2</sub>–Cl + Ca(OH)<sub>2</sub> → 2 (CH<sub>2</sub>CH<sub>2</sub>)O + CaCl<sub>2</sub> + H<sub>2</sub>O

The produced ethylene oxide is purified by [[rectification]]. The chlorohydrin process allows to reach 95% conversion of ethylene chlorohydrin. The yield of ethylene oxide is about 80% of the theoretical value; for 1 ton of ethylene oxide, about 200&nbsp;kg of ethylene dichloride is produced.<ref name="uk" />

===Direct oxidation of ethylene===
====Usage in the global industry====
Direct oxidation of ethylene was patented by Lefort in 1931. This method was repeatedly modified for industrial use, and at least four major variations are known. They all use oxidation by oxygen or air and a silver-based catalyst, but differ in the technological details and hardware implementations.<ref name="eos">{{cite book
|chapter = Catalitic Oxidation of Olefins
|title = Advances in catalysis and related subjects
| editor= D.D. Eley, H. Pines, P.B. Weisz
| location = New York
|publisher = Academic Press Inc
|year = 1967
|volume = 17
|pages = 156–157}}</ref>

[[Union Carbide]] (currently a division of [[Dow Chemical Company]]) was the first company to develop the direct oxidation process. Since 1994, it uses the so-called METEOR process ('''M'''ost ''' E'''ffective '''T'''echnology for '''E'''thylene '''O'''xide '''R'''eactions) which is characterized by high productivity, low initial capital investment and low operating costs. The method is the exclusive property of the company; it is used only at its own plants and accounts for about 20% of the global ethylene oxide production.<ref name="cmpa">{{cite book
|author = Bloch H. P., Godse A.
|title = Compressors and modern process applications|publisher = John Wiley and Sons
|year = 2006
|pages = 295–296
|isbn = 9780471727927
}}</ref> 

A similar production method was developed by Scientific Design Co., but it received wider use because of the licensing system – it accounts for 25% of the world's production and for 75% of world's licensed production of ethylene oxide.<ref name = "cmpa"/><ref>{{cite web
|url = http://www.scidesign.com/Business/EO%20-%20EG%20Process/EO_EG_Process.htm
|title = Ethylene Oxide/Ethylene Glycol Process
|work = Process Licensing and Engineering
|publisher = Scientific Design Company
|accessdate = 2009-10-03}}</ref> A proprietary variation of this method is used by Japan Catalytic Chemical Co., which adapted synthesis of both ethylene oxide and ethylene glycol in a single industrial complex.

A different modification was developed Shell International Chemicals BV. Their method is rather flexible with regard to the specific requirements of specific industries; it is characterized by high selectivity with respect to the ethylene oxide product and long lifetime of the catalyst (3 years). It accounts for about 40% of global production.<ref name="cmpa" />

Older factories typically use air for oxidation whereas newer plants and processes, such as METEOR and Japan Catalytic, favor oxygen.<ref>{{cite book
|author = Chauvel A., Lefebvre G.
|title = Petrochemical processes 2. Major Oxygenated, Chlorinated and Nitrated Derivatives
|edition = 2
|location = Paris
|publisher = Editions Technip
|year = 1989
|volume = 2
|page= 4
|isbn = 2710805634}}</ref>

====Chemistry and kinetics of the direct oxidation process====
Formally, the direct oxidation process is expressed by the following equation:

: <math>\mathsf{2CH_2\!\!=\!\!CH_2+O_2\ \xrightarrow{Ag}\ 2(CH_2CH_2)O}</math>

However, significant yield of carbon dioxide and water is observed in practice, which can be explained by the complete oxidation of ethylene or ethylene oxide:

:CH<sub>2</sub>=CH<sub>2</sub> + 3 O<sub>2</sub> → 2 CO<sub>2</sub> + 2 H<sub>2</sub>O

:2 (CH<sub>2</sub>CH<sub>2</sub>)O + 5 O<sub>2</sub> → 4 CO<sub>2</sub> + 4 H<sub>2</sub>O

The process of heterogeneous catalytic oxidation of ethylene was studied by P. A. Kilty and W. M. H. Sachtler, who suggested the following mechanism:<ref name="kilty">{{cite journal
|author = Kilty P. A., Sachtler W. M. H.
|title = The mechanism of the selective oxidation of ethylene to ethylene oxide
|doi=10.1080/01614947408079624
|journal = Catalysis Reviews: Science and Engineering
|year = 1974
|volume = 10
|pages = 1–16
}}</ref>

:O<sub>2</sub> + 4 Ag(adj) → 4 Ag + 2 O<sup>2–</sup>(ads)
:O<sub>2</sub> + Ag → Ag<sup>+</sup> + O<sub>2</sub><sup>–</sup>
:O<sub>2</sub><sup>–</sup>(ads) + CH<sub>2</sub>=CH<sub>2</sub> → (CH<sub>2</sub>CH<sub>2</sub>)O + O(ads)
:6 O (ads) + CH<sub>2</sub>=CH<sub>2</sub> → 2 CO<sub>2</sub> + 2 H<sub>2</sub>O

Here (ads) refers to particles adsorbed on the catalyst surface and (adj) to particles of silver, directly adjacent to the oxygen atoms.

Thus the overall reaction is expressed as 

:7 CH<sub>2</sub>=CH<sub>2</sub> + 6 O<sub>2</sub> → 6 (CH<sub>2</sub>CH<sub>2</sub>)O + 2 CO<sub>2</sub> + 2 H<sub>2</sub>O

and the maximum degree of conversion of ethylene to ethylene oxide is 6/7 or 85.7%.<ref name="kilty" />

The catalyst for the reaction is metallic silver deposited on various matrixes, including [[pumice]], [[silica gel]], various [[silicate]]s and [[aluminosilicate]]s, [[alumina]] and [[silicon carbide]], and activated by certain additives ([[antimony]], [[bismuth]], [[barium peroxide]], etc.).<ref name = "lebedev">{{cite book
|author = Lebedev, N.N.
|title = Chemistry and technology of basic organic and petrochemical synthesis
|edition = 4 
|publisher = Khimiya
|pages = 420–424
|isbn = 5724500086}}</ref> The process temperature was optimized as 220–280 °C. Lower temperatures reduce the activity of the catalyst, and higher temperatures promote the complete oxidation of ethylene thereby reducing the yield of ethylene oxide. Elevated pressure of 1–3 MPa increases the productivity of the catalyst and facilitates absorption of ethylene oxide from the reacting gases.<ref name="lebedev" />

Whereas oxidation by air is still being used, oxygen (> 95% purity) is preferred for several reasons, such as higher molar yield of ethylene oxide (75–82% for oxygen vs. 63–75% for air), higher reaction rate (no gas dilution) and no need of separating nitrogen in the reaction products.<ref name="ect" /><ref>{{cite book
|author = Gunardson H.
|title = Industrial gases in petrochemical processing
|location = New York
|publisher = Marcel Dekker, Inc.
|year = 1998
|pages = 131–132
|isbn = 0824799089}}</ref>

===World production of ethylene oxide===
The world production of ethylene oxide was 19 million tonnes in 2008 and 18 million tonnes in 2007.<ref name="sri">{{cite web
|date = January 2009
|url = http://www.sriconsulting.com/WP/Public/Reports/eo/
|title = Ethylene Oxide
|work = WP Report
|publisher = SRI Consulting
|accessdate = 2009-09-29}}</ref> This places ethylene oxide 14th most produced organic chemical, whereas the most produced one was ethylene with 113 million tonnes.<ref>{{cite web
|date = January 2009
|url = http://www.sriconsulting.com/WP/Public/Reports/ethylene/
|title = Ethylene
|work = WP Report
|publisher = SRI Consulting
|accessdate = 2009-09-29}}</ref> SRI Consulting forecasted the growth of consumption of ethylene oxide of 4.4% per year during 2008–2013 and 3% from 2013 to 2018.<ref name="sri" />

In 2004, the global production of ethylene oxide by region was as follows:<ref name="iars" />
{| Class = "wikitable" width = 95%
 ! Align = "center" width = 40%|Region
 ! Align = "center" width = 30%|Number of major producers
 ! Align = "center" width = 30%|Production, thousand tonnes
|-
 |'''North America'''<br/> [[United States]]<br/> [[Canada]]<br/> [[Mexico]]
|align = "center"|<br/> 10<br/> 3<br/> 3
|align = "center"|<br/>4009<br/> 1084<br/> 350
|-
 |'''South America'''<br/> [[Brazil]]<br/> [[Venezuela]]
|align = "center"|<br/> 2<br/> 1
|align = "center"|<br/>312<br/> 1982
|-
 |'''Europe'''<br/> [[Belgium]]<br/> [[France]]<br/> [[Germany]] <br/> [[Netherlands]]<br/> [[Spain]]<br/> [[Turkey]]<br/> [[United Kingdom]] <br/> [[Eastern Europe]]
|align = "center"|<br/> 2<br/> 1<br/> 4<br/> 2<br/> 1<br/> 1<br/> 1<br/> no data
|align = "center"|<br/>770<br/> 215 <br/>995<br/> 460 <br/>100<br/> 115<br/>300<br/> 950
|-
 |'''Middle East'''<br/> [[Iran]]<br/> [[Kuwait]]<br/> [[Saudi Arabia]]
|align = "center"|<br/> 2<br/> 1<br/> 2
|align = "center"|<br/> 201 <br/>350<br/> 1781
|-
 |'''Asia'''<br/> [[China]]<br/> [[Taiwan]]<br/> [[India]]<br/> [[Indonesia]]<br/> [[Japan]]<br/> [[Malaysia]]<br/> [[South Korea]]<br/> [[Singapore]]
|align = "center"|<br/> No data<br/> 4<br/>> 2<br/> 1<br/> 4<br/> 1<br/> 3<br/> 1
|align = "center"|<br/> 1354<br/>820<br/> 488 <br/>175<br/>949<br/> 385 <br/>740<br/> 80
 |}

The world's largest producers of ethylene oxide are [[Dow Chemical Company]] (3–3.5 million tonnes in 2006<ref name="aq">{{cite web
|author = Devanney M. T.
|date = April 2007
|url = http://www.sriconsulting.com/PEP/Reports/Phase<sub>2</sub>009/RP2I/
|title = Ethylene Oxide
|work = SEH Peport
|publisher = SRI Consulting
|accessdate = 2009-11-19}}</ref>), [[SABIC|Saudi Basic Industries]] (2000–2500 tonnes in 2006<ref name="aq" />), [[Royal Dutch Shell]] (1.328 million tonnes in 2008–2009<ref>{{cite web
|url = http://www.shell.com/home/content/chemicals/products_services/our_products/ethylene_oxide_glycols/ethylene_oxide/manufacturing_locations/ethylene_oxide_singapore/ethylene_oxide_singapore.html
|title = Ethylene Glycols (Singapore) Pte Ltd, Singapore
|work = Manufacturing locations
|publisher = Shell Chemicals
|accessdate = 2009-10-12}}</ref><ref>{{cite web
|url = http://www.m-kagaku.co.jp/english/corporate/index.html
|title = Overview
|publisher = Mitsubishi Chemical Corporation
|accessdate = 2009-10-12}}</ref><ref>{{cite web
|url = http://www.shell.com/home/content/chemicals/products_services/our_products/ethylene_oxide_glycols/ethylene_oxide/manufacturing_locations/geismar/ethylene_oxide_geismar.html
|title = Shell Chemical LP – Geismar, United States of America
|work = Manufacturing locations
|publisher = Shell Chemicals
|accessdate = 2009-10-12}}</ref><ref>{{cite web
|url = http://www.shell.com/home/content/chemicals/products_services/our_products/ethylene_oxide_glycols/ethylene_oxide/manufacturing_locations/moerdijk/ethylene_oxide_moerdijk.html
|title = Shell Nederland Chemie BV – Moerdijk, Netherlands
|work = Manufacturing locations
|publisher = Shell Chemicals
|accessdate = 2009-10-12}}</ref><ref>{{cite web
|url = http://www.cnoocshell.com/home/topic.aspx?topic=38
|title = Plants/Facilities and Capacity
|publisher = CNOOC and Shell Petrochemicals Company Limited
|accessdate = 2009-10-12}}</ref>), [[BASF]] (1.175 million tonnes in 2008–2009<ref>{{cite web
|url = http://www.report.basf.com/2008/en/subjects/products/chemicals.html
|title = Segment Chemicals – Products
|publisher = BASF
|accessdate = 2009-10-12}}</ref>), [[China Petrochemical Corporation]] (~1000 tonnes in 2006<ref name="aq" />), [[Formosa Plastics]] (~1 million tonnes in 2006<ref name="aq" />) and [[Ineos]] (0.92 million tonnes in 2008–2009).<ref>{{cite web
|url = http://www.ineosoxide.com/21-Ethylene_Oxide__EO_.htm
|title = Ethylene Oxide (EO)
|publisher = Ineos Oxide
|accessdate = 2009-10-12}}</ref>

==Applications==
[[File:Eo-usesEN.png|thumb|350px|Global industrial use of ethylene oxide in 2007.<ref name="iars" />]]

Ethylene oxide is one of the most important raw materials used in the large-scale chemical production. Most ethylene oxide is used for synthesis of [[ethylene glycol]]s, including diethylene glycol and triethylene glycol, that accounts for up to 75% of global consumption. Other important products include ethylene glycol ethers, ethanolamines and ethoxylates. Among glycols, ethylene glycol is used as [[antifreeze]], in the production of [[polyester]] and [[polyethylene terephthalate]] (PET – raw material for plastic bottles), liquid coolants and solvents. Polyethyleneglycols are used in perfumes, cosmetics, pharmaceuticals, [[lubricant]]s, [[paint thinner]]s and [[plasticizer]]s. Ethylene glycol ethers are part of brake fluids, detergents, solvents, lacquers and paints. Other products of ethylene oxide. Ethanolamines are used in the manufacture of soap and detergents and for purification of natural gas. Ethoxylates are reaction products of ethylene oxide with higher alcohols, acids or amines. They are used in the manufacture of detergents, surfactants, [[emulsifier]]s and [[dispersant]]s.<ref>{{cite web
|url =http://www.shell.com/home/content/chemicals/products_services/our_products/ethylene_oxide_glycols/ethylene_oxide/product_overview/ethylene_oxide_overview.html
|title = Ethylene oxide product overview
|work = Ethylene oxide
|publisher = Shell Chemicals
|accessdate = 2009-10-08}}</ref>

Whereas synthesis of ethylene glycols is the major application of ethylene oxide, its percentage varies greatly depending on the region: from 44% in the [[Western Europe]], 63% in [[Japan]] and 73% in [[North America]] to 90% in the rest of [[Asia]] and 99% in [[Africa]].<ref>{{cite web
|url = http://www.icis.com/v2/chemicals/9075772/ethylene-oxide/uses.html
|title = Ethylene Oxide (EO) Uses and Market Data
|work = Chemical Intelligence
|publisher = Chemical Industry News & Intelligence (ICIS.com)
|accessdate = 2009-10-08}}</ref>

====Production of ethylene glycol====
Ethylene glycol is industrially produced by non-catalytic hydration of ethylene oxide at a temperature of 200 °C and a pressure of 1.5–2 MPa:<ref name="MEG">{{cite book
|chapter= Ethylene
|title = Chemical Encyclopedia
| editor = IL Knunyants
|publisher = "Soviet encyclopedia"
|year = 1988
|volume = 5
|pages = 984–985}}</ref>

: (CH<sub>2</sub>CH<sub>2</sub>)O + H<sub>2</sub>O → HOCH<sub>2</sub>CH<sub>2</sub>OH

By-products of the reaction are diethylene glycol, triethylene glycol and polyglycols with the total of about 10%, which are separated from the ethylene glycol by distillation at reduced pressure.<ref>{{cite book
|title = Handbook of Detergents, Part F: Production
| editor=Uri Zoller, Paul Sosis
|publisher = CRC Press
|year = 2008
|pages = 518–521
|isbn = 9780824703493}}</ref>

Another synthesis method is the reaction of ethylene oxide and CO<sub>2</sub> (temperature 80–120 °C and pressure of 5.2 MPa) yielding [[ethylene carbonate]] and its subsequent hydrolysis with decarboxylation:<ref name = "MEG" />

: <math>\mathsf{(CH_2CH_2)O+CO_2}\rightarrow\mathsf{(O\!\!-\!\!CH_2CH_2\!\!-\!\!O)C\!\!=\!\!O\ \xrightarrow[-CO_2]{+H_2O}\ HOCH_2CH_2OH}</math>

Modern technologies of production of ethylene glycol include the following.<ref>{{cite web
|author = Syed Naqvi|date = September 2009
|url = http://www.sriconsulting.com/PEP/Reports/Phase<sub>2</sub>009/RP2I/
|title = Process Economics Program Report 2I
|work = PEP Peport
|publisher = SRI Consulting
|accessdate = 2009-10-20}}</ref> Shell OMEGA technology (Only Mono-Ethylene Glycol Advantage) is a two-step synthesis of ethylene carbonate using a [[phosphonium]] halide as a catalyst. The glycol yield is 99–99.5%, with other glycols practically absent. The main advantage of the process is production of pure ethylene glycol without the need for further purification. The first commercial plant which uses this method was opened in 2008 in South Korea.<ref>[http://www.shell.com/home/content/chemicals/innovation/leading_edge_technology/omega_delivers_ethylene_glycol/omega_delivers_ethylene_glycol.html OMEGA delivers for ethylene glycol makers], Shell</ref> Dow METEOR (Most Effective Technology for Ethylene Oxide Reactions) is an integrated technology for producing ethylene oxide and its subsequent hydrolysis into ethylene glycol. The glycol yield is 90–93%. The main advantage of the process is relative simplicity, using fewer stages and less equipment.

====Production of glycol ethers====
The major industrial esters of mono-, di- and triethylene glycols are methyl, ethyl and normal butyl ethers, as well as their acetates and phthalates. The synthesis involves reaction of the appropriate [[alcohol]] with ethylene oxide:<ref>{{cite book
|title = Encyclopedia of chemical processing and design
|editor=John J. McKetta, William A. Cunningham
|location = New York
|publisher = Marcel Dekker, Inc
|year = 1984
|volume = 20
|pages = 259–260
|isbn = 0824724704}}</ref>

: (CH<sub>2</sub>CH<sub>2</sub>)O + ROH → HOCH<sub>2</sub>CH<sub>2</sub>OR

: (CH<sub>2</sub>CH<sub>2</sub>)O + HOCH<sub>2</sub>CH<sub>2</sub>OR → HOCH<sub>2</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>2</sub>OR

: (CH<sub>2</sub>CH<sub>2</sub>)O + HOCH<sub>2</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>2</sub>OR → HOCH<sub>2</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>2</sub>OR

The reaction of monoesters with an acid or its anhydride leads to the formation of the esters:

:CH<sub>3</sub>COOH + HOCH<sub>2</sub>CH<sub>2</sub>OR → ROCH<sub>2</sub>CH<sub>2</sub>OCOCH<sub>3</sub> + H<sub>2</sub>O

====Production of ethanolamines====
In the industry, [[ethanolamine]]s (mono-, di- and triethanolamines) are produced by reacting [[ammonia]] and ethylene oxide in anhydrous medium at a temperature of 40–70 °C and pressure of 1.5–3.5 MPa:<ref>{{cite web
|url = http://www.himtek.ru/cgi-bin/index.cgi?IdS=18&IdP=9&Lang=0
|title = Technology of ethanolamine
|work = Technology
|publisher = Himtek Engineering
|accessdate = 2009-10-22}}</ref>

:CH<sub>2</sub>CH<sub>2</sub>)O + NH<sub>3</sub> → HOCH<sub>2</sub>CH<sub>2</sub>NH<sub>2</sub>

:2 (CH<sub>2</sub>CH<sub>2</sub>)O + NH<sub>3</sub> → (HOCH<sub>2</sub>CH<sub>2</sub>)<sub>2</sub>NH

:3 (CH<sub>2</sub>CH<sub>2</sub>)O + NH<sub>3</sub> → (HOCH<sub>2</sub>CH<sub>2</sub>)<sub>3</sub>N

All three ethanolamines are produced in the process, while ammonia and part of methylamine are recycled. The final products are separated by vacuum [[distillation]]. Hydroxyalkylamines are produced in a similar process:

:CH<sub>2</sub>CH<sub>2</sub>)O + RNH<sub>2</sub> → HOCH<sub>2</sub>CH<sub>2</sub>NHR

:2 (CH<sub>2</sub>CH<sub>2</sub>)O + RNH<sub>2</sub> → (HOCH<sub>2</sub>CH<sub>2</sub>)<sub>2</sub>NR

Monosubstituted products are formed by reacting a large excess of amine with ethylene oxide in presence of water and at a temperature below 100 °C. Disubstituted products are obtained with a small excess of ethylene oxide, at a temperature of 120–140 °C and a pressure of 0.3–0.5 MPa.<ref>{{cite book
|author = Chekalin MA, Passet BV, Ioffe BA
|title = The technology of organic dyes and intermediate products: A manual for technical
|edition = 2|publisher = Khimiya
|year = 1980
|page= 185}}</ref>

====Production of ethoxylates====
<!-- [[File:Alkoxylation process.png|thumb|left|550px|Schematic image of the production ethoxylates <ref name="buss" />]] -->
Industrial production of ethoxylates is realized by a direct reaction of higher alcohols, acids or amines with ethylene oxide in the presence of an alkaline catalyst at a temperature of 120–180 °C. Modern plants producing ethoxylates are usually based on the BUSS LOOP reactors technology,<ref name="buss">{{cite book
|title = Chemistry and technology of surfactants
|editor= R. J. Farn
|publisher = Blackwell Publishing
|year = 2006
|page = 133
|isbn = 1405126965}}</ref> which is based on a three-stage continuous process. In the first stage, the initiator or catalyst of the reaction and the feedstock are fed into the container, where they are mixed, heated and vacuum dried. Then reaction is carried out in a special insulated reactor in an inert atmosphere (nitrogen) to prevent a possible explosion of ethylene oxide. Finally, the reaction mixture is neutralized, degassed and purified.<ref>{{cite web
|url = http://www.buss-ct.com/e/reaction_technology/alkoxylation.php?navid=36
|title = Alkoxylation
|work = BUSS LOOP Reactor
|publisher = Buss ChemTech AG
|accessdate = 2009-10-21}}</ref>

====Production of acrylonitrile====
Currently, most [[acrylonitrile]] (90% in 2008) is produced by the SOHIO method, which is based on the catalytic oxidation of [[propylene]] in the presence of ammonia and bismuth phosphomolybdate. However, until 1960 a key production process was addition of [[hydrogen cyanide]] to ethylene oxide, followed by dehydration of the resulting [[cyanohydrin]]:<ref>{{cite web
|url = http://acswebcontent.acs.org/landmarks/landmarks/soh/soh_process.html
|title = The Sohio Acrylonitrile Process
|publisher = National Historic Chemical Landmarks
|accessdate = 2009-10-22}}</ref><ref>{{cite web
|date = 1 April 2009
|url = http://chemanalytica.com/book/novyy_spravochnik_khimika_i_tekhnologa/06_syre_i_produkty_promyshlennosti_organicheskikh_i_neorganicheskikh_veshchestv_chast_II/5015
|title = 13.1.3.5. Oxidative ammonolysis of hydrocarbons
|publisher = ChemAnalitica.com
|accessdate = 2009-10-22}}</ref>:

: <math>\mathsf{(CH_2CH_2)O+HCN}\rightarrow\mathsf{HOCH_2CH_2CN\ \xrightarrow[-H_2O]\ CH_2\!\!=\!\!CH\!\!-\!\!CN }</math>

Addition of hydrocyanic acid to ethylene oxide is carried out in the presence of a catalyst ([[sodium hydroxide]] and [[diethylamine]]), and dehydration of cyanohydrin occurs in the gas phase upon the catalytic action of [[aluminium oxide]].<ref>
{{cite book
|author = Andreas F., Grabe K.
|title = Propylenchemie|publisher =Akademie-Verlag
|year = 1969
|pages = 117–118}}</ref>

===Other uses===
The direct use of ethylene oxide accounts for only 0.05% (2004 data) of its global production.<ref name="iars" /> Ethylene oxide is used as a [[Fumigation|fumigant]] and disinfecting agent, as a mixture with carbon dioxide (8.5–80% of ethylene oxide), nitrogen or [[dichlorodifluoromethane]] (12% ethylene oxide). It is applied for gas-phase sterilization of medical equipment and instruments, packaging materials and clothing, surgical and scientific equipment;<ref name="iars">{{cite book
|title = 1,3-Butadiene, Ethylene Oxide and Vinyl Halides (Vinyl Fluoride, Vinyl Chloride and Vinyl Bromide)
| edition = IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Vol. 97
|location = Lyon
|publisher = International Agency for Research on Cancer
|year = 2008
|pages = 185–287
|isbn = 9789283212973}}</ref> for processing of storage facilities (tobacco, packages of grain, sacks of rice, etc.), clothing, furs and valuable documents.<ref name="ew">{{cite web
|url = http://www.environmentwriter.org/resources/backissues/chemicals/ethylene_oxide.htm
|title = Ethylene oxide
|work = Chemical Backgrounders Index
|publisher = The Environment Writer
|accessdate = 2009-09-29}}</ref>

Ethylene oxide is also used as a flame retardant, accelerator of maturation of tobacco leaves and [[fungicide]].<ref name="ew" /> Ethylene oxide is also used as a main component of [[thermobaric weapon]]s (fuel-air explosives).<ref name=e1>{{cite book|url=http://books.google.com/?id=ZzlNgS70OHAC&pg=PA136|page=136|title=Weapons of mass destruction: an encyclopedia of worldwide policy, technology, and history, Volume 2|author=Eric Croddy, James J. Wirtz|isbn=1851094903|publisher=ABC-CLIO|year=2005}}</ref><ref name=e2>{{cite book|url=http://books.google.com/?id=ATiYCfo1VcEC&pg=PA142|page=142|title=Explosives|author=Rudolf Meyer, Josef Köhler, Axel Homburg|publisher=Wiley-VCH|year=2007|isbn=3527316566}}</ref><ref>{{cite web
|url = http://www.freepatentsonline.com/4132170.pdf
|title = United States Patent 4132170. Fuel-air type bomb
|accessdate = 2009-10-22}}</ref>

==Identification of ethylene oxide==

The simplest qualitative reaction for ethylene oxide uses its property to precipitate insoluble hydroxides of metals when it is passed through aqueous solutions of their salts, for example

:2 (CH<sub>2</sub>CH<sub>2</sub>)O + MnCl<sub>2</sub> + 2 H<sub>2</sub>O → 2 HO–CH<sub>2</sub>CH<sub>2</sub>–Cl + Mn(OH)<sub>2</sub>↓

Similarly, ethylene oxide is detected by the bright pink color of the indicator when passing air through aqueous solutions of some salts of sodium or potassium (chlorides, iodides, thiosulfates, etc.) with the addition of [[phenolphthalein]]:<ref name="oe4">{{cite book
|chapter = Chapter IV Methods of analysis of ethylene oxide
|title = Ethylene oxide
|editor=PV Zimakova and Mr. O. Dymenta
|publisher = Khimiya
|year = 1967
|pages = 128–140}}</ref>

: (CH<sub>2</sub>CH<sub>2</sub>)O + NaCl + H<sub>2</sub>O → HO–CH<sub>2</sub>CH<sub>2</sub>–Cl + NaOH

Other methods of ethylene oxide detection are<ref name="oe4" /> color reactions with [[pyridine]] derivatives and hydrolysis of ethylene glycol with [[periodic acid]]. The produced [[iodic acid]] is detected with [[silver nitrate]].

The main physical method of ethylene oxide detection is [[gas chromatography]].<ref name="iars" />

==Fire and explosion hazards==
Ethylene oxide is extremely flammable and its mixtures with air are explosive. When heated, it may rapidly expand causing fire and explosion.<ref>{{cite web
|url = http://www.safework.ru/ilo/ICSC/cards/view/?0155
|title = Ethylene oxide
|work = ICSC/International Chemical Safety Cards
|publisher = Institute of Industrial Safety, Labour Protection and Social Partnership
|accessdate = 2009-09-21}}</ref> The [[autoignition temperature]] is 429 °C, minimum inflammable content in the air is 2.7%,<ref>{{cite web
|year = 1988
|url = http://www.inchem.org/documents/hsg/hsg/hsg016.htm
|title = Ethylene Oxide
|work = Health and Safety Guide
|publisher = International Programme on Chemical Safety (IPCS) INCHEM
|accessdate = 2009-09-23}}</ref> and the NPFA rating is [[NFPA 704]].<ref>{{cite web
|date = January 10, 2009
|url = http://www.sonoma-county.org/des/pdf/fire/bulletins/info_bulletin_nfpa_marking2009_04n.pdf
|title = Informational Bulletin NFPA-04N 2009
|publisher = Department of Emergency Services, County of Sonoma
|accessdate = 2009-10-23}}</ref>

Fires caused by ethylene oxide are extinguished by traditional media, including foam, carbon dioxide or water. Extinguishing of burning ethylene oxide is complicated by that it can continue burning in an inert atmosphere and in water solutions. Fire suppression is reached only upon dilution with water above 22:1.<ref>{{cite web
|url = http://www-static.shell.com/static/chemicals/downloads/products_services/ethylene_oxide_safety_literature.pdf
|title = Ethylene Oxide Safety Literature
|publisher = Shell Chemicals
|accessdate = 2009-10-23}}</ref>

==Physiological effects==
===Effect on microorganisms===
Ethylene oxide inhibits growth of microorganisms ([[Disinfection|disinfectant properties]]) and when present in high concentrations, can completely destroy them. Strong alkylating properties make ethylene oxide a universal poison for [[protoplasm]]: it causes clotting of proteins, deactivation of [[enzyme]]s and other biologically important components of a living organism.<ref name="kons">{{cite web
|url = http://www.konservanti.com/veshestva32.html
|title = Ethylene oxide
|work = Preserving agents
|publisher = preservatives in food industry
|accessdate = 2009-09-25}}</ref>

Ethylene oxide acts more strongly against bacteria, especially [[gram-positive bacteria]], than against [[yeast]] and fungi.<ref name = "kons" /> The disinfectant effect of ethylene oxide is similar to that of sterilization by heat, but because of limited penetration, it affects only the surface. The Sterility Assurance Level, after a certain specified exposure to ethylene oxide is 10<sup>−6</sup>, meaning that the chance of finding a single bacterium is below 1 per million.<ref>{{cite web
|author = Conviser S.
|url = http://www.infectioncontroltoday.com/articles/061feat4.html
|title = The Future of Ethylene Oxide Sterilization
|publisher = ICT Magazine
|accessdate = 2009-10-23
}}</ref>

===Effects on humans and animals===
Ethylene oxide is an [[Alkylation|alkylating agent]]; it has irritating, sensitizing and narcotic effects.<ref name="ChemAnalitica11">{{cite web
|date = 1 April 2009
|url = http://chemanalytica.com/book/novyy_spravochnik_khimika_i_tekhnologa/11_radioaktivnye_veshchestva_vrednye_veshchestva_gigienicheskie_normativy/5177
|title = Harmful substances. Section 4. Heterocyclic compounds. Triplex heterocyclic compounds
|publisher = ChemAnalitica.com
|accessdate = 2009-09-21}}</ref> Chronic exposure to ethylene oxide also induces [[mutagen|mutagenic effects]]. The [[International Agency for Research on Cancer]] classifies ethylene oxide into group 1, meaning it is a proven [[carcinogen]].<ref name = "basesafework" >{{cite web
|author = Collins J. L.
|url = http://base.safework.ru/iloenc?hdoc&nd=857300040&nh=0
|title = Epoxy compounds
|work = Encyclopedia of the ILO
|publisher = Institute of Industrial Safety, Labour Protection and Social Partnership
|accessdate = 2009-09-25}}</ref><ref>[http://monographs.iarc.fr/ENG/Monographs/vol60/volume60.pdf IARC Vol 60]</ref> A 2003 study of 7,576 women exposed while at work in commercial sterilization facilities in the U.S. suggests ethylene oxide is associated with [[breast cancer]] incidence.<ref>{{cite journal |journal=Cancer Causes Control |year=2003 |volume=14 |issue=6 |pages=531–9 |title=Ethylene oxide and breast cancer incidence in a cohort study of 7576 women (United States) |author=Steenland K, Whelan E, Deddens J, Stayner L, Ward E |pmid=12948284 |doi=10.1023/A:1024891529592}}</ref> A 2004 follow up study analyzing 18,235 men and women workers exposed to ethylene oxide from 1987 to 1998 concluded "There was little evidence of any excess cancer mortality for the cohort as a whole, with the exception of [[bone cancer]] based on small numbers. Positive exposure-response trends for lymphoid tumors were found for males only. Reasons for the sex specificity of this effect are not known. There was also some evidence of a positive exposure-response for breast cancer mortality."<ref>{{cite journal |journal=Occup Environ Med |year=2004 |volume=61 |issue=1 |pages=2–7 |title=Mortality analyses in a cohort of 18 235 ethylene oxide exposed workers: follow up extended from 1987 to 1998 |author=Steenland K, Stayner L, Deddens J |pmid=14691266 |pmc=1757803}}</ref>

Ethylene oxide is toxic by inhalation with an U.S. [[Occupational Safety and Health Administration|OSHA]] permissible exposure limit of 1 ppm calculated as a time weighted average (TWA) over 8 hours of 1 ppm, and a short term exposure limit (excursion limit) calculated as a TWA over 15 minutes of 5 ppm. [29 CFR 19101.1048]. At concentrations in the air about 200 parts per million, ethylene oxide irritates [[mucous membrane]]s of the nose and throat; higher contents cause damage to the trachea and bronchi, progressing into the partial collapse of the lungs. High concentrations can cause [[pulmonary edema]] and damage the cardiovascular system; the damaging effect of ethylene oxide may occur only after 72 hours after exposure.<ref name="atsdr" /> The maximum content of ethylene oxide in the air according to the U.S. standards ([[American Conference of Governmental Industrial Hygienists|ACGIH]]) is 1.8&nbsp;mg/m<sup>3</sup>.<ref>{{cite book
|author = Carson P.A., Mumford C.J.
|title = Hazardous Chemicals Handbooks
|location = Oxford
|publisher = Butterworth-Heinemann Ltd
|year = 1994
|page = 85
|isbn = 0750602783
}}</ref> [[National Institute for Occupational Safety and Health|NIOSH]] has determined that the Immediately Dangerous to Life and Health level (IDLH) is 800 ppm.<ref>[http://www.cdc.gov/niosh/idlh/intridl4.html Documentation for Immediately Dangerous to Life or Health Concentrations (IDLH): NIOSH Chemical Listing and Documentation of Revised IDLH Values (as of 3/1/95)]</ref> Because the odor threshold for ethylene oxide varies between 250 and 700 ppm, it is imperceptible to human until well above dangerous levels. Therefore continuous monitors are standard practice. Currently, the substance is banned from the use for plant protection by the [[EU]] government.<ref name=bnpuk>{{cite web
| last = Chemicals Regulation Directorate
| title = Banned and Non-Authorised Pesticides in the United Kingdom
| url = http://www.pesticides.gov.uk/approvals.asp?id=55| accessdate = 1 December 2009}}</ref>

Ethylene oxide causes acute poisoning, accompanied by the following symptoms: slight heartbeat, muscle twitching, flushing, headache, diminished hearing, [[acidosis]], vomiting, dizziness, transient loss of consciousness and a sweet taste in the mouth. Acute intoxication is accompanied by a strong throbbing headache, dizziness, difficulty in speech and walking, sleep disturbance, pain in the legs, weakness, stiffness, sweating, increased muscular irritability, transient spasm of retinal vessels, enlargement of the liver and suppression of its antitoxic functions.<ref name = "ChemAnalitica11" />

Ethylene easily penetrates through the clothing and footwear, causing skin irritation and dermatitis with the formation of blisters, fever and [[leukocytosis]].<ref name="ChemAnalitica11" />

The [[median lethal dose]]s (LD<sub>50</sub>, or a dose required to kill half the members of a tested population after a certain time) for ethylene oxide are 72&nbsp;mg/kg (rat, oral) and 187&nbsp;mg/kg (rat, [[Subcutaneous tissue|subcutaneous]] injection).<ref name="msds">{{cite web
|url = http://msds.chem.ox.ac.uk/ET/ethylene_oxide.html
|title = Safety data for ethylene oxide
|publisher = The Physical and Theoretical Chemistry Laboratory Oxford University
|accessdate = 2009-10-22}}</ref>

==References==
{{reflist|2}}

==External links==
*[http://www.eosa.org EOSA Promoting the safe use of Ethylene Oxide for Sterilization]
*[http://webbook.nist.gov/cgi/cbook.cgi?ID=C75218 WebBook page for C2H4O]
*[http://www.npi.gov.au/database/substance-info/profiles/42.html National Pollutant Inventory – Ethylene oxide fact sheet]
*[http://www.americanchemistry.com/s_acc/bin.asp?SID=1&DID=4468&CID=172&VID=109&DOC=File.PDF/html/introduction.html Ethylene Oxide User's Guide]
*[http://www.anpro.com/support/MSDS.pdf Ethylene Oxide MSDS (Material Safety Data Sheet).]
*[http://www.cdc.gov/niosh/topics/ethyleneoxide/ National Institute for Occupational Safety and Health – Ethylene Oxide Topic Page]
*[http://www.anpro.com/articles/EOSA%20update%20article.htm EOSA memo about Ethylene Oxide (EtO) facts]

[[Category:Monomers]]
[[Category:Hazardous air pollutants]]
[[Category:Occupational safety and health]]
[[Category:IARC Group 1 carcinogens]]
[[Category:Oxiranes]]
[[Category:Epoxides]]

{{Link FA|ru}}

[[ar:أكسيد الإيثيلين]]
[[cs:Ethylenoxid]]
[[de:Ethylenoxid]]
[[el:Εποξυαιθάνιο]]
[[es:Óxido de etileno]]
[[fa:اتیلن اکساید]]
[[fr:Oxyde d'éthylène]]
[[ko:산화 에틸렌]]
[[it:Ossido di etilene]]
[[lv:Etilēnoksīds]]
[[hu:Etilén-oxid]]
[[nl:Etheenoxide]]
[[ja:エチレンオキシド]]
[[no:Etylenoksid]]
[[pl:Tlenek etylenu]]
[[pt:Óxido de etileno]]
[[ru:Окись этилена]]
[[sk:Etylénoxid]]
[[fi:Etyleenioksidi]]
[[sv:Etenoxid]]
[[zh:环氧乙烷]]
[[Category:2Fix]]