Ethylene oxide: Difference between revisions

{{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}}

| Watchedfields = changed

| verifiedrevid = 446701253

| ImageFileL1 = Ethylene oxide.svg

| ImageSizeL1 = 100 px

| 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 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</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⁻¹<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⁻³<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 = −30.5·10⁻⁶{{nbsp}}cm³/mol<ref>[[#Haynes|Haynes]], p. 3.576</ref>

}}

| Section3 = {{Chembox Thermochemistry

|DeltaHf = −52.6{{nbsp}}kJ·mol⁻¹<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⁻¹·K⁻¹<ref name=r522/>

|HeatCapacity = 47.9{{nbsp}}J·mol⁻¹·K⁻¹<ref name=r522/>

}}

| Section4 = {{Chembox Hazards

|ExternalSDS = [http://www.inchem.org/documents/icsc/icsc/eics0155.htm ICSC 0155]

|GHSPictograms = {{GHS02}}{{GHS04}}{{GHS06}}{{GHS08}}

|MainHazards = [[Carcinogen]]<br />Extremely flammable

|NFPA-H = 3

|NFPA-F = 4

|NFPA-R = 3

|HPhrases = {{H-phrases|220|230|280|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/m³) C 5{{nbsp}}ppm (9{{nbsp}}mg/m³) [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|url=https://books.google.com/books?id=oJy5wdzi0yUC&pg=PA309|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}}</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>

Ethylene oxide was first reported in 1859 by the [[France|French]] chemist [[Charles-Adolphe Wurtz]],<ref>{{cite journal|author=Wurtz, A.|journal= Comptes rendus|volume= 48|pages= 101–105 |year=1859| title= Sur l'oxyde d'éthylène| url= http://gallica.bnf.fr/ark:/12148/bpt6k30054/f101.image}}</ref> who prepared it by treating [[2-chloroethanol]] with [[potassium hydroxide]]:

:<chem>Cl-CH2CH2-OH + KOH -> (CH2CH2)O + KCl + H2O</chem>

Wurtz measured the [[boiling point]] of ethylene oxide as {{Convert|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

|editor1=Zimakov, P.V. |editor2=Dyment, O. H. | publisher = Khimiya

| year = 1967

| pages = 15–17}}</ref> Wurtz mistakenly assumed that ethylene oxide has the properties of an organic base. This misconception persisted until 1896, when [[Georg Bredig]] found that ethylene oxide is not an [[electrolyte]].<ref name="oe1" /><ref>{{cite journal|author=Bredig, G.|author2= Usoff, A. |year=1896|url=https://books.google.com/books?id=0cPmAAAAMAAJ&pg=PA116 |title=Ist Acetylen ein Elektrolyt?|trans-title=Is acetylene an electrolyte?|journal=Zeitschrift für Elektrochemie|volume=3|pages=116–117}}</ref> That it differed from other [[ether]]s — particularly by its propensity to engage in the addition reactions typical of [[Saturated and unsaturated compounds|unsaturated compounds]] — had long been a matter of debate. The heterocyclic triangular structure of ethylene oxide was proposed by 1868 or earlier.<ref>[[Eugen Freiherr von Gorup-Besanez|Eugen F. von Gorup-Besanez]], ed., ''Lehrbuch der organischen Chemie für den Unterricht auf Universitäten'' … [Textbook of Organic Chemistry for Instruction at Universities … ], 3rd ed. (Braunschweig, Germany: Friedrich Vieweg und Sohn, 1868), vol. 2, [https://archive.org/details/bub_gb_UJyCAAAAIAAJ/page/n314 p. 286].<br /> See also [https://books.google.com/books?id=oc5Qth0MKE8C&pg=PA253 p. 253] of the 1876 edition: Eugen F. von Gorup-Besanez, ed., ''Lehrbuch der organischen Chemie für den Unterricht auf Universitäten'' …, 5th ed. (Braunschweig, Germany: Friedrich Vieweg und Sohn, 1876), vol. 2.</ref>

Wurtz's 1859 synthesis long remained the only method of preparing ethylene oxide, despite numerous attempts, including by Wurtz himself, to produce ethylene oxide directly from [[ethylene]].<ref name="ect">{{cite book| chapter = Ethylene Oxide| title = Kirk-Othmer Encyclopedia of Chemical Technology. Elastomers, synthetic to Expert Systems| edition = 4| location = New York| publisher = John Wiley & Sons| year = 1994| isbn=978-0-471-48514-8| volume = 9| pages = 450–466}}</ref> Only in 1931 did French chemist Theodore Lefort develop a method of direct oxidation of ethylene in the presence of [[silver]] [[catalyst]].<ref>Lefort, T.E. (23 April 1935) "Process for the production of ethylene oxide". {{US Patent|1998878}}</ref> Since 1940, almost all industrial production of ethylene oxide has relied on this process.<ref>{{cite journal|title= Manufacture and Uses of Ethylene Oxide and Ethylene Glycol| author= McClellan, P. P. | journal= Ind. Eng. Chem.|year= 1950| volume= 42|pages= 2402–2407| doi= 10.1021/ie50492a013|issue= 12}}</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]].{{fact|date=October 2023}}

[[File:Ethylene oxide refrigerated liquid.jpg|thumb|right|Condensed ethylene oxide]]

The epoxy cycle of ethylene oxide is an almost regular triangle with bond angles of about 60° and a significant angular [[Strain (chemistry)|strain]] corresponding to the energy of 105 kJ/mol.<ref>{{cite encyclopedia| chapter= Voltage molecules| title = Chemical Encyclopedia| editor = Knunyants, I. L.| encyclopedia = 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 = V. F. Traven| publisher = ECC "Academkniga"| year = 2004| volume = 2| pages = 102–106| isbn = 5-94628-172-0}}</ref> For comparison, in [[Alcohol (chemistry)|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 each of the principal axes are ''I_A'' = {{val|32.921|e=-40|u=g·cm{{sup|2}}}}, ''I_B'' = {{val|37.926|e=-40|u=g·cm{{sup|2}}}} and ''I_C'' = {{val|59.510|e=-40|u=g·cm{{sup|2}}}}.<ref>{{cite journal| author = Cunningham G. L.|author2= Levan W. I.|author3= 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| issue = 10| bibcode= 1948PhRv...74.1537C}}</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>

| '''{{chem2|(C2H4)O -> C2H4 + O}}''' (cleavage of two bonds)

| 354.38

| Calculated, from atomic enthalpies

|'''{{chem2|[[Ethanol|C2H5OH]] -> C2H5 + OH}}''' (breaking one bond)

| 405.85

| Electron impact

|'''{{chem2|[[Dimethyl ether|CH3OCH3]] -> CH3O + CH3}}''' (breaking one bond)

| 334.72

| Calculated using enthalpies of radicals formation

This instability correlates with its high reactivity, explaining the ease of its [[Cyclic compound|ring-opening]] reactions (see [[#Chemical properties|Chemical properties]]).

Ethylene oxide is a colorless gas at {{Convert|25|C|}} and is a mobile liquid at {{Convert|0|C|}} – viscosity of liquid ethylene oxide at 0&nbsp;°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{{nbsp}}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

| access-date = 29 September 2009

| archive-url = https://web.archive.org/web/20110606033044/http://www.atsdr.cdc.gov/MHMI/mmg137.html

| archive-date = 6 June 2011

| url-status = dead

}}</ref> Ethylene oxide is readily soluble in water, [[ethanol]], [[diethyl ether]] and many organic solvents.<ref>{{cite web

| url = http://dic.academic.ru/dic.nsf/bse/154711/Этилена

| title = Этилена окись (Ethylene oxide)

| publisher = [[Great Soviet Encyclopedia]]

| access-date = 25 September 2009

| language =ru

Main thermodynamical constants are:<ref name="sch1">{{cite web | date = 1 April 2009| url= http://chemanalytica.com/book/novyy_spravochnik_khimika_i_tekhnologa/12_obshchie_svedeniya/6084 | title = Термодинамические показатели органических соединений | publisher = ChemAnalitica.com | access-date = 21 September 2009}}</ref>

* The [[surface tension]] of liquid ethylene oxide, at the interface with its own vapor, is {{Convert|35.8|mJ/m2||abbr=on}} at {{Convert|-50.1|C|}} and {{Convert|27.6|mJ/m2||abbr=on}} at {{Convert|-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| access-date = 21 September 2009}}</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| access-date = 21 September 2009}}</ref> {{Convert|57.7|C|}} ({{Convert|2|atm|kPa psi|abbr=on}}), {{Convert|83.6|C|}} ({{Convert|5|atm|kPa psi|abbr=on}}), and {{Convert|114.0|C|}} ({{Convert|10|atm|kPa psi|abbr=on}}).

* [[Viscosity]] decreases with temperature with the values of 0.577{{nbsp}}kPa·s at {{Convert|-49.8|C|}}, 0.488 kPa·s at {{Convert|-38.2|C|}}, 0.394{{nbsp}}kPa·s at {{Convert|-21.0|C|}}, and 0.320{{nbsp}}kPa·s at {{Convert|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| access-date = 21 September 2009}}</ref>

Between {{Convert|−91|and|10.5|C}}, vapor pressure ''p'' (in mmHg) varies with temperature (''T'' in °C) as

:<math>\lg p = 6.251 - \frac{1115.1}{244.14 + T}</math>.<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| access-date = 21 September 2009}}</ref>

|+ Properties of liquid ethylene oxide<ref name="ect" />

|-

! Temperature, °C

! Vapor pressure, kPa

! Enthalpy of the liquid, J/g

! Enthalpy of vaporization, J/g

! [[Heat capacity]], J/(kg·K)

! [[Thermal conductivity]], W/(m·K)

| −40

| −20

| 0

| 20

| 40

| 60

| 80

| 100

| 120

| 140

| 160

| 180

| 195.8

|}

|+ 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

! Thermal conductivity, W/(m·K)

! Heat capacity, J/(mol·K)

| −52.63

| −13.10

| −52.72

| −12.84

| −56.53

| −59.62

| −62.13

| −64.10

| −65.61

Ethylene oxide readily reacts with diverse compounds with opening of the ring. Its typical reactions are with nucleophiles which proceed via the '''[[Nucleophilic substitution|S_N2]]''' mechanism both in acidic (weak nucleophiles: water, alcohols) and alkaline media (strong nucleophiles: OH⁻, RO⁻, NH₃, RNH₂, RR'NH, etc.).<ref name="traven" /> The general reaction scheme is

: [[File:Ethylene oxide reactions.png|400px|Ethylene oxide reactions]]

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|editor1=Zimakov, P.V. |editor2=Dyment, O. H.| publisher = Khimiya| year = 1967| pages = 90–120}}</ref>

The reaction is usually carried out at about {{Convert|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 [[diethylene glycol|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| access-date = 5 October 2009}}</ref>

Reactions with [[Alcohol (chemistry)|alcohol]]s proceed similarly yielding ethylene glycol ethers:

Reactions with lower alcohols occur less actively than with water and require more severe conditions, such as heating to {{Convert|160|C|}} and pressurizing to {{Convert|3|MPa||abbr=on}} and adding an acid or alkali catalyst.

Reactions of ethylene oxide with [[carboxylic acid]]s in the presence of a catalyst results in glycol mono- and diesters:

: (CH₂CH₂)O + CH₃CO₂H → HOCH₂CH₂–O₂CCH₃

: (CH₂CH₂)O + (CH₃CO)₂O → CH₃CO₂CH₂CH₂O₂CCH₃

: (CH₂CH₂)O + CH₃CONH₂ → HOCH₂CH₂NHC(O)CH₃

Addition of ethylene oxide to higher carboxylic acids is carried out at elevated temperatures (typically {{Convert|140-180|C|}}) and pressure ({{Convert|0.3-0.5|MPa||abbr=on}}) 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|editor1=van Os |editor2=N. M.| publisher = CRC Press| year = 1998| pages = 129–131|url=https://books.google.com/books?id=YoZ6CjYNLoQC&pg=PA129| isbn = 978-0-8247-9997-7}}</ref> The carboxylate ion acts as [[nucleophile]] in the reaction:

: (CH₂CH₂)O + RCO₂⁻ → RCO₂CH₂CH₂O⁻

:RCO₂CH₂CH₂O⁻ + RCO₂H → RCO₂CH₂CH₂OH + RCO₂⁻

Ethylene oxide reacts with [[ammonia]] forming a mixture of mono-, di- and tri- [[ethanolamine]]s. The reaction is stimulated by adding a small amount of water.

[[Trimethylamine]] reacts with ethylene oxide in the presence of water, forming [[choline]]:<ref>{{cite book

|author1=Petrov, AA |author2=Balian HV |author3=Troshchenko AT | chapter= Chapter 12. Amino alcohol| title = Organic chemistry| editor= Stadnichuk| edition = 5|location = St. Petersburg| year = 2002| page = 286| isbn = 5-8194-0067-4}}</ref>

: (CH₂CH₂)O + (CH₃)₃N + H₂O → [HOCH₂CH₂N (CH₃)₃]⁺OH⁻

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|author1=Sheppard, William A. |author2=Sharts, Clay M.| title = Organic Fluorine Chemistry|url=https://archive.org/details/organicfluorinec0000shep |url-access=registration |publisher = W. A. Benjamin| year = 1969| page= 98| isbn = 0-8053-8790-0}}</ref>

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:

: <chem>(CH2CH2)O{} + RMgBr -> R-CH2CH2-OMgBr ->[\ce{H2O}]

\overset{primary~alcohol}{R-CH2CH2-OH}</chem>

: <chem>(CH2CH2)O{} + \overset{alkyl~lithium}{RLi} -> R-CH2CH2-OLi ->[\ce{H2O}] R-CH2CH2-OH</chem>

Ethylene oxide easily reacts with [[hydrogen cyanide]] forming [[ethylene cyanohydrin]]:

A slightly chilled (10–20&nbsp;°C) aqueous solution of [[calcium cyanide]] can be used instead of HCN:<ref>{{OrgSynth| author=Kendall, E. C. and McKenzie, B.| year=1923| title=o-Chloromercuriphenol| volume=3| pages=57| prep=cv1p0256}}</ref>

When reacting with the [[hydrogen sulfide]], ethylene oxide forms [[2-Mercaptoethanol|2-mercaptoethanol]] and [[thiodiglycol]], and with alkylmercaptans it produces 2-alkyl mercaptoetanol:

:3 (CH₂CH₂)O + H₂S → [(HO–CH₂CH₂)₃S⁺]OH⁻

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-nitroethanol]]:<ref>{{OrgSynth| author=Noland, Wayland E.| prep=CV5P0833| title = 2-Nitroethanol|volume=5|pages=833|year=1973}}</ref>

With [[nitric acid]], ethylene oxide forms mono- and [[Ethylene glycol dinitrate|dinitroglycols]]:<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>

: <chem>(CH2CH2)O{} + \overset{nitric\atop acid}{HNO3} -> HO-CH2CH2-ONO2 ->[\ce{+HNO3}] [\ce{-H2O}] O2NO-CH2CH2-ONO_2</chem>

In the presence of [[Alkoxide|alkoxides]], reactions of ethylene oxide with compounds containing active methylene group leads to the formation of [[gamma-Butyrolactone|butyrolactones]]:<ref>{{cite book| author = Vogel, A. I.|title = Vogel's Textbook of practical organic chemistry| url = https://archive.org/details/Vogels_Textbook_of_Practical_Organic_Chemistry_5ed_1989_Longman_WW| edition = 5|location = UK| publisher = Longman Scientific & Technical| year = 1989| page = 1088| isbn = 0-582-46236-3}}</ref>

====Alkylation of aromatic compounds====

Ethylene oxide enters into the [[Friedel–Crafts reaction]] with benzene to form [[phenethyl alcohol]]:

[[Styrene]] can be obtained in one stage if this reaction is conducted at elevated temperatures ({{Convert|315–440|C|}}) and pressures ({{Convert|0.35–0.7|MPa||abbr=on}}), in presence of an aluminosilicate catalyst.<ref>Watson, James M. and Forward, Cleve (17 April 1984) "Reaction of benzene with ethylene oxide to produce styrene" {{US Patent|4443643}}</ref>

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. TheirCharacteristics and Applications| publisher = Kodansha| year = 1982| pages= 33–34| isbn =4-06-139444-4}}</ref>

:''n'' (CH₂CH₂)O → (–CH₂CH₂–O–)_''n''

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="autogenerated1">{{cite journal| author = H. W. Roesky|author2= H. G. Schmidt| title = Reaction of Ethylene Oxide with Sulfur Dioxide in the Presence of Cesium Ions: Synthesis of 1,3,6,9,2 λ ⁴-Tetraoxathia-2-cycloundecanone| journal = Angewandte Chemie International Edition| year = 1985|doi=10.1002/anie.198506951| volume = 24| page = 695| issue = 8}}</ref>

: [[File:Tetraoxathia-2-cycloundecanone.png|350px]]

When heated to about {{Convert|400|C||sigfig=2}}, or to {{Convert|150–300|C||sigfig=2}} in the presence of a catalyst ([[aluminium oxide|Al₂O₃]], [[phosphoric acid|H₃PO₄]], etc.), ethylene oxide [[isomerization|isomerizes]] into [[acetaldehyde]]:<ref name="petrov">{{cite book

|author1=Petrov, AA |author2=Balian HV |author3=Troshchenko AT | chapter= Chapter 4. Ethers

| title = Organic chemistry| edition=5

| location = St. Petersburg.

| year = 2002

| pages = 159–160

| isbn = 5-8194-0067-4}}</ref>

: <chem>(CH2CH2)O ->[\ce{200^\circ C}] [\ce{Al2O3}] \overset{acetaldehyde}{CH3CHO}</chem>

The radical mechanism was proposed 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

| issue = 1

| bibcode = 1964JChPh..40..105B

{{NumBlk|:| (CH₂CH₂)O ↔ •CH₂CH₂O• → CH₃CHO*|{{EquationRef|1}}}}

{{NumBlk|:| CH₃CHO* → CH₃• + CHO•|{{EquationRef|2}}}}

{{NumBlk|:| CH₃CHO* + M → CH₃CHO + M*|{{EquationRef|3}}}}

In reaction ({{EquationNote|3}}), '''M''' refers to the wall of the reaction vessel or to a heterogeneous catalyst.

The moiety CH₃CHO* represents a short-lived (lifetime of 10^−8.5 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 [[#Thermal decomposition|Thermal decomposition]]).<ref name="oe2"/>

| author = Hudlický M.

| title = Reductions in Organic Chemistry

| location = Chichester

| publisher = Ellis Horwood Limited

| year = 1984

| page = 83

| isbn = 0-85312-345-4}}</ref>

: <chem>(CH2CH2)O{} + H2 ->[{}\atop\ce{Ni, Pt, Pd, BH3, LiAlH4}\text{ or other hydrides}] [\ce{80^\circ C}] \underset{ethanol}{C2H5OH}</chem>

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 LiAlH₄ and TiCl₃) and of [[iron(III) chloride]] with [[butyllithium]] in [[tetrahydrofuran]].<ref name="reduction" />

: <chem>(CH2CH2)O{} + H2 ->[{}\atop\ce{{Zn} + CH3COOH}] \underset{ethylene}{CH2=CH2} + H2O</chem>

: <chem>(CH2CH2)O{} + O2 ->[\ce{AgNO3}] \overset{glycolic\ acid}{HOCH2CO2H}</chem>

Deep gas-phase reactor oxidation of ethylene oxide at {{Convert|800-1000|K|}} and a pressure of {{Convert|0.1–1|MPa||abbr=on}} yields a complex mixture of products containing O₂, H₂, [[carbon monoxide|CO]], [[carbon dioxide|CO₂]], [[methane|CH₄]], [[acetylene|C₂H₂]], [[ethylene|C₂H₄]], [[ethane|C₂H₆]], [[propylene|C₃H₆]], [[propane|C₃H₈]] and [[acetaldehyde|CH₃CHO]].<ref>{{cite journal

| author = Dagaut P.|author2= Voisin D.|author3= Cathonnet M.|author4= Mcguinness M.|author5= 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

|issue= 1–2| pages = 62–68

| doi = 10.1016/0010-2180(95)00229-4

In the presence of acid catalysts, ethylene oxide dimerizes to afford [[dioxane]]:

The dimerization reaction is unselective. By-products include [[acetaldehyde]] (due to [[#Isomerization|isomerization]]). The selectivity and speed of dimerization can be increased by adding a catalyst, such as platinum, platinum-palladium, or [[iodine]] with [[sulfolane]]. 2-methyl-1,3-[[dioxolane]] is formed as a side product in the last case.<ref>Stapp, Paul R. (21 December 1976) "Cyclodimerization of ethylene oxide" {{US Patent|3998848}}</ref>

Liquid ethylene oxide can form [[polyethylene glycol]]s. The polymerization can proceed via radical and ionic mechanisms, but only the latter has a wide practical application.<ref name="glycol">{{cite book

|author1=Dyment, ON |author2=Kazanskii, KS |author3=Miroshnikov AM | title = Гликоли и другие производные окисей этилена и пропилена|trans-title=Glycols and other derivatives of ethylene oxide and propylene

| editor = Dyment, ON

| publisher = Khimiya

| year = 1976

| pages = 214–217}}</ref> [[Cationic polymerization]] of ethylene oxide is assisted by [[protic]] acids ([[perchloric acid|HClO₄]], [[hydrochloric acid|HCl]]), Lewis acids ([[Tin(IV) chloride|SnCl₄]], [[boron trifluoride|BF₃]], etc.), [[organometallic compound]]s, or more complex reagents:<ref name="glycol" />

: <math chem>n\ce{(CH2CH2)O ->[\ce{SnCl4}]}\ \overbrace{\ce{(CH2CH2-O-)}_n}^\ce{polyethyleneglycol}</math>

| title = Polymeric materials encyclopedia

| editor= Salamone, Joseph C.

| publisher = CRC Press

| year = 1996

| volume = 8

| pages = 6036–6037

| isbn = 978-0-8493-2470-3}}</ref> At the first stage, the catalyst (MX_m) is initiated by alkyl-or acylhalogen or by compounds with active hydrogen atoms, usually water, alcohol or glycol:

:MX_m + ROH → MX_mRO⁻H⁺

: (CH₂CH₂)O + MX_mRO⁻H⁺ → (CH₂CH₂)O•••H⁺O⁻RMX_m

: (CH₂CH₂)O•••H⁺ O⁻RMX_m → HO–CH₂CH₂⁺ + MX_mRO⁻₂

:HO–CH₂CH₂–(O–CH₂CH₂)_n⁺ + MX_mRO⁻ → HO–CH₂CH₂–(O–CH₂CH₂)_n–OR + MX_m

:H(O–CH₂CH₂)_n–O–CH₂–CH₂⁺ + MX_mRO⁻ → H(O–CH₂CH₂)_n–O–CH=CH₂ + MX_m + ROH

[[Anionic polymerization]] of ethylene oxide is assisted by bases, such as [[alkoxide]]s, [[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" />

: (CH₂CH₂)O + RONa → RO–CH₂CH₂–O⁻Na⁺

:RO–CH₂CH₂–O⁻Na⁺ + n (CH₂CH₂)O → RO–(CH₂CH₂–O)_n–CH₂CH₂–O⁻Na⁺

:RO–(CH₂CH₂–O)_n–CH₂CH₂–O⁻Na⁺ → RO–(CH₂CH₂–O)_n–CH=CH₂ + NaOH

:RO–(CH₂CH₂–O)_n–CH₂CH₂–O⁻Na⁺ + H₂O → RO–(CH₂CH₂–O)_(n+1)OH + NaOH

Ethylene oxide is relatively stable to heating – in the absence of a catalyst, it does not dissociate up to {{Convert|300|C|}}, and only above {{Convert|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

|editor1=Zimakov, P.V. |editor2=Dyment, O. H. | publisher = Khimiya

| year = 1967

| pages = 57–85}}</ref> The first stage involves [[#Isomerization|isomerization]], however high temperature accelerates 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.|author2= Blades A.T.

| title = The Kinetics of the Thermal Reactions of Ethylene Oxide

| journal = Canadian Journal of Chemistry

| year = 1963|doi=10.1139/v63-434

| volume = 41

| pages = 2956–2961

| issue = 12| doi-access =

}}</ref> High-temperature [[pyrolysis]] ({{Convert|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.|author2= 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

| pages = 1782–1787|issue = 10

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 group|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]] (ethylene sulfide):<ref>{{cite book

| author = Gilchrist T.

| title = Heterocyclic Chemistry

| publisher = Pearson Education

| year = 1985

| pages = 411–412

| isbn = 81-317-0793-8}}</ref>

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

|author1=Smith, Michael B. |author2=March, Jerry

| title = Advanced organic chemistry. Reactions, Mechanisms and Structure

| publisher = Wiley-Interscience

| year = 2007|url=https://books.google.com/books?id=JDR-nZpojeEC

| isbn =978-0-471-72091-1}}</ref>

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

Heating ethylene oxide to 100&nbsp;°C with [[carbon dioxide]], in a non-polar solvent in the presence of ''bis''-(triphenylphosphine)-nickel(0) results in [[ethylene carbonate]]:<ref>{{cite book |author1 = Fieser, L.

|author2 = Fieser, M.

|title = Reagents for Organic Synthesis

|publisher = Wiley

|volume = 7

|year = 1979

|page = [https://archive.org/details/reagentsfororgan07fies_0/page/545 545]

|isbn = 978-0-471-02918-2

|url-access = registration

|url = https://archive.org/details/reagentsfororgan07fies_0/page/545

}}</ref>

| author = Sheldon RA

| title= Chemicals from synthesis gas: catalytic reactions of CO and, Volume 2

| url=https://books.google.com/books?id=s1_rjRUlu1EC&pg=PA193|page=193

| publisher = Springer

| year = 1983

| isbn=90-277-1489-4}}</ref>

Reaction of ethylene oxide with [[formaldehyde]] at 80–150&nbsp;°C in the presence of a catalyst leads to the formation of [[dioxolane|1,3-dioxolane]]:<ref name="fiser">{{cite book

|author1=Fieser, L. |author2=Fieser, M.

| title = Reagents for Organic Synthesis

| publisher = Wiley

| year = 1977|isbn=978-0-471-25873-5

| volume = 6

| page= 197}}</ref>

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

Catalytic [[hydroformylation]] of ethylene oxide gives hydroxypropanal which can be hydrogenated to [[propane-1,3-diol]]:<ref>Han, Yuan-Zhang and Viswanathan, Krishnan (13 February 2003) "Hydroformylation of ethylene oxide" {{US Patent|20030032845}}</ref>

: <chem>(CH2CH2)O + CO + H2 -> CHO-CH2CH2-OH ->[\ce{+H2}] HO-CH2CH2CH2-OH</chem>

Dehydrochlorination of [[2-chloroethanol]], developed by Wurtz in 1859, remains a common laboratory route to ethylene oxide:

:<chem>Cl-CH2CH2-OH + NaOH -> (CH2CH2)O + NaCl + H2O</chem>

| chapter= Chapter V. Producing ethylene oxide through ethylene

| title = Ethylene oxide

|editor1=Zimakov, P.V. |editor2=Dyment, O. H. | publisher = Khimiya

| year = 1967

| pages = 155–182}}</ref>

With a high yield (90%) ethylene oxide can be produced by treating [[calcium oxide]] with ethyl hypochlorite; substituting calcium by other alkaline earth metals reduces the reaction yield:<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

|editor1=Zimakov, P.V. |editor2=Dyment, O. H. | publisher = Khimiya

| year = 1967

| pages = 145–153}}</ref>

:<chem>2 CH3CH2-OCl + CaO -> 2 (CH2CH2)O + CaCl2 + H2O</chem>

| author = McMurry J.

| title = Organic chemistry

| edition = 7

| publisher = Thomson

| year = 2008

| page= 661

| isbn = 978-0-495-11258-7}}</ref>

:<chem>I-CH2CH2-I + Ag2O -> (CH2CH2)O + 2AgI</chem>

and decomposition of [[ethylene carbonate]] at {{Convert|200–210|C|}} in the presence of [[hexachloroethane]]:

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

| author = Norris, J.F.

| title = The Manufacture of War Gases in Germany

| journal = Journal of Industrial and Engineering Chemistry

| year = 1919

| volume = 11

| pages = 817–829

| doi = 10.1021/ie50117a002

| issue = 9| url = https://zenodo.org/record/1428740

}}</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 {{Convert|200–300|C||sigfig=2}} and pressure ({{Convert|1–3|MPa||abbr=on}}).<ref name = "industrial"/> This more efficient route accounted for about half of ethylene oxide production in the 1950s in the US, and after 1975 it completely replaced the previous methods.<ref name = "industrial" >{{cite book

|author1=Weissermel K. |author2=Arpe H-J. | title = Industrial organic chemistry

| location = Weinheim

| publisher = Wiley-VCH

| year = 2003

| pages = 145–148

| isbn = 978-3-527-30578-0}}</ref>

The production of ethylene oxide accounts for approximately 11% of worldwide ethylene demand.<ref>[http://www.ceresana.com/en/market-studies/chemicals/ethylene/ Market Study: Ethylene] {{Webarchive|url=https://web.archive.org/web/20150307115926/http://www.ceresana.com/en/market-studies/chemicals/ethylene/ |date=7 March 2015 }}. Ceresana.com (December 2010). Retrieved on 8 May 2017.</ref>

| 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

| access-date = 19 November 2009}}</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 I.I.

| title = The technology of basic organic synthesis

| publisher = Khimiya

| year = 1968

| pages = 554–559}}</ref>

:CH₂=CH₂ + HOCl → HO–CH₂CH₂–Cl

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

:2 HO–CH₂CH₂–Cl + Ca(OH)₂ → 2 (CH₂CH₂)O + CaCl₂ + 2H₂O

The produced ethylene oxide is purified by [[rectified spirit|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 {{Convert|1|t|}} of ethylene oxide, about {{Convert|200|kg||abbr=on}} of ethylene dichloride is produced.<ref name="uk" /> But, the major drawbacks of this process are high chlorine consumption and effluent load. This process is now obsolete.

| chapter = Catalitic Oxidation of Olefins

| title = Advances in catalysis and related subjects

|editor1=Eley, D.D. |editor2=Pines, H. |editor3=Weisz, P.B. | 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.<ref name="cmpa">{{cite book

|author1=Bloch H. P. |author2=Godse A. | title = Compressors and modern process applications|publisher = John Wiley and Sons

| year = 2006

| pages = 295–296

| isbn = 978-0-471-72792-7

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 |access-date=3 October 2009 |url-status=dead |archive-url=https://web.archive.org/web/20110716014802/http://www.scidesign.com/Business/EO%20-%20EG%20Process/EO_EG_Process.htm |archive-date=16 July 2011 }}</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.

|author1=Chauvel A. |author2=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 = 2-7108-0563-4}}</ref>