Editing Ethylene oxide (section)

==History==
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]]:

: {{chem2 | Cl\sCH2CH2\sOH + KOH -> (CH2CH2)O + KCl + H2O }}

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 |title=Ist Acetylen ein Elektrolyt? |trans-title=Is acetylene an electrolyte? |journal=Zeitschrift für Elektrochemie |volume=3 |issue=6 |pages=116–117 |doi=10.1002/bbpc.189600028 |url=https://books.google.com/books?id=0cPmAAAAMAAJ&pg=PA116|url-access=subscription }}</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 |issue=12 |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]] [[mustard gas]].{{Citation needed|date=October 2023}}