Talk:Ethylene oxide

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Untitled[edit]

I don't see any oxygen in the structure diagram. Am I missing something? The image is

Image:Ethylene oxide.png

which is identical to

Image:Ethene.png

Hmmm... I clicked on Reload and it appeared...

Duplicate page[edit]

I notice that there is another (and IMHO much inferior) page on this compound at epoxyethane. I would like to turn that page into a simple redirect to this page. Any comments? Walkerma 06:10, 19 Mar 2005 (UTC)

IUPAC name[edit]

The article states that the IUPAC name of ethylene oxide is "1,2-epoxyethane". I don't think the numbers are needed in this case, since there is no ambiguity in the name "epoxyethane", and according to the naming guidelines, position numbers should not be used when not necessary. 193.217.163.93 14:26, 3 October 2006 (UTC)

New External Link[edit]

I added a new external link to http://www.eosa.org on the article page. This site deals with the safe use of Ethylene Oxide.

--Scot1967 (talk) 16:08, 5 January 2009 (UTC)

Old chembox[edit]

I'm moving the old chemical infobox here, as I've replaced it with a chembox new.

Ben 18:14, 9 September 2007 (UTC)

Properties

General

Ethylene oxide structure
Ethylene oxide

Name Epoxyethane
Chemical formula C2H4O
Formula weight 44.05 u
Synonyms Ethylene oxide, dimethylene oxide, oxirane, oxacyclopropane
SMILES C1CO1
CAS number 75-21-8
UN number 1040

Phase behavior

Melting point 161 K (-112.1 °C)
Boiling point 283.5 K (10.4 °C)
Thermal decomposition ? K (? °C)
Triple point 160.6 K (-112.4 °C)
0.0078 kPa
Critical point 468.9 K (195.9 °C)
72.3 kPa
ΔfusH 5.17 kJ/mol
ΔfusS 32.2 J/(mol·K)
ΔvapH 25.5 kJ/mol
Solubility Miscible with water.

Liquid properties

ΔfH0liquid -96 kJ/mol
S0liquid 149.45 J/{mol·K)
Cp 86.9 J/(mol·K)
Density 0.899 ×103 kg/m3

Gas properties

ΔfH0gas -52.6 kJ/mol
S0gas 243 J/(mol·K)
Cp 47 J/(mol·K)

Safety

Acute effects Lung irritation, convulsions.
Chronic effects CNS damage
Potential carcinogen
Flash point -55 °C
Autoignition temperature 429 °C
Explosive limits 3 to 100%

More info

Properties NIST WebBook
MSDS Hazardous Chemical Database

SI units were used where possible. Unless otherwise stated, standard conditions were used.

Disclaimer and references

Epoxyethane[edit]

Is there a reason I have missed why this page makes no mention of the name epoxyethane whatsoever? I was under the impression that is a fairly common name for this compound. I-hunter (talk) 20:42, 21 February 2009 (UTC)

It's listed as the IUPAC name. If you click Show you'll see it. If we can confirm that epoxyethane is indeed the correct IUPAC name, then we should perhaps mention it in the lead. Thanks, Walkerma (talk) 21:12, 21 February 2009 (UTC)

Use in medical sterilization[edit]

Ethylene oxide is commonly used in medical sterilization, it would be nice if a little info on its use and process for this type sterilization was included. —Preceding unsigned comment added by 130.216.208.11 (talk) 23:49, 1 July 2010 (UTC)

There is some "little info" on that in the lead and "applications", "other uses". Materialscientist (talk) 23:52, 1 July 2010 (UTC)

History of Synthesis[edit]

"The first synthesis method had long remained the only, despite numerous attempts of scientists, including Wurtz himself, to produce ethylene oxide directly from ethyl". Should "ethyl" not read "ethanol" or "ethylene/ethene"? Moletrouser (talk) 05:27, 9 August 2010 (UTC)

"China Petrochemical Corporation (~1000 tonnes in 2006[68])"[edit]

Taken from this version of the article. There's something very likely wrong with this. The number is three orders of magnitude below the other productions mentioned nearby. The source cited requires registration. 80.250.81.35 (talk) 08:34, 11 December 2012 (UTC)

1 million, not 1000, probably my typo, fixed, thanks. Materialscientist (talk) 08:46, 11 December 2012 (UTC)

Structure of ethylene oxide: history[edit]

The article states: "The heterocyclic triangular structure of ethylene oxide was not proposed until 1893." However, I suspect that the triangular structure of ethylene oxide was proposed (and in use in the literature) earlier than 1893.

In the journal Nature (April 6, 1893, vol. 47, p. 551), a report states: "The author then proceeds to discuss the orthodox formulae for trimethylene [i.e., cyclopropane], ethylene oxide, and diazoimide [i.e., hydrazoic acid] …". There follows an illustration showing the hypothetical triangular structure of each substance. "The author" (W. H. Perkin) calls these structures "orthodox", which suggests that they've been used widely for some time; i.e., prior to 1893. Ethylene oxide was depicted as having a triangular molecular structure in:

  • 1890: Henry E. Roscoe and Carl Schorlemmer, ed.s A Treatise on Chemistry (New York: D. Appleton and Co., 1890), vol. 3 (The chemistry of the hydrocarbons …), part 2, page 35.
  • 1889: Henry Watts et al., ed.s, Watts' Dictionary of Chemistry (London, England: Longmans, Green, and Co.: 1889), vol. 2, page 490.
  • 1883: Friedrich K. Beilstein, Handbuch der organischen Chemie (Hamburg, Germany: Leopold Voss, 1883), vol. 1, page 392.
  • 1876: Eugen F. von Gorup-Besanez, ed., Lehrbuch der organischen Chemie für den Unterricht auf Universitäten, … (Braunschweig, Germany: Friedrich Vieweg und Sohn, 1876), vol. 2, page 253.

Cwkmail (talk) 18:36, 21 March 2013 (UTC)

Cleansing of typography[edit]

A followup of user talk: Materialscientist #<math> pollution.

I think either “” or “ · · · ” will be possible replacements for a moronic “•••”. Though, “•” for a free radical (i.e. an unpaired electron) is nice, isn’t it? Or, possibly, it should be superscripted, such as in OH? Incnis Mrsi (talk) 14:42, 29 June 2013 (UTC)

Thermodynamic values[edit]

I received the following message from "DVWynn", who noted a difference between 2 sources for the compound's heat of formation--

In The Chemistry of Heterocyclic Compounds, Small Ring Heterocycles edited by Alfred Hassner, page 7-8, the heat of formation [of etylene oxide] is given as 117.2 kJ/mol, [which is] derived from heat of combustion 114.4 kJ/mol, and importantly, the ring-strain is quoted as 54.4 kJ/mol. These are at odds with the values on the page by a HUGE amount. [The ethylene oxide page lists the compound's heat of formation as: Std enthalpy of formation ΔfHo298 = −52.6 kJ mol−1 .] I presume 'angular stress' means ring-strain but maybe my terminology is out of date? Since its main use is in thermobaric weapons, I presume that it packs a lot of energy in a small (by spacial volume) 'package'. Note that heptanitrocubane is preferred over octanitrocubane because its concentration of energy (due to crystal structure) is higher.

Cwkmail (talk) 16:54, 9 July 2013 (UTC)

I did some very quick checking and confirmed that Hassner's book The Chemistry of Heterocyclic Compounds … does indeed list the heat of formation of ethylene oxide as 117.2 kJ/ mol. (See: Heterocyclic Compounds ... by A. Hassner ) However, a couple of other sources may explain the difference in the figures for the compound's heat of formation. The Wikipedia article lists the heat of formation for the compound in its GAS state, whereas the heat of formation is higher for the compound in its LIQUID state. Hassner may have listed the heat of formation for the compound in its LIQUID state.

For example, on page 12 of this pdf file -- American Chemistry.com -- the heat of formation of the GASEOUS form is listed as
-1,194.8 kJ/kg = -52.6 kJ/mol ;
however, the heat of formation of the LIQUID form is listed as
-1,766.5 kJ/kg = -77.8 kJ/mol .
The National Institute of Standards and Technology lists the compound's heat of formation in the GASEOUS state as
-52.6 kJ/mol
However, in the "Comment" section, the heat of formation in the LIQUID state is listed as
-95.7 kJ/mol

So it seems likely that the difference in the heats of formation are the result of using different states (liquid vs. gas) as references for the measurements. However, in order to confirm this, it would be necessary to view Hassner's sources (which he does list). Cwkmail (talk) 17:53, 9 July 2013 (UTC)

Suggestions[edit]

About Ehtylene Oxide producers: in case anyone has the time or care to add this to the article, LyondellBasell also produces this product in Texas, USA according to their website. Reference: Http://www.lyondellbasell.com/Aboutus/WorldWideLocations/NorthAmerica/USA/Texas/Channelview/ — Preceding unsigned comment added by 98.194.50.35 (talk) 15:22, 8 April 2014 (UTC)

NFPA rating is wrong[edit]

According to the diagram it is a 3-4-3 rating (NFPA 704) but when I looked at the source (http://web.archive.org/web/20090804080033/http://www.sonoma-county.org/des/pdf/fire/bulletins/info_bulletin_nfpa_marking2009_04n.pdf) it is actually a 2-4-3. — Preceding unsigned comment added by 2001:610:1908:F000:D82E:D0AA:9CF2:39D3 (talk) 12:02, 27 May 2014 (UTC)