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Revision as of 00:19, 13 May 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit Latest revision as of 23:51, 10 December 2024 edit undoCitation bot (talk | contribs)Bots5,418,803 edits Add: bibcode, authors 1-1. Removed parameters. Some additions/deletions were parameter name changes. | Use this bot. Report bugs. | Suggested by Graeme Bartlett | #UCB_toolbar 
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{{distinguish|nitroethane|ethyl nitrite}}
{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 412892906
| Watchedfields = changed
⚫ | ImageFile = Ethyl Nitrate Structural Formulae V.1.svg
⚫ | verifiedrevid = 428846955
⚫ | ImageSize =
⚫ | ImageFile = Ethyl Nitrate Structural Formulae V.1.svg
⚫ | IUPACName = Ethyl nitrate
⚫ | ImageSize = 160
⚫ | OtherNames = Nitric acid ethyl ester
| ImageAlt = Skeletal formula of ethyl nitrate
⚫ | Section1 = {{Chembox Identifiers
| ImageFile1 = Ethyl nitrate 3D ball.png
| ImageSize1 = 160
| ImageAlt1 = Ball-and-stick model of the ethyl nitrate molecule
⚫ | PIN = Ethyl nitrate
⚫ | OtherNames = Nitric acid ethyl ester
| IUPACName = 1-Nitrosooxyethane
⚫ | Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 625-58-1 | CASNo = 625-58-1
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 11756
| EC_number = 210-903-3
| PubChem = 12259 | PubChem = 12259
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = E1ZT886LR5
| UNNumber = 1993
| InChI = 1/C2H5NO3/c1-2-6-3(4)5/h2H2,1H3
| InChIKey = IDNUEBSJWINEMI-UHFFFAOYAM
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C2H5NO3/c1-2-6-3(4)5/h2H2,1H3
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = IDNUEBSJWINEMI-UHFFFAOYSA-N
| SMILES = CCO(=O) | SMILES = CCO(=O)
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| C = 2 | H = 5 | N = 1 | O = 3
| Formula = C<sub>2</sub>H<sub>5</sub>NO<sub>3</sub>
| Appearance = colorless liquid
| MolarMass = 91.07 g/mol
| Appearance = Liquid | Odor = sweet
| Density = | Density = 1.10g/cm<sup>3</sup>
| MeltingPt = −102 °C | MeltingPtC = −102
| BoilingPt = 87 °C | BoilingPtC = 87.5
| Solubility = | Solubility = soluble
}} }}
| Section3 = {{Chembox Hazards | Section3 = {{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | NFPA-H = 2
| Autoignition = | NFPA-F = 3
| NFPA-R = 4
| NFPA-S =
| FlashPtF = -34
| AutoignitionPtC =
| ExploLimits = 4.1%-50%
| GHS_ref=
| GHSPictograms = {{GHS01}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|200}}
| PPhrases = {{P-phrases|201|202|281|372|373|380|401|501}}
}} }}
| Section8 = {{Chembox Related | Section8 = {{Chembox Related
| Function = ]s | OtherFunction_label = ]s
| OtherFunctn = ]<br />]<br />] | OtherFunction = ]<br />]<br />]
}} }}
}} }}


'''Ethyl nitrate''' has formula {{carbon|2}}{{hydrogen|5}}{{nitrogen}}{{oxygen|3}}. It is used in ] and as an intermediate in the preparation of some ], ]s, and ]s.{{fact|date=September 2007}} '''Ethyl nitrate''' is the ] ] of ] and has the ] {{chem2|C2H5NO3|auto=1}}. It is a colourless, volatile, explosive, and extremely flammable liquid. It is used in ] with use as a nitrating agent and as an intermediate in the preparation of some ], ]s, and ]s.<ref>{{Cite book|title=Aromatic nitration|author=Schofield, Kenneth|date=1980|publisher=Cambridge University Press|isbn=9780521233620|location=Cambridge|oclc=6357479|page=94}}</ref> Like ], it's a ].


Ethyl nitrate is found in the atmosphere, where it can react with other gases to form smog. Originally thought to be a ], formed mainly by the ] of ], recent analysis of ] water samples reveal that in places where cool water rises from the deep, the water is ] with alkyl nitrates, likely formed by natural processes.<ref>{{cite news Ethyl nitrate is found in the atmosphere, where it can react with other gases to form smog. The ] was originally thought to have been formed mainly by the ] of ]. However recent analysis of ] water samples reveal that in places where cool water rises from the deep, the water is ] with alkyl nitrates, likely formed by natural processes.<ref>{{cite news
| title =Ocean yields gases that had seemed humanmade | title =Ocean yields gases that had seemed humanmade
| author =S. Perkins | author =S. Perkins
| publisher = ] | publisher = ]
| date = August 12, 2002 | date = August 12, 2002
| url = http://sciencenews.org/articles/20020817/fob8ref.asp | url = https://www.sciencenews.org/article/natures-own-ocean-yields-gases-had-seemed-humanmade
}} }}</ref>

</ref>
==History and synthesis==
Reaction of ethanol with nitric acid was investigated since the Middle Ages, but the fact that it produces mostly ] was not discovered until the 19th century. ] was the first to synthesize ethyl nitrate in 1843 by adding ] to the mixture in order to remove any ].<ref>{{Cite book |last1=Roscoe |first1=Henry Enfield |url=https://books.google.com/books?id=eq-WSFGQX5wC&pg=PA359 |title=A Treatise on Chemistry: The chemistry of the hydrocarbons and their derivatives, or, Organic chemistry |last2=Schorlemmer |first2=Carl |date=1881 |publisher=Macmillan |language=en}}</ref><ref>{{Cite book |url=https://books.google.com/books?id=J6hJAQAAMAAJ&pg=PA233 |title=Annales de chimie et de physique |date=1843 |publisher=Masson. |language=fr}}</ref>

Ethyl nitrate can be prepared by ] ethanol with fuming nitric acid or a mixture of concentrated sulfuric and nitric acids. Besides decomposing nitrous acid, the aforementioned necessary addition of urea prevents explosion.<ref>{{Cite book |last=William M. Cumming |first=I. Vance Hopper |url=http://archive.org/details/Cumming1937 |title=Systematic Organic Chemistry 3ed |date=1937}}</ref> Further purifying by distillation carries a risk of explosion.<ref>{{Cite book |last=Cohen |first=Julius B. (Julius Berend) |url=https://archive.org/details/theoreticalorgan00coherich |title=Theoretical organic chemistry |date=1920 |publisher=London, Macmillan |others=University of California Libraries |page=}}</ref>


⚫ Ethyl nitrate has also been prepared by bubbling gaseous ] through ] at −10&nbsp;°C.<ref>{{cite journal
==Preparation==
⚫ | title =Nitryl fluoride as a nitrating agent
⚫ Ethyl nitrate has been prepared by bubbling gaseous ] through ] at −10 °C.<ref>{{cite journal
⚫ | title=Nitryl fluoride as a nitrating agent
| author =G. Hetherington and R. L. Robinson | author =G. Hetherington and R. L. Robinson
| date = 1954 | date = 1954
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| doi = 10.1039/JR9540003512 | doi = 10.1039/JR9540003512
| pages = 3512 | pages = 3512
⚫ }}</ref> The reaction was subsequently studied in detail.<ref>{{cite journal
}}
⚫ </ref> The reaction was subsequently studied in detail.<ref>{{cite journal
| author =B. S. Fedorov and L. T. Eremenko | author =B. S. Fedorov and L. T. Eremenko
|title= Nitration of alcohols by nitryl fluoride | title = Nitration of alcohols by nitryl fluoride
| date = 1997 | date = 1997
| volume = 46 | volume = 46
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| pages = 1022–1023 | pages = 1022–1023
}} }}
</ref><ref>Explosives, 6th Edition, R. Meyer, J. Kohler, A. Homburg; page 125</ref>
</ref>

A ] of ethyl halides and silver nitrate can also yield ethyl nitrate. Again, purification poses explosion risks.

==Chemical reactions==
Ethyl nitrate can be reduced with ] to form ], though product separation is somewhat difficult.<ref>{{Cite journal |last=Dumreicher |first=Oscar Freih v. |date=December 1880 |title=Untersuchungen über die Einwirkung von Zinnchlorür auf die Stickstoffsauerstoffverbindungen |url=http://link.springer.com/10.1007/BF01517102 |journal=Monatshefte für Chemie |language=de |volume=1 |issue=1 |pages=724–754 |doi=10.1007/BF01517102 |issn=0026-9247}}</ref>

==Explosive properties==
Ethyl nitrate is a sensitive explosive that is prone to detonating upon impact or high temperatures, though is less so than ]. It has a detonation velocity of 6,010&nbsp;m/s,<ref>{{Cite journal |last=Kozak |first=G. D. |date=September 1998 |title=Measurement and calculation of the ideal detonation velocity for liquid nitrocompounds |url=http://link.springer.com/10.1007/BF02672682 |journal=Combustion, Explosion, and Shock Waves |language=en |volume=34 |issue=5 |pages=581–586 |doi=10.1007/BF02672682 |bibcode=1998CESW...34..581K |issn=0010-5082}}</ref> and is therefore a ].


==References== ==References==
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