View source for Ethylammonium nitrate

{{Chembox
| Watchedfields = changed
| verifiedrevid = 439640871
| ImageFileL1 = Ethylammonium nitrate.png
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageNameL1 = Partially condensed, skeletal formula of ethylammonium nitrate with some explicit hydrogens added
| ImageFileR1 = Ethylammonium-nitrate-3D-balls.png
| ImageFileR1_Ref = {{chemboximage|correct|??}}
| ImageNameR1 = Ball and stick model of ethylammonium nitrate
|IUPACName=Ethanaminium nitrate
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 22113-86-6
| ChEBI = 63882
| EINECS = 690-858-8
| PubChem = 6432248
| ChemSpiderID = 4937507
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| SMILES = CC[NH3+].[N+](=O)([O-])[O-]
| StdInChI = 1S/C2H7N.NO3/c1-2-3;2-1(3)4/h2-3H2,1H3;/q;-1/p+1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| InChI = 1/C2H7N.NO3/c1-2-3;2-1(3)4/h2-3H2,1H3;/q;-1/p+1
| StdInChIKey = AHRQMWOXLCFNAV-UHFFFAOYSA-O
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| InChIKey = AHRQMWOXLCFNAV-IKLDFBCSAI
 }}
|Section2={{Chembox Properties
| Properties_ref = <ref name=p1>[http://www.freepatentsonline.com/y2007/0026295.html Ionic liquids & ionic liquid acids with high temperature stability for fuel cell and other high temperature applications, method of making and cell employing same] United States Patent Application 20070026295, [http://www.google.com/patents/about?id=bVOZAAAAEBAJ&dq=Ionic+liquids+%26+ionic+liquid+acids+with+high+temperature+stability+for+fuel+cell+and+other+high+temperature+applications,+method+of+making+and+cell+employing+same Google patents link]{{dead link|date=June 2024|bot=medic}}{{cbignore|bot=medic}}</ref>
| Formula = {{chem2|[CH3CH2NH3]+[NO3]−}}
| MolarMass = 108.0965 g/mol
| Density = 1.261 g/ml
| Appearance = Colorless liquid
| MeltingPtC = 12 
| BoilingPtC = 240
 }}
|Section3={{Chembox Thermochemistry
| HeatCapacity = 206 J/(mol·K)
 }}
|Section4={{Chembox Hazards
| ExternalSDS = [https://www.carlroth.com/downloads/sdb/en/2/SDB_2035_GB_EN.pdf]
| MainHazards = Irritant
| GHS_ref=<ref>{{cite web |title=C&L Inventory |url=https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/223676 |website=echa.europa.eu}}</ref>
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|220|261|280|312}}
 }}
|Section8={{Chembox Related
| OtherCations=[[Methylammonium nitrate]]
  }}
}}

'''Ethylammonium nitrate''' or '''ethylamine nitrate'''<ref>Wagaman, Kerry L [http://www.freepatentsonline.com/6001197.html Liquid monopropellant] United States Patent 6001197, Publication Date 12/14/1999</ref> (EAN) is a [[salt (chemistry)|salt]] with formula  {{chem2|[CH3CH2NH3]+[NO3]−}}. It is an odorless and colorless to slightly yellowish liquid with a melting point of 12&nbsp;°C.<ref>{{cite journal|last1 = Marsh|first1 = K.N.|last2 = Boxall|first2 = J.A.|last3 = Lichtenthaler|first3 = R.|title = Room temperature ionic liquids and their mixtures—a review|journal = Fluid Phase Equilibria|volume = 219|doi=10.1016/j.fluid.2004.02.003|year = 2004|pages = 93–98}}</ref> This compound was described by [[Paul Walden]] in 1914,<ref>{{cite journal|author = P. Walden|journal = Chem. Zentralbl.| year = 1914|volume = 85|pages = 1800–1801}}</ref><ref name=walden>{{cite journal|author = P. Walden|url=http://www.mathnet.ru/links/49e0dd9effca3f2d9c2546eb068f68f3/im6491.pdf |title=Ueber die Molekulargrösse und elektrische Leitfähigkeit einiger geschmolzenen Salze|journal = Bull. Acad. Imper. Sci. St. Pétersbourg| year = 1914|series = 6|volume = 8|pages = 405–422}}
</ref> and is believed to be the earliest reported example of a room-temperature [[ionic liquid]].<ref name=r3>{{cite book|url=https://books.google.com/books?id=y8d9F7NG60cC&pg=PR27|page=xxvii|title=Ionic Liquids in Chemical Analysis|author=Mihkel Koel|publisher=CRC Press|year=2008|isbn=978-1-4200-4646-5}}</ref>

==Synthesis and properties==
Ethylammonium nitrate can be produced by heating [[ethyl nitrate]] with an alcoholic solution of ammonia<ref>{{cite book|url=https://books.google.com/books?id=iAJheOVGKIwC&pg=PA56|page=56|title=Wohler's Outlines of Organic Chemistry|author=Rudolph Fittig|publisher=Read Books|year=2008|isbn=978-1-4097-9043-3}}</ref> or by reacting [[ethylamine]] with concentrated [[nitric acid]].<ref name=walden/> It has a relatively low [[viscosity]] of 0.28 [[Poise (unit)|poise]] or 0.028 Pa·s at 25&nbsp;°C and therefore a high electrical conductivity of about 20 mS·cm<sup>−1</sup> at 25&nbsp;°C. It boils at 240&nbsp;°C and decomposes at about 250&nbsp;°C.<ref name=p1/> Its density at 20&nbsp;°C is 1.261 g/cm<sup>3</sup>.<ref>{{cite web|title=Safety Data Sheet|url=https://www.carlroth.com/downloads/sdb/en/2/SDB_2035_GB_EN.pdf|publisher=Carlroth|accessdate=19 September 2016}}</ref> 

The ethylammonium ion ({{chem2|CH3CH2NH3+}}) has three easily detachable protons which are [[tetrahedrally]] arranged around the central nitrogen atom, whereas the configuration of the {{chem2|NO3-}} anion is planar. Despite the structural differences, EAN shares many properties with water, such as [[micelle]] formation, aggregation of [[hydrocarbon]]s, negative [[enthalpy]] and [[entropy]] of dissolution of gases, etc. Similar to water, EAN can form three-dimensional [[hydrogen bond]]ing networks.<ref>{{cite journal|doi=10.1007/BF00649520|title=Thermodynamic properties of the ethylammonium nitrate + water system: [[Partial molar volume]]s, heat capacities, and expansivities|year=1985|last1=Allen|first1=Martin|last2=Evans|first2=D. Fennell|last3=Lumry|first3=Rufus|journal=Journal of Solution Chemistry|volume=14|pages=549|issue=8|s2cid=93627627}}</ref>

==Applications==
Ethylammonium nitrate is used as an electrically conductive [[solvent]] in [[electrochemistry]] and as a protein crystallization agent.<ref>{{cite journal|doi=10.1107/S0907444999011774|pmid=10666583|title=Ethylammonium nitrate: a protein crystallization reagent|year=1999|last1=Garlitz|first1=Jennifer A.|last2=Summers|first2=Catherine A.|last3=Flowers|first3=Robert A.|last4=Borgstahl|first4=Gloria E. O.|journal=Acta Crystallographica D |volume=55|pages=2037–8|issue=12|doi-access=}}</ref><ref>{{cite book|url=https://books.google.com/books?id=psRyn7lzGDcC&pg=PA441|page=441|title=Chemistry at extreme conditions|author=M. Riad Manaa|publisher=Elsevier|year=2005|isbn=0-444-51766-9}}</ref> It has a positive effect on the refolding of [[Denaturation (biochemistry)|denaturated]] [[lysozyme]], with the refolding yield of about 90%. The refolding action was explained as follows: The ethyl group of ethylammonium nitrate interacts with the hydrophobic part of the protein and thereby protects it from intermolecular association, whereas the charged part of EAN stabilizes the electrostatic interactions.<ref>{{cite book|url=https://books.google.com/books?id=fTluML2hLRsC&pg=PA247|page=247|title=Molecular diagnosis of infectious diseases|author=Jochen Decker, Udo Reischl|publisher=Humana Press|year=2004|isbn=1-58829-221-5}}</ref>

==References==
{{reflist}}

[[Category:Ammonium compounds]]
[[Category:Nitrates]]
[[Category:Ionic liquids]]
[[Category:Substances discovered in the 1910s]]