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
| 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
| 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 nitrateWagaman, Kerry L [http://www.freepatentsonline.com/6001197.html Liquid monopropellant] United States Patent 6001197, Publication Date 12/14/1999 (EAN) is a salt with formula {{chem2|[CH3CH2NH3]+[NO3]−}}. It is an odorless and colorless to slightly yellowish liquid with a melting point of 12 °C.{{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}} This compound was described by Paul Walden in 1914,{{cite journal|author = P. Walden|journal = Chem. Zentralbl.| year = 1914|volume = 85|pages = 1800–1801}}{{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}}
and is believed to be the earliest reported example of a room-temperature ionic liquid.{{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}}
Synthesis and properties
Ethylammonium nitrate can be produced by heating ethyl nitrate with an alcoholic solution of ammonia{{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}} or by reacting ethylamine with concentrated nitric acid. It has a relatively low viscosity of 0.28 poise or 0.028 Pa·s at 25 °C and therefore a high electrical conductivity of about 20 mS·cm−1 at 25 °C. It boils at 240 °C and decomposes at about 250 °C. Its density at 20 °C is 1.261 g/cm3.{{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}}
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 hydrocarbons, negative enthalpy and entropy of dissolution of gases, etc. Similar to water, EAN can form three-dimensional hydrogen bonding networks.{{cite journal|doi=10.1007/BF00649520|title=Thermodynamic properties of the ethylammonium nitrate + water system: Partial molar volumes, 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}}
Applications
Ethylammonium nitrate is used as an electrically conductive solvent in electrochemistry and as a protein crystallization agent.{{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=}}{{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}} It has a positive effect on the refolding of 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.{{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}}