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{{Chembox {{Chembox
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 399923118 | verifiedrevid = 439640871
| ImageFileL1 = Ethylammonium nitrate.png | ImageFileL1 = Ethylammonium nitrate.png
| ImageFileL1_Ref = {{chemboximage|correct|??}} | ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageSizeL1 = 121
| ImageNameL1 = Partially condensed, skeletal formula of ethylammonium nitrate with some explicit hydrogens added | ImageNameL1 = Partially condensed, skeletal formula of ethylammonium nitrate with some explicit hydrogens added
| ImageFileR1 = Ethylammonium-nitrate-3D-balls.png | ImageFileR1 = Ethylammonium-nitrate-3D-balls.png
| ImageFileR1_Ref = {{chemboximage|correct|??}} | ImageFileR1_Ref = {{chemboximage|correct|??}}
| ImageSizeR1 = 121
| ImageNameR1 = Ball and stick model of ethylammonium nitrate | ImageNameR1 = Ball and stick model of ethylammonium nitrate
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 22113-86-6
| PubChem = 6432248 | CASNo = 22113-86-6
| ChEBI = 63882
| PubChem_Ref = {{Pubchemcite|correct|pubchem}}
| EINECS = 690-858-8
⚫ | ChemSpiderID = 4937507
| PubChem = 6432248
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | ChemSpiderID = 4937507
| SMILES = CC.n(:o):o
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| SMILES = CC.(=O)()
| StdInChI = 1S/C2H7N.NO3/c1-2-3;2-1(3)4/h2-3H2,1H3;/q;-1/p+1 | SMILES = CC.(=O)()
| StdInChI = 1S/C2H7N.NO3/c1-2-3;2-1(3)4/h2-3H2,1H3;/q;-1/p+1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| InChI = 1/C2H7N.NO3/c1-2-3;2-1(3)4/h2-3H2,1H3;/q;-1/p+1 | InChI = 1/C2H7N.NO3/c1-2-3;2-1(3)4/h2-3H2,1H3;/q;-1/p+1
| StdInChIKey = AHRQMWOXLCFNAV-UHFFFAOYSA-O | StdInChIKey = AHRQMWOXLCFNAV-UHFFFAOYSA-O
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| InChIKey = AHRQMWOXLCFNAV-IKLDFBCSAI | InChIKey = AHRQMWOXLCFNAV-IKLDFBCSAI
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Reference = <ref name=p1> United States Patent Application 20070026295, </ref> | Properties_ref = <ref name=p1> United States Patent Application 20070026295, {{dead link|date=June 2024|bot=medic}}{{cbignore|bot=medic}}</ref>
| Formula = {{Chem|C|2|NH|8|NO|3}} | Formula = {{chem2|+−}}
| MolarMass = 108.0965 g mol<sup>-1</sup> | MolarMass = 108.0965 g/mol
| Density = 1.261 g/ml
| ExactMass = 108.053492132 g mol<sup>-1</sup>
| Appearance = Colorless liquid | Appearance = Colorless liquid
| MeltingPtC = 12 | MeltingPtC = 12
| BoilingPtC = 240 | BoilingPtC = 240
}} }}
| Section3 = {{Chembox Thermochemistry |Section3={{Chembox Thermochemistry
| HeatCapacity = 90.2 J K<sup>-1</sup> mol<sup>-1</sup> | HeatCapacity = 206 J/(mol·K)
}} }}
| Section4 = {{Chembox Hazards |Section4={{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| MainHazards = Irritant | 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>
| RPhrases = {{R36}} {{R37}} {{R38}}
| GHSPictograms = {{GHS07}}
| SPhrases = {{S24}} {{S25}} {{S37}} {{S39}}
| GHSSignalWord = Warning
⚫ }}
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|220|261|280|312}}
⚫ }}
|Section8={{Chembox Related
| OtherCations=]
}}
}} }}


'''Ethylammonium nitrate''' or '''ethylamine nitrate'''<ref>Wagaman, Kerry L United States Patent 6001197, Publication Date 12/14/1999</ref> (EAN) is a ] with formula {{chem|C|2|H|8|N|2|O|3}} or ({{chem|C|2|H|5}}){{chem|NH|3|+}}·{{chem|NO|3|-}}. It is an odorless and colorless to slightly yellowish liquid with a melting point of 12 °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 ] 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|journal = Bull. Acad. Imper. Sci. St. Pétersbourg| year = 1914|series = 6|volume = 8|pages = 405–422}} '''Ethylammonium nitrate''' or '''ethylamine nitrate'''<ref>Wagaman, Kerry L United States Patent 6001197, Publication Date 12/14/1999</ref> (EAN) is a ] with formula {{chem2|+−}}. 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 ] 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 ].<ref name=r3>{{cite book|url=http://books.google.com/?id=y8d9F7NG60cC&lpg=PR28&pg=PR27|page=xxvii|title=Ionic Liquids in Chemical Analysis|author=Mihkel Koel|publisher=CRC Press|year=2008|isbn=1420046462}}</ref> </ref> and is believed to be the earliest reported example of a room-temperature ].<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== ==Synthesis and properties==
Ethylammonium nitrate can be produced by heating ] with an alcoholic solution of ammonia<ref>{{cite book|url=http://books.google.com/?id=iAJheOVGKIwC&pg=PA56|page=56|title=Wohler's Outlines of Organic Chemistry|author=Rudolph Fittig|publisher=Read Books|year=2008|isbn=1409790436}}</ref> or by reacting ] with concentrated ].<ref name=walden/> It has a relatively low ] of 0.28 ] or 0.028 Pa·s at 25 °C and therefore a high electrical conductivity of about 20 mS·cm<sup>−1</sup> at 25 °C. It boils at 240 °C and decomposes at about 250 °C.<ref name=p1/> Ethylammonium nitrate can be produced by heating ] 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 ] with concentrated ].<ref name=walden/> It has a relatively low ] of 0.28 ] 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 ({{chem|C|2|H|5}}){{chem|NH|3|+}} has three easily detachable protons which are tetrahedrally arranged around the central nitrogen atom, whereas the configuration of the {{chem|NO|3|-}} anion is planar. Despite the structural differences, EAN shares many properties with water, such as ] formation, aggregation of ]s, negative ] and ] of dissolution of gases, etc. Similar to water, EAN can form three-dimensional ]ing networks.<ref>{{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}}</ref> The ethylammonium ion ({{chem2|CH3CH2NH3+}}) has three easily detachable protons which are ] 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 ] formation, aggregation of ]s, negative ] and ] of dissolution of gases, etc. Similar to water, EAN can form three-dimensional ]ing networks.<ref>{{cite journal|doi=10.1007/BF00649520|title=Thermodynamic properties of the ethylammonium nitrate + water system: ]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== ==Applications==
Ethylammonium nitrate is used as an electrically conductive ] in ] and as a protein crystallization agent.<ref>{{cite journal|doi=10.1107/S0907444999011774|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}}</ref><ref>{{cite book|url=http://books.google.com/?id=psRyn7lzGDcC&pg=PA441|page=441|title=Chemistry at extreme conditions|author=M. Riad Manaa|publisher=Elsevier|year=2005|isbn=0444517669}}</ref> It has a positive effect on the refolding of ] ], 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=http://books.google.com/?id=fTluML2hLRsC&pg=PA247|page=247|title=Molecular diagnosis of infectious diseases|author=Jochen Decker, Udo Reischl|publisher=Humana Press|year=2004|isbn=1588292215}}</ref> Ethylammonium nitrate is used as an electrically conductive ] in ] 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 ] ], 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== ==References==
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