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| CASNo_Ref = {{cascite|correct|??}}
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 22113-86-6
| CASNo = 22113-86-6
| ChEBI = 63882
| EINECS = 690-858-8
| PubChem = 6432248
| PubChem = 6432248
| ChemSpiderID = 4937507
| ChemSpiderID = 4937507
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| SMILES = CC[NH3+].[O-]n(:o):o
| SMILES = CC[NH3+].[N+](=O)([O-])[O-]
| SMILES2 = 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 = 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}}
Line 24: Line 25:
}}
}}
|Section2={{Chembox Properties
|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]</ref>
| 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 = {{Chem|C|2|NH|8|NO|3}}
| Formula = {{chem2|[CH3CH2NH3]+[NO3]−}}
| MolarMass = 108.0965 g mol<sup>−1</sup>
| MolarMass = 108.0965 g/mol
| Density = 1.261 g/ml
| Density = 1.261 g/ml
| Appearance = Colorless liquid
| Appearance = Colorless liquid
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}}
}}
|Section3={{Chembox Thermochemistry
|Section3={{Chembox Thermochemistry
| HeatCapacity = 206 J K<sup>−1</sup> mol<sup>−1</sup>
| HeatCapacity = 206 J/(mol·K)
}}
}}
|Section4={{Chembox Hazards
|Section4={{Chembox Hazards
| ExternalSDS = [http://www.iolitec.de/msds/MSDS-043.pdf External MSDS]
| ExternalSDS = [https://www.carlroth.com/downloads/sdb/en/2/SDB_2035_GB_EN.pdf]
| 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 = {{R36/37/38}}
| SPhrases = {{S24/25}} {{S37/39}}
| 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 {{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&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|title = [http://www.mathnet.ru/links/49e0dd9effca3f2d9c2546eb068f68f3/im6491.pdf 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}}
'''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=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=1-4200-4646-2}}</ref>
</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==
==Synthesis and properties==
Ethylammonium nitrate can be produced by heating [[ethyl nitrate]] 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=1-4097-9043-6}}</ref> or by reacting [[ethylamine]] with concentrated [[nitric acid]].<ref name=walden/> It has a relatively low [[viscosity]] of 0.28 [[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=http://www.carlroth.com/media/_en-de/sdpdf/2035e.PDF|publisher=Carlroth|accessdate=29 August 2012}}</ref>
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 ({{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 [[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 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}}</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==
==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|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|issue=12}}</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=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=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=1-58829-221-5}}</ref>
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==
==References==
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[[Category:Nitrates]]
[[Category:Nitrates]]
[[Category:Ionic liquids]]
[[Category:Ionic liquids]]
[[Category:Substances discovered in the 1910s]]

Latest revision as of 16:36, 8 June 2024

Ethylammonium nitrate
Partially condensed, skeletal formula of ethylammonium nitrate with some explicit hydrogens added
Partially condensed, skeletal formula of ethylammonium nitrate with some explicit hydrogens added
Ball and stick model of ethylammonium nitrate
Ball and stick model of ethylammonium nitrate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.218.244 Edit this at Wikidata
EC Number
  • 690-858-8
  • InChI=1S/C2H7N.NO3/c1-2-3;2-1(3)4/h2-3H2,1H3;/q;-1/p+1 checkY
    Key: AHRQMWOXLCFNAV-UHFFFAOYSA-O checkY
  • InChI=1/C2H7N.NO3/c1-2-3;2-1(3)4/h2-3H2,1H3;/q;-1/p+1
    Key: AHRQMWOXLCFNAV-IKLDFBCSAI
  • CC[NH3+].[N+](=O)([O-])[O-]
Properties[1]
[CH3CH2NH3]+[NO3]−
Molar mass 108.0965 g/mol
Appearance Colorless liquid
Density 1.261 g/ml
Melting point 12 °C (54 °F; 285 K)
Boiling point 240 °C (464 °F; 513 K)
Thermochemistry
206 J/(mol·K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Irritant
GHS labelling:[2]
GHS07: Exclamation mark
Warning
H315, H319, H335
P220, P261, P280, P312
Safety data sheet (SDS) [1]
Related compounds
Other cations
 Methylammonium nitrate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Ethylammonium nitrate or ethylamine nitrate[3] (EAN) is a salt with formula [CH3CH2NH3]+[NO3]−. It is an odorless and colorless to slightly yellowish liquid with a melting point of 12 °C.[4] This compound was described by Paul Walden in 1914,[5][6] and is believed to be the earliest reported example of a room-temperature ionic liquid.[7]

Synthesis and properties

[edit]

Ethylammonium nitrate can be produced by heating ethyl nitrate with an alcoholic solution of ammonia[8] or by reacting ethylamine with concentrated nitric acid.[6] 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.[1] Its density at 20 °C is 1.261 g/cm3.[9]

The ethylammonium ion (CH3CH2NH+3) has three easily detachable protons which are tetrahedrally arranged around the central nitrogen atom, whereas the configuration of the NO−3 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.[10]

Applications

[edit]

Ethylammonium nitrate is used as an electrically conductive solvent in electrochemistry and as a protein crystallization agent.[11][12] 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.[13]

References

[edit]
  1. ^ a b 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, Google patents link[dead link]
  2. ^ "C&L Inventory". echa.europa.eu.
  3. ^ Wagaman, Kerry L Liquid monopropellant United States Patent 6001197, Publication Date 12/14/1999
  4. ^ Marsh, K.N.; Boxall, J.A.; Lichtenthaler, R. (2004). "Room temperature ionic liquids and their mixtures—a review". Fluid Phase Equilibria. 219: 93–98. doi:10.1016/j.fluid.2004.02.003.
  5. ^ P. Walden (1914). Chem. Zentralbl. 85: 1800–1801. {{cite journal}}: Missing or empty |title= (help)
  6. ^ a b P. Walden (1914). "Ueber die Molekulargrösse und elektrische Leitfähigkeit einiger geschmolzenen Salze" (PDF). Bull. Acad. Imper. Sci. St. Pétersbourg. 6. 8: 405–422.
  7. ^ Mihkel Koel (2008). Ionic Liquids in Chemical Analysis. CRC Press. p. xxvii. ISBN 978-1-4200-4646-5.
  8. ^ Rudolph Fittig (2008). Wohler's Outlines of Organic Chemistry. Read Books. p. 56. ISBN 978-1-4097-9043-3.
  9. ^ "Safety Data Sheet" (PDF). Carlroth. Retrieved 19 September 2016.
  10. ^ Allen, Martin; Evans, D. Fennell; Lumry, Rufus (1985). "Thermodynamic properties of the ethylammonium nitrate + water system: Partial molar volumes, heat capacities, and expansivities". Journal of Solution Chemistry. 14 (8): 549. doi:10.1007/BF00649520. S2CID 93627627.
  11. ^ Garlitz, Jennifer A.; Summers, Catherine A.; Flowers, Robert A.; Borgstahl, Gloria E. O. (1999). "Ethylammonium nitrate: a protein crystallization reagent". Acta Crystallographica D. 55 (12): 2037–8. doi:10.1107/S0907444999011774. PMID 10666583.
  12. ^ M. Riad Manaa (2005). Chemistry at extreme conditions. Elsevier. p. 441. ISBN 0-444-51766-9.
  13. ^ Jochen Decker, Udo Reischl (2004). Molecular diagnosis of infectious diseases. Humana Press. p. 247. ISBN 1-58829-221-5.
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