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Ethylammonium nitrate

October 14, 2023

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]

Ethylammonium nitrate
Partially condensed, skeletal formula of ethylammonium nitrate with some explicit hydrogens added
Ball and stick model of ethylammonium nitrate
Identifiers
  • 22113-86-6 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:63882
ChemSpider
  • 4937507 Y
ECHA InfoCard 100.218.244
EC Number
  • 690-858-8
  • 6432248
  • DTXSID0047901
  • InChI=1S/C2H7N.NO3/c1-2-3;2-1(3)4/h2-3H2,1H3;/q;-1/p+1 Y
    Key: AHRQMWOXLCFNAV-UHFFFAOYSA-O Y
  • 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]
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).
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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
  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.

October 14, 2023
ethylammonium, nitrate, ethylamine, nitrate, salt, with, formula, ch3ch2nh3, odorless, colorless, slightly, yellowish, liquid, with, melting, point, this, compound, described, paul, walden, 1914, believed, earliest, reported, example, room, temperature, ionic,. 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 Ethylammonium nitrate Partially condensed skeletal formula of ethylammonium nitrate with some explicit hydrogens added Ball and stick model of ethylammonium nitrateIdentifiersCAS Number 22113 86 6 Y3D model JSmol Interactive imageChEBI CHEBI 63882ChemSpider 4937507 YECHA InfoCard 100 218 244EC Number 690 858 8PubChem CID 6432248CompTox Dashboard EPA DTXSID0047901InChI InChI 1S C2H7N NO3 c1 2 3 2 1 3 4 h2 3H2 1H3 q 1 p 1 YKey AHRQMWOXLCFNAV UHFFFAOYSA O YInChI 1 C2H7N NO3 c1 2 3 2 1 3 4 h2 3H2 1H3 q 1 p 1Key AHRQMWOXLCFNAV IKLDFBCSAISMILES CC NH3 N O O O Properties 1 Chemical formula CH3CH2NH3 NO3 Molar mass 108 0965 g molAppearance Colorless liquidDensity 1 261 g mlMelting point 12 C 54 F 285 K Boiling point 240 C 464 F 513 K ThermochemistryHeat capacity C 206 J mol K HazardsOccupational safety and health OHS OSH Main hazards IrritantGHS labelling 2 PictogramsSignal word WarningHazard statements H315 H319 H335Precautionary statements P220 P261 P280 P312Safety data sheet SDS 1 Related compoundsOther cations Methylammonium nitrateExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox referencesSynthesis and properties EditEthylammonium 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 EditEthylammonium 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 a b Ionic liquids amp 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 C amp L Inventory echa europa eu Wagaman Kerry L Liquid monopropellant United States Patent 6001197 Publication Date 12 14 1999 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 P Walden 1914 Chem Zentralbl 85 1800 1801 a href Template Cite journal html title Template Cite journal cite journal a Missing or empty title help a b P Walden 1914 Ueber die Molekulargrosse und elektrische Leitfahigkeit einiger geschmolzenen Salze PDF Bull Acad Imper Sci St Petersbourg 6 8 405 422 Mihkel Koel 2008 Ionic Liquids in Chemical Analysis CRC Press p xxvii ISBN 978 1 4200 4646 5 Rudolph Fittig 2008 Wohler s Outlines of Organic Chemistry Read Books p 56 ISBN 978 1 4097 9043 3 Safety Data Sheet PDF Carlroth Retrieved 19 September 2016 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 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 M Riad Manaa 2005 Chemistry at extreme conditions Elsevier p 441 ISBN 0 444 51766 9 Jochen Decker Udo Reischl 2004 Molecular diagnosis of infectious diseases Humana Press p 247 ISBN 1 58829 221 5 Retrieved from https en wikipedia org w index php title Ethylammonium nitrate amp oldid 1171071219, wikipedia, wiki, book, books, library,

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