Ethyl ether

• Formula: C₄H₁₀O
• Molecular weight: 74.1216
• IUPAC Standard InChI: InChI=1S/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3 Copy

  
• IUPAC Standard InChIKey: RTZKZFJDLAIYFH-UHFFFAOYSA-N Copy
• CAS Registry Number: 60-29-7
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: Ethane, 1,1'-oxybis-; Anaesthetic ether; Anesthesia ether; Anesthetic ether; Diethyl ether; Diethyl oxide; Ethoxyethane; Pronarcol; Solvent ether; 1,1'-Oxybisethane; (C2H5)2O; Aether; Diaethylaether; Dwuetylowy eter; Etere etilico; Ether ethylique; Ether, ethyl; Ethyl ether, tech.; Ethyl oxide; Oxyde d'ethyle; Rcra waste number U117; UN 1155; 3-Oxapentane; Ether; Ethyl ether anhydrous A.C.S.; Sulfuric ether; NSC 100036
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• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Henry's Law data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
• Options:
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Phase change data

Go To: Top, Gas phase ion energetics data, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
    Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kcal/mol)
    T_r = reduced temperature (T / T_c)

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Entropy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Enthalpy of fusion

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

Gas phase ion energetics data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

Appearance energy determinations

References

Go To: Top, Phase change data, Gas phase ion energetics data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Wilhoit, Chao, et al., 1985
Wilhoit, R.C.; Chao, J.; Hall, K.R., Thermodynamic Properties of Key Organic Compounds in the Carbon Range C1 to C4. Part 1. Properties of Condensed Phases, J. Phys. Chem. Ref. Data, 1985, 14, 1. [all data]

Counsell, Lee, et al., 1971
Counsell, J.F.; Lee, D.A.; Martin, J.F., Thermodynamic properties of organic oxygen compounds: xxvi diethyl ether, J. Chem. Soc. A, 1971, 1971, 313-6. [all data]

Parks and Huffman, 1926
Parks, G.S.; Huffman, H.M., Thermal data on organic compounds: IV the heat capacites, entropies, and free energies of normal propyl alcohol, ethyl ether, and dulcitol, J. Am. Chem. Soc., 1926, 48, 2788-93. [all data]

Kobe, Ravicz, et al., 1956
Kobe, K.A.; Ravicz, A.E.; Vohra, S.P., Critical Properties and Vapor Pressures of Some Ethers and Heterocyclic Compounds, J. Chem. Eng. Data, 1956, 1, 50. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Keyes and Beattie, 1924
Keyes, F.G.; Beattie, J.A., A calorimeter for measuring specific heats and heats of vaporization of liquids. The specific heat and heat of vaporization of liquid ethyl ether at 0° and 12°, J. Am. Chem. Soc., 1924, 46, 1753-1760. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Ambrose, Sprake, et al., 1972
Ambrose, D.; Sprake, C.H.S.; Townsend, R., Thermodynamic properties of organic oxygen compounds XXIX. The vapour pressure of diethyl ether, The Journal of Chemical Thermodynamics, 1972, 4, 2, 247-254, https://doi.org/10.1016/0021-9614(72)90063-8 . [all data]

Ambrose, Ellender, et al., 1976
Ambrose, D.; Ellender, J.H.; Sprake, C.H.S.; Townsend, R., Thermodynamic properties of organic oxygen compounds XLIII. Vapour pressures of some ethers, The Journal of Chemical Thermodynamics, 1976, 8, 2, 165-178, https://doi.org/10.1016/0021-9614(76)90090-2 . [all data]

Counsell, Lee, et al., 1971, 2
Counsell, J.F.; Lee, D.A.; Martin, J.F., Thermodynamic properties of organic oxygen compounds. Part XXVI. Diethyl ether, J. Chem. Soc. A, 1971, 313. [all data]

Taylor and Smith, 1922
Taylor, Robert S.; Smith, Leighton B., THE VAPOR PRESSURES, DENSITIES AND SOME DERIVED QUANTITIES FOR ETHER AT LOW TEMPERATURES, J. Am. Chem. Soc., 1922, 44, 11, 2450-2463, https://doi.org/10.1021/ja01432a012 . [all data]

Parks and Huffman, 1926, 2
Parks, G.S.; Huffman, H.M., Thermal data on organic compounds. IV. The heat capacities, entropies and free energies of normal propyl alcohol, ethyl ether and dulcitol, J. Am. Chem. Soc., 1926, 48, 2788-2793. [all data]

Counsell, Lee, et al., 1971, 3
Counsell, J.F.; Lee, D.A.; Martin, J.F., Thermodynamic properties of organic oxygen compounds. Part XXVI. Diethyl ether, 1971, J. [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Bowen and Maccoll, 1984
Bowen, R.D.; Maccoll, A., Low energy, low temperature mass spectra, Org. Mass Spectrom., 1984, 19, 379. [all data]

Botter, Pechine, et al., 1977
Botter, R.; Pechine, J.M.; Rosenstock, H.M., Photoionization of dimethyl ether and diethyl ether, Int. J. Mass Spectrom. Ion Phys., 1977, 25, 7. [all data]

Behan, Dean, et al., 1976
Behan, J.M.; Dean, F.M.; Johnstone, R.A.W., Photoelectron spectra of cyclic aromatic ethers. The question of the Mills-Nixon effect, Tetrahedron, 1976, 32, 167. [all data]

Cocksey, Eland, et al., 1971
Cocksey, B.J.; Eland, J.H.D.; Danby, C.J., The effect of alkyl substitution on ionisation potential, J. Chem. Soc., 1971, (B), 790. [all data]

Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation, J. Chem. Phys., 1969, 50, 654. [all data]

Watanabe, 1957
Watanabe, K., Ionization potentials of some molecules, J. Chem. Phys., 1957, 26, 542. [all data]

Ohno, Imai, et al., 1985
Ohno, K.; Imai, K.; Harada, Y., Variations in reactivity of lone-pair electrons due to intramolecular hydrogen bonding as observed by penning ionization electron spectroscopy, J. Am. Chem. Soc., 1985, 107, 8078. [all data]

Aue and Bowers, 1979
Aue, D.H.; Bowers, M.T., Chapter 9. Stabilities of positive ions from equilibrium gas phase basicity measurements in Ions Chemistry,, ed. M.T. Bowers, 1979. [all data]

Benoit and Harrison, 1977
Benoit, F.M.; Harrison, A.G., Predictive value of proton affinity. Ionization energy correlations involving oxygenated molecules, J. Am. Chem. Soc., 1977, 99, 3980. [all data]

Aue, Webb, et al., 1975
Aue, D.H.; Webb, H.M.; Bowers, M.T., Proton affinities, ionization potentials, and hydrogen affinities of nitrogen and oxygen bases. Hybridization effects, J. Am. Chem. Soc., 1975, 97, 4137. [all data]

Selim and Helal, 1981
Selim, E.T.M.; Helal, A.I., Heat of formation of CH₂=OH⁺ fragment ion, Indian J. Pure Appl. Phys., 1981, 19, 977. [all data]

Holmes, Rye, et al., 1979
Holmes, J.L.; Rye, R.T.B.; Terlouw, J.K., On the loss of ethylene from [C₃H₇O]⁺ ions of structure CH₃CH₂CHOH, Org. Mass Spectrom., 1979, 14, 606. [all data]

Harrison, Ivko, et al., 1966
Harrison, A.G.; Ivko, A.; Van Raalte, D., Energetics of formation of some oxygenated ions and the proton affinities of carbonyl compounds, Can. J. Chem., 1966, 44, 1625. [all data]

Williams and Hamill, 1968
Williams, J.M.; Hamill, W.H., Ionization potentials of molecules and free radicals and appearance potentials by electron impact in the mass spectrometer, J. Chem. Phys., 1968, 49, 4467. [all data]

Lossing, 1977
Lossing, F.P., Heats of formation of some isomeric [C_nH_2n+1]⁺ ions. Substitutional effects on ion stability, J. Am. Chem. Soc., 1977, 99, 7526. [all data]

Phillips, Russell, et al., 1975
Phillips, G.R.; Russell, M.E.; Solka, B.H., The structure of the [C₂H₅O]⁺ ion in the mass spectrum of diethyl ether, Org. Mass Spectrom., 1975, 10, 819. [all data]

Tsang and Harrison, 1970
Tsang, C.W.; Harrison, A.G., Four-centred rearrangements in the mass spectra of aliphatic ethers, Org. Mass Spectrom., 1970, 3, 647. [all data]

Notes

Go To: Top, Phase change data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Vc	Critical volume
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ΔvapS	Entropy of vaporization
  ρc	Critical density

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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