Ethylene oxide

• Formula: C₂H₄O
• Molecular weight: 44.0526
• IUPAC Standard InChI: InChI=1S/C2H4O/c1-2-3-1/h1-2H2 Copy

  
• IUPAC Standard InChIKey: IAYPIBMASNFSPL-UHFFFAOYSA-N Copy
• CAS Registry Number: 75-21-8
• 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: Oxirane; Dihydrooxirene; Dimethylene oxide; Epoxyethane; Ethene oxide; ETO; Oxacyclopropane; Oxane; Oxidoethane; Oxirene, dihydro-; Oxyfume; Oxyfume 12; T-Gas; 1,2-Epoxyethane; Aethylenoxid; Amprolene; Anprolene; Anproline; ENT-26263; E.O.; 1,2-Epoxyaethan; Ethyleenoxide; Etylenu tlenek; FEMA No. 2433; Merpol; NCI-C50088; α,β-Oxidoethane; Oxiraan; Oxiran; Rcra waste number U115; Sterilizing gas ethylene oxide 100%; UN 1040; Qazi-ketcham
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Vibrational and/or electronic energy levels
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Phase change data

Go To: Top, Reaction thermochemistry data, 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Enthalpy of vaporization

Entropy of vaporization

Antoine Equation Parameters

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

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Enthalpy of fusion

Entropy of fusion

Reaction thermochemistry data

Go To: Top, Phase change data, 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

=  + 2

By formula: C₁₆H₃₅NO₂ = C₁₂H₂₇N + 2C₂H₄O

=  + 

By formula: C₁₄H₃₁NO = C₁₂H₂₇N + C₂H₄O

Gas phase ion energetics data

Go To: Top, Phase change data, Reaction thermochemistry data, References, Notes

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:
LL - Sharon G. Lias and Joel F. Liebman
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

View reactions leading to C₂H₄O⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

References

Go To: Top, Phase change data, Reaction thermochemistry 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.

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]

Moureu and Dode, 1937
Moureu, H.; Dode, M., Heats of Formation of Ethylene Oxide, of Ethandiol and oof Several Homologs, Bull. Soc. Chim. Fr., 1937, 4, 637-47. [all data]

Timmermans and Hennaut-Roland, 1937
Timmermans, J.; Hennaut-Roland, M., Works from International Bureau at Physical-Chemical Standards. VIII. Physical constants of 20 organic compounds, J. Chim. Phys. Phys.-Chim. Biol., 1937, 34, 693. [all data]

Maass and Boomer, 1922
Maass, O.; Boomer, E.H., Vapor Densities at Low Pressures and Over and Extended Temperature Range. I. The Properties of Ethylene Oxide Compared to Oxygen Compounds of Similar Molecular Weight, J. Am. Chem. Soc., 1922, 44, 8, 1709-1728, https://doi.org/10.1021/ja01429a013 . [all data]

Von Auwers and Eisenlohr, 1910
Von Auwers, K.; Eisenlohr, F., Spectrochemical studies. I. Refraction & dispersion of hydrocarbon aldehydes, ketones, acids & esters with i pair of conjug. double bonds, J. Prakt. Chem., 1910, 82, 65. [all data]

McDonald, Shrader, et al., 1959
McDonald, R.A.; Shrader, S.A.; Stull, D.R., Vapor Pressures and Freezing Points of 30 Organics, J. Chem. Eng. Data, 1959, 4, 311. [all data]

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]

Giauque and Gordon, 1949
Giauque, W.F.; Gordon, J., The entropy of ethylene oxide heat capacity from 14 to 285c vapor pressure heats of fusion and vaporization, J. Am. Chem. Soc., 1949, 71, 2176. [all data]

Walters and Smith, 1952
Walters, C.J.; Smith, J.M., Volumetric Behaviour and Thermodynamic Properties of Ethylene Oxide, Chem. Eng. Prog., 1952, 48, 337. [all data]

Hess and Tilton, 1950
Hess, L.G.; Tilton, V.V., Ethylene Oxide - Hazards and Methods of Handling., Ind. Eng. Chem., 1950, 42, 1251-8. [all data]

Post, 1950
Post, R.G., , Unpublished Rep., Chem. Eng. No. 362, 1950. [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]

Giauque and Gordon, 1949, 2
Giauque, W.F.; Gordon, J., The entropy of ethylene oxide. Heat capacity from 14 to 285K. Vapor pressure. Heats of fusion and vaporization, J. Am. Chem. Soc., 1949, 71, 2176-2181. [all data]

McDonald, Shrader, et al., 1959, 2
McDonald, R.A.; Shrader, S.A.; Stull, D.R., Vapor Pressures and Freezing Points of Thirty Pure Organic Compounds., J. Chem. Eng. Data, 1959, 4, 4, 311-313, https://doi.org/10.1021/je60004a009 . [all data]

Dykyj, 1970
Dykyj, J., Petrochemica, 1970, 10, 2, 51. [all data]

Giauque and Gordon, 1949, 3
Giauque, W.F.; Gordon, J., The entropy of ethylene oxide. Heat capacity from 14 to 285°K. Vapor pressure. Heats of fusion and vaporization, J. Am. Chem. Soc., 1949, 71, 2176-21. [all data]

Moor, Kanep, et al., 1937
Moor, V.G.; Kanep, E.K.; Dobkin, I.E., Trans. Exptl. Research Lab. Khemgas, Materials on Cracking and Chemical Treatment of Cracking Products U.S.S.R., 1937, 3, 320. [all data]

Coles and Popper, 1950
Coles, K.F.; Popper, Felix, Vapor-Liquid Equilibria. Ethylene Oxide - Acetaldehyde and Ethylene Oxide - Water Systems, Ind. Eng. Chem., 1950, 42, 7, 1434-1438, https://doi.org/10.1021/ie50487a046 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Balcerowiak, Jerzykiewicz, et al., 1984
Balcerowiak, W.; Jerzykiewicz, W.; Szewczyk, H., Differential thermal analysis using closed pans. The ethoxylation of n-dodecylamine, Tenside Deterg., 1984, 21, 10-11. [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]

Holmes and Lossing, 1991
Holmes, J.L.; Lossing, F.P., Ionization energies of homologous organic compounds and correlation with molecular size, Org. Mass Spectrom., 1991, 26, 537. [all data]

Aue, Webb, et al., 1980
Aue, D.H.; Webb, H.M.; Davidson, W.R.; Vidal, M.; Bowers, M.T.; Goldwhite, H.; Vertal, L.E.; Douglas, J.E.; Kollman, P.A.; Kenyon, G.L., Proton affinities photoelectron spectra of three-membered-ring J. Heterocycl. Chem., J. Am. Chem. Soc., 1980, 102, 5151. [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]

Holmes, Terlouw, et al., 1976
Holmes, J.L.; Terlouw, J.K.; Lossing, F.P., The thermochemistry of C₂H₄O⁺ ions, J. Phys. Chem., 1976, 80, 2860. [all data]

Corderman, LeBreton, et al., 1976
Corderman, R.R.; LeBreton, P.R.; Buttrill, S.E., Jr.; Williamson, A.D.; Beauchamp, J.L., Photoionization and ion cyclotron resonance studies of the ion chemistry of ethylene oxide, J. Chem. Phys., 1976, 65, 4929. [all data]

Krassig, Reinke, et al., 1974
Krassig, R.; Reinke, D.; Baumgartel, H., Photo-reaktionen kleiner organischer molekule II. Die photoionenspektren der Isomeren propylen-cyclopropan und acetaldehyd-athylenoxyd, Ber. Bunsen-Ges. Phys. Chem., 1974, 78, 425. [all data]

Basch, Robin, et al., 1969
Basch, H.; Robin, M.B.; Kuebler, N.A.; Baker, C.; Turner, D.W., Optical and photoelectron spectra of small rings. III. The saturated three-membered rings, J. Chem. Phys., 1969, 51, 52. [all data]

Lowrey and Watanabe, 1958
Lowrey, A., III; Watanabe, K., Absorption and ionization coefficients of ethylene oxide, J. Chem. Phys., 1958, 28, 208. [all data]

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

Vorob'ev, Furlei, et al., 1989
Vorob'ev, A.S.; Furlei, I.I.; Sultanov, A.S.; Khvostenko, V.I.; Leplyanin, G.V.; Derzhinskii, A.R.; Tolstikov, G.A., Mass spectrometry of reasonance capture of electrons and photoelectron spectroscopy of molecules of ethylene oxide, ethylene sulfide, and their derivatives, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1989, 1388. [all data]

Johnson, Powis, et al., 1982
Johnson, K.; Powis, I.; Danby, C.J., A photoelectron-photoion coincidence study of acetaldehyde and ethylene oxide molecular ions, Chem. Phys., 1982, 70, 329. [all data]

Bieri, Asbrink, et al., 1982
Bieri, G.; Asbrink, L.; Von Niessen, W., 30.4-nm He(II) photoelectron spectra of organic molecules, J. Electron Spectrosc. Relat. Phenom., 1982, 27, 129. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [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]

Gallegos and Kiser, 1961
Gallegos, E.J.; Kiser, R.W., Electron impact spectroscopy of ethylene oxide and propylene oxide, J. Am. Chem. Soc., 1961, 83, 773. [all data]

Burgers and Holmes, 1982
Burgers, P.C.; Holmes, J.L., Metastable ion studies. XIII. The measurement of appearance energies of metastable peaks, Org. Mass Spectrom., 1982, 17, 123. [all data]

Notes

Go To: Top, Phase change data, Reaction thermochemistry 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
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrH°	Enthalpy of reaction at standard conditions
  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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