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
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Phase change 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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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Constant pressure heat capacity of gas

Gas Phase Heat Capacity (Shomate Equation)

C_p° = A + B*t + C*t² + D*t³ + E/t²
H° − H°_298.15= A*t + B*t²/2 + C*t³/3 + D*t⁴/4 − E/t + F − H
S° = A*ln(t) + B*t + C*t²/2 + D*t³/3 − E/(2*t²) + G
    C_p = heat capacity (cal/mol*K)
    H° = standard enthalpy (kcal/mol)
    S° = standard entropy (cal/mol*K)
    t = temperature (K) / 1000.

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Condensed phase thermochemistry 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 compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase 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 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

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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:
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, Gas phase thermochemistry data, Condensed phase thermochemistry 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.

Chase, 1998
Chase, M.W., Jr., NIST-JANAF Themochemical Tables, Fourth Edition, J. Phys. Chem. Ref. Data, Monograph 9, 1998, 1-1951. [all data]

Pell and Pilcher, 1965
Pell, A.S.; Pilcher, G., Measurements of heats of combustion by flame calorimetry. Part 3.-Ethylene oxide, trimethylene oxide, tetrahydrofuran and tetrahydropy, Trans. Faraday Soc., 1965, 61, 71-77. [all data]

Moureu and Dode, 1937
Moureu, H.; Dode, M., Chaleurs de formation de l'oxyde d'ethylene, de l'ethanediol et de quelques homologues, Bull. Soc. Chim. France, 1937, 4, 637-647. [all data]

Crog and Hunt, 1942
Crog, R.S.; Hunt, H., Heats of combustion. II. The heats of combustion of ethyl methyl ketone and ethylene oxide, J. Phys. Chem., 1942, 46, 1162-1163. [all data]

Dorofeeva O.V., 1992
Dorofeeva O.V., Ideal gas thermodynamic properties of oxygen heterocyclic compounds. Part 1. Three-membered, four-membered and five-membered rings, Thermochim. Acta, 1992, 194, 9-46. [all data]

Godnev I., 1948
Godnev I., Thermodynamic functions of ethylene oxide, Zh. Fiz. Khim., 1948, 22, 801-803. [all data]

Gunthard H., 1948
Gunthard H., Thermodynamic properties of ethylene oxide, Helv. Chim. Acta, 1948, 31, 2128-2132. [all data]

Kobe K.A., 1950
Kobe K.A., Thermochemistry for the petrochemical industry. XIII. Some oxygenated hydrocarbons C1 and C2, Petrol. Refiner, 1950, 29 (9), 135-138. [all data]

Sundaram S., 1963
Sundaram S., Thermodynamic functions of some propellants, Z. Phys. Chem. (Frankfurt), 1963, 36, 376-377. [all data]

Ramasamy R., 1978
Ramasamy R., Centrifugal distortion constants and thermodynamic functions of ethylene oxide, ethylene oxide-d4, and ethylene sulfide, Curr. Sci., 1978, 47, 668-669. [all data]

Chao J., 1986
Chao J., Thermodynamic properties of key organic oxygen compounds in the carbon range C1 to C4. Part 2. Ideal gas properties, J. Phys. Chem. Ref. Data, 1986, 15, 1369-1436. [all data]

Kistiakowsky G.B., 1940
Kistiakowsky G.B., Gaseous heat capacities. III, J. Chem. Phys., 1940, 8, 618-622. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Giauque and Gordon, 1949
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]

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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  Cp,liquid	Constant pressure heat capacity of liquid
  IE (evaluated)	Recommended ionization energy
  S°gas,1 bar	Entropy of gas at standard conditions (1 bar)
  S°liquid	Entropy of liquid at standard conditions
  ΔcH°gas	Enthalpy of combustion of gas at standard conditions
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

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