Ethylene oxide
- Formula: C2H4O
- Molecular weight: 44.0526
- IUPAC Standard InChIKey: IAYPIBMASNFSPL-UHFFFAOYSA-N
- 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:
- Other data available:
- Data at other public NIST sites:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Condensed phase thermochemistry 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -22.88 ± 0.30 | kcal/mol | Ccb | Moureu and Dode, 1937 | Reanalyzed by Cox and Pilcher, 1970, Original value = -22.8 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -301.85 ± 0.30 | kcal/mol | Ccb | Moureu and Dode, 1937 | Reanalyzed by Cox and Pilcher, 1970, Original value = -302.0 kcal/mol; Corresponding ΔfHºliquid = -22.88 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 35.719 | cal/mol*K | N/A | Giauque and Gordon, 1949 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
20.77 | 285. | Giauque and Gordon, 1949 | T = 15 to 283 K.; DH |
Reaction thermochemistry data
Go To: Top, 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
By formula: C16H35NO2 = C12H27N + 2C2H4O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -240.0 ± 6.5 | kcal/mol | Eqk | Balcerowiak, Jerzykiewicz, et al., 1984 | solid phase |
By formula: C14H31NO = C12H27N + C2H4O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -28.7 ± 1.1 | kcal/mol | Eqk | Balcerowiak, Jerzykiewicz, et al., 1984 | liquid phase |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry 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)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 10.56 ± 0.01 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 185.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 178.1 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.15 ± 0.05 | EI | Holmes and Lossing, 1991 | LL |
10.4 ± 0.1 | PE | Aue, Webb, et al., 1980 | LLK |
10.4 | PE | Aue and Bowers, 1979 | LLK |
10.57 | EI | Holmes, Terlouw, et al., 1976 | LLK |
10.6 ± 0.1 | PI | Corderman, LeBreton, et al., 1976 | LLK |
10.560 | PE | Corderman, LeBreton, et al., 1976 | LLK |
10.56 ± 0.01 | PI | Krassig, Reinke, et al., 1974 | LLK |
10.57 | PE | Basch, Robin, et al., 1969 | RDSH |
10.566 | S | Lowrey and Watanabe, 1958 | RDSH |
10.57 ± 0.01 | PI | Watanabe, 1957 | RDSH |
10.57 | EI | Vorob'ev, Furlei, et al., 1989 | Vertical value; LL |
10.57 | PIPECO | Johnson, Powis, et al., 1982 | Vertical value; LBLHLM |
10.57 | PE | Bieri, Asbrink, et al., 1982 | Vertical value; LBLHLM |
10.57 | PE | Kimura, Katsumata, et al., 1981 | Vertical value; LLK |
10.568 | PE | Aue, Webb, et al., 1975 | Vertical value; LLK |
Appearance energy determinations
References
Go To: Top, 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.
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]
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, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy S°liquid Entropy of liquid at standard conditions ΔcH°liquid Enthalpy of combustion of liquid 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
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.