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
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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 | -95.7 ± 1.3 | kJ/mol | Ccb | Moureu and Dode, 1937 | Reanalyzed by Cox and Pilcher, 1970, Original value = -95.4 kJ/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1262.9 ± 1.3 | kJ/mol | Ccb | Moureu and Dode, 1937 | Reanalyzed by Cox and Pilcher, 1970, Original value = -1264. kJ/mol; Corresponding ΔfHºliquid = -95.73 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 149.45 | J/mol*K | N/A | Giauque and Gordon, 1949 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
86.90 | 285. | Giauque and Gordon, 1949 | T = 15 to 283 K.; DH |
Phase change data
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 283.7 | K | N/A | Majer and Svoboda, 1985 | |
Tboil | 286.15 | K | N/A | Moureu and Dode, 1937, 2 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tboil | 283.85 | K | N/A | Timmermans and Hennaut-Roland, 1937 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tboil | 283.88 | K | N/A | Maass and Boomer, 1922 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tboil | 286. | K | N/A | Von Auwers and Eisenlohr, 1910 | Uncertainty assigned by TRC = 4. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 160.6 | K | N/A | McDonald, Shrader, et al., 1959 | Uncertainty assigned by TRC = 0.07 K; TRC |
Tfus | 161.45 | K | N/A | Timmermans and Hennaut-Roland, 1937 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tfus | 161.9 | K | N/A | Maass and Boomer, 1922 | Uncertainty assigned by TRC = 0.6 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 160.65 | K | N/A | Wilhoit, Chao, et al., 1985 | Uncertainty assigned by TRC = 0.05 K; TRC |
Ttriple | 160.65 | K | N/A | Giauque and Gordon, 1949, 2 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 468.9 | K | N/A | Walters and Smith, 1952 | Uncertainty assigned by TRC = 1.11 K; TRC |
Tc | 469.0 | K | N/A | Hess and Tilton, 1950 | Uncertainty assigned by TRC = 1. K; TRC |
Tc | 465.2 | K | N/A | Maass and Boomer, 1922 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 72.33 | bar | N/A | Walters and Smith, 1952 | Uncertainty assigned by TRC = 0.6894 bar; TRC |
Pc | 71.91 | bar | N/A | Hess and Tilton, 1950 | Uncertainty assigned by TRC = 0.7584 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 7.13 | mol/l | N/A | Walters and Smith, 1952 | Uncertainty assigned by TRC = 0.23 mol/l; TRC |
ρc | 7.26 | mol/l | N/A | Post, 1950 | Uncertainty assigned by TRC = 0.23 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 25.51 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 25.9 | kJ/mol | A | Stephenson and Malanowski, 1987 | Based on data from 283. to 385. K.; AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
25.527 | 283.66 | N/A | Giauque and Gordon, 1949 | P = 101.325 kPa; DH |
25.54 | 283.7 | N/A | Majer and Svoboda, 1985 | |
26.8 | 269. | A | Stephenson and Malanowski, 1987 | Based on data from 239. to 284. K. See also McDonald, Shrader, et al., 1959, 2 and Dykyj, 1970.; AC |
26.8 | 269. | A | Stephenson and Malanowski, 1987 | Based on data from 223. to 284. K. See also Giauque and Gordon, 1949.; AC |
25.5 ± 0.3 | 283.66 | V | Giauque and Gordon, 1949, 3 | ALS |
26.9 | 290. | N/A | Moor, Kanep, et al., 1937 | Based on data from 268. to 313. K.; AC |
Entropy of vaporization
ΔvapS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
89.99 | 283.66 | Giauque and Gordon, 1949 | P; DH |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
182.59 to 283.59 | 4.386 | 1115.1 | -29.015 | McDonald, Shrader, et al., 1959, 2 | |
273.4 to 304.9 | 5.84696 | 2022.83 | 62.656 | Coles and Popper, 1950 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
5.1731 | 160.65 | Giauque and Gordon, 1949 | DH |
5.17 | 160.7 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
32.20 | 160.65 | Giauque and Gordon, 1949 | DH |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), 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) | 774.2 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 745.3 | kJ/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
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
NIST MS number | 18867 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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]
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, 2
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, 2
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]
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]
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, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy Pc Critical pressure S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions 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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