Ethene, ethoxy-

Formula: C₄H₈O
Molecular weight: 72.1057
IUPAC Standard InChI: InChI=1S/C4H8O/c1-3-5-4-2/h3H,1,4H2,2H3
IUPAC Standard InChIKey: FJKIXWOMBXYWOQ-UHFFFAOYSA-N
CAS Registry Number: 109-92-2
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: Vinamar; Ether, ethyl vinyl; Ethoxyethene; Ethoxyethylene; Ethyl vinyl ether; EVE; Vinyl ethyl ether; 1-Ethoxyethene; CH2=CHOC2H5; Ethyl ethenyl ether; Ether, vinyl ethyl; 1-Ethoxyethylene; Ethyloxyethene; NSC 8405; ((Vinyl)oxy)ethane
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Gas phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	-33.50 ± 0.23	kcal/mol	Cm	Pilcher, Skinner, et al., 1963
Δ_fH°_gas	-33.48 ± 0.23	kcal/mol	Ccb	Pilcher, Skinner, et al., 1963	Heat of formation derived by Cox and Pilcher, 1970
Δ_fH°_gas	-33.78 ± 0.22	kcal/mol	Chyd	Dolliver, Gresham, et al., 1938	Heat of formation derived by Cox and Pilcher, 1970
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_gas	-615.98 ± 0.22	kcal/mol	Cm	Pilcher, Skinner, et al., 1963	Corresponding Δ_fHº_gas = -33.48 kcal/mol (simple calculation by NIST; no Washburn corrections)

Condensed phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_liquid	-39.83 ± 0.39	kcal/mol	Ccb	Pilcher, Skinner, et al., 1963	Heat of formation derived by Cox and Pilcher, 1970
Δ_fH°_liquid	-40.13 ± 0.39	kcal/mol	Chyd	Dolliver, Gresham, et al., 1938	Heat of formation derived by Cox and Pilcher, 1970
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-607.0 ± 2.5	kcal/mol	Ccb	Favorskii and Shostakovskii, 1943	Corresponding Δ_fHº_liquid = -42.5 kcal/mol (simple calculation by NIST; no Washburn corrections)

Phase change data

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

Quantity	Value	Units	Method	Reference	Comment
T_boil	306.2	K	N/A	Aldrich Chemical Company Inc., 1990	BS
T_boil	306.	K	N/A	Farchan Laboratories, 1990	BS
T_boil	308.7	K	N/A	Weast and Grasselli, 1989	BS
T_boil	308.65	K	N/A	Owen and Sorensen, 1979	Uncertainty assigned by TRC = 1.5 K; TRC
T_boil	308.87	K	N/A	Dolliver, Gresham, et al., 1938, 2	Uncertainty assigned by TRC = 0.15 K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_fus	157.35	K	N/A	Dolliver, Gresham, et al., 1938, 2	Uncertainty assigned by TRC = 0.3 K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_c	475.	K	N/A	Kobe, Ravicz, et al., 1956	Uncertainty assigned by TRC = 2. K; TRC
Quantity	Value	Units	Method	Reference	Comment
P_c	40.2151	atm	N/A	Kobe, Ravicz, et al., 1956	Uncertainty assigned by TRC = 0.6804 atm; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	6.31	kcal/mol	N/A	Pilcher, Skinner, et al., 1963	DRB
Δ_vapH°	6.35 ± 0.30	kcal/mol	E	Dolliver, Gresham, et al., 1938	Heat of formation derived by Cox and Pilcher, 1970; ALS
Δ_vapH°	6.36	kcal/mol	N/A	Dolliver, Gresham, et al., 1938	DRB

Enthalpy of vaporization

Δ_vapH (kcal/mol)	Temperature (K)	Method	Reference	Comment
7.05	238.	A	Stephenson and Malanowski, 1987	Based on data from 223. to 309. K.; AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Notes

Pilcher, Skinner, et al., 1963
Pilcher, G.; Skinner, H.A.; Pell, A.S.; Pope, A.E., Measurements of heats of combustion by flame calorimetry. Part 1.-Diethyl ether, ethyl vinyl ether and divinyl ether, Trans. Faraday Soc., 1963, 59, 316-330. [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]

Dolliver, Gresham, et al., 1938
Dolliver, M.A.; Gresham, T.L.; Kistiakowsky, G.B.; Smith, E.A.; Vaughan, W.E., Heats of organic reactions. VI. Heats of hydrogenation of some oxygen-containing compounds, J. Am. Chem. Soc., 1938, 60, 440-450. [all data]

Favorskii and Shostakovskii, 1943
Favorskii, A.E.; Shostakovskii, M.F., Vinyl ethers. I. Synthesis and properties of vinyl ethers, Zh. Obshch. Kim., 1943, 13, 1-20. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Farchan Laboratories, 1990
Farchan Laboratories, Research Chemicals Catalog, Farchan Laboratories, Gainesville, FL, 1990, 91. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Owen and Sorensen, 1979
Owen, N.L.; Sorensen, G.O., Microwave spectrum, conformation, and barrier to internal rotation of ethyl vinyl ether, J. Phys. Chem., 1979, 83, 1483. [all data]

Dolliver, Gresham, et al., 1938, 2
Dolliver, M.A.; Gresham, T.L.; Kistiakowsky, G.B.; Smith, E.A.; Vaughan, W.E., Heats of Organic Reactions VI. Heats of Hydrogenation of Some Oxygen- Containing Compounds, J. Am. Chem. Soc., 1938, 60, 440. [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]

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]

Notes

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Symbols used in this document:

P_c	Critical pressure
T_boil	Boiling point
T_c	Critical temperature
T_fus	Fusion (melting) point
Δ_cH°_gas	Enthalpy of combustion of gas at standard conditions
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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