Ethene, ethoxy-

• Formula: C₄H₈O
• Molecular weight: 72.1057
• IUPAC Standard InChI:
  

  InChI=1S/C4H8O/c1-3-5-4-2/h3H,1,4H2,2H3 Download the identifier in a file.

• 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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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas phase ion energetics data
  • Gas Chromatography
• Data at other public NIST sites:
  • Computational Chemistry Comparison and Benchmark Database
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 4.1
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Gas 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
fH°gas	-33.50 ± 0.23	kcal/mol	Cm	Pilcher, Skinner, et al., 1963
fH°gas	-33.48 ± 0.23	kcal/mol	Ccb	Pilcher, Skinner, et al., 1963	Heat of formation derived by Cox and Pilcher, 1970
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
cH°gas	-615.98 ± 0.22	kcal/mol	Cm	Pilcher, Skinner, et al., 1963	Corresponding «DELTA»fHºgas = -33.48 kcal/mol (simple calculation by NIST; no Washburn corrections)

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

Quantity	Value	Units	Method	Reference	Comment
fH°liquid	-39.83 ± 0.39	kcal/mol	Ccb	Pilcher, Skinner, et al., 1963	Heat of formation derived by Cox and Pilcher, 1970
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
cH°liquid	-607.0 ± 2.5	kcal/mol	Ccb	Favorskii and Shostakovskii, 1943	Corresponding «DELTA»fHºliquid = -42.5 kcal/mol (simple calculation by NIST; no Washburn corrections)

Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Kenneth Kroenlein 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
Tboil	308. ± 2.	K	AVG	N/A	Average of 6 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
Tfus	157.85	K	N/A	Anonymous, 1968	TRC
Tfus	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
Tc	475.	K	N/A	Kobe, Ravicz, et al., 1956	Uncertainty assigned by TRC = 2. K; TRC
Quantity	Value	Units	Method	Reference	Comment
Pc	40.2151	atm	N/A	Kobe, Ravicz, et al., 1956	Uncertainty assigned by TRC = 0.6804 atm; TRC
Quantity	Value	Units	Method	Reference	Comment
vapH°	6.31	kcal/mol	N/A	Pilcher, Skinner, et al., 1963	DRB
vapH°	6.35 ± 0.30	kcal/mol	E	Dolliver, Gresham, et al., 1938	Heat of formation derived by Cox and Pilcher, 1970; ALS
vapH°	6.36	kcal/mol	N/A	Dolliver, Gresham, et al., 1938	DRB

Enthalpy of vaporization

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

Reaction 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 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: C₄H₈O + H₂ = C₄H₁₀O

Quantity	Value	Units	Method	Reference	Comment
rH°	-26.50 ± 0.14	kcal/mol	Chyd	Allinger, Glaser, et al., 1981	liquid phase; solvent: Hexane
rH°	-26.48 ± 0.06	kcal/mol	Chyd	Dolliver, Gresham, et al., 1938	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -26.7 ± 0.6 kcal/mol; At 355°K

=  + 

By formula: C₄H₉ClO = C₄H₈O + HCl

Quantity	Value	Units	Method	Reference	Comment
rH°	16.30 ± 0.50	kcal/mol	Eqk	Failes and Stimson, 1967	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = 16.5 kcal/mol; At 450 K

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLUTION (10% IN CCl4 FOR 4000-1340 CM^-1, 10% IN CS2 FOR 1340-600 CM^-1); BECKMAN IR-7 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas

Mass spectrum (electron ionization)

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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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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.

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]

Anonymous, 1968
Anonymous, X., Chemicals and Plastics Physical Properties, 1968, Union Carbide Corp., product bulletin, 1968. [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]

Allinger, Glaser, et al., 1981
Allinger, N.L.; Glaser, J.A.; Davis, H.E., Heats of hydrogenation of some vinyl ethers and related compounds, J. Org. Chem., 1981, 46, 658-661. [all data]

Failes and Stimson, 1967
Failes, R.L.; Stimson, V.R., The thermal decomposition of 1-ethoxyethyl chloride and the reverse combination, Aust. J. Chem., 1967, 20, 1553-1560. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  cH°gas	Enthalpy of combustion of gas at standard conditions
  cH°liquid	Enthalpy of combustion of liquid at standard conditions
  fH°gas	Enthalpy of formation of gas at standard conditions
  fH°liquid	Enthalpy of formation of liquid at standard conditions
  rH°	Enthalpy of reaction at standard conditions
  vapH	Enthalpy of vaporization
  vapH°	Enthalpy of vaporization at standard conditions

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