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
- 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.
Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | -33.50 ± 0.23 | kcal/mol | Cm | Pilcher, Skinner, et al., 1963 | |
![]() | -33.48 ± 0.23 | kcal/mol | Ccb | Pilcher, Skinner, et al., 1963 | Heat of formation derived by Cox and Pilcher, 1970 |
![]() | -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 |
![]() | -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
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | -39.83 ± 0.39 | kcal/mol | Ccb | Pilcher, Skinner, et al., 1963 | Heat of formation derived by Cox and Pilcher, 1970 |
![]() | -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 |
![]() | -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
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, 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:
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 |
![]() | 6.31 | kcal/mol | N/A | Pilcher, Skinner, et al., 1963 | DRB |
![]() | 6.35 ± 0.30 | kcal/mol | E | Dolliver, Gresham, et al., 1938 | Heat of formation derived by Cox and Pilcher, 1970; ALS |
![]() | 6.36 | kcal/mol | N/A | Dolliver, Gresham, et al., 1938 | DRB |
Enthalpy of vaporization
![]() |
Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
7.05 | 238. | A | Stephenson and Malanowski, 1987 | Based on data from 223. - 309. K.; AC |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, 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 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 |
---|---|---|---|---|---|
![]() | -26.50 ± 0.14 | kcal/mol | Chyd | Allinger, Glaser, et al., 1981 | liquid phase; solvent: Hexane |
![]() | -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 |
---|---|---|---|---|---|
![]() | 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
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes
Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
View spectrum image in SVG format.
Download spectrum in JCAMP-DX format.
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 | 293 |
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
- 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.