Acetic acid ethenyl ester
- Formula: C4H6O2
- Molecular weight: 86.0892
- IUPAC Standard InChIKey: XTXRWKRVRITETP-UHFFFAOYSA-N
- CAS Registry Number: 108-05-4
- 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: Acetic acid vinyl ester; Vinyl acetate; Vinyl A monomer; VyAc; 1-Acetoxyethylene; CH3CO2CH=CH2; Ethenyl acetate; Ethenyl ethanoate; Acetate de vinyle; Ethanoic acid, ethenyl ester; Octan winylu; Vinile (acetato di); Vinyl acetate h.q.; Vinyl ethanoate; Vinylacetaat; Vinylacetat; Vinyle (acetate de); Zeset T; Acetic acid, ethylene ether; VAC; Vinylester kyseliny octove; Vinyl ester of acetic acid; Everflex 81L; Plyamul 40305-00; Unocal 76 Res 6206; Unocal 76 Res S-55; Vinnapas A 50; Vinyl acetate monomer; Acetoxyethene; NSC 8404
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Condensed phase thermochemistry data
Go To: Top, Phase change 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 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 | -83.84 | kcal/mol | Chyd | Vilcu and Perisanu, 1980 | ALS |
ΔfH°liquid | -82.7 ± 2.5 | kcal/mol | Ccb | Vilcu and Perisanu, 1980 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -498.5 ± 2.5 | kcal/mol | Ccb | Vilcu and Perisanu, 1980 | Corresponding ΔfHºliquid = -82.66 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
40.51 | 298. | Bengough and Thomson, 1959 | Mean value 23 to 50°C.; DH |
Phase change 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 compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
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 | 345.7 ± 0.6 | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 172.95 | K | N/A | Dolliver, Gresham, et al., 1938 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 519.13 | K | N/A | Daubert, Jalowka, et al., 1987 | Uncertainty assigned by TRC = 0.4 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 41.30 | atm | N/A | Daubert, Jalowka, et al., 1987 | Uncertainty assigned by TRC = 0.09 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 8.88 ± 0.20 | kcal/mol | V | Vilcu and Perisanu, 1980 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
8.22 | 309. | A | Stephenson and Malanowski, 1987 | Based on data from 294. to 346. K. See also Dykyj, 1971, Capková and Fried, 1963, and Boublik, Fried, et al., 1984.; AC |
7.50 | 348. | N/A | Swamy and Van Winkle, 1965 | Based on data from 340. to 355. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
340. to 355. | 5.22270 | 1807.332 | 0.726 | Swamy and Van Winkle, 1965 | Coefficents calculated by NIST from author's data. |
294.98 to 345.19 | 4.33461 | 1299.069 | -46.183 | Capková and Fried, 1963 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.02 | 180.6 | Kulagina and Lebedev, 1997 | AC |
Reaction thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change 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: C4H6O2 + H2 = C4H8O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -30.9 ± 1.1 | kcal/mol | Chyd | Vilcu and Perisanu, 1980 | liquid phase |
ΔrH° | -31.12 ± 0.06 | kcal/mol | Chyd | Dolliver, Gresham, et al., 1938, 2 | gas phase; At 355 °K |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Vilcu and Perisanu, 1980
Vilcu, R.; Perisanu, S.,
The ideal gas state enthalpies of formation of some monomers,
Rev. Roum. Chim., 1980, 25, 619-624. [all data]
Bengough and Thomson, 1959
Bengough, W.I.; Thomson, R.A.M.,
A dilatometric method of measuring the heats of radiation-induced reactions. Part 2.- The heat of photochemical addition of bromotrichloromethane to vinyl acetate,
Trans. Faraday Soc., 1959, 55, 268-271. [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. [all data]
Daubert, Jalowka, et al., 1987
Daubert, T.E.; Jalowka, J.W.; Goren, V.,
Vapor pressure of 22 pure industrial chemicals,
AIChE Symp. Ser., 1987, 83, 256, 128-156. [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]
Dykyj, 1971
Dykyj, J.,
Petrochemia, 1971, 11, 2, 27. [all data]
Capková and Fried, 1963
Capková, A.; Fried, V.,
Gleichgewicht flüssigkeit-dampf XXX. System vinylacetat-essigsäure,
Collect. Czech. Chem. Commun., 1963, 28, 8, 2235-2239, https://doi.org/10.1135/cccc19632235
. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Swamy and Van Winkle, 1965
Swamy, P.A.; Van Winkle, Matthew,
Vapor-Liquid Equilibria at 760 Mm. Mercury for the System Vinyl Acetate-2,4-Dimethyl Pentane.,
J. Chem. Eng. Data, 1965, 10, 3, 214-215, https://doi.org/10.1021/je60026a002
. [all data]
Kulagina and Lebedev, 1997
Kulagina, T.G.; Lebedev, B.V.,
Thermodynamic properties of vinyl acetate at 0-330 K,
Zh. Fiz. Khim., 1997, 71, 4, 601. [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, 440-450. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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