Ethyl acetoacetate
- Formula: C6H10O3
- Molecular weight: 130.1418
- IUPAC Standard InChI: InChI=1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3
- IUPAC Standard InChIKey: XYIBRDXRRQCHLP-UHFFFAOYSA-N
- CAS Registry Number: 141-97-9
- 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: Butanoic acid, 3-oxo-, ethyl ester; Acetoacetic acid, ethyl ester; Active acetylacetate; Diacetic ether; Ethyl acetylacetate; Ethyl 3-oxobutanoate; Ethyl 3-oxobutyrate; EAA; Acetoctan ethylnaty; Ethylacetacetat; Ethylester kyseliny acetoctove; 3-Oxobutanoic acid ethyl ester; 1-Ethoxybutane-1,3-dione; NSC 8657
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, 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
DRB - Donald R. Burgess, Jr.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -586.2 ± 1.5 | kJ/mol | Ccb | Ribeiro da Silva, Ferrao, et al., 1995 | ALS |
| ΔfH°gas | -558.0 | kJ/mol | N/A | Vilcu and Perisanu, 1979 | Value computed using ΔfHliquid° value of -612.2±5.4 kj/mol from Vilcu and Perisanu, 1979 and ΔvapH° value of 54.2 kj/mol from Ribeiro da Silva, Ferrao, et al., 1995.; DRB |
| ΔfH°gas | -507.5 | kJ/mol | N/A | Vilcu, Perisanu, et al., 1975 | Value computed using ΔfHliquid° value of -561.7 kj/mol from Vilcu, Perisanu, et al., 1975 and ΔvapH° value of 54.2 kj/mol from Ribeiro da Silva, Ferrao, et al., 1995.; DRB |
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 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 | -640.4 ± 1.1 | kJ/mol | Ccb | Ribeiro da Silva, Ferrao, et al., 1995 | ALS |
| ΔfH°liquid | -612.2 ± 5.4 | kJ/mol | Ccb | Vilcu and Perisanu, 1979 | ALS |
| ΔfH°liquid | -561.70 | kJ/mol | Ccb | Vilcu, Perisanu, et al., 1975 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -3149.76 ± 0.76 | kJ/mol | Ccb | Ribeiro da Silva, Ferrao, et al., 1995 | Corresponding ΔfHºliquid = -640.45 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -3178.1 ± 7.7 | kJ/mol | Ccb | Vilcu and Perisanu, 1979 | Corresponding ΔfHºliquid = -612.08 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -3153. | kJ/mol | Ccb | Guinchant, 1918 | Corresponding ΔfHºliquid = -637.2 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
| Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 250.2 | 297.5 | Kolosovskii and Udovenko, 1934 | DH |
| 246.9 | 297.5 | de Kolossowsky and Udowenko, 1933 | DH |
| 241.8 | 298. | von Reis, 1881 | T = 288 to 455 K.; DH |
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, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 454. ± 2. | K | AVG | N/A | Average of 10 values; Individual data points |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 54.18 ± 0.96 | kJ/mol | C | Ribeiro da Silva, Ferrao, et al., 1995 | ALS |
| ΔvapH° | 54.2 | kJ/mol | N/A | Ribeiro da Silva, Ferrao, et al., 1995 | DRB |
| ΔvapH° | 54.2 ± 1.0 | kJ/mol | C | Ribeiro da Silva, Ferrao, et al., 1995 | AC |
| ΔvapH° | 50.54 | kJ/mol | V | Vilcu, Perisanu, et al., 1975 | ALS |
Reduced pressure boiling point
| Tboil (K) | Pressure (bar) | Reference | Comment |
|---|---|---|---|
| 347.2 | 0.019 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 52.5 | 316. | A | Stephenson and Malanowski, 1987 | Based on data from 301. to 454. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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| Temperature (K) | A | B | C | Reference | Comment |
|---|---|---|---|---|---|
| 301.7 to 454.0 | 5.16327 | 2189.547 | -29.184 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
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: C2H6O + C4H4O2 = C6H10O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -127.0 | kJ/mol | Kin | Lopatin, Popov, et al., 1992 | liquid phase; solvent: Solution |
=
By formula: C6H10O3 = C6H10O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -13.3 ± 1.0 | kJ/mol | Eqk | Folkendt, Weiss-Lopez, et al., 1985 | gas phase; NMR |
References
Go To: Top, Gas phase thermochemistry data, 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.
Ribeiro da Silva, Ferrao, et al., 1995
Ribeiro da Silva, M.A.V.; Ferrao, M.L.C.C.H.; Jiye, F.,
Standard molar enthalpy of formation and of vaporization of ethyl 3-oxobutanoate,
J. Chem. Eng. Data, 1995, 40, 426-428. [all data]
Vilcu and Perisanu, 1979
Vilcu, R.; Perisanu, S.,
The standard enthalpies of formation of some C, H, O containing compounds,
Rev. Roum. Chim., 1979, 24, 237-243. [all data]
Vilcu, Perisanu, et al., 1975
Vilcu, R.; Perisanu, S.; Ciocazanu, I.,
Heats of formation in the ideal gas state of some substances containing carbon, hydrogen and oxygen,
Conf. Int. Thermodyn. Chim. C.R. 4th, 1975, 1, 105-112. [all data]
Guinchant, 1918
Guinchant, M.J.,
Etude sur la fonction acide dans les derives metheniques et methiniques,
Ann. Chem., 1918, 10, 30-84. [all data]
Kolosovskii and Udovenko, 1934
Kolosovskii, N.A.; Udovenko, W.W.,
Specific heat of liquids. II.,
Zhur. Obshchei Khim., 1934, 4, 1027-1033. [all data]
de Kolossowsky and Udowenko, 1933
de Kolossowsky, N.A.; Udowenko, W.W.,
Mesure des chaleurs specifique moleculaires de quelques liquides,
Compt. rend., 1933, 197, 519-520. [all data]
von Reis, 1881
von Reis, M.A.,
Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht,
Ann. Physik [3], 1881, 13, 447-464. [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]
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]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Lopatin, Popov, et al., 1992
Lopatin, E.B.; Popov, V.V.; Epshtein, N.A.; Mikhaleva, L.M.; Makarov, Yu.N.,
Kinetic and thermochemical characteristics of diketene-based reactions,
Khim.-Farm. Zh., 1992, 26, 76-78. [all data]
Folkendt, Weiss-Lopez, et al., 1985
Folkendt, M.M.; Weiss-Lopez, B.E.; Chauvel, J.P., Jr.; True, N.S.,
Gas-phase 1H NMR studies of keto-enol tautomerism of acetylacetone, methyl acetoacetate, and ethyl acetoacetate,
J. Phys. Chem., 1985, 89, 3347-3352. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Tboil Boiling point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions 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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