Butanedioic acid
- Formula: C4H6O4
- Molecular weight: 118.0880
- IUPAC Standard InChI: InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)
- IUPAC Standard InChIKey: KDYFGRWQOYBRFD-UHFFFAOYSA-N
- CAS Registry Number: 110-15-6
- 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: Succinic acid; Amber acid; Asuccin; Bernsteinsaure; Dihydrofumaric acid; Katasuccin; Wormwood acid; 1,2-Ethanedicarboxylic acid; Ethanedicarboxylic acid; Wormwood; Kyselina jantarova; Acid of amber; Ethylene succinic acid; Sal succini; Salt of amber; Succinellite; 1,4-Butanedioic acid; NSC 106449
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Condensed phase thermochemistry data
Go To: Top, 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°solid | -940. ± 2. | kJ/mol | AVG | N/A | Average of 7 values; Individual data points |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -1491. ± 3. | kJ/mol | AVG | N/A | Average of 16 values; Individual data points |
| Quantity | Value | Units | Method | Reference | Comment |
| S°solid,1 bar | 167.32 | J/mol*K | N/A | Vanderzee and Westrum, 1970 | DH |
| S°solid,1 bar | 175.7 | J/mol*K | N/A | Parks and Huffman, 1930 | crystaline, I phase; Extrapolation below 90 K, 55.10 J/mol*K.; DH |
Constant pressure heat capacity of solid
| Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 152.93 | 298.15 | Vanderzee and Westrum, 1970 | T = 5 to 328 K.; DH |
| 164.0 | 323. | Satoh and Sogabe, 1939 | T = 0 to 100°C. Mean value.; DH |
| 149.8 | 289.8 | Parks and Huffman, 1930 | crystaline, I phase; T = 93 to 290 K. Value is unsmoothed experimental datum.; DH |
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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
B - John E. Bartmess
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: C4H4O4 + H2 = C4H6O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -151.8 ± 0.8 | kJ/mol | Chyd | Skinner and Snelson, 1959 | liquid phase; solvent: Ethanol; ALS |
| ΔrH° | -153.2 ± 1.7 | kJ/mol | Chyd | Flitcroft, Skinner, et al., 1957 | liquid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -152. ± 2. kJ/mol; ALS |
C4H5O4- + =
By formula: C4H5O4- + H+ = C4H6O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1350. ± 8.4 | kJ/mol | CIDC | Kumar, Prabhakar, et al., 2005 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1328. ± 8.4 | kJ/mol | CIDC | Kumar, Prabhakar, et al., 2005 | gas phase; B |
+
=
By formula: C4H4O3 + H2O = C4H6O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -46.86 ± 0.08 | kJ/mol | Cm | Conn, Kistiakowsky, et al., 1942 | liquid phase; Heat of hydrolysis at 303 K; ALS |
+
=
By formula: C4H4O4 + H2 = C4H6O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -130.3 ± 0.1 | kJ/mol | Chyd | Flitcroft, Skinner, et al., 1957 | liquid phase; ALS |
2 +
=
By formula: 2H2 + C4H2O4 = C4H6O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -363.2 ± 4.6 | kJ/mol | Chyd | Flitcroft and Skinner, 1958 | solid phase; ALS |
References
Go To: Top, Condensed phase thermochemistry 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.
Vanderzee and Westrum, 1970
Vanderzee, C.E.; Westrum, E.F., Jr.,
Succinic acid. Heat capacities and thermodynamic properties from 5 to 328K. An efficient drying procedure,
J. Chem. Thermodynam., 1970, 2, 681-687. [all data]
Parks and Huffman, 1930
Parks, G.S.; Huffman, H.M.,
Thermal data on organic compounds. IX. A study of the effect of unsaturation on the heat capacities, entropies and free energies of some hydrocarbons and other compounds,
J. Am. Chem. Soc., 1930, 52, 4381-4391. [all data]
Satoh and Sogabe, 1939
Satoh, S.; Sogabe, T.,
The specific heats of some solid aliphatic acids and their ammonium salts and the atomic heat of nitrogen,
Sci. Pap. Inst. Phys. Chem. Res. (Tokyo), 1939, 36, 97-105. [all data]
Skinner and Snelson, 1959
Skinner, H.A.; Snelson, A.,
Heats of hydrogenation Part 3.,
Trans. Faraday Soc., 1959, 55, 405-407. [all data]
Flitcroft, Skinner, et al., 1957
Flitcroft, T.; Skinner, H.A.; Whiting, M.C.,
Heats of hydrogenation Part 1.-Dodeca-3:9 and -5:7 Diynes,
Trans. Faraday Soc., 1957, 53, 784-790. [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]
Kumar, Prabhakar, et al., 2005
Kumar, M.R.; Prabhakar, S.; Nagaveni, V.; Vairamani, M.,
Estimation of gas-phase acidities of a series of dicarboxylic acids by the kinetic method,
Rapid Commun. Mass Spectrom., 2005, 19, 8, 1053-1057, https://doi.org/10.1002/rcm.1888
. [all data]
Conn, Kistiakowsky, et al., 1942
Conn, J.B.; Kistiakowsky, G.B.; Roberts, R.M.; Smith, E.A.,
Heats of organic reactions. XIII. Heats of hydrolysis of some acid anhydrides,
J. Am. Chem. Soc., 1942, 64, 1747-17. [all data]
Flitcroft and Skinner, 1958
Flitcroft, T.L.; Skinner, H.A.,
Heats of hydrogenation Part 2.-Acetylene derivatives,
Trans. Faraday Soc., 1958, 54, 47-53. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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