Butanedioic acid
- Formula: C4H6O4
- Molecular weight: 118.0880
- 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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Phase change data
Go To: Top, 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
AC - William E. Acree, Jr., James S. Chickos
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 |
---|---|---|---|---|---|
Tfus | 459. ± 3. | K | AVG | N/A | Average of 12 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 461. | K | N/A | Wilhoit, Chao, et al., 1985 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 22.6 | kcal/mol | CGC | Roux, Temprado, et al., 2005 | Based on data from 424. to 503. K.; AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 29.42 | kcal/mol | N/A | De Wit, Van Miltenburg, et al., 1983 | AC |
ΔsubH° | 28.8 ± 1.1 | kcal/mol | N/A | Cox and Pilcher, 1970 | See also Davies and Thomas, 1960.; AC |
ΔsubH° | 28.1 ± 0.8 | kcal/mol | V | Davies and Thomas, 1960 | ALS |
ΔsubH° | 29.11 ± 0.79 | kcal/mol | N/A | Davies and Thomas, 1960 | See also Ribeiro da Silva, Monte, et al., 1999.; AC |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
30.6 ± 0.5 | 318. to 358. | TPD | Cappa, Lovejoy, et al., 2007 | AC |
28.56 | 280. to 302. | TPTD | Chattopadhyay and Ziemann, 2005 | AC |
28.80 | 368. | TE,ME | De Wit, Van Miltenburg, et al., 1983 | Based on data from 356. to 376. K.; AC |
28.23 ± 0.79 | 386. | ME | Cox and Pilcher, 1970 | Based on data from 372. to 401. K. See also Davies and Thomas, 1960.; AC |
17.6 | 306. | A | Granovskaya, 1947 | Based on data from 292. to 320. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
7.8740 | 457.0 | Cingolani and Berchiesi, 1974 | DH |
8.1 | 455.2 | Roux, Temprado, et al., 2005 | AC |
7.875 | 457. | Acree, 1991 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
17.23 | 457.0 | Cingolani and Berchiesi, 1974 | DH |
Temperature of phase transition
Ttrs (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|
389.7 | crystaline, II | crystaline, I | Petropavlov, Tsygankova, et al., 1988 | DH |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.0411 | 272. | crystaline, II | crystaline, I | Parks and Huffman, 1930 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.15 | 272. | crystaline, II | crystaline, I | Parks and Huffman, 1930 | DH |
References
Go To: Top, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Wilhoit, Chao, et al., 1985
Wilhoit, R.C.; Chao, J.; Hall, K.R.,
Thermodynamic Properties of Key Organic Compounds in the Carbon Range C1 to C4. Part 1. Properties of Condensed Phases,
J. Phys. Chem. Ref. Data, 1985, 14, 1. [all data]
Roux, Temprado, et al., 2005
Roux, Maria Victoria; Temprado, Manuel; Chickos, James S.,
Vaporization, fusion and sublimation enthalpies of the dicarboxylic acids from C4 to C14 and C16,
The Journal of Chemical Thermodynamics, 2005, 37, 9, 941-953, https://doi.org/10.1016/j.jct.2004.12.011
. [all data]
De Wit, Van Miltenburg, et al., 1983
De Wit, H.G.M.; Van Miltenburg, J.C.; De Kruif, C.G.,
Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen, and sulphur 1. Vapour pressures and enthalpies of sublimation,
The Journal of Chemical Thermodynamics, 1983, 15, 7, 651-663, https://doi.org/10.1016/0021-9614(83)90079-4
. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]
Davies and Thomas, 1960
Davies, M.; Thomas, G.H.,
The lattice energies, infra-red spectra, and possible cyclization of some dicarboxylic acids,
Trans. Faraday Soc., 1960, 56, 185. [all data]
Ribeiro da Silva, Monte, et al., 1999
Ribeiro da Silva, Manuel A.V.; Monte, Manuel J.S.; Ribeiro, José R.,
Vapour pressures and the enthalpies and entropies of sublimation of five dicarboxylic acids,
The Journal of Chemical Thermodynamics, 1999, 31, 8, 1093-1107, https://doi.org/10.1006/jcht.1999.0522
. [all data]
Cappa, Lovejoy, et al., 2007
Cappa, Christopher D.; Lovejoy, Edward R.; Ravishankara, A.R.,
Determination of Evaporation Rates and Vapor Pressures of Very Low Volatility Compounds: A Study of the C 4 -C 10 and C 12 Dicarboxylic Acids,
J. Phys. Chem. A, 2007, 111, 16, 3099-3109, https://doi.org/10.1021/jp068686q
. [all data]
Chattopadhyay and Ziemann, 2005
Chattopadhyay, Sulekha; Ziemann, Paul J.,
Vapor Pressures of Substituted and Unsubstituted Monocarboxylic and Dicarboxylic Acids Measured Using an Improved Thermal Desorption Particle Beam Mass Spectrometry Method,
Aerosol Science and Technology, 2005, 39, 11, 1085-1100, https://doi.org/10.1080/02786820500421547
. [all data]
Granovskaya, 1947
Granovskaya, A.,
Russ. J. Phys. Chem., 1947, 21, 967. [all data]
Cingolani and Berchiesi, 1974
Cingolani, A.; Berchiesi, G.,
Thermodynamic properties of organic compounds. 1. A DSC study of phase transitions in aliphatic dicarboxylic acids,
J. Therm. Anal., 1974, 6, 87-90. [all data]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [all data]
Petropavlov, Tsygankova, et al., 1988
Petropavlov, N.N.; Tsygankova, I.G.; Teslenko, L.A.,
Microcalorimetric investigation of polymorphic transitions in organic crystals,
Sov. Phys. Crystallogr., 1988, 33(6), 853-855. [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]
Notes
Go To: Top, Phase change data, References
- Symbols used in this document:
Tfus Fusion (melting) point Ttriple Triple point temperature Ttrs Temperature of phase transition ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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