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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- 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.
Condensed phase thermochemistry data
Go To: Top, Phase change data, Henry's Law data, Gas phase ion energetics data, 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:
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 |
Phase change data
Go To: Top, Condensed phase thermochemistry data, Henry's Law data, Gas phase ion energetics data, 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:
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° | 94.4 | kJ/mol | CGC | Roux, Temprado, et al., 2005 | Based on data from 424. to 503. K.; AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 123.1 | kJ/mol | N/A | De Wit, Van Miltenburg, et al., 1983 | AC |
ΔsubH° | 120.3 ± 4.4 | kJ/mol | N/A | Cox and Pilcher, 1970 | See also Davies and Thomas, 1960.; AC |
ΔsubH° | 118. ± 3. | kJ/mol | V | Davies and Thomas, 1960 | ALS |
ΔsubH° | 121.8 ± 3.3 | kJ/mol | N/A | Davies and Thomas, 1960 | See also Ribeiro da Silva, Monte, et al., 1999.; AC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
128. ± 2. | 318. to 358. | TPD | Cappa, Lovejoy, et al., 2007 | AC |
119.5 | 280. to 302. | TPTD | Chattopadhyay and Ziemann, 2005 | AC |
120.5 | 368. | TE,ME | De Wit, Van Miltenburg, et al., 1983 | Based on data from 356. to 376. K.; AC |
118.1 ± 3.3 | 386. | ME | Cox and Pilcher, 1970 | Based on data from 372. to 401. K. See also Davies and Thomas, 1960.; AC |
73.6 | 306. | A | Granovskaya, 1947 | Based on data from 292. to 320. K.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
32.945 | 457.0 | Cingolani and Berchiesi, 1974 | DH |
34. | 455.2 | Roux, Temprado, et al., 2005 | AC |
32.95 | 457. | Acree, 1991 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
72.09 | 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 (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.172 | 272. | crystaline, II | crystaline, I | Parks and Huffman, 1930 | DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.63 | 272. | crystaline, II | crystaline, I | Parks and Huffman, 1930 | DH |
Henry's Law data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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: Rolf Sander
Henry's Law constant (water solution)
kH(T) = k°H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
k°H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)
k°H (mol/(kg*bar)) | d(ln(kH))/d(1/T) (K) | Method | Reference | Comment |
---|---|---|---|---|
3.0×10+8 | E | N/A | Value obtained by missing citation using the group contribution method. |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law data, 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: John E. Bartmess
De-protonation reactions
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 |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1328. ± 8.4 | kJ/mol | CIDC | Kumar, Prabhakar, et al., 2005 | gas phase |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics 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: 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).
Due to licensing restrictions, this spectrum cannot be downloaded.
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. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW-1791 |
NIST MS number | 229614 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, 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.
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]
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]
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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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) Tfus Fusion (melting) point Ttriple Triple point temperature Ttrs Temperature of phase transition d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions 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
- 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.