Butanedioic acid

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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
Δfsolid-224.7 ± 0.4kcal/molAVGN/AAverage of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Δcsolid-356.4 ± 0.8kcal/molAVGN/AAverage of 16 values; Individual data points
Quantity Value Units Method Reference Comment
solid,1 bar39.990cal/mol*KN/AVanderzee and Westrum, 1970DH
solid,1 bar41.99cal/mol*KN/AParks and Huffman, 1930crystaline, I phase; Extrapolation below 90 K, 55.10 J/mol*K.; DH

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
36.551298.15Vanderzee and Westrum, 1970T = 5 to 328 K.; DH
39.20323.Satoh and Sogabe, 1939T = 0 to 100°C. Mean value.; DH
35.80289.8Parks and Huffman, 1930crystaline, 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

Maleic acid + Hydrogen = Butanedioic acid

By formula: C4H4O4 + H2 = C4H6O4

Quantity Value Units Method Reference Comment
Δr-36.3 ± 0.2kcal/molChydSkinner and Snelson, 1959liquid phase; solvent: Ethanol; ALS
Δr-36.61 ± 0.40kcal/molChydFlitcroft, Skinner, et al., 1957liquid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -36.4 ± 0.4 kcal/mol; ALS

C4H5O4- + Hydrogen cation = Butanedioic acid

By formula: C4H5O4- + H+ = C4H6O4

Quantity Value Units Method Reference Comment
Δr322.6 ± 2.0kcal/molCIDCKumar, Prabhakar, et al., 2005gas phase; B
Quantity Value Units Method Reference Comment
Δr317.3 ± 2.0kcal/molCIDCKumar, Prabhakar, et al., 2005gas phase; B

Succinic anhydride + Water = Butanedioic acid

By formula: C4H4O3 + H2O = C4H6O4

Quantity Value Units Method Reference Comment
Δr-11.20 ± 0.02kcal/molCmConn, Kistiakowsky, et al., 1942liquid phase; Heat of hydrolysis at 303 K; ALS

Fumaric Acid + Hydrogen = Butanedioic acid

By formula: C4H4O4 + H2 = C4H6O4

Quantity Value Units Method Reference Comment
Δr-31.15 ± 0.03kcal/molChydFlitcroft, Skinner, et al., 1957liquid phase; ALS

2Hydrogen + 2-Butynedioic acid = Butanedioic acid

By formula: 2H2 + C4H2O4 = C4H6O4

Quantity Value Units Method Reference Comment
Δr-86.8 ± 1.1kcal/molChydFlitcroft and Skinner, 1958solid phase; ALS

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 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)

H (mol/(kg*bar)) d(ln(kH))/d(1/T) (K) Method Reference Comment
3.0×10+8 EN/AValue obtained by missing citation using the group contribution method.

References

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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

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