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-940. ± 2.kJ/molAVGN/AAverage of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Δcsolid-1491. ± 3.kJ/molAVGN/AAverage of 16 values; Individual data points
Quantity Value Units Method Reference Comment
solid,1 bar167.32J/mol*KN/AVanderzee and Westrum, 1970DH
solid,1 bar175.7J/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 (J/mol*K) Temperature (K) Reference Comment
152.93298.15Vanderzee and Westrum, 1970T = 5 to 328 K.; DH
164.0323.Satoh and Sogabe, 1939T = 0 to 100°C. Mean value.; DH
149.8289.8Parks and Huffman, 1930crystaline, I phase; T = 93 to 290 K. Value is unsmoothed experimental datum.; 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:
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
Tfus459. ± 3.KAVGN/AAverage of 12 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple461.KN/AWilhoit, Chao, et al., 1985Crystal phase 1 phase; Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Δvap94.4kJ/molCGCRoux, Temprado, et al., 2005Based on data from 424. - 503. K.; AC
Quantity Value Units Method Reference Comment
Δsub123.1kJ/molN/ADe Wit, Van Miltenburg, et al., 1983AC
Δsub120.3 ± 4.4kJ/molN/ACox and Pilcher, 1970See also Davies and Thomas, 1960.; AC
Δsub118. ± 3.kJ/molVDavies and Thomas, 1960ALS
Δsub121.8 ± 3.3kJ/molN/ADavies and Thomas, 1960See also Ribeiro da Silva, Monte, et al., 1999.; AC

Enthalpy of sublimation

ΔsubH (kJ/mol) Temperature (K) Method Reference Comment
128. ± 2.318. - 358.TPDCappa, Lovejoy, et al., 2007AC
119.5280. - 302.TPTDChattopadhyay and Ziemann, 2005AC
120.5368.TE,MEDe Wit, Van Miltenburg, et al., 1983Based on data from 356. - 376. K.; AC
118.1 ± 3.3386.MECox and Pilcher, 1970Based on data from 372. - 401. K. See also Davies and Thomas, 1960.; AC
73.6306.AGranovskaya, 1947Based on data from 292. - 320. K.; AC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
32.945457.0Cingolani and Berchiesi, 1974DH
34.455.2Roux, Temprado, et al., 2005AC
32.95457.Acree, 1991AC

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
72.09457.0Cingolani and Berchiesi, 1974DH

Temperature of phase transition

Ttrs (K) Initial Phase Final Phase Reference Comment
389.7crystaline, IIcrystaline, IPetropavlov, Tsygankova, et al., 1988DH

Enthalpy of phase transition

ΔHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.172272.crystaline, IIcrystaline, IParks and Huffman, 1930DH

Entropy of phase transition

ΔStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
0.63272.crystaline, IIcrystaline, IParks and Huffman, 1930DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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-151.8 ± 0.8kJ/molChydSkinner and Snelson, 1959liquid phase; solvent: Ethanol; ALS
Δr-153.2 ± 1.7kJ/molChydFlitcroft, Skinner, et al., 1957liquid phase; Reanalyzed by Cox and Pilcher, 1970, 2, Original value = -152. ± 2. kJ/mol; ALS

C4H5O4- + Hydrogen cation = Butanedioic acid

By formula: C4H5O4- + H+ = C4H6O4

Quantity Value Units Method Reference Comment
Δr1350. ± 8.4kJ/molCIDCKumar, Prabhakar, et al., 2005gas phase; B
Quantity Value Units Method Reference Comment
Δr1328. ± 8.4kJ/molCIDCKumar, Prabhakar, et al., 2005gas phase; B

Succinic anhydride + Water = Butanedioic acid

By formula: C4H4O3 + H2O = C4H6O4

Quantity Value Units Method Reference Comment
Δr-46.86 ± 0.08kJ/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-130.3 ± 0.1kJ/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-363.2 ± 4.6kJ/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.

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, IR Spectrum, 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- + Hydrogen cation = Butanedioic acid

By formula: C4H5O4- + H+ = C4H6O4

Quantity Value Units Method Reference Comment
Δr1350. ± 8.4kJ/molCIDCKumar, Prabhakar, et al., 2005gas phase
Quantity Value Units Method Reference Comment
Δr1328. ± 8.4kJ/molCIDCKumar, Prabhakar, et al., 2005gas phase

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

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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

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References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, 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]

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, 2
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, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References