Butanoic acid

• Formula: C₄H₈O₂
• Molecular weight: 88.1051
• IUPAC Standard InChI: InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6) Copy

  
• IUPAC Standard InChIKey: FERIUCNNQQJTOY-UHFFFAOYSA-N Copy
• CAS Registry Number: 107-92-6
• 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: Butyric acid; n-Butanoic acid; n-Butyric acid; Ethylacetic acid; Propylformic acid; 1-Butyric acid; 1-Propanecarboxylic acid; n-C3H7COOH; Propanecarboxylic acid; Butanic acid; Buttersaeure; Kyselina maselna; UN 2820; 1-Butanoic acid; NSC 8415
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Henry's Law data
  • IR Spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas 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:
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

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

Constant pressure heat capacity of liquid

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:
BS - Robert L. Brown and Stephen E. Stein
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

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

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:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

C₄H₇O₂^- +  =

By formula: C₄H₇O₂^- + H⁺ = C₄H₈O₂

2 +  =

By formula: 2H₂ + C₄H₄O₂ = C₄H₈O₂

 +  +  = C₄H₁₀NO₆^-

By formula: NO₃^- + H₂O + C₄H₈O₂ = C₄H₁₀NO₆^-

CO₃ +  +  = C₅H₁₀O₆^-

By formula: CO₃ + H₂O + C₄H₈O₂ = C₅H₁₀O₆^-

 +  = C₄H₈NO₅^-

By formula: NO₃^- + C₄H₈O₂ = C₄H₈NO₅^-

 +  = C₄H₈NO₄^-

By formula: NO₂^- + C₄H₈O₂ = C₄H₈NO₄^-

Gas phase ion energetics 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 evaluated as indicated in comments:
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₄H₈O₂⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₄H₇O₂^- +  =

By formula: C₄H₇O₂^- + H⁺ = C₄H₈O₂

Ion clustering 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: John E. Bartmess

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

 +  = C₄H₈NO₄^-

By formula: NO₂^- + C₄H₈O₂ = C₄H₈NO₄^-

 +  = C₄H₈NO₅^-

By formula: NO₃^- + C₄H₈O₂ = C₄H₈NO₅^-

 +  +  = C₄H₁₀NO₆^-

By formula: NO₃^- + H₂O + C₄H₈O₂ = C₄H₁₀NO₆^-

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

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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.

Lebedeva, 1964
Lebedeva, N.D., Heats of combustion of monocarboxylic acids, Russ. J. Phys. Chem. (Engl. Transl.), 1964, 38, 1435-1437. [all data]

Konicek and Wadso, 1970
Konicek, J.; Wadso, I., Enthalpies of vaporization of organic compounds. VII. Some carboxylic acids, Acta Chem. Scand., 1970, 24, 2612-26. [all data]

Stull D.R., 1969
Stull D.R., Jr., The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969. [all data]

Martin and Andon, 1982
Martin, J.F.; Andon, R.J.L., Thermodynamic properties of organic oxygen compounds. Part LII. Molar heat capacity of ethanoic, propanoic, and butanoic acids, J. Chem. Thermodynam., 1982, 14, 679-688. [all data]

Parks, Kelley, et al., 1929
Parks, G.S.; Kelley, K.K.; Huffman, H.M., Thermal data on organic compounds. V. A revision of the entropies and free energies of nineteen organic compounds, J. Am. Chem. Soc., 1929, 51, 1969-1973. [all data]

Parks and Anderson, 1926
Parks, G.S.; Anderson, C.T., Thermal data on organic compounds. III. The heat capacities, entropies and free energies of tertiary butyl alcohol, mannitol, erythritol and normal butyric acid, J. Am. Chem. Soc., 1926, 48, 1506-1512. [all data]

Konicek and Wadso, 1971
Konicek, J.; Wadso, I., Thermochemical properties of some carboxylic acids, amines and N-substituted amides in aqueous solution, Acta Chem. Scand., 1971, 25, 1541-1551. [all data]

von Reis, 1881
von Reis, M.A., Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht, Ann. Physik [3], 1881, 13, 447-464. [all data]

Radwan and Hanna, 1976
Radwan, M.H.; Hanna, A.A., Binary Azeotropes Containing Butyric Acid, J. Chem. Eng. Data, 1976, 21, 285-8. [all data]

Costello and Bowden, 1958
Costello, J.M.; Bowden, S.T., The temperature variation of orthobaric density difference in liquid- vapour systems: IV fatty acids, Recl. Trav. Chim. Pays-Bas, 1958, 77, 803. [all data]

Dreisbach and Martin, 1949
Dreisbach, R.R.; Martin, R.A., Physical Data on Some Organic Compounds, Ind. Eng. Chem., 1949, 41, 2875-8. [all data]

Timmermans, 1935
Timmermans, J., Researches in Stoichiometry. I. The Heat of Fusion of Organic Compounds., Bull. Soc. Chim. Belg., 1935, 44, 17-40. [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]

Martin and Andon, 1982, 2
Martin, J.F.; Andon, R.J.L., Thermodynamic properties of organic oxygen compounds. Part LII. Molar heat capacity of ethanoic, propanoic, and butanoic acids., J. Chem. Thermodyn., 1982, 14, 679-88. [all data]

Parks and Anderson, 1926, 2
Parks, G.S.; Anderson, C.T., Thermal data on organic compounds. III. The heat capacities, entropies and free energies of tertiary butyl alcohol, mannitol, erythritol and normal butyric acid, J. Am. Chem. Soc., 1926, 48, 1506-12. [all data]

Andereya and Chase, 1990
Andereya, E.; Chase, J.D., Chem. Eng. Technol., 1990, 13, 304-12. [all data]

Ambrose and Ghiassee, 1987
Ambrose, D.; Ghiassee, N.B., Vapor Pressures and Critical Temperatures and Critical Pressures of Some Alkanoic Acids: C1 to C10, J. Chem. Thermodyn., 1987, 19, 505. [all data]

D'Souza and Teja, 1987
D'Souza, R.; Teja, A.S., The prediction of the vapor pressures of carboxylic acids, Chem. Eng. Commun., 1987, 61, 13. [all data]

Brown, 1906
Brown, J.C., The critical temperature and value of ml/theta of some carbon compounds, J. Chem. Soc., Trans., 1906, 89, 311. [all data]

Clifford, Ramjugernath, et al., 2004
Clifford, Scott L.; Ramjugernath, Deresh; Raal, J. David, Subatmospheric Vapor Pressure Curves for Propionic Acid, Butyric Acid, Isobutyric Acid, Valeric Acid, Isovaleric Acid, Hexanoic Acid, and Heptanoic Acid, J. Chem. Eng. Data, 2004, 49, 5, 1189-1192, https://doi.org/10.1021/je034180e . [all data]

Muñoz and Krähenbühl, 2001
Muñoz, Laura A.L.; Krähenbühl, M. Alvina, Isobaric Vapor Liquid Equilibrium (VLE) Data of the Systems n -Butanol + Butyric Acid and n -Butanol + Acetic Acid, J. Chem. Eng. Data, 2001, 46, 1, 120-124, https://doi.org/10.1021/je000033u . [all data]

Verevkin, 2000
Verevkin, S.P., Measurement and Prediction of the Monocarboxylic Acids Thermochemical Properties, J. Chem. Eng. Data, 2000, 45, 5, 953-960, https://doi.org/10.1021/je990282m . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Dykyj, 1971
Dykyj, J., Petrochemia, 1971, 11, 2, 27. [all data]

Dreisbach and Shrader, 1949
Dreisbach, R.R.; Shrader, S.A., Vapor Pressure--Temperature Data on Some Organic Compounds, Ind. Eng. Chem., 1949, 41, 12, 2879-2880, https://doi.org/10.1021/ie50480a054 . [all data]

Dreisbach and Martin, 1949, 2
Dreisbach, R.R.; Martin, R.A., Physical Data on Some Organic Compounds, Ind. Eng. Chem., 1949, 41, 12, 2875-2878, https://doi.org/10.1021/ie50480a053 . [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Jasper and Miller, 1955
Jasper, Joseph J.; Miller, George B., The Vapor Pressure of Monofluoroacetic Acid, J. Phys. Chem., 1955, 59, 5, 441-442, https://doi.org/10.1021/j150527a015 . [all data]

Calis-Van Ginkel, Calis, et al., 1978
Calis-Van Ginkel, C.H.D.; Calis, G.H.M.; Timmermans, C.W.M.; de Kruif, C.G.; Oonk, H.A.J., Enthalpies of sublimation and dimerization in the vapour phase of formic, acetic, propanoic, and butanoic acids, The Journal of Chemical Thermodynamics, 1978, 10, 11, 1083-1088, https://doi.org/10.1016/0021-9614(78)90082-4 . [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]

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Norrman, K.; McMahon, T.B., Intramolecular solvation of carboxylate anions in the gas phase, J. Phys. Chem. A, 1999, 103, 35, 7008-7016, https://doi.org/10.1021/jp9908202 . [all data]

Caldwell, Renneboog, et al., 1989
Caldwell, G.; Renneboog, R.; Kebarle, P., Gas Phase Acidities of Aliphatic Carboxylic Acids, Based on Measurements of Proton Transfer Equilibria, Can. J. Chem., 1989, 67, 4, 661, https://doi.org/10.1139/v89-092 . [all data]

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Flitcroft, T.L.; Skinner, H.A., Heats of hydrogenation Part 2.-Acetylene derivatives, Trans. Faraday Soc., 1958, 54, 47-53. [all data]

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Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

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Viidanoja, J.; Reiner, T.; Kiendler, A.; Grimm, F.; Arnold, F., Laboratory investigations of negative ion molecule reactions of propionic, butyric, glyoxylic, pyruvic, and pinonic acids, Int. J. Mass Spectrom., 2000, 194, 1, 53-68, https://doi.org/10.1016/S1387-3806(99)00172-4 . [all data]

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Butler, J.J.; Fraser-Monteiro, M.L.; Fraser-Monteiro, L.; Baer, T.; Hass, J.R., Thermochemistry and dissociation dynamics of state-selected C₄H₈O₂⁺ Ions. 2. Butanoic acid, J. Phys. Chem., 1982, 86, 747. [all data]

Holmes, Fingas, et al., 1981
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Holmes and Lossing, 1980
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Watanabe, I.; Yokoyama, Y.; Ikeda, S., Lone pair ionization potentials of carboxylic acids determined by He(I) photoelectron spectroscopy, Bull. Chem. Soc. Jpn., 1973, 46, 1959. [all data]

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Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

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Benoit, F.M.; Harrison, A.G., Predictive value of proton affinity. Ionization energy correlations involving oxygenated molecules, J. Am. Chem. Soc., 1977, 99, 3980. [all data]

Sustmann and Trill, 1972
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Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,liquid	Constant pressure heat capacity of liquid
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  S°gas	Entropy of gas at standard conditions
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid 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
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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