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:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Henry's Law data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
  • Switch to calorie-based units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, "lite" edition (thermophysical and thermochemical data)
• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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 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

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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 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)

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

Reaction thermochemistry data

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

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering data, References, Notes

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

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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: 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^-

References

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

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]

Norrman and McMahon, 1999
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]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [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]

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

Viidanoja, Reiner, et al., 2000
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]

Butler, Fraser-Monteiro, et al., 1982
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
Holmes, J.L.; Fingas, M.; Lossing, F.P., Towards a general scheme for estimating the heats of formation of organic ions in the gas phase. Part I. Odd-electron cations, Can. J. Chem., 1981, 59, 80. [all data]

Holmes and Lossing, 1980
Holmes, J.L.; Lossing, F.P., Gas-phase heats of formation of keto and enol ions of carbonyl compounds., J. Am. Chem. Soc., 1980, 102, 1591. [all data]

Watanabe, Yokoyama, et al., 1973
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]

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

Benoit and Harrison, 1977
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
Sustmann, R.; Trill, H., Photoelektronenspektroskopische Bestimmung von Substituenten-Effekten. II. α,β-ungesattigte Carbonester, Tetrahedron Lett., 1972, 42, 4271. [all data]

Holmes and Lossing, 1980, 2
Holmes, J.L.; Lossing, F.P., Thermochemistry and unimolecular reactions of ionized acetic acid and its enol in the gas phase., J. Am. Chem. Soc., 1980, 102, 3732. [all data]

Notes

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