Butyrolactone

• Formula: C₄H₆O₂
• Molecular weight: 86.0892
• IUPAC Standard InChI: InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2 Copy

  
• IUPAC Standard InChIKey: YEJRWHAVMIAJKC-UHFFFAOYSA-N Copy
• CAS Registry Number: 96-48-0
• 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.
• Species with the same structure:
  • Oxolan-2-one
• Other names: 2(3H)-Furanone, dihydro-; γ-Butyrolactone; γ-BL; γ-Hydroxybutyric acid cyclic ester; γ-Hydroxybutyric acid lactone; γ-Hydroxybutyrolactone; Butanoic acid, 4-hydroxy-, γ-lactone; Butyric acid lactone; Butyryl lactone; Dihydro-2(3H)-furanone; Tetrahydro-2-furanone; 1,4-Butanolide; 4-Butanolide; 4-Butyrolactone; 4-Deoxytetronic acid; 4-Hydroxybutanoic acid lactone; 4-Hydroxybutyric acid lactone; 6480; 1,4-Butyrolactone; γ-6480; Butyric acid, 4-hydroxy-, γ-lactone; Butyrylactone; BLO; BLON; Dihydro-2-furanone; NCI-C55878; 1,2-Butanolide; 4-Hydroxybutanoic acid, γ-lactone; 4-Hydroxybutyric acid, γ-lactone; 2-Oxolanone; 1-Oxacyclopentan-2-one; 2-Oxotetrahydrofuran; γ-Butanolactone; γ-Hydrooxybutyric acid lactone; Agrisynth BLO; GBL; Butyric acid, 4-hydroxy-, gamma-lactone; 2(3H)-dihydrofuranone; Dihydro-(3 H)-furan-2-one; Dihydrofuran-2(3H)-one; NSC 4592; dihydro-2(3H)-furanone (γ-butyrolactone); Tetrahydrofuran-2-one; Dihydro-2(3H)-furanone (-butyrolactone); Butan-4-olide; 2-Dihydrofuranone
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas phase ion energetics data
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
  • Switch to SI units

Data at NIST subscription sites:

• 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.

Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry 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 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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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 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
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Reduced pressure boiling point

Enthalpy of vaporization

Enthalpy of fusion

Entropy of fusion

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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: 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

=  + 

By formula: C₄H₈O₃ = H₂O + C₄H₆O₂

IR Spectrum

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

Data compiled by: Coblentz Society, Inc.

• Not specified, most likely a prism, grating, or hybrid spectrometer.; (NO SPECTRUM, ONLY SCANNED IMAGE IS AVAILABLE)
• LIQUID; BAIRD (GRATING); 2 cm^-1 resolution
• SOLUTION (10% IN CCl4 FOR 3800-1330, 10% IN CS2 FOR 1330-460 CM^-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

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

• gas

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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.

Wiberg and Waldron, 1991
Wiberg, K.B.; Waldron, R.F., Lactones. 2. Enthalpies of hydrolysis, reduction, and formation of the C₄-C₁₃ monocyclic lactones. strain energies and conformations, J. Am. Chem. Soc., 1991, 113, 7697-7705. [all data]

Leitao, Pilcher, et al., 1990
Leitao, M.L.P.; Pilcher, H.; Meng-Yan, Y.; Brown, J.M.; Conn, A.D., Enthalpies of combustion of γ-butyrolactone, γ-valerolactone, and δ-valerolactone, J. Chem. Thermodyn., 1990, 22, 885-891. [all data]

Brown, Conn, et al., 1989
Brown, J.M.; Conn, A.D.; Pilcher, G.; Leitao, M.L.P.; Yang, M.-Y., On the strain energy of 5-ring and 6-ring lactones, J. Chem. Soc., Chem. Commun., 1989, 1817-1819. [all data]

Steele, Chirico, et al., 1989
Steele, W.V.; Chirico, R.D.; Nguyen, A.; Hossenlopp, I.A.; Smith, N.K., Determination of some pure compound ideal-gas enthalpies of formation, AIChE Symp. Ser., 1989, 85, 140-162. [all data]

Ismailov, Gabzalilova, et al., 1988
Ismailov, T.S.; Gabzalilova, N.R.; Makhkamoov, Kh.M., Complex study of physicochemical properties of γ-butyrolactone, Uzb. Khim. Zh., 1988, 48-50. [all data]

Yevstropov, Lebedev, et al., 1980
Yevstropov, A.A.; Lebedev, B.V.; Kiparisova, Ye.G.; Alekseyev, V.A.; Stashina, G.A., Thermodynamic parameters of transformation of γ-butyrolactone into poly-γ-butyrolactone at normal pressure in the range of 0-400°K, Polym. Sci. USSR, 1980, 22, 2685-2692. [all data]

Kudchadker S.A., 1975
Kudchadker S.A., Thermodynamic properties of oxygen compounds. II. beta-Propiolactone, gamma-butyrolactone, and gamma-butyrolactam (2-pyrrolidone), Thermochim. Acta, 1975, 12, 11-17. [all data]

Lebedev and Yevstropov, 1983
Lebedev, B.V.; Yevstropov, A.A., Thermodynamics of β-propiolactone, t-butyrolactone, d-valerolactone, and e-caprolactone from 13.8 to 340 K, J. Chem. Thermodynam., 1983, 15, 115-128. [all data]

Yevstropov, Lebedev, et al., 1980, 2
Yevstropov, A.A.; Lebedev, B.V.; Kiparisova, Ye.G.; Alekseyev, V.A.; Stashina, G.A., Thermodynamic parameters of transformation of t-butyrolactone into poly-t-butyrolactone at normal pressure in the range of 0 to 400 K, Vysokomol. Soedin, Ser., 1980, A 22(11), 2450-2456. [all data]

Fuchs, 1979
Fuchs, R., Heat capacities of some liquid aliphatic, alicyclic, and aromatic esters at 298.15 K, J. Chem. Thermodyn., 1979, 11, 959-961. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Vasil'eva, Naumova, et al., 1990
Vasil'eva, I.I.; Naumova, A.A.; Polyakov, A.A.; Tyvina, T.N.; Kozlova, N.V., Vapor pressure and molar volume of liquid tetrahydrofuran, γ- butyrolactone, and dibutyl maleinate at elevated temperatures and pressures, Zh. Prikl. Khim. (Leningrad), 1990, 63, 1879-81. [all data]

Anonymous, 1954
Anonymous, R., , Am. Pet. Inst. Res. Proj. 45, Tech. Rep. 13, Ohio State Univ., 1954. [all data]

Lebedev and Yevstropov, 1983, 2
Lebedev, B.V.; Yevstropov, A.A. (see evstro aa), Thermodynamics of β-propiolactone, γ-butyrolactone, δ- valerolactone, and ε-caprolactone from 13.8 to 340 K, J. Chem. Thermodyn., 1983, 15, 115. [all data]

Evstropov, Lebedev, et al., 1980
Evstropov, A.A.; Lebedev, B.V.; Kiparisova, Ye.G.; Alekseev, V.A.; Stashina, G.A., Thermodynamic parameters of transformation of τ-butyrolactone into poly-τ-butryrolactone at normal pressure in the range of 0 to 400 K, Vysokomol. Soedin, Ser. A, 1980, 22, 2450-2456. [all data]

Evstropov, Lebedev, et al., 1979
Evstropov, A.A.; Lebedev, B.V.; Kiparisova, E.G.; Prusakova, I.L., Heat capacity and thermodynamic properties of gamma-butyrolactone in the O-330 K range., Termodin. Org. Soedin., 1979, No. 8, 14. [all data]

Wilson, Wilson, et al., 1996
Wilson, L.C.; Wilson, H.L.; Wilding, W.V.; Wilson, G.M., Critical Point Measurements for Fourteen Compounds by a Static Method and a Flow Method, J. Chem. Eng. Data, 1996, 41, 1252-4. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]

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]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  Cp,liquid	Constant pressure heat capacity of liquid
  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
  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
  ΔrH°	Enthalpy of reaction at standard conditions
  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.