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Butyrolactone

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Gas phase thermochemistry data

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

Quantity Value Units Method Reference Comment
Deltafgas-364. ± 3.kJ/molCmWiberg and Waldron, 1991Heat of reduction; ALS
Deltafgas-366.5 ± 0.8kJ/molCcbLeitao, Pilcher, et al., 1990See Brown, Conn, et al., 1989; ALS
Deltafgas-365.61 ± 0.44kJ/molCcbSteele, Chirico, et al., 1989ALS
Deltafgas-377.7kJ/molN/AIsmailov, Gabzalilova, et al., 1988Value computed using «DELTA»fHliquid° value of -431.2±2.7 kj/mol from Ismailov, Gabzalilova, et al., 1988 and «DELTA»vapH° value of 53.5 kj/mol from Steele, Chirico, et al., 1989.; DRB
Deltafgas-368.5kJ/molN/AYevstropov, Lebedev, et al., 1980Value computed using «DELTA»fHliquid° value of -422.0±1.1 kj/mol from Yevstropov, Lebedev, et al., 1980 and «DELTA»vapH° value of 53.5 kj/mol from Steele, Chirico, et al., 1989.; DRB

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
43.46100.Kudchadker S.A., 1975GT
50.99150.
60.82200.
79.20273.15
86.10298.15
86.62300.
114.24400.
138.77500.
159.18600.
176.01700.
189.98800.
201.69900.
211.551000.
219.911100.
227.021200.
233.101300.
238.331400.
242.821500.

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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

Quantity Value Units Method Reference Comment
Deltafliquid-419. ± 3.kJ/molCmWiberg and Waldron, 1991Heat of reduction; ALS
Deltafliquid-420.9 ± 0.7kJ/molCcbLeitao, Pilcher, et al., 1990See Brown, Conn, et al., 1989; ALS
Deltafliquid-419.07 ± 0.36kJ/molCcbSteele, Chirico, et al., 1989ALS
Deltafliquid-431.2 ± 2.7kJ/molCcbIsmailov, Gabzalilova, et al., 1988ALS
Deltafliquid-422.0 ± 1.1kJ/molCcbYevstropov, Lebedev, et al., 1980ALS
Quantity Value Units Method Reference Comment
Deltacliquid-2010.6 ± 0.5kJ/molCcbLeitao, Pilcher, et al., 1990See Brown, Conn, et al., 1989; Corresponding «DELTA»fliquid = -420.9 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-2012.46 ± 0.28kJ/molCcbSteele, Chirico, et al., 1989Corresponding «DELTA»fliquid = -419.07 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-2000.4 ± 6.4kJ/molCcbIsmailov, Gabzalilova, et al., 1988Corresponding «DELTA»fliquid = -431.14 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-2009.2 ± 0.8kJ/molCcbYevstropov, Lebedev, et al., 1980Corresponding «DELTA»fliquid = -422.3 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid197.4J/mol*KN/ALebedev and Yevstropov, 1983DH
liquid197.5J/mol*KN/AYevstropov, Lebedev, et al., 1980, 2DH
liquid201.28J/mol*KN/AIsmailov, Gabzalilova, et al., 1988DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
140.5298.15Steele, Chirico, et al., 1989DH
140.9298.15Ismailov, Gabzalilova, et al., 1988T = 290 to 410 K. Cp(liq) = 101.0829 + 763.3375X10-4T + 1.918968x10-4T2 J/mol*K (290 to 410 K).; DH
141.3298.15Lebedev and Yevstropov, 1983T = 13.8 to 340 K.; DH
141.3298.15Yevstropov, Lebedev, et al., 1980, 2T = 5 to 330 K.; DH
141.4298.15Fuchs, 1979DH

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
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil477.7KN/AAldrich Chemical Company Inc., 1990BS
Tboil479.20KN/AVasil'eva, Naumova, et al., 1990Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Tfus229.0KN/AAnonymous, 1954Uncertainty assigned by TRC = 0.6 K; TRC
Quantity Value Units Method Reference Comment
Ttriple229.78KN/ALebedev and Yevstropov, 1983, 2Uncertainty assigned by TRC = 0.02 K; TRC
Ttriple229.78KN/AEvstropov, Lebedev, et al., 1980Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; TRC
Ttriple229.78KN/AEvstropov, Lebedev, et al., 1979Uncertainty assigned by TRC = 0.05 K; TRC
Quantity Value Units Method Reference Comment
Tc731.0KN/AWilson, Wilson, et al., 1996Uncertainty assigned by TRC = 0.4 K; TRC
Quantity Value Units Method Reference Comment
Pc51.31barN/AWilson, Wilson, et al., 1996Uncertainty assigned by TRC = 0.40 bar; TRC
Quantity Value Units Method Reference Comment
Deltavap53. ± 5.kJ/molAVGN/AAverage of 16 values; Individual data points

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
362.20.016Weast and Grasselli, 1989BS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
49.5 ± 0.1392.EBWiberg and Waldron, 1991Based on data from 378. - 406. K.; AC
51.8 ± 0.6357.MMWiberg and Waldron, 1991Based on data from 345. - 370. K.; AC
48.2407.AStephenson and Malanowski, 1987Based on data from 392. - 474. K.; AC
45.2 ± 0.4349.VYevstropov, Lebedev, et al., 1980ALS

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
9.570229.78Lebedev and Yevstropov, 1983DH
9.570229.78Yevstropov, Lebedev, et al., 1980, 2DH
9.57230.Acree, 1991AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
41.56229.78Lebedev and Yevstropov, 1983DH
41.56229.78Yevstropov, Lebedev, et al., 1980, 2DH

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

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

Butanoic acid, 4-hydroxy- = Water + Butyrolactone

By formula: C4H8O3 = H2O + C4H6O2

Quantity Value Units Method Reference Comment
Deltar4.5 ± 0.2kJ/molCmWiberg and Waldron, 1991liquid phase

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Quantity Value Units Method Reference Comment
Proton affinity (review)840.0kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity808.1kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
10.26PEGerson, Worley, et al., 1978Vertical value; LLK
10.26PEBain and Frost, 1973Vertical value; LLK

IR Spectrum

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

Data compiled by: Coblentz Society, Inc.

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


Mass spectrum (electron ionization)

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

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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 NIST Mass Spectrometry Data Center, 1990.
NIST MS number 114691

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

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

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 «gamma»-butyrolactone, «gamma»-valerolactone, and «delta»-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 «gamma»-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 «gamma»-butyrolactone into poly-«gamma»-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 «beta»-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, «gamma»- 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 «beta»-propiolactone, «gamma»-butyrolactone, «delta»- valerolactone, and «epsilon»-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 «tau»-butyrolactone into poly-«tau»-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]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Gerson, Worley, et al., 1978
Gerson, S.H.; Worley, S.D.; Bodor, N.; Kaminski, J.J.; Flechtner, T.W., The photoelectron spectra of some heterocyclic compounds which contain N, O, Cl, and Br, J. Electron Spectrosc. Relat. Phenom., 1978, 13, 421. [all data]

Bain and Frost, 1973
Bain, A.D.; Frost, D.C., Studies of the carbonyl group in some five-membered ring compounds by photoelectron spectroscopy, Can. J. Chem., 1973, 51, 1245. [all data]


Notes

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