Butyrolactone

Formula: C₄H₆O₂
Molecular weight: 86.0892
IUPAC Standard InChI: InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2
IUPAC Standard InChIKey: YEJRWHAVMIAJKC-UHFFFAOYSA-N
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:
Other data available:
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, References, Notes

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
Δ_fH°_gas	-87.0 ± 0.8	kcal/mol	Cm	Wiberg and Waldron, 1991	Heat of reduction; ALS
Δ_fH°_gas	-87.6 ± 0.2	kcal/mol	Ccb	Leitao, Pilcher, et al., 1990	See Brown, Conn, et al., 1989; ALS
Δ_fH°_gas	-87.38 ± 0.11	kcal/mol	Ccb	Steele, Chirico, et al., 1989	ALS
Δ_fH°_gas	-90.27	kcal/mol	N/A	Ismailov, Gabzalilova, et al., 1988	Value computed using Δ_fH_liquid° value of -431.2±2.7 kj/mol from Ismailov, Gabzalilova, et al., 1988 and Δ_vapH° value of 53.5 kj/mol from Steele, Chirico, et al., 1989.; DRB
Δ_fH°_gas	-88.07	kcal/mol	N/A	Yevstropov, Lebedev, et al., 1980	Value computed using Δ_fH_liquid° value of -422.0±1.1 kj/mol from Yevstropov, Lebedev, et al., 1980 and Δ_vapH° value of 53.5 kj/mol from Steele, Chirico, et al., 1989.; DRB

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
10.39	100.	Kudchadker S.A., 1975	GT
12.19	150.
14.54	200.
18.93	273.15
20.58	298.15
20.70	300.
27.304	400.
33.167	500.
38.045	600.
42.067	700.
45.406	800.
48.205	900.
50.562	1000.
52.560	1100.
54.259	1200.
55.712	1300.
56.962	1400.
58.035	1500.

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, References, Notes

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
Δ_fH°_liquid	-100.2 ± 0.6	kcal/mol	Cm	Wiberg and Waldron, 1991	Heat of reduction; ALS
Δ_fH°_liquid	-100.6 ± 0.2	kcal/mol	Ccb	Leitao, Pilcher, et al., 1990	See Brown, Conn, et al., 1989; ALS
Δ_fH°_liquid	-100.16 ± 0.086	kcal/mol	Ccb	Steele, Chirico, et al., 1989	ALS
Δ_fH°_liquid	-103.1 ± 0.65	kcal/mol	Ccb	Ismailov, Gabzalilova, et al., 1988	ALS
Δ_fH°_liquid	-100.9 ± 0.26	kcal/mol	Ccb	Yevstropov, Lebedev, et al., 1980	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-480.5 ± 0.1	kcal/mol	Ccb	Leitao, Pilcher, et al., 1990	See Brown, Conn, et al., 1989; Corresponding Δ_fHº_liquid = -100.6 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-480.989 ± 0.067	kcal/mol	Ccb	Steele, Chirico, et al., 1989	Corresponding Δ_fHº_liquid = -100.16 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-478.1 ± 1.5	kcal/mol	Ccb	Ismailov, Gabzalilova, et al., 1988	Corresponding Δ_fHº_liquid = -103.04 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-480.2 ± 0.2	kcal/mol	Ccb	Yevstropov, Lebedev, et al., 1980	Corresponding Δ_fHº_liquid = -100.9 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	47.18	cal/mol*K	N/A	Lebedev and Yevstropov, 1983	DH
S°_liquid	47.20	cal/mol*K	N/A	Yevstropov, Lebedev, et al., 1980, 2	DH
S°_liquid	48.107	cal/mol*K	N/A	Ismailov, Gabzalilova, et al., 1988	DH

Constant pressure heat capacity of liquid

C_p,liquid (cal/mol*K)	Temperature (K)	Reference	Comment
33.58	298.15	Steele, Chirico, et al., 1989	DH
33.68	298.15	Ismailov, Gabzalilova, et al., 1988	T = 290 to 410 K. Cp(liq) = 101.0829 + 763.3375X10-4T + 1.918968x10-4T2 J/mol*K (290 to 410 K).; DH
33.77	298.15	Lebedev and Yevstropov, 1983	T = 13.8 to 340 K.; DH
33.77	298.15	Yevstropov, Lebedev, et al., 1980, 2	T = 5 to 330 K.; DH
33.80	298.15	Fuchs, 1979	DH

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References, Notes

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
T_boil	477.7	K	N/A	Aldrich Chemical Company Inc., 1990	BS
T_boil	479.20	K	N/A	Vasil'eva, Naumova, et al., 1990	Uncertainty assigned by TRC = 0.2 K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_fus	229.0	K	N/A	Anonymous, 1954	Uncertainty assigned by TRC = 0.6 K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_triple	229.78	K	N/A	Lebedev and Yevstropov, 1983, 2	Uncertainty assigned by TRC = 0.02 K; TRC
T_triple	229.78	K	N/A	Evstropov, Lebedev, et al., 1980	Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; TRC
T_triple	229.78	K	N/A	Evstropov, Lebedev, et al., 1979	Uncertainty assigned by TRC = 0.05 K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_c	731.0	K	N/A	Wilson, Wilson, et al., 1996	Uncertainty assigned by TRC = 0.4 K; TRC
Quantity	Value	Units	Method	Reference	Comment
P_c	50.64	atm	N/A	Wilson, Wilson, et al., 1996	Uncertainty assigned by TRC = 0.39 atm; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	13. ± 1.	kcal/mol	AVG	N/A	Average of 16 values; Individual data points

Reduced pressure boiling point

T_boil (K)	Pressure (atm)	Reference	Comment
362.2	0.016	Weast and Grasselli, 1989	BS

Enthalpy of vaporization

Δ_vapH (kcal/mol)	Temperature (K)	Method	Reference	Comment
11.8 ± 0.02	392.	EB	Wiberg and Waldron, 1991	Based on data from 378. to 406. K.; AC
12.4 ± 0.1	357.	MM	Wiberg and Waldron, 1991	Based on data from 345. to 370. K.; AC
11.5	407.	A	Stephenson and Malanowski, 1987	Based on data from 392. to 474. K.; AC
10.8 ± 0.1	349.	V	Yevstropov, Lebedev, et al., 1980	ALS

Enthalpy of fusion

Δ_fusH (kcal/mol)	Temperature (K)	Reference	Comment
2.287	229.78	Lebedev and Yevstropov, 1983	DH
2.287	229.78	Yevstropov, Lebedev, et al., 1980, 2	DH
2.29	230.	Acree, 1991	AC

Entropy of fusion

Δ_fusS (cal/mol*K)	Temperature (K)	Reference	Comment
9.933	229.78	Lebedev and Yevstropov, 1983	DH
9.933	229.78	Yevstropov, Lebedev, et al., 1980, 2	DH

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, References, Notes

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

= + Butyrolactone

By formula: C₄H₈O₃ = H₂O + C₄H₆O₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1.08 ± 0.05	kcal/mol	Cm	Wiberg and Waldron, 1991	liquid phase

References

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

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, References

Symbols used in this document:

C_p,gas	Constant pressure heat capacity of gas
C_p,liquid	Constant pressure heat capacity of liquid
P_c	Critical pressure
S°_liquid	Entropy of liquid at standard conditions
T_boil	Boiling point
T_c	Critical temperature
T_fus	Fusion (melting) point
T_triple	Triple point temperature
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_fusH	Enthalpy of fusion
Δ_fusS	Entropy of fusion
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	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.