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
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Other data available:
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- Gas Phase Kinetics Database
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Gas phase thermochemistry data

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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

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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

Reaction thermochemistry data

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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

Gas phase ion energetics data

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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)	200.8	kcal/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	193.1	kcal/mol	N/A	Hunter and Lias, 1998	HL

Ionization energy determinations

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

References

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

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

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Symbols used in this document:

C_p,gas	Constant pressure heat capacity of gas
C_p,liquid	Constant pressure heat capacity of liquid
S°_liquid	Entropy of liquid at standard conditions
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_rH°	Enthalpy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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