Butyrolactone
- Formula: C4H6O2
- Molecular weight: 86.0892
- 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:
- 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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Condensed phase thermochemistry data
Go To: Top, 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 |
---|---|---|---|---|---|
ΔfH°liquid | -100.2 ± 0.6 | kcal/mol | Cm | Wiberg and Waldron, 1991 | Heat of reduction; ALS |
ΔfH°liquid | -100.6 ± 0.2 | kcal/mol | Ccb | Leitao, Pilcher, et al., 1990 | See Brown, Conn, et al., 1989; ALS |
ΔfH°liquid | -100.16 ± 0.086 | kcal/mol | Ccb | Steele, Chirico, et al., 1989 | ALS |
ΔfH°liquid | -103.1 ± 0.65 | kcal/mol | Ccb | Ismailov, Gabzalilova, et al., 1988 | ALS |
ΔfH°liquid | -100.9 ± 0.26 | kcal/mol | Ccb | Yevstropov, Lebedev, et al., 1980 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -480.5 ± 0.1 | kcal/mol | Ccb | Leitao, Pilcher, et al., 1990 | See Brown, Conn, et al., 1989; Corresponding ΔfHºliquid = -100.6 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -480.989 ± 0.067 | kcal/mol | Ccb | Steele, Chirico, et al., 1989 | Corresponding ΔfHºliquid = -100.16 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -478.1 ± 1.5 | kcal/mol | Ccb | Ismailov, Gabzalilova, et al., 1988 | Corresponding ΔfHºliquid = -103.04 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -480.2 ± 0.2 | kcal/mol | Ccb | Yevstropov, Lebedev, et al., 1980 | Corresponding ΔfHºliquid = -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
Cp,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 |
References
Go To: Top, Condensed phase thermochemistry data, 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]
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]
Notes
Go To: Top, Condensed phase thermochemistry data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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