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:
- 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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Gas phase thermochemistry 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:
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 |
|---|---|---|---|---|---|
| ΔfH°gas | -364. ± 3. | kJ/mol | Cm | Wiberg and Waldron, 1991 | Heat of reduction; ALS |
| ΔfH°gas | -366.5 ± 0.8 | kJ/mol | Ccb | Leitao, Pilcher, et al., 1990 | See Brown, Conn, et al., 1989; ALS |
| ΔfH°gas | -365.61 ± 0.44 | kJ/mol | Ccb | Steele, Chirico, et al., 1989 | ALS |
| ΔfH°gas | -377.7 | kJ/mol | N/A | Ismailov, Gabzalilova, et al., 1988 | Value computed using ΔfHliquid° value of -431.2±2.7 kj/mol from Ismailov, Gabzalilova, et al., 1988 and ΔvapH° value of 53.5 kj/mol from Steele, Chirico, et al., 1989.; DRB |
| ΔfH°gas | -368.5 | kJ/mol | N/A | Yevstropov, Lebedev, et al., 1980 | Value computed using ΔfHliquid° value of -422.0±1.1 kj/mol from Yevstropov, Lebedev, et al., 1980 and ΔvapH° 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 |
|---|---|---|---|
| 43.46 | 100. | Kudchadker S.A., 1975 | GT |
| 50.99 | 150. | ||
| 60.82 | 200. | ||
| 79.20 | 273.15 | ||
| 86.10 | 298.15 | ||
| 86.62 | 300. | ||
| 114.24 | 400. | ||
| 138.77 | 500. | ||
| 159.18 | 600. | ||
| 176.01 | 700. | ||
| 189.98 | 800. | ||
| 201.69 | 900. | ||
| 211.55 | 1000. | ||
| 219.91 | 1100. | ||
| 227.02 | 1200. | ||
| 233.10 | 1300. | ||
| 238.33 | 1400. | ||
| 242.82 | 1500. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, 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 | -419. ± 3. | kJ/mol | Cm | Wiberg and Waldron, 1991 | Heat of reduction; ALS |
| ΔfH°liquid | -420.9 ± 0.7 | kJ/mol | Ccb | Leitao, Pilcher, et al., 1990 | See Brown, Conn, et al., 1989; ALS |
| ΔfH°liquid | -419.07 ± 0.36 | kJ/mol | Ccb | Steele, Chirico, et al., 1989 | ALS |
| ΔfH°liquid | -431.2 ± 2.7 | kJ/mol | Ccb | Ismailov, Gabzalilova, et al., 1988 | ALS |
| ΔfH°liquid | -422.0 ± 1.1 | kJ/mol | Ccb | Yevstropov, Lebedev, et al., 1980 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -2010.6 ± 0.5 | kJ/mol | Ccb | Leitao, Pilcher, et al., 1990 | See Brown, Conn, et al., 1989; Corresponding ΔfHºliquid = -420.9 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -2012.46 ± 0.28 | kJ/mol | Ccb | Steele, Chirico, et al., 1989 | Corresponding ΔfHºliquid = -419.07 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -2000.4 ± 6.4 | kJ/mol | Ccb | Ismailov, Gabzalilova, et al., 1988 | Corresponding ΔfHºliquid = -431.14 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -2009.2 ± 0.8 | kJ/mol | Ccb | Yevstropov, Lebedev, et al., 1980 | Corresponding ΔfHºliquid = -422.3 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 197.4 | J/mol*K | N/A | Lebedev and Yevstropov, 1983 | DH |
| S°liquid | 197.5 | J/mol*K | N/A | Yevstropov, Lebedev, et al., 1980, 2 | DH |
| S°liquid | 201.28 | J/mol*K | N/A | Ismailov, Gabzalilova, et al., 1988 | DH |
Constant pressure heat capacity of liquid
| Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 140.5 | 298.15 | Steele, Chirico, et al., 1989 | DH |
| 140.9 | 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 |
| 141.3 | 298.15 | Lebedev and Yevstropov, 1983 | T = 13.8 to 340 K.; DH |
| 141.3 | 298.15 | Yevstropov, Lebedev, et al., 1980, 2 | T = 5 to 330 K.; DH |
| 141.4 | 298.15 | Fuchs, 1979 | DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 4.5 ± 0.2 | kJ/mol | Cm | Wiberg and Waldron, 1991 | liquid phase |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction 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]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas 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°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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