2H-Pyran-2-one, tetrahydro-
- Formula: C5H8O2
- Molecular weight: 100.1158
- IUPAC Standard InChI: InChI=1S/C5H8O2/c6-5-3-1-2-4-7-5/h1-4H2
- IUPAC Standard InChIKey: OZJPLYNZGCXSJM-UHFFFAOYSA-N
- CAS Registry Number: 542-28-9
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: δ-Valerolactone; δ-Valeryllactone; Pentanoic acid, 5-hydroxy-, δ-lactone; Tetrahydro-2-pyranone; 5-Valerolactone; Valeric acid, δ-hydroxy-, δ-lactone; 5-Hydroxypentanoic acid δ-lactone; 1-Oxacyclohexan-2-one; Tetrahydro-2H-pyran-2-one; Delta-valerolactone; δ-Pentalactone; 5-Pentanolide; Cyclopentanolide; Tetrahydropyran-2-one; NSC 6247; Pentan-5-olide; γ-Valerolactone
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Phase change data
Go To: Top, Gas Chromatography, 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:
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 |
|---|---|---|---|---|---|
| Tboil | 492.2 | K | N/A | Weast and Grasselli, 1989 | BS |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 262.8 | K | N/A | Anonymous, 1955 | Uncertainty assigned by TRC = 0.6 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| Ttriple | 262.82 | K | N/A | Lebedev and Yevstropov, 1983 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
| Ttriple | 262.82 | K | N/A | Evstropov, Lebedev, et al., 1982 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
| Ttriple | 262.82 | K | N/A | Evstopov, Lebedev, et al., 1981 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; C3 to C2: Non-isothermal transition; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 14.1 ± 0.5 | kcal/mol | AVG | N/A | Average of 7 values; Individual data points |
Reduced pressure boiling point
| Tboil (K) | Pressure (atm) | Reference | Comment |
|---|---|---|---|
| 332.2 | 0.0007 | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of vaporization
| ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 12.5 ± 0.05 | 410. | EB | Wiberg and Waldron, 1991 | Based on data from 393. to 428. K.; AC |
| 11.6 | 387. | N/A | Schuette and Thomas, 1930 | Based on data from 342. to 433. K.; AC |
Enthalpy of fusion
| ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 2.517 | 263. | Acree, 1991 | AC |
Enthalpy of phase transition
| ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
|---|---|---|---|---|---|
| 0.109 | 118.1 | crystaline, IV | crystaline, III | Lebedev and Yevstropov, 1983, 2 | DH |
| 0.0741 | 122. to 155. | crystaline, III | crystaline, II | Lebedev and Yevstropov, 1983, 2 | DH |
| 0.0490 | 180. to 225. | crystaline, II | crystaline, I | Lebedev and Yevstropov, 1983, 2 | DH |
| 2.5167 | 262.82 | crystaline, I | liquid | Lebedev and Yevstropov, 1983, 2 | DH |
| 0.109 | 118. | crystaline, IV | crystaline, III | Yevstropov, Lebedev, et al., 1982 | DH |
| 0.0741 | 122. to 155. | crystaline, III | crystaline, II | Yevstropov, Lebedev, et al., 1982 | DH |
| 0.0490 | 180. to 225. | crystaline, II | crystaline, I | Yevstropov, Lebedev, et al., 1982 | DH |
| 2.5167 | 262.82 | crystaline, I | liquid | Yevstropov, Lebedev, et al., 1982 | DH |
| 0.109 | 118.1 | crystaline, IV | crystaline, III | Evstopov, Lebedev, et al., 1981 | DH |
| 0.0741 | 122. to 155. | crystaline, III | crystaline, II | Evstopov, Lebedev, et al., 1981 | DH |
| 0.0490 | 180. to 225. | crystaline, II | crystaline, I | Evstopov, Lebedev, et al., 1981 | DH |
| 2.5167 | 262.82 | crystaline, I | liquid | Evstopov, Lebedev, et al., 1981 | DH |
Entropy of phase transition
| ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
|---|---|---|---|---|---|
| 0.927 | 118.1 | crystaline, IV | crystaline, III | Lebedev and Yevstropov, 1983, 2 | DH |
| 0.53 | 122. to 155. | crystaline, III | crystaline, II | Lebedev and Yevstropov, 1983, 2 | DH |
| 0.22 | 180. to 225. | crystaline, II | crystaline, I | Lebedev and Yevstropov, 1983, 2 | DH |
| 9.431 | 262.82 | crystaline, I | liquid | Lebedev and Yevstropov, 1983, 2 | DH |
| 0.927 | 118. | crystaline, IV | crystaline, III | Yevstropov, Lebedev, et al., 1982 | DH |
| 0.53 | 122. to 155. | crystaline, III | crystaline, II | Yevstropov, Lebedev, et al., 1982 | DH |
| 0.22 | 180. to 225. | crystaline, II | crystaline, I | Yevstropov, Lebedev, et al., 1982 | DH |
| 9.431 | 262.82 | crystaline, I | liquid | Yevstropov, Lebedev, et al., 1982 | DH |
| 0.927 | 118.1 | crystaline, IV | crystaline, III | Evstopov, Lebedev, et al., 1981 | DH |
| 0.53 | 122. to 155. | crystaline, III | crystaline, II | Evstopov, Lebedev, et al., 1981 | DH |
| 0.22 | 180. to 225. | crystaline, II | crystaline, I | Evstopov, Lebedev, et al., 1981 | DH |
| 9.431 | 262.82 | crystaline, I | liquid | Evstopov, Lebedev, et al., 1981 | DH |
Gas Chromatography
Go To: Top, Phase change 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-1 | 1010. | Osorio, Alarcon, et al., 2006 | 25. m/0.2 mm/0.33 μm, 4. K/min; Tstart: 50. C; Tend: 300. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5 | 954. | Andrade, Sampaio, et al., 2007 | 30. m/0.25 mm/0.25 μm, He; Program: 40C(2min) => 4C/min => 220C => 20C/min => 280C |
Van Den Dool and Kratz RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-Wax | 1780. | Osorio, Alarcon, et al., 2006 | 30. m/0.25 mm/0.25 μm, He, 50. C @ 4. min, 4. K/min, 220. C @ 20. min |
| Capillary | DB-Wax | 1784. | Fröhlich, Duque, et al., 1989 | 30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min; Tend: 250. C |
| Capillary | DB-Wax | 1785. | Fröhlich, Duque, et al., 1989 | 30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min; Tend: 250. C |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | VF-5 MS | 961. | Leffingwell and Alford, 2011 | 60. m/0.32 mm/0.25 μm, Helium, 2. K/min, 260. C @ 28. min; Tstart: 30. C |
| Capillary | VF-5 MS | 965. | Leffingwell and Alford, 2011 | 60. m/0.32 mm/0.25 μm, Helium, 2. K/min, 260. C @ 28. min; Tstart: 30. C |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-1 | 991. | Ciccioli, Cecinato, et al., 1994 | 60. m/0.32 mm/0.25 μm; Program: not specified |
| Capillary | DB-1 | 991. | Ciccioli, Brancaleoni, et al., 1993 | 60. m/0.32 mm/0.25 μm; Program: 3 min at 5 C; 5 - 50 C at 3 deg/min; 50 - 220 C at 5 deg/min |
Normal alkane RI, polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Stabilwax | 1786. | Chinnici, Guerrero, et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium; Program: 35 0C 3 0C/min -> 100 0C 5 0C/min -> 240 0C (10 min) |
| Capillary | Carbowax 20M | 1730. | Vinogradov, 2004 | Program: not specified |
References
Go To: Top, Phase change data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Anonymous, 1955
Anonymous, R.,
, Am. Pet. Inst. Res. Proj. 45, Tech. Rep. 14, No. 1, Ohio State Univ., 1955. [all data]
Lebedev and Yevstropov, 1983
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., 1982
Evstropov, A.A.; Lebedev, B.V.; Kulagina, T.G.; Lebedev, N.K.,
Calorimetric study of γ-valerolactone, poly-γ-valerolactone and of the process of polymerization of γ-valerolactone in the 13.8 to 340 K temperature range,
Vysokomol. Soedin., Ser. A, 1982, 24, 568-574. [all data]
Evstopov, Lebedev, et al., 1981
Evstopov, A.A.; Lebedev, B.V.; Kulagina, T.G.; Lebedev, N.K.,
Thermodynamics of the polymerization process of d-valerolactone and poly-d-valerolactone in the range 0 to 350 K,
Termodin. Org. Soedin., 1981, 20-31. [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]
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]
Schuette and Thomas, 1930
Schuette, H.A.; Thomas, Ralph W.,
NORMAL VALEROLACTONE. II. ITS VAPOR PRESSURE,
J. Am. Chem. Soc., 1930, 52, 5, 2028-2030, https://doi.org/10.1021/ja01368a046
. [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]
Lebedev and Yevstropov, 1983, 2
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., 1982
Yevstropov, A.A.; Lebedev, B.V.; Kulagina, T.G.; Lebedev, N.K.,
Calorimetric study of d-valerolactone, poly-d-valerolactone and of the process of polymerization of d-valerolactone in the 13.8 to 340 K temperature range, Vysokomol. Soedin.,
Ser. A, 1982, 24, 568-574. [all data]
Osorio, Alarcon, et al., 2006
Osorio, C.; Alarcon, M.; Moreno, C.; Bonilla, A.; Barrios, J.; Garzon, C.; Duque, C.,
Characterization of Odor-Active Volatiles in Champa ( Campomanesia lineatifolia R. P.),
J. Agric. Food Chem., 2006, 54, 2, 509-516, https://doi.org/10.1021/jf052098c
. [all data]
Andrade, Sampaio, et al., 2007
Andrade, M.S.; Sampaio, T.S.; Nogueira, P.C.L.; Ribeiro, A.S.; Bittrich, V.; Amaral, M.C.E.,
Volatile compounds of the leaves, flowers and fruits of Kielmeyera rugosa Choisy (Clusiaceae),
Flavour Fragr. J., 2007, 22, 1, 49-52, https://doi.org/10.1002/ffj.1751
. [all data]
Fröhlich, Duque, et al., 1989
Fröhlich, O.; Duque, C.; Schreier, P.,
Volatile constituents of curuba (Passiflora mollissima) fruit,
J. Agric. Food Chem., 1989, 37, 2, 421-425, https://doi.org/10.1021/jf00086a033
. [all data]
Leffingwell and Alford, 2011
Leffingwell, J.; Alford, E.D.,
Volatile constituents of the giant pufball mushroom (Calvatia gigantea),
Leffingwell Rep., 2011, 4, 1-17. [all data]
Ciccioli, Cecinato, et al., 1994
Ciccioli, P.; Cecinato, A.; Brancaleoni, E.; Brachetti, A.; Frattoni, M.; Sparapani, R.,
Composition and Distribution of Polar and Non-Polar VOCs in Urban, Rural, Forest and Remote Areas,
Eur Commission EUR, 1994, 549-568. [all data]
Ciccioli, Brancaleoni, et al., 1993
Ciccioli, P.; Brancaleoni, E.; Cecinato, A.; Sparapani, R.; Frattoni, M.,
Identification and determination of biogenic and anthropogenic volatile organic compounds in forest areas of Northern and Southern Europe and a remote site of the Himalaya region by high-resolution gas chromatography-mass spectrometry,
J. Chromatogr., 1993, 643, 1-2, 55-69, https://doi.org/10.1016/0021-9673(93)80541-F
. [all data]
Chinnici, Guerrero, et al., 2009
Chinnici, F.; Guerrero, E.D.; Sonni, F.; Natali, N.; Marin, R.N.; Riponi, C.,
Gas chromatography - mass spectrometry (GC-MS) characterization of volatile compounds in quality vinegars with protected Europian geographical indication,
J. Agric. Food Chem., 2009, 57, 11, 4784-4792, https://doi.org/10.1021/jf804005w
. [all data]
Vinogradov, 2004
Vinogradov, B.A.,
Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]
Notes
Go To: Top, Phase change data, Gas Chromatography, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔfusH Enthalpy of fusion ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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