Tetrahydropyran
- Formula: C5H10O
- Molecular weight: 86.1323
- IUPAC Standard InChIKey: DHXVGJBLRPWPCS-UHFFFAOYSA-N
- CAS Registry Number: 142-68-7
- 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. - Other names: Oxacyclohexane; Oxane; 2H-Pyran, tetrahydro-; Pentamethylene oxide; Tetrahydro-2H-pyran; THP
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Gas phase thermochemistry data
Go To: Top, Phase change data, Mass spectrum (electron ionization), 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -223.8 ± 1.0 | kJ/mol | Cm | Pell and Pilcher, 1965 | ALS |
ΔfH°gas | -220. ± 3. | kJ/mol | Ccb | Snelson and Skinner, 1961 | ALS |
ΔfH°gas | -223.4 ± 1.5 | kJ/mol | Ccb | Cass, Fletcher, et al., 1958 | Reanalyzed by Cox and Pilcher, 1970, Original value = -212. kJ/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°gas | -3173.3 ± 0.96 | kJ/mol | Cm | Pell and Pilcher, 1965 | Corresponding ΔfHºgas = -223.4 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
33.90 | 50. | Dorofeeva O.V., 1992 | p=1 bar. Selected values are in close agreement with those calculated by [ Vedal D., 1975].; GT |
41.62 | 100. | ||
53.05 | 150. | ||
66.28 | 200. | ||
90.06 | 273.15 | ||
99.1 ± 3.0 | 298.15 | ||
99.82 | 300. | ||
137.09 | 400. | ||
171.01 | 500. | ||
199.70 | 600. | ||
223.66 | 700. | ||
243.80 | 800. | ||
260.83 | 900. | ||
275.32 | 1000. | ||
287.68 | 1100. | ||
298.26 | 1200. | ||
307.34 | 1300. | ||
315.16 | 1400. | ||
321.92 | 1500. |
Phase change data
Go To: Top, Gas phase thermochemistry data, Mass spectrum (electron ionization), 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
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 361.0 ± 0.7 | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 224. | K | N/A | Guieu, Carbonnel, et al., 1985 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.1 K; TRC |
Tfus | 224.15 | K | N/A | Brooks and Pilcher, 1959 | Uncertainty assigned by TRC = 1. K; TRC |
Tfus | 223.95 | K | N/A | Anonymous, 1942 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 572.2 | K | N/A | Kobe and Mathews, 1970 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 47.70 | bar | N/A | Kobe and Mathews, 1970 | Uncertainty assigned by TRC = 0.1418 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 3.8124 | mol/l | N/A | Kobe and Mathews, 1970 | Uncertainty assigned by TRC = 0.0056 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 34.67 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 38.2 ± 1.1 | kJ/mol | DSC | Rojas-Aguilar, Ginez-Carbajal, et al., 2005 | AC |
ΔvapH° | 35.0 | kJ/mol | N/A | Snelson and Skinner, 1961 | DRB |
ΔvapH° | 34.9 | kJ/mol | V | Cass, Fletcher, et al., 1958 | ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
31.17 | 361. | N/A | Majer and Svoboda, 1985 | |
36. | 301. | N/A | Rodríguez, Giner, et al., 2006 | Based on data from 286. to 361. K.; AC |
33.2 | 350. | N/A | Rodriguez, Artigas, et al., 2000 | Based on data from 335. to 412. K.; AC |
35.0 | 288. | A | Stephenson and Malanowski, 1987 | Based on data from 273. to 362. K.; AC |
35.0 | 281. | N/A | Dykyj, 1972 | Based on data from 273. to 288. K. See also Cass, Fletcher, et al., 1958, 2.; AC |
36. | 293. | V | Skuratov, Strepikheev, et al., 1957 | Combustion at 293 K; ALS |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, 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
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW-1046 |
NIST MS number | 229215 |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Pell and Pilcher, 1965
Pell, A.S.; Pilcher, G.,
Measurements of heats of combustion by flame calorimetry. Part 3.-Ethylene oxide, trimethylene oxide, tetrahydrofuran and tetrahydropy,
Trans. Faraday Soc., 1965, 61, 71-77. [all data]
Snelson and Skinner, 1961
Snelson, A.; Skinner, H.A.,
Heats of combustion: sec-propanol, 1,4-dioxan, 1,3-dioxan and tetrahydropyran,
Trans. Faraday Soc., 1961, 57, 2125-2131. [all data]
Cass, Fletcher, et al., 1958
Cass, R.C.; Fletcher, S.E.; Mortimer, C.T.; Springall, H.D.; White, T.R.,
Heats of combustion and molecular structure. Part V. The mean bond energy term for the C-O bond in ethers, and the structures of some cyclic ethers,
J. Chem. Soc., 1958, 1406-1410. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Dorofeeva O.V., 1992
Dorofeeva O.V.,
Ideal gas thermodynamic properties of oxygen heterocyclic compounds. Part 2. Six-membered, seven-membered and eight-membered rings,
Thermochim. Acta, 1992, 200, 121-150. [all data]
Vedal D., 1975
Vedal D.,
Vibrational spectra of pentamethylene sulfide and selenide,
Spectrochim. Acta, 1975, A31, 355-372. [all data]
Guieu, Carbonnel, et al., 1985
Guieu, R.; Carbonnel, L.; Kehiaian, H.V.,
Solutions solides organiques I. Etude des diagrammes de phases des systemes oxanne ou 1,4-dioxanne + cyclohexane,
Bull. Soc. Chim. Fr., 1985, 1985, 709. [all data]
Brooks and Pilcher, 1959
Brooks, J.H.; Pilcher, G.,
A Simple Melting Point Calorimeter for Moderately Precise Determination of Purity,
J. Chem. Soc., 1959, 1959, 1535. [all data]
Anonymous, 1942
Anonymous, R.,
, Am. Pet. Inst. Res. Proj. 6, Natl. Bur. Stand., 1942. [all data]
Kobe and Mathews, 1970
Kobe, K.A.; Mathews, J.F.,
Critical Properties and Vapor Pressures of Some Organic Nitrogen and Oxygen Compounds,
J. Chem. Eng. Data, 1970, 15, 182. [all data]
Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]
Rojas-Aguilar, Ginez-Carbajal, et al., 2005
Rojas-Aguilar, A.; Ginez-Carbajal, F.; Orozco-Guareno, E.; Flores-Segura, H.,
Measurement of enthalpies of vaporization of volatile heterocyclic compounds by DSC,
J Therm Anal Calorim, 2005, 79, 1, 95-100, https://doi.org/10.1007/s10973-004-0568-3
. [all data]
Rodríguez, Giner, et al., 2006
Rodríguez, S.; Giner, B.; Haro, M.; Martín, S.; Artigas, H.,
Isobaric vapour--liquid equilibrium for the binary systems formed by a cyclic ether and bromocyclohexane at 40.0 and 101.3 kPa,
Physics and Chemistry of Liquids, 2006, 44, 3, 275-285, https://doi.org/10.1080/00319100600574168
. [all data]
Rodriguez, Artigas, et al., 2000
Rodriguez, S.; Artigas, H.; Lafuente, C.; Mainar, A.M.; Royo, F.M.,
Isobaric vapour--liquid equilibrium of binary mixtures of some cyclic ethers with chlorocyclohexane at 40.0 and 101.3 kPa,
Thermochimica Acta, 2000, 362, 1-2, 153-160, https://doi.org/10.1016/S0040-6031(00)00580-3
. [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]
Dykyj, 1972
Dykyj, J.,
Petrochemia, 1972, 12, 1, 13. [all data]
Cass, Fletcher, et al., 1958, 2
Cass, R.C.; Fletcher, S.E.; Mortimer, C.T.; Quincey, P.G.; Springall, H.D.,
193. Heats of combustion and molecular structure. Part IV. Aliphatic nitroalkanes and nitric esters,
J. Chem. Soc., 1958, 958, https://doi.org/10.1039/jr9580000958
. [all data]
Skuratov, Strepikheev, et al., 1957
Skuratov, S.M.; Strepikheev, A.A.; Kozina, M.P.,
About the reaction activity of five and six-membered heterocyclic compounds,
Dokl. Akad. Nauk SSSR, 1957, 117, 452-454. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point ΔcH°gas Enthalpy of combustion of gas at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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