Tetrahydrofuran
- Formula: C4H8O
- Molecular weight: 72.1057
- IUPAC Standard InChIKey: WYURNTSHIVDZCO-UHFFFAOYSA-N
- CAS Registry Number: 109-99-9
- 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: Furan, tetrahydro-; Butane α,δ-oxide; Butane, 1,4-epoxy-; Cyclotetramethylene oxide; Furanidine; Oxacyclopentane; Oxolane; Tetramethylene oxide; THF; Hydrofuran; Tetrahydrofuraan; Tetrahydrofuranne; Tetraidrofurano; NCI-C60560; Rcra waste number U213; UN 2056; Diethylene oxide; Dynasolve 150; Tetrahydrofurane; THF (tetrahydrofuran); NSC 57858
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Phase change 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:
DH - Eugene S. Domalski and Elizabeth D. Hearing
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 339. ± 1. | K | AVG | N/A | Average of 16 out of 17 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 165.1 | K | N/A | Hayduk, Laudie, et al., 1973 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 164.15 | K | N/A | Brooks and Pilcher, 1959 | Uncertainty assigned by TRC = 1. K; TRC |
Tfus | 164.63 | K | N/A | Boord, Greenlee, et al., 1946 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 164.05 | K | N/A | Dolliver, Gresham, et al., 1938 | Uncertainty assigned by TRC = 0.4 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 164.76 | K | N/A | Wilhoit, Chao, et al., 1985 | Uncertainty assigned by TRC = 0.05 K; TRC |
Ttriple | 164.76 | K | N/A | Lebedev, Lityagov, et al., 1979 | Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 164.76 | K | N/A | Lebedev, Rabinovich, et al., 1978 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 540.2 | K | N/A | Majer and Svoboda, 1985 | |
Tc | 540.1 | K | N/A | Cheng, McCoubrey, et al., 1962 | Uncertainty assigned by TRC = 0.3 K; Visual (5-cm 2-mm bore tubes) in nitrate-nitrite bath, TE or TH cal. vs NPL thermometer.; TRC |
Tc | 541. | K | N/A | Kobe, Ravicz, et al., 1956 | Uncertainty assigned by TRC = 1.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 51.22 | atm | N/A | Kobe, Ravicz, et al., 1956 | Uncertainty assigned by TRC = 0.5000 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Vc | 0.225 | l/mol | N/A | Kobe, Ravicz, et al., 1956 | Uncertainty assigned by TRC = 0.003 l/mol; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 7.686 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 7.6 | kcal/mol | C | Hossenlopp and Scott, 1981 | AC |
ΔvapH° | 7.86 | kcal/mol | N/A | Moiseev and Antonova, 1970 | Based on data from 224. to 360. K.; AC |
ΔvapH° | 7.6 | kcal/mol | V | Cass, Fletcher, et al., 1958 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
7.125 | 339.1 | N/A | Majer and Svoboda, 1985 | |
7.72 | 305. | N/A | Loras, Aucejo, et al., 2001 | Based on data from 290. to 339. K.; AC |
7.91 | 288. | A | Stephenson and Malanowski, 1987 | Based on data from 273. to 339. K.; AC |
6.9 | 414. | A | Stephenson and Malanowski, 1987 | Based on data from 399. to 479. K.; AC |
7.07 | 482. | A | Stephenson and Malanowski, 1987 | Based on data from 467. to 541. K.; AC |
7.77 ± 0.05 | 288. | N/A | Borisov and Chugunova, 1976 | Based on data from 235. to 340. K.; AC |
7.36 | 320. | N/A | Rivenq, 1975 | Based on data from 302. to 339. K.; AC |
7.84 | 288. | N/A | Koizumi and Ouchi, 1970 | Based on data from 273. to 308. K. See also Boublik, Fried, et al., 1984.; AC |
7.62 | 311. | N/A | Scott D.W., 1970 | Based on data from 296. to 373. K. See also Boublik, Fried, et al., 1984.; AC |
7.8 | 293. | V | Skuratov, Strepikheev, et al., 1957 | Combustion at 293 K; ALS |
7.60 | 313. | N/A | Klages and Möhler, 1948 | Based on data from 293. to 313. K. See also Cass, Fletcher, et al., 1958, 2.; AC |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kcal/mol)
Tr = reduced temperature (T / Tc)
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Temperature (K) | A (kcal/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
302. to 339. | 11.02 | 0.2699 | 540.2 | Majer and Svoboda, 1985 |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
296.29 to 372.8 | 4.11547 | 1202.942 | -46.818 | Scott D.W., 1970 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.041 | 164.76 | Lebedev, Rabinovich, et al., 1978, 2 | DH |
2.041 | 164.76 | Lebedev and Lityagov, 1977 | DH |
2.04 | 164.8 | Acree, 1991 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
12.4 | 164.76 | Lebedev, Rabinovich, et al., 1978, 2 | DH |
12.39 | 164.76 | Lebedev and Lityagov, 1977 | DH |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
2.041 | 164.76 | crystaline, I | liquid | Lebedev, Lityagov, et al., 1979 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
12.39 | 164.76 | crystaline, I | liquid | Lebedev, Lityagov, et al., 1979 | DH |
References
Go To: Top, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Hayduk, Laudie, et al., 1973
Hayduk, W.; Laudie, H.; Smith, O.H.,
Viscosity, Freezing Point, Vapor-Liquid Equilibria, and Other Properties of Aqueous-Tetrahydrofuran Solutions,
J. Chem. Eng. Data, 1973, 18, 373-6. [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]
Boord, Greenlee, et al., 1946
Boord, C.E.; Greenlee, K.W.; Perilstein, W.L.,
The Synthesis, Purification and Prop. of Hydrocarbons of Low Mol. Weight, Am. Pet. Inst. Res. Proj. 45, Eighth Annu. Rep., Ohio State Univ., June 30, 1946. [all data]
Dolliver, Gresham, et al., 1938
Dolliver, M.A.; Gresham, T.L.; Kistiakowsky, G.B.; Smith, E.A.; Vaughan, W.E.,
Heats of Organic Reactions VI. Heats of Hydrogenation of Some Oxygen- Containing Compounds,
J. Am. Chem. Soc., 1938, 60, 440. [all data]
Wilhoit, Chao, et al., 1985
Wilhoit, R.C.; Chao, J.; Hall, K.R.,
Thermodynamic Properties of Key Organic Compounds in the Carbon Range C1 to C4. Part 1. Properties of Condensed Phases,
J. Phys. Chem. Ref. Data, 1985, 14, 1. [all data]
Lebedev, Lityagov, et al., 1979
Lebedev, B.V.; Lityagov, V.Ya.; Krentsina, T.I.; Milov, V.I.,
Thermodynamic properties of tetrahydrofuran in the range 8-322 K,
Zhur. Fiz. Khim., 1979, 53, 264-265. [all data]
Lebedev, Rabinovich, et al., 1978
Lebedev, B.V.; Rabinovich, I.B.; Milov, V.I.; Sladkov, A.M.,
Thermodynamic properties of tetrahydrofuran from 8 to 322 k polyaddition products with the bis-ethinyl derivatives of the same metals,
J. Chem. Thermodyn., 1978, 10, 321-9. [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]
Cheng, McCoubrey, et al., 1962
Cheng, D.C.H.; McCoubrey, J.C.; Phillips, D.G.,
Critical Temperatures of Some Organic Cyclic Compounds,
Trans. Faraday Soc., 1962, 58, 224. [all data]
Kobe, Ravicz, et al., 1956
Kobe, K.A.; Ravicz, A.E.; Vohra, S.P.,
Critical Properties and Vapor Pressures of Some Ethers and Heterocyclic Compounds,
J. Chem. Eng. Data, 1956, 1, 50. [all data]
Hossenlopp and Scott, 1981
Hossenlopp, I.A.; Scott, D.W.,
Vapor heat capacities and enthalpies of vaporizaiton of six organic compounds,
J. Chem. Thermodyn., 1981, 13, 405-414. [all data]
Moiseev and Antonova, 1970
Moiseev, V.D.; Antonova, N.D.,
Zh. Fiz. Khim., 1970, 44, 11, 2912. [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]
Loras, Aucejo, et al., 2001
Loras, Sonia; Aucejo, Antonio; Montón, Juan B.; Wisniak, Jaime; Segura, Hugo,
Polyazeotropic Behavior in the Binary System 1,1,1,2,3,4,4,5,5,5-Decafluoropentane + Oxolane,
J. Chem. Eng. Data, 2001, 46, 6, 1351-1356, https://doi.org/10.1021/je0100793
. [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]
Borisov and Chugunova, 1976
Borisov, G.K.; Chugunova, S.G.,
Russ. J. Phys. Chem., 1976, 50, 1791. [all data]
Rivenq, 1975
Rivenq, F.,
Bull. Soc. Chim. Fr., 1975, 1, 2433. [all data]
Koizumi and Ouchi, 1970
Koizumi, E.; Ouchi, S.,
Nippon Kagaku Kaishi, 1970, 91, 5, 501. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Scott D.W., 1970
Scott D.W.,
Tetrahydrofuran: vibrational assignment, chemical thermodynamic properties, and vapor pressure,
J. Chem. Thermodyn., 1970, 2, 833-837. [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]
Klages and Möhler, 1948
Klages, Friedrich; Möhler, Klement,
Über das anomale osmotische Verhalten von Kettenmolekülen, VI. Mitteil.: Bestimmung der Dampfdruckerniedrigung von Polydepsiden,
Chem. Ber., 1948, 81, 5, 411-417, https://doi.org/10.1002/cber.19480810512
. [all data]
Cass, Fletcher, et al., 1958, 2
Cass, R.C.; Fletcher, S.E.; Mortimer, C.T.; Springall, H.D.; White, T.R.,
281. 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, https://doi.org/10.1039/jr9580001406
. [all data]
Lebedev, Rabinovich, et al., 1978, 2
Lebedev, B.V.; Rabinovich, I.B.; Milov, V.I.; Lityagov, V.Ya.,
Thermodynamic properties of tetrahydrofuran from 8 to 322 K,
J. Chem. Thermodyn., 1978, 10, 321-329. [all data]
Lebedev and Lityagov, 1977
Lebedev, B.V.; Lityagov, V.Ya.,
Calorimetric study of tetrahydrofuran and its polymerization in the temperature range 0-400°K,
Vysokomol. Soedin., 1977, A19, 2283-2290. [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]
Notes
Go To: Top, Phase change data, References
- Symbols used in this document:
Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature Vc Critical volume ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔfusH Enthalpy of fusion ΔfusS Entropy 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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