Thiophene, tetrahydro-, 1,1-dioxide
- Formula: C4H8O2S
- Molecular weight: 120.170
- IUPAC Standard InChIKey: HXJUTPCZVOIRIF-UHFFFAOYSA-N
- CAS Registry Number: 126-33-0
- 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. - Other names: Tetramethylene sulfone; Bondelane A; Bondolane A; Cyclic tetramethylene sulfone; Cyclotetramethylene sulfone; Sulfolan; Sulfolane; Sulpholane; Tetrahydrothiophene dioxide; Tetrahydrothiophene 1,1-dioxide; Thiacyclopentane dioxide; Thiophan sulfone; Thiophane dioxide; 1,1-Dioxothiolan; Thiophene, 1,1-dioxide-tetrahydro-; Dihydrobutadiene sulfone; 1,1-Dioxide tetrahydrothiofuran; Dioxothiolan; Tetrahydothiophene-1,1-dioxide; Sulfalone; Sulphoxaline; Thiocyclopentane-1,1-dioxide; Thiolane-1,1-dioxide; 1,1-Dioxidetetrahydrothiophene; 2,3,4,5-Tetrahydrothiophene-1,1-dioxide; Dihydrobutadiene sulphone; Tetrahydrothiofen-1,1-dioxid; Thiophane 1,1-dioxide; NSC 46443
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Phase change data
Go To: Top, 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 558. | K | N/A | Lee, 1986 | Uncertainty assigned by TRC = 3. K; TRC |
Tboil | 561.2 | K | N/A | Tripathi, RajaRam, et al., 1975 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 301.0 | K | N/A | Lee, 1986 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 301.6 | K | N/A | Jannelli and Pansini, 1985 | Uncertainty assigned by TRC = 0.1 K; TRC |
Tfus | 301.61 | K | N/A | Jannelli and Pansini, 1985, 2 | Uncertainty assigned by TRC = 0.1 K; TRC |
Tfus | 301.61 | K | N/A | Lopez, Jannelli, et al., 1983 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 301.60 | K | N/A | Sacco and Jannelli, 1972 | Uncertainty assigned by TRC = 0.1 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 855. | K | N/A | Steele, Chirico, et al., 1997 | Uncertainty assigned by TRC = 5. K; derived from fit of obs. vapor pressure; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 71.95 | atm | N/A | Steele, Chirico, et al., 1997 | Uncertainty assigned by TRC = 2.96 atm; derived from fit of obs. vapor pressure; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 2.996 | mol/l | N/A | Steele, Chirico, et al., 1997 | Uncertainty assigned by TRC = 0.12 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 16.5 ± 0.33 | kcal/mol | C | Morais, Matos, et al., 2004 | AC |
ΔvapH° | 16.2 ± 0.2 | kcal/mol | EB | Steele, Chirico, et al., 1997, 2 | Based on data from 424. to 542. K.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
13.9 | 413. | TGA | Al-Najjar and Al-Sammerrai, 2007 | Based on data from 373. to 453. K.; AC |
14.1 | 438. | N/A | Dykyj, Svoboda, et al., 1999 | Based on data from 423. to 529. K.; AC |
12.8 | 379. | N/A | Dykyj, Svoboda, et al., 1999 | Based on data from 364. to 529. K.; AC |
7.41 | 315. | A | Stephenson and Malanowski, 1987 | Based on data from 303. to 328. K.; AC |
14.0 | 428. | A | Stephenson and Malanowski, 1987 | Based on data from 413. to 558. K.; AC |
13.0 | 380. | N/A | Shcherbina, Kaporovskii, et al., 1984 | Based on data from 360. to 400. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
0.327 | 301.7 | Ahlers, Lohmann, et al., 1999 | AC |
0.342 | 301.6 | Domanska, Moollan, et al., 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
4.434 | 288.6 | Domanska, Moollan, et al., 1996, 2 | CAL |
1.13 | 301.6 |
Mass spectrum (electron ionization)
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
Spectrum
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Additional Data
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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- 804 |
NIST MS number | 227911 |
References
Go To: Top, 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.
Lee, 1986
Lee, F.-M.,
Use of Organic Sulfones as the Extractive Distillation SOlvent for Aromatic Recovery,
Ind. Eng. Chem. Process Des. Dev., 1986, 25, 949-57. [all data]
Tripathi, RajaRam, et al., 1975
Tripathi, R.P.; RajaRam, A.; Bhimeshwararao, P.,
Liquid-liquid equilibria in ternary system toluene + n-heptane + sulfolane,
J. Chem. Eng. Data, 1975, 20, 261-4. [all data]
Jannelli and Pansini, 1985
Jannelli, L.; Pansini, M.,
Thermodynamic properties of dilute solutions of C2-C6 n-alkanoic acids in sulfolane,
J. Chem. Eng. Data, 1985, 30, 349. [all data]
Jannelli and Pansini, 1985, 2
Jannelli, L.; Pansini, M.,
Solid-Liquid Phase Diagram and Excess Propertiers at 303.16 and 313.16 K of Dimethyl Sulfoxide (1) + Sulfolane (2) Binary System,
J. Chem. Eng. Data, 1985, 30, 428. [all data]
Lopez, Jannelli, et al., 1983
Lopez, A.; Jannelli, L.; Pansini, M.,
Thermodynamic and Physical Properties of Binary Systems Involving Sulfolane + 2-Methylpropionitrile and Sulfolane + 2,2-Dimethylpropionitrile dimethylpropionitrile.,
J. Chem. Eng. Data, 1983, 28, 176. [all data]
Sacco and Jannelli, 1972
Sacco, A.; Jannelli, L.,
Thermodynamic behavior of binary mixtures involving sulfolane: I excess volumes of sulfolane with benzene, carbon tetrachloride, and dioxan,
J. Chem. Thermodyn., 1972, 4, 191-7. [all data]
Steele, Chirico, et al., 1997
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.,
Vapor Pressure, Heat Capacity, and Density along the Saturted Line, Measurements for Cyclohexanol, 2-Cyclohexen-1-one, 1,2-Dichloropropane, 1,4-Di-tert-butylbenzene, (±)-2-Ethylhexanoic Acid, 1-(m,
J. Chem. Eng. Data, 1997, 42, 1021-36. [all data]
Morais, Matos, et al., 2004
Morais, Victor M.F.; Matos, M. Agostinha R.; Miranda, Margarida S.; Liebman, Joel F.,
Surprises with strain energy and sulpholane (tetrahydrothiophene 1,1-dioxide): a combined experimental and theoretical investigation,
Molecular Physics, 2004, 102, 5, 525-530, https://doi.org/10.1080/002689710410001671558
. [all data]
Steele, Chirico, et al., 1997, 2
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.,
Vapor Pressure, Heat Capacity, and Density along the Saturation Line, Measurements for Cyclohexanol, 2-Cyclohexen-1-one, 1,2-Dichloropropane, 1,4-Di- tert -butylbenzene, (±)-2-Ethylhexanoic Acid, 2-(Methylamino)ethanol, Perfluoro- n -heptane, and Sulfolane,
J. Chem. Eng. Data, 1997, 42, 6, 1021-1036, https://doi.org/10.1021/je9701036
. [all data]
Al-Najjar and Al-Sammerrai, 2007
Al-Najjar, Hazim; Al-Sammerrai, Dhoaib,
Thermogravimetric determination of the heat of vaporization of some highly polar solvents,
J. Chem. Technol. Biotechnol., 2007, 37, 3, 145-152, https://doi.org/10.1002/jctb.280370302
. [all data]
Dykyj, Svoboda, et al., 1999
Dykyj, J.; Svoboda, J.; Wilhoit, R.C.; Frenkel, M.L.; Hall, K.R.,
Vapor Pressure of Chemicals: Part A. Vapor Pressure and Antoine Constants for Hydrocarbons and Sulfur, Selenium, Tellurium and Hydrogen Containing Organic Compounds, Springer, Berlin, 1999, 373. [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]
Shcherbina, Kaporovskii, et al., 1984
Shcherbina, A.E.; Kaporovskii, L.M.; Shcherbina, E.A.,
Zh. Prikl. Khim. (Leningrad), 1984, 57, 1910. [all data]
Ahlers, Lohmann, et al., 1999
Ahlers, Jens; Lohmann, Jürgen; Gmehling, Jürgen,
Binary Solid-Liquid Equilibria of Organic Systems Containing Different Amides and Sulfolane,
J. Chem. Eng. Data, 1999, 44, 4, 727-730, https://doi.org/10.1021/je9802975
. [all data]
Domanska, Moollan, et al., 1996
Domanska, Urszula; Moollan, Warren C.; Letcher, Trevor M.,
Solubility of Sulfolane in Selected Organic Solvents,
J. Chem. Eng. Data, 1996, 41, 2, 261-265, https://doi.org/10.1021/je950236w
. [all data]
Domanska, Moollan, et al., 1996, 2
Domanska, U.; Moollan, W.C.; Letcher, T.M.,
Solubility of Sulfolane in Selected Organic Solvents,
J. Chem. Eng. Data, 1996, 41, 2, 261, https://doi.org/10.1021/je950236w
. [all data]
Notes
Go To: Top, Phase change data, Mass spectrum (electron ionization), References
- Symbols used in this document:
Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion 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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