Propane, 2,2-dichloro-
- Formula: C3H6Cl2
- Molecular weight: 112.986
- IUPAC Standard InChI: InChI=1S/C3H6Cl2/c1-3(2,4)5/h1-2H3
- IUPAC Standard InChIKey: ZEOVXNVKXIPWMS-UHFFFAOYSA-N
- CAS Registry Number: 594-20-7
- 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: Dimethyldichloromethane; 2,2-Dichloropropane
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -176.7 | kJ/mol | Eqk | Shevtsova, Rozhnov, et al., 1970 | Heat of Dehydrochlorination at 392 K |
| ΔfH°gas | -173. ± 8.8 | kJ/mol | Ccb | Smith, Bjellerup, et al., 1953 | Heat of formation derived by Cox and Pilcher, 1970 |
Condensed 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | -206. ± 8.4 | kJ/mol | Ccb | Smith, Bjellerup, et al., 1953 | Heat of formation derived by Cox and Pilcher, 1970; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -1879.5 ± 8.4 | kJ/mol | Ccb | Smith, Bjellerup, et al., 1953 | Reanalyzed by Cox and Pilcher, 1970, Original value = -1875. ± 8. kJ/mol; ALS |
Constant pressure heat capacity of liquid
| Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 151.4 | 270. | Van Miltenburg, 1972 | T = 137 to 267 K.; DH |
Phase change 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:
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
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 342.4 ± 0.5 | K | AVG | N/A | Average of 7 values; Individual data points |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 240.2 | K | N/A | Silver and Rudman, 1970 | Crystal phase 1 phase; Uncertainty assigned by TRC = 1. K; Temp. for cryst. of liquid to C1 was 226.7 K; TRC |
| Tfus | 238.8 | K | N/A | Turkevich and Smyth, 1940 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.4 K; TRC |
| Tfus | 238.5 | K | N/A | Van de Vloed, 1939 | Uncertainty assigned by TRC = 0.6 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| Ttriple | 239.25 | K | N/A | van Miltenburg, 1972 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.05 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 32.1 | kJ/mol | A | Varushchenko, Loseva, et al., 1987 | Based on data from 295. to 340. K. See also Basarová and Svoboda, 1991.; AC |
| ΔvapH° | 33. ± 1. | kJ/mol | E | Smith, Bjellerup, et al., 1953 | Heat of formation derived by Cox and Pilcher, 1970; ALS |
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 33.2 | 282. | A | Stephenson and Malanowski, 1987 | Based on data from 267. to 378. K. See also Dykyj, 1970.; AC |
Enthalpy of fusion
| ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 10.0 | 239.6 | Kobashi and Oguni, 1999 | AC |
| 2.34 | 239.3 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
| ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 31.8 | 188. | Domalski and Hearing, 1996 | CAL |
| 9.62 | 239.3 |
Enthalpy of phase transition
| ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
|---|---|---|---|---|---|
| 5.979 | 188. | crystaline, II | crystaline, I | Van Miltenburg, 1972 | Temperature not certain; give explicitly as 184.8 K and in table as 188 K.; DH |
| 2.341 | 239.25 | crystaline, I | liquid | Van Miltenburg, 1972 | DH |
Entropy of phase transition
| ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
|---|---|---|---|---|---|
| 31.8 | 188. | crystaline, II | crystaline, I | Van Miltenburg, 1972 | Temperature; DH |
| 9.8 | 239.25 | crystaline, I | liquid | Van Miltenburg, 1972 | DH |
Reaction 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 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: C3H6Cl2 = C3H5Cl + HCl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 65.1 | kJ/mol | Eqk | Levanova, Rodova, et al., 1983 | liquid phase; Flow reactor |
| ΔrH° | 59.8 ± 0.8 | kJ/mol | Eqk | Shevtsova, Rozhnov, et al., 1970 | gas phase; Heat of Dehydrochlorination at 392 K |
2 =
+
By formula: 2C3H6BrCl = C3H6Br2 + C3H6Cl2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -1.3 | kJ/mol | Eqk | Levanova, Rodova, et al., 1983 | liquid phase; Flow reactor |
+
=
By formula: C3H5Cl + HCl = C3H6Cl2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 59.8 ± 0.8 | kJ/mol | Eqk | Shevtsova, Rozhnov, et al., 1970 | gas phase |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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.
Shevtsova, Rozhnov, et al., 1970
Shevtsova, L.A.; Rozhnov, A.M.; Andreevskii, D.N.,
Equilibrium Dehydrochlorination of 2,2-dichloropropane,
Russ. J. Phys. Chem. (Engl. Transl.), 1970, 44, 852-855. [all data]
Smith, Bjellerup, et al., 1953
Smith, L.; Bjellerup, L.; Krook, S.; Westermark, H.,
Heats of combustion of organic chloro compounds determined by the "quartz wool" method,
Acta Chem. Scand., 1953, 7, 65. [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]
Van Miltenburg, 1972
Van Miltenburg, J.C.,
Construction of an adiabatic calorimeter. Thermodynamic properties of standard n-heptane from 155 to 270K and of 2,2-dichloropropane from 135 to 270K,
J. Chem. Thermodynam., 1972, 4, 773-782. [all data]
Silver and Rudman, 1970
Silver, L.; Rudman, R.,
Polymorphism of the Crystalline Methylchloromethane Compounds. A Differential Scanning Calorimetric Study,
J. Phys. Chem., 1970, 74, 3134-9. [all data]
Turkevich and Smyth, 1940
Turkevich, A.; Smyth, C.P.,
Molecular Rotation and Polymorphism in the Methyl Chloromethanes,
J. Am. Chem. Soc., 1940, 62, 2468-74. [all data]
Van de Vloed, 1939
Van de Vloed, A.,
Bull. Soc. Chim. Belg., 1939, 48, 229. [all data]
van Miltenburg, 1972
van Miltenburg, J.C.,
Construction of an adiabatic calorimeter. Thermodynamic properties of stan- dard n-heptane from 155 to 270 K and of 2,2-dichloropropane from 135 to 270 K.,
J. Chem. Thermodyn., 1972, 4, 773-82. [all data]
Varushchenko, Loseva, et al., 1987
Varushchenko, R.M.; Loseva, O.L.; Druzhinina, A.I.,
Zh. Fiz. Khim., 1987, 61, 31. [all data]
Basarová and Svoboda, 1991
Basarová, Pavlína; Svoboda, Václav,
Calculation of heats of vaporization of halogenated hydrocarbons from saturated vapour pressure data,
Fluid Phase Equilibria, 1991, 68, 13-34, https://doi.org/10.1016/0378-3812(91)85008-I
. [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, 1970
Dykyj, J.,
Petrochemica, 1970, 10, 2, 51. [all data]
Kobashi and Oguni, 1999
Kobashi, Kazuhisa; Oguni, Masaharu,
Thermodynamic Consideration on a Series of Compounds (CH 3 ) n CCl 4- n : Correlation between Molecular Sphericity, Configurational Order/Disorder, and Molecular Packing in Plastically Crystalline and Liquid Phases,
J. Phys. Chem. B, 1999, 103, 36, 7687-7694, https://doi.org/10.1021/jp990578z
. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Levanova, Rodova, et al., 1983
Levanova, S.V.; Rodova, R.M.; Tereshkina, T.P.; Zabrodina, T.I.,
Thermocatalytic reactions of bromochloropropanes,
Russ. J. Phys. Chem. (Engl. Transl.), 1983, 57, 1142-1146. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition 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 ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrH° Enthalpy of reaction at standard conditions 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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