Propane, 2,2-dichloro-
- Formula: C3H6Cl2
- Molecular weight: 112.986
- 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
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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
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 |
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 |
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 |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
- Not specified, most likely a prism, grating, or hybrid spectrometer.; (NO SPECTRUM, ONLY SCANNED IMAGE IS AVAILABLE)
- Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm-1 resolution
- SOLUTION (10% IN CCl4 FOR 3800-1333, AND 10% IN CS2 FOR 1333-400 CM-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
Mass spectrum (electron ionization)
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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: 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-4425 |
NIST MS number | 229628 |
Gas Chromatography
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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: 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 | Petrocol DH | 602. | White, Hackett, et al., 1992 | 100. m/0.25 mm/0.5 μm, He, 1. K/min; Tstart: 30. C; Tend: 220. C |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | Apiezon L | 130. | 619. | Arruda, Junkes, et al., 2008 |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 605. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
Capillary | SE-54 | 584. | Huang, Liang, et al., 1996 | 36. m/0.25 mm/0.25 μm, 5. K/min; Tstart: 35. C; Tend: 240. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxanes | 605. | Zenkevich, 2003 | Program: not specified |
Capillary | Methyl Silicone | 605. | Zenkevich, 2001 | Program: not specified |
Capillary | Polydimethyl siloxanes | 598. | Zenkevich, 1998 | Program: not specified |
Capillary | DB-5 | 608. | Sorimachi, Tanabe, et al., 1995 | He; Column length: 30. m; Program: not specified |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 604. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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]
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]
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]
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]
White, Hackett, et al., 1992
White, C.M.; Hackett, J.; Anderson, R.R.; Kail, S.; Spock, P.S.,
Linear temperature programmed retention indices of gasoline range hydrocarbons and chlorinated hydrocarbons on cross-linked polydimethylsiloxane,
J. Hi. Res. Chromatogr., 1992, 15, 2, 105-120, https://doi.org/10.1002/jhrc.1240150211
. [all data]
Arruda, Junkes, et al., 2008
Arruda, A.C.S.; Junkes, B. da.S.; Souza, E.S.; Yunes, R.A.; Heizen, V.E.F.,
Semi-Emlirical Topological Index to Predict Properties of Halogenated Aliphatic Compounds,
J. Chemometrics, 2008, 22, 3-4, 186-194, https://doi.org/10.1002/cem.1121
. [all data]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Huang, Liang, et al., 1996
Huang, C.; Liang, H.; Han, S.,
The analysis of organic compounds in waste water by gas extraction/thermal desorption/gas chromatography-mass spectrometry,
Chin. J. Chromatogr., 1996, 14, 6, 421-424. [all data]
Zenkevich, 2003
Zenkevich, I.G.,
Criteria for Evaluation of Elution Order of Isomeric Organic Compounds,
Zh. Phys. Khim. (Rus.), 2003, 77, 1, 92-98. [all data]
Zenkevich, 2001
Zenkevich, I.G.,
Interpretation of Gas Chromatographic Retention Indices in estimation of Structures of Isomeric Products of Radical Chlorinating of Alkyl Arenes,
Zh. Org. Khim., 2001, 37, 2, 283-293. [all data]
Zenkevich, 1998
Zenkevich, I.G.,
The Principle of Structural Analogy in the Calculation of Gas Chromatographic Retention Indices using Physico-Chemical Constants of Organic Compounds,
Zh. Anal. Khim. (Rus.), 1998, 53, 1, 43-49. [all data]
Sorimachi, Tanabe, et al., 1995
Sorimachi, J.; Tanabe, A.; Mitobe, H.; Kuniaki, K.; Masaaki, S.,
Programmed temperature retention indices for volatile organic compounds on headspace GC/MS analysis,
Niigata-ken Eisei Kogai Kenkyusho Nenpo, 1995, 11, 75-79. [all data]
Waggott and Davies, 1984
Waggott, A.; Davies, I.W.,
Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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 ΔfH°gas Enthalpy of formation of gas 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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