Tetrachloroethylene
- Formula: C2Cl4
- Molecular weight: 165.833
- IUPAC Standard InChIKey: CYTYCFOTNPOANT-UHFFFAOYSA-N
- CAS Registry Number: 127-18-4
- 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: Ethene, tetrachloro-; Ethylene, tetrachloro-; Ankilostin; Antisal 1; Didakene; Ethylene tetrachloride; Fedal-Un; Nema; Perchlorethylene; Perchloroethylene; Perclene; PerSec; Tetlen; Tetracap; Tetrachlorethylene; Tetrachloroethene; Tetraguer; Tetraleno; Tetropil; 1,1,2,2-Tetrachloroethylene; C2Cl4; Carbon bichloride; Carbon dichloride; Czterochloroetylen; ENT 1,860; Nema, veterinary; NCI-C04580; Perawin; Perchloorethyleen, per; Perchloraethylen, per; Perchlorethylene, per; Percloroetilene; PERC; Tetrachlooretheen; Tetrachloraethen; Tetracloroetene; Tetralex; Antisol 1; Dow-per; Perchlor; Perclene D; Percosolve; PERK; Perklone; RCRA Waste Number U210; Tetravec; Tetroguer; UN 1897; Dilatin PT; 1,1,2,2-Tetrachloroethene; Freon 1110; Perclene TG; Perchloroethene; F 1110
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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 as indicated in comments:
DRB - Donald R. Burgess, Jr.
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 | -64. ± 4. | kJ/mol | Review | Manion, 2002 | derived from recommended ΔfHgas° and ΔvapH°; DRB |
ΔfH°liquid | -54.4 | kJ/mol | Cm | Kirkbride, 1956 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -830. ± 10. | kJ/mol | Ccb | Smith, Bjellerup, et al., 1953 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 240.6 | J/mol*K | N/A | Novoselova, Rabinovich, et al., 1986 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
147.16 | 298.15 | Wilhelm, Lainez, et al., 1989 | DH |
157.9 | 298.15 | Novoselova, Rabinovich, et al., 1986 | T = 6 to 300 K.; DH |
146.5 | 298.15 | Grolier, Inglese, et al., 1982 | T = 298.15 K. One data point given.; DH |
139.7 | 298. | Kurbatov, 1948 | T = 16 to 119°C, mean Cp two temperatures.; DH |
146.9 | 298. | von Reis, 1881 | T = 291 to 410 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
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 | 394.2 ± 0.4 | K | AVG | N/A | Average of 14 out of 15 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 250.97 | K | N/A | Dreisbach and Martin, 1949 | Uncertainty assigned by TRC = 0.05 K; TRC |
Tfus | 250.6 | K | N/A | Van de Vloed, 1939 | Uncertainty assigned by TRC = 0.6 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 250.81 | K | N/A | Novoselova, Rabinovich, et al., 1986, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 620. | K | N/A | Majer and Svoboda, 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 39.72 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 39.72 ± 0.05 | kJ/mol | Review | Manion, 2002 | weighted average of several measurements plus a correction for non-ideality; DRB |
ΔvapH° | 39.7 ± 0.1 | kJ/mol | C | Majer, Sváb, et al., 1980 | AC |
ΔvapH° | 39.7 ± 0.84 | kJ/mol | V | Mathews, 1926 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 34.7 ± 0.1 kJ/mol; ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
34.68 | 394.1 | N/A | Majer and Svoboda, 1985 | |
38.4 | 322. | N/A | Dejoz, Cruz Burguet, et al., 1995 | Based on data from 307. to 393. K.; AC |
38.7 | 325. | A | Stephenson and Malanowski, 1987 | Based on data from 310. to 393. K. See also Boublík and Aim, 1972.; AC |
38.9 | 315. | N/A | Polak, Murakami, et al., 1970 | Based on data from 300. to 380. K. See also Boublik, Fried, et al., 1984.; AC |
37.6 | 348. | N/A | Fried, Gallant, et al., 1967 | Based on data from 333. to 373. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
301.03 to 380.84 | 4.18056 | 1440.819 | -49.171 | Polak, Murakami, et al., 1970 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
10.880 | 250.81 | Novoselova, Rabinovich, et al., 1986 | DH |
10.88 | 250.8 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
43.38 | 250.81 | Novoselova, Rabinovich, et al., 1986 | DH |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
3.9 | 210. | Domalski and Hearing, 1996 | CAL |
43.38 | 250.8 |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.820 | 125. to 210. | crystaline, II | crystaline, I | Novoselova, Rabinovich, et al., 1986 | DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
5.26 | 125. to 210. | crystaline, II | crystaline, I | Novoselova, Rabinovich, et al., 1986 | DH |
Reaction thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics 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
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: C2HCl5 = C2Cl4 + HCl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 45.1 ± 4.5 | kJ/mol | Eqk | Levanova, Bushneva, et al., 1979 | liquid phase; GC |
ΔrH° | 39. | kJ/mol | Eqk | Levanova, Bushneva, et al., 1979 | gas phase |
By formula: C2Cl4 + Cl2 = C2Cl6
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -153.6 ± 2.5 | kJ/mol | Cm | Kirkbride, 1956 | liquid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -150. kJ/mol |
By formula: H2CaO2 + 2C2HCl5 = CaCl2 + 2C2Cl4 + 2H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -181.6 | kJ/mol | Cm | Kirkbride, 1956 | liquid phase |
By formula: C2Cl6 = C2Cl4 + Cl2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 132.6 ± 4.2 | kJ/mol | Eqk | Puyo, Balesdent, et al., 1963 | gas phase |
Gas phase ion energetics 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 evaluated as indicated in comments:
L - Sharon G. Lias
Data compiled as indicated in comments:
LL - Sharon G. Lias and Joel F. Liebman
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.326 ± 0.001 | eV | N/A | N/A | L |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.640 ± 0.030 | TDAs | Chen, Wiley, et al., 1994 | The experimental HOF of C2Cl4 has been questioned as being too positive: Curtiss, Raghavachari, et al., 7374,11CHA/DEN; B |
0.499990 | ECD | Wiley, Chen, et al., 1991 | B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.3256 ± 0.0006 | S | Williams and Cool, 1990 | LL |
9.51 | PE | Kimura, Katsumata, et al., 1981 | LLK |
9.34 | PE | Lake and Thompson, 1970 | RDSH |
9.32 ± 0.01 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
9.32 | PI | Bralsford, Harris, et al., 1960 | RDSH |
9.5 | PE | Von Niessen, Asbrink, et al., 1982 | Vertical value; LBLHLM |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CCl2+ | 14.7 | ? | EI | Shapiro and Lossing, 1968 | RDSH |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Manion, 2002
Manion, J.A.,
Evaluated Enthalpies of Formation of the Stable Closed Shell C1 and C2 Chlorinated Hydrocarbons,
J. Phys. Chem. Ref. Data, 2002, 31, 1, 123-172, https://doi.org/10.1063/1.1420703
. [all data]
Kirkbride, 1956
Kirkbride, F.W.,
The heats of chlorination of some hydrocarbons and their chloro-derivatives,
J. Appl. Chem., 1956, 6, 11-21. [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]
Novoselova, Rabinovich, et al., 1986
Novoselova, N.V.; Rabinovich, I.B.; Tsvetkova, L.Ya.; Moseeva, E.M.; Babinkov, A.G.,
Heat capacity and thermodynamic functions of tetrachloroethylene,
Zhur. Fiz. Khim., 1986, 60, 1627-1630. [all data]
Wilhelm, Lainez, et al., 1989
Wilhelm, E.; Lainez, A.; Grolier, J.-P.E.,
Thermodynamics of (a halogenated ethane or ethene + an n-alkane). VE and CpE of mixtures containing either 1,1,2,2-tetrachloroethane or tetrachloroethene,
Fluid Phase Equilib., 1989, 49, 233-250. [all data]
Grolier, Inglese, et al., 1982
Grolier, J.-P.E.; Inglese, A.; Wilhelm, E.,
Excess volumes and excess heat capacities of tetrachloroethene + cyclohexane, + methylcyclohexane, + benzene, and + toluene at 298.15 K,
J. Chem. Thermodynam., 1982, 14, 523-529. [all data]
Kurbatov, 1948
Kurbatov, V.Ya.,
Heat capacity of liquids. 2. Heat capacity and the temperature dependence of heat capacity from halogen derivatives of acylic hydrocarbons,
Zh. Obshch. Kim., 1948, 18, 372-389. [all data]
von Reis, 1881
von Reis, M.A.,
Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht,
Ann. Physik [3], 1881, 13, 447-464. [all data]
Dreisbach and Martin, 1949
Dreisbach, R.R.; Martin, R.A.,
Physical Data on Some Organic Compounds,
Ind. Eng. Chem., 1949, 41, 2875-8. [all data]
Van de Vloed, 1939
Van de Vloed, A.,
Bull. Soc. Chim. Belg., 1939, 48, 229. [all data]
Novoselova, Rabinovich, et al., 1986, 2
Novoselova, N.V.; Rabinovich, I.B.; Tsvetkova, L.Ya.; Moseeva, E.M.; Babinkov, A.G.,
Heat capacity and thermodynamic functions of tetrachloroethylene,
Zh. Fiz. Khim., 1986, 60, 1627-30. [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]
Majer, Sváb, et al., 1980
Majer, V.; Sváb, L.; Svoboda, V.,
Enthalpies of vaporization and cohesive energies for a group of chlorinated hydrocarbons,
The Journal of Chemical Thermodynamics, 1980, 12, 9, 843-847, https://doi.org/10.1016/0021-9614(80)90028-2
. [all data]
Mathews, 1926
Mathews, J.H.,
The accurate measurement of heats of vaporization of liquids,
J. Am. Chem. Soc., 1926, 48, 562-576. [all data]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]
Dejoz, Cruz Burguet, et al., 1995
Dejoz, Ana; Cruz Burguet, M.; Munoz, Rosa; Sanchotello, Margarita,
Isobaric Vapor-Liquid Equilibria of Tetrachloroethylene with 1-Butanol and 2-Butanol at 6 and 20 kPa,
J. Chem. Eng. Data, 1995, 40, 1, 290-292, https://doi.org/10.1021/je00017a064
. [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]
Boublík and Aim, 1972
Boublík, T.; Aim, K.,
Heats of vaporization of simple non-spherical molecule compounds,
Collect. Czech. Chem. Commun., 1972, 37, 11, 3513-3521, https://doi.org/10.1135/cccc19723513
. [all data]
Polak, Murakami, et al., 1970
Polak, Jiri; Murakami, Sachio; Lam, V.T.; Benson, George C.,
Excess enthalpy, volume, and Gibbs free energy of cyclopentane-tetrachloroethylene mixtures at 25.deg.,
J. Chem. Eng. Data, 1970, 15, 2, 323-328, https://doi.org/10.1021/je60045a041
. [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]
Fried, Gallant, et al., 1967
Fried, Vojtech; Gallant, Paul; Schneier, Gary B.,
Vapor-liquid equilibrium in the system pyridine-tetrachloroethylene,
J. Chem. Eng. Data, 1967, 12, 4, 504-508, https://doi.org/10.1021/je60035a011
. [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, Bushneva, et al., 1979
Levanova, s.V.; Bushneva, I.I.; Rodova, R.M.; Rozhnov, A.M.; Treger, Yu.A.; Aprelkin, A.S.,
Thermodynamic stability of chloroethanes in dehydrochlorination reactions,
J. Appl. Chem. USSR, 1979, 52, 1439-1442. [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]
Puyo, Balesdent, et al., 1963
Puyo, J.; Balesdent, D.; Niclause, M.; Dzierzynski, M.,
Etude analytique et thermodynamique de la pyrolyse de l'hexachloroethane en phase gazeuse.,
Compt. Rend., 1963, 256, 3471-3473. [all data]
Chen, Wiley, et al., 1994
Chen, E.C.M.; Wiley, J.R.; Batten, C.F.; Wentworth, W.E.,
Determination of the Electron Affinities of Molecules Using Negative Ion Mass Spectrometry,
J. Phys. Chem., 1994, 98, 1, 88, https://doi.org/10.1021/j100052a016
. [all data]
Curtiss, Raghavachari, et al., 7374
Curtiss, L.A.; Raghavachari, K.; Redfern, P.C.; Pople, J.A.,
Assesment of Gaussian-3 and density Functional Theories for a larger experimental test set, J. Chem. Phys. 112 (2000), 7374. [all data]
Wiley, Chen, et al., 1991
Wiley, J.R.; Chen, E.C.M.; Chen, E.S.D.; Richardson, P.; Reed, W.R.; Wentworth, W.E.,
The Determination of Absolute Electron Affinities of Chlorobenzenes, Chloronaphthalenes and Chlorinated Biphenyls from Reduction Potentials,
J. Electroanal. Chem. Interfac., 1991, 307, 1-2, 169, https://doi.org/10.1016/0022-0728(91)85546-2
. [all data]
Williams and Cool, 1990
Williams, B.A.; Cool, T.A.,
Multiphoton spectroscopy of Rydberg states of tetrachloroethylene,
J. Chem. Phys., 1990, 93, 1521. [all data]
Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S.,
Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules
in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]
Lake and Thompson, 1970
Lake, R.F.; Thompson, H.,
Photoelectron spectra of halogenated ethylenes,
Proc. Roy. Soc. (London), 1970, A315, 323. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]
Bralsford, Harris, et al., 1960
Bralsford, R.; Harris, P.V.; Price, W.C.,
The effect of fluorine on the electronic spectra and ionization potentials of molecules,
Proc. Roy. Soc. (London), 1960, A258, 459. [all data]
Von Niessen, Asbrink, et al., 1982
Von Niessen, W.; Asbrink, L.; Bieri, G.,
30.4 nm He(II) Photoelectron spectra of organic molecules. Part VI. Halogeno-compounds (C,H,X: X = Cl, Br, I),
J. Electron Spectrosc. Relat. Phenom., 1982, 26, 173. [all data]
Shapiro and Lossing, 1968
Shapiro, J.S.; Lossing, F.P.,
Free radicals by mass spectrometry. XXXVII. The ionization potential and heat of formation of dichlorocarbene,
J. Phys. Chem., 1968, 72, 1552. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid EA Electron affinity IE (evaluated) Recommended ionization energy S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature 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°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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