Ethane, 1,1-dichloro-
- Formula: C2H4Cl2
- Molecular weight: 98.959
- IUPAC Standard InChIKey: SCYULBFZEHDVBN-UHFFFAOYSA-N
- CAS Registry Number: 75-34-3
- 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: Ethylidene chloride; Ethylidene dichloride; 1,1-Dichloroethane; CH3CHCl2; Dichloromethylmethane; Aethylidenchlorid; Chlorure d'ethylidene; Cloruro di etilidene; 1,1-Dichloorethaan; 1,1-Dichloraethan; 1,1-Dichlorethane; 1,1-Dicloroetano; NCI-C04535; Rcra waste number U076; UN 2362; Assymmetrical Dichloroethane
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -31.67 ± 0.84 | kcal/mol | Review | Manion, 2002 | employed hydrochlorination equilibrium measurements of Levanova, Treger, et al., 1976 with increased uncertainty to reflect other data; DRB |
ΔfH°gas | -30.50 ± 0.27 | kcal/mol | Chyd | Lacher, Amador, et al., 1967 | Reanalyzed by Cox and Pilcher, 1970, Original value = -30.7 ± 0.27 kcal/mol; At 250C; ALS |
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:
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 | -39.03 ± 0.84 | kcal/mol | Review | Manion, 2002 | derived from recommended ΔfHgas° and ΔvapH°; DRB |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -298.0 ± 2.0 | kcal/mol | Ccb | Smith, Bjellerup, et al., 1953 | Reanalyzed by Cox and Pilcher, 1970, Original value = -297. ± 2. kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 50.609 | cal/mol*K | N/A | Li and Pitzer, 1956 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
30.179 | 298.15 | Li and Pitzer, 1956 | T = 14 to 294 K.; DH |
30.40 | 298. | Kurbatov, 1948 | T = -51 to 55°C, mean Cp, four temperatures.; DH |
28.90 | 298. | von Reis, 1881 | T = 287 to 344 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
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 330.5 ± 0.5 | K | AVG | N/A | Average of 18 out of 19 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 174. | K | N/A | Van de Vloed, 1939 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tfus | 176.7 | K | N/A | Timmermans, 1935 | Uncertainty assigned by TRC = 1. K; TRC |
Tfus | 176.5 | K | N/A | Timmermans, 1911 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 176.18 | K | N/A | Li and Pitzer, 1956 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 523.4 | K | N/A | Garcia-Sanchez and Trejo Rodriguez, 1987 | Uncertainty assigned by TRC = 0.2 K; Visual, mean of four samples. R150a; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 49.95 | atm | N/A | Garcia-Sanchez and Trejo Rodriguez, 1987 | Uncertainty assigned by TRC = 0.099 atm; Visual, mean of four samples. R150a; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 7.354 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 7.37 ± 0.02 | kcal/mol | Review | Manion, 2002 | weighted average of several measurements plus a correction for non-ideality; DRB |
ΔvapH° | 7.318 ± 0.033 | kcal/mol | C | Laynez and Wadso, 1972 | ALS |
ΔvapH° | 7.31 ± 0.02 | kcal/mol | C | Laynez, Wadsö, et al., 1972 | AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
7.4092 | 293. | N/A | Li and Pitzer, 1956 | P = 30.32 kPA; DH |
6.895 | 330.4 | N/A | Majer and Svoboda, 1985 | |
8.01 | 336. | N/A | Garcia-Sanchez and Trejo, 1987 | Based on data from 326. to 345. K.; AC |
6.98 | 338. | A | Stephenson and Malanowski, 1987 | Based on data from 323. to 535. K.; AC |
6.74 | 378. | A | Stephenson and Malanowski, 1987 | Based on data from 363. to 535. K.; AC |
7.4 ± 7.0 | 293. | V | Li and Pitzerk, 1956 | ALS |
7.62 | 275. | N/A | Li and Pitzer, 1956 | Based on data from 234. to 290. K.; AC |
8.22 | 228. | N/A | Stull, 1947 | Based on data from 213. to 330. K.; AC |
Entropy of vaporization
ΔvapS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
25.289 | 293. | Li and Pitzer, 1956 | P; DH |
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 |
---|---|---|---|---|---|
234.38 to 290.76 | 4.18860 | 1215.342 | -40.26 | Li and Pitzer, 1956 | Coefficents calculated by NIST from author's data. |
212.5 to 330.6 | 4.21582 | 1229.158 | -39.204 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
1.881 | 176.18 | Li and Pitzer, 1956 | DH |
1.88 | 176.2 | Acree, 1991 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
10.68 | 176.18 | Li and Pitzer, 1956 | 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: 2H2 + C2H4Cl2 = C2H6 + 2HCl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -33.66 ± 0.25 | kcal/mol | Chyd | Lacher, Amador, et al., 1967 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -34.65 ± 0.12 kcal/mol; At 250C |
By formula: C2H4Cl2 = C2H3Cl + HCl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 17.8 | kcal/mol | Eqk | Levanova, Bushneva, et al., 1979 | liquid phase |
ΔrH° | 14.8 | kcal/mol | Eqk | Levanova, Bushneva, et al., 1979 | gas phase |
By formula: 2C2H4BrCl = C2H4Br2 + C2H4Cl2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1.9 ± 0.1 | kcal/mol | Eqk | Busheva, Levanova, et al., 1980 | gas phase; Dehydrohalogenation |
By formula: C2H4Cl2 = C2H4Cl2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -2.30 ± 0.33 | kcal/mol | Eqk | Rozhnov, 1968 | gas phase; Heat of isomerization at 385 K |
By formula: C2H3Cl + HCl = C2H4Cl2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -22.15 | kcal/mol | Eqk | Levanova, Treger, et al., 1976 | gas phase |
Gas phase ion energetics 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 evaluated as indicated in comments:
L - Sharon G. Lias
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 11.04 ± 0.02 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
11.02 | PE | Berman, Anicich, et al., 1979 | LLK |
11.06 | PI | Berman, Anicich, et al., 1979 | LLK |
11.23 ± 0.02 | PE | Katsumata and Kimura, 1975 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H4Cl+ | 11.20 | ? | PI | Berman, Anicich, et al., 1979 | LLK |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References, Notes
Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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]
Levanova, Treger, et al., 1976
Levanova, S.V.; Treger, Yu.A.; Velichko, S.M.; Rozhnov, A.M.,
Equilibria in the reactions of vinyl chloride,
Russ. J. Phys. Chem. (Engl. Transl.), 1976, 50, 1148. [all data]
Lacher, Amador, et al., 1967
Lacher, J.R.; Amador, A.; Park, J.D.,
Reaction heats of organic compounds. Part 5.-Heats of hydrogenation of dichloromethane, 1,1- and 1,2-dichloroethane and 1,2-dichloropropane,
Trans. Faraday Soc., 1967, 63, 1608-1611. [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]
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]
Li and Pitzer, 1956
Li, J.C.M.; Pitzer, K.S.,
The thermodynamic properties of 1,1-dichloroethane: heat capacities from 14 to 294 K., heats of fusion and vaporization, vapor pressure and entropy of the ideal gas. The barrier to internal rotation,
J. Am. Chem. Soc., 1956, 78, 1077-1080. [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]
Van de Vloed, 1939
Van de Vloed, A.,
Bull. Soc. Chim. Belg., 1939, 48, 229. [all data]
Timmermans, 1935
Timmermans, J.,
Researches in Stoichiometry. I. The Heat of Fusion of Organic Compounds.,
Bull. Soc. Chim. Belg., 1935, 44, 17-40. [all data]
Timmermans, 1911
Timmermans, J.,
Researches on the freezing point of organic liquid compounds,
Bull. Soc. Chim. Belg., 1911, 25, 300. [all data]
Garcia-Sanchez and Trejo Rodriguez, 1987
Garcia-Sanchez, F.; Trejo Rodriguez, A.,
Vapor pressure and critical constants of 1,1-dichloroethane,
J. Chem. Thermodyn., 1987, 19, 359. [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]
Laynez and Wadso, 1972
Laynez, J.; Wadso, I.,
Enthalpies of vaporization of organic compounds. IX. Some halogen substituted hydrocarbons and esters,
Acta Chem. Scand., 1972, 26, 3148. [all data]
Laynez, Wadsö, et al., 1972
Laynez, José; Wadsö, Ingemar; Haug, Arne; Songstad, J.; Pilotti, Åke,
Enthalpies of Vaporization of Organic Compounds. IX. Some Halogen Substituted Hydrocarbons and Esters.,
Acta Chem. Scand., 1972, 26, 3148-3152, https://doi.org/10.3891/acta.chem.scand.26-3148
. [all data]
Garcia-Sanchez and Trejo, 1987
Garcia-Sanchez, Fernando; Trejo, Arturo,
Vapour pressure and critical constants of 1,1-dichloroethane,
The Journal of Chemical Thermodynamics, 1987, 19, 4, 359-361, https://doi.org/10.1016/0021-9614(87)90118-2
. [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]
Li and Pitzerk, 1956
Li, J.C.M.; Pitzerk, K.S.,
The thermodynamic properties of 1,1-dichloroethane: Heat capacities from 14 to 194°K., heats of fusion and vaporization, vapor pressure and entropy of the ideal gas. The barrier to internal rotation,
J. Am. Chem. Soc., 1956, 78, 1077-10. [all data]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [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]
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]
Busheva, Levanova, et al., 1980
Busheva, L.I.; Levanova, S.V.; Rodova, R.M.; Rozhnov, A.M.,
Thermocatalytic reactions of 1,1-bromochloroethane,
Russ. J. Phys. Chem. (Engl. Transl.), 1980, 54, 1403-1404. [all data]
Rozhnov, 1968
Rozhnov, A.M.,
Equilibrium of dichloroethane isomerization,
Neftekhimiya, 1968, 8, 431-434. [all data]
Berman, Anicich, et al., 1979
Berman, D.W.; Anicich, V.; Beauchamp, J.L.,
Stabilities of isomeric halonium ions C2H4X+ (X = Cl, Br) by photoionization mass spectrometry iand on cyclotron resonance spectroscopy. General considerations of the relative stabilities of cyclic and acyclic isomeric onium ions,
J. Am. Chem. Soc., 1979, 101, 1239. [all data]
Katsumata and Kimura, 1975
Katsumata, S.; Kimura, K.,
Photoelectron spectra and sum rule consideration. Effect of chlorine substitution on ionization energies for chloroethanes, chloroacetaldehydes and chloroacetyl chlorides,
J. Electron Spectrosc. Relat. Phenom., 1975, 6, 309. [all data]
Notes
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- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy Pc Critical pressure S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature 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 ΔvapS Entropy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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