1,2-Ethanediol
- Formula: C2H6O2
- Molecular weight: 62.0678
- IUPAC Standard InChI: InChI=1S/C2H6O2/c3-1-2-4/h3-4H,1-2H2
- IUPAC Standard InChIKey: LYCAIKOWRPUZTN-UHFFFAOYSA-N
- CAS Registry Number: 107-21-1
- 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. - Species with the same structure:
- Other names: Ethylene glycol; Ethylene alcohol; Glycol; Glycol alcohol; Lutrol 9; Macrogol 400 BPC; Monoethylene glycol; Ramp; Tescol; 1,2-Dihydroxyethane; 2-Hydroxyethanol; HOCH2CH2OH; Aethylenglykol; Ethane-1,2-diol; Fridex; MEG 100; 1,2-Ethandiol; Ucar 17; Dowtherm SR 1; Norkool; Zerex; Ilexan E; 1,2-Ethylene glycol; 146AR; Ethylene dihydrate; NSC 93876; Union Carbide XL 54 Type I De-icing Fluid; Dihydroxyethane; Ethanediol; Ethylene gycol; Glygen; Athylenglykol; M.e.g.; Aliphatic diol
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -94.26 ± 0.67 | kcal/mol | Ccr | Knauth and Sabbah, 1990 | see Knauth and Sabbah, 1989; ALS |
| ΔfH°gas | -92.7 ± 0.4 | kcal/mol | Ccb | Gardner and Hussain, 1972 | ALS |
| ΔfH°gas | -93.28 | kcal/mol | N/A | McClaine, 1947 | Value computed using ΔfHliquid° value of -455.9 kj/mol from McClaine, 1947 and ΔvapH° value of 65.6 kj/mol from Knauth and Sabbah, 1990.; DRB |
| ΔfH°gas | -93.04 | kcal/mol | N/A | Parks, West, et al., 1946 | Value computed using ΔfHliquid° value of -454.9±0.3 kj/mol from Parks, West, et al., 1946 and ΔvapH° value of 65.6 kj/mol from Knauth and Sabbah, 1990.; DRB |
| ΔfH°gas | -92.61 | kcal/mol | N/A | Moureu and Dode, 1937 | Value computed using ΔfHliquid° value of -453.1±1.2 kj/mol from Moureu and Dode, 1937 and ΔvapH° value of 65.6 kj/mol from Knauth and Sabbah, 1990.; DRB |
| Quantity | Value | Units | Method | Reference | Comment |
| S°gas | 74.532 | cal/mol*K | N/A | Chao J., 1986 | Other third-law entropy values at 298.15 K known from literature are 284.5 [ Buckley P., 1967], 312.5 [ Stull D.R., 1969], and 315.47(5.36) J/mol*K [ Yeh T.-S., 1994].; GT |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 14.29 | 200. | Yeh T.-S., 1994 | Other statistically calculated values of entropy at 298.15 K (274.76 [ Buckley P., 1967], 293.76 [ Frei H., 1977], 303.8 [ Chao J., 1986], and 323.55 J/mol*K [ Dyatkina M.E., 1954]) are in worse agreement with third-law entropy value.; GT |
| 18.64 | 298.15 | ||
| 18.74 | 300. | ||
| 23.42 | 400. | ||
| 27.161 | 500. | ||
| 30.031 | 600. | ||
| 32.321 | 700. | ||
| 34.240 | 800. | ||
| 35.911 | 900. | ||
| 37.380 | 1000. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry 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 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 | -109.9 ± 0.67 | kcal/mol | Ccr | Knauth and Sabbah, 1990 | see Knauth and Sabbah, 1989; ALS |
| ΔfH°liquid | -108.9 ± 0.2 | kcal/mol | Ccb | Gardner and Hussain, 1972 | ALS |
| ΔfH°liquid | -108.95 | kcal/mol | Ccb | McClaine, 1947 | ALS |
| ΔfH°liquid | -108.73 ± 0.07 | kcal/mol | Ccb | Parks, West, et al., 1946 | ALS |
| ΔfH°liquid | -108.30 ± 0.29 | kcal/mol | Ccb | Moureu and Dode, 1937 | Reanalyzed by Cox and Pilcher, 1970, Original value = -108.1 kcal/mol; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -285. ± 2. | kcal/mol | AVG | N/A | Average of 7 values; Individual data points |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 39.89 | cal/mol*K | N/A | Parks, Kelley, et al., 1929 | Extrapolation below 90 K, 8.2 cal/mol*K. Revision of previous data.; DH |
| S°liquid | 42.90 | cal/mol*K | N/A | Parks and Kelley, 1925 | Extrapolation below 90 K, 11.46 cal/mol*K.; DH |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 35.80 | 298. | Zaripov, 1982 | T = 298, 323, 363 K.; DH |
| 35.68 | 298. | Stephens and Tamplin, 1979 | T = 273 to 493 K.; DH |
| 35.76 | 298.15 | Murthy and Subrahmanyam, 1977 | DH |
| 34.70 | 303. | Kawaizumi, Otake, et al., 1972 | DH |
| 35.99 | 301.2 | Paz Andrade, Paz, et al., 1970 | T = 28, 40°C.; DH |
| 35.930 | 298.15 | Nikolaev and Rabinovich, 1967 | T = 80 to 300 K.; DH |
| 35.21 | 298. | Tungusov and Mishchenko, 1965 | DH |
| 35.581 | 298. | Rabinovich and Nikolaev, 1962 | T = 10 to 55°C.; DH |
| 34.80 | 293.4 | Neiman and Kurlyankin, 1932 | T = 20.2 to 78.4°C. Value is unsmoothed experimental datum.; DH |
| 35.71 | 293.0 | Parks and Kelley, 1925 | T = 88 to 293 K. Value is unsmoothed experimental datum.; DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase 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 as indicated in comments:
B - John E. Bartmess
ALS - 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
( •
) +
= (
• 2
)
By formula: (Cl- • C2H6O2) + C2H6O2 = (Cl- • 2C2H6O2)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 15.9 ± 1.2 | kcal/mol | TDAs | Zhang, Beglinger, et al., 1995 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 9.3 ± 1.0 | kcal/mol | TDAs | Zhang, Beglinger, et al., 1995 | gas phase; B |
+
= (
•
)
By formula: Cl- + C2H6O2 = (Cl- • C2H6O2)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 25.3 ± 1.0 | kcal/mol | TDAs | Zhang, Beglinger, et al., 1995 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 16.6 ± 1.0 | kcal/mol | TDAs | Zhang, Beglinger, et al., 1995 | gas phase; B |
C2H5O2- + =
By formula: C2H5O2- + H+ = C2H6O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 365.1 ± 2.5 | kcal/mol | G+TS | Crowder and Bartmess, 1993 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 360.9 ± 2.0 | kcal/mol | IMRE | Crowder and Bartmess, 1993 | gas phase; B |
+
=
+
By formula: C2H6O2 + C3H6O = C5H10O2 + H2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -2.4 | kcal/mol | Eqk | Anteunis and Rommelaere, 1970 | liquid phase; ALS |
+
=
+
By formula: C2H6O2 + HNO3 = C2H5NO4 + H2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -1.9 | kcal/mol | Cm | Tsvetkov, Sopin, et al., 1986 | liquid phase; ALS |
+
= C2H6NO3-
By formula: NO- + C2H6O2 = C2H6NO3-
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 27.00 | kcal/mol | N/A | Hendricks, de Clercq, et al., 2002 | gas phase; B |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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.
Knauth and Sabbah, 1990
Knauth, P.; Sabbah, R.,
Energetics of intra- and intermolecular bonds in ω-alkanediols (II) Thermochemical study of 1,2-ethanediol, 1,3-propanediol, 1,4-butanediol, and 1,5-pentanediol at 298.15K,
Struct. Chem., 1990, 1, 43-46. [all data]
Knauth and Sabbah, 1989
Knauth, P.; Sabbah, R.,
Combustion calorimetry on milligram samples of liquid substances with a CRMT rocking bomb calorimeter. Application to the study of ω-alkanediol at 298.15 K,
J. Chem. Thermodyn., 1989, 21, 203-210. [all data]
Gardner and Hussain, 1972
Gardner, P.J.; Hussain, K.S.,
The standard enthalpies of formation of some aliphatic diols,
J. Chem. Thermodyn., 1972, 4, 819-827. [all data]
McClaine, 1947
McClaine, L.A.,
Thermodynamic data for some compounds containing carbon, hydrogen and oxygen, Ph.D. Thesis for Stanford University, 1947, 1-57. [all data]
Parks, West, et al., 1946
Parks, G.S.; West, T.J.; Naylor, B.F.; Fujii, P.S.; McClaine, L.A.,
Thermal data on organic compounds. XXIII. Modern combustion data for fourteen hydrocarbons and five polyhydroxy alcohols,
J. Am. Chem. Soc., 1946, 68, 2524-2527. [all data]
Moureu and Dode, 1937
Moureu, H.; Dode, M.,
Chaleurs de formation de l'oxyde d'ethylene, de l'ethanediol et de quelques homologues,
Bull. Soc. Chim. France, 1937, 4, 637-647. [all data]
Chao J., 1986
Chao J.,
Thermodynamic properties of key organic oxygen compounds in the carbon range C1 to C4. Part 2. Ideal gas properties,
J. Phys. Chem. Ref. Data, 1986, 15, 1369-1436. [all data]
Buckley P., 1967
Buckley P.,
Infrared studies on rotational isomerism. I. Ethylene glycol,
Can. J. Chem., 1967, 45, 397-407. [all data]
Stull D.R., 1969
Stull D.R., Jr.,
The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969. [all data]
Yeh T.-S., 1994
Yeh T.-S.,
Global conformational analysis of 1,2-ethanediol,
J. Phys. Chem., 1994, 98, 8921-8929. [all data]
Frei H., 1977
Frei H.,
Ethylene glycol: infrared spectra, ab initio calculation, vibrational analysis and conformations of 5 matrix isolated isotopic modifications,
Chem. Phys., 1977, 25, 271-298. [all data]
Dyatkina M.E., 1954
Dyatkina M.E.,
Thermodynamic functions of normal alcohols (propanol, butanol, ethylene glycol),
Zh. Fiz. Khim., 1954, 28, 377. [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]
Parks, Kelley, et al., 1929
Parks, G.S.; Kelley, K.K.; Huffman, H.M.,
Thermal data on organic compounds. V. A revision of the entropies and free energies of nineteen organic compounds,
J. Am. Chem. Soc., 1929, 51, 1969-1973. [all data]
Parks and Kelley, 1925
Parks, G.S.; Kelley, K.K.,
Thermal data on organic compounds. II. The heat capacities of five organic compounds. The entropies and free energies of some homologous series of aliphatic compounds,
J. Am. Chem. Soc., 1925, 47, 2089-2097. [all data]
Zaripov, 1982
Zaripov, Z.I.,
Experimental study of the isobaric heat capacity of liquid organic compounds with molecular weights of up to 4000 a.e.m., 1982, Teplomassoobmen Teplofiz. [all data]
Stephens and Tamplin, 1979
Stephens, M.A.; Tamplin, W.S.,
Saturated liquid specific heats of ethylene glycol homologues,
J. Chem. Eng. Data, 1979, 24, 81-82. [all data]
Murthy and Subrahmanyam, 1977
Murthy, N.M.; Subrahmanyam, S.V.,
Behaviour of excess heat capacity of aqueous non-electrolytes,
Indian J. Pure Appl. Phys., 1977, 15, 485-489. [all data]
Kawaizumi, Otake, et al., 1972
Kawaizumi, F.; Otake, T.; Nomura, H.; Miyahara, Y.,
Heat capacities of aqueous solutions of ethylene glycol, propylene glycol and 1,3-butanediol,
Nippon Kagaku. Kaishi, 1972, 1972, 1733-1776. [all data]
Paz Andrade, Paz, et al., 1970
Paz Andrade, M.I.; Paz, J.M.; Recacho, E.,
Contribucion a la microcalorimetria de los calores especificos de solidos y liquidos,
An. Quim., 1970, 66, 961-967. [all data]
Nikolaev and Rabinovich, 1967
Nikolaev, P.N.; Rabinovich, I.B.,
Heat capacity of ethylene glycol and ethylene deuteroglycol in the temperature range 80-300K,
Zhur. Fiz. Khim., 1967, 41, 2191-2194. [all data]
Tungusov and Mishchenko, 1965
Tungusov, V.P.; Mishchenko, K.P.,
Specific heat of pure ethylene glycol and solution of NaI and KI in ethylene glycol at 25°C,
Zhur. Fiz. Khim., 1965, 39, 2968-2972. [all data]
Rabinovich and Nikolaev, 1962
Rabinovich, I.B.; Nikolaev, P.N.,
Isotopic effect in the specific heat of some deutero compounds,
Dokl. Akad. Nauk, 1962, SSSR 142, 1335-1338. [all data]
Neiman and Kurlyankin, 1932
Neiman, M.B.; Kurlyankin, I.A.,
Thermodynamic studies of solutions. II. Study of the thermodynamics of aqueous solutions of ethylene glycol at different temperatures,
Zhur. Obshch. Khim., 1932, 2, 318-321. [all data]
Zhang, Beglinger, et al., 1995
Zhang, W.; Beglinger, C.; Stone, J.A.,
High-pressure mass spectrometric study of the gas-phase association of Cl- with alpha,omega-diols,
J. Phys. Chem., 1995, 99, 30, 11673, https://doi.org/10.1021/j100030a009
. [all data]
Crowder and Bartmess, 1993
Crowder, C.; Bartmess, J.,
The Gas Phase Acidities of Diols,
J. Am. Soc. Mass Spectrom., 1993, 4, 9, 723, https://doi.org/10.1016/1044-0305(93)80051-Y
. [all data]
Anteunis and Rommelaere, 1970
Anteunis, M.; Rommelaere, Y.,
NMR experiments on acetals. XXIX. The ease of acetonide formation of some glycols,
Bull. Soc. Chim. Belg., 1970, 79, 523-530. [all data]
Tsvetkov, Sopin, et al., 1986
Tsvetkov, V.G.; Sopin, V.P.; Tsvetkova, L.Ya.; Marchenko, G.N.,
Enthalpy of reaction of nitric acid with some organic compounds,
J. Gen. Chem. USSR, 1986, 56, 471-474. [all data]
Hendricks, de Clercq, et al., 2002
Hendricks, J.H.; de Clercq, H.L.; Freidhoff, C.B.; Arnold, S.T.; Eaton, J.G.; Fancher, C.; Lyapustina, S.A.; S.,
Anion solvation at the microscopic level: Photoelectron spectroscopy of the solvated anion clusters, NO-(Y)(n), where Y=Ar, Kr, Xe, N2O, H2S, NH3, H2O, and C2H4(OH)(2),
J. Chem. Phys., 2002, 116, 18, 7926-7938, https://doi.org/10.1063/1.1457444
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid S°gas Entropy of gas at standard conditions S°liquid Entropy of liquid at standard conditions 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 ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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