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
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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
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. |
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 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 |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Packed | SE-30 | 150. | 705. | Tiess, 1984 | Ar, Gas Chrom Q (80-100 mesh); Column length: 3. m |
| Packed | Apiezon L | 160. | 659. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
Kovats' RI, polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Packed | PEG-2000 | 179. | 1695. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
| Packed | PEG-2000 | 180. | 1652. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
| Packed | PEG-2000 | 200. | 1667. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
| Packed | PEG-2000 | 200. | 1670. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Ultra-2 | 702. | Poskrobko, Linkiewicz, et al., 1994 | 25. m/0.32 mm/0.52 μm, H2, 8. K/min; Tstart: 50. C; Tend: 310. C |
Van Den Dool and Kratz RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-Wax | 1621. | Shimoda, Shigematsu, et al., 1995 | 60. m/0.25 mm/0.25 μm, 2. K/min; Tstart: 50. C; Tend: 230. C |
| Capillary | DB-Wax | 1635. | Shiratsuchi, Shimoda, et al., 1994 | 60. m/0.25 mm/0.25 μm, 2. K/min, 230. C @ 60. min; Tstart: 50. C |
| Capillary | DB-Wax | 1635. | Shiratsuchi, Shimoda, et al., 1994, 2 | 60. m/0.25 mm/0.25 μm, He, 2. K/min, 230. C @ 60. min; Tstart: 50. C |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | VF-5 MS | 710. | Leffingwell and Alford, 2011 | 60. m/0.32 mm/0.25 μm, Helium, 2. K/min, 260. C @ 28. min; Tstart: 30. C |
| Capillary | VF-5 MS | 712. | Leffingwell and Alford, 2011 | 60. m/0.32 mm/0.25 μm, Helium, 2. K/min, 260. C @ 28. min; Tstart: 30. C |
| Capillary | OV-101 | 726. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Polydimethyl siloxanes | 726. | Zenkevich, 2001 | Program: not specified |
| Capillary | SPB-1 | 670. | Flanagan, Streete, et al., 1997 | 60. m/0.53 mm/5. μm, He; Program: 40C(6min) => 5C/min => 80C => 10C/min => 200C |
| Capillary | SPB-1 | 670. | Strete, Ruprah, et al., 1992 | 60. m/0.53 mm/5.0 μm, Helium; Program: 40 0C (6 min) 5 0C/min -> 80 0C 10 0C/min -> 200 0C |
| Capillary | SPB-1 | 672. | Strete, Ruprah, et al., 1992 | 60. m/0.53 mm/5.0 μm, Helium; Program: not specified |
Normal alkane RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-Wax | 1660. | Shimadzu, 2012 | 30. m/0.32 mm/0.50 μm, Helium, 4. K/min; Tstart: 40. C; Tend: 260. C |
| Capillary | DB-Wax | 1660. | Shimadzu Corporation, 2003 | 30. m/0.32 mm/0.5 μm, He, 4. K/min; Tstart: 40. C; Tend: 260. C |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, 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]
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]
Tiess, 1984
Tiess, D.,
Gaschromatographische Retentionsindices von 125 leicht- bis mittelflüchtigen organischen Substanzen toxikologisch-analytischer Relevanz auf SE-30,
Wiss. Z. Wilhelm-Pieck-Univ. Rostock Math. Naturwiss. Reihe, 1984, 33, 6-9. [all data]
Bogoslovsky, Anvaer, et al., 1978
Bogoslovsky, Yu.N.; Anvaer, B.I.; Vigdergauz, M.S.,
Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [all data]
Anderson, Jurel, et al., 1973
Anderson, A.; Jurel, S.; Shymanska, M.; Golender, L.,
Gas-liquid chromatography of some aliphatic and heterocyclic mono- and pollyfunctional amines. VII. Retention indices of amines in some polar and unpolar stationary phases,
Latv. PSR Zinat. Akad. Vestis Kim. Ser., 1973, 1, 51-63. [all data]
Poskrobko, Linkiewicz, et al., 1994
Poskrobko, J.; Linkiewicz, M.; Jaworski, M.,
Analysis of high-boiling ethoxylates of methyl, ethyl and butyl alcohols, with the use of gas chromatography,
Chem. Anal. (Warsaw), 1994, 39, 2, 153-159. [all data]
Shimoda, Shigematsu, et al., 1995
Shimoda, M.; Shigematsu, H.; Shiratsuchi, H.; Osajima, Y.,
Comparison of the odor concentrates by SDE and adsorptive column method from green tea infusion,
J. Agric. Food Chem., 1995, 43, 6, 1616-1620, https://doi.org/10.1021/jf00054a037
. [all data]
Shiratsuchi, Shimoda, et al., 1994
Shiratsuchi, H.; Shimoda, M.; Imayoshi, K.; Noda, K.; Osajima, Y.,
Off-flavor compounds in spray-dried skim milk powder,
J. Agric. Food Chem., 1994, 42, 6, 1323-1327, https://doi.org/10.1021/jf00042a014
. [all data]
Shiratsuchi, Shimoda, et al., 1994, 2
Shiratsuchi, H.; Shimoda, M.; Imayoshi, K.; Noda, K.; Osajima, Y.,
Volatile flavor compounds in spray-dried skim milk powder,
J. Agric. Food Chem., 1994, 42, 4, 984-988, https://doi.org/10.1021/jf00040a028
. [all data]
Leffingwell and Alford, 2011
Leffingwell, J.; Alford, E.D.,
Volatile constituents of the giant pufball mushroom (Calvatia gigantea),
Leffingwell Rep., 2011, 4, 1-17. [all data]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Zenkevich, 2001
Zenkevich, I.G.,
Encyclopedia of Chromatography. Derivatization of Carbonyls for GC Analysis, MArcel Dekker, Inc., New York - Basel, 2001, 233. [all data]
Flanagan, Streete, et al., 1997
Flanagan, R.J.; Streete, P.J.; Ramsey, J.D.,
Volatile Substance Abuse, UNODC Technical Series, No 5, United Nations, Office on Drugs and Crime, Vienna International Centre, PO Box 500, A-1400 Vienna, Austria, 1997, 56, retrieved from http://www.odccp.org/pdf/technicalseries1997-01-011.pdf. [all data]
Strete, Ruprah, et al., 1992
Strete, P.J.; Ruprah, M.; Ramsey, J.D.; Flanagan, R.J.,
Detection and identification of volatile substances by headspace capillary gas chromatography to aid the diagnosis of acute poisoning,
Analyst, 1992, 117, 7, 1111-1127, https://doi.org/10.1039/an9921701111
. [all data]
Shimadzu, 2012
Shimadzu, Pharmaceutical Related,
Analysis of pharmaceutical residual solvent (observation of separation) (1) - GC, 2012, retrieved from www.shimadzu.ru/applications/Applicationspdf/GC/Pharma/Pharmaceutical residual solvents GC.pdf. [all data]
Shimadzu Corporation, 2003
Shimadzu Corporation,
Analysis of pharmaceutical residual solvent (observation of separation), 2003, retrieved from http://www.shimadzu.com.br/analitica/aplicacoes/book/pharm69.pdf. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas S°gas Entropy of gas at standard conditions ΔfH°gas Enthalpy of formation of gas 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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