Ethanol, 2,2'-oxybis-
- Formula: C4H10O3
- Molecular weight: 106.1204
- IUPAC Standard InChIKey: MTHSVFCYNBDYFN-UHFFFAOYSA-N
- CAS Registry Number: 111-46-6
- 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: Diethylene glycol; β,β'-Dihydroxydiethyl ether; Bis(β-hydroxyethyl) ether; Bis(2-hydroxyethyl) ether; Brecolane NDG; Deactivator E; Deactivator H; Dicol; Digenos; Diglycol; Digol; Dissolvant APV; DEG; Ethylene diglycol; TL4N; 2,2'-Oxybis[Ethanol]; 2,2'-Oxydiethanol; 2,2'-Oxyethanol; 3-Oxapentane-1,5-diol; Glycol hydroxyethyl ether; 3-Oxa-1,5-pentanediol; 2-Hydroxyethyl ether; Ethanol, 2,2'-oxydi-; Glycol ether; 2,2-Di(hydroxyethyl) ether; Diethylenglykol; Dihydroxydiethyl ether; 2,2'-Dihydroxyethyl ether; 2-(2-Hydroxyethoxy)ethanol; β,β'-Dihydroxyethyl ether; 1,5-Dihydroxy-3-oxapentane; 3-Oxapentamethylene-1,5-diol; NSC 36391; Carbitol; D.E.H. 20; D.E.H. 52; Her
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, 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 | -150.22 ± 0.57 | kcal/mol | Ccb | Moureu and Dode, 1937 | Reanalyzed by Cox and Pilcher, 1970, Original value = -150.1 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -567.56 ± 0.57 | kcal/mol | Ccb | Moureu and Dode, 1937 | Reanalyzed by Cox and Pilcher, 1970, Original value = -567.9 kcal/mol; Corresponding ΔfHºliquid = -150.22 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -567.14 | kcal/mol | Ccb | Rinkenbach, 1927 | Corresponding ΔfHºliquid = -150.6 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
58.29 | 298. | Zaripov, 1982 | T = 298, 323, 363 K.; DH |
68.59 | 298. | Stephens and Tamplin, 1979 | T = 273 to 513 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
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 519. ± 3. | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 265.4 | K | N/A | Anonymous, 1958 | Uncertainty assigned by TRC = 0.6 K; TRC |
Tfus | 263.05 | K | N/A | Gallaugher and Hibbert, 1936 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 262.80 | K | N/A | Rinkenbach, 1927, 2 | Uncertainty assigned by TRC = 0.1 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 753. | K | N/A | Nikitin, Pavlov, et al., 1995 | Uncertainty assigned by TRC = 4. K; TRC |
Tc | 723.5 | K | N/A | Anselme and Teja, 1990 | Uncertainty assigned by TRC = 50. K; Tc > 723.5 K, which was observed with decomposition; TRC |
Tc | 680. | K | N/A | Stephens and Tamplin, 1979, 2 | Uncertainty assigned by TRC = 20. K; TC data from Union Carbide Corp.; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 47.08 | atm | N/A | Nikitin, Pavlov, et al., 1995 | Uncertainty assigned by TRC = 0.49 atm; TRC |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
406.2 | 0.018 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
15.9 | 413. | TGA | Al-Najjar and Al-Sammerrai, 2007 | Based on data from 373. to 453. K.; AC |
16.0 ± 0.07 | 420. | EB | Steele, Chirico, et al., 2002 | Based on data from 410. to 539. K.; AC |
15.1 ± 0.07 | 460. | EB | Steele, Chirico, et al., 2002 | Based on data from 410. to 539. K.; AC |
14.1 ± 0.07 | 500. | EB | Steele, Chirico, et al., 2002 | Based on data from 410. to 539. K.; AC |
13.2 ± 0.1 | 540. | EB | Steele, Chirico, et al., 2002 | Based on data from 410. to 539. K.; AC |
14.3 | 379. | A | Stephenson and Malanowski, 1987 | Based on data from 364. to 518. K.; AC |
16.0 | 427. | N/A | Ambrose and Hall, 1981 | Based on data from 412. to 513. K. See also Boublik, Fried, et al., 1984.; AC |
13.7 ± 1.4 | 273. | V | Gallaugher and Hibbert, 1937 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 12.50 kcal/mol; ALS |
15.91 | 523. | V | Rinkenbach, 1927 | ALS |
16.5 | 418. | N/A | Rinkenbach, 1927, 3 | Based on data from 403. to 513. K. See also Boublik, Fried, et al., 1984.; AC |
Reaction thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Gas Chromatography, 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: C4H10O3 + HNO3 = C4H9NO5 + H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -2.1 | kcal/mol | Cm | Tsvetkov, Sopin, et al., 1986 | liquid phase |
IR Spectrum
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, References, Notes
Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Chromatography
Go To: Top, Condensed phase thermochemistry data, Phase change 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 | Apiezon L | 160. | 927. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
Packed | Apiezon L | 170. | 925. | Singliar and Dykyj, 1969 |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | PEG-2000 | 200. | 1989. | 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 | 967. | 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 | Supelcowax-10 | 1975. | Moreira, Trugo, et al., 2002 | 30. m/0.25 mm/0.25 μm, He, 3. K/min, 230. C @ 30. min; Tstart: 50. C |
Capillary | Carbowax 20M | 1968. | Chen, Kuo, et al., 1986 | He, 50. C @ 5. min, 2. K/min, 200. C @ 40. min; Column length: 50. m; Column diameter: 0.32 mm |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 941. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1953. | Peng, Yang, et al., 1991 | Program: not specified |
References
Go To: Top, Condensed phase thermochemistry data, Phase change 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.
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]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Rinkenbach, 1927
Rinkenbach, Wm.H.,
Properties of Diethylene Glycol,
Ind. Eng. Chem., 1927, 19, 474-475. [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]
Anonymous, 1958
Anonymous, R.,
, Am. Pet. Inst. Res. Proj. 45, Ohio State Univ., 1958. [all data]
Gallaugher and Hibbert, 1936
Gallaugher, A.F.; Hibbert, H.,
Studies on reactions relating to carbohydrates and polysaccharides: xlix molecular weight, molar refraction, freezing point and other properties of the polyethylene glycols and their derivatives,
J. Am. Chem. Soc., 1936, 58, 813. [all data]
Rinkenbach, 1927, 2
Rinkenbach, W.H.,
Properties of Diethylene Glycol,
Ind. Eng. Chem., 1927, 19, 475-6. [all data]
Nikitin, Pavlov, et al., 1995
Nikitin, E.D.; Pavlov, P.A.; Popov, A.P.,
(Gas + liquid) critical temperatures and pressures of polyethene glycols for HOCH2CH2OH to H(OCH2CH2)v.apprxeq.13.2OH,
J. Chem. Thermodyn., 1995, 27, 43-51. [all data]
Anselme and Teja, 1990
Anselme, M.J.; Teja, A.S.,
The critical properties of rapidly reacting substances,
AIChE Symp. Ser., 1990, 86, 279, 128-32. [all data]
Stephens and Tamplin, 1979, 2
Stephens, M.A.; Tamplin, W.S.,
Saturated Liquid SPecific Heats of Ethylene GLycol Homologues,
J. Chem. Eng. Data, 1979, 24, 81-2. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Al-Najjar and Al-Sammerrai, 2007
Al-Najjar, Hazim; Al-Sammerrai, Dhoaib,
Thermogravimetric determination of the heat of vaporization of some highly polar solvents,
J. Chem. Technol. Biotechnol., 2007, 37, 3, 145-152, https://doi.org/10.1002/jctb.280370302
. [all data]
Steele, Chirico, et al., 2002
Steele, W.V.; Chirico, R.D.; Cowell, A.B.; Knipmeyer, S.E.; Nguyen, A.,
Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for Methyl Benzoate, Ethyl Benzoate, ( R )-(+)-Limonene, tert -Amyl Methyl Ether, trans -Crotonaldehyde, and Diethylene Glycol,
J. Chem. Eng. Data, 2002, 47, 4, 667-688, https://doi.org/10.1021/je0100847
. [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]
Ambrose and Hall, 1981
Ambrose, D.; Hall, D.J.,
Thermodynamic properties of organic oxygen compounds L. The vapour pressures of 1,2-ethanediol (ethylene glycol) and bis(2-hydroxyethyl) ether (diethylene glycol),
The Journal of Chemical Thermodynamics, 1981, 13, 1, 61-66, https://doi.org/10.1016/S0021-9614(81)80009-2
. [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]
Gallaugher and Hibbert, 1937
Gallaugher, A.F.; Hibbert, H.,
Studies on reactions relating to carbohydrates and polysaccharides. LV. Vapor pressures of the polyethylene glycols and their derivatives,
J. Am. Chem. Soc., 1937, 59, 2521-2525. [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]
Rinkenbach, 1927, 3
Rinkenbach, Wm.H.,
Properties of Diethylene Glycol 1,
Ind. Eng. Chem., 1927, 19, 4, 474-476, https://doi.org/10.1021/ie50208a017
. [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]
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]
Singliar and Dykyj, 1969
Singliar, M.; Dykyj, J.,
Gas chromatography of glycol ethers,
Collect. Czech. Chem. Commun., 1969, 34, 3, 767-775, https://doi.org/10.1135/cccc19690767
. [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]
Moreira, Trugo, et al., 2002
Moreira, R.F.A.; Trugo, L.C.; Pietroluongo, M.; de Maria, C.A.B.,
Flavor composition of cashew (Anacardium occidentale) and marmeleiro (Croton species) honeys,
J. Agric. Food Chem., 2002, 50, 26, 7616-7621, https://doi.org/10.1021/jf020464b
. [all data]
Chen, Kuo, et al., 1986
Chen, C.-C.; Kuo, M.-C.; Liu, S.-E.; Wu, C.-M.,
Volatile components of salted and pickled prunes (Prunus mume Sieb. et Zucc.),
J. Agric. Food Chem., 1986, 34, 1, 140-144, https://doi.org/10.1021/jf00067a038
. [all data]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F.,
Prediction of rentention idexes. II. Structure-retention index relationship on polar columns,
J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F
. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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