Ethanol, 2,2'-oxybis-

• Formula: C₄H₁₀O₃
• Molecular weight: 106.1204
• IUPAC Standard InChI: InChI=1S/C4H10O3/c5-1-3-7-4-2-6/h5-6H,1-4H2 Copy

  
• IUPAC Standard InChIKey: MTHSVFCYNBDYFN-UHFFFAOYSA-N Copy
• 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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Henry's Law data
• Options:
  • Switch to calorie-based units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Condensed phase thermochemistry data

Go To: Top, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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

Constant pressure heat capacity of liquid

Phase change data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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:
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

Reduced pressure boiling point

Enthalpy of vaporization

Reaction thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), 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

IR Spectrum

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes

Data compiled by: Coblentz Society, Inc.

• LIQUID (NEAT); PERKIN-ELMER 521 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas

Mass spectrum (electron ionization)

Go To: Top, Condensed phase thermochemistry data, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

Gas Chromatography

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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

View large format table.

Kovats' RI, polar column, isothermal

View large format table.

Van Den Dool and Kratz RI, non-polar column, temperature ramp

View large format table.

Van Den Dool and Kratz RI, polar column, temperature ramp

View large format table.

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Normal alkane RI, polar column, custom temperature program

View large format table.

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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, Mass spectrum (electron ionization), 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
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.