Ethane, 1,2-dimethoxy-

• Formula: C₄H₁₀O₂
• Molecular weight: 90.1210
• IUPAC Standard InChI: InChI=1S/C4H10O2/c1-5-3-4-6-2/h3-4H2,1-2H3 Copy

  
• IUPAC Standard InChIKey: XTHFKEDIFFGKHM-UHFFFAOYSA-N Copy
• CAS Registry Number: 110-71-4
• 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: α,β-Dimethoxyethane; Dimethoxyethane; Dimethyl cellosolve; Ethylene dimethyl ether; Ethylene glycol dimethyl ether; Glycol dimethyl ether; Glyme; Monoethylene glycol dimethyl ether; Monoglyme; 1,2-Dimethoxyethane; 1,2-Ethanediol dimethyl ether; 2,5-Dioxahexane; CH3OCH2CH2OCH3; Egdme; UN 2252; Ansul ether 121; DME; DME (glycol ether); Hisolve MMM; NSC 60542
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar
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

(C₄H₁₁O₂⁺ • 2 • 2) +  = (C₄H₁₁O₂⁺ • 3 • 2)

By formula: (C₄H₁₁O₂⁺ • 2H₂O • 2C₄H₁₀O₂) + H₂O = (C₄H₁₁O₂⁺ • 3H₂O • 2C₄H₁₀O₂)

Bond type: Hydrogen bond (positive ion to hydride)

Free energy of reaction

(C₄H₁₁O₂⁺ • 3 • ) +  = (C₄H₁₁O₂⁺ • 4 • )

By formula: (C₄H₁₁O₂⁺ • 3H₂O • C₄H₁₀O₂) + H₂O = (C₄H₁₁O₂⁺ • 4H₂O • C₄H₁₀O₂)

Bond type: Hydrogen bond (positive ion to hydride)

Free energy of reaction

(C₄H₁₁O₂⁺ • 2) +  = (C₄H₁₁O₂⁺ • 3)

By formula: (C₄H₁₁O₂⁺ • 2C₄H₁₀O₂) + C₄H₁₀O₂ = (C₄H₁₁O₂⁺ • 3C₄H₁₀O₂)

Bond type: Hydrogen bonds between protonated and neutral organics

Free energy of reaction

 +  = ( • )

By formula: Na⁺ + C₄H₁₀O₂ = (Na⁺ • C₄H₁₀O₂)

Free energy of reaction

 +  = ( • )

By formula: K⁺ + C₄H₁₀O₂ = (K⁺ • C₄H₁₀O₂)

Bond type: Polydentate bonding in non-hydrogen-bonded positive ions

( • ) +  = ( • 2)

By formula: (Na⁺ • C₄H₁₀O₂) + C₄H₁₀O₂ = (Na⁺ • 2C₄H₁₀O₂)

(C₄H₁₁O₂⁺ •  • 2) +  = (C₄H₁₁O₂⁺ • 2 • 2)

By formula: (C₄H₁₁O₂⁺ • C₄H₁₀O₂ • 2H₂O) + C₄H₁₀O₂ = (C₄H₁₁O₂⁺ • 2C₄H₁₀O₂ • 2H₂O)

Bond type: Hydrogen bonds between protonated and neutral organics

(C₄H₁₁O₂⁺ • 2 • ) +  = (C₄H₁₁O₂⁺ • 3 • )

By formula: (C₄H₁₁O₂⁺ • 2H₂O • C₄H₁₀O₂) + H₂O = (C₄H₁₁O₂⁺ • 3H₂O • C₄H₁₀O₂)

Bond type: Hydrogen bond (positive ion to hydride)

(C₄H₁₁O₂⁺ •  • 2) +  = (C₄H₁₁O₂⁺ • 2 • 2)

By formula: (C₄H₁₁O₂⁺ • H₂O • 2C₄H₁₀O₂) + H₂O = (C₄H₁₁O₂⁺ • 2H₂O • 2C₄H₁₀O₂)

Bond type: Hydrogen bond (positive ion to hydride)

(C₄H₁₁O₂⁺ •  • ) +  = (C₄H₁₁O₂⁺ • 2 • )

By formula: (C₄H₁₁O₂⁺ • H₂O • C₄H₁₀O₂) + H₂O = (C₄H₁₁O₂⁺ • 2H₂O • C₄H₁₀O₂)

Bond type: Hydrogen bond (positive ion to hydride)

C₅H₆N⁺ +  = (C₅H₆N⁺ • )

By formula: C₅H₆N⁺ + C₄H₁₀O₂ = (C₅H₆N⁺ • C₄H₁₀O₂)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

( • ) +  = ( •  • )

By formula: (H₄N⁺ • C₄H₁₀O₂) + H₃N = (H₄N⁺ • H₃N • C₄H₁₀O₂)

Bond type: Hydrogen bond (positive ion to hydride)

(C₄H₁₁O₂⁺ • ) +  = (C₄H₁₁O₂⁺ •  • )

By formula: (C₄H₁₁O₂⁺ • C₄H₁₀O₂) + H₂O = (C₄H₁₁O₂⁺ • H₂O • C₄H₁₀O₂)

Bond type: Hydrogen bond (positive ion to hydride)

C₄H₁₁O₂⁺ +  = (C₄H₁₁O₂⁺ • )

By formula: C₄H₁₁O₂⁺ + C₄H₁₀O₂ = (C₄H₁₁O₂⁺ • C₄H₁₀O₂)

Bond type: Hydrogen bonds between protonated and neutral organics

 +  = ( • )

By formula: H₄N⁺ + C₄H₁₀O₂ = (H₄N⁺ • C₄H₁₀O₂)

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₄H₁₀O₂ = (C₃H₁₀N⁺ • C₄H₁₀O₂)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₆H₁₄N⁺ +  = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₄H₁₀O₂ = (C₆H₁₄N⁺ • C₄H₁₀O₂)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + C₄H₁₀O₂ = (CH₆N⁺ • C₄H₁₀O₂)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

( • 2) +  = ( • 3)

By formula: (H₄N⁺ • 2C₄H₁₀O₂) + C₄H₁₀O₂ = (H₄N⁺ • 3C₄H₁₀O₂)

( • ) +  = ( • 2)

By formula: (H₄N⁺ • C₄H₁₀O₂) + C₄H₁₀O₂ = (H₄N⁺ • 2C₄H₁₀O₂)

( • 2) +  = ( • 3)

By formula: (Na⁺ • 2C₄H₁₀O₂) + C₄H₁₀O₂ = (Na⁺ • 3C₄H₁₀O₂)

 +  = 2 + 

By formula: C₄H₁₀O₂ + H₂O = 2CH₄O + C₂H₄O

2 +  =  + 

By formula: 2CH₄O + C₂H₄O = C₄H₁₀O₂ + H₂O

( • ) +  = ( • 2)

By formula: (Li⁺ • C₄H₁₀O₂) + C₄H₁₀O₂ = (Li⁺ • 2C₄H₁₀O₂)

( • ) +  = ( • 2)

By formula: (Cs⁺ • C₄H₁₀O₂) + C₄H₁₀O₂ = (Cs⁺ • 2C₄H₁₀O₂)

( • ) +  = ( • 2)

By formula: (Rb⁺ • C₄H₁₀O₂) + C₄H₁₀O₂ = (Rb⁺ • 2C₄H₁₀O₂)

( • ) +  = ( • 2)

By formula: (K⁺ • C₄H₁₀O₂) + C₄H₁₀O₂ = (K⁺ • 2C₄H₁₀O₂)

( • ) +  = ( • 2)

By formula: (Cu⁺ • C₄H₁₀O₂) + C₄H₁₀O₂ = (Cu⁺ • 2C₄H₁₀O₂)

 +  = ( • )

By formula: Li⁺ + C₄H₁₀O₂ = (Li⁺ • C₄H₁₀O₂)

 +  = ( • )

By formula: Cs⁺ + C₄H₁₀O₂ = (Cs⁺ • C₄H₁₀O₂)

 +  = ( • )

By formula: Rb⁺ + C₄H₁₀O₂ = (Rb⁺ • C₄H₁₀O₂)

 +  = ( • )

By formula: Cu⁺ + C₄H₁₀O₂ = (Cu⁺ • C₄H₁₀O₂)

Mass spectrum (electron ionization)

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

Spectrum

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Additional Data

Gas Chromatography

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

Kovats' RI, non-polar column, isothermal

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Kovats' RI, polar column, isothermal

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Normal alkane RI, polar column, temperature ramp

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References

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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.

Steele, Chirico, et al., 1996
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Smith, N.K., Thermodynamic properties and ideal-gas enthalpies of formation for butyl vinyl ether, 1,2-dimethoxyethane, methyl glycolate, bicyclo[2.2.1]hept-2-ene, 5-vinylbicyclo[2.2.1]hept-2-ene, trans-azobenzene, butyl acrylate, di-tert-butyl ether, and hexane-1,6-diol, J. Chem. Eng. Data, 1996, 41, 1285-1302. [all data]

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Wiberg, K.B.; Morgan, K.M.; Maltz, H., Thermochemistry of carbonyl reactions. 6. A study of hydration equilibria, J. Am. Chem. Soc., 1994, 116, 11067-11077. [all data]

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Guanquan, C.; Ott, J.B.; Goates, J.R., (Solid+liquid) phase equilibria and solid-compound formation in 1,2-dimethoxyethane+tetrachloromethane, +trichlorofluoromethane, and +trichloromethane, J. Chem. Thermodyn., 1986, 18, 31. [all data]

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Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Li, Fang, et al., 2009
Li, Dan; Fang, Wenjun; Xie, Wenjie; Xing, Yan; Guo, Yongsheng; Lin, Ruisen, Measurements on Vapor Pressure and Thermal Conductivity for Pseudo-binary Systems of a Hydrocarbon Fuel with Ethylene and Diethylene Glycol Dimethyl Ethers, Energy Fuels, 2009, 23, 2, 794-798, https://doi.org/10.1021/ef8007163 . [all data]

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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]

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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]

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Meot-Ner (Mautner), M.; Sieck, L.W.; Liebman, J.F.; Scheiner, S.; Duan, X., The Ionic Hydrogen Bond. 5. Polydentate and Solvent-Bridged Structures. Complexing of the Proton and the Hydronium Ions by Polyethers, J. Am. Chem. Soc., 1994, 116, 17, 7848, https://doi.org/10.1021/ja00096a047 . [all data]

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Armentrout, P.B.; Rodgers, M.T., An Absolute Sodium Cation Affinity Scale: Threshold Collision-Induced Dissociation Experiments and ab Initio Theory, J. Phys. Chem A, 2000, 104, 11, 2238, https://doi.org/10.1021/jp991716n . [all data]

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Rodgers, M.T.; Armentrout, P.B., Noncovalent Metal-Ligand Bond Energies as Studied by Threshold Collision-Induced Dissociation, Mass Spectrom. Rev., 2000, 19, 4, 215, https://doi.org/10.1002/1098-2787(200007)19:4<215::AID-MAS2>3.0.CO;2-X . [all data]

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More, M.B.; Ray, D.; Armentrout, P.B., Cation-ether complexes in the gas phase: Bond dissociation energies of Na+(dimethyl ether)(x), x=1-4; Na+(1,2-dimethoxyethane)(x), x=1 and 2; and Na+(12-crown-4), J. Phys. Chem. AJOURNAL OF PHYSICAL CHEMISTRY A 101 (5): 831-839 JAN 30 1997, 1997, 101, 831. [all data]

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Castleman, A.W.; Peterson, K.I.; Upschulte, B.L.; Schelling, F.J., Energetics and Structure of Na+ Cluster Ions, Int. J. Mass Spectrom. Ion Phys., 1983, 47, 203, https://doi.org/10.1016/0020-7381(83)87171-X . [all data]

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Notes

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

• Symbols used in this document:
  

  Pc	Critical pressure
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Vc	Critical volume
  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
  ΔrS°	Entropy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ρc	Critical density

• 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.
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