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
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Ion clustering data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
• 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

Condensed 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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Ion clustering data, 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:
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

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Ion clustering data, 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:
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)

Ion clustering data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

CH₆N⁺ +  = (CH₆N⁺ • )

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

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

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

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₄H₁₁O₂⁺ +  = (C₄H₁₁O₂⁺ • )

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

Bond type: Hydrogen bonds between protonated and neutral organics

(C₄H₁₁O₂⁺ • 2) +  = (C₄H₁₁O₂⁺ • 3)

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

Bond type: Hydrogen bonds between protonated and neutral organics

Free energy of reaction

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

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

Bond type: Hydrogen bonds between protonated and neutral organics

C₅H₆N⁺ +  = (C₅H₆N⁺ • )

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

 +  = ( • )

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

( • ) +  = ( • 2)

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

 +  = ( • )

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

( • ) +  = ( • 2)

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

 +  = ( • )

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

( • ) +  = ( • 2)

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

( • 2) +  = ( • 3)

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

 +  = ( • )

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

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

( • ) +  = ( • 2)

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

 +  = ( • )

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

( • ) +  = ( • 2)

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

 +  = ( • )

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

Free energy of reaction

( • ) +  = ( • 2)

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

( • 2) +  = ( • 3)

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

 +  = ( • )

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

( • ) +  = ( • 2)

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

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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering data, 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]

Wiberg, Morgan, et al., 1994
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]

Loucks and Laidler, 1967
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Trejo, L.M.; Costas, M.; Patterson, D., Excess heat capacity of organic mixtures, Internat. DATA Series, Selected Data Mixt., 1991, Ser. [all data]

Kusano, Suurkuusk, et al., 1973
Kusano, K.; Suurkuusk, J.; Wads, I., Thermochemistry of solutions of biochemical model compounds. 2. Alkoxyethanols and 1,2-dialkoxyethanes in water, J. Chem. Thermodynam. 5,757-767 (1973).73LEB/TSV Lebedev, B.V., Tsvetkova, L.Ya., and Rabinovich, I.B., Specific heat and thermodynamic functions of poly(vinyltrimethylsilane), Tr. Khim. Khim. Tekhnol., 1973, (1), 17-18. [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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Kobe, K.A.; Ravicz, A.E.; Vohra, S.P., Critical Properties and Vapor Pressures of Some Ethers and Heterocyclic Compounds, J. Chem. Eng. Data, 1956, 1, 50. [all data]

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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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Notes

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• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  Pc	Critical pressure
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Vc	Critical volume
  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
  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
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