Dimethyl ether

• Formula: C₂H₆O
• Molecular weight: 46.0684
• IUPAC Standard InChI: InChI=1S/C2H6O/c1-3-2/h1-2H3 Copy

  
• IUPAC Standard InChIKey: LCGLNKUTAGEVQW-UHFFFAOYSA-N Copy
• CAS Registry Number: 115-10-6
• 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.
• Isotopologues:
  • (CD3)2O
• Other names: Methane, oxybis-; Methyl ether; Methoxymethane; Wood ether; Oxybismethane; (CH3)2O; Ether, dimethyl; Ether, methyl; UN 1033; Dimethyl oxide; Dymel A; Dymel; Demeon D; DME; Methane, 1,1'-oxybis-
• 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 (reactions 1 to 50)
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data: reactions 51 to 52
  • Henry's Law data
  • Gas phase ion energetics data
  • Ion clustering data
  • Vibrational and/or electronic energy levels
• 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Constant pressure heat capacity of gas

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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Entropy of vaporization

Antoine Equation Parameters

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

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Enthalpy of fusion

Entropy of fusion

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

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.

Reactions 1 to 50

 +  = ( • )

By formula: Li⁺ + C₂H₆O = (Li⁺ • C₂H₆O)

Enthalpy of reaction

C₃H₇O₂⁺ +  = (C₃H₇O₂⁺ • )

By formula: C₃H₇O₂⁺ + C₂H₆O = (C₃H₇O₂⁺ • C₂H₆O)

Bond type: Hydrogen bonds of the type OH-O between organics

C₄H₉O₂⁺ +  = (C₄H₉O₂⁺ • )

By formula: C₄H₉O₂⁺ + C₂H₆O = (C₄H₉O₂⁺ • C₂H₆O)

Bond type: Hydrogen bonds of the type OH-O between organics

( • ) +  = ( • 2)

By formula: (Na⁺ • C₂H₆O) + C₂H₆O = (Na⁺ • 2C₂H₆O)

 +  = ( • )

By formula: Na⁺ + C₂H₆O = (Na⁺ • C₂H₆O)

Free energy of reaction

C₁₀H₁₀Fe⁺ +  = (C₁₀H₁₀Fe⁺ • )

By formula: C₁₀H₁₀Fe⁺ + C₂H₆O = (C₁₀H₁₀Fe⁺ • C₂H₆O)

Free energy of reaction

(CH₅O⁺ • 2) +  = (CH₅O⁺ •  • 2)

By formula: (CH₅O⁺ • 2CH₄O) + C₂H₆O = (CH₅O⁺ • C₂H₆O • 2CH₄O)

Bond type: Hydrogen bonds of the type OH-O between organics

(CH₅O⁺ • 3) +  = (CH₅O⁺ •  • 3)

By formula: (CH₅O⁺ • 3CH₄O) + C₂H₆O = (CH₅O⁺ • C₂H₆O • 3CH₄O)

Bond type: Hydrogen bonds of the type OH-O between organics

(CH₅O⁺ • ) +  = (CH₅O⁺ •  • )

By formula: (CH₅O⁺ • CH₄O) + C₂H₆O = (CH₅O⁺ • C₂H₆O • CH₄O)

Bond type: Hydrogen bonds of the type OH-O between organics

C₂H₇O⁺ +  = (C₂H₇O⁺ • )

By formula: C₂H₇O⁺ + C₂H₆O = (C₂H₇O⁺ • C₂H₆O)

Bond type: Hydrogen bonds of the type OH-O between organics

 +  = ( • )

By formula: K⁺ + C₂H₆O = (K⁺ • C₂H₆O)

CH₅O⁺ +  = (CH₅O⁺ • )

By formula: CH₅O⁺ + C₂H₆O = (CH₅O⁺ • C₂H₆O)

Bond type: Hydrogen bonds of the type OH-O between organics

(C₂H₇O⁺ •  • 2) +  = (C₂H₇O⁺ • 2 • 2)

By formula: (C₂H₇O⁺ • C₂H₆O • 2H₂O) + C₂H₆O = (C₂H₇O⁺ • 2C₂H₆O • 2H₂O)

Bond type: Hydrogen bonds of the type OH-O between organics

(C₂H₇O⁺ • ) +  = (C₂H₇O⁺ •  • )

By formula: (C₂H₇O⁺ • C₂H₆O) + H₂O = (C₂H₇O⁺ • H₂O • C₂H₆O)

Bond type: Hydrogen bond (positive ion to hydride)

(C₂H₇O⁺ •  • ) +  = (C₂H₇O⁺ • 2 • )

By formula: (C₂H₇O⁺ • C₂H₆O • H₂O) + C₂H₆O = (C₂H₇O⁺ • 2C₂H₆O • H₂O)

Bond type: Hydrogen bonds of the type OH-O between organics

(C₂H₇O⁺ • 2 • ) +  = (C₂H₇O⁺ • 3 • )

By formula: (C₂H₇O⁺ • 2C₂H₆O • H₂O) + C₂H₆O = (C₂H₇O⁺ • 3C₂H₆O • H₂O)

Bond type: Hydrogen bonds between protonated and neutral organics

(C₂H₇O⁺ • 2 • ) +  = (C₂H₇O⁺ • 3 • )

By formula: (C₂H₇O⁺ • 2CH₄O • C₂H₆O) + CH₄O = (C₂H₇O⁺ • 3CH₄O • C₂H₆O)

Bond type: Hydrogen bonds of the type OH-O between organics

(C₂H₇O⁺ •  • ) +  = (C₂H₇O⁺ • 2 • )

By formula: (C₂H₇O⁺ • CH₄O • C₂H₆O) + CH₄O = (C₂H₇O⁺ • 2CH₄O • C₂H₆O)

Bond type: Hydrogen bonds of the type OH-O between organics

(C₂H₇O⁺ •  • 2) +  = (C₂H₇O⁺ • 2 • 2)

By formula: (C₂H₇O⁺ • H₂O • 2C₂H₆O) + H₂O = (C₂H₇O⁺ • 2H₂O • 2C₂H₆O)

Bond type: Hydrogen bond (positive ion to hydride)

(C₂H₇O⁺ •  • 3) +  = (C₂H₇O⁺ • 2 • 3)

By formula: (C₂H₇O⁺ • H₂O • 3C₂H₆O) + H₂O = (C₂H₇O⁺ • 2H₂O • 3C₂H₆O)

Bond type: Hydrogen bond (positive ion to hydride)

(C₂H₇O⁺ • 2 • ) +  = (C₂H₇O⁺ • 3 • )

By formula: (C₂H₇O⁺ • 2H₂O • C₂H₆O) + H₂O = (C₂H₇O⁺ • 3H₂O • C₂H₆O)

Bond type: Hydrogen bond (positive ion to hydride)

(C₂H₇O⁺ • 2) +  = (C₂H₇O⁺ •  • 2)

By formula: (C₂H₇O⁺ • 2H₂O) + C₂H₆O = (C₂H₇O⁺ • C₂H₆O • 2H₂O)

Bond type: Hydrogen bonds of the type OH-O between organics

(C₂H₇O⁺ • 3) +  = (C₂H₇O⁺ •  • 3)

By formula: (C₂H₇O⁺ • 3H₂O) + C₂H₆O = (C₂H₇O⁺ • C₂H₆O • 3H₂O)

Bond type: Hydrogen bonds of the type OH-O between organics

(C₂H₇O⁺ •  • ) +  = (C₂H₇O⁺ • 2 • )

By formula: (C₂H₇O⁺ • H₂O • C₂H₆O) + H₂O = (C₂H₇O⁺ • 2H₂O • C₂H₆O)

Bond type: Hydrogen bond (positive ion to hydride)

(C₂H₇O⁺ • ) +  = (C₂H₇O⁺ •  • )

By formula: (C₂H₇O⁺ • H₂O) + C₂H₆O = (C₂H₇O⁺ • C₂H₆O • H₂O)

Bond type: Hydrogen bonds of the type OH-O between organics

(C₂H₇O⁺ • 2) +  = (C₂H₇O⁺ •  • 2)

By formula: (C₂H₇O⁺ • 2CH₄O) + C₂H₆O = (C₂H₇O⁺ • C₂H₆O • 2CH₄O)

Bond type: Hydrogen bonds of the type OH-O between organics

(C₂H₇O⁺ • 3) +  = (C₂H₇O⁺ •  • 3)

By formula: (C₂H₇O⁺ • 3CH₄O) + C₂H₆O = (C₂H₇O⁺ • C₂H₆O • 3CH₄O)

Bond type: Hydrogen bonds of the type OH-O between organics

(C₂H₇O⁺ • ) +  = (C₂H₇O⁺ •  • )

By formula: (C₂H₇O⁺ • C₂H₆O) + CH₄O = (C₂H₇O⁺ • CH₄O • C₂H₆O)

Bond type: Hydrogen bonds of the type OH-O between organics

(C₂H₇O⁺ • ) +  = (C₂H₇O⁺ •  • )

By formula: (C₂H₇O⁺ • CH₄O) + C₂H₆O = (C₂H₇O⁺ • C₂H₆O • CH₄O)

Bond type: Hydrogen bonds of the type OH-O between organics

(C₂H₇O⁺ • ) +  = (C₂H₇O⁺ • 2)

By formula: (C₂H₇O⁺ • C₂H₆O) + C₂H₆O = (C₂H₇O⁺ • 2C₂H₆O)

Bond type: Hydrogen bonds of the type OH-O between organics

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + C₂H₆O = (CH₆N⁺ • C₂H₆O)

Bond type: Hydrogen bonds of the type NH+-O between organics

( • 2) +  = ( • 3)

By formula: (Li⁺ • 2C₂H₆O) + C₂H₆O = (Li⁺ • 3C₂H₆O)

Enthalpy of reaction

( • 3) +  = ( • 4)

By formula: (Li⁺ • 3C₂H₆O) + C₂H₆O = (Li⁺ • 4C₂H₆O)

Enthalpy of reaction

( • ) +  = ( • 2)

By formula: (Li⁺ • C₂H₆O) + C₂H₆O = (Li⁺ • 2C₂H₆O)

Enthalpy of reaction

 +  = C₂H₆ClO^-

By formula: Cl^- + C₂H₆O = C₂H₆ClO^-

C₂H₅O^- +  =

By formula: C₂H₅O^- + H⁺ = C₂H₆O

( • 2) +  = ( • 3)

By formula: (Na⁺ • 2C₂H₆O) + C₂H₆O = (Na⁺ • 3C₂H₆O)

( • 3) +  = ( • 4)

By formula: (Na⁺ • 3C₂H₆O) + C₂H₆O = (Na⁺ • 4C₂H₆O)

( • 2) +  = ( • 3)

By formula: (K⁺ • 2C₂H₆O) + C₂H₆O = (K⁺ • 3C₂H₆O)

( • 3) +  = ( • 4)

By formula: (K⁺ • 3C₂H₆O) + C₂H₆O = (K⁺ • 4C₂H₆O)

( • 2) +  = ( • 3)

By formula: (Cs⁺ • 2C₂H₆O) + C₂H₆O = (Cs⁺ • 3C₂H₆O)

( • ) +  = ( • 2)

By formula: (Cs⁺ • C₂H₆O) + C₂H₆O = (Cs⁺ • 2C₂H₆O)

( • 2) +  = ( • 3)

By formula: (Rb⁺ • 2C₂H₆O) + C₂H₆O = (Rb⁺ • 3C₂H₆O)

( • ) +  = ( • 2)

By formula: (Rb⁺ • C₂H₆O) + C₂H₆O = (Rb⁺ • 2C₂H₆O)

( • ) +  = ( • 2)

By formula: (K⁺ • C₂H₆O) + C₂H₆O = (K⁺ • 2C₂H₆O)

( • 2) +  = ( • 3)

By formula: (Cu⁺ • 2C₂H₆O) + C₂H₆O = (Cu⁺ • 3C₂H₆O)

( • 3) +  = ( • 4)

By formula: (Cu⁺ • 3C₂H₆O) + C₂H₆O = (Cu⁺ • 4C₂H₆O)

( • ) +  = ( • 2)

By formula: (Cu⁺ • C₂H₆O) + C₂H₆O = (Cu⁺ • 2C₂H₆O)

 +  = ( • )

By formula: Cs⁺ + C₂H₆O = (Cs⁺ • C₂H₆O)

 +  = ( • )

By formula: Rb⁺ + C₂H₆O = (Rb⁺ • C₂H₆O)

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• GAS; DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS)
  2, 4 cm^-1 resolution

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

• gas

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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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, isothermal

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Normal alkane RI, polar column, custom temperature program

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References

Go To: Top, Gas 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.

Pilcher, Pell, et al., 1964
Pilcher, G.; Pell, A.S.; Coleman, D.J., Measurements of heats of combustion by flame calorimetry. Part 2-Dimethyl ether, methyl ethyl ether, methyl n-propyl ether, methyl isopropyl ether, Trans. Faraday Soc., 1964, 60, 499-505. [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]

Handi M.A., 1954
Handi M.A., Molecular spectroscopy. Determination and interpretation of fundamental frequencies of dimethyl ether from infrared absorption spectrum; application for thermodynamic functions calculation, Compt. Rend. Acad. Sci., 1954, 239, 349-351. [all data]

Seha Z., 1955
Seha Z., Thermodynamic functions of dimethyl ether, Chem. Listy, 1955, 49, 1569-1570. [all data]

Banerjee S.C., 1964
Banerjee S.C., Thermodynamic properties of organic compounds. Part 1. Normal symmetrical aliphatic ethers, Brit. Chem. Eng., 1964, 9, 311-313. [all data]

Stull D.R., 1969
Stull D.R., Jr., The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969. [all data]

East A.L.L., 1997
East A.L.L., Ab initio statistical thermodynamical models for the computation of third-law entropies, J. Chem. Phys., 1997, 106, 6655-6674. [all data]

Kistiakowsky G.B., 1940
Kistiakowsky G.B., Gaseous heat capacities. III, J. Chem. Phys., 1940, 8, 618-622. [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]

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

Grosse, 1937
Grosse, A.V., Refractive Indices at Low Temperatures, J. Am. Chem. Soc., 1937, 59, 2739-41. [all data]

Maass and Boomer, 1922
Maass, O.; Boomer, E.H., Vapor Densities at Low Pressures and Over and Extended Temperature Range. I. The Properties of Ethylene Oxide Compared to Oxygen Compounds of Similar Molecular Weight, J. Am. Chem. Soc., 1922, 44, 8, 1709-1728, https://doi.org/10.1021/ja01429a013 . [all data]

Thiele and Schulte, 1920
Thiele, A.; Schulte, E., Binary equilibrium systems with solid carbon dioxide, Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1920, 96, 312-42. [all data]

Wilhoit, Chao, et al., 1985
Wilhoit, R.C.; Chao, J.; Hall, K.R., Thermodynamic Properties of Key Organic Compounds in the Carbon Range C1 to C4. Part 1. Properties of Condensed Phases, J. Phys. Chem. Ref. Data, 1985, 14, 1. [all data]

Kennedy, Sagenkahn, et al., 1941
Kennedy, R.M.; Sagenkahn, M.; Aston, J.G., The Heat Capacity and Entropy, Heats of Fusion and Vaporization and the Vapor Pressure of Dimethyl Ether. The Density of Gaseous Dimethyl Ether, J. Am. Chem. Soc., 1941, 63, 2267-72. [all data]

Zawisza and Glowka, 1970
Zawisza, A.C.; Glowka, S., Liquid-vapour equilibria and thermodynamic functions of dimethyl ether - sulphur dioxide system up to 300c and 77.81 atmospheres, Bull. Acad. Pol. Sci., Ser. Sci. Chim., 1970, 18, 549-54. [all data]

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Tapp, J.S.; Steacie, E.W.R.; Maass, O., Density of a Vapor in Equilibrium with a Liquid Near the Critical Temperature., Can. J. Res., 1933, 9, 217-39. [all data]

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Cardoso, E.; Coppola, A.A., Experimental researches on some thermal properties of gas I the densities of coexisting phases of methyl ether, J. Chim. Phys. Phys.-Chim. Biol., 1923, 20, 337-46. [all data]

Ambrose, Ellender, et al., 1976
Ambrose, D.; Ellender, J.H.; Sprake, C.H.S.; Townsend, R., Thermodynamic properties of organic oxygen compounds XLIII. Vapour pressures of some ethers, The Journal of Chemical Thermodynamics, 1976, 8, 2, 165-178, https://doi.org/10.1016/0021-9614(76)90090-2 . [all data]

Kennedy, Sagenkahn, et al., 1941, 2
Kennedy, R.M.; Sagenkahn, M.; Aston, J.G., The heat capacity and entropy, heats of fusion and vaporization, and the vapor pressure of dimethyl ether. The density of gaseous dimethyl ether, J. Am. Chem. Soc., 1941, 63, 2267-2272. [all data]

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Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [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]

Woodin and Beauchamp, 1978
Woodin, R.L.; Beauchamp, J.L., Bonding of Li+ to Lewis Bases in the Gas Phase. Reversals in Methyl Substituent Effects for Different Reference Acids, J. Am. Chem. Soc., 1978, 100, 2, 501, https://doi.org/10.1021/ja00470a024 . [all data]

Dzidic and Kebarle, 1970
Dzidic, I.; Kebarle, P., Hydration of the Alkali Ions in the Gas Phase. Enthalpies and Entropies of Reactions M+(H2O)n-1 + H2O = M+(H2O)n, J. Phys. Chem., 1970, 74, 7, 1466, https://doi.org/10.1021/j100702a013 . [all data]

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Notes

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

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  Pc	Critical pressure
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Vc	Critical volume
  ΔcH°gas	Enthalpy of combustion of gas at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  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
  ΔvapS	Entropy of vaporization
  ρc	Critical density

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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