2,5,8,11-Tetraoxadodecane

• Formula: C₈H₁₈O₄
• Molecular weight: 178.2261
• IUPAC Standard InChI: InChI=1S/C8H18O4/c1-9-3-5-11-7-8-12-6-4-10-2/h3-8H2,1-2H3 Copy

  
• IUPAC Standard InChIKey: YFNKIDBQEZZDLK-UHFFFAOYSA-N Copy
• CAS Registry Number: 112-49-2
• 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: Ansul Ether 161; Ethane, 1,2-bis(2-methoxyethoxy)-; Glyme-3; Triethylene glycol dimethyl ether; Triglyme; 1,2-Bis(2-methoxyethoxy)ethane; (CH3O(CH2)2OCH2)2; 1,2-Bis(methoxyethoxy)ethane; Dimethyl ether of triethylene glycol; Glyme 4; NSC 66400; triglyme (triethylene glycol dimethyl ether)
• 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)
  • References
  • Notes
• Other data available:
  • Gas phase ion energetics data
  • Ion clustering data
  • Gas Chromatography
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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 by: Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

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

Reduced pressure boiling point

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 by: Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₈H₁₈O₄ = (C₃H₁₀N⁺ • C₈H₁₈O₄)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₄H₅N₂⁺ +  = (C₄H₅N₂⁺ • )

By formula: C₄H₅N₂⁺ + C₈H₁₈O₄ = (C₄H₅N₂⁺ • C₈H₁₈O₄)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₆H₁₄N⁺ +  = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₈H₁₈O₄ = (C₆H₁₄N⁺ • C₈H₁₈O₄)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

( • 2) +  = ( • 3)

By formula: (C₈H₁₈O₄ • 2H₂O) + H₂O = (C₈H₁₈O₄ • 3H₂O)

Bond type: Hydrogen bond (positive ion to hydride)

( • 3) +  = ( • 4)

By formula: (C₈H₁₈O₄ • 3H₂O) + H₂O = (C₈H₁₈O₄ • 4H₂O)

Bond type: Hydrogen bond (positive ion to hydride)

( • ) +  = ( • 2)

By formula: (C₈H₁₈O₄ • H₂O) + H₂O = (C₈H₁₈O₄ • 2H₂O)

Bond type: Hydrogen bond (positive ion to hydride)

C₅H₆N⁺ +  = (C₅H₆N⁺ • )

By formula: C₅H₆N⁺ + C₈H₁₈O₄ = (C₅H₆N⁺ • C₈H₁₈O₄)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

 +  = ( • )

By formula: C₈H₁₈O₄ + H₂O = (C₈H₁₈O₄ • H₂O)

Bond type: Hydrogen bond (positive ion to hydride)

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• Not specified, most likely a prism, grating, or hybrid spectrometer.; (NO SPECTRUM, ONLY SCANNED IMAGE IS AVAILABLE)

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

References

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

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Beaumont, Clegg, et al., 1966
Beaumont, R.H.; Clegg, B.; Gee, G.; Herbert, J.B.M.; Marks, D.J.; Roberts, R.C.; Sims, D., Heat capacities of propylene oxide and of some polymers of ethylene and propylene oxides, Polymer, 1966, 7, 401-416. [all data]

Trejo, Costas, et al., 1991
Trejo, L.M.; Costas, M.; Patterson, D., Excess heat capacity of organic mixtures, Internat. DATA Series, Selected Data Mixt., 1991, Ser. [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]

Haertel, 1985
Haertel, G.H., Low-volatility polar organic solvents for sulfur dioxide, hydrogen sulfide, and carbonyl sulfide., J. Chem. Eng. Data, 1985, 30, 57. [all data]

Anonymous, 1982
Anonymous, X., Glymes Grant Chemical, 1982, Baton Rouge, LA 1982. [all data]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]

Beaumont, Clegg, et al., 1966, 2
Beaumont, R.H.; Clegg, B.; Gee, G.; Herbert, J.B.M.; Marks, D.J.; Roberts, R.C.; Sims, D., Heat Capacities of Propylene Oxide and of Some Polymers of Ethylene and Propylene Oxides, Polymer, 1966, 7, 401. [all data]

Nichols, Orf, et al., 2000
Nichols, Gary; Orf, Jennifer; Reiter, Sarah M.; Chickos, James; Gokel, George W., The vaporization enthalpies of some crown and polyethers by correlation gas chromatography, Thermochimica Acta, 2000, 346, 1-2, 15-28, https://doi.org/10.1016/S0040-6031(99)00405-0 . [all data]

Domalski and Hearing, 1996
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]

Meot-Ner (Mautner), 1983
Meot-Ner (Mautner), M., The Ionic Hydrogen Bond. 3. Multiple and -CH+...O- Bonds. Complexes of Ammonium Ions with Polyethers and Crown Ethers, J. Am. Chem. Soc., 1983, 105, 15, 4912, https://doi.org/10.1021/ja00353a012 . [all data]

Meot-Ner (Mautner), Sieck, et al., 1994
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]

Notes

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

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  ΔvapH°	Enthalpy of vaporization at standard conditions

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