2,5,8,11-Tetraoxadodecane
- Formula: C8H18O4
- Molecular weight: 178.2261
- IUPAC Standard InChIKey: YFNKIDBQEZZDLK-UHFFFAOYSA-N
- 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)
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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: Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
S°liquid | 117.8 | cal/mol*K | N/A | Beaumont, Clegg, et al., 1966 | Extrapolation below 90 K, 103.8 J/mol*K. |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
87.902 | 298.15 | Trejo, Costas, et al., 1991 | |
88.00 | 298.15 | Beaumont, Clegg, et al., 1966 | T = 90 to 350 K. |
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 489.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 489. | K | N/A | Haertel, 1985 | Uncertainty assigned by TRC = 2. K; TRC |
Tboil | 489.15 | K | N/A | Anonymous, 1982 | TRC |
Tboil | 489. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 228.15 | K | N/A | Anonymous, 1982 | TRC |
Tfus | 228. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 229.3 | K | N/A | Beaumont, Clegg, et al., 1966, 2 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 15.2 ± 0.79 | kcal/mol | CGC | Nichols, Orf, et al., 2000 | AC |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
376.7 | 0.013 | Weast and Grasselli, 1989 | BS |
376.6 | 0.013 | Buckingham and Donaghy, 1982 | BS |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
5.667 | 229.3 | Domalski and Hearing, 1996 | AC |
5.6680 | 229.3 | Beaumont, Clegg, et al., 1966 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
24.71 | 229.3 | Beaumont, Clegg, et al., 1966 | DH |
Reaction thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics 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: 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
By formula: C3H10N+ + C8H18O4 = (C3H10N+ • C8H18O4)
Bond type: Hydrogen bonds with polydentate bonding in positive ions
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 34.6 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; triglyme |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 40.0 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; triglyme |
By formula: C4H5N2+ + C8H18O4 = (C4H5N2+ • C8H18O4)
Bond type: Hydrogen bonds with polydentate bonding in positive ions
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 37.0 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; triglyme |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 41.4 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; triglyme |
By formula: C6H14N+ + C8H18O4 = (C6H14N+ • C8H18O4)
Bond type: Hydrogen bonds with polydentate bonding in positive ions
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 43.3 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; triglyme |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 43.8 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; triglyme |
By formula: (C8H18O4 • 2H2O) + H2O = (C8H18O4 • 3H2O)
Bond type: Hydrogen bond (positive ion to hydride)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 10.3 | kcal/mol | PHPMS | Meot-Ner (Mautner), Sieck, et al., 1994 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 22.9 | cal/mol*K | PHPMS | Meot-Ner (Mautner), Sieck, et al., 1994 | gas phase |
By formula: (C8H18O4 • 3H2O) + H2O = (C8H18O4 • 4H2O)
Bond type: Hydrogen bond (positive ion to hydride)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 9.1 | kcal/mol | PHPMS | Meot-Ner (Mautner), Sieck, et al., 1994 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 21.2 | cal/mol*K | PHPMS | Meot-Ner (Mautner), Sieck, et al., 1994 | gas phase |
By formula: (C8H18O4 • H2O) + H2O = (C8H18O4 • 2H2O)
Bond type: Hydrogen bond (positive ion to hydride)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 12.3 | kcal/mol | PHPMS | Meot-Ner (Mautner), Sieck, et al., 1994 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 31.7 | cal/mol*K | PHPMS | Meot-Ner (Mautner), Sieck, et al., 1994 | gas phase |
By formula: C5H6N+ + C8H18O4 = (C5H6N+ • C8H18O4)
Bond type: Hydrogen bonds with polydentate bonding in positive ions
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 34.7 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1983 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 38.3 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1983 | gas phase |
By formula: C8H18O4 + H2O = (C8H18O4 • H2O)
Bond type: Hydrogen bond (positive ion to hydride)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 20.4 | kcal/mol | PHPMS | Meot-Ner (Mautner), Sieck, et al., 1994 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 40.1 | cal/mol*K | PHPMS | Meot-Ner (Mautner), Sieck, et al., 1994 | gas phase |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 226.2 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 213.3 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.8 | PE | Baker, Armen, et al., 1983 | Vertical value; LBLHLM |
IR Spectrum
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes
Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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
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Additional Data
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Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | NIST Mass Spectrometry Data Center |
NIST MS number | 341344 |
Gas Chromatography
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1232. | Olson, Wong, et al., 1987 | 30. m/0.32 mm/1.0 μm, 5. K/min; Tstart: 20. C; Tend: 200. C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1232.3 | Olson, Wong, et al., 1988 | 30. m/0.32 mm/1. μm, 5. K/min; Tstart: 20. C; Tend: 200. C |
Lee's RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 205.88 | Eckel, Ross, et al., 1993 | Program: not specified |
Capillary | Methyl Silicone | 208.42 | Eckel, Ross, et al., 1993 | Program: not specified |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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.
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]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Baker, Armen, et al., 1983
Baker, A.D.; Armen, G.H.; Funaro, S.,
Oral levels of crown ethers and related macrocycles studies by ultraviolet photoelectron spectroscopy: Relationship to complexation studies,
J. Chem. Soc. Dalton Trans., 1983, 2519. [all data]
Olson, Wong, et al., 1987
Olson, K.L.; Wong, C.A.; Fleck, L.L.; Lazar, D.F.,
Qualitative and Quantitative Determination of Solvent Formulations in Automotive Paints,
J. Chromatogr. Sci., 1987, 25, 9, 418-423, https://doi.org/10.1093/chromsci/25.9.418
. [all data]
Olson, Wong, et al., 1988
Olson, K.L.; Wong, C.A.; Fleck, L.L.; Lazar, D.F.,
Qualitative and quantitative determination of solvent formulations in automotive paints,
J. Coat. Technol., 1988, 60, 762, 45-50. [all data]
Eckel, Ross, et al., 1993
Eckel, W.P.; Ross, B.; Isensee, R.K.,
Pentobarbital found in ground water,
Ground Water, 1993, 31, 5, 801-804, https://doi.org/10.1111/j.1745-6584.1993.tb00853.x
. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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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