Ethane, 1,1'-oxybis[2-methoxy-
- Formula: C6H14O3
- Molecular weight: 134.1736
- IUPAC Standard InChIKey: SBZXBUIDTXKZTM-UHFFFAOYSA-N
- CAS Registry Number: 111-96-6
- 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. - Other names: Ether, bis(2-methoxyethyl); (2-Methoxyethyl) ether; Bis(2-methoxyethyl) ether; Di(2-Methoxyethyl) ether; Diethylene glycol dimethyl ether; Diglyme; Dimethyl carbitol; Ethanol, 2,2'-oxybis-, dimethyl ether; Glyme-2; Poly-Solv; 2-(2-Methoxyethoxy)-1-methoxyethane; 2,5,8-Trioxanonane; CH3OCH2CH2OCH2CH2OCH3; Dimethoxydiethylene glycol; Dimethyldigol; Diethyl glycol dimethyl ether; 1,1'-Oxybis(2-methoxy)ethane; 2,2'-Oxybisethanol dimethyl ether; Diglycol methyl ether; NSC 59726; Methyl diglyme; diglyme (diethylene glycol dimethyl ether)
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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 as indicated in comments:
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -124.6 | kcal/mol | Semi | Stewart, 2004 | |
ΔfH°gas | -122.3 | kcal/mol | N/A | Gutner, Lebedeva, et al., 1980 | Value computed using ΔfHliquid° value of -556.4±0.9 kj/mol from Gutner, Lebedeva, et al., 1980 and ΔvapH° value of 44.7 kj/mol from Mansson, 1969.; DRB |
ΔfH°gas | -125.4 | kcal/mol | N/A | Baroody and Carpenter, 1972 | Value computed using ΔfHliquid° value of -569.4 kj/mol from Baroody and Carpenter, 1972 and ΔvapH° value of 44.7 kj/mol from Mansson, 1969.; DRB |
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -133.0 ± 0.2 | kcal/mol | Ccb | Gutner, Lebedeva, et al., 1980 | ALS |
ΔfH°liquid | -136.1 | kcal/mol | Ccb | Baroody and Carpenter, 1972 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -909.5 ± 0.2 | kcal/mol | Ccb | Gutner, Lebedeva, et al., 1980 | Corresponding ΔfHºliquid = -133.0 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 84.30 | cal/mol*K | N/A | Beaumont, Clegg, et al., 1966 | Extrapolation below 90 K, 79.91 J/mol*K.; DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
66.386 | 298.15 | Trejo, Costas, et al., 1991 | DH |
66.883 | 298.15 | Villamanan, Casanova, et al., 1982 | DH |
65.51 | 298.15 | Beaumont, Clegg, et al., 1966 | T = 90 to 350 K.; DH |
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
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 435.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 435.15 | K | N/A | Anonymous, 1982 | TRC |
Tboil | 435. | K | N/A | Wallace and Mathews, 1964 | Uncertainty assigned by TRC = 4. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 209.15 | K | N/A | Anonymous, 1982 | TRC |
Tfus | 209.1 | K | N/A | Beaumont, Clegg, et al., 1966, 2 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 11.5 ± 0.1 | kcal/mol | CGC | Nichols, Orf, et al., 2000 | AC |
ΔvapH° | 10.7 | kcal/mol | N/A | Mansson, 1969 | DRB |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
10.9 | 371. to 434. | EB | Li, Fang, et al., 2009 | AC |
11.3 | 301. | A | Stephenson and Malanowski, 1987 | Based on data from 286. to 433. K. See also Stull, 1947.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
286. to 433.0 | 4.86652 | 1922.137 | -38.063 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
4.250 | 209.1 | Domalski and Hearing, 1996 | AC |
4.2531 | 209.1 | Beaumont, Clegg, et al., 1966 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
20.3 | 209.1 | Beaumont, Clegg, et al., 1966 | DH |
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:
B - John E. Bartmess
M - 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: C2H3O2- + C6H14O3 = (C2H3O2- • C6H14O3)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 15.1 ± 1.0 | kcal/mol | N/A | Meot-Ner and Sieck, 1986 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 18.5 | cal/mol*K | PHPMS | Meot-Ner and Sieck, 1986 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 9.6 ± 1.6 | kcal/mol | TDAs | Meot-Ner and Sieck, 1986 | gas phase; B |
(C6H15O3+ • ) +
= (C6H15O3+ •
•
)
By formula: (C6H15O3+ • H3N) + C6H14O3 = (C6H15O3+ • C6H14O3 • H3N)
Bond type: Hydrogen bonds between protonated and neutral organics
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 30.5 | kcal/mol | PHPMS | Meot-Ner (Mautner), Sieck, et al., 1996 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 50.9 | cal/mol*K | PHPMS | Meot-Ner (Mautner), Sieck, et al., 1996 | gas phase; M |
By formula: C3H10N+ + C6H14O3 = (C3H10N+ • C6H14O3)
Bond type: Hydrogen bonds with polydentate bonding in positive ions
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 32.8 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; diglyme; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 40.0 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; diglyme; M |
By formula: C4H5N2+ + C6H14O3 = (C4H5N2+ • C6H14O3)
Bond type: Hydrogen bonds with polydentate bonding in positive ions
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 32.4 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; diglyme; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 36.1 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; diglyme; M |
By formula: C5H5FN+ + C6H14O3 = (C5H5FN+ • C6H14O3)
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; diglyme; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 38.6 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; diglyme; M |
By formula: C5H6N+ + C6H14O3 = (C5H6N+ • C6H14O3)
Bond type: Hydrogen bonds with polydentate bonding in positive ions
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 31.5 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; diglyme; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 36.5 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; diglyme; M |
By formula: C6H14N+ + C6H14O3 = (C6H14N+ • C6H14O3)
Bond type: Hydrogen bonds with polydentate bonding in positive ions
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 39.7 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; diglyme; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 44.6 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; diglyme; M |
(C6H15O3+ • ) +
= (C6H15O3+ •
•
)
By formula: (C6H15O3+ • C6H14O3) + H2O = (C6H15O3+ • H2O • C6H14O3)
Bond type: Hydrogen bond (positive ion to hydride)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 20.6 | kcal/mol | PHPMS | Meot-Ner (Mautner), Sieck, et al., 1994 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 34.7 | cal/mol*K | PHPMS | Meot-Ner (Mautner), Sieck, et al., 1994 | gas phase; M |
By formula: C6H15O3+ + C6H14O3 = (C6H15O3+ • C6H14O3)
Bond type: Hydrogen bonds between protonated and neutral organics
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 21.3 | kcal/mol | PHPMS | Meot-Ner (Mautner), Sieck, et al., 1994 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 38.0 | cal/mol*K | PHPMS | Meot-Ner (Mautner), Sieck, et al., 1994 | gas phase; M |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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
Gas Phase Spectrum
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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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Owner | SRD/NIST Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | EPA-IR VAPOR PHASE LIBRARY |
State | gas |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
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 | Japan AIST/NIMC Database- Spectrum MS-NW- 162 |
NIST MS number | 228683 |
References
Go To: Top, Gas phase thermochemistry data, 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.
Stewart, 2004
Stewart, J.J.P.,
Comparison of the accuracy of semiempirical and some DFT methods for predicting heats of formation,
J. Mol. Model, 2004, 10, 1, 6-10, https://doi.org/10.1007/s00894-003-0157-6
. [all data]
Gutner, Lebedeva, et al., 1980
Gutner, N.M.; Lebedeva, N.D.; Dobychin, S.L.; Kiseleva, N.N.,
Thermochemical study of aliphatic ethers,
J. Appl. Chem. USSR, 1980, 53, 1523-1525. [all data]
Mansson, 1969
Mansson, M.,
Non-bonded oxygen-oxygen interactions in straight-chain compounds,
J. Chem. Thermodyn., 1969, 1, 141-151. [all data]
Baroody and Carpenter, 1972
Baroody, E.E.; Carpenter, G.A.,
Heats of formation of propellant compounds (U), Rpt. Naval Ordnance Systems Command Task No. 331-003/067-1/UR2402-001 for Naval Ordance Station, Indian Head, MD, 1972, 1-9. [all data]
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]
Villamanan, Casanova, et al., 1982
Villamanan, M.A.; Casanova, C.; Roux-Desgranges, G.; Grolier, J.-P.E.,
Thermochemical behavior of mixtures of n-alcohol + aliphatic ether: heat capacities and volumes at 298.15 K,
Thermochim. Acta, 1982, 52, 279-283. [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]
Anonymous, 1982
Anonymous, X.,
Glymes Grant Chemical, 1982, Baton Rouge, LA 1982. [all data]
Wallace and Mathews, 1964
Wallace, W.J.; Mathews, A.L.,
Density, Refractive Indices, Molar Refractions, and Viscosities of Diethylene Glycol Dimethyl Ether-Water Solutions at 25 C,
J. Chem. Eng. Data, 1964, 9, 267-268. [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]
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]
Stephenson and Malanowski, 1987
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]
Stull, 1947
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]
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 and Sieck, 1986
Meot-Ner, M.; Sieck, L.W.,
The ionic hydrogen bond and ion solvation. 5. OH...O- bonds. Gas phase solvation and clustering of alkoxide and carboxylate anions,
J. Am. Chem. Soc., 1986, 108, 7525. [all data]
Meot-Ner (Mautner), Sieck, et al., 1996
Meot-Ner (Mautner), M.; Sieck, L.W.; Liebman, J.F.; Scheiner, S.,
Complexing of the Ammonium Ion by Polyethers. Comparative Complexing Thermochemistry of Ammonium, Hydronium, and Alkali Cations,
J. Phys. Chem., 1996, 100, 16, 6445, https://doi.org/10.1021/jp9514943
. [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, Gas phase thermochemistry data, 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 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 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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