Ethanedioic acid, dimethyl ester
- Formula: C4H6O4
- Molecular weight: 118.0880
- IUPAC Standard InChI: InChI=1S/C4H6O4/c1-7-3(5)4(6)8-2/h1-2H3
- IUPAC Standard InChIKey: LOMVENUNSWAXEN-UHFFFAOYSA-N
- CAS Registry Number: 553-90-2
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: Oxalic acid, dimethyl ester; Dimethyl oxalate; Methyl oxalate; CH3OCOCOOCH3; Dimethyl ester of oxalic acid; Ethanedioc acid dimethyl ester
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Gas phase thermochemistry data
Go To: Top, Reaction thermochemistry data, 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -169.52 ± 0.13 | kcal/mol | Ccb | Anthoney, Carson, et al., 1976 | See Anthoney, Carson, et al., 1975; ALS |
| ΔfH°gas | -169.6 | kcal/mol | N/A | Anthoney, Finch, et al., 1975 | Value computed using ΔfHsolid° value of -756.7±0.3 kj/mol from Anthoney, Finch, et al., 1975 and ΔsubH° value of 47.0 kj/mol from Anthoney, Carson, et al., 1976.; DRB |
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: 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
+ 2
=
+ 2
By formula: C4H6O4 + 2H2O = C2H2O4 + 2CH4O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 4.165 ± 0.016 | kcal/mol | Cm | Anthoney, Finch, et al., 1975 | solid phase; solvent: Water; Hydrolysis |
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
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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 | Japan AIST/NIMC Database- Spectrum MS-NW-5045 |
| NIST MS number | 228095 |
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
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | SE-54 | 140. | 824. | Grigor'eva, Vasil'ev, et al., 1993 | 15. m/0.28 mm/2.4 μm, Ar |
| Capillary | SE-54 | 160. | 819. | Grigor'eva, Vasil'ev, et al., 1993 | 15. m/0.28 mm/2.4 μm, Ar |
| Capillary | SE-54 | 180. | 817. | Grigor'eva, Vasil'ev, et al., 1993 | 15. m/0.28 mm/2.4 μm, Ar |
Kovats' RI, polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | PEG-40M | 120. | 1382. | Grigor'eva, Vasil'ev, et al., 1993 | 40. m/0.25 mm/0.10 μm, Ar |
| Capillary | PEG-40M | 120. | 1389. | Grigor'eva, Vasil'ev, et al., 1993 | 40. m/0.25 mm/0.10 μm, Ar |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5 | 826. | Wu, Zorn, et al., 2007 | 30. m/0.32 mm/0.25 μm, He, 40. C @ 2. min, 5. K/min, 250. C @ 5. min |
| Packed | SE-30 | 837. | van den Dool and Kratz, 1963 | Celite; Tstart: 75. C; Tend: 228. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Packed | SE-30 | 800. | Peng, Ding, et al., 1988 | Supelcoport; Chromosorb; Column length: 3.05 m; Program: 40C(5min) => 10C/min => 200C or 250C (60min) |
Van Den Dool and Kratz RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | ZB-Wax | 1409. | Wu, Zorn, et al., 2007 | 30. m/0.32 mm/0.25 μm, He, 40. C @ 2. min, 5. K/min, 250. C @ 5. min |
| Packed | Carbowax 20M | 1382. | van den Dool and Kratz, 1963 | Celite 545, 4.6 K/min; Tstart: 75. C; Tend: 228. C |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5 | 800. | N/A | 30. m/0.32 mm/0.25 μm, Helium, 40. C @ 2. min, 5. K/min, 250. C @ 5. min |
| Capillary | HP-5 | 826. | N/A | 30. m/0.32 mm/0.25 μm, Helium, 40. C @ 2. min, 5. K/min, 250. C @ 5. min |
| Capillary | DB-5 | 800. | Wu, Krings, et al., 2005 | 30. m/0.32 mm/0.25 μm, He, 40. C @ 2. min, 5. K/min, 250. C @ 10. min |
Normal alkane RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | ZB-Wax | 1395. | N/A | 30. m/0.32 mm/0.25 μm, Helium, 40. C @ 2. min, 5. K/min, 250. C @ 5. min |
| Capillary | ZB-Wax | 1409. | N/A | 30. m/0.32 mm/0.25 μm, Helium, 40. C @ 2. min, 5. K/min, 250. C @ 5. min |
| Capillary | ZB-Wax | 1395. | Wu, Krings, et al., 2005 | 30. m/0.32 mm/0.25 μm, He, 40. C @ 2. min, 5. K/min, 250. C @ 10. min |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, 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.
Anthoney, Carson, et al., 1976
Anthoney, M.E.; Carson, A.S.; Laye, P.G.; Yrekli, M.,
The enthalpy of formation of dimethyl oxalate,
J. Chem. Thermodyn., 1976, 8, 1009-1010. [all data]
Anthoney, Carson, et al., 1975
Anthoney, M.E.; Carson, A.S.; Laye, P.G.,
The thermochemistry of formates and oxalates,
Conf. Int. Thermodyn. Chim. C.R. 4th, 1975, 1, 99-103. [all data]
Anthoney, Finch, et al., 1975
Anthoney, M.E.; Finch, A.; Stephens, M.,
The solution of dimethyl oxalate and oxalic acid in water and alkali. Standard enthalpy of formation of dimethyl oxalate,
Thermochim. Acta, 1975, 12, 427-431. [all data]
Grigor'eva, Vasil'ev, et al., 1993
Grigor'eva, D.N.; Vasil'ev, A.V.; Golovnya, R.V.,
Effect of the temperature on the retention indices in homologous series of bifunctional compounds under capillary gas chromatography conditions,
J. Anal. Chem. USSR (Engl. Transl.), 1993, 48, 7, 817-822. [all data]
Wu, Zorn, et al., 2007
Wu, S.; Zorn, H.; Krings, U.; Berger, R.G.,
Volatiles from submerged and surface-cultured beefsteak fungus, Fistulina hepatica,
Flavour Fragr. J., 2007, 22, 1, 53-60, https://doi.org/10.1002/ffj.1758
. [all data]
van den Dool and Kratz, 1963
van den Dool, H.; Kratz, P. Dec.,
A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography,
J. Chromatogr., 1963, 11, 463-471, https://doi.org/10.1016/S0021-9673(01)80947-X
. [all data]
Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C.,
Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns,
J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8
. [all data]
Wu, Krings, et al., 2005
Wu, S.; Krings, U.; Zorn, H.; Berger, R.G.,
Volatile compounds from the fruiting bodies of beefsteak fungus Fistulina hepatica (Schaeffer: Fr.) Fr.,
Food Chem., 2005, 92, 2, 221-226, https://doi.org/10.1016/j.foodchem.2004.07.013
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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