Ethanedioic acid, diethyl ester
- Formula: C6H10O4
- Molecular weight: 146.1412
- IUPAC Standard InChIKey: WYACBZDAHNBPPB-UHFFFAOYSA-N
- CAS Registry Number: 95-92-1
- 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: Oxalic acid, diethyl ester; Diethyl ethanedioate; Diethyl oxalate; Ethyl oxalate; C2H5OCOCOOC2H5; Diethylester kyseliny stavelove; UN 2525; Diethyl ester of oxalic acid; Oxalic ether; Ethanedioic acid, 1,2-diethyl ester; NSC 8851
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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 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 | -809.73 | kJ/mol | Ccr | Baroody and Carpenter, 1972 | ALS |
ΔfH°liquid | -807.72 | kJ/mol | Ccr | Zimmer, Baroody, et al., 1968 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -2981.3 | kJ/mol | Ccr | Zimmer, Baroody, et al., 1968 | Corresponding ΔfHºliquid = -808.89 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -2984.7 ± 8.4 | kJ/mol | Ccr | Zimmer, Robb, et al., 1966 | Reanalyzed by Cox and Pilcher, 1970, Original value = -2985.7 kJ/mol; Corresponding ΔfHºliquid = -805.46 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
260.7 | 298. | von Reis, 1881 | T = 294 to 472 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 458.9 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 458.8 | K | N/A | Lecat, 1943 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tboil | 458.8 | K | N/A | Lecat, 1943, 2 | Uncertainty assigned by TRC = 0.25 K; TRC |
Tboil | 458.15 | K | N/A | Timmermans, 1911 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tboil | 458.85 | K | N/A | Kahlbaum, 1884 | Uncertainty assigned by TRC = 1.5 K; b.p. listed as 785.3, but obviously a misprint; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 232.35 | K | N/A | Timmermans, 1952 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 232.55 | K | N/A | Timmermans, 1911 | Uncertainty assigned by TRC = 0.4 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 618. | K | N/A | Steele, Chirico, et al., 1994 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 21.40 | bar | N/A | Steele, Chirico, et al., 1994 | Uncertainty assigned by TRC = 0.04 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 2.212 | mol/l | N/A | Steele, Chirico, et al., 1994 | Uncertainty assigned by TRC = 0.02 mol/l; TRC |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
370.2 | 0.027 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
53.9 | 358. | A | Stephenson and Malanowski, 1987 | Based on data from 343. to 457. K.; AC |
62.3 | 335. | A | Stephenson and Malanowski, 1987 | Based on data from 320. to 459. K. See also Stull, 1947.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
320.6 to 458.9 | 5.98158 | 2537.141 | -34.06 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
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
By formula: C4H4F2N6O10 + 6O2 + C6H10O4 = 10CO2 + 2HF + 3N2 + 6H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -4976.2 ± 2.3 | kJ/mol | Ccr | Baroody and Carpenter, 1973 | solid phase; Corrected for CODATA value of ΔfH; HF.100H2O |
Gas phase ion energetics 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: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.8 | PE | McGlynn and Meeks, 1976 | |
10.19 | PE | McGlynn and Meeks, 1976 | Vertical value |
IR Spectrum
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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
Gas Phase Spectrum
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Additional Data
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Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Sadtler Research Labs Under US-EPA Contract |
State | 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
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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 | Chuck Anderson, Aldrich Chemical Co. |
NIST MS number | 107320 |
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 |
---|---|---|---|---|---|
Packed | DC-200 | 120. | 940. | Reymond, Mueggler-Chavan, et al., 1966 | Celite; Column length: 4. m |
Kovats' RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Supelcowax-10 | 1496. | Wong and Teng, 1994 | He, 35. C @ 5. min, 3. K/min, 200. C @ 20. min; Column length: 60. m; Column diameter: 0.25 mm |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | RTX-5 | 940. | Ádámová, Orinák, et al., 2005 | 30. m/0.25 mm/0.25 μm, N2, 40. C @ 2. min, 5. K/min, 300. C @ 10. min |
Packed | SE-30 | 948. | van den Dool and Kratz, 1963 | Celite; Tstart: 75. C; Tend: 228. C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | RTX-5 | 938. | Setkova, Risticevic, et al., 2007 | 10. m/0.18 mm/0.2 μm, He, 40. C @ 0.5 min, 50. K/min, 275. C @ 0.5 min |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | RTX-5 | 940. | Ádámová, Orinák, et al., 2005 | 30. m/0.25 mm/0.25 μm, N2; Program: not specified |
Capillary | OV-101 | 948. | Zenkevich and Malamakhov, 1987 | He; Column length: 50. m; Column diameter: 0.24 mm; Program: not specified |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 1530. | Vinogradov, 2004 | 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.
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]
Zimmer, Baroody, et al., 1968
Zimmer, M.F.; Baroody, E.E.; Carpenter, G.A.; Robb, R.A.,
Heat of formation of hydroxylammonium perchlorate by combustion calorimetry,
J. Chem. Eng. Data, 1968, 13, 212-214. [all data]
Zimmer, Robb, et al., 1966
Zimmer, M.F.; Robb, R.A.; Baroody, E.E.; Carpenter, G.A.,
Heat of formation and other properties of trinitrofluoromethane,
J. Chem. Eng. Data, 1966, 11, 577-579. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
von Reis, 1881
von Reis, M.A.,
Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht,
Ann. Physik [3], 1881, 13, 447-464. [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]
Lecat, 1943
Lecat, M.,
Negative and other Azeotropes,
C. R. Hebd. Seances Acad. Sci., 1943, 217, 242. [all data]
Lecat, 1943, 2
Lecat, M.,
Azeotropes of Ethyl Urethane and other Azeotropes,
C. R. Hebd. Seances Acad. Sci., 1943, 217, 273. [all data]
Timmermans, 1911
Timmermans, J.,
Researches on the freezing point of organic liquid compounds,
Bull. Soc. Chim. Belg., 1911, 25, 300. [all data]
Kahlbaum, 1884
Kahlbaum, G.W.A.,
The dependence of Boiling Temperature on Air Pressure,
Ber. Dtsch. Chem. Ges., 1884, 17, 1245. [all data]
Timmermans, 1952
Timmermans, J.,
Freezing points of organic compounds. VVI New determinations.,
Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]
Steele, Chirico, et al., 1994
Steele, W.V.; Chirico, R.D.; Hossenlopp, I.A.; Knipmeyer, S.E.; Nguyen, A.; Smith, N.K.,
DIPPR project 871. Determination of ideal-gas enthalpies of formation for key compounds. The 1990 project results,
Experimental Results for DIPPR 1990-91 Projects on Phase Equilibria and Pure Component Properties, 1994, 1994, DIPPR Data Ser. No. 2, p. 188-215. [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]
Baroody and Carpenter, 1973
Baroody, E.E.; Carpenter, G.A.,
Enthalpies of formation of some fluorodinitroethyl derivatives and 2,2',4,4',6,6'-hexanitroazobenzene,
J. Chem. Eng. Data, 1973, 18, 28-36. [all data]
McGlynn and Meeks, 1976
McGlynn, S.P.; Meeks, J.L.,
Photoelectron spectra of carbonyls, carbonates, oxalates and esterification effects,
J. Electron Spectrosc. Relat. Phenom., 1976, 8, 85. [all data]
Reymond, Mueggler-Chavan, et al., 1966
Reymond, D.; Mueggler-Chavan, F.; Viani, R.; Vuataz, L.; Egli, R.H.,
Gas chromatographic analysis of steam volatile aroma constituents: application to coffee, tea and cocoa aromas,
J. Gas Chromatogr., 1966, 4, 1, 28-31, https://doi.org/10.1093/chromsci/4.1.28
. [all data]
Wong and Teng, 1994
Wong, K.C.; Teng, Y.E.,
Volatile Components of Mimusops elengi L. Flowers,
J. Essent. Oil Res., 1994, 6, 5, 453-458, https://doi.org/10.1080/10412905.1994.9698425
. [all data]
Ádámová, Orinák, et al., 2005
Ádámová, M.; Orinák, A.; Halás, L.,
Retention indices as identification tool in pyrolysis-capillary gas chromatography,
J. Chromatogr. A, 2005, 1087, 1-2, 131-141, https://doi.org/10.1016/j.chroma.2005.01.003
. [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]
Setkova, Risticevic, et al., 2007
Setkova, L.; Risticevic, S.; Pawliszyn, J.,
Rapid headspace solid-phase microextraction-gas chromatographic?time-of-flight mass spectrometric method for qualitative profiling of ice wine volatile fraction II: Classification of Canadian and Czech ice wines using statistical evaluation of the data,
J. Chromatogr. A, 2007, 1147, 2, 224-240, https://doi.org/10.1016/j.chroma.2007.02.052
. [all data]
Zenkevich and Malamakhov, 1987
Zenkevich, I.G.; Malamakhov, A.C.,
Evaluation of Molecular Weights of Organic Compounds based on Retention Parameters at Chromato-Spectral Analysys. Additional Criterion of Molecular Ions' Identification,
Vestn. St. Petersb. Univ. Ser. 4: Fiz. Khim, 1987, 2, 101-106. [all data]
Vinogradov, 2004
Vinogradov, B.A.,
Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [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 Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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