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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Condensed phase thermochemistry data
Go To: Top, Phase change data, Reaction thermochemistry data, 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -193.53 | kcal/mol | Ccr | Baroody and Carpenter, 1972 | ALS |
ΔfH°liquid | -193.05 | kcal/mol | Ccr | Zimmer, Baroody, et al., 1968 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -712.55 | kcal/mol | Ccr | Zimmer, Baroody, et al., 1968 | Corresponding ΔfHºliquid = -193.33 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -713.4 ± 2.0 | kcal/mol | Ccr | Zimmer, Robb, et al., 1966 | Reanalyzed by Cox and Pilcher, 1970, Original value = -713.59 kcal/mol; Corresponding ΔfHºliquid = -192.51 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
62.31 | 298. | von Reis, 1881 | T = 294 to 472 K.; DH |
Phase change data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, 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:
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 | 21.12 | atm | N/A | Steele, Chirico, et al., 1994 | Uncertainty assigned by TRC = 0.04 atm; 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 (atm) | Reference | Comment |
---|---|---|---|
370.2 | 0.026 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
12.9 | 358. | A | Stephenson and Malanowski, 1987 | Based on data from 343. to 457. K.; AC |
14.9 | 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 (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
320.6 to 458.9 | 5.97587 | 2537.141 | -34.06 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Reaction thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, 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: 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° | -1189.33 ± 0.56 | kcal/mol | Ccr | Baroody and Carpenter, 1973 | solid phase; Corrected for CODATA value of ΔfH; HF.100H2O |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.