Ethyl orthoformate
- Formula: C7H16O3
- Molecular weight: 148.2001
- IUPAC Standard InChI: InChI=1S/C7H16O3/c1-4-8-7(9-5-2)10-6-3/h7H,4-6H2,1-3H3
- IUPAC Standard InChIKey: GKASDNZWUGIAMG-UHFFFAOYSA-N
- CAS Registry Number: 122-51-0
- 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. - Species with the same structure:
- Other names: Ethane, 1,1',1''-[methylidynetris(oxy)]tris-; Orthoformic acid, triethyl ester; Aethon; Ethone; Orthoformic acid ethyl ester; Triethoxymethane; Triethyl orthoformate; Triethoxmethane; Ethyl formate(ortho); Ethylester kyseliny orthomravenci; Methane, triethoxy-; Orthomravencan ethylnaty; 1,1',1''-(Methylidynetris(oxy))tris(ethane); Triethylester kyseliny orthomravenci; UN 2524; Triethyl ester of orthoformic acid; NSC 5289; 1-(Diethoxymethoxy)ethane
- Information on this page:
- Other data available:
- 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.
Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -150.7 | kcal/mol | N/A | Gutner, Lebedeva, et al., 1980 | Value computed using ΔfHliquid° value of -675.8±0.8 kj/mol from Gutner, Lebedeva, et al., 1980 and ΔvapH° value of 45.2 kj/mol from Hine and Klueppet, 1974.; DRB |
| ΔfH°gas | -153.4 | kcal/mol | Cm | Hine and Klueppet, 1974 | Heat of hydrolysis; ALS |
| ΔfH°gas | -151.84 ± 0.90 | kcal/mol | Ccb | Pihlaja and Tuomi, 1971 | ALS |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | -161.5 ± 0.2 | kcal/mol | Ccb | Gutner, Lebedeva, et al., 1980 | |
| ΔfH°liquid | -164.2 | kcal/mol | Cm | Hine and Klueppet, 1974 | Heat of hydrolysis |
| ΔfH°liquid | -162.84 ± 0.70 | kcal/mol | Ccb | Pihlaja and Tuomi, 1971 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -1043.4 ± 0.2 | kcal/mol | Ccb | Gutner, Lebedeva, et al., 1980 | Corresponding ΔfHºliquid = -161.5 kcal/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°liquid | -1042.04 ± 0.70 | kcal/mol | Ccb | Pihlaja and Tuomi, 1971 | Corresponding ΔfHºliquid = -162.84 kcal/mol (simple calculation by NIST; no Washburn corrections) |
Phase change data
Go To: Top, Gas phase thermochemistry data, 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 419.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
| Tboil | 417. to 419. | K | N/A | Frinton Laboratories Inc., 1986 | BS |
| Tboil | 418.9 | K | N/A | Lecat, 1943 | Uncertainty assigned by TRC = 0.3 K; TRC |
| Tboil | 418. | K | N/A | Pfeiffer and Adkins, 1931 | Uncertainty assigned by TRC = 2.5 K; TRC |
| Tboil | 419. | K | N/A | Carswell and Adkins, 1928 | Uncertainty assigned by TRC = 2. K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 197.1 | K | N/A | Timmermans, 1922 | Uncertainty assigned by TRC = 0.4 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 11.1 ± 0.6 | kcal/mol | AVG | N/A | Average of 7 values; Individual data points |
Enthalpy of vaporization
| ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 11.7 | 308. | A | Stephenson and Malanowski, 1987 | Based on data from 293. to 323. K.; AC |
| 11.3 | 293. | A | Stephenson and Malanowski, 1987 | Based on data from 278. to 419. 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 |
|---|---|---|---|---|---|
| 278.7 to 419. | 4.83581 | 1821.195 | -42.668 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, 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
+
=
+ 2
By formula: C7H16O3 + H2O = C3H6O2 + 2C2H6O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -3.17 ± 0.19 | kcal/mol | Cm | Hine and Klueppet, 1974 | liquid phase; Heat of hydrolysis |
References
Go To: Top, Gas phase thermochemistry data, 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.
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]
Hine and Klueppet, 1974
Hine, J.; Klueppet, A.W.,
Structural effects on rates and equilibria. XVIII. Thermodynamic stability of ortho esters,
J. Am. Chem. Soc., 1974, 96, 2924-2929. [all data]
Pihlaja and Tuomi, 1971
Pihlaja, K.; Tuomi, M.,
Bond-bond interactions in organic oxygen compounds. Part V. Enthalpies of formation of methyl and ethyl orthoformates and the contributory group increments. The magnitude of the so-called rabbit-ear effect in acyclic oxygen compounds,
Acta Chem. Scand., 1971, 25, 465-469. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Frinton Laboratories Inc., 1986
Frinton Laboratories Inc.,
Catalog Number 11, Frinton Laboratories Inc., Vineland, NJ, 1986, 99. [all data]
Lecat, 1943
Lecat, M.,
Negative and other Azeotropes,
C. R. Hebd. Seances Acad. Sci., 1943, 217, 242. [all data]
Pfeiffer and Adkins, 1931
Pfeiffer, G.J.; Adkins, H.,
The Relation of the Structure of Ketones to Their Reactivity and Affinity in Acetal Formation II.,
J. Am. Chem. Soc., 1931, 53, 1043. [all data]
Carswell and Adkins, 1928
Carswell, H.E.; Adkins, H.,
The Relation of the Structure of Ketones to their Reactivity and Affinity in Acetal Formation,
J. Am. Chem. Soc., 1928, 50, 235. [all data]
Timmermans, 1922
Timmermans, J.,
Investigation of the Freezing Point of Organic Substances VII,
Bull. Soc. Chim. Belg., 1922, 31, 389. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
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 ΔrH° Enthalpy 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
- 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.