Methyl formate
- Formula: C2H4O2
- Molecular weight: 60.0520
- IUPAC Standard InChI: InChI=1S/C2H4O2/c1-4-2-3/h2H,1H3
- IUPAC Standard InChIKey: TZIHFWKZFHZASV-UHFFFAOYSA-N
- CAS Registry Number: 107-31-3
- 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: Formic acid, methyl ester; Methyl methanoate; HCOOCH3; Formiate de methyle; Methylester kyseliny mravenci; Methylformiaat; Methylformiat; Mravencan methylnaty; UN 1243; Methyl ester of formic acid; Methanoic acid methyl ester
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Gas phase thermochemistry 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -336.9 | kJ/mol | N/A | Gladii, Starchevskii, et al., 1990 | Value computed using ΔfHliquid° value of -365.9 kj/mol from Gladii, Starchevskii, et al., 1990 and ΔvapH° value of 29.0 kj/mol from Hine and Klueppet, 1974.; DRB |
| ΔfH°gas | -349.0 | kJ/mol | N/A | Guthrie, 1974 | Value computed using ΔfHliquid° value of -378.0 kj/mol from Guthrie, 1974 and ΔvapH° value of 29.0 kj/mol from Hine and Klueppet, 1974.; DRB |
| ΔfH°gas | -362. | kJ/mol | Cm | Hine and Klueppet, 1974 | ALS |
| ΔfH°gas | -355.5 | kJ/mol | Ccr | Hall and Baldt, 1971 | ALS |
Constant pressure heat capacity of gas
| Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 44.06 | 100. | Chao J., 1986 | p=1 bar. Recommended S(T) and Cp(T) values are in close agreement with statistical values calculated by [ Vay P.-M., 1971] (discrepancies in S(T) do not exceed 1.3 J/mol*K) and value of S(298.15 K)=286.10 J/mol*K determined from high accuracy ab initio calculation [ East A.L.L., 1997].; GT |
| 49.84 | 150. | ||
| 54.18 | 200. | ||
| 61.45 | 273.15 | ||
| 64.38 ± 0.09 | 298.15 | ||
| 64.61 | 300. | ||
| 77.56 | 400. | ||
| 90.29 | 500. | ||
| 101.57 | 600. | ||
| 111.26 | 700. | ||
| 119.53 | 800. | ||
| 126.61 | 900. | ||
| 132.68 | 1000. | ||
| 137.89 | 1100. | ||
| 142.38 | 1200. | ||
| 146.24 | 1300. | ||
| 149.58 | 1400. | ||
| 152.48 | 1500. |
Condensed phase thermochemistry data
Go To: Top, Gas 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:
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 | -365.9 | kJ/mol | Eqk | Gladii, Starchevskii, et al., 1990 | ALS |
| ΔfH°liquid | -378.0 | kJ/mol | Cm | Guthrie, 1974 | Heat of hydrolysis; ALS |
| ΔfH°liquid | -391. | kJ/mol | Cm | Hine and Klueppet, 1974 | ALS |
| ΔfH°liquid | -386.1 | kJ/mol | Ccr | Hall and Baldt, 1971 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -972.61 ± 0.59 | kJ/mol | Ccr | Hall and Baldt, 1971 | Corresponding ΔfHºliquid = -386.1 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 |
|---|---|---|---|
| 120.57 | 298.75 | Zabransky, Hynek, et al., 1987 | T = 293 to 299 K. Unsmoothed experimental datum.; DH |
| 119.7 | 298.15 | Fuchs, 1979 | DH |
| 95.5 | 297. | Hall and Baldt, 1971 | DH |
| 121.3 | 288. | Mehl, 1934 | DH |
| 130. | 298. | Berthelot and Ogier, 1881 | T = 286 to 302 K. Cp given as 0.516 cal/g*K.; 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
ALS - 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
C2H3O2- + =
By formula: C2H3O2- + H+ = C2H4O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | <1606.7 | kJ/mol | CIDT | Graul and Squires, 1988 | gas phase; B |
| ΔrH° | <1639.1 ± 3.8 | kJ/mol | G+TS | DePuy, Grabowski, et al., 1985 | gas phase; HO- + DCO2CH3 -> (M-D)-. ΔHf(MeO- + CO) = -59.7 kcal/mol; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | <1606.7 | kJ/mol | IMRB | DePuy, Grabowski, et al., 1985 | gas phase; HO- + DCO2CH3 -> (M-D)-. ΔHf(MeO- + CO) = -59.7 kcal/mol; B |
C2H3O2- + =
By formula: C2H3O2- + H+ = C2H4O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1637. ± 17. | kJ/mol | G+TS | DePuy, Grabowski, et al., 1985 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1607. ± 17. | kJ/mol | IMRB | DePuy, Grabowski, et al., 1985 | gas phase; B |
+
=
+ 2
By formula: C4H10O3 + H2O = C2H4O2 + 2CH4O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -9.6 ± 1.2 | kJ/mol | Cm | Hine and Klueppet, 1974 | liquid phase; ALS |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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.
Gladii, Starchevskii, et al., 1990
Gladii, S.L.; Starchevskii, M.K.; Pazderskii, Yu.A.; Moiseev, I.I.,
Chemical equilibrium in the methyl formate-water-methanol-formic acid system,
J. Appl. Chem. USSR, 1990, 63, 106-111. [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]
Guthrie, 1974
Guthrie, J.P.,
Hydration of carboxamides. Evaluation of the free energy change for addition of water to acetamide and formamide derivatives,
J. Am. Chem. Soc., 1974, 96, 3608-3615. [all data]
Hall and Baldt, 1971
Hall, H.K., Jr.; Baldt, J.H.,
Thermochemistry of strained-ring bridgehead nitriles and esters,
J. Am. Chem. Soc., 1971, 93, 140-145. [all data]
Chao J., 1986
Chao J.,
Thermodynamic properties of key organic oxygen compounds in the carbon range C1 to C4. Part 2. Ideal gas properties,
J. Phys. Chem. Ref. Data, 1986, 15, 1369-1436. [all data]
Vay P.-M., 1971
Vay P.-M.,
Tables of thermodynamic functions for gaseous methyl formate and methyl acetate,
J. Chim. Phys. Physico-Chim. Biol., 1971, 68, 1757-1758. [all data]
East A.L.L., 1997
East A.L.L.,
Ab initio statistical thermodynamical models for the computation of third-law entropies,
J. Chem. Phys., 1997, 106, 6655-6674. [all data]
Zabransky, Hynek, et al., 1987
Zabransky, M.; Hynek, V.; Finkeova-Hastabova, J.; Vesely, F.,
Heat capacities of six liquid esters as a function of temperature,
Coll. Czech. Chem. Comm., 1987, 52, 251-256. [all data]
Fuchs, 1979
Fuchs, R.,
Heat capacities of some liquid aliphatic, alicyclic, and aromatic esters at 298.15 K,
J. Chem. Thermodyn., 1979, 11, 959-961. [all data]
Mehl, 1934
Mehl, W.,
Die spezifische Wärme einiger flüssiger Kältemittel,
Z. ges. Kalte-Ind., 1934, 41, 152-153. [all data]
Berthelot and Ogier, 1881
Berthelot, M.; Ogier, J.,
Recherches sur les ethers formiques,
Ann. chim. et phys., 1881, 23(5), 201-209. [all data]
Graul and Squires, 1988
Graul, S.T.; Squires, R.R.,
On the Existence of Alkyl Carbanions in the Gas Phase,
J. Am. Chem. Soc., 1988, 110, 2, 607, https://doi.org/10.1021/ja00210a054
. [all data]
DePuy, Grabowski, et al., 1985
DePuy, C.H.; Grabowski, J.J.; Bierbaum, V.M.; Ingemann, S.; Nibbering, N.M.M.,
Gas-phase reactions of anions with methyl formate and N,N-dimethylformamide,
J. Am. Chem. Soc., 1985, 107, 1093. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid 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 ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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