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Ethyl Acetate

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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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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

C3H9Si+ + Ethyl Acetate = (C3H9Si+ bullet Ethyl Acetate)

By formula: C3H9Si+ + C4H8O2 = (C3H9Si+ bullet C4H8O2)

Quantity Value Units Method Reference Comment
Deltar204.kJ/molPHPMSWojtyniak and Stone, 1986gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)H2O, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar131.J/mol*KN/AWojtyniak and Stone, 1986gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)H2O, Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
142.468.PHPMSWojtyniak and Stone, 1986gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)H2O, Entropy change calculated or estimated; M

C3H9Sn+ + Ethyl Acetate = (C3H9Sn+ bullet Ethyl Acetate)

By formula: C3H9Sn+ + C4H8O2 = (C3H9Sn+ bullet C4H8O2)

Quantity Value Units Method Reference Comment
Deltar168.kJ/molPHPMSStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar140.J/mol*KN/AStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
95.8525.PHPMSStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M

C4H7O2- + Hydrogen cation = Ethyl Acetate

By formula: C4H7O2- + H+ = C4H8O2

Quantity Value Units Method Reference Comment
Deltar1555. ± 17.kJ/molG+TSHaas, Giblin, et al., 1998gas phase; From transesterification equilibria; B
Deltar1543. ± 5.0kJ/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase; B
Quantity Value Units Method Reference Comment
Deltar1527. ± 17.kJ/molIMREHaas, Giblin, et al., 1998gas phase; From transesterification equilibria; B

C4H9O2+ + Ethyl Acetate = (C4H9O2+ bullet Ethyl Acetate)

By formula: C4H9O2+ + C4H8O2 = (C4H9O2+ bullet C4H8O2)

Bond type: Hydrogen bonds of the type OH-O between organics

Quantity Value Units Method Reference Comment
Deltar122.kJ/molPHPMSSzulejko and McMahon, 1991gas phase; M
Quantity Value Units Method Reference Comment
Deltar145.J/mol*KPHPMSSzulejko and McMahon, 1991gas phase; M

Nitric oxide anion + Ethyl Acetate = (Nitric oxide anion bullet Ethyl Acetate)

By formula: NO- + C4H8O2 = (NO- bullet C4H8O2)

Quantity Value Units Method Reference Comment
Deltar174.kJ/molICRReents and Freiser, 1981gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M

Acetic acid ethenyl ester + Hydrogen = Ethyl Acetate

By formula: C4H6O2 + H2 = C4H8O2

Quantity Value Units Method Reference Comment
Deltar-129. ± 4.6kJ/molChydVilcu and Perisanu, 1980liquid phase; ALS
Deltar-130.2 ± 0.3kJ/molChydDolliver, Gresham, et al., 1938gas phase; At 355 °K; ALS

Acetylimidazole diethyl acetal + Water = Ethyl Acetate + 1H-Imidazole + Ethanol

By formula: C9H16N2O2 + H2O = C4H8O2 + C3H4N2 + C2H6O

Quantity Value Units Method Reference Comment
Deltar-44.69 ± 0.67kJ/molCmGuthrie and Pike, 1987liquid phase; Heat of hydrolysis; ALS

Ethyl Acetate + Water = Ethanol + Acetic acid

By formula: C4H8O2 + H2O = C2H6O + C2H4O2

Quantity Value Units Method Reference Comment
Deltar3.7 ± 0.2kJ/molCmWadso, 1958liquid phase; Heat of hydrolysis; ALS

Ethanol + Acetic acid = Ethyl Acetate + Water

By formula: C2H6O + C2H4O2 = C4H8O2 + H2O

Quantity Value Units Method Reference Comment
Deltar16.6 ± 0.3kJ/molEqkHalford and Brundage, 1942gas phase; At 313 K; ALS

Hydrogen + Ethyl Acetate = 2Ethanol

By formula: H2 + C4H8O2 = 2C2H6O

Quantity Value Units Method Reference Comment
Deltar-74.98 ± 0.54kJ/molCmWiberg, Crocker, et al., 1991liquid phase; ALS

Ketene + Ethanol = Ethyl Acetate

By formula: C2H2O + C2H6O = C4H8O2

Quantity Value Units Method Reference Comment
Deltar-152.5kJ/molCmRice and Greenberg, 1934gas phase; ALS

References

Go To: Top, Reaction thermochemistry data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Wojtyniak and Stone, 1986
Wojtyniak, A.C.M.; Stone, A.J., A High-Pressure Mass Spectrometric Study of the Bonding of Trimethylsilylium to Oxygen and Aromatic Bases, Can. J. Chem., 1986, 74, 59. [all data]

Stone and Splinter, 1984
Stone, J.A.; Splinter, D.E., A high-pressure mass spectrometric study of the binding of (CH3)3Sn+ to lewis bases in the gas phase, Int. J. Mass Spectrom. Ion Processes, 1984, 59, 169. [all data]

Haas, Giblin, et al., 1998
Haas, G.W.; Giblin, D.E.; Gross, M.L., The Mechanism and Thermodynamics of Transesterification of Acetate-Ester Enolates in the Gas Phase, Int. J. Mass Spectrom. Ion Proc., 1998, 172, 1-2, 25, https://doi.org/10.1016/S0168-1176(97)83245-4 . [all data]

Muftakhov, Vasil'ev, et al., 1999
Muftakhov, M.V.; Vasil'ev, Y.V.; Mazunov, V.A., Determination of electron affinity of carbonyl radicals by means of negative ion mass spectrometry, Rapid Commun. Mass Spectrom., 1999, 13, 12, 1104-1108, https://doi.org/10.1002/(SICI)1097-0231(19990630)13:12<1104::AID-RCM619>3.0.CO;2-C . [all data]

Szulejko and McMahon, 1991
Szulejko, J.E.; McMahon, T.B., A Pulsed Electron Beam, Variable Temperature, High Pressure Mass Spectrometric Reevaluation of the Proton Affinity Difference Between 2-Methylpropene and Ammonia, Int. J. Mass Spectrom. Ion Proc., 1991, 109, 279, https://doi.org/10.1016/0168-1176(91)85109-Y . [all data]

Reents and Freiser, 1981
Reents, W.D.; Freiser, B.S., Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes, J. Am. Chem. Soc., 1981, 103, 2791. [all data]

Farid and McMahon, 1978
Farid, R.; McMahon, T.B., Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy, Int. J. Mass Spectrom. Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0 . [all data]

Vilcu and Perisanu, 1980
Vilcu, R.; Perisanu, S., The ideal gas state enthalpies of formation of some monomers, Rev. Roum. Chim., 1980, 25, 619-624. [all data]

Dolliver, Gresham, et al., 1938
Dolliver, M.A.; Gresham, T.L.; Kistiakowsky, G.B.; Smith, E.A.; Vaughan, W.E., Heats of organic reactions. VI. Heats of hydrogenation of some oxygen-containing compounds, J. Am. Chem. Soc., 1938, 60, 440-450. [all data]

Guthrie and Pike, 1987
Guthrie, J.P.; Pike, D.C., Hydration of acylimidazoles: tetrahedral intermediates in acylimidazole hydrolysis and nucleophilic attack by imidazole on esters. The question of concerted mechanisms for acyl transfers, Can. J. Chem., 1987, 65, 1951-1969. [all data]

Wadso, 1958
Wadso, I., The heats of hydrolysis of some alkyl acetates, Acta Chem. Scand., 1958, 12, 630-633. [all data]

Halford and Brundage, 1942
Halford, J.O.; Brundage, D., The vapor phase esterification equilibrium, J. Am. Chem. Soc., 1942, 64, 36-40. [all data]

Wiberg, Crocker, et al., 1991
Wiberg, K.B.; Crocker, L.S.; Morgan, K.M., Thermochemical studies of carbonyl compounds. 5. Enthalpies of reduction of carbonyl groups, J. Am. Chem. Soc., 1991, 113, 3447-3450. [all data]

Rice and Greenberg, 1934
Rice, F.O.; Greenberg, J., Ketene. III. Heat of formation and heat of reaction with alcohols, J. Am. Chem. Soc., 1934, 38, 2268-2270. [all data]


Notes

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