Acetic anhydride

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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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
RCD - Robert C. Dunbar

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Individual Reactions

Acetic anhydride + Water = 2Acetic acid

By formula: C4H6O3 + H2O = 2C2H4O2

Quantity Value Units Method Reference Comment
Δr-56.6 ± 4.0kJ/molCmBecker and Maelicke, 1967liquid phase; ALS
Δr-58.6 ± 0.4kJ/molCmWadso, 1962liquid phase; ALS
Δr-58.4 ± 0.4kJ/molCmConn, Kistiakowsky, et al., 1942liquid phase; Heat of hydrolysis at 303 K; ALS

Acetic anhydride + 1-Butanamine = Acetamide, N-butyl- + Acetic acid

By formula: C4H6O3 + C4H11N = C6H13NO + C2H4O2

Quantity Value Units Method Reference Comment
Δr-113.2 ± 0.46kJ/molCmWadso, 1962liquid phase; ALS
Δr-163.7 ± 0.3kJ/molCmWadso, 1958liquid phase; Heat of aminolysis; ALS

Sodium ion (1+) + Acetic anhydride = (Sodium ion (1+) • Acetic anhydride)

By formula: Na+ + C4H6O3 = (Na+ • C4H6O3)

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
130.298.IMREMcMahon and Ohanessian, 2000Anchor alanine=39.89; RCD

Acetic anhydride + 2Acetic acid, methoxy- = Acetic acid, methoxy-, anhydride + 2Acetic acid

By formula: C4H6O3 + 2C3H6O3 = C6H10O5 + 2C2H4O2

Quantity Value Units Method Reference Comment
Δr0.0kJ/molEqkUtkin, Bogel'fer, et al., 1991liquid phase; NMR; ALS

2Acetic acid = Acetic anhydride + Water

By formula: 2C2H4O2 = C4H6O3 + H2O

Quantity Value Units Method Reference Comment
Δr63.7 ± 1.2kJ/molEqkKnopp, Linnell, et al., 1962liquid phase; ALS

Acetic anhydride + Aniline = Acetamide, N-phenyl- + Acetic acid

By formula: C4H6O3 + C6H7N = C8H9NO + C2H4O2

Quantity Value Units Method Reference Comment
Δr-100.9 ± 0.3kJ/molCmWadso, 1962liquid phase; ALS

Acetyl nitrate + Acetic acid = Acetic anhydride + Nitric acid

By formula: C2H3NO4 + C2H4O2 = C4H6O3 + HNO3

Quantity Value Units Method Reference Comment
Δr16.7kJ/molCmTsvetkov, Shmakov, et al., 1989liquid phase; ALS

Acetic anhydride + Cytidine = Cytidine, N-acetyl- + Acetic acid

By formula: C4H6O3 + C9H13N3O5 = C11H15N3O6 + C2H4O2

Quantity Value Units Method Reference Comment
Δr-43.9kJ/molKinShatynski and Hanesian, 1993solid phase; ALS

Ketene + Acetic acid = Acetic anhydride

By formula: C2H2O + C2H4O2 = C4H6O3

Quantity Value Units Method Reference Comment
Δr-87.5 ± 2.2kJ/molEqkBlake, Davies, et al., 1971gas phase; ALS


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

Becker and Maelicke, 1967
Becker, F.; Maelicke, A., Thermokinetische Messungen nach dem Prinzip der Wärmefluβkalorimetrie, Z. Phys. Chem. (Neue Folge), 1967, 55, 280-295. [all data]

Wadso, 1962
Wadso, I., Heats of aminolysis and hydrolysis of some N-acetyl compounds and of acetic anhydride, Acta Chem. Scand., 1962, 16, 471-478. [all data]

Conn, Kistiakowsky, et al., 1942
Conn, J.B.; Kistiakowsky, G.B.; Roberts, R.M.; Smith, E.A., Heats of organic reactions. XIII. Heats of hydrolysis of some acid anhydrides, J. Am. Chem. Soc., 1942, 64, 1747-17. [all data]

Wadso, 1958
Wadso, I., The heats of aminolysis of n-butyl thiolacetate and acetic anhydride, Acta Chem. Scand., 1958, 12, 635-640. [all data]

McMahon and Ohanessian, 2000
McMahon, T.B.; Ohanessian, G., An Experimental and Ab Initio Study of the Nature of the Binding in Gas-Phase Complexes of Sodium Ions, Chem. Eur. J., 2000, 6, 16, 2931,<2931::AID-CHEM2931>3.0.CO;2-7 . [all data]

Utkin, Bogel'fer, et al., 1991
Utkin, A.Yu.; Bogel'fer, L.Ya.; Chimishkyan, A.L., Reversible reactions in the acidolysis of methyoxyacetic acid by acetic anhydride, Russ. J. Phys. Chem. (Engl. Transl.), 1991, 65, 1049-1059, In original 1974. [all data]

Knopp, Linnell, et al., 1962
Knopp, J.A.; Linnell, W.S.; Child, W.C., Jr., The thermodynamics of the thermal decomposition of acetic acid in the liquid phase, J. Phys. Chem., 1962, 66, 1513-1516. [all data]

Tsvetkov, Shmakov, et al., 1989
Tsvetkov, V.G.; Shmakov, V.A.; Sopin, V.F.; Ivanov, A.V.; Ikonnikov, A.A.; Marchenko, G.N., Enthalpies of reaction of nitric acid with acetic and trifluoroacetic anhydrides, J. Gen. Chem. USSR, 1989, 59, 1220-1222. [all data]

Shatynski and Hanesian, 1993
Shatynski, J.J.; Hanesian, D., Adiabatic kinetic studies of the cytidine/acetic anhydride reaction by utilizing temperature versus time data, Ind. Eng. Chem. Res., 1993, 32, 594-599. [all data]

Blake, Davies, et al., 1971
Blake, P.G.; Davies, H.H.; Speis, A., Reactions of keten. Part II. The thermodynamics of the gas-phase equilibrium: acetic acid + keten = acetic anhydride, J. Chem. Soc. B, 1971, 2050-2052. [all data]


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