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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

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

Acetic anhydride + Water = 2Acetic acid

By formula: C4H6O3 + H2O = 2C2H4O2

Quantity Value Units Method Reference Comment
Deltar-56.6 ± 4.0kJ/molCmBecker and Maelicke, 1967liquid phase; ALS
Deltar-58.6 ± 0.4kJ/molCmWadso, 1962liquid phase; ALS
Deltar-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
Deltar-113.2 ± 0.46kJ/molCmWadso, 1962liquid phase; ALS
Deltar-163.7 ± 0.3kJ/molCmWadso, 1958liquid phase; Heat of aminolysis; ALS

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

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

Free energy of reaction

DeltarG° (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
Deltar0.0kJ/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
Deltar63.7 ± 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
Deltar-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
Deltar16.7kJ/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
Deltar-43.9kJ/molKinShatynski and Hanesian, 1993solid phase; ALS

Ketene + Acetic acid = Acetic anhydride

By formula: C2H2O + C2H4O2 = C4H6O3

Quantity Value Units Method Reference Comment
Deltar-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 Wärmeflu«beta»kalorimetrie, 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, https://doi.org/10.1002/1521-3765(20000818)6:16<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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