Acetic anhydride
- Formula: C4H6O3
- Molecular weight: 102.0886
- IUPAC Standard InChI: InChI=1S/C4H6O3/c1-3(5)7-4(2)6/h1-2H3
- IUPAC Standard InChIKey: WFDIJRYMOXRFFG-UHFFFAOYSA-N
- CAS Registry Number: 108-24-7
- 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: Acetic acid, anhydride; Acetic oxide; Acetyl anhydride; Acetyl ether; Acetyl oxide; Ethanoic anhydride; (CH3CO)2O; Ethanoic anhydrate; Acetanhydride; Anhydride acetique; Anhydrid kyseliny octove; Anidride acetica; Azijnzuuranhydride; Essigsaeureanhydrid; Octowy bezwodnik; UN 1715; Acetyl acetate; Acetic acid, 1,1'-anhydride
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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 by: Glushko Thermocenter, Russian Academy of Sciences, Moscow
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| S°gas | 389.95 | J/mol*K | N/A | Stull D.R., 1969 |
Constant pressure heat capacity of gas
| Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 99.50 | 298.15 | Stull D.R., 1969 | Selected values were based on an approximation of heat capacities from Cp(T) values of acetic acid. |
| 100.04 | 300. | ||
| 129.12 | 400. | ||
| 153.89 | 500. | ||
| 174.14 | 600. | ||
| 191.38 | 700. | ||
| 204.64 | 800. | ||
| 216.06 | 900. | ||
| 226.40 | 1000. |
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 | -625.0 ± 3.4 | kJ/mol | Cm | Guthrie, 1974 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -628.4 ± 3.3 kJ/mol; Heat of hydrolysis[kcal/mol]=-40.6±0.80; ALS |
Constant pressure heat capacity of liquid
| Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 168.2 | 303.2 | Phillip, 1939 | DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase 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
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
+
= 2
By formula: C4H6O3 + H2O = 2C2H4O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -56.6 ± 4.0 | kJ/mol | Cm | Becker and Maelicke, 1967 | liquid phase; ALS |
| ΔrH° | -58.6 ± 0.4 | kJ/mol | Cm | Wadso, 1962 | liquid phase; ALS |
| ΔrH° | -58.4 ± 0.4 | kJ/mol | Cm | Conn, Kistiakowsky, et al., 1942 | liquid phase; Heat of hydrolysis at 303 K; ALS |
+
=
+
By formula: C4H6O3 + C4H11N = C6H13NO + C2H4O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -113.2 ± 0.46 | kJ/mol | Cm | Wadso, 1962 | liquid phase; ALS |
| ΔrH° | -163.7 ± 0.3 | kJ/mol | Cm | Wadso, 1958 | liquid phase; Heat of aminolysis; ALS |
+
= (
•
)
By formula: Na+ + C4H6O3 = (Na+ • C4H6O3)
Free energy of reaction
| ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 130. | 298. | IMRE | McMahon and Ohanessian, 2000 | Anchor alanine=39.89; RCD |
+ 2
=
+ 2
By formula: C4H6O3 + 2C3H6O3 = C6H10O5 + 2C2H4O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 0.0 | kJ/mol | Eqk | Utkin, Bogel'fer, et al., 1991 | liquid phase; NMR; ALS |
2 =
+
By formula: 2C2H4O2 = C4H6O3 + H2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 63.7 ± 1.2 | kJ/mol | Eqk | Knopp, Linnell, et al., 1962 | liquid phase; ALS |
+
=
+
By formula: C4H6O3 + C6H7N = C8H9NO + C2H4O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -100.9 ± 0.3 | kJ/mol | Cm | Wadso, 1962 | liquid phase; ALS |
+
=
+
By formula: C2H3NO4 + C2H4O2 = C4H6O3 + HNO3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 16.7 | kJ/mol | Cm | Tsvetkov, Shmakov, et al., 1989 | liquid phase; ALS |
+
=
+
By formula: C4H6O3 + C9H13N3O5 = C11H15N3O6 + C2H4O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -43.9 | kJ/mol | Kin | Shatynski and Hanesian, 1993 | solid phase; ALS |
+
=
By formula: C2H2O + C2H4O2 = C4H6O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -87.5 ± 2.2 | kJ/mol | Eqk | Blake, Davies, et al., 1971 | gas 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.
Stull D.R., 1969
Stull D.R., Jr.,
The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969. [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]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]
Phillip, 1939
Phillip, N.M.,
Adiabatic and isothermal compressibilities of liquids,
Proc. Indian Acad. Sci., 1939, A9, 109-120. [all data]
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, 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]
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 S°gas Entropy of gas at standard conditions T Temperature 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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