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Acetic anhydride

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Gas phase 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 by: Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
gas389.95J/mol*KN/AStull D.R., 1969 

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
99.50298.15Stull D.R., 1969Selected values were based on an approximation of heat capacities from Cp(T) values of acetic acid.
100.04300.
129.12400.
153.89500.
174.14600.
191.38700.
204.64800.
216.06900.
226.401000.

Condensed phase 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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Deltafliquid-625.0 ± 3.4kJ/molCmGuthrie, 1974Reanalyzed 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
168.2303.2Phillip, 1939DH

Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny, director
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil412. ± 2.KAVGN/AAverage of 10 out of 11 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus200. ± 1.KAVGN/AAverage of 9 values; Individual data points
Quantity Value Units Method Reference Comment
Tc606.KN/AAmbrose and Ghiassee, 1987Uncertainty assigned by TRC = 4. K; decomposition of sample prevented accurate measurement, reported value based partly on a correlation; TRC
Tc569.KN/AVespigniani, 1903Uncertainty assigned by TRC = 20. K; TRC
Quantity Value Units Method Reference Comment
Pc40.00barN/AAmbrose and Ghiassee, 1987Uncertainty assigned by TRC = 2.00 bar; based partly on a corelation because of decompostion of smp.; TRC
Pc46.80barN/AVespigniani, 1903Uncertainty assigned by TRC = 4.053 bar; TRC

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
317.20.020Weast and Grasselli, 1989BS
317.0.020Buckingham and Donaghy, 1982BS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
43.3364.EBAmbrose and Ghiassee, 1987, 2Based on data from 349. - 429. K.; AC
47.6428.AStephenson and Malanowski, 1987Based on data from 413. - 526. K.; AC
45.5335.AStephenson and Malanowski, 1987Based on data from 320. - 413. K. See also Dykyj, 1971.; AC
44.2351.N/AMcDonald, Shrader, et al., 1959Based on data from 336. - 412. K.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Temperature (K) A B C Reference
335.99 - 412.574.246551427.77-75.113McDonald, Shrader, et al., 1959

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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

Gas phase ion energetics 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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C4H6O3+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
~10.0PEBock, Hirabayashi, et al., 1981LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H3O+10.14CH3COOPITraeger, McLouglin, et al., 1982LBLHLM
C2H3O+10.19 ± 0.02?PIShigorin, Filyugina, et al., 1967RDSH
C2H4O2+9.65 ± 0.02CH2=CO?PIShigorin, Filyugina, et al., 1967RDSH
C3H3O3+10.14 ± 0.02CH3PIShigorin, Filyugina, et al., 1967RDSH

Ion clustering 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 by: Robert C. Dunbar

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

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

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

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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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center, 1998.
NIST MS number 291302

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Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), NIST Free Links, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Normal alkane RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryOV-101706.Zenkevich, 200525. m/0.20 mm/0.10 «mu»m, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryPolydimethyl siloxanes706.Zenkevich, 2001Program: not specified
CapillaryMethyl Silicone699.Zenkevich, Korolenko, et al., 1995Program: not specified

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-Wax1236.Umano, Hagi, et al., 1995He, 40. C @ 2. min, 2. K/min; Column length: 60. m; Column diameter: 0.25 mm; Tend: 200. C
CapillaryCarbowax 20M1240.Kawakami, Kobayashi, et al., 1993He, 60. C @ 4. min, 2. K/min; Column length: 50. m; Column diameter: 0.25 mm; Tend: 180. C

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryPolyethylene Glycol1227.Zenkevich, Korolenko, et al., 1995Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, 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]

Ambrose and Ghiassee, 1987
Ambrose, D.; Ghiassee, N.B., Vapor Pressure, Critical Temperature and Critical Pressure of Acetic Anhydride, J. Chem. Thermodyn., 1987, 19, 911. [all data]

Vespigniani, 1903
Vespigniani, G.R., Gazz. Chim. Ital., 1903, 33, 73-8. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]

Ambrose and Ghiassee, 1987, 2
Ambrose, D.; Ghiassee, N.B., Vapour pressure, critical temperature, and critical pressure of acetic anhydride, The Journal of Chemical Thermodynamics, 1987, 19, 9, 911-913, https://doi.org/10.1016/0021-9614(87)90037-1 . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Dykyj, 1971
Dykyj, J., Petrochemia, 1971, 11, 2, 27. [all data]

McDonald, Shrader, et al., 1959
McDonald, R.A.; Shrader, S.A.; Stull, D.R., Vapor Pressures and Freezing Points of Thirty Pure Organic Compounds., J. Chem. Eng. Data, 1959, 4, 4, 311-313, https://doi.org/10.1021/je60004a009 . [all data]

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]

Bock, Hirabayashi, et al., 1981
Bock, H.; Hirabayashi, T.; Mohmand, S., Thermische erzeugung von alkyl- und halogenketenen, Chem. Ber., 1981, 114, 2595. [all data]

Traeger, McLouglin, et al., 1982
Traeger, J.C.; McLouglin, R.G.; Nicholson, A.J.C., Heat of formation for acetyl cation in the gas phase, J. Am. Chem. Soc., 1982, 104, 5318. [all data]

Shigorin, Filyugina, et al., 1967
Shigorin, D.N.; Filyugina, A.D.; Potapov, V.K., Role of intramolecular hydrogen bonding in the ionisation and dissociation of compounds, Zh. Fiz. Khim., 1967, 41, 2336, In original 1255. [all data]

Zenkevich, 2005
Zenkevich, I.G., Experimentally measured retention indices., 2005. [all data]

Zenkevich, 2001
Zenkevich, I.G., Encyclopedia of Chromatography. Derivatization of Amines, Amino Acids, Amides and Imides for GC Analysis, Marcel Dekker, Inc, New York - Basel, 2001, 224. [all data]

Zenkevich, Korolenko, et al., 1995
Zenkevich, I.G.; Korolenko, L.I.; Khralenkova, N.B., Desorption with solvent vapor as a method of sample preparation in the sorption preconcentration of organic-compounds from the air of a working area and from industrial-waste gases, J. Appl. Chem. USSR (Engl. Transl.), 1995, 50, 10, 937-944. [all data]

Umano, Hagi, et al., 1995
Umano, K.; Hagi, Y.; Nakahara, K.; Shyoji, A.; Shibamoto, T., Volatile chemicals formed in the headspace of a heated D-glucose/L-cysteine Maillard model system, J. Agric. Food Chem., 1995, 43, 8, 2212-2218, https://doi.org/10.1021/jf00056a046 . [all data]

Kawakami, Kobayashi, et al., 1993
Kawakami, M.; Kobayashi, A.; Kator, K., Volatile constituents of Rooibos tea (Aspalathus linearis) as affected by extraction process, J. Agric. Food Chem., 1993, 41, 4, 633-636, https://doi.org/10.1021/jf00028a023 . [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, References