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Acetic acid

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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
B - John E. Bartmess

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.

Reactions 51 to 79

Water + Ethanethioic acid S-tert-butyl ester = Acetic acid + 2-Propanethiol, 2-methyl-

By formula: H2O + C6H12OS = C2H4O2 + C4H10S

Quantity Value Units Method Reference Comment
Deltar-3.00 ± 0.07kcal/molCmWadso, 1957liquid phase; Heat of hydrolysis; ALS

1-[1,2,4]Triazol-1-ylethanone + Water = 1H-1,2,4-Triazole + Acetic acid

By formula: C4H5N3O + H2O = C2H3N3 + C2H4O2

Quantity Value Units Method Reference Comment
Deltar-7.29 ± 0.06kcal/molCmWadso, 1960solid phase; Heat of hydrolysis; ALS

Benzoic acid, o-mercapto-, acetate + Water = Benzoic acid, 2-mercapto- + Acetic acid

By formula: C9H8O3S + H2O = C7H6O2S + C2H4O2

Quantity Value Units Method Reference Comment
Deltar-5.85 ± 0.06kcal/molCmNelander, 1964solid phase; Heat of hydrolysis; ALS

Acetic acid, phenyl ester + Water = Phenol + Acetic acid

By formula: C8H8O2 + H2O = C6H6O + C2H4O2

Quantity Value Units Method Reference Comment
Deltar-6.86 ± 0.04kcal/molCmWadso, 1960, 2liquid phase; Heat of hydrolysis; ALS

Water + Ethanethioic acid, S-phenyl ester = Benzenethiol + Acetic acid

By formula: H2O + C8H8OS = C6H6S + C2H4O2

Quantity Value Units Method Reference Comment
Deltar-2.97 ± 0.08kcal/molCmWadso, 1960, 2liquid phase; Heat of hydrolysis; ALS

1-(2-Acetoxy-2-propyl)indene = 1-(1-methylethylidene)-1H-indene + Acetic acid

By formula: C14H16O2 = 1-(1-methylethylidene)-1H-indene + C2H4O2

Quantity Value Units Method Reference Comment
Deltar-12.1 ± 0.41kcal/molCmThibblin, 1983liquid phase; solvent: Methanol; At 20°C; ALS

Benzoic acid, 4-(acetyloxy)- + Water = Acetic acid + Benzoic acid, 4-hydroxy-

By formula: C9H8O4 + H2O = C2H4O2 + C7H6O3

Quantity Value Units Method Reference Comment
Deltar-4.93 ± 0.08kcal/molCmNelander, 1964solid phase; Heat of hydrolysis; ALS

Ethyl Acetate + Water = Ethanol + Acetic acid

By formula: C4H8O2 + H2O = C2H6O + C2H4O2

Quantity Value Units Method Reference Comment
Deltar0.89 ± 0.04kcal/molCmWadso, 1958liquid phase; Heat of hydrolysis; ALS

Acetic acid, butyl ester + Water = Acetic acid + 1-Butanol

By formula: C6H12O2 + H2O = C2H4O2 + C4H10O

Quantity Value Units Method Reference Comment
Deltar0.80 ± 0.05kcal/molCmWadso, 1958liquid phase; Heat of hydrolysis; ALS

Isopropyl acetate + Water = Acetic acid + Isopropyl Alcohol

By formula: C5H10O2 + H2O = C2H4O2 + C3H8O

Quantity Value Units Method Reference Comment
Deltar0.54 ± 0.05kcal/molCmWadso, 1958liquid phase; Heat of Hydrolysis; ALS

Aspirin + Water = Acetic acid + Salicylic acid

By formula: C9H8O4 + H2O = C2H4O2 + C7H6O3

Quantity Value Units Method Reference Comment
Deltar-6.50 ± 0.07kcal/molCmNelander, 1964solid phase; Heat of hydrolysis; ALS

3-(2-Acetoxy-2-propyl)indene = 1-(1-methylethylidene)-1H-indene + Acetic acid

By formula: C14H16O2 = 1-(1-methylethylidene)-1H-indene + C2H4O2

Quantity Value Units Method Reference Comment
Deltar-10.2 ± 0.31kcal/molCmThibblin, 1983liquid phase; solvent: Methanol; ALS

Water + Acetic acid, methyl ester = Acetic acid + Methyl Alcohol

By formula: H2O + C3H6O2 = C2H4O2 + CH4O

Quantity Value Units Method Reference Comment
Deltar1.05kcal/molCmCoon and Daniels, 1933liquid phase; solvent: in HCl; ALS

Ethanol + Acetic acid = Ethyl Acetate + Water

By formula: C2H6O + C2H4O2 = C4H8O2 + H2O

Quantity Value Units Method Reference Comment
Deltar3.97 ± 0.08kcal/molEqkHalford and Brundage, 1942gas phase; At 313 K; ALS

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

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

Quantity Value Units Method Reference Comment
Deltar0.0kcal/molEqkUtkin, Bogel'fer, et al., 1991liquid phase; NMR; ALS

C6H11NO3 + Water = Acetamide, N-(2-hydroxyethyl)- + Acetic acid

By formula: C6H11NO3 + H2O = C4H9NO2 + C2H4O2

Quantity Value Units Method Reference Comment
Deltar-0.53 ± 0.06kcal/molCmWadso, 1962liquid phase; ALS

C3H4O5- + Water + Acetic acid = C3H6O6-

By formula: C3H4O5- + H2O + C2H4O2 = C3H6O6-

Quantity Value Units Method Reference Comment
Deltar4.60 ± 0.20kcal/molIMREViidanoja, Reiner, et al., 2000gas phase; B

C2H4NO5- + Water + Acetic acid = C2H6NO6-

By formula: C2H4NO5- + H2O + C2H4O2 = C2H6NO6-

Quantity Value Units Method Reference Comment
Deltar4.60 ± 0.20kcal/molIMREViidanoja, Reiner, et al., 2000gas phase; B

Ethanethioic acid, S-[2-(acetylamino)ethyl] ester + Water = Acetamide, N-(β-mercaptoethyl)- + Acetic acid

By formula: C6H11NO2S + H2O = C4H9NOS + C2H4O2

Quantity Value Units Method Reference Comment
Deltar1.75 ± 0.07kcal/molCmWadso, 1962liquid phase; ALS

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

By formula: C6H13NO + H2O = C4H11N + C2H4O2

Quantity Value Units Method Reference Comment
Deltar13.20 ± 0.05kcal/molCmWadso, 1962, 2liquid phase; ALS

2Acetic acid = Acetic anhydride + Water

By formula: 2C2H4O2 = C4H6O3 + H2O

Quantity Value Units Method Reference Comment
Deltar15.22 ± 0.28kcal/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-24.11 ± 0.06kcal/molCmWadso, 1962, 2liquid phase; ALS

2-Pentanone, 5-(acetyloxy)- + Water = 2-Pentanone, 4-hydroxy- + Acetic acid

By formula: C7H12O3 + H2O = C5H10O2 + C2H4O2

Quantity Value Units Method Reference Comment
Deltar2.9kcal/molEqkGrigor'ev, Katsman, et al., 1981liquid phase; ALS

Acetyl nitrate + Acetic acid = Acetic anhydride + Nitric acid

By formula: C2H3NO4 + C2H4O2 = C4H6O3 + HNO3

Quantity Value Units Method Reference Comment
Deltar3.99kcal/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-10.5kcal/molKinShatynski and Hanesian, 1993solid phase; ALS

NO3 anion + Acetic acid = C2H4NO5-

By formula: NO3- + C2H4O2 = C2H4NO5-

Quantity Value Units Method Reference Comment
Deltar11.80 ± 0.20kcal/molIMREViidanoja, Reiner, et al., 1998gas phase; B

Nitrogen oxide anion + Acetic acid = C2H4NO4-

By formula: NO2- + C2H4O2 = C2H4NO4-

Quantity Value Units Method Reference Comment
Deltar12.20 ± 0.20kcal/molIMREViidanoja, Reiner, et al., 1998gas phase; B

Ketene + Acetic acid = Acetic anhydride

By formula: C2H2O + C2H4O2 = C4H6O3

Quantity Value Units Method Reference Comment
Deltar-20.9 ± 0.53kcal/molEqkBlake, Davies, et al., 1971gas phase; ALS

CO3- + Acetic acid = C3H4O5-

By formula: CO3- + C2H4O2 = C3H4O5-

Quantity Value Units Method Reference Comment
Deltar11.30 ± 0.20kcal/molIMREViidanoja, Reiner, et al., 1998gas phase; B

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.

Wadso, 1957
Wadso, I., The heats of hydrolysis of some alkyl thiolesters, Acta Chem. Scand., 1957, 11, 1745-1751. [all data]

Wadso, 1960
Wadso, I., Heats of hydrolysis of N-acetylated imidazole, 1,2,4-triazole and tetrazole, Acta Chem. Scand., 1960, 14, 903-908. [all data]

Nelander, 1964
Nelander, L., The heats of hydrolysis of aspirin, thioaspirin, and their p-analogues, Acta Chem. Scand., 1964, 18, 973-984. [all data]

Wadso, 1960, 2
Wadso, I., Heats of hydrolysis of phenyl acetate and phenyl thiolacetate, Acta Chem. Scand., 1960, 14, 561-565. [all data]

Thibblin, 1983
Thibblin, A., Microcalorimetry in kinetic studies of a complex reaction system, Chem. Scr., 1983, 22, 70-73. [all data]

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

Coon and Daniels, 1933
Coon, E.D.; Daniels, F., An isothermal calorimeter for slow reactions, J. Phys. Chem., 1933, 37, 1-12. [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]

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]

Wadso, 1962
Wadso, I., Heats of hydrolysis of acetates and thiolacetates in aqueous solution, Acta Chem. Scand., 1962, 16, 487-494. [all data]

Viidanoja, Reiner, et al., 2000
Viidanoja, J.; Reiner, T.; Kiendler, A.; Grimm, F.; Arnold, F., Laboratory investigations of negative ion molecule reactions of propionic, butyric, glyoxylic, pyruvic, and pinonic acids, Int. J. Mass Spectrom., 2000, 194, 1, 53-68, https://doi.org/10.1016/S1387-3806(99)00172-4 . [all data]

Wadso, 1962, 2
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]

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]

Grigor'ev, Katsman, et al., 1981
Grigor'ev, A.A.; Katsman, E.A.; Bobrov, A.F.; Dan'ko, T.N.; Pinkhasik, E.V., Preparation of «gamma»-acetopropyl alcohol, Sov. Chem. Ind. (Engl. Transl.), 1981, 967-972. [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]

Viidanoja, Reiner, et al., 1998
Viidanoja, J.; Reiner, T.; Arnold, F., Laboratory Investigations of Negative Ion-Molecule Reactions of Formic and Acetic Acid., Int. J. Mass Spectrom., 1998, 181, 1-3, 31, https://doi.org/10.1016/S1387-3806(98)14151-9 . [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, Reaction thermochemistry data, References