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Acetone

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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
MS - José A. Martinho Simões
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
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.

Reactions 51 to 85

Acetone + Chlorothiolacetic acid = Ethanethioic acid, chloro-, S-(1-hydroxy-1-methylethyl) ester

By formula: C3H6O + C2H3ClOS = C5H9ClO2S

Quantity Value Units Method Reference Comment
Deltar-28. ± 0.4kJ/molEqkHorii, Kawamura, et al., 1972liquid phase; solvent: CD3COCD3; NMR; ALS

Propane, 2,2-diethoxy- + Water = 2Ethanol + Acetone

By formula: C7H16O2 + H2O = 2C2H6O + C3H6O

Quantity Value Units Method Reference Comment
Deltar21.2 ± 0.2kJ/molCmStern and Dorer, 1962liquid phase; Heat of hydrolysis; ALS

Acetic acid + Acetone = 1-Propen-2-ol, acetate + Water

By formula: C2H4O2 + C3H6O = C5H8O2 + H2O

Quantity Value Units Method Reference Comment
Deltar60.2 ± 0.3kJ/molCmSunner, 1957liquid phase; Heat of hydrolysis; ALS

C12H16CrO5 (solution) + Acetone (solution) = Heptane (solution) + C8H6CrO6 (solution)

By formula: C12H16CrO5 (solution) + C3H6O (solution) = C7H16 (solution) + C8H6CrO6 (solution)

Quantity Value Units Method Reference Comment
Deltar-56.5 ± 5.0kJ/molPACYang, Peters, et al., 1986solvent: Heptane; MS

C14H21MnO2 (solution) + Acetone (solution) = C10H11MnO3 (solution) + Heptane (solution)

By formula: C14H21MnO2 (solution) + C3H6O (solution) = C10H11MnO3 (solution) + C7H16 (solution)

Quantity Value Units Method Reference Comment
Deltar-72.8 ± 4.2kJ/molPACKlassen, Selke, et al., 1990solvent: Heptane; MS

Tungsten hexacarbonyl (solution) + Acetone (solution) = C8H6O6W (solution) + Carbon monoxide (solution)

By formula: C6O6W (solution) + C3H6O (solution) = C8H6O6W (solution) + CO (solution)

Quantity Value Units Method Reference Comment
Deltar74.9 ± 5.9kJ/molPCNakashima and Adamson, 1982solvent: Acetone; MS

(Potassium ion (1+) bullet 3Acetone) + Acetone = (Potassium ion (1+) bullet 4Acetone)

By formula: (K+ bullet 3C3H6O) + C3H6O = (K+ bullet 4C3H6O)

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
25.293.ES/HPMSBlades, Klassen, et al., 1995gas phase; M

1-Propene, 2-methoxy- + Water = Methyl Alcohol + Acetone

By formula: C4H8O + H2O = CH4O + C3H6O

Quantity Value Units Method Reference Comment
Deltar-24.04 ± 0.46kJ/molEqkHine and Arata, 1976liquid phase; ALS

Methyl Alcohol + Acetone = 1-Propene, 2-methoxy- + Water

By formula: CH4O + C3H6O = C4H8O + H2O

Quantity Value Units Method Reference Comment
Deltar24.04 ± 0.46kJ/molEqkHine and Arata, 1976liquid phase; ALS

Iodide + Acetone = (Iodide bullet Acetone)

By formula: I- + C3H6O = (I- bullet C3H6O)

Quantity Value Units Method Reference Comment
Deltar50.2 ± 4.2kJ/molTDAsCaldwell, Masucci, et al., 1989gas phase; B,M

Cyclohexanol + Acetone = Cyclohexanone + Isopropyl Alcohol

By formula: C6H12O + C3H6O = C6H10O + C3H8O

Quantity Value Units Method Reference Comment
Deltar9.9 ± 1.9kJ/molEqkFedoseenko, Yursha, et al., 1983gas phase; At 503 K; ALS

Acetone + Iodine = Hydrogen iodide + 1-iodoacetone

By formula: C3H6O + I2 = HI + C3H5IO

Quantity Value Units Method Reference Comment
Deltar50.6 ± 5.0kJ/molEqkSolly, Golden, et al., 1970gas phase; ALS

C20H17Cl2OPPt (cr) = C17H25ClP2Pt (cr) + Acetone (g)

By formula: C20H17Cl2OPPt (cr) = C17H25ClP2Pt (cr) + C3H6O (g)

Quantity Value Units Method Reference Comment
Deltar-33.6 ± 3.2kJ/molDSCBrown, Puddephatt, et al., 1974Temperature: 394 K; MS

C3H6O+ + Acetone = (C3H6O+ bullet Acetone)

By formula: C3H6O+ + C3H6O = (C3H6O+ bullet C3H6O)

Quantity Value Units Method Reference Comment
Deltar51.9kJ/molPITrott, Blais, et al., 1978gas phase; «DELTA»rH>; M

2Methyl Alcohol + Acetone = Water + Propane, 2,2-dimethoxy-

By formula: 2CH4O + C3H6O = H2O + C5H12O2

Quantity Value Units Method Reference Comment
Deltar-46. ± 1.kJ/molCmWiberg, Morgan, et al., 1994gas phase; ALS

cis-1,2-Cyclodecanediol + Acetone = C13H24O2 + Water

By formula: C10H20O2 + C3H6O = C13H24O2 + H2O

Quantity Value Units Method Reference Comment
Deltar-4.6kJ/molEqkAnteunis and Rommelaere, 1970liquid phase; ALS

meso-2,3-Butanediol + Acetone = 1,3-Dioxolane, 2,2,4,5-tetramethyl-, cis- + Water

By formula: C4H10O2 + C3H6O = C7H14O2 + H2O

Quantity Value Units Method Reference Comment
Deltar-17.kJ/molEqkAnteunis and Rommelaere, 1970liquid phase; ALS

1,2-Propanediol, 2-methyl- + Acetone = 1,3-Dioxolane, 2,2,4,4-tetramethyl- + Water

By formula: C4H10O2 + C3H6O = C7H14O2 + H2O

Quantity Value Units Method Reference Comment
Deltar-3.kJ/molEqkAnteunis and Rommelaere, 1970liquid phase; ALS

1,2-Ethanediol + Acetone = 1,3-Dioxolane, 2,2-dimethyl- + Water

By formula: C2H6O2 + C3H6O = C5H10O2 + H2O

Quantity Value Units Method Reference Comment
Deltar-10.kJ/molEqkAnteunis and Rommelaere, 1970liquid phase; ALS

Neopentyl glycol + Acetone = 1,3 Dioxane, 2,2,5,5-tetramethyl- + Water

By formula: C5H12O2 + C3H6O = C8H16O2 + H2O

Quantity Value Units Method Reference Comment
Deltar-11.kJ/molEqkAnteunis and Rommelaere, 1970liquid phase; ALS

Propylene Glycol + Acetone = 1,3-Dioxolane, 2,2,4-trimethyl- + Water

By formula: C3H8O2 + C3H6O = C6H12O2 + H2O

Quantity Value Units Method Reference Comment
Deltar-3.kJ/molEqkAnteunis and Rommelaere, 1970liquid phase; ALS

Acetone + 1,2-Propanediol, 3-chloro- = 1,3-Dioxolane, 4-(chloromethyl)-2,2-dimethyl- + Water

By formula: C3H6O + C3H7ClO2 = C6H11ClO2 + H2O

Quantity Value Units Method Reference Comment
Deltar-12.kJ/molEqkAnteunis and Rommelaere, 1970liquid phase; ALS

1,3-Propanediol + Acetone = 1,3-Dioxane, 2,2-dimethyl- + Water

By formula: C3H8O2 + C3H6O = C6H12O2 + H2O

Quantity Value Units Method Reference Comment
Deltar-23.kJ/molEqkAnteunis and Rommelaere, 1970liquid phase; ALS

Cyclohexanone + Isopropyl Alcohol = Cyclohexanol + Acetone

By formula: C6H10O + C3H8O = C6H12O + C3H6O

Quantity Value Units Method Reference Comment
Deltar-9.9 ± 1.9kJ/molEqkKabo, Yursha, et al., 1988gas phase; ALS

C3H5O+ + Acetone = (C3H5O+ bullet Acetone)

By formula: C3H5O+ + C3H6O = (C3H5O+ bullet C3H6O)

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
35.295.FAMackay, Rakshit, et al., 1982gas phase; M

(Copper ion (1+) bullet 2Acetone) + Acetone = (Copper ion (1+) bullet 3Acetone)

By formula: (Cu+ bullet 2C3H6O) + C3H6O = (Cu+ bullet 3C3H6O)

Quantity Value Units Method Reference Comment
Deltar64. ± 2.kJ/molCIDTChu, 2002RCD

(Copper ion (1+) bullet 3Acetone) + Acetone = (Copper ion (1+) bullet 4Acetone)

By formula: (Cu+ bullet 3C3H6O) + C3H6O = (Cu+ bullet 4C3H6O)

Quantity Value Units Method Reference Comment
Deltar61.1 ± 5.0kJ/molCIDTChu, 2002RCD

2-Propanone, phenylhydrazone + Water = Hydrazine, phenyl- + Acetone

By formula: C9H12N2 + H2O = C6H8N2 + C3H6O

Quantity Value Units Method Reference Comment
Deltar-43.1kJ/molCmLandrieu, 1905solid phase; ALS

C2H3O+ + Acetone = (C2H3O+ bullet Acetone)

By formula: C2H3O+ + C3H6O = (C2H3O+ bullet C3H6O)

Quantity Value Units Method Reference Comment
Deltar52.3kJ/molPITrott, Blais, et al., 1978gas phase; M

Propylene oxide = Acetone

By formula: C3H6O = C3H6O

Quantity Value Units Method Reference Comment
Deltar-124.kJ/molEqkPolkovnikova and Lapiclus, 1974gas phase; At 300 K; ALS

Chromium ion (1+) + Acetone = (Chromium ion (1+) bullet Acetone)

By formula: Cr+ + C3H6O = (Cr+ bullet C3H6O)

Quantity Value Units Method Reference Comment
Deltar175. ± 14.kJ/molRAKLin, Chen, et al., 1997RCD

Manganese ion (1+) + Acetone = (Manganese ion (1+) bullet Acetone)

By formula: Mn+ + C3H6O = (Mn+ bullet C3H6O)

Quantity Value Units Method Reference Comment
Deltar159. ± 14.kJ/molRAKLin, Chen, et al., 1997RCD

Silver ion (1+) + Acetone = (Silver ion (1+) bullet Acetone)

By formula: Ag+ + C3H6O = (Ag+ bullet C3H6O)

Quantity Value Units Method Reference Comment
Deltar160. ± 19.kJ/molRAKHo, Yang, et al., 1997RCD

2Acetone = 2-Pentanone, 4-hydroxy-4-methyl-

By formula: 2C3H6O = C6H12O2

Quantity Value Units Method Reference Comment
Deltar-34.27kJ/molEqkDavis and Burrows, 1936liquid phase; ALS

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.

Horii, Kawamura, et al., 1972
Horii, T.; Kawamura, S.; Tsurugi, J., A NMR study of the thioacetic acid-acetone mixture, Bull. Chem. Soc. Jpn., 1972, 45, 2200-2202. [all data]

Stern and Dorer, 1962
Stern, J.H.; Dorer, F.H., Standard heats of formation of 2,2-Dimethoxypropane (1), and 2,2 -Diethoxypropane (1). Group additivity theory and calculated heats of formation and five ketals, J. Phys. Chem., 1962, 66, 97-99. [all data]

Sunner, 1957
Sunner, S., The heat of hydrolysis of i-propenyl acetate and m-cresyl acetate and the heat of formation of acetone, Acta Chem. Scand., 1957, 11, 1757-1760. [all data]

Yang, Peters, et al., 1986
Yang, G.K.; Peters, K.S.; Vaida, V., Chem. Phys. Lett., 1986, 125, 566. [all data]

Klassen, Selke, et al., 1990
Klassen, J.K.; Selke, M.; Sorensen, A.A.; Yang, G.K., J. Am. Chem. Soc., 1990, 112, 1267. [all data]

Nakashima and Adamson, 1982
Nakashima, M.; Adamson, A.W., J. Phys. Chem., 1982, 86, 2905. [all data]

Blades, Klassen, et al., 1995
Blades, A.T.; Klassen, J.S.; Kebarle, P., Free Energies of Hydration in the Gas Phase on the Anions of Some Oxo Acids of C, N, S, P, Cl and I, J. Am. Chem. Soc., 1995, 117, 42, 10563, https://doi.org/10.1021/ja00147a019 . [all data]

Hine and Arata, 1976
Hine, J.; Arata, K., Keto-Enol tautomerism. II. The calorimetrical determination of the equilibrium constants for keto-enol tautomerism for cyclohexanone, Bull. Chem. Soc. Jpn., 1976, 49, 3089-3092. [all data]

Caldwell, Masucci, et al., 1989
Caldwell, G.W.; Masucci, J.A.; Ikonomou, M.G., Negative Ion Chemical Ionization Mass Spectrometry - Binding of Molecules to Bromide and Iodide Anions, Org. Mass Spectrom., 1989, 24, 1, 8, https://doi.org/10.1002/oms.1210240103 . [all data]

Fedoseenko, Yursha, et al., 1983
Fedoseenko, V.I.; Yursha, I.A.; Kabo, G.Ya., Equilibrium and thermodynamics of cyclohexanol dehydrogenation reactions, Dokl. Akad. Nauk BSSR, 1983, 27, 926-929. [all data]

Solly, Golden, et al., 1970
Solly, R.K.; Golden, D.M.; Benson, S.W., Thermochemical properties of iodoacetone. Intramolecular electrostatic interactions in polar molecules, J. Am. Chem. Soc., 1970, 92, 4653-4656. [all data]

Brown, Puddephatt, et al., 1974
Brown, M.P.; Puddephatt, R.J.; Upton, C.E.E.; Lavington, S.W., J. Chem. Soc., Dalton Trans., 1974, 1613.. [all data]

Trott, Blais, et al., 1978
Trott, W.M.; Blais, N.C.; Walters, E.A., Molecular beam photoionization study of acetone and acetone-d6, J. Chem. Phys., 1978, 69, 3150. [all data]

Wiberg, Morgan, et al., 1994
Wiberg, K.B.; Morgan, K.M.; Maltz, H., Thermochemistry of carbonyl reactions. 6. A study of hydration equilibria, J. Am. Chem. Soc., 1994, 116, 11067-11077. [all data]

Anteunis and Rommelaere, 1970
Anteunis, M.; Rommelaere, Y., NMR experiments on acetals. XXIX. The ease of acetonide formation of some glycols, Bull. Soc. Chim. Belg., 1970, 79, 523-530. [all data]

Kabo, Yursha, et al., 1988
Kabo, G.J.; Yursha, I.A.; Frenkel, M.L.; Poleshchuk, P.A.; Fedoseenko, V.I.; Ladutko, A.I., Thermodynamic properties of cyclohexanol and cyclohexanone, J. Chem. Thermodyn., 1988, 20, 429-437. [all data]

Mackay, Rakshit, et al., 1982
Mackay, G.I.; Rakshit, A.B.; Bohme, D.K., An Experimental Study of the Reactivity and Relative Basicity of the Methoxide Anion in the Gas Phase at Room Temperature, and their Perturbation by Methanol Solvent, Can. J. Chem., 1982, 60, 20, 2594, https://doi.org/10.1139/v82-373 . [all data]

Chu, 2002
Chu, Y., Solvation of Copper Ions by Acetone. Structures and Sequential Binding Energies of Cu+(acetone)x, x=1-4 From Collision-Induced Dissociation and Theoretical Studies, J. Am. Soc. Mass Spectrom., 2002, 13, 5, 453, https://doi.org/10.1016/S1044-0305(02)00355-0 . [all data]

Landrieu, 1905
Landrieu, M.Ph., Thermochimie. - Thermochimie des hydrazones, Compt. Rend., 1905, 141, 358-361. [all data]

Polkovnikova and Lapiclus, 1974
Polkovnikova, A.G.; Lapiclus, V.L., Calculation of the equilibrium and heat of isomerization of propylene oxide on a lithium phosphate catalyst, Neftekhimiya, 1974, 14, 113-115. [all data]

Lin, Chen, et al., 1997
Lin, C.-Y.; Chen, Q.; Chen, H.; Freiser, B.S., Bond Dissociation Energy Determinations for MOC(CH3)2+ and MOC(CD3)2+ (M=Cr, Mn) Using Continuous Ejection and Radiative Association Methods, Int. J. Mass Spectrom. Ion Proc., 1997, 167/168, 713, https://doi.org/10.1016/S0168-1176(97)00131-6 . [all data]

Ho, Yang, et al., 1997
Ho, Y.-P.; Yang, Y.-C.; Klippenstein, S.J.; Dunbar, R.C., Binding Energies of Ag+ and Cd+ Complexes from Analysis of Radiative Association Kinetics, J. Phys. Chem. A, 1997, 101, 18, 3338, https://doi.org/10.1021/jp9637284 . [all data]

Davis and Burrows, 1936
Davis, G.L.; Burrows, G.H., Equilibrium and free energy relationships in the system acetone-diacetone alcohol, J. Am. Chem. Soc., 1936, 58, 311-312. [all data]


Notes

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