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Ethanol

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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
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 77

N-Formylimidazole diethyl acetal + Water = Ethyl formate + 1H-Imidazole + Ethanol

By formula: C8H14N2O2 + H2O = C3H6O2 + C3H4N2 + C2H6O

Quantity Value Units Method Reference Comment
Deltar-8.28 ± 0.42kcal/molCmGuthrie and Pike, 1987liquid phase; Heat of hydrolysis; ALS

4Ethanol (l) + Titanium tetrachloride (l) = titanium(4+) ethanolate (l) + 4Hydrogen chloride (g)

By formula: 4C2H6O (l) + Cl4Ti (l) = C8H20O4Ti (l) + 4HCl (g)

Quantity Value Units Method Reference Comment
Deltar19.5 ± 0.1kcal/molRSCBradley and Hillyer, 1966Please also see Pedley and Rylance, 1977.; MS

Ethyl orthoformate + Water = Ethyl formate + 2Ethanol

By formula: C7H16O3 + H2O = C3H6O2 + 2C2H6O

Quantity Value Units Method Reference Comment
Deltar-3.17 ± 0.19kcal/molCmHine and Klueppet, 1974liquid phase; Heat of hydrolysis; ALS

2-Methyl-1-butene + Ethanol = Butane, 2-ethoxy-2-methyl-

By formula: C5H10 + C2H6O = C7H16O

Quantity Value Units Method Reference Comment
Deltar-8.4 ± 1.4kcal/molEqkRihko, Linnekoski, et al., 1994liquid phase; solvent: Alcohol/alkane mixture; ALS

2-Butene, 2-methyl- + Ethanol = Butane, 2-ethoxy-2-methyl-

By formula: C5H10 + C2H6O = C7H16O

Quantity Value Units Method Reference Comment
Deltar-6.5 ± 1.6kcal/molEqkRihko, Linnekoski, et al., 1994liquid phase; solvent: Alcohol/alkane mixture; ALS

Ethanol (solution) + C5H11BrMg (solution) = C2H5BrMgO (solution) + Pentane (solution)

By formula: C2H6O (solution) + C5H11BrMg (solution) = C2H5BrMgO (solution) + C5H12 (solution)

Quantity Value Units Method Reference Comment
Deltar-47.7 ± 1.0kcal/molRSCHolm, 1983solvent: Diethyl ether; MS

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

By formula: C7H16O2 + H2O = 2C2H6O + C3H6O

Quantity Value Units Method Reference Comment
Deltar5.06 ± 0.05kcal/molCmStern and Dorer, 1962liquid phase; Heat of hydrolysis; ALS

C12H16CrO5 (solution) + Ethanol (solution) = C7H5CrO6 (solution) + Heptane (solution)

By formula: C12H16CrO5 (solution) + C2H6O (solution) = C7H5CrO6 (solution) + C7H16 (solution)

Quantity Value Units Method Reference Comment
Deltar-13.8 ± 1.2kcal/molPACYang, Peters, et al., 1986solvent: Heptane; MS

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

C2H5LiO (cr) + (Hydrogen chloride bullet 552Water) (solution) = Ethanol (l) + lithium chloride (cr)

By formula: C2H5LiO (cr) + (HCl bullet 552H2O) (solution) = C2H6O (l) + ClLi (cr)

Quantity Value Units Method Reference Comment
Deltar-10.1 ± 0.93kcal/molRSCLeal and Martinho Simões, 1993MS

Ethanol + Chloral = 2,2,2-Trichloro-1-ethoxy ethanol

By formula: C2H6O + C2HCl3O = C4H7Cl3O2

Quantity Value Units Method Reference Comment
Deltar-11.3kcal/molEqkJensen and Pedersen, 1971liquid phase; solvent: Heptane; 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

C5H14OSn (l) + Water (l) = C3H10OSn (cr) + (Ethanol bullet 55Water) (solution)

By formula: C5H14OSn (l) + H2O (l) = C3H10OSn (cr) + (C2H6O bullet 55H2O) (solution)

Quantity Value Units Method Reference Comment
Deltar-18.3 ± 0.41kcal/molRSCBaldwin, Lappert, et al., 1972MS

Ethanol + Benzene, 1,1'-(diazomethylene)bis- = C13H28O4 + Nitrogen

By formula: C2H6O + C13H10N2 = C13H28O4 + N2

Quantity Value Units Method Reference Comment
Deltar-53.6 ± 1.0kcal/molCphaHartstock, Kanabus-Kaminska, et al., 1989liquid phase; ALS

Ethanol + 2-Oxetanone, 4-methylene- = Ethyl acetoacetate

By formula: C2H6O + C4H4O2 = C6H10O3

Quantity Value Units Method Reference Comment
Deltar-30.35kcal/molKinLopatin, Popov, et al., 1992liquid phase; solvent: Solution; ALS

Ethanol + Ethene, 1,1-dichloro-2,2-difluoro- = C4H6Cl2F2O

By formula: C2H6O + C2Cl2F2 = C4H6Cl2F2O

Quantity Value Units Method Reference Comment
Deltar-39.3 ± 0.6kcal/molCmKennedy, Lacher, et al., 1969gas phase; ALS

Hydrogen + Ethyl Acetate = 2Ethanol

By formula: H2 + C4H8O2 = 2C2H6O

Quantity Value Units Method Reference Comment
Deltar-17.92 ± 0.13kcal/molCmWiberg, Crocker, et al., 1991liquid phase; ALS

C10H11ClZr (cr) + Ethanol (l) = C12H15ClOZr (cr) + Hydrogen (g)

By formula: C10H11ClZr (cr) + C2H6O (l) = C12H15ClOZr (cr) + H2 (g)

Quantity Value Units Method Reference Comment
Deltar-18.2 ± 0.31kcal/molRSCDiogo, Simoni, et al., 1993MS

C2H5LiO (cr) + Water (l) = HLiO (cr) + Ethanol (l)

By formula: C2H5LiO (cr) + H2O (l) = HLiO (cr) + C2H6O (l)

Quantity Value Units Method Reference Comment
Deltar-0.86 ± 0.60kcal/molRSCLeal and Martinho Simões, 1993MS

Propane, 2-ethoxy-2-methyl- = 1-Propene, 2-methyl- + Ethanol

By formula: C6H14O = C4H8 + C2H6O

Quantity Value Units Method Reference Comment
Deltar8.47 ± 0.46kcal/molEqkSharonov, Rozhnov, et al., 1995liquid phase; ALS

Butane, 2-ethoxy-2-methyl- = 2-Butene, 2-methyl- + Ethanol

By formula: C7H16O = C5H10 + C2H6O

Quantity Value Units Method Reference Comment
Deltar8.16 ± 0.19kcal/molEqkSharonov, Rozhnov, et al., 1995liquid phase; ALS

C2H5NaO (cr) + Water (l) = Sodium hydroxide (cr) + Ethanol (l)

By formula: C2H5NaO (cr) + H2O (l) = HNaO (cr) + C2H6O (l)

Quantity Value Units Method Reference Comment
Deltar-1.4 ± 0.45kcal/molRSCLeal, Pires de Matos, et al., 1991MS

Ethanol + Nitric acid = Nitric acid, ethyl ester + Water

By formula: C2H6O + HNO3 = C2H5NO3 + H2O

Quantity Value Units Method Reference Comment
Deltar-6.00kcal/molEqkRubtsov, 1986liquid phase; ALS

Ketene + Ethanol = Ethyl Acetate

By formula: C2H2O + C2H6O = C4H8O2

Quantity Value Units Method Reference Comment
Deltar-36.44kcal/molCmRice and Greenberg, 1934gas phase; ALS

Lithium ion (1+) + Ethanol = (Lithium ion (1+) bullet Ethanol)

By formula: Li+ + C2H6O = (Li+ bullet C2H6O)

Quantity Value Units Method Reference Comment
Deltar39.2 ± 1.9kcal/molCIDTRodgers and Armentrout, 2000RCD

2Ethanol = Ethyl ether + Water

By formula: 2C2H6O = C4H10O + H2O

Quantity Value Units Method Reference Comment
Deltar-5.74 ± 0.02kcal/molEqkConnett, 1972gas 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.

Guthrie and Pike, 1987
Guthrie, J.P.; Pike, D.C., Hydration of acylimidazoles: tetrahedral intermediates in acylimidazole hydrolysis and nucleophilic attack by imidazole on esters. The question of concerted mechanisms for acyl transfers, Can. J. Chem., 1987, 65, 1951-1969. [all data]

Bradley and Hillyer, 1966
Bradley, D.C.; Hillyer, M.J., Trans. Faraday Soc., 1966, 62, 2367. [all data]

Pedley and Rylance, 1977
Pedley, J.B.; Rylance, J., Computer Analysed Thermochemical Data: Organic and Organometallic Compounds, University of Sussex, Brigton, 1977. [all data]

Hine and Klueppet, 1974
Hine, J.; Klueppet, A.W., Structural effects on rates and equilibria. XVIII. Thermodynamic stability of ortho esters, J. Am. Chem. Soc., 1974, 96, 2924-2929. [all data]

Rihko, Linnekoski, et al., 1994
Rihko, L.K.; Linnekoski, J.A.; Krause, A.O., Reaction equilibria in the synthesis of 2-methoxy-2-methylbutane and 2-ethyoxy-2-methylbutane in the liquid phase, J. Chem. Eng. Data, 1994, 39, 700-704. [all data]

Holm, 1983
Holm, T., Acta Chem. Scand. B, 1983, 37, 797. [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]

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

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

Leal and Martinho Simões, 1993
Leal, J.P.; Martinho Simões, J.A., J. Organometal. Chem., 1993, 460, 131. [all data]

Jensen and Pedersen, 1971
Jensen, R.B.; Pedersen, S.B., Reaction between chloral and alcohols. 9. Dissociation of chloral hemiacetals of some aliphatic primary and secondary alcohols, Acta Chem. Scand., 1971, 25, 2911-2930. [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]

Baldwin, Lappert, et al., 1972
Baldwin, J.C.; Lappert, M.F.; Pedley, J.B.; Poland, J.S., J. Chem. Soc., Dalton Trans., 1972, 1943.. [all data]

Hartstock, Kanabus-Kaminska, et al., 1989
Hartstock, F.W.; Kanabus-Kaminska, J.M.; Griller, D., Heat of formation of benzophenone oxide [1], Int. J. Chem. Kinet., 1989, 21, 157-163. [all data]

Lopatin, Popov, et al., 1992
Lopatin, E.B.; Popov, V.V.; Epshtein, N.A.; Mikhaleva, L.M.; Makarov, Yu.N., Kinetic and thermochemical characteristics of diketene-based reactions, Khim.-Farm. Zh., 1992, 26, 76-78. [all data]

Kennedy, Lacher, et al., 1969
Kennedy, M.B.; Lacher, J.R.; Park, J.D., Reaction heats of organic compounds. VI. Heats of addition of some alcohols to 1,1-dichloro-2,2-difluoroethylene, Trans. Faraday Soc., 1969, 65, 1435-1442. [all data]

Wiberg, Crocker, et al., 1991
Wiberg, K.B.; Crocker, L.S.; Morgan, K.M., Thermochemical studies of carbonyl compounds. 5. Enthalpies of reduction of carbonyl groups, J. Am. Chem. Soc., 1991, 113, 3447-3450. [all data]

Diogo, Simoni, et al., 1993
Diogo, H.P.; Simoni, J.A.; Minas da Piedade, M.E.; Dias, A.R.; Martinho Simões, J.A., J. Am. Chem. Soc., 1993, 115, 2764. [all data]

Sharonov, Rozhnov, et al., 1995
Sharonov, K.G.; Rozhnov, A.M.; Korol'kov, A.V.; Karaseva, S.Y., Enthalpies of formation of 2-methyl-2-ethoxypropane and 2-ethyl-2-ethoxypropane from equilibrium measurements, J. Chem. Thermodyn., 1995, 27, 751-753. [all data]

Leal, Pires de Matos, et al., 1991
Leal, J.P.; Pires de Matos, A.; Martinho Simões, J.A., J. Organometal. Chem., 1991, 403, 1. [all data]

Rubtsov, 1986
Rubtsov, Yu.I., Thermodynamic calculation of equilibrium in nitration of alcohols, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1986, 19-22. [all data]

Rice and Greenberg, 1934
Rice, F.O.; Greenberg, J., Ketene. III. Heat of formation and heat of reaction with alcohols, J. Am. Chem. Soc., 1934, 38, 2268-2270. [all data]

Rodgers and Armentrout, 2000
Rodgers, M.T.; Armentrout, P.B., Noncovalent Metal-Ligand Bond Energies as Studied by Threshold Collision-Induced Dissociation, Mass Spectrom. Rev., 2000, 19, 4, 215, https://doi.org/10.1002/1098-2787(200007)19:4<215::AID-MAS2>3.0.CO;2-X . [all data]

Connett, 1972
Connett, J.E., Chemical equilibria 4. Enthalpy of dehydration of ethanol to diethyl ether by measurement of equilibrium constants in ethanol + ether+ water by a vapour flow technique, J. Chem. Thermodyn., 1972, 4, 135-138. [all data]


Notes

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