Butanal

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Condensed phase thermochemistry data

Go To: Top, Phase change data, Henry's Law data, Gas phase ion energetics 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
Δfliquid-58.66 ± 0.20kcal/molCmWiberg, Crocker, et al., 1991ALS
Δfliquid-56.90 ± 0.35kcal/molChydBuckley and Cox, 1967ALS
Δfliquid-57.43kcal/molCcbNicholson, 1960ALS
Δfliquid-57.06 ± 0.17kcal/molCcbTjebbes, 1960ALS
Quantity Value Units Method Reference Comment
Δcliquid-592.05 ± 0.34kcal/molCcbNicholson, 1960Corresponding Δfliquid = -57.41 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-592.42 ± 0.17kcal/molCcbTjebbes, 1960Corresponding Δfliquid = -57.04 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid58.01cal/mol*KN/AVasil'ev and Lebedev, 1989DH
liquid59.01cal/mol*KN/AParks, Kennedy, et al., 1956Extrapolation below 80 K, 43.93 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
39.36298.15Vasil'ev and Lebedev, 1989T = 11 to 330 K.; DH
39.080298.15Parks, Kennedy, et al., 1956T = 80 to 300 K.; DH

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
DRB - Donald R. Burgess, Jr.
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
Tboil348. ± 2.KAVGN/AAverage of 31 out of 33 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus176. ± 2.KAVGN/AAverage of 8 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple176.28KN/AVasil'ev and Lebedev, 1989, 2Uncertainty assigned by TRC = 0.02 K; corrected to 100 % purity by extrapolation; TRC
Ttriple176.8KN/AWilhoit, Chao, et al., 1985Uncertainty assigned by TRC = 0.2 K; TRC
Ttriple176.8KN/AParks, Kennedy, et al., 1956, 2Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Tc537.1KN/AAnselme and Teja, 1990Uncertainty assigned by TRC = 4. K; TRC
Tc537.2KN/ATeja and Rosenthal, 1990Uncertainty assigned by TRC = 0.8 K; TRC
Quantity Value Units Method Reference Comment
Pc42.64atmN/ATeja and Rosenthal, 1990Uncertainty assigned by TRC = 0.987 atm; TRC
Quantity Value Units Method Reference Comment
ρc3.88mol/lN/AAnselme and Teja, 1990Uncertainty assigned by TRC = 0.07 mol/l; TRC
Quantity Value Units Method Reference Comment
Δvap7.93kcal/molCGCChickos, Hosseini, et al., 1995Based on data from 313. to 353. K.; AC
Δvap8.03kcal/molN/AWiberg, Crocker, et al., 1991DRB
Δvap8.05 ± 0.1kcal/molEBBuckley and Cox, 1967, 2See also Verevkin, Krasnykh, et al., 2003.; AC
Δvap8.1 ± 0.1kcal/molVBuckley and Cox, 1967ALS
Δvap8.05kcal/molN/ABuckley and Cox, 1967DRB

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
8.17308.AStephenson and Malanowski, 1987Based on data from 293. to 349. K.; AC
7.86339.EBWojtasinski, 1963Based on data from 330. to 348. K.; AC
7.96319.N/ASeprakova, Paulech, et al., 1959Based on data from 304. to 347. K. See also Boublik, Fried, et al., 1984.; AC
8.10306.N/AKuchinskaya, 1938Based on data from 258. to 353. K.; AC

Antoine Equation Parameters

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

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Temperature (K) A B C Reference Comment
303.86 to 347.183.58541952.851-82.569Seprakova, Paulech, et al., 1959, 2Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
2.5748176.28Vasil'ev and Lebedev, 1989DH
2.651176.8Domalski and Hearing, 1996See also Vasil'ev and Lebedev, 1989, 2.; AC
2.6539176.8Parks, Kennedy, et al., 1956DH

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
14.61176.28Vasil'ev and Lebedev, 1989DH
15.01176.8Parks, Kennedy, et al., 1956DH

Enthalpy of phase transition

ΔHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.0184192.2liquidliquidVasil'ev and Lebedev, 1989T = 180 to 210 K.; DH
0.0152284.8liquidliquidVasil'ev and Lebedev, 1989T = 260 to 280 K.; DH

Entropy of phase transition

ΔStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
0.0927192.2liquidliquidVasil'ev and Lebedev, 1989T; DH
0.0533284.8liquidliquidVasil'ev and Lebedev, 1989T; DH

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:


Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/(kg*bar)) d(ln(kH))/d(1/T) (K) Method Reference Comment
9.66200.MN/AThe data from Table 1 by missing citation was used to redo the regression analysis. The data for acetone in their Table 2 is wrong.
5.44000.XN/A 
8.6 MButtery, Ling, et al., 1969 

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law data, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C4H8O+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.82 ± 0.04eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)189.5kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity181.8kcal/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
0.000694EFDDesfrancois, Abdoul-Carime, et al., 1994EA: 0.7 meV. Dipole-bound state.; B

Ionization energy determinations

IE (eV) Method Reference Comment
9.83PITraeger and McAdoo, 1986LBLHLM
9.8EIMcAdoo and Hudson, 1983LBLHLM
9.73 ± 0.015EIEl-Sherbini, Allam, et al., 1981LLK
9.836 ± 0.005PEHernandez, Masclet, et al., 1977LLK
9.73 ± 0.03PECocksey, Eland, et al., 1971LLK
9.86 ± 0.02PIWatanabe, Nakayama, et al., 1962RDSH
9.85PEBenoit and Harrison, 1977Vertical value; LLK
9.83PEKimura, Katsumata, et al., 1975Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H3O+10.19C2H5PITraeger and McAdoo, 1986LBLHLM
C2H4O+10.52C2H4EIHolmes, Terlouw, et al., 1976LLK
C3H5O+10.22?EIMouvier and Hernandez, 1975LLK

De-protonation reactions

C4H7O- + Hydrogen cation = Butanal

By formula: C4H7O- + H+ = C4H8O

Quantity Value Units Method Reference Comment
Δr364.8 ± 2.1kcal/molD-EAAlconcel, Deyerl, et al., 2001gas phase; B
Δr364.1 ± 2.3kcal/molD-EAZimmerman, Reed, et al., 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr358.2 ± 2.3kcal/molH-TSAlconcel, Deyerl, et al., 2001gas phase; B
Δr357.6 ± 2.5kcal/molH-TSZimmerman, Reed, et al., 1977gas phase; B

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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]

Buckley and Cox, 1967
Buckley, E.; Cox, J.D., Chemical equilibria. Part 2.-Dehydrogenation of propanol and butanol, Trans. Faraday Soc., 1967, 63, 895-901. [all data]

Nicholson, 1960
Nicholson, G.R., 478. The heats of combustion of butanal and heptanal, J. Chem. Soc., 1960, 2377-2378. [all data]

Tjebbes, 1960
Tjebbes, J., Heats of combustion of butannal and some related compounds, Acta Chem. Scand., 1960, 14, 180-188. [all data]

Vasil'ev and Lebedev, 1989
Vasil'ev, V.G.; Lebedev, B.V., Thermodynamics of butanal in the temperature range 0-330K, Zh. Obshch. Khim., 1989, 59(11), 2415-2420. [all data]

Parks, Kennedy, et al., 1956
Parks, G.S.; Kennedy, W.D.; Gates, R.R.; Mosley, J.R.; Moore, G.E.; Renquist, M.L., Thermal data on organic compounds. XXVI. Some heat capacity, entropy and free energy data for seven compounds containing oxygen., Not In System, 1956, 78, 56-59. [all data]

Vasil'ev and Lebedev, 1989, 2
Vasil'ev, V.G.; Lebedev, B.V., Thermodynamics of butanal in the temperature range 0-330 K, Zh. Obshch. Khim., 1989, 59, 11, 2415. [all data]

Wilhoit, Chao, et al., 1985
Wilhoit, R.C.; Chao, J.; Hall, K.R., Thermodynamic Properties of Key Organic Compounds in the Carbon Range C1 to C4. Part 1. Properties of Condensed Phases, J. Phys. Chem. Ref. Data, 1985, 14, 1. [all data]

Parks, Kennedy, et al., 1956, 2
Parks, G.S.; Kennedy, W.D.; Gates, R.R.; Mosley, J.R.; Moore, G.E.; Renquist, M.L., Thermal Data on Organic Compounds XXVI. Some Heat Capacity, Entropy and Free Energy Data for Seven Compounds Containing Oxygen, J. Am. Chem. Soc., 1956, 78, 56-9. [all data]

Anselme and Teja, 1990
Anselme, M.J.; Teja, A.S., The critical properties of rapidly reacting substances, AIChE Symp. Ser., 1990, 86, 279, 128-32. [all data]

Teja and Rosenthal, 1990
Teja, A.S.; Rosenthal, D.J., The Critical Pressures and Temperatures of Twelve Substances Using A Low Residence Time Flow Apparatus, AIChE Symp. Ser., 1990, 86, 279, 133-7. [all data]

Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G., Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times, Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3 . [all data]

Buckley and Cox, 1967, 2
Buckley, E.; Cox, J.D., Chemical equilibria. Part 2.?Dehydrogenation of propanol and butanol, Trans. Faraday Soc., 1967, 63, 895, https://doi.org/10.1039/tf9676300895 . [all data]

Verevkin, Krasnykh, et al., 2003
Verevkin, Sergey P.; Krasnykh, Eugen L.; Vasiltsova, Tatiana V.; Koutek, Bohumir; Doubsky, Jan; Heintz, Andreas, Vapor pressures and enthalpies of vaporization of a series of the linear aliphatic aldehydes, Fluid Phase Equilibria, 2003, 206, 1-2, 331-339, https://doi.org/10.1016/S0378-3812(03)00035-9 . [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]

Wojtasinski, 1963
Wojtasinski, Jerome G., Measurement of Total Pressures for Determining Liquid-Vapor Equilibrium Relations of the Binary System Isobutyraldehyde n-Butyraldehyde., J. Chem. Eng. Data, 1963, 8, 3, 381-385, https://doi.org/10.1021/je60018a028 . [all data]

Seprakova, Paulech, et al., 1959
Seprakova, M.; Paulech, J.; Dykyj, J., Chem. Zvesti, 1959, 13, 5, 313. [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Kuchinskaya, 1938
Kuchinskaya, K., Vapor pressures of pure substances, Sbornik Trudov Opytnogo Zavoda im. Akad. S. V. Lebedeva, 1938, 27-30. [all data]

Seprakova, Paulech, et al., 1959, 2
Seprakova, M.; Paulech, J.; Dykyj, J., Dampfdruck der Butyraldehyde, Chem. Zvesti, 1959, 13, 313-316. [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Buttery, Ling, et al., 1969
Buttery, R.G.; Ling, L.C.; Guadagni, D.G., Volatilities Aldehydes, Ketones, and Esters in Dilute Water Solution, J. Agric. Food Chem., 1969, 17, 385-389. [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Desfrancois, Abdoul-Carime, et al., 1994
Desfrancois, C.; Abdoul-Carime, H.; Khelifa, N.; Schermann, J.P., Fork 1/r to 1/r2 Potentials: Electron Exchange between Rydberg Atoms and Polar Molecules, Phys. Rev. Lett., 1994, 73, 18, 2436, https://doi.org/10.1103/PhysRevLett.73.2436 . [all data]

Traeger and McAdoo, 1986
Traeger, J.C.; McAdoo, D.J., Decomposition thresholds and associated translational energy releases for eight C4H8O+ isomers, Int. J. Mass Spectrom. Ion Processes, 1986, 68, 35. [all data]

McAdoo and Hudson, 1983
McAdoo, D.J.; Hudson, C.E., The decompositions of metastable [C4H8O]+ ions and the [C4H8O]+ potential surface, Org. Mass Spectrom., 1983, 18, 466. [all data]

El-Sherbini, Allam, et al., 1981
El-Sherbini, T.M.; Allam, S.H.; Migahed, M.D.; Dawoud, A.M., Mass spectrometric investigation of aliphatic aldehydes, Z. Naturforsch. A:, 1981, 36, 1334. [all data]

Hernandez, Masclet, et al., 1977
Hernandez, R.; Masclet, P.; Mouvier, G., Spectroscopie de photoelectrons d'aldehydes et de cetones aliphatiques, J. Electron Spectrosc. Relat. Phenom., 1977, 10, 333. [all data]

Cocksey, Eland, et al., 1971
Cocksey, B.J.; Eland, J.H.D.; Danby, C.J., The effect of alkyl substitution on ionisation potential, J. Chem. Soc., 1971, (B), 790. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Benoit and Harrison, 1977
Benoit, F.M.; Harrison, A.G., Predictive value of proton affinity. Ionization energy correlations involving oxygenated molecules, J. Am. Chem. Soc., 1977, 99, 3980. [all data]

Kimura, Katsumata, et al., 1975
Kimura, K.; Katsumata, S.; Yamazaki, T.; Wakabayashi, H., UV photoelectron spectra and sum rule consideration; out-of-plane orbitals of unsaturated compounds with planar-skeleton structure, J. Electron Spectrosc. Relat. Phenom., 1975, 6, 41. [all data]

Holmes, Terlouw, et al., 1976
Holmes, J.L.; Terlouw, J.K.; Lossing, F.P., The thermochemistry of C2H4O+ ions, J. Phys. Chem., 1976, 80, 2860. [all data]

Mouvier and Hernandez, 1975
Mouvier, G.; Hernandez, R., Ionisation and appearance potentials of alkylketones, Org. Mass Spectrom., 1975, 10, 958. [all data]

Alconcel, Deyerl, et al., 2001
Alconcel, L.S.; Deyerl, H.J.; Continetti, R.E., Effects of alkyl substitution on the energetics of enolate anions and radicals, J. Am. Chem. Soc., 2001, 123, 50, 12675-12681, https://doi.org/10.1021/ja0120431 . [all data]

Zimmerman, Reed, et al., 1977
Zimmerman, A.H.; Reed, K.J.; Brauman, J.I., Photodetachment of electrons from enolate anions. Gas phase electron affinities of enolate radicals, J. Am. Chem. Soc., 1977, 99, 7203. [all data]


Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, References