Butanal
- Formula: C4H8O
- Molecular weight: 72.1057
- IUPAC Standard InChIKey: ZTQSAGDEMFDKMZ-UHFFFAOYSA-N
- CAS Registry Number: 123-72-8
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Butyraldehyde; n-Butanal; n-Butyl aldehyde; n-Butyraldehyde; Butal; Butaldehyde; Butanaldehyde; Butyl aldehyde; Butyral; Butyric aldehyde; Butyrylaldehyde; n-C3H7CHO; Aldehyde butyrique; Aldeide butirrica; Butalyde; Butyraldehyd; NCI-C56291; UN 1129; 1-Butanal; Butan-1-al; NSC 62779
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry 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 compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -211.8 ± 0.92 | kJ/mol | Cm | Wiberg, Crocker, et al., 1991 | ALS |
ΔfH°gas | -204.4 ± 1.4 | kJ/mol | Chyd | Buckley and Cox, 1967 | ALS |
ΔfH°gas | -206.7 | kJ/mol | N/A | Nicholson, 1960 | Value computed using ΔfHliquid° value of -240.3 kj/mol from Nicholson, 1960 and ΔvapH° value of 33.6 kj/mol from Wiberg, Crocker, et al., 1991.; DRB |
ΔfH°gas | -205.1 | kJ/mol | N/A | Tjebbes, 1960 | Value computed using ΔfHliquid° value of -238.7±0.7 kj/mol from Tjebbes, 1960 and ΔvapH° value of 33.6 kj/mol from Wiberg, Crocker, et al., 1991.; DRB |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 344.8 ± 4.2 | J/mol*K | N/A | Chermin, 1961 | This value calculated from calorimetric data is close to value of 345.5(2.3) J/mol*K obtained from equilibrium measurements [ Buckley E., 1967].; GT |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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 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 |
---|---|---|---|---|---|
ΔfH°liquid | -245.4 ± 0.84 | kJ/mol | Cm | Wiberg, Crocker, et al., 1991 | ALS |
ΔfH°liquid | -238.1 ± 1.5 | kJ/mol | Chyd | Buckley and Cox, 1967 | ALS |
ΔfH°liquid | -240.3 | kJ/mol | Ccb | Nicholson, 1960 | ALS |
ΔfH°liquid | -238.7 ± 0.71 | kJ/mol | Ccb | Tjebbes, 1960 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -2477.1 ± 1.4 | kJ/mol | Ccb | Nicholson, 1960 | Corresponding ΔfHºliquid = -240.2 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -2478.7 ± 0.71 | kJ/mol | Ccb | Tjebbes, 1960 | Corresponding ΔfHºliquid = -238.7 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 242.7 | J/mol*K | N/A | Vasil'ev and Lebedev, 1989 | DH |
S°liquid | 246.9 | J/mol*K | N/A | Parks, Kennedy, et al., 1956 | Extrapolation below 80 K, 43.93 J/mol*K.; DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
164.7 | 298.15 | Vasil'ev and Lebedev, 1989 | T = 11 to 330 K.; DH |
163.51 | 298.15 | Parks, Kennedy, et al., 1956 | T = 80 to 300 K.; DH |
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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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
C4H7O- + =
By formula: C4H7O- + H+ = C4H8O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1526. ± 8.8 | kJ/mol | D-EA | Alconcel, Deyerl, et al., 2001 | gas phase; B |
ΔrH° | 1523. ± 9.6 | kJ/mol | D-EA | Zimmerman, Reed, et al., 1977 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1499. ± 9.6 | kJ/mol | H-TS | Alconcel, Deyerl, et al., 2001 | gas phase; B |
ΔrG° | 1496. ± 10. | kJ/mol | H-TS | Zimmerman, Reed, et al., 1977 | gas phase; B |
By formula: NO- + C4H8O = (NO- • C4H8O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 164. | kJ/mol | ICR | Reents and Freiser, 1981 | gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M |
By formula: C6H14O2 + H2O = C4H8O + 2CH4O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 36.2 ± 0.1 | kJ/mol | Cm | Wiberg, Morgan, et al., 1994 | liquid phase; ALS |
ΔrH° | 36.53 ± 0.096 | kJ/mol | Eqk | Wiberg and Squires, 1981 | liquid phase; ALS |
By formula: H2 + C4H6O = C4H8O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -104.2 ± 0.42 | kJ/mol | Chyd | Dolliver, Gresham, et al., 1938 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -105.3 ± 0.4 kJ/mol; At 355°K; ALS |
(CAS Reg. No. 26232-84-8 • 4294967295) +
= CAS Reg. No. 26232-84-8
By formula: (CAS Reg. No. 26232-84-8 • 4294967295C4H8O) + C4H8O = CAS Reg. No. 26232-84-8
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 175. ± 9.2 | kJ/mol | N/A | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
By formula: C4H8O + H2 = C4H10O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -81.88 ± 0.75 | kJ/mol | Cm | Wiberg, Crocker, et al., 1991 | liquid phase; ALS |
ΔrH° | -70.5 ± 1.3 | kJ/mol | Chyd | Buckley and Cox, 1967 | gas phase; ALS |
By formula: Mg+ + C4H8O = (Mg+ • C4H8O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 280. ± 20. | kJ/mol | ICR | Operti, Tews, et al., 1988 | gas phase; switching reaction,Thermochemical ladder(Mg+)CH3OH; M |
By formula: C4H8O + 2CH4O = C6H14O2 + H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -59. ± 1. | kJ/mol | Cm | Wiberg, Morgan, et al., 1994 | gas phase; ALS |
By formula: 3C4H8O = C12H24O3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -29.45 | kJ/mol | Eqk | Ogorodnikov, Katsnel'son, et al., 1990 | liquid phase; PMR; ALS |
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) = k°H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
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)
k°H (mol/(kg*bar)) | d(ln(kH))/d(1/T) (K) | Method | Reference | Comment |
---|---|---|---|---|
9.6 | 6200. | M | N/A | The data from Table 1 by missing citation was used to redo the regression analysis. The data for acetone in their Table 2 is wrong. |
5.4 | 4000. | X | N/A | |
8.6 | M | Buttery, Ling, et al., 1969 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law 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]
Chermin, 1961
Chermin, H.A.G.,
Thermo data for petrochemicals. Part 27: Gaseous normal aldehydes. The important thermo properties are presented for all the gaseous normal aldehydes from formaldehyde through decaldehyde,
Pet. Refin., 1961, 40, 181-184. [all data]
Buckley E., 1967
Buckley E.,
Chemical equilibria. Part 2. Dehydrogenation of propanol and butanol,
Trans. Faraday Soc., 1967, 63, 895-901. [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]
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]
Reents and Freiser, 1981
Reents, W.D.; Freiser, B.S.,
Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes,
J. Am. Chem. Soc., 1981, 103, 2791. [all data]
Farid and McMahon, 1978
Farid, R.; McMahon, T.B.,
Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy,
Int. J. Mass Spectrom. Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0
. [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]
Wiberg and Squires, 1981
Wiberg, K.B.; Squires, R.R.,
Thermochemical studies of carbonyl reactions. 2. Steric effects in acetal and ketal hydrolysis,
J. Am. Chem. Soc., 1981, 103, 4473-4478. [all data]
Dolliver, Gresham, et al., 1938
Dolliver, M.A.; Gresham, T.L.; Kistiakowsky, G.B.; Smith, E.A.; Vaughan, W.E.,
Heats of organic reactions. VI. Heats of hydrogenation of some oxygen-containing compounds,
J. Am. Chem. Soc., 1938, 60, 440-450. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr.,
The gas phase acidity scale from methanol to phenol,
J. Am. Chem. Soc., 1979, 101, 6047. [all data]
Operti, Tews, et al., 1988
Operti, L.; Tews, E.C.; Freiser, B.S.,
Determination of Gas-Phase Ligand Binding Energies to Mg+ by FTMS Techniques,
J. Am. Chem. Soc., 1988, 110, 12, 3847, https://doi.org/10.1021/ja00220a020
. [all data]
Ogorodnikov, Katsnel'son, et al., 1990
Ogorodnikov, A.L.; Katsnel'son, M.G.; Pinson, V.V.; Levin, Yu.V.,
Study of thermodynamic characteristics of a butyraldehyde-cyclic trimer system,
Zh. Prikl. Khim. (Leningrad), 1990, 63, 1340-1343. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid S°gas Entropy of gas at standard conditions S°liquid Entropy of liquid at standard conditions d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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