Pentanoic acid
- Formula: C5H10O2
- Molecular weight: 102.1317
- IUPAC Standard InChIKey: NQPDZGIKBAWPEJ-UHFFFAOYSA-N
- CAS Registry Number: 109-52-4
- 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: Valeric acid; n-Pentanoic acid; n-Valeric acid; Propylacetic acid; Valerianic acid; 1-Butanecarboxylic acid; n-C4H9COOH; Butanecarboxylic acid; Kyselina valerova; Valeric acid, normal; 1-Pentanoic acid; NSC 406833; Valeric acid, n-; NA 1760
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Condensed phase thermochemistry data
Go To: Top, Phase change 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:
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 |
---|---|---|---|---|---|
ΔfH°liquid | -133.6 ± 0.2 | kcal/mol | Ccb | Adriaanse, Dekker, et al., 1965 | DRB |
ΔfH°liquid | -133.90 ± 0.16 | kcal/mol | Ccb | Lebedeva, 1964 | ALS |
ΔfH°liquid | -133.9 ± 0.2 | kcal/mol | Ccb | Lebedeva, 1964 | DRB |
ΔfH°liquid | -130.6 ± 1.4 | kcal/mol | Ccb | Hancock, Watson, et al., 1954 | Reanalyzed by Cox and Pilcher, 1970, Original value = -131. kcal/mol; ALS |
ΔfH°liquid | -134.6 ± 0.31 | kcal/mol | Ccb | Schjanberg, 1937 | DRB |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -678.3 ± 0.2 | kcal/mol | Ccb | Adriaanse, Dekker, et al., 1965 | Corresponding ΔfHºliquid = -133.6 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -677.95 ± 0.16 | kcal/mol | Ccb | Lebedeva, 1964 | Corresponding ΔfHºliquid = -133.88 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -681.2 ± 1.4 | kcal/mol | Ccb | Hancock, Watson, et al., 1954 | Reanalyzed by Cox and Pilcher, 1970, Original value = -681. kcal/mol; Corresponding ΔfHºliquid = -130.63 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -677.20 ± 0.30 | kcal/mol | Ccb | Schjanberg, 1937 | Reanalyzed by Cox and Pilcher, 1970, Original value = -676.6 ± 1.0 kcal/mol; At 20 C; Corresponding ΔfHºliquid = -134.63 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 62.101 | cal/mol*K | N/A | McDougall and Kilpatrick, 1965 | DH |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -678.48 | kcal/mol | Ccb | Skuratov and Bonetskaya, 1966 | Corresponding ΔfHºsolid = -133.35 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
47.1 | 298.15 | Konicek and Wadso, 1971 | DH |
50.270 | 298.15 | McDougall and Kilpatrick, 1965 | T = 15 to 300 K.; DH |
Phase change data
Go To: Top, Condensed phase thermochemistry 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:
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 459. ± 2. | K | AVG | N/A | Average of 33 out of 40 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 239.7 | K | N/A | Adriaanse, Dekker, et al., 1964 | Uncertainty assigned by TRC = 0.1 K; TRC |
Tfus | 238.7 | K | N/A | Timmermans, 1935 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tfus | 238.65 | K | N/A | Timmermans, 1934 | Uncertainty assigned by TRC = 0.4 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 239.49 | K | N/A | McDougall and Kilpatrick, 1965, 2 | Uncertainty assigned by TRC = 0.06 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 644. ± 10. | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 35.83 | atm | N/A | Teja and Rosenthal, 1991 | Uncertainty assigned by TRC = 0.30 atm; TRC |
Pc | 35.81 | atm | N/A | Andereya and Chase, 1990 | Uncertainty assigned by TRC = 0.39 atm; TRC |
Pc | 35.53 | atm | N/A | Ambrose and Ghiassee, 1987 | Uncertainty assigned by TRC = 0.987 atm; TRC |
Pc | 35.178 | atm | N/A | D'Souza and Teja, 1987 | Uncertainty assigned by TRC = 0.89 atm; Ambrose's procedure; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 2.94 | mol/l | N/A | Teja and Anselme, 1990 | Uncertainty assigned by TRC = 0.06 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 16. ± 1. | kcal/mol | AVG | N/A | Average of 6 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
13.8 | 388. | EB | Ambrose and Ghiassee, 1987, 2 | Based on data from 373. to 465. K.; AC |
13.9 | 390. | A | Stephenson and Malanowski, 1987 | Based on data from 375. to 523. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
345.6 to 446.9 | 3.2018 | 879.771 | -172.237 | Kahlbaum, 1883 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
3.38470 | 239.49 | McDougall and Kilpatrick, 1965 | DH |
3.384 | 239.5 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
14.13 | 239.49 | McDougall and Kilpatrick, 1965 | DH |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Adriaanse, Dekker, et al., 1965
Adriaanse, N.; Dekker, H.; Coops, J.,
Heats of combustion of normal saturated fatty acids and their methyl esters,
Rec. Trav. Chim. Pays/Bas, 1965, 84, 393-407. [all data]
Lebedeva, 1964
Lebedeva, N.D.,
Heats of combustion of monocarboxylic acids,
Russ. J. Phys. Chem. (Engl. Transl.), 1964, 38, 1435-1437. [all data]
Hancock, Watson, et al., 1954
Hancock, C.K.; Watson, G.M.; Gilby, R.F.,
Heats of combustion of five-carbon fatty acids and their methyl and ethyl esters,
J. Phys. Chem., 1954, 58, 127-129. [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]
Schjanberg, 1937
Schjanberg, E.,
Die verbrennungswarmen und die refraktionsdaten einiger pentensaureeste,
Z. Phys. Chem., 1937, 178, 274-281. [all data]
McDougall and Kilpatrick, 1965
McDougall, L.A.; Kilpatrick, J.E.,
Entropy and related thermodynamic properties of n-valeric acid,
J. Chem. Phys., 1965, 42, 2307-2310. [all data]
Skuratov and Bonetskaya, 1966
Skuratov, S.M.; Bonetskaya, A.K.,
Enthalpy of formation of amide bonds,
Polym. Sci. USSR (Engl. Transl.), 1966, 8, 1754-1757. [all data]
Konicek and Wadso, 1971
Konicek, J.; Wadso, I.,
Thermochemical properties of some carboxylic acids, amines and N-substituted amides in aqueous solution,
Acta Chem. Scand., 1971, 25, 1541-1551. [all data]
Adriaanse, Dekker, et al., 1964
Adriaanse, N.; Dekker, H.; Coops, J.,
Some Physical Constants of Normal, Saturated Fatty Acids and Their Methyl Esters,
Recl. Trav. Chim. Pays-Bas, 1964, 83, 557. [all data]
Timmermans, 1935
Timmermans, J.,
Researches in Stoichiometry. I. The Heat of Fusion of Organic Compounds.,
Bull. Soc. Chim. Belg., 1935, 44, 17-40. [all data]
Timmermans, 1934
Timmermans, J.,
Theory of Concentrated Solutions XII.,
Bull. Soc. Chim. Belg., 1934, 43, 626. [all data]
McDougall and Kilpatrick, 1965, 2
McDougall, L.A.; Kilpatrick, J.E.,
Entropy and Related Thermodynamic Properties of n-Valeric Acid,
J. Chem. Phys., 1965, 42, 2307-10. [all data]
Teja and Rosenthal, 1991
Teja, A.S.; Rosenthal, D.J.,
The critical pressures and temperatures of ten substances using a low residence time flow apparatus
in Experimental Results for Phase Equilibria and Pure Component Properties, DIPPR DATA Series No. 1, 1991. [all data]
Andereya and Chase, 1990
Andereya, E.; Chase, J.D.,
Chem. Eng. Technol., 1990, 13, 304-12. [all data]
Ambrose and Ghiassee, 1987
Ambrose, D.; Ghiassee, N.B.,
Vapor Pressures and Critical Temperatures and Critical Pressures of Some Alkanoic Acids: C1 to C10,
J. Chem. Thermodyn., 1987, 19, 505. [all data]
D'Souza and Teja, 1987
D'Souza, R.; Teja, A.S.,
The prediction of the vapor pressures of carboxylic acids,
Chem. Eng. Commun., 1987, 61, 13. [all data]
Teja and Anselme, 1990
Teja, A.S.; Anselme, M.J.,
The critical properties of thermally stable and unstable fluids. I. 1985 results,
AIChE Symp. Ser., 1990, 86, 279, 115-21. [all data]
Ambrose and Ghiassee, 1987, 2
Ambrose, D.; Ghiassee, N.B.,
Vapour pressures and critical temperatures and critical pressures of some alkanoic acids: C1 to C10,
The Journal of Chemical Thermodynamics, 1987, 19, 5, 505-519, https://doi.org/10.1016/0021-9614(87)90147-9
. [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]
Kahlbaum, 1883
Kahlbaum, Georg W.A.,
Ueber die Abhängigkeit der Siedetemperatur vom Luftdruck,
Ber. Dtsch. Chem. Ges., 1883, 16, 2, 2476-2484, https://doi.org/10.1002/cber.188301602178
. [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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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