Hexanoic acid
- Formula: C6H12O2
- Molecular weight: 116.1583
- IUPAC Standard InChIKey: FUZZWVXGSFPDMH-UHFFFAOYSA-N
- CAS Registry Number: 142-62-1
- 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: Caproic acid; n-Caproic acid; n-Hexanoic acid; n-Hexoic acid; n-Hexylic acid; Butylacetic acid; Capronic acid; Hexoic acid; Pentiformic acid; Pentylformic acid; 1-Pentanecarboxylic acid; CH3(CH2)4COOH; Pentane-1-carboxylic acid; 1-Hexanoic acid; Hexacid 698; Kyselina kapronova; Pentanecarboxylic acid; NSC 8266
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -122. ± 1. | kcal/mol | AVG | N/A | Average of 7 values; Individual data points |
Condensed phase 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -139.04 ± 0.25 | kcal/mol | Ccb | Fenwick, Harrop, et al., 1978 | ALS |
ΔfH°liquid | -139.48 ± 0.18 | kcal/mol | Ccb | Adriaanse, Dekker, et al., 1965 | Heat of formation derived by Cox and Pilcher, 1970; ALS |
ΔfH°liquid | -139.98 ± 0.13 | kcal/mol | Ccb | Lebedeva, 1964 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -835.16 ± 0.16 | kcal/mol | Ccb | Fenwick, Harrop, et al., 1978 | Corresponding ΔfHºliquid = -139.04 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -834.7 ± 0.1 | kcal/mol | Ccb | Adriaanse, Dekker, et al., 1965 | Corresponding ΔfHºliquid = -139.5 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -834.23 ± 0.13 | kcal/mol | Ccb | Lebedeva, 1964 | Corresponding ΔfHºliquid = -139.97 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -840.8 | kcal/mol | Ccb | Fischer and Wrede, 1904 | Heat of combustion corrected for pressure; Corresponding ΔfHºliquid = -133.4 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -841.97 | kcal/mol | Ccb | Lemoult, 1904 | Corresponding ΔfHºsolid = -132.2 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 |
---|---|---|---|
53.80 | 298. | von Reis, 1881 | T = 292 to 483 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 477. ± 4. | K | AVG | N/A | Average of 41 out of 42 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 269.7 | K | N/A | Adriaanse, Dekker, et al., 1964 | Uncertainty assigned by TRC = 0.05 K; TRC |
Tfus | 269.2 | K | N/A | Costello and Bowden, 1958 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 269. | K | N/A | Timmermans, 1935 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tfus | 269. | K | N/A | Gartenmeister, 1886 | Uncertainty assigned by TRC = 4. K; TRC |
Tfus | 271.4 | K | N/A | Gartenmeister, 1886 | Uncertainty assigned by TRC = 1.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 655.1 | K | N/A | Andereya and Chase, 1990 | Uncertainty assigned by TRC = 1. K; TRC |
Tc | 663. | K | N/A | Ambrose and Ghiassee, 1987 | Uncertainty assigned by TRC = 1. K; TRC |
Tc | 669.63 | K | N/A | D'Souza and Teja, 1987 | Uncertainty assigned by TRC = 3. K; Ambrose's procedure; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 33.33 | atm | N/A | Andereya and Chase, 1990 | Uncertainty assigned by TRC = 0.39 atm; TRC |
Pc | 31.58 | atm | N/A | Ambrose and Ghiassee, 1987 | Uncertainty assigned by TRC = 0.987 atm; TRC |
Pc | 31.1319 | 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 |
ΔvapH° | 16.5 ± 0.2 | kcal/mol | GS | Verevkin, 2000 | Based on data from 297. to 328. K.; AC |
ΔvapH° | 17.0 | kcal/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 353. to 393. K.; AC |
ΔvapH° | 17.5 ± 0.48 | kcal/mol | V | Kruif and Oonk, 1979 | ALS |
ΔvapH° | 17.5 ± 0.48 | kcal/mol | TE | Kruif and Oonk, 1979 | Based on data from 270. to 280. K.; AC |
ΔvapH° | 17.0 ± 0.3 | kcal/mol | V | Adriaanse, Dekker, et al., 1965 | Heat of formation derived by Cox and Pilcher, 1970; ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
16.3 ± 0.2 | 313. | GS | Verevkin, 2000 | Based on data from 297. to 328. K.; AC |
15.8 | 350. | A | Stephenson and Malanowski, 1987 | Based on data from 335. to 487. K. See also Dykyj, 1972.; AC |
16.9 | 271. | N/A | de Kruif, Schaake, et al., 1982 | AC |
15.9 | 386. | N/A | Rose, Acciarri, et al., 1957 | Based on data from 371. to 452. K. See also Boublik, Fried, et al., 1984.; AC |
15.4 | 367. | I | Cramer, 1943 | 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 |
---|---|---|---|---|---|
371.3 to 452.3 | 4.34282 | 1512.718 | -129.255 | Rose, Acciarri, et al., 1957 | Coefficents calculated by NIST from author's data. |
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 |
---|---|---|---|
1200. | 5900. | Q | N/A |
1400. | 6304. | M | N/A |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, 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 compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
≤10.12 | EI | Holmes, Fingas, et al., 1981 | LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H4O2+ | 10.52 ± 0.05 | C4H8 | EI | Holmes and Lossing, 1980 | LLK |
C2H402+ | 10.52 | 1-C4H8 | EI | Holmes and Lossing, 1980, 2 | LLK |
De-protonation reactions
C6H11O2- + =
By formula: C6H11O2- + H+ = C6H12O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 346.1 ± 2.1 | kcal/mol | G+TS | Caldwell, Renneboog, et al., 1989 | gas phase; B |
ΔrH° | 345.8 ± 2.4 | kcal/mol | G+TS | McLuckey, Cameron, et al., 1981 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 339.1 ± 2.0 | kcal/mol | IMRE | Caldwell, Renneboog, et al., 1989 | gas phase; B |
ΔrG° | 338.8 ± 2.3 | kcal/mol | CIDC | McLuckey, Cameron, et al., 1981 | gas phase; B |
References
Go To: Top, Gas phase thermochemistry data, 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.
Fenwick, Harrop, et al., 1978
Fenwick, J.O.; Harrop, D.; Head, A.J.,
Thermodynamic properties of organic oxygen compounds. 46. Enthalpies of formation of ethyl acetate and 1-hexanoix acid,
J. Chem. Thermodyn., 1978, 10, 687-690. [all data]
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]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]
Fischer and Wrede, 1904
Fischer, E.; Wrede, F.,
Uber die Verbrennungswarme einiger organischer Verbindungen,
Sitzungsber. Dtsch. Akad. Wiss. Berlin Kl. Math. Phys. Tech., 1904, 687-715. [all data]
Lemoult, 1904
Lemoult, M.P.,
Remarques sur une serie recenie de determinations calorimetriques,
Compt. Rend., 1904, 663-635. [all data]
von Reis, 1881
von Reis, M.A.,
Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht,
Ann. Physik [3], 1881, 13, 447-464. [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]
Costello and Bowden, 1958
Costello, J.M.; Bowden, S.T.,
The temperature variation of orthobaric density difference in liquid- vapour systems: IV fatty acids,
Recl. Trav. Chim. Pays-Bas, 1958, 77, 803. [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]
Gartenmeister, 1886
Gartenmeister, R.,
Investigation of the physical characterstics of liquid compounds: vi boiling point and specific volume of normal fatty acid esters,
Justus Liebigs Ann. Chem., 1886, 233, 249-315. [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]
Verevkin, 2000
Verevkin, S.P.,
Measurement and Prediction of the Monocarboxylic Acids Thermochemical Properties,
J. Chem. Eng. Data, 2000, 45, 5, 953-960, https://doi.org/10.1021/je990282m
. [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]
Kruif and Oonk, 1979
Kruif, C.G.; Oonk, H.A.J.,
Enthalpies of vaporization and vapour pressures of seven aliphatic carboxylic acids,
J. Chem. Thermodyn., 1979, 11, 287-290. [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]
Dykyj, 1972
Dykyj, J.,
Petrochemia, 1972, 12, 1, 13. [all data]
de Kruif, Schaake, et al., 1982
de Kruif, C.G.; Schaake, R.C.F.; van Miltenburg, J.C.; van der Klauw, K.; Blok, J.G.,
Thermodynamic properties of the normal alkanoic acids III. Enthalpies of vaporization and vapour pressures of 13 normal alkanoic acids,
The Journal of Chemical Thermodynamics, 1982, 14, 8, 791-798, https://doi.org/10.1016/0021-9614(82)90176-8
. [all data]
Rose, Acciarri, et al., 1957
Rose, Arthur.; Acciarri, Jerry A.; Johnson, R. Curtis.; Sanders, W.W.,
Automatic Computation of Antoine Equation 31 Constants---Caproic and Caprylic Acids and Methyl Esters,
Ind. Eng. Chem., 1957, 49, 1, 104-109, https://doi.org/10.1021/ie50565a036
. [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]
Cramer, 1943
Cramer, K.S.N.,
Chem. Zentr. II, 1943, 2234. [all data]
Holmes, Fingas, et al., 1981
Holmes, J.L.; Fingas, M.; Lossing, F.P.,
Towards a general scheme for estimating the heats of formation of organic ions in the gas phase. Part I. Odd-electron cations,
Can. J. Chem., 1981, 59, 80. [all data]
Holmes and Lossing, 1980
Holmes, J.L.; Lossing, F.P.,
Thermochemistry and unimolecular reactions of ionized acetic acid and its enol in the gas phase.,
J. Am. Chem. Soc., 1980, 102, 3732. [all data]
Holmes and Lossing, 1980, 2
Holmes, J.L.; Lossing, F.P.,
Gas-phase heats of formation of keto and enol ions of carbonyl compounds.,
J. Am. Chem. Soc., 1980, 102, 1591. [all data]
Caldwell, Renneboog, et al., 1989
Caldwell, G.; Renneboog, R.; Kebarle, P.,
Gas Phase Acidities of Aliphatic Carboxylic Acids, Based on Measurements of Proton Transfer Equilibria,
Can. J. Chem., 1989, 67, 4, 661, https://doi.org/10.1139/v89-092
. [all data]
McLuckey, Cameron, et al., 1981
McLuckey, S.A.; Cameron, D.; Cooks, R.G.,
Proton affinities from the dissociation of proton bound dimers,
J. Am. Chem. Soc., 1981, 103, 1313. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point 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 ΔcH°solid Enthalpy of combustion of solid 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 ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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