n-Decanoic acid
- Formula: C10H20O2
- Molecular weight: 172.2646
- IUPAC Standard InChIKey: GHVNFZFCNZKVNT-UHFFFAOYSA-N
- CAS Registry Number: 334-48-5
- 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: Decanoic acid; n-Capric acid; n-Decoic acid; n-Decylic acid; Capric acid; Caprinic acid; Caprynic acid; Decoic acid; Decylic acid; 1-Nonanecarboxylic acid; Nonane-1-carboxylic acid; neo-Fat 10; Hexacid 1095; Emery 659; Prifrac 296; 1-Decanoic acid; NSC 5025; Decanoic acid (capric acid)
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -149.2 ± 1.2 | kcal/mol | N/A | Adriaanse, Dekker, et al., 1965 | Value computed using ΔfHliquid° value of -713.7±0.9 kj/mol from Adriaanse, Dekker, et al., 1965 and ΔvapH° value of 89.5±5.0 kj/mol from n-alkanoic correlation. |
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 |
---|---|---|---|---|---|
ΔcH°liquid | -1453.0 ± 0.2 | kcal/mol | Ccb | Adriaanse, Dekker, et al., 1965 | Hfusion=29.4 kJ/mol; Corresponding ΔfHºliquid = -170.7 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
113.67 | 298.15 | Schaake, van Miltenburg, et al., 1982 | T = 80 to 345 K.; DH |
86.30 | 285. | Garner and Randall, 1924 | T = 0 to 65°C. Mean value 0 to 24°C.; 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 530. ± 60. | K | AVG | N/A | Average of 10 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 304. ± 2. | K | AVG | N/A | Average of 12 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 304.55 | K | N/A | Schaake, van Miltenburg, et al., 1982, 2 | Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 303.95 | K | N/A | Spizzichino, 1956 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ptriple | 9.60524×10-7 | atm | N/A | Spizzichino, 1956 | Uncertainty assigned by TRC = 2.6315×10-7 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 726. | K | N/A | Ambrose and Ghiassee, 1987 | Uncertainty assigned by TRC = 4. K; TRC |
Tc | 720.53 | 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 | 20.73 | atm | N/A | Ambrose and Ghiassee, 1987 | Uncertainty assigned by TRC = 3.95 atm; TRC |
Pc | 21.3347 | 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 |
ΔsubH° | 31. ± 1. | kcal/mol | TPD | Cappa, Lovejoy, et al., 2008 | AC |
ΔsubH° | 28.4 ± 0.5 | kcal/mol | V | Baccanari, Novinski, et al., 1968 | ALS |
ΔsubH° | 28.39 ± 0.53 | kcal/mol | ME | Baccanari, Novinski, et al., 1968 | Based on data from 293. to 303. K. See also Cox and Pilcher, 1970 and Stephenson and Malanowski, 1987.; AC |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
422.2 | 0.014 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
18.3 | 413. | A | Stephenson and Malanowski, 1987 | Based on data from 398. to 543. K.; AC |
21.2 | 314. | ME,TE | de Kruif, Schaake, et al., 1982 | Based on data from 305. to 323. K.; AC |
17.1 | 418. | 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 |
---|---|---|---|---|---|
426.0 to 460.3 | 2.4588 | 733.581 | -256.708 | Kahlbaum, 1894 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
27.99 ± 0.41 | 295. | ME | Davies and Malpass, 1961 | Based on data from 290. to 301. K.; AC |
28.0 ± 0.4 | 289.8 | V | Davies and Malpass, 1961, 2 | ALS |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
6.6898 | 304.4 | N/A | Garner and Randall, 1924 | DH |
6.76 | 303.8 | DSC | Moreno, Cordobilla, et al., 2007 | AC |
6.649 | 304.5 | N/A | Domalski and Hearing, 1996 | AC |
6.9830 | 300.1 | N/A | Eykman, 1889 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
22.0 | 304.4 | Garner and Randall, 1924 | DH |
23.3 | 300.1 | Eykman, 1889 | DH |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
6.6439 | 304.55 | crystaline, I | liquid | Schaake, van Miltenburg, et al., 1982 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
21.82 | 304.55 | crystaline, I | liquid | Schaake, van Miltenburg, et al., 1982 | 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 by: John E. Bartmess
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
C10H19O2- + =
By formula: C10H19O2- + H+ = C10H20O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 338.8 ± 2.0 | kcal/mol | TDEq | Norrman and McMahon, 1999 | gas phase; Folded form; dSacid = 7.2 eu |
ΔrH° | 346.1 ± 2.0 | kcal/mol | TDEq | Norrman and McMahon, 1999 | gas phase; Unfolded form |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 336.7 ± 2.1 | kcal/mol | H-TS | Norrman and McMahon, 1999 | gas phase; Folded form; dSacid = 7.2 eu |
ΔrG° | 338.8 ± 2.1 | kcal/mol | H-TS | Norrman and McMahon, 1999 | gas phase; Unfolded form |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: John E. Bartmess
De-protonation reactions
C10H19O2- + =
By formula: C10H19O2- + H+ = C10H20O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 338.8 ± 2.0 | kcal/mol | TDEq | Norrman and McMahon, 1999 | gas phase; Folded form; dSacid = 7.2 eu |
ΔrH° | 346.1 ± 2.0 | kcal/mol | TDEq | Norrman and McMahon, 1999 | gas phase; Unfolded form |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 336.7 ± 2.1 | kcal/mol | H-TS | Norrman and McMahon, 1999 | gas phase; Folded form; dSacid = 7.2 eu |
ΔrG° | 338.8 ± 2.1 | kcal/mol | H-TS | Norrman and McMahon, 1999 | gas phase; Unfolded form |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes
Data compiled by: Coblentz Society, Inc.
- LIQUID (NEAT); BECKMAN IR-4 (HYBRID PRISM-GRATING); DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY; 2 cm-1 resolution
- SOLID (MULL); Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm-1 resolution
- SOLUTION (10% CCl4 FOR 3800-1330, 10% CS2 FOR 1330-400 CM-1) $$ SEE SPECTRUM NO. 9966 FOR "NEAT" RUN; BECKMAN IR-9 (GRATING); DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW-1820 |
NIST MS number | 228813 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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]
Schaake, van Miltenburg, et al., 1982
Schaake, R.C.F.; van Miltenburg, J.C.; De Kruif, C.G.,
Thermodynamic properties of the normal alkanoic acids. II. Molar heat capacities of seven even-numbered normal alkanoic acids,
J. Chem. Thermodynam., 1982, 14, 771-778. [all data]
Garner and Randall, 1924
Garner, W.E.; Randall, F.C.,
Alternation in the heats of crystallization of the normal monobasic fatty acids. Part I.,
J. Chem. Soc., 1924, 125, 881-896. [all data]
Schaake, van Miltenburg, et al., 1982, 2
Schaake, R.C.F.; van Miltenburg, J.C.; De Kruif, C.G.,
Thermodynamic properties of the normal alkanoic acids. II. Molar heat capacities of seven even-numbered normal alkanoic acids.,
J. Chem. Thermodyn., 1982, 14, 771-8. [all data]
Spizzichino, 1956
Spizzichino, C.,
Contribution a l'etude des tensions de vapeur et des chaleurs de vaporisation des acides gras, esters methyliques et alcools gras a des pressions inferieures a 1 mm de mercure,
J. des Recherches du C.N.R.S., 1956, 34, 1-24. [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]
Cappa, Lovejoy, et al., 2008
Cappa, Christopher D.; Lovejoy, Edward R.; Ravishankara, A.R.,
Evaporation Rates and Vapor Pressures of the Even-Numbered C 8 -C 18 Monocarboxylic Acids,
J. Phys. Chem. A, 2008, 112, 17, 3959-3964, https://doi.org/10.1021/jp710586m
. [all data]
Baccanari, Novinski, et al., 1968
Baccanari, D.P.; Novinski, J.A.; Pan, Y.; Yevitz, M.M.; Swain, H.A., Jr.,
Heats of sublimation and vaporization at 25° of long chain fatty acids and methyl esters,
Trans. Faraday Soc., 1968, 64, 1201. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [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]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]
Cramer, 1943
Cramer, K.S.N.,
Chem. Zentr. II, 1943, 2234. [all data]
Kahlbaum, 1894
Kahlbaum, G.W.A.,
Studien uber Dampfspannkraftsmessungen,
Z. Phys. Chem. (Leipzig), 1894, 13, 14-55. [all data]
Davies and Malpass, 1961
Davies, Mansel; Malpass, V.E.,
212. Heats of sublimation of straight-chain monocarboxylic acids,
J. Chem. Soc., 1961, 1048, https://doi.org/10.1039/jr9610001048
. [all data]
Davies and Malpass, 1961, 2
Davies, M.; Malpass, V.E.,
Heats of sublimation of straight-chain monocarboxylic acids,
J. Chem. Soc., 1961, 1048-10. [all data]
Moreno, Cordobilla, et al., 2007
Moreno, Evelyn; Cordobilla, Raquel; Calvet, Teresa; Cuevas-Diarte, M.A.; Gbabode, Gabin; Negrier, Philippe; Mondieig, Denise; Oonk, Harry A.J.,
Polymorphism of even saturated carboxylic acids from n-decanoic to n-eicosanoic acid,
New J. Chem., 2007, 31, 6, 947, https://doi.org/10.1039/b700551b
. [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]
Eykman, 1889
Eykman, J.F.,
Zur kryoskopischen Molekulargewichtsbestimmung,
Z. Physik. Chem., 1889, 4, 497-519. [all data]
Norrman and McMahon, 1999
Norrman, K.; McMahon, T.B.,
Intramolecular solvation of carboxylate anions in the gas phase,
J. Phys. Chem. A, 1999, 103, 35, 7008-7016, https://doi.org/10.1021/jp9908202
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid Pc Critical pressure Ptriple Triple point pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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