Azelaic acid
- Formula: C9H16O4
- Molecular weight: 188.2209
- IUPAC Standard InChIKey: BDJRBEYXGGNYIS-UHFFFAOYSA-N
- CAS Registry Number: 123-99-9
- 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: Nonanedioic acid; Anchoic acid; Emerox 1144; Lepargylic acid; 1,7-Heptanedicarboxylic acid; Heptanedicarboxylic acid; Azelainic acid; Azelaic acid, technical grade; Emerox 1110; 1,9-Nonanedioic acid; 1,7-Dicarboxyheptane; n-Nonanedioic acid; Emery's L-110; Skinoren; ZK-62498; Finacea; NSC 19493
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Phase change data
Go To: Top, 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 379.7 | K | N/A | Khetarpal, Lal, et al., 1980 | Uncertainty assigned by TRC = 1. K; TRC |
Tfus | 380.0 | K | N/A | Cingolani and Berchiesi, 1974 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 119.7 ± 0.8 | kJ/mol | CGC | Roux, Temprado, et al., 2005 | Based on data from 434. to 503. K.; AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 159.9 ± 1.0 | kJ/mol | ME | Ribeiro da Silva, Monte, et al., 1999 | Based on data from 367. to 377. K.; AC |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
560.2 | 0.133 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
89.3 | 466. | A | Stephenson and Malanowski, 1987 | Based on data from 451. to 630. K. See also Stull, 1947.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
451.5 to 629.7 | 6.10311 | 3396.636 | -73.11 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
178. ± 5. | 348. to 373. | TPD | Cappa, Lovejoy, et al., 2007 | AC |
138. | 294. to 311. | TPTD | Chattopadhyay and Ziemann, 2005 | Values based on TPTD method are not consistent with values determined by other experimental methods; AC |
156.2 ± 0.5 | 372. | ME | Ribeiro da Silva, Monte, et al., 1999 | Based on data from 367. to 377. K.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
32.677 | 380.0 | N/A | Cingolani and Berchiesi, 1974 | DH |
35.3 | 375.6 | DSC | Chen, Xia, et al., 2009 | Authors explicitly state in the manuscript that no solid-solid phase transition was observed; AC |
29.7 | 372.4 | DSC | Roux, Temprado, et al., 2005 | AC |
32.67 | 380. | N/A | Acree, 1991 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
85.98 | 380.0 | Cingolani and Berchiesi, 1974 | DH |
References
Go To: Top, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Khetarpal, Lal, et al., 1980
Khetarpal, S.C.; Lal, K.; Bhatnagar, H.I.,
Indian J. Chem., Sect. A:Inorg., Phys., Theor. Anal., 1980, 19A, 516. [all data]
Cingolani and Berchiesi, 1974
Cingolani, A.; Berchiesi, G.,
Thermodynamic properties of organic compounds. 1. A DSC study of phase transitions in aliphatic dicarboxylic acids,
J. Therm. Anal., 1974, 6, 87-90. [all data]
Roux, Temprado, et al., 2005
Roux, Maria Victoria; Temprado, Manuel; Chickos, James S.,
Vaporization, fusion and sublimation enthalpies of the dicarboxylic acids from C4 to C14 and C16,
The Journal of Chemical Thermodynamics, 2005, 37, 9, 941-953, https://doi.org/10.1016/j.jct.2004.12.011
. [all data]
Ribeiro da Silva, Monte, et al., 1999
Ribeiro da Silva, Manuel A.V.; Monte, Manuel J.S.; Ribeiro, José R.,
Vapour pressures and the enthalpies and entropies of sublimation of five dicarboxylic acids,
The Journal of Chemical Thermodynamics, 1999, 31, 8, 1093-1107, https://doi.org/10.1006/jcht.1999.0522
. [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]
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]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Cappa, Lovejoy, et al., 2007
Cappa, Christopher D.; Lovejoy, Edward R.; Ravishankara, A.R.,
Determination of Evaporation Rates and Vapor Pressures of Very Low Volatility Compounds: A Study of the C 4 -C 10 and C 12 Dicarboxylic Acids,
J. Phys. Chem. A, 2007, 111, 16, 3099-3109, https://doi.org/10.1021/jp068686q
. [all data]
Chattopadhyay and Ziemann, 2005
Chattopadhyay, Sulekha; Ziemann, Paul J.,
Vapor Pressures of Substituted and Unsubstituted Monocarboxylic and Dicarboxylic Acids Measured Using an Improved Thermal Desorption Particle Beam Mass Spectrometry Method,
Aerosol Science and Technology, 2005, 39, 11, 1085-1100, https://doi.org/10.1080/02786820500421547
. [all data]
Chen, Xia, et al., 2009
Chen, Su-ning; Xia, Qing; Li, Dong; Yuan, Wei-Guang; Zhang, Feng-Bao; Zhang, Guo-Liang,
Solid-Liquid Equilibria of Nonanedioic Acid in Binary Ethanol + Water Solvent Mixtures from (292.35 to 345.52) K,
J. Chem. Eng. Data, 2009, 54, 4, 1395-1399, https://doi.org/10.1021/je800921n
. [all data]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [all data]
Notes
Go To: Top, Phase change data, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation 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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