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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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | -252.0 ± 0.2 | kcal/mol | Ccb | Vasil'ev, Borodin, et al., 1991 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1141.0 ± 0.45 | kcal/mol | Ccb | Vasil'ev, Borodin, et al., 1991 | Corresponding ΔfHºsolid = -251.98 kcal/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°solid | -1141.4 | kcal/mol | Ccr | Sunner, 1946 | Corresponding ΔfHºsolid = -251.6 kcal/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°solid | -1141.00 ± 0.45 | kcal/mol | Ccb | Verkade, Hartman, et al., 1926 | Reanalyzed by Cox and Pilcher, 1970, Original value = -1141.7 kcal/mol; See Verkade, Hartman, et al., 1924; Corresponding ΔfHºsolid = -251.98 kcal/mol (simple calculation by NIST; no Washburn corrections) |
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
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° | 28.6 ± 0.2 | kcal/mol | CGC | Roux, Temprado, et al., 2005 | Based on data from 434. to 503. K.; AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 38.22 ± 0.24 | kcal/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 (atm) | Reference | Comment |
---|---|---|---|
560.2 | 0.132 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
21.3 | 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 (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
451.5 to 629.7 | 6.09740 | 3396.636 | -73.11 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
43. ± 1. | 348. to 373. | TPD | Cappa, Lovejoy, et al., 2007 | AC |
33.0 | 294. to 311. | TPTD | Chattopadhyay and Ziemann, 2005 | Values based on TPTD method are not consistent with values determined by other experimental methods; AC |
37.3 ± 0.1 | 372. | ME | Ribeiro da Silva, Monte, et al., 1999 | Based on data from 367. to 377. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
7.8100 | 380.0 | N/A | Cingolani and Berchiesi, 1974 | DH |
8.44 | 375.6 | DSC | Chen, Xia, et al., 2009 | Authors explicitly state in the manuscript that no solid-solid phase transition was observed; AC |
7.10 | 372.4 | DSC | Roux, Temprado, et al., 2005 | AC |
7.808 | 380. | N/A | Acree, 1991 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
20.55 | 380.0 | Cingolani and Berchiesi, 1974 | 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
C9H15O4- + =
By formula: C9H15O4- + H+ = C9H16O4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 323.6 ± 2.0 | kcal/mol | CIDC | Kumar, Prabhakar, et al., 2005 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 322.3 ± 2.0 | kcal/mol | CIDC | Kumar, Prabhakar, et al., 2005 | gas phase |
Gas phase ion energetics 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
De-protonation reactions
C9H15O4- + =
By formula: C9H15O4- + H+ = C9H16O4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 323.6 ± 2.0 | kcal/mol | CIDC | Kumar, Prabhakar, et al., 2005 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 322.3 ± 2.0 | kcal/mol | CIDC | Kumar, Prabhakar, et al., 2005 | gas phase |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
- SOLID (OIL MULL); BAIRD (GRATING); 2 cm-1 resolution
- SOLID (SPLIT MULL, FLUOROLUBE FOR 3800-1330 AND NUJOL FOR 1330-400 CM -1); BECKMAN IR-9 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
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 | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 113078 |
Gas Chromatography
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5MS | 1672.2 | Andriamaharavo, 2014 | 30. m/0.25 mm/0.25 μm, He; Program: 60C (1 min) => 5 C/min => 210C => 10 C/min => 280C (15 min) |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Subscription Links, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Vasil'ev, Borodin, et al., 1991
Vasil'ev, V.P.; Borodin, V.A.; Kopnyshev, S.B.,
Calculation of the standard enthalpies of combustion and of formation of crystalline organic acids and complexones from the energy contributions of atomic groups,
Russ. J. Phys. Chem. (Engl. Transl.), 1991, 65, 29-32. [all data]
Sunner, 1946
Sunner, S.,
Determination of combustion heats of organo-sulphur compounds,
Svensk. Kim. Tidr., 1946, 58, 71-81. [all data]
Verkade, Hartman, et al., 1926
Verkade, P.E.; Hartman, H.; Coops, J.,
Calorimetric researches. X. Heats of combustion of successive terms of homologous series: dicarboxylic acids of the oxalic acid series,
Rec. Trav. Chim. Pays/Bas, 1926, 45, 373-393. [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]
Verkade, Hartman, et al., 1924
Verkade, P.E.; Hartman, H.; Coops, J., Jr.,
Chemistry - The molecular heat of combustion of successive terms of homologous series,
Kom. Med. Akad. Ueknschap. Proc., 1924, 27, 859-866. [all data]
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]
Kumar, Prabhakar, et al., 2005
Kumar, M.R.; Prabhakar, S.; Nagaveni, V.; Vairamani, M.,
Estimation of gas-phase acidities of a series of dicarboxylic acids by the kinetic method,
Rapid Commun. Mass Spectrom., 2005, 19, 8, 1053-1057, https://doi.org/10.1002/rcm.1888
. [all data]
Andriamaharavo, 2014
Andriamaharavo, N.R.,
Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2014. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Subscription Links, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid 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 ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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