Decanedioic acid
- Formula: C10H18O4
- Molecular weight: 202.2475
- IUPAC Standard InChIKey: CXMXRPHRNRROMY-UHFFFAOYSA-N
- CAS Registry Number: 111-20-6
- 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: Sebacic acid; Decanedicarboxylic acid; 1,10-Decanedioic acid; 1,8-Octanedicarboxylic acid; Seracic acid; USAF HC-1; n-Decanedioic acid; NSC 19492; Ipomic acid
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Condensed phase thermochemistry data
Go To: Top, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔcH°solid | -5425.0 ± 2.1 | kJ/mol | Ccb | Verkade, Hartman, et al., 1926 | Reanalyzed by Cox and Pilcher, 1970, Original value = -5427.9 kJ/mol; See Verkade, Hartman, et al., 1924; Corresponding ΔfHºsolid = -1082.6 kJ/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
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 |
---|---|---|---|---|---|
Tfus | 404. | K | N/A | Berchiesi, 1981 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tfus | 405. | K | N/A | Khetarpal, Lal, et al., 1980 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tfus | 404.0 | K | N/A | Cingolani and Berchiesi, 1974 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 407. | K | N/A | Wynberg and Logothetis, 1956 | Uncertainty assigned by TRC = 2. K; TRC |
Tfus | 406.9 | K | N/A | Soffer, Strauss, et al., 1947 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 124.8 | kJ/mol | CGC | Roux, Temprado, et al., 2005 | Based on data from 424. to 503. K.; AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 161. ± 3. | kJ/mol | V | Davies and Thomas, 1960 | ALS |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
546.2 | 0.067 | Aldrich Chemical Company Inc., 1990 | BS |
568.2 | 0.133 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
85.9 | 471. | Stull, 1947 | Based on data from 456. to 625. K.; 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 |
---|---|---|---|---|---|
456. to 625.4 | 10.98636 | 9061.541 | 198.202 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
181. ± 8. | 353. to 385. | TPD | Cappa, Lovejoy, et al., 2007 | AC |
146.5 | 302. to 320. | TPTD | Chattopadhyay and Ziemann, 2005 | Values based on TPTD method are not consistent with values determined by other experimental methods; AC |
160.7 ± 2.5 | 389. | ME | Davies and Thomas, 1960 | Based on data from 375. to 403. K. See also Cox and Pilcher, 1970, 2 and Stephenson and Malanowski, 1987.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
40.807 | 404.0 | N/A | Cingolani and Berchiesi, 1974 | DH |
46.9 | 405.7 | N/A | Ventolà, Bayés, et al., 2008 | AC |
45.3 | 405.6 | DSC | Xia, Zhang, et al., 2008 | AC |
46.6 | 403.9 | N/A | Roux, Temprado, et al., 2005 | AC |
40.8 | 404. | N/A | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
101.0 | 404.0 | 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
C10H17O4- + =
By formula: C10H17O4- + H+ = C10H18O4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1364. ± 8.4 | kJ/mol | CIDC | Kumar, Prabhakar, et al., 2005 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1345. ± 8.4 | kJ/mol | CIDC | Kumar, Prabhakar, et al., 2005 | gas phase |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: Timothy J. Johnson, Tanya L. Myers, Yin-Fong Su, Russell G. Tonkyn, Molly Rose K. Kelly-Gorham, and Tyler O. Danby
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, 1994 |
NIST MS number | 133306 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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.
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]
Berchiesi, 1981
Berchiesi, M.A.,
Int. DATA Ser., Sel. Data Mixtures, Ser. A, 1981, No. 2, 126. [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]
Wynberg and Logothetis, 1956
Wynberg, H.; Logothetis, A.,
Studies in the Synthesis of Long-chain Compounds,
J. Am. Chem. Soc., 1956, 78, 1958. [all data]
Soffer, Strauss, et al., 1947
Soffer, M.D.; Strauss, N.S.; Trail, M.D.; Sherk, K.W.,
J. Am. Chem. Soc., 1947, 69, 1684. [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]
Davies and Thomas, 1960
Davies, M.; Thomas, G.H.,
The lattice energies, infra-red spectra, and possible cyclization of some dicarboxylic acids,
Trans. Faraday Soc., 1960, 56, 185. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]
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]
Cox and Pilcher, 1970, 2
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]
Ventolà, Bayés, et al., 2008
Ventolà, Lourdes; Bayés, Laura; Benages, Raül; Novegil-Anleo, Francisco Javier; Cuevas-Diarte, Miquel Ángel; Calvet, Teresa; Mondieig, Denise,
Decanedioic Acid (C 10 H 18 O 4 )/Dodecanedioic Acid (C 12 H 22 O 4 ) System: Polymorphism of the Components and Experimental Phase Diagram,
HCA, 2008, 91, 7, 1286-1298, https://doi.org/10.1002/hlca.200890140
. [all data]
Xia, Zhang, et al., 2008
Xia, Qing; Zhang, Feng-Bao; Zhang, Guo-Liang; Ma, Jian-Cheng; Zhao, Lei,
Solubility of Sebacic Acid in Binary Water + Ethanol Solvent Mixtures,
J. Chem. Eng. Data, 2008, 53, 3, 838-840, https://doi.org/10.1021/je7005314
. [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]
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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion 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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