Hexanedioic acid
- Formula: C6H10O4
- Molecular weight: 146.1412
- IUPAC Standard InChIKey: WNLRTRBMVRJNCN-UHFFFAOYSA-N
- CAS Registry Number: 124-04-9
- 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: Adipic acid; Acifloctin; Acinetten; Adilactetten; 1,4-Butanedicarboxylic acid; 1,6-Hexanedioic acid; Adipinic acid; Kyselina adipova; Adi-pure; NSC 7622; Hexanedioc acid
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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:
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°solid | -244.101 | kcal/mol | Ccb | Contineanu, Corlateanu, et al., 1980 | ALS |
ΔfH°solid | -238.58 ± 0.10 | kcal/mol | Ccb | Babinkov, Nistratov, et al., 1979 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -661.7 ± 1.4 | kcal/mol | Ccb | Contineanu, Corlateanu, et al., 1980 | Corresponding ΔfHºsolid = -244.152 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -667.30 ± 0.10 | kcal/mol | Ccb | Babinkov, Nistratov, et al., 1979 | Corresponding ΔfHºsolid = -238.58 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -668.23 ± 0.18 | kcal/mol | Ccr | Sunner, 1946 | Corresponding ΔfHºsolid = -237.65 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -669.80 ± 0.33 | kcal/mol | Ccb | Verkade, Hartman, et al., 1926 | Reanalyzed by Cox and Pilcher, 1970, Original value = -668.9 kcal/mol; See Verkade, Hartman, et al., 1924; Corresponding ΔfHºsolid = -236.08 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
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 |
---|---|---|---|---|---|
Tfus | 425. ± 4. | K | AVG | N/A | Average of 12 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 424.7 | K | N/A | Babinkov, Nistratov, et al., 1979, 2 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 25.14 | kcal/mol | CGC | Roux, Temprado, et al., 2005 | Based on data from 424. to 503. K.; AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 31.93 ± 0.31 | kcal/mol | ME | Ribeiro da Silva, Monte, et al., 1999 | See also Davies and Thomas, 1960.; AC |
ΔsubH° | 30.9 ± 0.3 | kcal/mol | V | Davies and Thomas, 1960 | ALS |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
538.2 | 0.132 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
22.0 | 447. | A | Stephenson and Malanowski, 1987 | Based on data from 432. to 611. K. See also Stull, 1947.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
432.7 to 610.7 | 5.46735 | 2813.066 | -95.951 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
29.8 ± 4.8 | 353. to 373. | ME | Taulelle, Sitja, et al., 2009 | AC |
34.7 ± 1. | 328. to 368. | TPD | Cappa, Lovejoy, et al., 2007 | AC |
34.94 | 285. to 307. | TPTD | Chattopadhyay and Ziemann, 2005 | AC |
33.5 | 295. to 318. | TPTD | Chattopadhyay, Tobias, et al., 2001 | Values based on TPTD method are not consistent with values determined by other experimental methods; AC |
30.90 ± 0.60 | 383. | ME | Nitta, Seki, et al., 1950 | Based on data from 359. to 406. K. See also Jones, 1960 and Cox and Pilcher, 1970, 2.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.3298 | 425.5 | Cingolani and Berchiesi, 1974 | DH |
8.05 | 419. | Roux, Temprado, et al., 2005 | AC |
8.329 | 426.4 | Acree, 1991 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
19.58 | 425.5 | Cingolani and Berchiesi, 1974 | DH |
Reaction thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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
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
C6H9O4- + =
By formula: C6H9O4- + H+ = C6H10O4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 325.1 ± 2.0 | kcal/mol | CIDC | Kumar, Prabhakar, et al., 2005 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 321.1 ± 2.0 | kcal/mol | CIDC | Kumar, Prabhakar, et al., 2005 | gas phase |
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 | Comment |
---|---|---|---|---|
2.0×10+8 | E | N/A | Value obtained by missing citation using the group contribution method. | |
1.8×10+7 | 11000. | X | N/A |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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
C6H9O4- + =
By formula: C6H9O4- + H+ = C6H10O4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 325.1 ± 2.0 | kcal/mol | CIDC | Kumar, Prabhakar, et al., 2005 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 321.1 ± 2.0 | kcal/mol | CIDC | Kumar, Prabhakar, et al., 2005 | gas phase |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, 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- 242 |
NIST MS number | 228440 |
Gas Chromatography
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law 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: 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 | VF-5MS | 1372.4 | Tret'yakov, 2007 | 30. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 2137. | Editorial paper, 2005 | Program: not specified |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Contineanu, Corlateanu, et al., 1980
Contineanu, I.; Corlateanu, E.; Hersocovici, J.; Marchidan, D.I.,
Combustion and formation enthalpies of 1,6-hexanediol and adipic acid,
Rev. Chim. (Bucharest), 1980, 31, 763-764. [all data]
Babinkov, Nistratov, et al., 1979
Babinkov, A.G.; Nistratov, V.P.; Larina, V.N.; Shvetsova, K.G.; Sapozhnikov, V.N.; Zhilitskaya, O.M.,
Thermodynamic properties of adipic acid,
Termodin. Org. Soedin., 1979, 28-33. [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]
Babinkov, Nistratov, et al., 1979, 2
Babinkov, A.G.; Nistratov, V.P.; Larina, V.N.; Shvetsova, K.G.; Sapozhnikov, V.N.; Zhilitskaya, O.M.,
Thermodynamic properties of aclipic acid.,
Termodin. Org. Soedin., 1979, No. 8, 28. [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]
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]
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]
Taulelle, Sitja, et al., 2009
Taulelle, Pascal; Sitja, Georges; Pepe, Gerard; Garcia, Eric; Hoff, Christian; Veesler, Stephane,
Measuring Enthalpy of Sublimation for Active Pharmaceutical Ingredients: Validate Crystal Energy and Predict Crystal Habit,
Crystal Growth & Design, 2009, 9, 11, 4706-4709, https://doi.org/10.1021/cg900567z
. [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]
Chattopadhyay, Tobias, et al., 2001
Chattopadhyay, Sulekha; Tobias, Herbert J.; Ziemann, Paul J.,
A Method for Measuring Vapor Pressures of Low-Volatility Organic Aerosol Compounds Using a Thermal Desorption Particle Beam Mass Spectrometer,
Anal. Chem., 2001, 73, 16, 3797-3803, https://doi.org/10.1021/ac010304j
. [all data]
Nitta, Seki, et al., 1950
Nitta, I.; Seki, S.; Momotani, M.; Suzuki, K.; Nakagawa, S.,
On the phase transition in pentaerythritol (II).,
Proc. Jpn. Acad., 1950, 26, 11. [all data]
Jones, 1960
Jones, A.H.,
Sublimation Pressure Data for Organic Compounds.,
J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019
. [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]
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]
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]
Tret'yakov, 2007
Tret'yakov, K.V.,
Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2007. [all data]
Editorial paper, 2005
Editorial paper,
Solid Phase Microextraction (SPME) Application Guide,
The Reporter Europe (Supelco), 2005, 16, 5, 12-12. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K 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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