Maleic acid
- Formula: C4H4O4
- Molecular weight: 116.0722
- IUPAC Standard InChI: InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-
- IUPAC Standard InChIKey: VZCYOOQTPOCHFL-UPHRSURJSA-N
- CAS Registry Number: 110-16-7
- 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. - Stereoisomers:
- Other names: 2-Butenedioic acid (Z)-; cis-Butenedioic acid; cis-1,2-Ethylenedicarboxylic acid; Toxilic acid; (Z)-2-Butenedioic acid; Butenedioic acid,(Z)-; Maleinic acid; Malenic acid; 1,2-Ethylenedicarboxylic acid, (Z); 1,2-Ethylenedicarboxylic acid, cis-; Kyselina maleinova; (Z)-Butenedioic acid; 2-Butenedioic acid (2Z)-
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Phase change data
Go To: Top, Reaction thermochemistry data, 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:
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 | 402.9 | K | N/A | Wilhoit and Shiao, 1964 | Uncertainty assigned by TRC = 0.6 K; TRC |
| Tfus | 403.8 | K | N/A | Wilhoit and Shiao, 1964 | Uncertainty assigned by TRC = 0.5 K; TRC |
| Tfus | 416.65 | K | N/A | Skinner and Snelson, 1959 | Uncertainty assigned by TRC = 0.5 K; TRC |
| Tfus | 405. | K | N/A | Kern, Shriner, et al., 1925 | Uncertainty assigned by TRC = 2. K; TRC |
| Tfus | 403.4 | K | N/A | Weiss and Downs, 1923 | Uncertainty assigned by TRC = 0.6 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| Tc | 616.0 | K | N/A | Anselme and Teja, 1990 | Uncertainty assigned by TRC = 50. K; Tc > 616 K, which was observed with decomposition; TRC |
Enthalpy of sublimation
| ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 105.4 ± 1.7 | 368. | ME | Arshadi, 1974 | Based on data from 348. to 389. K.; AC |
| 110. ± 2.5 | 357. to 367. | N/A | Wolf and Weghofer, 1938 | See also Jones, 1960 and Cox and Pilcher, 1970.; AC |
| 110. ± 3. | 363. | V | Wolf and Weghofer, 1938, 2 | ALS |
| 109. ± 4.2 | 356. to 371. | N/A | Wolf and Trieschmann, 1934 | AC |
Enthalpy of fusion
| ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 26.9 | 411.9 | DSC | Guo, Sadiq, et al., 2010 | AC |
Reaction thermochemistry data
Go To: Top, Phase change data, 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
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
+
=
By formula: C4H4O4 + H2 = C4H6O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -151.8 ± 0.8 | kJ/mol | Chyd | Skinner and Snelson, 1959, 2 | liquid phase; solvent: Ethanol |
| ΔrH° | -153.2 ± 1.7 | kJ/mol | Chyd | Flitcroft, Skinner, et al., 1957 | liquid phase; Reanalyzed by Cox and Pilcher, 1970, 2, Original value = -152. ± 2. kJ/mol |
+
=
By formula: C4H2O3 + H2O = C4H4O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -34.9 ± 0.8 | kJ/mol | Cm | Conn, Kistiakowsky, et al., 1942 | liquid phase; Heat of hydroysis at 303 K |
References
Go To: Top, Phase change data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Wilhoit and Shiao, 1964
Wilhoit, R.C.; Shiao, D.,
Thermochemistry of Biologically Important Compounds. Heats of Combustion of Solid Organic Acids,
J. Chem. Eng. Data, 1964, 9, 595. [all data]
Skinner and Snelson, 1959
Skinner, H.A.; Snelson, A.,
Heats of Hydrogenation. Part 3,
Trans. Faraday Soc., 1959, 55, 404. [all data]
Kern, Shriner, et al., 1925
Kern, J.W.; Shriner, R.L.; Adams, R.,
Platinum and Palladium Oxides as Catalysts in the Reduction of Organic Compounds IX. The Reduction of Olefins,
J. Am. Chem. Soc., 1925, 47, 1147. [all data]
Weiss and Downs, 1923
Weiss, J.M.; Downs, C.R.,
The Physical Properties of Maleic, Fumaric and Malic Acids,
J. Am. Chem. Soc., 1923, 45, 1003. [all data]
Anselme and Teja, 1990
Anselme, M.J.; Teja, A.S.,
The critical properties of rapidly reacting substances,
AIChE Symp. Ser., 1990, 86, 279, 128-32. [all data]
Arshadi, 1974
Arshadi, Mohammed R.,
Determination of heats of sublimation of organic compounds by a mass spectrometric--knudsen effusion method,
J. Chem. Soc., Faraday Trans. 1, 1974, 70, 0, 1569, https://doi.org/10.1039/f19747001569
. [all data]
Wolf and Weghofer, 1938
Wolf, K.L.; Weghofer, H.Z.,
Z. Phys. Chem. Abt. B, 1938, 39, 194. [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
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]
Wolf and Weghofer, 1938, 2
Wolf, K.L.; Weghofer, H.,
Uber sublimationswarmen,
Z. Phys. Chem., 1938, 39, 194-208. [all data]
Wolf and Trieschmann, 1934
Wolf, K.L.; Trieschmann, H.G.,
Z. Phys. Chem. Abt. B, 1934, 27, 376. [all data]
Guo, Sadiq, et al., 2010
Guo, Kun; Sadiq, Ghazala; Seaton, Colin; Davey, Roger; Yin, Qiuxiang,
Co-Crystallization in the Caffeine/Maleic Acid System: Lessons from Phase Equilibria,
Crystal Growth & Design, 2010, 10, 1, 268-273, https://doi.org/10.1021/cg900885n
. [all data]
Skinner and Snelson, 1959, 2
Skinner, H.A.; Snelson, A.,
Heats of hydrogenation Part 3.,
Trans. Faraday Soc., 1959, 55, 405-407. [all data]
Flitcroft, Skinner, et al., 1957
Flitcroft, T.; Skinner, H.A.; Whiting, M.C.,
Heats of hydrogenation Part 1.-Dodeca-3:9 and -5:7 Diynes,
Trans. Faraday Soc., 1957, 53, 784-790. [all data]
Cox and Pilcher, 1970, 2
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Conn, Kistiakowsky, et al., 1942
Conn, J.B.; Kistiakowsky, G.B.; Roberts, R.M.; Smith, E.A.,
Heats of organic reactions. XIII. Heats of hydrolysis of some acid anhydrides,
J. Am. Chem. Soc., 1942, 64, 1747-17. [all data]
Notes
Go To: Top, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Tc Critical temperature Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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