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)-
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
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:
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. - 389. K.; AC |
| 110. ± 2.5 | 357. - 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. - 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 |
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.
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]
Notes
Go To: Top, Phase change data, References
- Symbols used in this document:
Tc Critical temperature Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔsubH Enthalpy of sublimation - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.