Propanedioic Acid - The NIST WebBook

Propanedioic acid

• Formula: C3H4O4
• Molecular weight: 104.0615
• IUPAC Standard InChI: InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7) Copy
• IUPAC Standard InChIKey: OFOBLEOULBTSOW-UHFFFAOYSA-N Copy
• CAS Registry Number: 141-82-2
• 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.
• Isotopologues:
  • [2H2]malonic [2H2]acid
• Other names: Malonic acid; Carboxyacetic acid; Dicarboxymethane; Methanedicarboxylic acid; CH2(COOH)2; USAF EK-695; Kyselina malonova; Methanedicarbonic acid; NSC 8124
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Henry's Law data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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: 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	408.05	K	N/A	Wilhoit and Shiao, 1964	Uncertainty assigned by TRC = 0.3 K; TRC
Tfus	407.9	K	N/A	Wilhoit and Shiao, 1964	Uncertainty assigned by TRC = 0.3 K; TRC
Quantity	Value	Units	Method	Reference	Comment
ΔsubH°	111.4 ± 0.7	kJ/mol	N/A	Ribeiro da Silva, Monte, et al., 1999	AC
ΔsubH°	105.1 ± 0.8	kJ/mol	C	Al-Takhin, Pilcher, et al., 1983	ALS

Enthalpy of sublimation

ΔsubH (kJ/mol)	Temperature (K)	Method	Reference	Comment
108.9 ± 0.7	348.	ME	Ribeiro da Silva, Monte, et al., 1999	Based on data from 339. to 357. K.; AC
72.7	306.	A	Stephenson and Malanowski, 1987	Based on data from 291. to 320. K. See also Granovskaya, 1947.; AC

Enthalpy of fusion

ΔfusH (kJ/mol)	Temperature (K)	Reference	Comment
23.1	407.5	Hansen and Beyer, 2004	AC

Enthalpy of phase transition

ΔHtrs (kJ/mol)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
0.01480	47.3	crystaline, III	crystaline, II	Fukai, Matsuo, et al., 1991	DH
1.837	352.2	crystaline, II	crystaline, I	Fukai, Matsuo, et al., 1991	DH
1.600	351.2	crystaline, II	crystaline, I	Petropavlov, Tsygankova, et al., 1988	DH

Entropy of phase transition

ΔStrs (J/mol*K)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
0.313	47.3	crystaline, III	crystaline, II	Fukai, Matsuo, et al., 1991	DH
5.217	352.2	crystaline, II	crystaline, I	Fukai, Matsuo, et al., 1991	DH
4.6	351.2	crystaline, II	crystaline, I	Petropavlov, Tsygankova, et al., 1988	DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

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References

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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]

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]

Al-Takhin, Pilcher, et al., 1983 Al-Takhin, G.; Pilcher, G.; Bickerton, J., Standard enthalpies of formation of diamine(dicarboxylato)platinum(II) complexes and of bis(pentane-2,4-dionato)platinum(II): the mean Pt-O bond dissociation enthalpies, J. Chem. Soc. Dalton Trans., 1983, 2657-2659. [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]

Granovskaya, 1947 Granovskaya, A., Russ. J. Phys. Chem., 1947, 21, 967. [all data]

Hansen and Beyer, 2004 Hansen, Anne R.; Beyer, Keith D., Experimentally Determined Thermochemical Properties of the Malonic Acid/Water System: Implications for Atmospheric Aerosols, J. Phys. Chem. A, 2004, 108, 16, 3457-3466, https://doi.org/10.1021/jp0376166 . [all data]

Fukai, Matsuo, et al., 1991 Fukai, M.; Matsuo, T.; Suga, H., Thermodynamic properties of phase transitions in malonic acid and its deuterated analog, Thermochim. Acta, 1991, 183, 215-243. [all data]

Petropavlov, Tsygankova, et al., 1988 Petropavlov, N.N.; Tsygankova, I.G.; Teslenko, L.A., Microcalorimetric investigation of polymorphic transitions in organic crystals, Sov. Phys. Crystallogr., 1988, 33(6), 853-855. [all data]

Notes

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• Symbols used in this document:

  Tfus	Fusion (melting) point
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔfusH	Enthalpy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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