Crotonic acid
- Formula: C4H6O2
- Molecular weight: 86.0892
- IUPAC Standard InChI: InChI=1S/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)
- IUPAC Standard InChIKey: LDHQCZJRKDOVOX-UHFFFAOYSA-N
- CAS Registry Number: 3724-65-0
- 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-Butenoic acid; α-Butenoic acid; 3-Methylacrylic acid; CH3CH=CHCOOH; α-Crotonic acid; β-Methylacrylic acid; Acrylic acid, 3-methyl-; Kyselina krotonova; UN 2823; But-2-enoic acid; NSC 206946; 2-Butenoic acid, isomer # 2
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Gas phase 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -88.07 ± 0.33 | kcal/mol | Ccb | Van-chin-syan, Kochubei, et al., 1996 |
Condensed phase 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | -105.3 ± 0.31 | kcal/mol | Ccb | Van-chin-syan, Kochubei, et al., 1996 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -475.81 ± 0.24 | kcal/mol | Ccb | Van-chin-syan, Kochubei, et al., 1996 | Corresponding ΔfHºsolid = -105.3 kcal/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°solid | -477.8 | kcal/mol | Ccb | Swietoslawski and Starczewska, 1928 | Heat of combustion corrected for constant pressure; Corresponding ΔfHºsolid = -103.3 kcal/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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tfus | 239.4 | K | N/A | Anonymous, 1955 | Uncertainty assigned by TRC = 0.6 K; TRC |
| Tfus | 345. | K | N/A | Timmermans, 1935 | Uncertainty assigned by TRC = 1.5 K; TRC |
| Tfus | 341. | K | N/A | Bruner, 1894 | Uncertainty assigned by TRC = 0.2 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 17.3 ± 0.1 | kcal/mol | C | Van-chin-syan, Kochubei, et al., 1996 | ALS |
| ΔsubH° | 17.3 | kcal/mol | N/A | Van-chin-syan, Kochubei, et al., 1996 | DRB |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-101 | 986. | Politeo, Jukic, et al., 2007 | 25. m/0.20 mm/0.20 μm, Helium, 70. C @ 2. min, 3. K/min, 200. C @ 15. min |
Van Den Dool and Kratz RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-20M | 1708. | Politeo, Jukic, et al., 2007 | 50. m/0.20 mm/0.20 μm, Helium, 70. C @ 4. min, 4. K/min, 180. C @ 15. min |
| Capillary | HP-20M | 1709. | Politeo, Jukic, et al., 2007, 2 | 50. m/0.2 mm/0.2 μm, He, 70. C @ 4. min, 4. K/min, 180. C @ 15. min |
| Capillary | DB-Wax | 1773. | Shiratsuchi, Shimoda, et al., 1993 | 60. m/0.25 mm/0.25 μm, 50. C @ 4. min, 2. K/min, 230. C @ 30. min |
| Capillary | DB-Wax | 1773. | Shiratsuchi, Shimoda, et al., 1993 | 60. m/0.25 mm/0.25 μm, 50. C @ 4. min, 2. K/min, 230. C @ 30. min |
Normal alkane RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-Wax | 1744. | Parada, Duque, et al., 2000 | 30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min, 240. C @ 10. min |
| Capillary | DB-Wax | 1763. | Parada, Duque, et al., 2000 | 30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min, 240. C @ 10. min |
| Capillary | DB-Wax | 1744. | Parada and Duque, 1998 | 30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min, 240. C @ 10. min |
| Capillary | DB-Wax | 1746. | Parada and Duque, 1998 | 30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min, 240. C @ 10. min |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Van-chin-syan, Kochubei, et al., 1996
Van-chin-syan, Yu.Ya.; Kochubei, V.V.; Sergeev, V.V.; Raevskii, Yu.A.; Gerasimchuk, S.I.; Kotovich, Kh.Z.,
Thermodynamic properties of some acids and aldehydes of the acrylic series,
Sov. J. Chem. Phys. (Engl. Transl.), 1996, 70, 1789-1794, In original 1932. [all data]
Swietoslawski and Starczewska, 1928
Swietoslawski, W.; Starczewska, H.,
Influence of certain corrections on the results of measurements of the heat of combustion of organic substances,
Bull. Int. Acad. Pol. Sci. Lett. Cl. Med., 1928, 85-97. [all data]
Anonymous, 1955
Anonymous, R.,
, Am. Pet. Inst. Res. Proj. 45, Tech. Rep. 14, No. 1, Ohio State Univ., 1955. [all data]
Timmermans, 1935
Timmermans, J.,
Researches in Stoichiometry. I. The Heat of Fusion of Organic Compounds.,
Bull. Soc. Chim. Belg., 1935, 44, 17-40. [all data]
Bruner, 1894
Bruner, L.,
The heats of fusion of some organic compounds,
Ber. Dtsch. Chem. Ges., 1894, 27, 2102. [all data]
Politeo, Jukic, et al., 2007
Politeo, O.; Jukic, M.; Milos, M.,
Chemical Composition and Antioxidant Activity of Free Volatile Aglycones from Laurel (Laurus nobilis L.) Compared to Its Essential Oil,
Croatica Chem. Acta, 2007, 80, 1, 121-126. [all data]
Politeo, Jukic, et al., 2007, 2
Politeo, O.; Jukic, M.; Milos, M.,
Chemical composition and antioxidant capacity of free volatile aglycones from basil (Ocimum basilicum L.) compared with its essential oil,
Food Chem., 2007, 101, 1, 379-385, https://doi.org/10.1016/j.foodchem.2006.01.045
. [all data]
Shiratsuchi, Shimoda, et al., 1993
Shiratsuchi, H.; Shimoda, M.; Minegishi, Y.; Osajima, Y.,
Isolation and identification of volatile flavor compounds in nonfermented coarse-cut sausage. Flavor as a quality factor of nonfermented sausage. 1,
J. Agric. Food Chem., 1993, 41, 4, 647-652, https://doi.org/10.1021/jf00028a027
. [all data]
Parada, Duque, et al., 2000
Parada, F.; Duque, C.; Fujimoto, Y.,
Free and bound volatile composition and characterization of some glucoconjugates as aroma precursors in Melón de olor fruit pulp (Sicana odorifera),
J. Agric. Food Chem., 2000, 48, 12, 6200-6204, https://doi.org/10.1021/jf0007232
. [all data]
Parada and Duque, 1998
Parada, F.; Duque, C.,
Studies on the aroma of piñuela fruit pulp (Bromelia plumieri): Free and bound volatile composition and characterization of some glucoconjugates as aroma precursors,
J. Hi. Res. Chromatogr., 1998, 21, 10, 577-581, https://doi.org/10.1002/(SICI)1521-4168(19981001)21:10<577::AID-JHRC577>3.0.CO;2-V
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, References
- Symbols used in this document:
Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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