Propionic acid
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| Names | |||
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| Preferred IUPAC name
Propanoic acid | |||
| Other names
Carboxyethane
Ethanecarboxylic acid Ethylformic acid Metacetonic acid Methylacetic acid C3:0 (Lipid numbers) | |||
| Identifiers | |||
CAS Number
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3D model (JSmol)
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| ChEMBL |
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| DrugBank |
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| ECHA InfoCard | 100.001.070 | ||
| EC Number |
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| E number | E280 (preservatives) | ||
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PubChem CID
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CompTox Dashboard (EPA)
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InChI
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SMILES
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| Properties | |||
Chemical formula
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C3H6O2 | ||
| Molar mass | 74.079 g·mol−1 | ||
| Appearance | Colorless, oily liquid[1] | ||
| Odor | Pungent, rancid, unpleasant[1] | ||
| Density | 0.98797 g/cm3[2] | ||
| Melting point | −20.5 °C (−4.9 °F; 252.7 K)[8] | ||
| Boiling point | 141.15 °C (286.07 °F; 414.30 K)[8] | ||
Sublimation
conditions |
Sublimes at −48 °C ΔsublH | ||
Solubility in water
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8.19 g/g (−28.3 °C) 34.97 g/g (−23.9 °C) Miscible (≥ −19.3 °C)[4] | ||
| Solubility | Miscible in EtOH, ether, CHCl 3[5] | ||
| log P | 0.33[6] | ||
| Vapor pressure | 0.32 kPa (20 °C)[7] 0.47 kPa (25 °C)[6] 9.62 kPa (100 °C)[3] | ||
Henry's law
constant (kH) |
4.45·10−4 L·atm/mol[6] | ||
| Acidity (pKa) | 4.88[6] | ||
Magnetic susceptibility (χ)
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−43.50·10−6 cm3/mol | ||
Refractive index (nD)
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1.3843[2] | ||
| Viscosity | 1.175 cP (15 °C)[2] 1.02 cP (25 °C) 0.668 cP (60 °C) 0.495 cP (90 °C)[6] | ||
| Structure | |||
Crystal structure
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Monoclinic (−95 °C)[9] | ||
Space group
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P21/c[9] | ||
Lattice constant
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a = 4.04 Å, b = 9.06 Å, c = 11 Å[9] α = 90°, β = 91.25°, γ = 90°
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Dipole moment
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0.63 D (22 °C)[2] | ||
| Thermochemistry | |||
Heat capacity (C)
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152.8 J/mol·K[5][3] | ||
Std molar
entropy (S⦵298) |
191 J/mol·K[3] | ||
Std enthalpy of
formation (ΔfH⦵298) |
−510.8 kJ/mol[3] | ||
Std enthalpy of
combustion (ΔcH⦵298) |
1527.3 kJ/mol[2][3] | ||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards
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Corrosive | ||
| GHS labelling:[7] | |||
Pictograms
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Signal word
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Danger | ||
Hazard statements
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H314[7] | ||
Precautionary statements
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P280, P305+P351+P338, P310[7] | ||
| NFPA 704 (fire diamond) | |||
| Flash point | 54 °C (129 °F; 327 K)[7] | ||
Autoignition
temperature |
512 °C (954 °F; 785 K) | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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1370 mg/kg (mouse, oral)[5] | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible)
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none[1] | ||
REL (Recommended)
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TWA 10 ppm (30 mg/m3) ST 15 ppm (45 mg/m3)[1] | ||
IDLH (Immediate danger)
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N.D.[1] | ||
| Related compounds | |||
Related Carboxylic acids
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Acetic acid Lactic acid 3-Hydroxypropionic acid Tartronic acid Acrylic acid Butyric acid | ||
Related compounds
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1-Propanol Propionaldehyde Sodium propionate Propionic anhydride | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Propionic acid (/proʊpiˈɒnɪk/, from the Greek words πρῶτος : prōtos, meaning "first", and πίων : píōn, meaning "fat"; also known as propanoic acid) is a naturally occurring carboxylic acid with chemical formula CH
3CH
2CO
2H. It is a liquid with a pungent and unpleasant smell somewhat resembling body odor. The anion CH
3CH
2CO−
2 as well as the salts and esters of propionic acid are known as propionates or propanoates.
About half of the world production of propionic acid is consumed as a preservative for both animal feed and food for human consumption. It is also useful as an intermediate in the production of other chemicals, especially polymers.
- ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0529". National Institute for Occupational Safety and Health (NIOSH).
- ^ a b c d e Lagowski, J.J., ed. (2012). The Chemistry of Nonaqueous Solvents. Vol. III. Elsevier. p. 362. ISBN 978-0323151030.
- ^ a b c d e f Propanoic acid in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 13 June 2014)
- ^ Seidell, Atherton; Linke, William F. (1919). Solubilities of Inorganic and Organic Compounds (2nd ed.). D. Van Nostrand Company. p. 569.
- ^ a b c "chemister.ru (archived copy)". Archived from the original on 9 October 2016. Retrieved 13 June 2014.
- ^ a b c d e CID 1032 from PubChem
- ^ a b c d e Sigma-Aldrich Co., Propionic acid. Retrieved on 13 June 2014.
- ^ a b Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
- ^ a b c Strieter, F. J.; Templeton, D. H.; Scheuerman, R. F.; Sass, R. L. (1962). "The crystal structure of propionic acid". Acta Crystallographica. 15 (12): 1233–1239. Bibcode:1962AcCry..15.1233S. doi:10.1107/S0365110X62003278.