Valeric acid
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Names | |
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IUPAC name
Pentanoic acid
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Other names
Valeric acid
Butane-1-carboxylic acid Valerianic acid | |
Identifiers | |
3D model (JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.003.344 |
PubChem CID
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RTECS number |
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C5H10O2 | |
Molar mass | 102.133 g·mol−1 |
Appearance | Colorless liquid |
Density | 0.930 g/cm3 |
Melting point | −34.5 °C (−30.1 °F; 238.7 K) |
Boiling point | 186 to 187 °C (367 to 369 °F; 459 to 460 K) |
4.97 g/100 mL | |
Acidity (pKa) | 4.82 |
-66.85·10−6 cm3/mol | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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irritant |
NFPA 704 (fire diamond) | |
Flash point | 86 °C (187 °F; 359 K) |
Related compounds | |
Related compounds
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Butyric acid, Hexanoic acid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Valeric acid or pentanoic acid is a straight-chain alkyl carboxylic acid with the chemical formula CH3(CH2)3COOH. Like other low-molecular-weight carboxylic acids, it has an unpleasant odor. It is found in the perennial flowering plant valerian (Valeriana officinalis), from which it gets its name. Its primary use is in the synthesis of its esters. Salts and esters of valeric acid are known as valerates or pentanoates. Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Ethyl valerate and pentyl valerate are used as food additives because of their fruity flavors.[2]
Production
It is produced industrially by the oxidation of valeraldehyde.[2] It can be produced from biomass-derived sugars via levulinic acid.[3]
Valeric acid is one volatile component in swine manure. Other components include other carboxylic acids, skatole, trimethyl amine, and isovaleric acid.[4]
It undergoes chlorination to give valeryl chloride.[5]
Safety
Valeric acid can cause irritation if it comes into contact with the skin, eyes, or mucous membranes.
See also
![](http://upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/40px-Wiktionary-logo-en-v2.svg.png)
- List of saturated fatty acids
- 4-Hydroxy-4-methylpentanoic acid
- Pivalic acid (2,2-dimethylpropanoic acid)
- 3-Methylbutanoic acid, also called isovaleric acid
References
- ^ Merck Index, 12th Edition, 10042.
- ^ a b Riemenschneider, Wilhelm (2002). "Carboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_235. ISBN 978-3527306732.
- ^ Yan, Long; Yao, Qian; Fu, Yao (2017). "Conversion of levulinic acid and alkyl levulinates into biofuels and high-value chemicals". Green Chemistry. 19 (23): 5527–5547. doi:10.1039/C7GC02503C.
- ^ Ni, Ji-Qin; Robarge, Wayne P.; Xiao, Changhe; Heber, Albert J. (2012). "Volatile organic compounds at swine facilities: A critical review". Chemosphere. 89 (7): 769–788. doi:10.1016/j.chemosphere.2012.04.061. PMID 22682363.
- ^ Helferich, B.; Schaefer, W. (1929). "n-Butyryl Chloride". Org. Synth. 9: 32. doi:10.15227/orgsyn.009.0032.