Valeric acid

Valeric acid or pentanoic acid is a straight-chain alkyl carboxylic acid with the chemical formula CH
3(CH
2)
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]

Valeric acid[1]
Names
IUPAC name
Pentanoic acid
Other names
Valeric acid
Butane-1-carboxylic acid
Valerianic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.344
RTECS number
  • YV6100000
UNII
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
Main hazards irritant
R-phrases (outdated) R34 R52/53
S-phrases (outdated) S26 S36 S45 S61
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
3
0
Flash point 86 °C (187 °F; 359 K)
Related compounds
Related compounds
 Butyric acid, Hexanoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

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.

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See also

References
  1. Merck Index, 12th Edition, 10042.
  2. Riemenschneider, Wilhelm (2002). "Carboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_235.
  3. 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.
  4. 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.
  5. Helferich, B.; Schaefer, W. (1929). "n-Butyryl Chloride". Org. Synth. 9: 32. doi:10.15227/orgsyn.009.0032.


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