Propionic acid

Propionic acid
General
Other names	Propanoic acid
Molecular formula	C3H6O2
SMILES	CCC(=O)O
Molar mass	74.08 g/mol
Appearance	colorless liquid
CAS number	[79-09-4]
EINECS number	201-176-3
Properties
Density and phase	0.99 g/cm3, liquid
Solubility in water	miscible
Melting point	−21°C
Boiling point	141°C
Acidity (pKa)	4.88
Viscosity	? cP at ? °C
Dipole moment	? D
Thermodynamic data
Standard enthalpy of formation ΔfH°solid	−510.8 kJ/mol
Standard enthalpy of combustion ΔcH°solid	? kJ/mol
Standard molar entropy S°solid	191.0 J.K–1.mol–1
Safety data
EU classification	Corrosive (C)
R-phrases	R34
S-phrases	S1/2, S23, S36, S45
PEL-TWA (OSHA)	—
Flash point	54°C
Autoignition temperature	485°C
Explosive limits	2.1–12%
RTECS number	UE5950000
Supplementary data page
Structure & properties	n, εr, etc.
Spectral data	UV, IR, NMR, MS
Related compounds
Other cations	Sodium propionate
Related carboxylic acids	Acetic acid Butyric acid
Related compounds	Methyl propionate
Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100 kPa) Infobox disclaimer and references

Propionic acid (systematically named propanoic acid) is a naturally occurring carboxylic acid with chemical formula CH₃CH₂COOH. In the pure state, it is a colorless, corrosive liquid with a sharp, somewhat unpleasant odor.

It is produced biologically from the metabolic breakdown of fatty acids containing odd numbers of carbon atoms, and also it the breakdown of some amino acids. Bacteria of the genus Propionibacterium produce propionic acid as the end product of their anaerobic metabolism. These bacteria are commonly found in the stomachs of ruminants, and their activity is partially responsible for the odor of both Swiss cheese and sweat.

Priopionic acid was first described in 1844 by Gottlieb, who found it among the degradation products of sugar. Over the next few years, other chemists produced propionic acid in various other ways, none of them realizing they were producing the same substance. In 1847, the French chemist Jean-Baptiste Dumas established that all the acids were the same compound, which he called propionic acid, from the Greek words protos and pion, meaning "first" and "fat" respectively, because it was the smallest acid that exhibited the properties of the other fatty acids, such as producing an oily layer when salted out of water and having a soapy potassium salt.

Contents

1 Properties 2 Production 3 Uses 4 Safety 5 External links

Properties

Priopionic acid has physical properties intermediate between those of the smaller carboxylic acids, formic and acetic acid, and the larger fatty acids. It is miscible with water, but it can be removed from water by adding salt. Like acetic and formic acids, its gas grossly violates the ideal gas law because it does not consist of individual propionic acid molecules, but instead of hydrogen bonded pairs of molecules. It also undergoes this pairing in solution.

Chemically, propionic acid displays the general properties of carboxylic acids, and like most other carboxylic acids, it can form amide, ester, anhydride, and chloride derivatives. It can react with chlorine or other halogens to replace one of the hydrogen atoms attached to its carbon atoms with a halogen atom.

Production

Industrially, propionic acid is usually made from the air oxidation of propionaldehyde. In the presence of cobalt or manganese ions, this reaction proceeds rapidly even at mild termperatures. Usually, the industrial process is carried out at 40-50°C, and is represented by the chemical equation

CH₃CH₂CHO + ½ O₂ → CH₃CH₂COOH

Large amounts of propionic acid were once produced as a byproduct of acetic acid manufacture, but changes in the way acetic acid is made have made this a very minor source of propionic acid today.

Uses

Propionic acid inhibits the growth of mold and some bacteria. Accordingly, most propionic acid produced is used as a preservative for both animal feed and food for human consumption. For animal feed, it is used either directly or as its ammonium salt. In human foods, especially bread and other baked goods, it is used as its sodium or calcium salt. Similar usage occurs in some of the older anti-fungal foot powders.

Propionic acid is also useful as a chemical intermediate. It can be used to modify synthetic cellulose fibers. It is also used to make pesticides and pharmaceuticals. The esters of propionic acid are sometimes used as solvents or artificial flavorings.

Safety

The chief danger from propionic acid is chemical burns that can result from contact with the concentrated liquid. In studies on laboratory animals, the only adverse health effect associated with long-term exposure to small amounts of propionic acid has been ulceration of the esophagus and stomach from consuming a corrosive substance. No toxic, mutagenic, carcinogenic, or reproductive effects have ever been observed. In the body, propionic acid is readily oxidized, metabolized, and eliminated from the body as carbon dioxide in the Krebs cycle, and so it does not bioaccumulate.

External links

• NIST Standard Reference Database (http://webbook.nist.gov/chemistry/)
• European Chemicals Bureau (http://ecb.jrc.it/)
• International Chemical Safety Card 0806 (http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc08/icsc0806.htm)
• NIOSH Pocket Guide to Chemical Hazards (http://www.cdc.gov/niosh/npg/npgd0529.html)de:Propionsäure

ja:プロピオン酸