Propanoic acid
| Propanoic acid | |
|---|---|
| propanoic acid | |
| Other names ethanecarboxylic acid, propionic acid | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 79-09-4 
|
| ChemSpider | 1005 |
| RTECS number | UE5950000 |
| SMILES | Script error: No such module "collapsible list". |
| style="background: #F8EABA; text-align: center;" colspan="2" | Properties | |
| Molecular formula | C3H6O2 |
| Molar mass | 74.08 g/mol |
| Appearance | colourless liquid |
| Density | 0.99 g/cm³ |
| Melting point |
−21 °C, 252 K, -6 °F |
| Boiling point |
141 °C, 414 K, 286 °F |
| Solubility in water | miscible |
| Acidity (pKa) | 4.87 |
| Viscosity | 10 mPa·s |
| style="background: #F8EABA; text-align: center;" colspan="2" | Structure | |
| Dipole moment | 0.63 D |
| style="background: #F8EABA; text-align: center;" colspan="2" | Hazards | |
| MSDS | External MSDS |
| R-phrases | R34 |
| S-phrases | (S1/2) S23 S36 S45 |
| NFPA 704 | |
| Flash point | 327 K, 54 °C |
| style="background: #F8EABA; text-align: center;" colspan="2" | Related compounds | |
| Other anions | propionate |
| Related carboxylic acids | acetic acid lactic acid 3-hydroxypropionic acid tartronic acid acrylic acid butyric acid |
| Related compounds | 1-propanol propionaldehyde sodium propionate propionic anhydride |
 (what is this?) (verify)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
Propanoic acid (also named propionic acid) is a naturally-occurring carboxylic acid with chemical formula CH3CH2COOH. It is a clear liquid with a pungent odor. The anion CH3CH2COO− as well as the salts and esters of propanoic acid are known as propanoates (or propionates).
Contents
History
Propanoic acid was first described in 1844 by Johann Gottlieb, who found it among the degradation products of sugar. Over the next few years, other chemists produced propanoic 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 = "first" and pion = "fat", because it was the smallest H(CH2)nCOOH 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.
Properties
Propanoic acid has physical properties intermediate between those of the smaller carboxylic acids, formic and acetic acids, and the larger fatty acids. It is miscible with water, but can be removed from water by adding salt. As with acetic and formic acids, it consists of hydrogen bonded pairs of molecules both as the liquid and vapor.
Propanoic acid displays the general properties of carboxylic acids: it can form amide, ester, anhydride, and chloride derivatives. It can undergo alpha-halogenation with bromine in the presence of PBr3 as catalyst (the HVZ reaction) to form CH3CHBrCOOH.[1]
Production
In industry, propanoic acid is mainly produced by the hydrocarboxylation of ethylene using nickel carbonyl as the catalyst:[2]
- H2C=CH2 + H2O + CO → CH3CH2CO2H
It is also produced by the aerobic oxidation of propionaldehyde. In the presence of cobalt or manganese ions, this reaction proceeds rapidly at temperatures as mild as 40–50 °C:
Large amounts of propanoic acid were once produced as a byproduct of acetic acid manufacture. Currently the world's largest producer of propanoic acid is BASF, with approximately 80 kt/a production capacity.
Propanoic acid is produced biologically as its coenzyme A ester, propionyl-CoA, from the metabolic breakdown of fatty acids containing odd numbers of carbon atoms, and also it is the breakdown of some amino acids. Bacteria of the genus Propionibacterium produce propanoic acid as the end product of their anaerobic metabolism. This class of bacteria is commonly found in the stomachs of ruminants and the sweat glands of humans, and their activity is partially responsible for the odor of both Swiss cheese and sweat.
Uses
Propanoic acid inhibits the growth of mold and some bacteria at the levels between 0.1 and 1% by weight. As a result, most propanoic acid produced is consumed 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. The antibiotic Monensin is added to cattle feed to favor propionibacteria over acetic acid producers in the rumen; this produces less carbon dioxide and feed conversion is better. This application accounts for about half of the world production of propanoic acid. Another major application is as a preservative in baked goods, which use the sodium and calcium salts.[2]
Propanoic acid is also useful as an intermediate in the production of other chemicals, especially polymers. Cellulose-acetate-propionate is a useful thermoplastic. Vinyl propionate is also used. In more specialized applications, it is also used to make pesticides and pharmaceuticals. The esters of propanoic acid have fruit-like odors and are sometimes used as solvents or artificial flavorings.[2]
Metabolism
The metabolism of propanoic acid begins with its conversion to propionyl coenzyme A (propionyl-CoA), the usual first step in the metabolism of carboxylic acids. Since propanoic acid has three carbons, propionyl-CoA cannot directly enter either beta oxidation nor the citric acid cycles. In most vertebrates, propionyl-CoA is carboxylated to D-methylmalonyl-CoA, which is isomerised to L-methylmalonyl-CoA. A vitamin B12-dependent enzyme catalyzes rearrangement of L-methylmalonyl-CoA to succinyl-CoA, which is an intermediate of the citric acid cycle and can be readily incorporated there.
In propanoic acidemia, propionate acts as a metabolic toxin in liver cells by accumulating in mitochondria as propionyl-CoA and its derivative, methylcitrate, two tricarboxylic acid cycle inhibitors. Propanoate is metabolized oxidatively by glia, which suggests astrocytic vulnerability in propanoic acidemia when intramitochondrial propionyl-CoA may accumulate. Propanoic acidemia may alter both neuronal and glial gene expression by affecting histone acetylation.[3][4] Propanoic acid in rodents produces reversible behavior (e.g. hyperactivity, dystonia, social impairment, perseveration) and brain (e.g. innate neuroinflammation, glutathione depletion) changes reminiscent of autism.[3]
Human occurrence
The human skin is host of several species of bacteria known as Propionibacteria, which are named after their ability to produce propanoic acid. The most notable one is the Propionibacterium acnes, which lives mainly in the sebaceous glands of the skin and is one of the principal causes of acne.
References
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<references />, or <references group="..." />External links
- NIST Standard Reference Database
- European Chemicals Bureau
- International Chemical Safety Card 0806
- NIOSH Pocket Guide to Chemical Hazards
- Technical data of propionic acid of BASF
de:Propionsäure el:Προπανικό οξύ es:Ácido propílico fr:Acide propanoïque it:Acido propionico la:Acidum propionicum lv:Propionskābe nl:Propionzuur ja:プロピオン酸 pl:Kwas propionowy pt:Ácido propanoico ru:Пропионовая кислота sk:Kyselina propiónová fi:Propionihappo sv:Propansyra vi:Axít prôpionic
zh:丙酸- ↑ C. S. Marvel and V. du Vigneaud (1943), "α-bromo-Isovaleric acid", Org. Synth.; Coll. Vol., 2: 93 Missing or empty
|title=(help) - ↑ 2.0 2.1 2.2 W. Bertleff, M. Roeper, X. Sava, “Carbonylation” in Ullmann’s Encyclopedia of Chemical Technology Wiley-VCH: Weinheim, 2003. DOI: 10.1002/14356007.a05 217.
- ↑ 3.0 3.1 D. F. MacFabe, D. P. Cain, K. Rodriguez-Capote, A. E. Franklin, J. E. Hoffman, F. Boon, A. R. Taylor, M. Kavaliers and K.-P. Ossenkopp (2007). "Neurobiological effects of intraventricular propionic acid in rats: Possible role of short-chain fatty acids on the pathogenesis and characteristics of autism spectrum disorders". Behavioral Brain Research. 176 (1): 149–169. doi:10.1016/j.bbr.2006.07.025.
- ↑ N. H. T. Nguyen, C. Morland, S. Villa Gonzalez, F. Rise, J. Storm-Mathisen, V. Gundersen, B. Hassel (2007). "Propionate increases neuronal histone acetylation, but is metabolized oxidatively by gli. Relevance for propionic acidemia". Journal of Neurochemistry. 101 (3): 806–814. doi:10.1111/j.1471-4159.2006.04397.x.
