Propionic acid

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Propanoic acid
Simplified skeletal formula
Full structural formula
Ball-and-stick model
Space-filling model
Names
IUPAC name
Propanoic acid
Other names
Ethanecarboxylic acid
Identifiers
79-09-4 YesY
ChEBI CHEBI:30768 YesY
ChEMBL ChEMBL14021 YesY
ChemSpider 1005 YesY
DrugBank DB03766 YesY
1062
Jmol 3D model Interactive image
Interactive image
PubChem 1032
RTECS number UE5950000
  • InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5) YesY
    Key: XBDQKXXYIPTUBI-UHFFFAOYSA-N YesY
  • CCC(=O)O
  • CCC(=O)O
Properties
C3H6O2
Molar mass 74.08 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) [3]
Boiling point 141.15 °C (286.07 °F; 414.30 K) [3]
Sublimes at −48 °C
ΔsublHo = 74 kJ/mol[4]
8.19 g/g (−28.3 °C)
34.97 g/g (−23.9 °C)
Miscible (≥ −19.3 °C)[5]
Solubility Miscible in EtOH, ether, CHCl3[6]
log P 0.33[7]
Vapor pressure 0.32 kPa (20 °C)[8]
0.47 kPa (25 °C)[7]
9.62 kPa (100 °C)[4]
4.45·10−4 L·atm/mol[7]
Acidity (pKa) 4.88[7]
Thermal conductivity 1.44·105 W/m·K
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)[7]
Structure
Monoclinic (−95 °C)[9]
P21/c[9]
a = 4.04 Å, b = 9.06 Å, c = 11 Å[9]
α = 90°, β = 91.25°, γ = 90°
0.63 D (22 °C)[2]
Thermochemistry
152.8 J/mol·K[6][4]
191 J/mol·K[4]
−510.8 kJ/mol[4]
1527.3 kJ/mol[2][4]
Vapor pressure {{{value}}}
Related compounds
Other anions
 Propanoate
Acetic acid
Lactic acid
3-hydroxypropionic acid
Tartronic acid
Acrylic acid
Butyric acid
Related compounds
 1-Propanol
Propionaldehyde
Sodium propionate
Propionic anhydride
Supplementary data page
Refractive index (n),
Dielectric constant (εr), etc.
Thermodynamic
data
 Phase behaviour
solid–liquid–gas
UV, IR, NMR, MS
YesY verify (what is YesYN ?)
Infobox references

Propionic acid (from the Greek words protos, meaning "first", and pion, meaning "fat"; also known as propanoic acid) is a naturally occurring carboxylic acid with chemical formula CH3CH2COOH. It is a clear liquid with a pungent and unpleasant smell somewhat resembling body odor. The anion CH3CH2COO− as well as the salts and esters of propionic acid are known as propionates (or propanoates).

History

Propionic 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 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 all the acids to be the same compound, which he called propionic acid, from the Greek words protos, meaning first, and pion, meaning fat, because it is the smallest H(CH2)nCOOH acid that exhibits 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

Propionic 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 as both the liquid and the vapor.

Propionic 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.[10]

Production

In industry, propionic acid is mainly produced by the hydrocarboxylation of ethylene using nickel carbonyl as the catalyst:[11]

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:

CH3CH2CHO + ½ O2 → CH3CH2COOH.

Large amounts of propionic acid were once produced as a byproduct of acetic acid manufacture. At the current time, the world's largest producer of propionic acid is BASF, with approximately 150 kt/a production capacity.

Propionic 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 from the breakdown of some amino acids. Bacteria of the genus Propionibacterium produce propionic 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.

It is also biosynthesized in the large intestine of humans by bacterial fermentation of dietary fibre.[12]

Industrial uses

Propionic acid inhibits the growth of mold and some bacteria at the levels between 0.1 and 1% by weight. As a result, most propionic 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 propionic acid. Another major application is as a preservative in baked goods, which use the sodium and calcium salts.[11] As a food additive, it is approved for use in the EU,[13] USA[14] and Australia and New Zealand.[15] It is listed by its INS number (280) or E number E280.

Propionic 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 propionic acid have fruit-like odors and are sometimes used as solvents or artificial flavorings.[11]

Biological uses

The metabolism of propionic acid begins with its conversion to propionyl coenzyme A (propionyl-CoA), the usual first step in the metabolism of carboxylic acids. Since propionic acid has three carbons, propionyl-CoA cannot directly enter either beta oxidation or 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 propionic acidemia, a rare inherited genetic disorder, 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 propionic acidemia when intramitochondrial propionyl-CoA may accumulate. Propionic acidemia may alter both neuronal and glial gene expression by affecting histone acetylation.[16][17] When propionic acid is infused directly into rodents' brains, it produces reversible behavior (e.g., hyperactivity, dystonia, social impairment, perseveration) and brain changes (e.g., innate neuroinflammation, glutathione depletion) that may be used as a means to model autism in rats.[16]

It also, being a three-carbon molecule, feeds into hepatic gluconeogenesis (that is, the creation of glucose molecules from simpler molecules in the liver).[18]

Human occurrence

The human skin is host of several species of bacteria known as Propionibacteria, which are named after their ability to produce propionic 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

  1. ↑ 1.0 1.1 Cite error: Invalid <ref> tag; no text was provided for refs named PGCH
  2. ↑ 2.0 2.1 2.2 2.3 2.4 Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ 3.0 3.1 Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ 4.0 4.1 4.2 4.3 4.4 4.5 Propanoic acid in Linstrom, P.J.; Mallard, W.G. (eds.) NIST Chemistry WebBook, NIST Standard Reference Database Number 69. National Institute of Standards and Technology, Gaithersburg MD. http://webbook.nist.gov (retrieved 2014-06-13)
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ 6.0 6.1 http://chemister.ru/Database/properties-en.php?dbid=1&id=1485
  7. ↑ 7.0 7.1 7.2 7.3 7.4 CID 1032 from PubChem
  8. ↑ Cite error: Invalid <ref> tag; no text was provided for refs named sigma
  9. ↑ 9.0 9.1 9.2 Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.; Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ 11.0 11.1 11.2 Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  16. ↑ 16.0 16.1 Lua error in package.lua at line 80: module 'strict' not found.
  17. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  18. ↑ Lua error in package.lua at line 80: module 'strict' not found.

External links

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