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2-Ethylhexanoic acid

2-Ethylhexanoic acid

IUPAC name	2-Ethylhexanoic acid
Other names	2-Ethylcaproic acid, 3-heptanecarboxylic acid
Identifiers
CAS number	149-57-5
Properties
Molar mass	144.21 g/mol
Appearance	Colourless oil
Density	0.903 g/cm, solid
Melting point	-59 °C
Boiling point	228 °C
Solubility in water	low
Solubility	organic solvents
Hazards
Main hazards	flammable
R-phrases	63
S-phrases	36/37
Flash point	230 °F
Autoignition temperature	371 °C
Related Compounds
Related compounds	naphthenic acid, valproic acid
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

2-Ethylhexanoic acid is the organic compound with the formula CH₃(CH₂)₃CH(C₂H₅)CO₂H. This carboxylic acid is widely used to prepare metal derivatives that are soluble in nonpolar organic solvents. These lipophilic metal-containing derivatives are used as catalysts in polymerizations. For example, tin 2-ethylhexanoate is used in the production of poly(lactic-co-glycolic acid). The high solubility of these metal complexes is attributable to the long hydrocarbon chain and the presence of a chiral center which leads to mixtures of diastereoisomeric complexes. These metal complexes are often described as salts, when in fact they are not ionic but charge-neutral coordination complexes akin to the better defined, more crystalline acetates.

Additional recommended knowledge

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Examples of metal ethylhexanoates

Hydroxyl aluminium bis(2-ethylhexanoate), used as a thickener.
Tin(II) ethylhexanoate (CAS# 301-10-0) as a catalyst for polylactide polymerization.
Cobalt(II) ethylhexanoate (CAS# 136-52-7) as a drier for alkyd resins.
Nickel(II) ethylhexanoate ((CAS# 4454-16-4)

Health aspects

Some studies showed now subchronic oral toxicity.^[1] but as a studiy indicated the teratogenicity of the compound the sources for exposure where evaluated.^[2] One major source are the metal derivatives of 2-ethylhexanoic acid, which are widely used as stabilizers for polyvinyl chloride PVC. The other source is the metabolism of bis(2-ethylhexyl) phthalate (DEHP) the two ester bonds are hydrolysed and the resulting 2-ethylhexanol is oxidized in the organism to 2-ethylhexanoic acid. The elevated levels of the compound in even glass jars was due to the diffusion of the compound from the PVC cap into the food. ^[3]

References

^ Juberg DR, David RM, Katz GV, Bernard LG, Gordon DR, Vlaovic MS, Topping DC. (1998). "2-Ethylhexanoic acid: subchronic oral toxicity studies in the rat and mouse.". Food Chem Toxicol. 36 (5): 429-36.
^ Ritter, E. J., Scott, W. J. Jr, Randall, J. L. and Ritter, J.M. (1987). "Teratogenicity of di(2-ethylhexyl)phthalate, 2-ethylhexanol, 2-ethylhexanoic acid, and valproic acid, and potentiation by caffeine.". Teratology 35: 41–46.
^ S. Elss; L. Grünewald; E. Richling; P. Schreier (2004). "Occurrence of 2-ethylhexanoic acid in foods packed in glass jars". Food Additives & Contaminants 21 (8): 811 - 814. doi:10.1080/02652030410001732879.

Category: Fatty acids

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "2-Ethylhexanoic_acid". A list of authors is available in Wikipedia.