My watch list

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

Safe Weighing Range Ensures Accurate Results

Daily Visual Balance Check

Daily Sensitivity Test

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.