|CAS number||, S|
|PubChem||, R, S|
|ChemSpider||, R , S|
|Jmol-3D images||Image 1
|Molar mass||144.21 g mol−1|
|Density||903 mg mL−1|
|Melting point||−59.00 °C; −74.20 °F; 214.15 K|
|Boiling point||228.1 °C; 442.5 °F; 501.2 K|
|Vapor pressure||<1 Pa (at 25 °C)|
|Refractive index (nD)||1.425|
|Std enthalpy of
|−635.1 kJ mol-1|
|Std enthalpy of
|-4.8013–4.7979 MJ mol-1|
|GHS signal word||DANGER|
|GHS hazard statements||H312, H318, H361|
|GHS precautionary statements||P280, P305+351+338|
|R-phrases||R20/21/22, R37/38, R41, R63|
|S-phrases||(S2), S26, S36/37/39|
|Flash point||114 °C (237 °F; 387 K)|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
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 enantiomeric 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.
Examples of metal ethylhexanoates
- Hydroxyl aluminium bis(2-ethylhexanoate), used as a thickener
- Tin(II) ethylhexanoate (CAS# 301-10-0), a catalyst for polylactide polymerization
- Cobalt(II) ethylhexanoate (CAS# 136-52-7), a drier for alkyd resins
- Nickel(II) ethylhexanoate (CAS# 4454-16-4)
Some studies showed now subchronic oral toxicity. but as a study indicated the teratogenicity of the compound the sources for exposure were evaluated. 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 even in glass jars was due to the diffusion of the compound from the PVC cap into the food. 
- "2-ethylhexanoic acid - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 21 February 2012.
- 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. doi:10.1016/S0278-6915(97)00168-3. PMID 9662418.
- 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 (1): 41–46. doi:10.1002/tera.1420350107. PMID 3105103.
- 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. PMID 15370833.