2-Ethylhexanoic acid
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| 2-Ethylhexanoic acid | |
|---|---|
 |
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| 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/cm3, 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 |
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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.
[edit] 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)
[edit] 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]
[edit] 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:.
