2-Ethylhexanoic acid

Chembox new
ImageFile = 2-EtHex'oic.png IUPACName = 2-Ethylhexanoic acid
OtherNames = 2-Ethylcaproic acid, 3-heptanecarboxylic acid
Section1 = Chembox Identifiers
CASNo = 149-57-5
PubChem =
SMILES =
Section2 = Chembox Properties
Formula C₈H₁₆O₂
MolarMass = 144.21 g/mol
Appearance = Colourless oil
Density = 0.903 g/cm³, solid
MeltingPt = -59 °C
BoilingPt = 228 °C
Solubility = low
SolubleOther = organic solvents
Section3 = Chembox Hazards
MainHazards = flammable
FlashPt = 230 °F
Autoignition = 371 °C
RPhrases = 63
SPhrases = 36/37
Section4 = Chembox Related
OtherFunctn =
Function = ligand precursor
OtherCpds = naphthenic acid, valproic acid

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.

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. [cite journal
author = Juberg DR, David RM, Katz GV, Bernard LG, Gordon DR, Vlaovic MS, Topping DC.
title = 2-Ethylhexanoic acid: subchronic oral toxicity studies in the rat and mouse.
journal = Food Chem Toxicol.
volume = 36
issue = 5
pages = 429–36
year = 1998
doi = ] but as a studiy indicated the teratogenicity of the compound the sources for exposure where evaluated. [cite journal
author = Ritter, E. J., Scott, W. J. Jr, Randall, J. L. and Ritter, J.M.
title = Teratogenicity of di(2-ethylhexyl)phthalate, 2-ethylhexanol, 2-ethylhexanoic acid, and valproic acid, and potentiation by caffeine.
journal = Teratology
volume = 35
issue =
pages = 41–46
year = 1987
doi = ] 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. [cite journal
author = S. Elss; L. Grünewald; E. Richling; P. Schreier
title = Occurrence of 2-ethylhexanoic acid in foods packed in glass jars
journal = Food Additives & Contaminants
volume = 21
issue =8
pages = 811–814
year = 2004
doi = 10.1080/02652030410001732879 ]

References