2-Ethylhexanoic acid

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2-Ethylhexanoic acid
Skeletal formula of 2-ethylhexanoic acid
2-Ethylhexanoic acid molecule
Identifiers
CAS number 149-57-5 YesY, 72377-05-0 S YesY
PubChem 8697, 78052 R, 135309 S
ChemSpider 8373 YesY, 70431 R YesY, 119200 S YesY
UNII 01MU2J7VVZ YesY
EC number 205-743-6
MeSH 2-ethylhexanoic+acid
ChEMBL CHEMBL1162485 YesY, CHEMBL1162487 YesY, CHEMBL1162486 YesY
RTECS number MO7700000
Beilstein Reference 1750468
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C8H16O2
Molar mass 144.21 g mol−1
Appearance Colorless liquid
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
log P 2.579
Vapor pressure <1 Pa (at 25 °C)
Acidity (pKa) 4.819
Basicity (pKb) 9.178
Refractive index (nD) 1.425
Thermochemistry
Std enthalpy of
formation
ΔfHo298
−635.1 kJ mol-1
Std enthalpy of
combustion
ΔcHo298
-4.8013–4.7979 MJ mol-1
Hazards
GHS pictograms The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
GHS hazard statements H312, H318, H361
GHS precautionary statements P280, P305+351+338
EU Index 607-230-00-6
EU classification Harmful Xn
R-phrases R20/21/22, R37/38, R41, R63
S-phrases (S2), S26, S36/37/39
Flash point 114 °C (237 °F; 387 K)
Explosive limits 0.9–6.7%
LD50
  • 1.142 g kg-1 (dermal, rabit)
  • 3 g kg-1 (oral, rat)
Related compounds
Related compounds
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox 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 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[edit]

Health aspects[edit]

Some studies showed now subchronic oral toxicity.[2] but as a study indicated the teratogenicity of the compound the sources for exposure were evaluated.[3] 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. [4]

References[edit]

  1. ^ "2-ethylhexanoic acid - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 21 February 2012. 
  2. ^ 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. 
  3. ^ 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. 
  4. ^ 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.