2-Ethylhexanoic acid

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2-Ethylhexanoic acid
Skeletal formula of 2-ethylhexanoic acid
2-Ethylhexanoic acid molecule
IUPAC name
2-Ethylhexanoic acid[1]
149-57-5 YesY
72377-05-0 S N
ChEMBL ChEMBL1162485 YesY
ChEMBL1162487 N
ChEMBL1162486 N
ChemSpider 8373 YesY
70431 R N
119200 S N
EC Number 205-743-6
Jmol 3D model Interactive image
Interactive image
MeSH 2-ethylhexanoic+acid
PubChem 8697
78052 R
135309 S
RTECS number MO7700000
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
−635.1 kJ mol−1
-4.8013–4.7979 MJ mol−1
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
H312, H318, H361
P280, P305+351+338
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)
371 °C (700 °F; 644 K)
Explosive limits 0.9–6.7%
Lethal dose or concentration (LD, LC):
  • 1.142 g kg−1 (dermal, rabit)
  • 3 g kg−1 (oral, rat)
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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]

See also[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. & 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.