2-Ethylhexanoic acid

2-Ethylhexanoic acid
2-Ethylhexanoic acid molecule
Names
IUPAC name
2-Ethylhexanoic acid[1]
Identifiers
149-57-5 YesY
72377-05-0 S N
3D model (Jmol) Interactive image
1750468
ChEMBL ChEMBL1162485 YesY
ChEMBL1162487 N
ChEMBL1162486 N
ChemSpider 8373 YesY
70431 R N
119200 S N
ECHA InfoCard 100.005.222
EC Number 205-743-6
MeSH 2-ethylhexanoic+acid
PubChem 8697
78052 R
135309 S
RTECS number MO7700000
UNII 01MU2J7VVZ YesY
Properties
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
1.425
Thermochemistry
−635.1 kJ mol−1
-4.8013–4.7979 MJ mol−1
Hazards
GHS pictograms
GHS signal word DANGER
H312, H318, H361
P280, P305+351+338
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

Health aspects

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

References

  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.
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