72377-05-0 S enantiomer
56006-48-5 R enantiomer
|3D model (Jmol)||Interactive image|
|Molar mass||144.21 g·mol−1|
|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|
|Vapor pressure||<1 Pa (at 25 °C)|
Refractive index (nD)
Std enthalpy of
|−635.1 kJ mol−1|
Std enthalpy of
|-4.8013–4.7979 MJ mol−1|
|GHS signal word||DANGER|
|H312, H318, H361|
EU classification (DSD)
|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)|
|Lethal dose or concentration (LD, LC):|
LD50 (median dose)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
2-Ethylhexanoic acid is the organic compound with the formula CH3(CH2)3CH(C2H5)CO2H. It is a carboxylic acid that is widely used to prepare lipophilic metal derivatives that are soluble in nonpolar organic solvents. 2-Ethylhexanoic acid is a colorless viscous oil. It is supplied as a racemic mixture.
These lipophilic metal-containing derivatives are used in many ways as catalysts in polymerizations, oxidation (drying agents), and organic synthesis. 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, which exist as mixtures of several diastereoisomer, are often described as salts. They are, however, not ionic but charge-neutral coordination complexes. Their structures are akin to the corresponding acetates.
Examples of metal ethylhexanoates
- Hydroxyl aluminium bis(2-ethylhexanoate), used as a thickener
- Tin(II) ethylhexanoate (CAS# 301-10-0), a catalyst for polylactide and poly(lactic-co-glycolic acid).
- Cobalt(II) ethylhexanoate (CAS# 136-52-7), a drier for alkyd resins
- Nickel(II) ethylhexanoate (CAS# 4454-16-4)
- "2-ethylhexanoic acid - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 21 February 2012.
- Wilhelm Riemenschneider "Carboxylic Acids, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a05_235.
- Raju, Ravinder; Prasad, Kapa (2012). "Synthetic applications of 2-ethylhexanoic acid derived reagents". Tetrahedron. 68: 1341–1349. doi:10.1016/j.tet.2011.10.078.
- Coulembier, O.; Degee, P.; Hedrick, J. L.; Dubois, P. (2006). "Controlled Ring-Opening Polymerization to Biodegradable Aliphatic Polyester: Especially Poly(Β-Malic Acid) Derivatives". Prog. Polym. Sci. 31: 723–747. doi:10.1016/j.progpolymsci.2006.08.004.