2-Ethylhexanoic acid

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.

2-Ethylhexanoic acid
Names
IUPAC name
2-Ethylhexanoic acid[1]
Identifiers
3D model (JSmol)
1750468
ChEMBL
ChemSpider
ECHA InfoCard 100.005.222
EC Number
  • 205-743-6
MeSH 2-ethylhexanoic+acid
RTECS number
  • MO7700000
UNII
Properties
C8H16O2
Molar mass 144.214 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
Std enthalpy of
formation (ΔfH⦵298)
 −635.1 kJ mol−1
Std enthalpy of
combustion (ΔcH⦵298)
 -4.8013–4.7979 MJ mol−1
Hazards
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H312, H318, H361
P280, P305+351+338
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).
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Infobox references

Production

2-Ethylhexanoic acid is produced industrially from propylene, which is hydroformylated to give butyraldehyde. Aldol condensation of the aldehyde gives 2-ethylhexenal, which is hydrogenated to 2-ethylhexanal. Oxidation of this aldehyde gives the carboxylic acid.[2]

Metal ethylhexanoates
65% Solution of cobalt(II) bis(2-ethylhexanoate) in mineral spirits, tilted vial to illustrate color and viscosity.

2-Ethylhexanoic acid forms compounds with metal cations that have stoichiometry as metal acetates. These ethylhexanoate complexes are used in organic and industrial chemical synthesis. They function as catalysts in polymerizations as well as for oxidation reactions as "oil drying agents."[3] They are highly soluble in nonpolar solvents. These metal complexes 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
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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. Riemenschneider, Wilhelm (2002). "Carboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_235.
  3. 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.
  4. 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.
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