2-Ethylhexanoic acid (2-EHA), commonly known as octoic acid,[2] 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.
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Names | |
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Preferred IUPAC name
2-Ethylhexanoic acid[1] | |
Identifiers | |
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3D model (JSmol) |
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1750468 | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.005.222 |
EC Number |
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MeSH | 2-ethylhexanoic+acid |
PubChem CID |
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RTECS number |
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UNII | |
CompTox Dashboard (EPA) |
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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 |
Refractive index (nD) |
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 labelling: | |
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Danger | |
H312, H318, H361 | |
P280, P305+P351+P338 | |
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): | |
LD50 (median dose) |
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Related compounds | |
Related compounds |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[3]
![Thumb](http://upload.wikimedia.org/wikipedia/commons/thumb/3/36/Co%28Ethexanoate%292.jpg/640px-Co%28Ethexanoate%292.jpg)
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.[4] They function as catalysts in polymerizations as well as for oxidation reactions as "oil drying agents."[5] 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
- 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).[6]
- Cobalt(II) ethylhexanoate (CAS# 136-52-7), a drier for alkyd resins
- Nickel(II) ethylhexanoate (CAS# 4454-16-4)[7]
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