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| Names | |
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| Preferred IUPAC name 2-Ethylhexanoic acid | |
| Identifiers | |
| CAS Number |
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| 3D model (JSmol) | |
| Beilstein Reference | 1750468 |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.005.222 
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| EC Number |
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| MeSH | 2-ethylhexanoic+acid |
| PubChem CID | |
| RTECS number |
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| UNII | |
| CompTox Dashboard (EPA) | |
InChI
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SMILES
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| Properties | |
| Chemical formula | C8H16O2 |
| Molar mass | 144.214 g·mol |
| Appearance | Colorless liquid |
| Density | 903 mg mL |
| 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 (ΔfH298) |
−635.1 kJ mol |
| Std enthalpy of combustion (ΔcH298) |
-4.8013–4.7979 MJ mol |
| Hazards | |
| GHS labelling: | |
| Pictograms |   
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| Signal word | Danger |
| Hazard statements | H312, H318, H361 |
| Precautionary statements | P280, P305+P351+P338 |
| Flash point | 114 °C (237 °F; 387 K) |
| Autoignition temperature |
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 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 N verify (what is ?)
Infobox references
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2-Ethylhexanoic acid (2-EHA), commonly known as octoic 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.
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 give 2-ethylhexanal. Oxidation of this aldehyde gives the carboxylic acid.
Metal ethylhexanoates
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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." 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).
- Cobalt(II) ethylhexanoate (CAS# 136-52-7), a drier for alkyd resins
- Nickel(II) ethylhexanoate (CAS# 4454-16-4)
Regulations
2-Ethylhexanoic acid is banned in the EU for use in cosmetics.
See also
References
- "2-ethylhexanoic acid - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 21 February 2012.
- Economic Impact Analysis of Proposed Test Rule for 2-ethylhexanoic Acid (final) (epa Contract No. 68-01-6630) (Report). Environmental Protection Agency, Washington, DC. Office of Toxic. 2000.
- Riemenschneider, Wilhelm (2002). "Carboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_235. ISBN 978-3527306732.
- Mishra, Shashank; Daniele, Stéphane; Hubert-Pfalzgraf, Liliane G. (2007). "Metal 2-Ethylhexanoates and Related Compounds as Useful Precursors in Materials Science". Chemical Society Reviews. 36 (11): 1770–1787. doi:10.1039/B614334M. PMID 18213985.
- Raju, Ravinder; Prasad, Kapa (2012). "Synthetic applications of 2-ethylhexanoic acid derived reagents". Tetrahedron. 68 (5): 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.
- Burrows, Cynthia J.; Wey, Shiow-Jyi (2001). "Nickel(II) 2-Ethylhexanoate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn014m. ISBN 0-471-93623-5.
- Commission Regulation (EU) 2023/1490 of 19 July 2023 amending Regulation (EC) No 1223/2009 of the European Parliament and of the Council as regards the use in cosmetic products of certain substances classified as carcinogenic, mutagenic or toxic for reproduction