2-Ethylhexanoic acid explained

2-Ethylhexanoic acid (2-EHA), commonly known as octoic acid,[1] 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 2-ethylhexanal. Oxidation of this aldehyde gives the carboxylic acid.

Metal ethylhexanoates

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.[2] 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

See also

Notes and References

  1. Economic Impact Analysis of Proposed Test Rule for 2-ethylhexanoic Acid (final) (epa Contract No. 68-01-6630). . 2000 . Environmental Protection Agency, Washington, DC. Office of Toxic . OTS0512911.
  2. 10.1039/B614334M . Metal 2-Ethylhexanoates and Related Compounds as Useful Precursors in Materials Science . 2007 . Mishra . Shashank . Daniele . Stéphane . Hubert-Pfalzgraf . Liliane G. . Chemical Society Reviews . 36 . 11 . 1770–1787 . 18213985 .
  3. Synthetic applications of 2-ethylhexanoic acid derived reagents. Raju, Ravinder. Prasad, Kapa. Tetrahedron. 2012. 68. 5. 1341–1349. 10.1016/j.tet.2011.10.078.
  4. Coulembier, O.. Degee, P.. Hedrick, J. L.. Dubois, P.. Controlled Ring-Opening Polymerization to Biodegradable Aliphatic Polyester: Especially Poly(Β-Malic Acid) Derivatives. Prog. Polym. Sci.. 2006. 31. 723–747. 10.1016/j.progpolymsci.2006.08.004.