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2-Ethylhexanoic acid

2-Ethylhexanoic acid

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. Esters and salts of 2-EHA are called 2-ethylhexanoates, e.g. potassium 2-ethylhexanoate.

Production

2-Ethylhexanoic acid is produced industrially from butyraldehyde, which is obtained by hydroformylation of propylene. 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

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

Salts, esters, and coordination complexes derived from 2-ethylhexanoic acid are called 2-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. 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.

References

References

  1. (26 March 2005). "2-ethylhexanoic acid - Compound Summary". National Center for Biotechnology Information.
  2. (2000). "Economic Impact Analysis of Proposed Test Rule for 2-ethylhexanoic Acid (final) (epa Contract No. 68-01-6630).". Environmental Protection Agency, Washington, DC. Office of Toxic.
  3. (2002). "Carboxylic Acids, Aliphatic".
  4. (2007). "Metal 2-Ethylhexanoates and Related Compounds as Useful Precursors in Materials Science". Chemical Society Reviews.
  5. (2012). "Synthetic applications of 2-ethylhexanoic acid derived reagents". Tetrahedron.
  6. (2006). "Controlled Ring-Opening Polymerization to Biodegradable Aliphatic Polyester: Especially Poly(Β-Malic Acid) Derivatives". Prog. Polym. Sci..
  7. (2001). "Encyclopedia of Reagents for Organic Synthesis".
  8. {{CELEX
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