Ethylhexanoate
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2-Ethylhexanoic acid (2-EHA), commonly known as octoic acid, is the
organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the
formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...
CH3(CH2)3CH(C2H5)CO2H. It is a
carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an Substituent, R-group. The general formula of a carboxylic acid is often written as or , sometimes as with R referring to an organyl ...
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 In chemistry, a racemic mixture or racemate () is a mixture that has equal amounts (50:50) of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as r ...
.


Production

2-Ethylhexanoic acid is produced industrially from
propylene Propylene, also known as propene, is an unsaturated organic compound with the chemical formula . It has one double bond, and is the second simplest member of the alkene class of hydrocarbons. It is a colorless gas with a faint petroleum-like o ...
, which is hydroformylated to give
butyraldehyde Butyraldehyde, also known as butanal, is an organic compound with the formula CH3(CH2)2CHO. This compound is the aldehyde derivative of butane. It is a colorless flammable liquid with an unpleasant smell. It is miscible with most organic solvents. ...
.
Aldol condensation An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties (of aldehydes or ketones) react to form a β-hydroxyaldehyde or β-hydroxyketone (an aldol reaction), and this is then followed by dehydration t ...
of the aldehyde gives 2-ethylhexenal, which is hydrogenated to give
2-ethylhexanal 2-Ethylhexanal is the organic compound with the formula . A colorless liquid, it is produced on a large scale industrially as a precursor to 2-ethylhexanoic acid and 2-ethylhexanol, both used as precursors to plasticizers. It was studied in the ...
. 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 Organic may refer to: * Organic, of or relating to an organism, a living entity * Organic, of or relating to an anatomical organ Chemistry * Organic matter, matter that has come from a once-living organism, is capable of decay or is the product ...
and industrial chemical synthesis. They function as
catalyst Catalysis () is the increase in rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quick ...
s in
polymer A polymer () is a chemical substance, substance or material that consists of very large molecules, or macromolecules, that are constituted by many repeat unit, repeating subunits derived from one or more species of monomers. Due to their br ...
izations as well as for
oxidation Redox ( , , reduction–oxidation or oxidation–reduction) is a type of chemical reaction in which the oxidation states of the reactants change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is ...
reactions as "
oil drying agent An oil drying agent, also known as siccative, is a coordination compound that accelerates ( catalyzes) the hardening of drying oils, often as they are used in oil-based paints. This so-called "drying" (actually a chemical reaction that produces a ...
s." 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 A coordination complex is a chemical compound consisting of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of bound molecules or ions, that are in turn known as ''ligands'' or ...
. Their structures are akin to the corresponding
acetate An acetate is a salt formed by the combination of acetic acid with a base (e.g. alkaline, earthy, metallic, nonmetallic, or radical base). "Acetate" also describes the conjugate base or ion (specifically, the negatively charged ion called ...
s.


Examples of metal ethylhexanoates

* Hydroxyl aluminium bis(2-ethylhexanoate), used as a thickener * Tin(II) ethylhexanoate (CAS# 301-10-0), a catalyst for
polylactide Polylactic acid, also known as poly(lactic acid) or polylactide (PLA), is a plastic material. As a thermoplastic polyester (or polyhydroxyalkanoate) it has the backbone formula or . PLA is formally obtained by condensation of lactic acid with ...
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

*
2-Ethylhexanol 2-Ethylhexanol (abbreviated 2-EH) is an organic compound with the chemical formula . It is a branched, eight-carbon chiral alcohol. It is a colorless liquid that is poorly soluble in water but soluble in most organic solvents. It is produced on a l ...


References

{{DEFAULTSORT:Ethylhexanoic acid, 2- Alkanoic acids