2-Ethylhexanoic acid is the

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

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 betwee ...

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 R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic ...

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 one that has equal amounts 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 racemates. ...

Production

2-Ethylhexanoic acid is produced industrially from

propylene Propylene, also known as propene, is an unsaturated organic compound with the chemical formula CH3CH=CH2. 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 petrole ...

, 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 to ...

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 acetate Transition metal carboxylate complexes are coordination complexes with carboxylate (RCO2−) ligands. Reflecting the diversity of carboxylic acids, the inventory of metal carboxylates is large. Many are useful commercially, and many have attracted ...

s. These ethylhexanoate complexes are used in organic and industrial chemical synthesis. They function as

catalyst Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...

s in

polymer A polymer (; Greek '' poly-'', "many" + ''-mer'', "part") is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic a ...

izations as well as for

oxidation Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a d ...

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 an ...

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 consists 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 complexing agents. Many m ...

. Their structures are akin to the corresponding

acetate An acetate is a salt (chemistry), salt formed by the combination of acetic acid with a base (e.g. Alkali metal, alkaline, Alkaline earth metal, earthy, Transition metal, metallic, nonmetallic or radical Radical (chemistry), base). "Acetate" als ...

Examples of metal ethylhexanoates

* Hydroxyl aluminium bis(2-ethylhexanoate), used as a thickener *

Tin(II) ethylhexanoate Tin(II) 2-ethylhexanoate or tin(II) octoate or stannous octoate (Sn(Oct)2) is a compound of tin. Produced by the reaction of tin(II) oxide and 2-ethylhexanoic acid, it is a clear colorless liquid at room temperature, though often appears yellow due ...

(CAS# 301-10-0), a catalyst for

polylactide Polylactic acid, also known as poly(lactic acid) or polylactide (PLA), is a thermoplastic polyester with backbone formula or , formally obtained by condensation of lactic acid with loss of water (hence its name). It can also be prepared by rin ...

and

poly(lactic-co-glycolic acid) PLGA, PLG, or poly(lactic-''co''-glycolic acid) is a copolymer which is used in a host of Food and Drug Administration (FDA) approved therapeutic devices, owing to its biodegradability and biocompatibility. PLGA is synthesized by means of ring-op ...

. * Cobalt(II) ethylhexanoate (CAS# 136-52-7), a drier for alkyd resins * Nickel(II) ethylhexanoate (CAS# 4454-16-4)

References

{{DEFAULTSORT:Ethylhexanoic acid, 2- Alkanoic acids

Production

Metal ethylhexanoates

Examples of metal ethylhexanoates

See also

References