2-ETHYLHEXANOIC ACID

2-Ethylhexanoic acid is a branched-chain fatty acid.
2-Ethylhexanoic acid is a colorless to light yellow liquid with a mild odor. 
2-Ethylhexanoic acid will burn though 2-Ethylhexanoic acid may take some effort to ignite. 

CAS:    149-57-5
MF:    C8H16O2
MW:    144.21
EINECS:    205-743-6

Synonyms:
2-BUTYLBUTANOIC ACID;(+/-)-2-ETHYLHEXANOIC ACID;2-ETHYLHEXOIC ACID;ALPHA-ETHYLCAPROIC ACID;A-ETHYLCAPROIC ACID;BUTYLETHYLACETIC ACID;CARBOXYLIC ACID C8;ETHYLBUTYLACETIC ACID

2-Ethylhexanoic acid is slightly soluble in water. 2-Ethylhexanoic acid is corrosive to metals and tissue. 
2-Ethylhexanoic acid is used to make paint dryers and plasticizers.
2-Ethylhexanoic acid (2-EHA), commonly known as octoic acid, is the organic compound with the formula CH3(CH2)3CH(C2H5)CO2H. 
2-Ethylhexanoic acid 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. 
2-Ethylhexanoic acid is supplied as a racemic mixture. 
Esters and salts of 2-EHA are called 2-ethylhexanoates, e.g. potassium 2-ethylhexanoate.
2-Ethylhexanoic acid, with the CAS number 149-57-5, is a branched-chain fatty acid characterized by its eight carbon atoms and a carboxylic acid functional group. 

2-Ethylhexanoic acid is a colorless to pale yellow liquid with a characteristic odor and is soluble in organic solvents but only slightly soluble in water. 
The molecular formula is C8H16O2, and it has a molecular weight of approximately 144.21 g/mol. 
2-Ethylhexanoic acid is known for its use as a chemical intermediate in the production of various esters, surfactants, and as a stabilizer in the manufacture of plastics and lubricants. Additionally, 2-ethylhexanoic acid is utilized in the formulation of certain paints and coatings due to its ability to enhance the solubility of metal salts. 
2-Ethylhexanoic acid exhibits moderate toxicity and should be handled with care, as it can cause skin and eye irritation. 
Overall, 2-ethylhexanoic acid is an important industrial chemical with diverse applications across multiple sectors.

2-Ethylhexanoic acid Chemical Properties
Melting point: -59 °C
Boiling point: 228 °C(lit.)
density: 0.906
vapor density: 4.98 (vs air)
vapor pressure: <0.01 mm Hg ( 20 °C)
refractive index: n20/D 1.425(lit.)
Fp: 230 °F
storage temp.: Store below +30°C.
solubility: 1.4g/l
form: Liquid
pka: pK1:4.895 (25°C)
color: Clear
PH: 3 (1.4g/l, H2O, 20℃)
Odor: Mild odour
PH Range: 3 at 1.4 g/l at 20 °C
biological source: synthetic
explosive limit: 1.04%, 135°F
Water Solubility: 2 g/L (20 ºC)
BRN: 1750468
Henry's Law Constant: 3.5×100 mol/(m3Pa) at 25℃, HSDB (2015)
Exposure limits    ACGIH: TWA 5 mg/m3
Stability: Stable. Combustible. Incompatible with strong oxidizing agents, reducing agents, bases.
InChI: 1S/C8H16O2/c1-3-5-6-7(4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)
LogP: 2.7 at 25℃
CAS DataBase Reference: 149-57-5(CAS DataBase Reference)
NIST Chemistry Reference: Hexanoic acid, 2-ethyl-(149-57-5)
EPA Substance Registry System: 2-Ethylhexanoic acid (149-57-5)

Uses    
2-Ethylhexanoic acid is used in the preparation of metal derivatives, which act as a catalyst in polymerization reactions. 
For example, tin 2-Ethylhexanoic acid is used in the manufacturing of poly(lactic-co-glycolic acid). 
2-Ethylhexanoic acid is also used as a stabilizer for polyvinyl chlorides. 
2-Ethylhexanoic acid is also involved in solvent extraction and dye granulation. 
Further, 2-Ethylhexanoic acid is used to prepare plasticizers, lubricants, detergents, flotation aids, corrosion inhibitors and alkyd resins. 
In addition to this, 2-Ethylhexanoic acid serves as a catalyst for polyurethane foaming.
Ethylhexoates of light metals are used to convert some mineral oils to greases. 
Its esters are used as plasticizers.

2-Ethylhexanoic acid can be used:
As a reactant in esterification , decarboxylative alkynylation , and preparation of alkyl coumarins via decarboxylative coupling reactions.
In the organocatalytic medium for the preparation of various 3,4-dihydropyrimidin-2(1H)-ones/thiones by Biginelli reaction.

Reactivity Profile    
2-Ethylhexanoic acid is a carboxylic acid. 
Carboxylic acids donate hydrogen ions if a base is present to accept them. 
They react in this way with all bases, both organic (for example, the amines) and inorganic. 
Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. 
Neutralization between an acid and a base produces water plus a salt. 
Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. 
Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. 
The pH of solutions of carboxylic acids is therefore less than 7.0. 
Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt.
Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. 

Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. 
Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in 2-Ethylhexanoic acid to corrode or dissolve iron, steel, and aluminum parts and containers. 
Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. 
The reaction is slower for dry, solid carboxylic acids. 
Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. 
Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. 

Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. 
Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. 
Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. 
These reactions generate heat. 
A wide variety of products is possible. 
Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.

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
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.