2-Ethylhexanol
2-Ethylhexanol 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 large scale for use in numerous applications such as solvents, flavors, and fragrances and especially as a precursor for production of other chemicals such as emollients and plasticizers. It is encountered in plants, fruits, and wines. The odor has been reported as "heavy, earthy, and slightly floral" for the R enantiomer and "a light, sweet floral fragrance" for the S enantiomer.
Properties and applications
The branching in 2-ethylhexanol inhibits crystallization. Esters of 2-ethylhexanol are similarly affected, which together with low volatility, is the basis of applications in the production of plasticizers and lubricants, where its presence helps reduce viscosity and lower freezing points. Because 2-ethylhexanol is a fatty alcohol, its esters have emollient properties. Representative is the diester bis phthalate, commonly used in PVC. The triester tris trimellitate is another common plasticizer produced via the esterification of three 2-ethylhexanol per trimellitic acid.It is also commonly used as a low volatility solvent. The nitrate ester of 2-Ethylhexanol is also used as a cetane improver for diesel fuel. It also used to react with epichlorohydrin and sodium hydroxide to produce 2-Ethylhexyl glycidyl ether which is then used as an epoxy reactive diluent in various coatings, adhesives and sealants applications. It can be used in the development of photos, production of rubber and extraction of oil and gas.
Industrial production
2-Ethylhexanol is produced industrially by the hydrogenation 2-ethylhexanal. About 2,500,000 tons are prepared in this way annually.Health effects
2-Ethylhexanol exhibits low toxicity in animal models, with LD50 ranging from 2-3 g/kg. 2-Ethylhexanol has been identified as a cause of indoor air quality related health problems, such as respiratory system irritation, as a volatile organic compound. 2-Ethylhexanol is emitted to air from a PVC flooring installed on concrete that had not been dried properly.2-Ethylhexanol has been linked to developmental toxicity. This is thought to be a result of metabolism of 2-ethylhexanol into 2-ethylhexanoic acid via oxidation of the primary alcohol. The teratogenicity of 2-ethylhexanoic acid, as well as similar substances such as valproic acid, has been well established.