2-Ethylhexanoic Alcohol (2-EH)

2-Ethylhexanoic Alcohol, or 2-Ethylhexanol (abbreviated 2-EH) is a branched, eight-carbon chiral alcohol. It is a colorless liquid produced on a massive 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.

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Description

2-Ethylhexanoic Alcohol is poorly soluble in water but soluble in most organic solvents. 2-EH is found in natural plant fragrances, and 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

Almost all 2-ethylhexanol manufactured is used as a precursor for the synthesis of the diester bis(2-ethylhexyl) phthalate (DEHP), a plasticizer. since it is a fatty alcohol, its esters tend to have emollient properties. E.g., the sunscreen octocrylene contains a 2-ethylhexyl ester for this purpose.

2-Ethylhexanoic Alcohol is also commonly used as a low volatility solvent. 2-Ethylhexanol is additionally used as an octane booster when reacted with nitric acid.

2-Ethylhexanol is industrially produced by the aldol condensation of n-butyraldehyde, followed by hydrogenation of the resulting hydroxyaldehyde. About 2,500,000 tons are prepared annually in this way.

The n-butyraldehyde is made by hydroformylation of propylene, either in a self-contained plant or as the first step in a fully integrated facility. Most facilities make n-butanol and isobutanol in addition to 2-ethylhexanol. The overall process is very similar to that of the Guerbet reaction, by which it may also be produced.