3-Pentanol, also known as pentan-3-ol or diethylcarbinol, is a versatile aliphatic alcohol with the chemical formula C₅H₁₂O and a molecular weight of 88.15 g/mol. Classified as a secondary alcohol due to the hydroxyl (-OH) group attached to the third carbon atom of its linear pentane chain, it occupies a unique position in organic chemistry and industrial applications.
Naturally occurring in trace amounts in some plant essential oils (e.g., certain species of mint and citrus) and microbial metabolic pathways, 3-pentanol is primarily synthesized industrially through controlled chemical processes. Key manufacturing routes include the hydration of 3-pentene (a byproduct of petroleum refining or ethylene cracking) under acidic catalysis, the reduction of 3-pentanone (via hydrogenation using catalysts like nickel or palladium), and the Grignard reaction between propylmagnesium bromide and acetaldehyde—each method tailored to meet large-scale production demands or high-purity requirements for specialized uses.
Historically, 3-pentanol gained recognition in the mid-20th century as a critical intermediate in organic synthesis, with early applications focused on solvent formulations and fine chemical manufacturing. Over decades, its role has expanded as research uncovered its compatibility with diverse reaction conditions and its ability to act as both a reactant and a processing aid. Today, it is valued for its balance of hydrophobic (alkane chain) and hydrophilic (hydroxyl group) properties, making it a bridge between polar and nonpolar systems in numerous industrial and scientific contexts.
Key physical properties that define its utility include:
A colorless, transparent liquid appearance at room temperature
A mild, characteristic alcohol-like odor with subtle fruity undertones
Moderate solubility in water (≈2.8 g/100 mL at 20°C) and complete miscibility with most organic solvents (e.g., ethanol, ether, benzene, and hydrocarbons)
A boiling point of 115–117°C and a melting point of -75°C, offering stability across typical processing temperature ranges
A flash point of 33°C (closed cup), requiring standard flammable liquid handling protocols.
3-Pentanol