2-Butoxyethanol
2-Butoxyethanol is a colorless, high-boiling liquid organic compound with the molecular formula C₆H₁₄O₂ and a mild ether-like odor, classified as a glycol ether that functions as a primary alcohol where one methyl hydrogen of ethanol is substituted by a butoxy group.[1][2] Its physical properties include a boiling point of 171 °C, a melting point of -70 °C, and miscibility with water and many organic solvents, enabling its role in dissolving both hydrophilic and hydrophobic substances.[3] Industrially produced via the reaction of ethylene oxide with n-butanol, it serves primarily as a versatile solvent in applications such as water-based paints, varnishes, household cleaners, inks, and cosmetics, where it enhances product stability and efficacy by coupling water solubility with oil-dissolving power.[4][5][6] However, empirical data from toxicological studies indicate moderate acute toxicity, with inhalation or dermal exposure at high levels causing hemolysis, reduced hemoglobin, irritation to eyes and respiratory tract, and potential liver and kidney damage, though it lacks evidence of carcinogenicity or mutagenicity in humans.[7][6] Regulatory bodies have established exposure limits, such as OSHA's permissible exposure level of 50 ppm, to mitigate occupational risks while preserving its industrial utility.[2][7]
History
Discovery and Early Development
2-Butoxyethanol emerged from early 20th-century advancements in glycol ether synthesis, pioneered by Carbide and Carbon Chemicals Corporation (predecessor to Union Carbide) as part of efforts to develop superior industrial solvents. The compound, synthesized via the reaction of ethylene oxide with n-butanol, followed the 1920s patenting of analogous ethyl cellosolve by Dr. Charles O. Young, which established the foundational process for monoalkyl ether derivatives of ethylene glycol. These developments addressed limitations of conventional alcohols, providing a solvent with enhanced solvency for resins, oils, and nitrocellulose in lacquers and coatings. Commercialization accelerated in the 1930s and 1940s as demand grew for versatile, high-boiling-point solvents in paints, inks, and cleaning formulations, where 2-butoxyethanol demonstrated superior coupling and penetration properties over ethanol or methanol derivatives. By the mid-20th century, industrial production had scaled, reflecting its integration into expanding manufacturing sectors. U.S. output reached 130 million pounds annually by 1972, underscoring its role in broadening solvent applications beyond traditional options.[5] This growth paralleled the petrochemical boom, with 2-butoxyethanol becoming a key E-series glycol ether by the 1950s.[8]Properties
Physical Characteristics
2-Butoxyethanol is a colorless liquid with a mild, ether-like odor.[9] Its molecular formula is C₆H₁₄O₂.[1] The compound has a boiling point of 171 °C at standard pressure.[1] Its density is 0.90 g/cm³ at 20 °C, making it less dense than water.[1] The vapor pressure is approximately 0.8 mmHg at 20 °C, which corresponds to moderate volatility suitable for solvent applications.[1] 2-Butoxyethanol is fully miscible with water and most organic solvents due to its amphiphilic structure featuring both hydrophobic butyl and hydrophilic ethoxyhydroxy groups.[1]| Physical Property | Value | Reference Conditions |
|---|---|---|
| Melting Point | -75 °C | Literature value |
| Flash Point | 67 °C | Closed cup |