Butanol

Butanol (also called butyl alcohol) is a four-carbon alcohol with a formula of C4H9OH, which occurs in five isomeric structures (four structural isomers), from a straight-chain primary alcohol to a branched-chain tertiary alcohol; all are a butyl or isobutyl group linked to a hydroxyl group (sometimes represented as BuOH, n-BuOH, i-BuOH, and t-BuOH). These are n-butanol, 2 stereoisomers of sec-butanol, isobutanol and tert-butanol. Butanol is primarily used as a solvent, as an intermediate in chemical synthesis, and as a fuel. It is sometimes also called biobutanol when produced biologically and petrobutanol when produced from petroleum; those two names refer to the same substance, but highlight their different origins. Butanol (also called butyl alcohol) is a four-carbon alcohol with a formula of C4H9OH, which occurs in five isomeric structures (four structural isomers), from a straight-chain primary alcohol to a branched-chain tertiary alcohol; all are a butyl or isobutyl group linked to a hydroxyl group (sometimes represented as BuOH, n-BuOH, i-BuOH, and t-BuOH). These are n-butanol, 2 stereoisomers of sec-butanol, isobutanol and tert-butanol. Butanol is primarily used as a solvent, as an intermediate in chemical synthesis, and as a fuel. It is sometimes also called biobutanol when produced biologically and petrobutanol when produced from petroleum; those two names refer to the same substance, but highlight their different origins. The unmodified term butanol usually refers to the straight chain isomer with the alcohol functional group at the terminal carbon, which is also known as n-butanol or 1-butanol. The straight chain isomer with the alcohol at an internal carbon is sec-butanol or 2-butanol. The branched isomer with the alcohol at a terminal carbon is isobutanol or 2-methyl-1-propanol, and the branched isomer with the alcohol at the internal carbon is tert-butanol or 2-methyl-2-propanol. The butanol isomers have different melting and boiling points. n-butanol and isobutanol have limited solubility, sec-butanol has substantially greater solubility, while tert-butanol is fully miscible with water above tert-butanol's melting point. The hydroxyl group makes the molecule polar, promoting solubility in water, while the longer hydrocarbon chain mitigates the polarity and reduces solubility. The shorter chain molecules of methanol, ethanol, propanol, and tert-butanol are fully miscible with water, while n-butanol is only moderately soluble because of the diminishing polarity in the longer hydrocarbon group. Like many alcohols, butanol is considered toxic. It has shown low order of toxicity in single dose experiments to laboratory animals and is considered safe enough for use in cosmetics. Brief, repeated overexposure with the skin can result in depression of the central nervous system, as with other short-chain alcohols. Exposure may also cause severe eye irritation and moderate skin irritation. The main dangers are from prolonged exposure to the alcohol's vapors. In extreme cases this includes suppression of the central nervous system and even death. Under most circumstances, butanol is quickly metabolized to carbon dioxide. It has not been shown to damage DNA or cause cancer. Butanol is considered as a potential biofuel (butanol fuel). Butanol at 85 percent strength can be used in cars designed for gasoline (petrol) without any change to the engine (unlike 85% ethanol), and it contains more energy for a given volume than ethanol and almost as much as gasoline, and a vehicle using butanol would return fuel consumption more comparable to gasoline than ethanol. Butanol can also be added to diesel fuel to reduce soot emissions. Butanol is used as a solvent for a wide variety of chemical and textile processes, in organic synthesis, and as a chemical intermediate. It is also used as a paint thinner and a solvent in other coating applications where a relatively slow evaporating latent solvent is preferable, as with lacquers and ambient-cured enamels. It is also used as a component of hydraulic and brake fluids. A 50% solution of butanol in water has been used since the 20th century to retard the drying of fresh plaster in fresco painting. The solution is usually sprayed on the wet plaster after the plaster has been trowlled smooth and extends the working period during which frescos can be painted up to 18 hours. Butanol is used in the synthesis of 2-butoxyethanol. A major application for butanol is as a reactant with acrylic acid to produce butyl acrylate, a primary ingredient of water based acrylic paint. It is also used as a base for perfumes, but on its own has a highly alcoholic aroma.