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Butanol
1-Butanol: skeletal structure 1-Butanol: 3D space-filling structure
General
Systematic name	1-Butanol
Other names	Butanol Butan-1-ol ''n''-Butanol ''normal''-Butanol Butyl alcohol Butyric alcohol Propylcarbinol
Molecular formula	C4H10O
SMILES	CCCCO
Molar mass	74.1216(42) g/mol
Appearance	clear liquid
CAS number	[71-36-3]
Properties
Density and phase	0.8098 g/cm³ @ 20 °C, liquid
Solubility in water	9.1 mL/100 mL H2O at 25 °C
Melting point	−89.5 °C (183.7 K)
Index of refraction	1.3993 @ 20 °C
Boiling point	117.73 °C (390.9 K)
Viscosity	3 cP at 25°C
Structure
Molecular shape	?
Coordination geometry	?
Crystal structure	?
Dipole moment	1.52 D (1-butanol)
Hazards
MSDS	External MSDS
Main hazards	flammable
NFPA 704
Flash point	37 °C (99 °F)
R/S statement	R: S:
RTECS number	EO1400000
Supplementary data page
Structure and properties	''n'', εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Related alcohols	Propanol, Pentanol, Isobutanol, 2-Butanol, tert-Butanol
Related compounds	Butyraldehyde, Butyric acid, Butylene
Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100 kPa)

'Butanol' or butyl alcohol (sometimes also called ''biobutanol'' when produced biologically), is a primary alcohol with a 4 carbon structure and the molecular formula of C₄H₁₀O. It is primarily used as a solvent, as an intermediate in chemical synthesis, and as a fuel. There are four isomeric structures for butanol.

Contents

Isomers

Uses

Production

See also

References

Isomers

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, and the branched isomer with the alcohol at the internal carbon is tert-butanol.

'''n''-butanol'	''sec''-butanol	isobutanol	''tert''-butanol

Butanol isomers, due to their different structures, have somewhat different melting and boiling points. All are moderately miscible in water, less so than ethanol, and more so than the higher (longer carbon chain) alcohols. This is because all alcohols have a hydroxyl group which makes them polar which in turn tends to promote solubility in water. At the same time the carbon chain of the alcohol resists solubility in water. Methanol, ethanol and propanol, are fully miscible in water because the hydroxyl group predominates while butanol is moderately miscible because of the balance between the two opposing solubility trends. Like many alcohols, butanol is toxic.

Uses

Butanol sees use 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 it is used as a relatively slow evaporating latent solvent in lacquers and ambient-cured enamels. It finds other uses such as a component of hydraulic and brake fluids.^[1]
It is also used as a base for perfumes, but on its own has a highly alcoholic aroma. Butanol is also considered as a potential biofuel (see Butanol fuel). Butanol at 85 percent strength can be used in cars without any change to the engine (unlike ethanol) and it produces more power than ethanol and almost as much power as gasoline.
Salts of butanol are chemical intermediates for example alkali metal salts of tert-butanol are 'tert-butoxides'.

Production

Since the 1950s, most butanol in the United States is produced commercially from fossil fuels. The most common process starts with propene, which is run through an hydroformylation reaction to form butanal, which is then reduced with hydrogen to butanol. Butanol can also be produced by fermentation of biomass by bacteria. Prior to the 1950s, Clostridium acetobutylicum was used in industrial fermentation processes producing butanol. Research in the past few decades showed results of other microorganisms that can produce butanol through fermentation.

See also

★ Solvent

★ Butanol fuel

References

★ ''Merck Index'', 12th Edition, '1575'.
1. Isobutanol at chemicalland21.com