Butanol

Butanol
IUPAC name	1-Butanol
Other names	Butanol Butan-1-ol n-Butanol normal-Butanol Butyl alcohol Butyric alcohol Propylcarbinol
Identifiers
CAS number	[71-36-3]
RTECS number	EO1400000
SMILES	CCCCO
Properties
Molecular formula	C4H10O, BuOH
Molar mass	74.1216(42) g/mol
Appearance	clear liquid
Density	0.8098 g/cm³ @ 20 °C, liquid
Melting point	−89.5 °C (183.7 K)
Boiling point	117.73 °C (390.9 K)
Solubility in water	9.1 mL/100 mL H2O at 25 °C
Viscosity	3 cP at 25°C
Structure
Dipole moment	1.52 D (1-butanol)
Hazards
MSDS	External MSDS
Main hazards	flammable
NFPA 704	3 1 0
R-phrases	R10 R22 R37/38 R41 R67
S-phrases	S7/9 S13 S26 S37/39 S46
Flash point	37 °C (99 °F)
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) Infobox disclaimer and references

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 belongs to the higher alcohols and branched-chain alcohols. http://www.nature.com/nature/journal/v451/n7174/abs/nature06450.html

It is primarily used as a solvent, as an intermediate in chemical synthesis, and as a fuel.

There are four isomeric structures for butanol.

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; 2-methyl-1-propanol, and the branched isomer with the alcohol at the internal carbon is tert-butanol; 2-methyl-2-propanol.

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.

Toxicity

Like many alcohols, butanol is considered toxic. It has shown low order of toxicity in single dose experiments to laboratory animals. 16 ECETOC JACC No. 41 n-Butanol (CAS No. 71-36-3), European Centre for Ecotoxicology and Toxicology of Chemicals, Brussels, December 2003, pages 3-4. http://www.dow.com/productsafety/finder/nbut.htm#HealthInfo and is considered safe enough for use in cosmedics. Brief, repeated overexposure with the skin can result in depression of the central nervous system, similar to other short-chain alcohols. Exposure may cause severe eye irritation and moderate skin irritation. The main dangers are from prolonged exposure to fumes. 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 cause genotoxicity (causes damage to the DNA or cancer).

Uses

Biobutanol

Main article: Butanol fuel

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 produces more power than ethanol and almost as much power as gasoline, so the miles per gallon will also almost match that of gasoline.

Other 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.Isobutanol at chemicalland21.com

It is also used as a base for perfumes, but on its own has a highly alcoholic aroma.

Salts of butanol are chemical intermediates for example alkali metal salts of tert-butanol are tert-butoxides.

Production

Main article: Butanol fuel

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

• A.B.E. process
• Algal fuel
• Butanol fuel
• Solvent

References

• Merck Index, 12th Edition, 1575.

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