Butanol

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Butanol (also called butyl alcohol) is a four-carbon alcohol with
a formula of C4H9OH, which occurs in five isomericstructures, from a straight-
chain primary alcohol to a branched-chain tertiary alcohol;[1] all are
a butyl or isobutyl group linked to a hydroxyl group
(sometimes represented as BuOH, n-BuOH, and i-BuOH). These are n-butanol, 2
stereoisomers of 2-butanol, tert-butanol, and isobutanol. 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.

Contents
[hide]

1Isomers

2Toxicity

3Uses

o 3.1Biobutanol

o 3.2Other uses

4Production

5See also

6References

Isomers[edit]
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.
n-butanol sec-butanol isobutanol tert-butanol

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.

Toxicity[edit]
Like many alcohols, butanol is considered toxic. It has shown low order of toxicity in
single dose experiments to laboratory animals.[2][3] 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 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 damage DNA or
cause cancer.

Uses[edit]
Biobutanol[edit]
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 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.[4]
Other uses[edit]
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.[5]
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.[6]
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[edit]
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 (propylene), which
is put through a hydroformylation reaction to form butyraldehyde, which is then
reduced with hydrogen to 1-butanol and/or 2-butanol. Tert-butanol is derived
from isobutane as a co-product of propylene oxide production. Butanol can also be
produced by fermentation of biomass by bacteria. Prior to the 1950s, Clostridium
acetobutylicum was used in industrial fermentation to produce butanol. Research in
the past few decades showed results of other microorganisms that can produce
butanol through fermentation.

See also[edit]
A.B.E. process

Algal fuel

Butanol fuel

Solvent

References[edit]
Merck Index, 12th Edition, 1575.

1. Jump up^ Atsumi, S.; Hanai, T.; Liao, J. C. (2008). "Non-

fermentative pathways for synthesis of branched-chain
higher alcohols as biofuels". Nature. 451 (7174): 86
9. doi:10.1038/nature06450. PMID 18172501.

2. Jump up^ 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.

3. Jump up^ n-Butanol

4. Jump up^ Antoni, D; Zverlov, V. & Schwarz, W H. (2007).

"Biofuels from Microbes". Applied Microbiology and
Biotechnology. 77: 2335. doi:10.1007/s00253-007-1163-x.

5. Jump up^ Isobutanol at chemicalland21.com

6. Jump up^ Harris O.; et al. (August 1998). Toxicological

Profile for 2-Butoxyethanol and 2-butoxyethanol acetate.
U.S. Dept of Health and Human Services.

[hide]
v
 t
e
Alcohols

raight-chain Methanol (C
primary 1)

alcohols (1) Ethanol (C

2)

1-Propanol (C
3)

n-Butanol (C
4)

1-Pentanol (C
5)

1-Hexanol (C
6)

1-Heptanol (C
7)

1-Octanol (C
8)

1-Nonanol (C
9)

1-Decanol (C
10)

Undecanol (C
11)

Dodecanol (C
12)

Tridecan-1-ol (C
13)

1-Tetradecanol (C
14)

Pentadecan-1-ol (C
15)

Cetyl alcohol (C
16)

Heptadecan-1-ol (C
17)
 Stearyl alcohol (C
18)

Nonadecan-1-ol (C
19)

Arachidyl alcohol (C
20)

Heneicosan-1-ol (C
21)

Docosanol (C
22)

Tricosan-1-ol (C
23)

1-Tetracosanol (C
24)

Pentacosan-1-ol (C
25)

1-Hexacosanol (C
26)

1-Heptacosanol (C
27)

1-Octacosanol (C
28)

1-Nonacosanol (C
29)

Triacontanol (C
30)

Isobutanol (C
4)

Isoamyl alcohol (C
5)

her primary 2-Methyl-1-butanol (C

alcohols 5)

Phenethyl alcohol (C
8)

Tryptophol (C
10)

Secondary Isopropanol (C
 3)

2-Butanol (C
4)

2-Pentanol (C
5)

alcohols (2) 2-Hexanol (C

6)

2-Heptanol (C
7)

Cyclohexanol (C
6)

tert-Butyl alcohol (C
4)

tert-Amyl alcohol (C
5)

2-Methyl-2-pentanol (C
6)

Tertiary 2-Methylhexan-2-ol (C
alcohols (3) 7)

2-Methylheptan-2-ol(C
8)

3-Methyl-3-pentanol (C
6)

3-Methyloctan-3-ol (C
9)
Categories:
Alkanols
Alcohol solvents
Fatty alcohols
Biotechnology products
Liquid fuels
Oxygenates
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