1-Hexanol

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Hexyl alcohol

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Template:Longitem	969167
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MeSH	1-Hexanol
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UN number	2282
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Appearance	colorless liquid
Density	0.82 g cm−3 (at 20 °C)
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log P	1.858
Vapor pressure	100 Pa (at 25.6 °C)
Template:Longitem	1.4178 (at 20 °C)
Template:Longitem	243.2 J K−1 mol−1
Template:Longitem	287.4 J K−1 mol−1
Template:Longitem	−377.5 kJ mol−1
Template:Longitem	−3.98437 MJ mol−1
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1-Hexanol (IUPAC name hexan-1-ol) is an organic alcohol with a six-carbon chain and a condensed structural formula of CH₃(CH₂)₅OH. This colorless liquid is slightly soluble in water, but miscible with diethyl ether and ethanol. Two additional straight chain isomers of 1-hexanol, 2-hexanol and 3-hexanol, exist, both of which differing by the location of the hydroxyl group. Many isomeric alcohols have the formula C₆H₁₃OH. It is used in the perfume industry.

Preparation

Hexanol is produced industrially by the oligomerization of ethylene using triethylaluminium followed by oxidation of the alkylaluminium products. An idealized synthesis is shown:

Al(C₂H₅)₃ + 6C₂H₄ → Al(C₆H₁₃)₃

Al(C₆H₁₃)₃ + 1+1⁄2O₂ + 3H₂O → 3HOC₆H₁₃ + Al(OH)₃

The process generates a range of oligomers that are separated by distillation.

Alternative methods

Another method of preparation entails hydroformylation of 1-pentene followed by hydrogenation of the resulting aldehydes. This method is practiced in industry to produce mixtures of isomeric C₆-alcohols, which are precursors to plasticizers.

In principle, 1-hexene could be converted to 1-hexanol by hydroboration (diborane in tetrahydrofuran followed by treatment with hydrogen peroxide and sodium hydroxide):

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File:Hexan-1-ol.jpg

Hexan-1-ol

This method is instructive and useful in laboratory synthesis but of no practical relevance because of the commercial availability of inexpensive 1-hexanol from ethylene.

Occurrence in nature

1-Hexanol is believed to be a component of the odour of freshly mown grass. Alarm pheromones emitted by the Koschevnikov gland of honey bees contain 1-hexanol. It also is partly responsible for the fragrance of strawberries.

See also

• Cis-3-Hexenal, another volatile organic compound, is also considered responsible for the freshly mowed grass odor.

External links

• International Chemical Safety Card 1084