1-Hexanol

1-Hexanol
IUPAC name	Hexan-1-ol
Other names	hexanol hexyl alcohol
Identifiers
CAS number	111-27-3
SMILES	CCCCCCO
Properties
Molecular formula	C6H14O
Molar mass	102.17 g/mol
Density	0.8136 g/cm³
Melting point	-52 °C
Boiling point	151.8 °C
Hazards
Flash point	63 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references

1-Hexanol 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 ether and ethanol. Two additional straight chain isomers of 1-hexanol exist, 2-hexanol and 3-hexanol, both of which differ by the location of the hydroxyl group. Many isomeric alcohols have the formula C₆H₁₃OH. 1-hexanol is believed to be a component of the odour of freshly mowed grass. It is used in the perfume industry.

[edit] Preparation

Hexanol is produced industrially by the oligomerization of ethylene using triethylaluminium followed by oxidation of the alkylaluminium products.^[1] An idealized synthesis is shown:

Al(C₂H₅)₃ + 6 C₂H₄ → Al(C₆H₁₃)₃

Al(C₆H₁₃)₃ + 3 O + 3 H₂O → 3 HOC₆H₁₃ + Al(OH)₃

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

[edit] Alternative methods

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

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

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.

[edit] References

1. ^ ^{a b} Jürgen Falbe, Helmut Bahrmann, Wolfgang Lipps, Dieter Mayer "Alcohols, Aliphatic" in Ullmann's Encyclopedia of Chemical Technology Wiley-VCH Verlag; Weinheim, 2002. DOI: 10.1002/14356007.a01_279