1-Hexanol
From Wikipedia, the free encyclopedia
| 1-Hexanol | |
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| IUPAC name | Hexan-1-ol |
| 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 |
151.4 °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 disclaimer and references |
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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.
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[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] 2-Hexanol
| 2-Hexanol | |
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| IUPAC name | Hexan-2-ol |
| Identifiers | |
| CAS number | [626-93-7] |
| SMILES | CCCCC(C)O |
| Properties | |
| Molecular formula | C6H14O |
| Molar mass | 102.17 g/mol |
| Boiling point |
136 °C, 409 K, 277 °F |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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2-Hexanol (or hexan-2-ol) is a six carbon alcohol in which the OH group is located on the second carbon atom. It is an isomer of 1-hexanol, 3-hexanol, 2-methylpentanol, 3-methylpentanol, 2,3-dimethylbutanol, 2-ethylbutanol and many more compounds. Its chemical formula is C6H14O or C6H13OH. 2-Hexanol has a chiral center and can be resolved into enantiomers.
[edit] References
- ^ 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
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