1-Hexanol
542968
223134948
2008-07-02T18:51:58Z
129.100.60.28
{{Chembox new
| Name = 1-Hexanol
| ImageFile = Hexan-1-ol-2D-skeletal.png
| ImageSize = 200px
| ImageName = Hexan-1-ol
| ImageFile1 = Hexan-1-ol-3D-vdW.png
| ImageSize1 = 200px
| ImageName1 = Hexan-1-ol, caproic alcohol
| IUPACName = Hexan-1-ol
| Section1 = {{Chembox Identifiers
| CASNo = 111-27-3
| SMILES = CCCCCCO
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>6</sub>H<sub>14</sub>O
| MolarMass = 102.17 g/mol
| Density = 0.8136 g/cm³
| MeltingPt = -52 °C
| BoilingPt = 151.8 °C
}}
| Section7 = {{Chembox Hazards
| FlashPt = 63 °C
}}
}}
'''1-Hexanol''' is an organic [[alcohol]] with a six [[carbon]] chain and a condensed structural formula of CH<sub>3</sub>(CH<sub>2</sub>)<sub>5</sub>OH. This colorless liquid is slightly soluble in water, but [[miscible]] with [[diethyl ether|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 C<sub>6</sub>H<sub>13</sub>OH. 1-hexanol is believed to be a component of the odour of freshly mowed grass. It is used in the [[perfume]] industry.
==Preparation==
Hexanol is produced industrially by the oligomerization of [[ethylene]] using [[triethylaluminium]] followed by oxidation of the [[organoaluminium|alkylaluminium products]].<ref name=Falbe>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</ref> An idealized synthesis is shown:
:Al(C<sub>2</sub>H<sub>5</sub>)<sub>3</sub> + 6 C<sub>2</sub>H<sub>4</sub> → Al(C<sub>6</sub>H<sub>13</sub>)<sub>3</sub>
:Al(C<sub>6</sub>H<sub>13</sub>)<sub>3</sub> + 3 O + 3 H<sub>2</sub>O → 3 HOC<sub>6</sub>H<sub>13</sub> + Al(OH)<sub>3</sub>
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 industrially to produce mixtures of isomeric C6-alcohols, which are precursors to [[plasticizer]]s.<ref name=Falbe/>
In principle, [[1-hexene]] could be converted to 1-hexanol by [[hydroboration]] ([[diborane]] in [[tetrahydrofuran]] followed by treatment with [[hydrogen peroxide]] and [[sodium hydroxide]]):
<center>[[Image:Hexene-hexanol.png|align:center]]</center>
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.
==2-Hexanol==
{{Chembox new
| Name = 2-Hexanol
| ImageFile = 2-hexanol-Line-Structure.svg
| ImageSize =
| IUPACName = Hexan-2-ol
| OtherNames =
| Section1 = {{Chembox Identifiers
| CASNo = 626-93-7
| PubChem =
| SMILES = CCCCC(C)O
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>6</sub>H<sub>14</sub>O
| MolarMass = 102.17 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPtC = 136
| Solubility =
}}
| Section7 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| Autoignition =
}}
}}
'''2-Hexanol''' (or hexan-2-ol) is a six carbon [[alcohol]] in which the [[hydroxy|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 C<sub>6</sub>H<sub>14</sub>O or C<sub>6</sub>H<sub>13</sub>OH. 2-Hexanol has a [[chiral center]] and can be resolved into [[enantiomer]]s.
==References==
<references/>
{{Alcohols}}
[[Category:flavors|Hexanol, 1-]]
[[Category:Alcohols|Hexanol, 1-]]
[[de:Hexanol]]
[[nl:1-hexanol]]
[[no:1-Heksanol]]
[[fi:Heksanoli]]
[[sv:Hexanol]]