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]]