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 + O2 + 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): 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==