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The catalysed synthesis of symmetrical ketones from alcohols

2001; Elsevier BV; Volume: 165; Issue: 1-2 Linguagem: Inglês

10.1016/s1381-1169(00)00445-3

1873-314X

Neville Plint, Neil J. Coville, D Lack, Gillian L. Nattrass, T Vallay,

Oxidative Organic Chemistry Reactions

Reaction of a series of primary and secondary alcohols (1-propanol, 2-propanol, 1-butanol, 2-methyl-1-propanol, 1-pentanol, 1-hexanol and 1-heptanol) with O2 over CeO2/MgO (1 atm, 450°C) produced the symmetrical ketone with 2n−1 carbon atoms in 5–45% yield. The ketones were characterised by a combination of GC-MS and 1H NMR spectroscopy. Aldehydes and aldol condensation products were the main products produced in competing reactions. No ketone was produced from the reaction of 2-methyl-2-propanol with oxygen. Reaction of a 1:1 mixture of 1-hexanol and 1-heptanol over the CeO2/MgO catalyst produced a statistical yield of the three expected ketones. The data are consistent with oxidation of the alcohol to the acid followed by coupling of two acid molecules to give the symmetrical ketone.