Acetone → Furoin

Participants

Reaction Steps

This has as a consequence that if stoichiometric ratios are used, which means 2 moles of furfural and 1 mole of acetone (since acetone can react by both ends), between 16% and 37% of components with only 5 carbon atoms would be obtained, having a very limited interest as components for gasoline (Appl. Catal. B Environ. 2006, 66, 111-118). A second product with 8 carbon atoms which tends to be one-third of the mixture appears under other conditions. This condensation product is hydrogenated to n-octane which does not have an interesting application in gasoline since it has linear chain, nor in diesel because of the low molecular weight. To increase selectivity to 85% with a 71% yield, the condensation has to be carried out in an aqueous phase and hydrogenation in hexadecane as a solvent at 120° C. thereby making the process more expensive (Appl. Catal. B Environ. 2006, 66, 111-118). The authors themselves realized the disadvantages caused by selectivity and proposed as an alternative the hydrogenation of the furan ring to tetrahydrofuran since these derivatives are capable of carrying out an aldol condensation with themselves and this would ensure a high selectivity. However, chemoselective hydrogenation of, for example, furfural to tetrahydrofurfural in one step is still a challenge and it is currently carried out in several stages. In any case, if a multistage process is accepted, molecules with a total of 10 carbon atoms can be obtained (Science 2005, 308, 1446-1450) as well as by the formation of furoin.

Provenance & Evidence