Furfural → Furoin

Participants

Reaction Steps

This has as a consequence that if we use stoichiometric ratios, which means 2 moles of furfural and 1 mol of acetone (since the acetone can react at both ends), between 16 and 37% of components with only 5 carbon atoms would be obtained that have a very limited interest as components for gasoline (App. Catal. B Environ. 2006, 66, 111-118). A second product with 8 carbon atoms which is usually one third of the mix appears in other conditions. This condensation product is hydrogenated to n-octane that does not have an interesting application in gasoline for having linear chain, or in diesel for the low molecular weight. To increase the selectivity to 85% with a yield of 71% the condensation has to be carried out in an aqueous phase, and the hydrogenation in hexadecane as a solvent at 120° C. which is a more expensive method (Appl. Catal. B Environ. 2006, 66, 111-118). The own authors realized the drawbacks caused by the selectivity and proposed as an alternative the hydrogenation of the furane ring to tetrahydrofurane since these derivatives are able to carry out an aldol condensation with themselves which would ensure a high selectivity. However, chemoselective hydrogenation of, e.g., furfural to tetrahydrofurfural in one step is still a challenge and is currently carried out in several stages. In any case, if a multi-stage method is accepted, molecules with a total of 10 carbon atoms can be obtained (Science 2005, 308, 1446-1450) the same as by furoin formation.

Provenance & Evidence