Alkanes reinvented

11 May 2013 - Green chemistry

Nonane synthesis Sutton 2013  The gradual replacement of fossil fuels by biofuels requires the reinvention of many chemicals that now also rely on fossil fuel feedstock. Sutton et al. point out that the conversion of highly functionalised biomaterials to typically non-functionalized hydrocarbons requires special chemistry. They report the synthesis of nonane from hydroxymethylfurfural and acetone as a proof of concept (DOI).

Step 1 is a chain extension and an aldol reaction, step 2 is a one-pot reaction and a combination of hydrogenation and deoxygenation. Challenge encountered: the furan ring has open before furan hydogenation because that leads to a further non-reactive product.