Simultaneous production of biobased styrene and acrylates using ethenolysisElectronic supplementary information (ESI) available. See DOI: 10.1039/c2gc35498e

Phenylalanine ( 1 ), which could be potentially obtained from biofuel waste streams, is a precursor of cinnamic acid ( 2 ) that can be converted into two bulk chemicals, styrene ( 3 ) and acrylic acid ( 4 ), via an atom efficient pathway. With 5 mol% of Hoveyda-Grubbs 2nd generation catalyst, 1 bar of ethylene, and using dichloromethane as solvent, cinnamic acid ( 2 ) can be converted to acrylic acid and styrene at 40 °C in 24 h with 13% conversion and 100% selectivity. Similar results are obtained using cinnamic acid esters (methyl, ethyl and n -butyl) as substrates and optimisation leads to higher conversions (up to 38%). For the first time, cross-metathesis of these types of electron deficient substrates was achieved. Electron poor cinnamates, accessible from phenylalanine, were successfully converted into bulk chemicals using metathesis as a key step.