Acrylates via Metathesis of Crotonates

Article abstract of DOI:10.1021/op5003006

Crotonic acid has the potential to be produced from renewable resources at low cost but currently has a limited market. We are investigating catalytic routes to exploit the functionalities of crotonic acid to produce a range of established industrial chemicals. Here we report our work on converting crotonates to acrylates, where a cost-competitive bio-based alternative can provide a market advantage. Our optimized reaction conditions for the cross-metathesis between crotonates and ethylene resulted in an increase in catalyst turnover numbers by 2 orders of magnitude compared with literature values. Control experiments showed the cross-metathesis with ethylene to be an equilibrium reaction. The turnover-number-limiting factor was found to be the stability of the metathesis catalyst.