Bleaching Earths as Powerful Additives for Ru-Catalyzed Self-Metathesis of Non-Refined Methyl Oleate at Pilot Scale

Jessica Allard (1) , Idriss Curbet (1) , Guillaume Chollet (2) , Fabien Tripoteau (1) , Sophie Sambou , Frédéric Caijo (3) , Yann Raoul (4) , Christophe Crevisy (1) , Olivier Baslé (1) , Marc Mauduit (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 ITERG - Institut des corps gras
3 CPM - Chimie et Photonique Moléculaires
4 ONIDOL - Organisation Nationale Interprofessionnelle des Graines et Fruits Oléagineux

A practical and cost-effective ruthenium-catalyzed self-metathesis of non-refined methyl oleate (85%) derived from very high oleic sunflower oils was demonstrated at pilot scale using a robust and kg-scale commercially available SIPr-M71 pre-catalyst. The simple addition of 1 wt% bleaching earths (Tonsil 110FF) to a thermally pretreated oil could efficiently prevent catalyst deactivation. Remarkably, without the need for filtration, the catalytic system was able to achieve a turnover number (TON) of more than 744 000 at a catalyst loading of only 1 ppm. At large scale (up to 200 kg), the equilibrium of the self-metathesis reaction was reached within 1 hour at 50 degrees C under neat conditions at a very low 5 ppm catalyst loading to produce the expected primary metathesis products (PMP), that is, 9-octadecene and dimethyl-9-octadecenoate, with a productive TON of 94900.

Keywords: bleaching earths; olefin metathesis; oleochemicals; pilot production; ruthenium

Domains: Chemical Sciences

Jessica Allard, Idriss Curbet, Guillaume Chollet, Fabien Tripoteau, Sophie Sambou, et al.. Bleaching Earths as Powerful Additives for Ru-Catalyzed Self-Metathesis of Non-Refined Methyl Oleate at Pilot Scale. Chemistry - A European Journal, 2017, 23 (52), pp.12729-12734. ⟨10.1002/chem.201703049⟩. ⟨hal-01614771⟩