Self-metathesis of methyl oleate on silica-supported Hoveyda–Grubbs catalysts

• Methyl oleate metathesis is efficiently promoted on Hoveyda–Grubbs (HG)/SiO2 catalysts.
• The HG leaching is negligible during the progress of the reaction in cyclohexane.
• 9-Octadecene-1,18-dioate and 9-octadene equilibrium yields are rapidly reached on HG/SiO2.
• The carbon-efficiency is practically 100% since no byproducts are formed.

The self-metathesis of methyl oleate (MO) to yield 9-octadecene and 9-octadecene-1,18-dioate (9-OD) was studied in liquid-phase on silica-supported Hoveyda–Grubbs complex catalysts (HG/SiO2) containing 0.43–6.0 wt.% HG. The reaction was carried out in a batch reactor at 303–343 K and 101.3 kPa, using cyclohexane as solvent. HG/SiO2 catalysts were active and highly selective for the MO metathesis reaction; equilibrium values of MO conversion and 9-OD yield were reached in 80 min. No catalyst leaching took place in cyclohexane. Catalysts containing HG > 0.87 wt.% showed no significant deactivation after two consecutive catalytic tests.

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