Batchwise and Continuous Organophilic Nanofiltration of Grubbs-Type Olefin Metathesis Catalysts


A mass-tagged N-mesityl imidazolinium salt with four additional -CH2NCy2 substituents was synthesized, leading to a molecular mass of nearly 1100 g mol-1 in the corresponding carbene ligand. This mass-tagged ligand was used to generate the respective Grubbs II and Grubbs-Hoveyda type complexes. The catalytic activity of the latter complex was tested in several olefin metathesis reactions and found to be slightly superior to that of the related N-mesityl based complex. In batchwise solvent resistant nanofiltration experiments the ruthenium complex dissolved in toluene and following a metathesis reactions was efficiently retained (>99.8 %) by a single nanofiltration; the permeate contained less than 4 ppm of Ru. Equally efficient catalyst retention was observed in a membrane reactor utilized for the continuous synthesis of a RCM product.
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