Ru complexes of Hoveyda-Grubbs type immobilized on lamellar zeolites: activity in olefin metathesis reactions.

Ru complexes of Hoveyda-Grubbs type immobilized on lamellar zeolites: activity in olefin metathesis reactions.

Beilstein journal of organic chemistry (2015-12-15)

Hynek Balcar, Naděžda Žilková, Martin Kubů, Michal Mazur, Zdeněk Bastl, Jiří Čejka

RESUMEN

Hoveyda-Grubbs type catalysts with cationic tags on NHC ligands were linker-free immobilized on the surface of lamellar zeolitic supports (MCM-22, MCM-56, MCM-36) and on mesoporous molecular sieves SBA-15. The activity of prepared hybrid catalysts was tested in olefin metathesis reactions: the activity in ring-closing metathesis of citronellene and N,N-diallyltrifluoroacetamide decreased in the order of support MCM-22 ≈ MCM-56 > SBA-15 > MCM-36; the hybrid catalyst based on SBA-15 was found the most active in self-metathesis of methyl oleate. All catalysts were reusable and exhibited low Ru leaching (<1% of Ru content). XPS analysis revealed that during immobilization ion exchange between Hoveyda-Grubbs type catalyst and zeolitic support occurred in the case of Cl(-) counter anion; in contrast, PF6 (-) counter anion underwent partial decomposition.

MATERIALES

Referencia del producto

Marca

Descripción del producto

D65100

Sigma-Aldrich

Diclorometano, contains 40-150 ppm amylene as stabilizer, ACS reagent, ≥99.5%

179418

Sigma-Aldrich

Tolueno, ACS reagent, ≥99.5%

199443

Sigma-Aldrich

Óxido de alúmina, Brockmann I, standard grade, activated, basic

199974

Sigma-Aldrich

Óxido de alúmina, activated, Brockmann I, standard grade, neutral

32249

Sigma-Aldrich

Tolueno, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥99.7% (GC)

32222

Sigma-Aldrich

Diclorometano, puriss. p.a., ACS reagent, reag. ISO, ≥99.9% (GC)

320269

Sigma-Aldrich

Diclorometano, ACS reagent, ≥99.5%, contains 40-150 ppm amylene as stabilizer

S5376

Sigma-Aldrich

Methyl stearate, ~99% (GC)

229423

Sigma-Aldrich

Óxido de alúmina, powder, 99.99% trace metals basis

199966

Sigma-Aldrich

Óxido de alúmina, Brockmann I, standard grade, activated, acidic

P5177

Sigma-Aldrich

Methyl palmitate, ≥99% (capillary GC)

265497

Sigma-Aldrich

Óxido de alúmina, powder, primarily α phase, ≤10 μm avg. part. size, 99.5% trace metals basis

544833

Sigma-Aldrich

Óxido de alúmina, nanopowder, <50 nm particle size (TEM)

24233

Sigma-Aldrich

Diclorometano, puriss., meets analytical specification of Ph. Eur., NF, ≥99% (GC)

320552

Sigma-Aldrich

Tolueno, ACS reagent, ≥99.5%

702129

Sigma-Aldrich

Aluminum oxide, nanoparticles, <50 nm particle size (DLS), 20 wt. % in isopropanol

676853

Sigma-Aldrich

Diclorometano, ACS reagent, ≥99.5%, contains 40-150 ppm amylene as stabilizer

270997

Sigma-Aldrich

Diclorometano, anhydrous, ≥99.8%, contains 40-150 ppm amylene as stabilizer

179965

Sigma-Aldrich

Tolueno, Laboratory Reagent, ≥99.3%

244511

Sigma-Aldrich

Tolueno, anhydrous, 99.8%

234745

Sigma-Aldrich

Óxido de alúmina, Corundum, α-phase, -100 mesh

414069

Sigma-Aldrich

Óxido de alúmina, pellets, 3 mm

342688

Sigma-Aldrich

Óxido de alúmina, fused, powder, primarily α-phase, -325 mesh

718475

Sigma-Aldrich

Óxido de alúmina, nanopowder, 13 nm primary particle size (TEM), 99.8% trace metals basis

202606

Sigma-Aldrich

Óxido de alúmina, 99.997% trace metals basis

W509531

Sigma-Aldrich

Methyl palmitate, ≥97%

A1522

Sigma-Aldrich

Óxido de alúmina, Type WN-6, Neutral, Activity Grade Super I

267740

Sigma-Aldrich

Óxido de alúmina, pore size 58 Å, ~150 mesh

494453

Sigma-Aldrich

Diclorometano, biotech. grade, 99.9%, contains 40-150 ppm amylene as stabilizer

642991

Sigma-Aldrich

Aluminum oxide, nanoparticles, 30-60 nm particle size (TEM), 20 wt. % in H₂O