Separation of different metathesis Grubbs-type catalysts using organic solvent nanofiltration

Gryp, Percy van der; Barnard, Anro; Cronje, Jean-Pierre; Vlieger, Dennis de; Marx, Sanette; Vosloo, Hermanus C.M.

doi:10.1016/j.memsci.2010.02.032

Cited by 59 publications

(31 citation statements)

References 44 publications

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“…1 H-NMR (CDCl 3 , 600 MHz), 13 C-NMR (150 MHz), 31 Melting points of the pyridinyl alcoholato ligands and decomposition points of the precatalysts were determined with a Büchi B-540 melting point apparatus.…”

Section: Instrumental Methodsmentioning

confidence: 99%

“…Previously [24,31], we reported the stability (as seen in the improved catalytic lifetimes) of precatalyst 4 and other related precatalysts inter alia by using the plot of the ln([starting material]) versus time. According to Grubbs and co-workers [32], a linear plot indicates a reaction with pseudo-first order rate kinetics, while a curved plot points towards catalyst decomposition.…”

Section: Effect Of Temperature On the Catalyst Lifetimementioning

confidence: 99%

“…The first 31 The first 31 P NMR investigation of a hemilabile property of S-O ligands in Pd complexes of the type trans-[Pd(OOC-C 6 H 4 -2SR-k 1 -O)]Ph(PPh 3 ) 2 (R = i Pr, t Bu), wherein one PPh 3 ligand is replaced by a sulfur atom of the S-O ligand to afford chelates, in solution, was reported by Raubenheimer et al [10]. Grubbs-type precatalysts with hemilabile ligands showed greater lifetimes and stability [10,11].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Application of Novel Ruthenium Catalysts for High Temperature Alkene Metathesis

et al. 2017

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Four pyridinyl alcohols and the corresponding hemilabile pyridinyl alcoholato ruthenium carbene complexes of the Grubbs second generation-type RuCl(H 2 IMes)(OˆN)(=CHPh), where,1-phenyl methanolato and 1-(2 -pyridinyl)-1-(2 -methoxyphenyl),1-phenyl methanolato, are synthesized in very good yields. At high temperatures, the precatalysts showed high stability, selectivity and activity in 1-octene metathesis compared to the Grubbs first and second generation precatalysts. The 2-/4-chloro-and 4-methoxy-substituted pyridinyl alcoholato ligand-containing ruthenium precatalysts showed high performance in the 1-octene metathesis reaction in the range 80-110 • C. The hemilabile 4-methoxy-substituted pyridinyl alcoholato ligand improved the catalyst stability, activity and selectivity for 1-octene metathesis significantly at 110 • C.

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Section: Instrumental Methodsmentioning

confidence: 99%

Section: Effect Of Temperature On the Catalyst Lifetimementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and Application of Novel Ruthenium Catalysts for High Temperature Alkene Metathesis

et al. 2017

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“…An alternative process to these physico-chemical approaches would be the use of membrane separation. The nanofiltration of olefin metathesis catalysts has already been reported [27][28][29][30]. In our group, OSN has been successfully used for the recovery of a set of Grubbs-Hoveyda II prototype catalysts in dead-end filtration mode with a Starmem 228 membrane (MET-Evonik, no more commercially available); up to 5 consecutive cycles of a model reaction of ring closing metathesis (RCM) have been achieved at room temperature in toluene or dimethylcarbonate (a green solvent) with a single load of catalyst [31].…”

Section: Introductionmentioning

confidence: 99%

Comparison of two nanofiltration membrane reactors for a model reaction of olefin metathesis achieved in toluene

Rabiller-Baudry

Nasser

Renouard

et al. 2013

Separation and Purification Technology

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Comparison of two nanofiltration membrane reactors for a model reaction of olefin metathesis achieved in toluene. Separation and Purification Technology, Elsevier, 2013, 116, pp.46-60 AbstractThe recent commercialisation of nanofiltration membranes resistant toward organic solvents is a real opportunity for fine chemistry. This study deals with different ways of integration of organic solvent nanofiltration for a specific type of reactions known as olefin metathesis and shows the use of two nanofiltration membrane reactors both running in cross-flow filtration mode (0.1 m.s -1 ). They are used either in semi-continuous or continuous mode. A model ring closing metathesis reaction is chosen for the demonstration. A commercially available precatalyst, namely Grubbs-Hoveyda II, as well as a commercial polyimide membrane (Starmem 122, MWCO 220 g.mol -1 ) are used. Firstly, nanofiltration of the single pre-catalyst allows establishing that the highest retention is obtained with a 40 bar pressure. Secondly, this pressure is used with the two membrane reactors before testing other conditions. Finally, interests and limitations of the two reactors are discussed.

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“…Some examples for application of OSN to concentration and purification in industrial applications have been published previously. For instance, OSN was applied to the recovery and purification of pharmaceuticals [Cao et al, 2001;Marchetti et al, 2013;Sun et al, 2014], solvent exchange [Sheth et al, 2003], separation of base chemicals [Werhan et al, 2012;Othman et al, 2010], purification and concentration of consumer chemicals [Vanneste et al, 2011;Tsibranska and Tylkowski, 2013], concentration and purification of specialty chemicals [Tsui and Cheryan, 2007], and homogeneous catalyst recycle [Van der Gryp et al, 2010]. These studies showed the feasibility of OSN technologies in different industries at laboratory scale with flat sheet membranes or with 1.8"x12" spiral-wound membrane modules.…”

Section: Introductionmentioning

confidence: 99%

Multi-scale modelling of OSN batch concentration with spiral-wound membrane modules using OSN Designer

Shi

Peshev

Marchetti

et al. 2016

Chemical Engineering Research and Design

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Three commercial spiral-wound membrane modules of different sizes, from 1.8"x12" to 4.0"x40", are used to concentrate a solution of sucrose octaacetate in ethyl acetate under different operating conditions. A mathematical model to describe the batch concentration process is developed, based on a combination of the classical solution diffusion membrane transport model and the film theory, to account for the mass transfer effects. The model was implemented using the "OSN Designer" software tool. The membrane transport model parameters as well as all parameters in the pressure drop and mass transfer correlations for the spiral-wound modules were obtained from regression on a limited number of experimental data at steady state conditions. Excellent agreement was found between the experimental and multi-scale modelling performance data under various operating conditions. The results illustrate that the performance of a large scale batch concentration process with spiral-wound membrane modules can be predicted based on laboratory crossflow flat sheet test data when the fluid dynamics and mass transfer characteristics in the module, and the necessary channel geometry are known. In addition, the effects of concentration polarisation, pressure drop through feed and permeate channels, and thermodynamic non-ideality of the solution at large scale batch concentration are also investigated.2

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Separation of different metathesis Grubbs-type catalysts using organic solvent nanofiltration

Cited by 59 publications

References 44 publications

Synthesis and Application of Novel Ruthenium Catalysts for High Temperature Alkene Metathesis

Synthesis and Application of Novel Ruthenium Catalysts for High Temperature Alkene Metathesis

Comparison of two nanofiltration membrane reactors for a model reaction of olefin metathesis achieved in toluene

Multi-scale modelling of OSN batch concentration with spiral-wound membrane modules using OSN Designer

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