Recycling Homogeneous Catalysts Simply by Organic Solvent Nanofiltration: New Ways to Efficient Catalysis

Dreimann, Jens M.; Skiborowski, Mirko; Behr, Arno; Vorholt, Andreas J.

doi:10.1002/cctc.201601018

Cited by 42 publications

(34 citation statements)

References 29 publications

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“…The effective retention of homogeneous catalysts by nanofiltration has previously been demonstrated for different chemical systems and reactions in academia and was also successfully transferred to industry . In our particular application, the acids present in the reaction system and the consequently low pH pose special constraints for the selection of the membrane material.…”

Section: Resultsmentioning

confidence: 89%

Investigations on Catalyst Stability and Product Isolation in the Extractive Oxidative Desulfurization of Fuels Using Polyoxometalates and Molecular Oxygen

et al. 2018

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Our contribution adds important new insight to the recent finding that polyoxometalate catalysts, such as H8PV5Mo7O40 (HPA‐5), are very effective catalysts in the extractive oxidative desulfurization of fuels using molecular oxygen. Our contribution focuses on aspects of catalyst stability and deactivation caused by the accumulation of acidic products and intermediates, i. e. sulfuric acid, formic acid, acetic acid, sulfoacetic acid or 2‐sulfobenzoic acid. These compounds reduce the pH value of the aqueous catalyst phase during the course of the desulfurization reaction. At lower pH values, the higher V‐substituted species rearrange to lower V‐substituted species and VO2+. This rearrangement is responsible for a decreasing activity in extractive oxidative desulfurization. We show that formic acid, acetic acid, sulfoacetic acid and 2‐sulfobenzoic acid block active sites of the catalyst. Oxalic acid, in contrast, has been found to exert a remarkable positive effect on catalyst activity. The feasibility of catalyst recycling and efficient isolation of the decomposition products is demonstrated using four commercially available organic solvent nanofiltration membranes.

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Section: Resultsmentioning

confidence: 89%

Investigations on Catalyst Stability and Product Isolation in the Extractive Oxidative Desulfurization of Fuels Using Polyoxometalates and Molecular Oxygen

et al. 2018

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“…Vorholt's group demonstrated the use of commercially available PDMS‐based OSN membrane for recovery of homogeneous catalyst in hydroformylation reaction . Recovery of the Rh/Biphephos, Rh/Xantphos and Rh/TPP catalyst from the hydroformylation reaction of 1‐dodecene was performed continuously and the catalyst was rejected up to 95 %.…”

Section: Organic Solvent Nanofiltrationmentioning

confidence: 99%

Recent Advances Utilized in the Recycling of Homogeneous Catalysis

Shende

Saptal

Bhanage

2019

The Chemical Record

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Homogeneous catalysts often show high activity and selectivity towards the various chemical transformations. Most of the transition metal‐based active catalysts are expensive, rare, and have strict regulations for their use in pharmaceutical products. Hence, there is a requirement to develop suitable technologies for the practical separation and recycling of metal complex catalysts along with the sustainability of the process. This review focuses on the recent techniques used for the catalyst separation, their recovery, and recyclability of the homogeneous form of catalysts based on their economic compatibility and industrial applications. Various homogeneous catalysts have been reviewed on the basis of their support or media, active centres and recyclability aspects of the catalysts. This review gives brief insights into the varied examples of different recycling techniques utilized in the past 6–7 years.

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“…Following the first approach, Dreimann et al . reported on a batch process for the hydroformylation of 1‐dodecene conducted at 90 °C in toluene using a Rh‐catalyst complex combined with different ligands . Triphenylphosphine (TPP, 262 g ⋅ mol −1 ) was selected as the most promising one with respect to the constant performances obtained during the synthesis from one run to another.…”

Section: Introductionmentioning

confidence: 99%

“…Following the first approach, Dreimann et al reported on a batch process for the hydroformylation of 1-dodecene conducted at 90°C in toluene using a Rh-catalyst complex combined with different ligands. [35][36] Triphenylphosphine (TPP, 262 g · mol À 1 ) was selected as the most promising one with respect to the constant performances obtained during the synthesis from one run to another. Up to 97 % of the Rh catalyst and 66 % of the free ligand were retained by OSN at 20 bar using a commercial PDMS Membrane (oNF2, GMT Membrantechnik GmbH, Germany).…”

Section: Introductionmentioning

confidence: 99%

Coupling Rhodium‐Catalyzed Hydroformylation of 10‐Undecenitrile with Organic Solvent Nanofiltration: Toluene Solution versus Solvent‐Free Processes

et al. 2019

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Intensification of the rhodium‐catalyzed hydroformylation process to produce 12‐oxo‐dodecanenitrile from biosourced 10‐undecenitrile was performed by coupling the reaction with organic solvent nanofiltration (OSN) for the recycling of the expensive Rh catalyst and the ligands. Four phosphorus‐based ligands were compared with respect to their catalytic performance and rejection in OSN. Biphephos showed the best compromise and up to 3 reaction‐OSN cycles were performed in toluene. A good recycling of the catalytic system was evidenced arising from the OSN (up to 88 % rejection). In order to develop a greener process, a similar approach was achieved in bulk (i. e. solvent‐free medium), thus proving the catalyst recycling feasibility but also that the optimal OSN conditions are not the same as for toluene. Finally, integration of OSN in the overall production process is discussed, aiming at the proposal of a hybrid separation process involving a combination of OSN and distillation for an energy‐efficient separation step.

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Recycling Homogeneous Catalysts Simply by Organic Solvent Nanofiltration: New Ways to Efficient Catalysis

Cited by 42 publications

References 29 publications

Investigations on Catalyst Stability and Product Isolation in the Extractive Oxidative Desulfurization of Fuels Using Polyoxometalates and Molecular Oxygen

Investigations on Catalyst Stability and Product Isolation in the Extractive Oxidative Desulfurization of Fuels Using Polyoxometalates and Molecular Oxygen

Recent Advances Utilized in the Recycling of Homogeneous Catalysis

Coupling Rhodium‐Catalyzed Hydroformylation of 10‐Undecenitrile with Organic Solvent Nanofiltration: Toluene Solution versus Solvent‐Free Processes

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