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Article Dans Une Revue Green Chemistry Année : 2020

Continuous hydroformylation of 1-decene in an aqueous biphasic system enabled by methylated cyclodextrins

Résumé

For the first time, randomly methylated β-cyclodextrin was applied as the mass transfer agent in a continuous process. Considering the example of the Rh-catalyzed hydroformylation of 1-decene, process development was shown, where cyclodextrin was used together with a catalyst system that was continuously recovered and recycled using an aqueous biphasic system. In initial experiments, water-soluble and commercially available Rh/TPPTS and Rh/sulfoxantphos catalyst systems were scaled up from 50 ml into 1000 ml high-pressure autoclave systems to demonstrate their scalability. Both these systems were compared, and they afforded excellent chemoselectivity (>99%) toward the desired linear aldehyde product. In particular, higher regioselectivity (up to 31) was achieved for the Rh/sulfoxantphos system. Investigations regarding the long-term stability of the mass transfer agent and both catalyst systems were carried out in a continuously operated miniplant process. It was shown that the process could be successfully operated under the steady state for over 200 h with chemoselectivity of >97% toward the desired aldehyde product. Simultaneously, extremely low Rh leaching (total: 0.59%) was observed over the entire period of 200 h.
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Origine : Publication financée par une institution
Licence : CC BY - Paternité

Dates et versions

hal-02881844 , version 1 (15-12-2023)

Identifiants

Citer

K. Künnemann, L. Schurm, D. Lange, T. Seidensticker, Sébastien Tilloy, et al.. Continuous hydroformylation of 1-decene in an aqueous biphasic system enabled by methylated cyclodextrins. Green Chemistry, 2020, 22 (12), pp.3809-3819. ⟨10.1039/D0GC00820F⟩. ⟨hal-02881844⟩
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