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.

中文翻译：

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铑催化的10-十一碳烯腈与有机溶剂纳米过滤的加氢甲酰化：甲苯溶液与无溶剂工艺的比较。

通过将反应与有机溶剂纳滤（OSN）偶联以回收昂贵的Rh催化剂和配体，进行了铑催化的加氢甲酰化工艺，以从生物来源的10-十一碳烯腈生产12-氧代十二碳二烯腈。比较了四种基于磷的配体的催化性能和在OSN中的排斥。Biphephos显示出最佳的折衷效果，并且在甲苯中进行了多达3个反应-OSN循环。证明了OSN（高达88％的废品率）可对催化系统进行良好的循环利用。为了发展绿色工艺，在散装（即无溶剂的介质）中实现了类似的方法，从而证明了催化剂再循环的可行性，而且最佳的OSN条件不同于甲苯。最后，