Homogeneously catalyzed hydroamination in a Taylor–Couette reactor using a thermormorphic multicomponent solvent system

Abstract

In order to design an innovative continuous process for the conversion of the renewable β-myrcene, three methodical steps are shown in this paper to find a setup for the demanding homogeneously catalyzed hydroamination. First step is the theoretical and practical design of a suitable thermomorphic multicomponent solvent (TMS)-systems for recycling the catalyst system. The necessary phase equilibria were successfully investigated by modelling using the Perturbed Chain – Statistical Associating Fluid Theory (PC-SAFT) and measuring liquid–liquid equilibria of the ternary systems substrates/solvents mixtures at the separation temperature. In the next step the promising TMS-system was subsequently used to investigate the recycling of the catalyst in continuous operation. A Taylor–Couette reactor (TCR) was developed and modified for the application in homogeneous transition metal catalysis. The reactor was integrated in a miniplant setup and a continuous recycling of the catalyst phase as well as an efficient synthesis of the desired terpenyl amines is achieved in 3 complete cycles. The results show that the TCR is suitable for the hydroamination and generates high conversion and yields (XMyr=82%, YHA=80%). Recycling experiments were conducted successfully in the miniplant setup to show the long-term operation in a period of 24h.