Collaborative Research Center/Transregio 63

"Integrated Chemical Processes in Liquid Multiphase Systems"

>Research>Completed Projects>Project B5 E

B5 Hydroformylation and Hydroesterification of Petrochemicals and Oleochemicals in Thermomorphic Solvent Systems in a Continuously Operated Miniplant with Highly Efficient Catalyst Recycling (completed)

Sub-Coordinators: Prof. Dr.-Ing. Andrzej Górak, Prof. Dr. Arno Behr

State of the art

In the first funding period a continuously operated miniplant for the hydroformylation of 1-dodecene was designed, built and tested. To realize an efficient catalyst recycling, a solvent-system with a highly temperature dependent miscibility gap is used. The miniplant contains a continuously stirred tank reactor (CSTR) where the homogeneous catalyzed reaction takes place and a liquid/liquid phase separator in which the product-phase and the catalyst-phase are separated from each other. After phase-separation the catalyst is fed back into the reactor and the product is taken out of the process. It was possible to realize a steady state operation of this miniplant for 200 h with a yield of 63 % of the main product.

Research goals

During the following research the catalyzed recycling has to be improved further. Therefore the influence of an organic solvent nanofiltration membrane on the catalyst behavior will be investigated, to expand the miniplant with a nanofiltration-unit and increase the effectiveness of the process. Furthermore the non-polar solvent has to be separated from the product with a distillation unit and reused in the reaction-step. Also an optimal designed reactor (project B1) has to be tested in the miniplant and compared to the CSTR, in order increase the yield. Further scientific investigations on hydroformylation and hydroesterification reactions in the miniplant lead to the processing of renewable materials.

More information
Recent Publications

Dreimann, J. M.; Hoffmann, F.; Skiborowski, M.; Behr, A.; Vorholt, A. J. Merging Thermomorphic Solvent Systems and Organic Solvent Nanofiltration for Hybrid Catalyst Recovery in a Hydroformylation Process. Ind. Eng. Chem. Res., 56(5), 1354-1359, 2017. [doi: 10.1021/acs.iecr.6b04249]

Dreimann, J. M.; Fassbach, T. A.; Fuchs, S.; Fuerst, M. R. L.; Geide, T.; Kuhlmann, R.; Ostrowski, K. A.; Stadler, A.; Sidensticker, T.; Vogelsang, D.; Warmeling, H. V. F.; Vorholt, A. J. From Lab Curiosity to a Continuously Operated Process: Development of Thermomorphic Solvent Systems. Chem. Eng. Tech., 89, 252-262, 2017. [doi:10.1002/cite.201600119]

Scharzec, B.; Waltermann, T.; Skiborowski, M. A Systematic Approach towards Synthesis and Design of Pervaporation-Assisted Separation Processes. Chem. Eng. Tech., 11, 1534–1549, 2017. []


Dreimann, J. M.; Lutze, P.; Zagajewski, M.; Behr, A.; Górak, A.; Vorholt, A. J. Highly integrated reactor–separator systems for the recycling of homogeneous catalysts. Chem. Eng. Process., 99, 124-131, 2016. [doi:10.1016/j.cep.2015.07.019]

Dreimann, J. M.; Skiborowski, M.; Behr, A.; Vorholt, A. J. Recycling Homogeneous Catalysts Simply by Organic Solvent Nanofiltration: New Ways to Efficient Catalysis. ChemCatChem, 8, 3330-3333, 2016. [doi/10.1002/cctc.201601018]

Dreimann, J. M.; Vorholt, A.; Skiborowski, M.; Behr, A. Removal of Homogeneous Precious Metal Catalysts via Organic Solvent Nanofiltration. Chem. Eng. Trans., 47, 343-348, 2016. [doi:0.3303/CET1647058]

Dreimann, J. M.; Warmeling, H.; Weimann, J. N.; Künnemann, K.; Behr, A.; Vorholt, A. J. Increasing selectivity of the hydroformylation in a miniplant: Catalyst, solvent, and olefin recycle in two loops. AIChE J., 62(12), 4377-4383, 2016. [doi:10.1002/aic.15345]

Gaide, T.; Dreimann, J.; Behr, A.; Vorholt, A. J. Overcoming Phase-Transfer Limitations in the Conversion of Lipophilic Oleo Compounds in Aqueous Media-A Thermomorphic Approach. Angew. Chem. Int. Ed., 55(8), 2924-2928, 2016. [doi:10.1002/anie.201510738]

Gaide, T.; Dreimann, J.; Behr, A.; Vorholt, A. J. Überwindung von Phasentransportlimitierungen in der Umsetzung lipophiler Oleoverbindungen in wässrigen Medien – ein temperaturgesteuerter Ansatz. Angew. Chem., 128(8), 2977-2981, 2016. [doi:10.1002/ange.201510738]

Zagajewski, M.; Dreimann, J.; Thönes, M.; Behr, A. Rhodium catalyzed hydroformylation of 1-dodecene using an advanced solvent system: Towards highly efficient catalyst recycling. Chem. Eng. Process., 99, 115-123, 2016. [doi:10.1016/j.cep.2015.06.014]


Haßelberg, J. Process development for the synthesis of saturated branched fatty derivatives: Homogeneous and heterogeneous catalysis in miniplant scale. Technische Universität Dortmund, 2016.[More]


Zagajewski, M. Planung, Bau und Betrieb einer Miniplant zur kontinuierlichen Hydroformylierung von 1-Dodecen in thermomorphen Mehrkomponenten-Lösungsmittelsystemen. Technische Universität Dortmund, 2015. [More]

Last updated:18-01-2022