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  • Continuous homogeneous hydroformylation with integrated membrane separation : kinetics, mechanics and jet loop reactor technology Citation for published version (APA): Hristova, S. A. (2013). Continuous homogeneous hydroformylation with integrated membrane separation : kinetics, mechanics and jet loop reactor technology. Eindhoven: Technische Universiteit Eindhoven. https://doi.org/10.6100/IR760621

    DOI: 10.6100/IR760621

    Document status and date: Published: 02/12/2013

    Document Version: Publisher’s PDF, also known as Version of Record (includes final page, issue and volume numbers)

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    Download date: 20. Apr. 2020

    https://doi.org/10.6100/IR760621 https://doi.org/10.6100/IR760621 https://research.tue.nl/en/publications/continuous-homogeneous-hydroformylation-with-integrated-membrane-separation--kinetics-mechanics-and-jet-loop-reactor-technology(b828c30b-5438-4d9c-8eb2-2ca2dd546190).html

  • Continuous Homogeneous Hydroformylation with

    Integrated Membrane Separation: Kinetics, Mechanism and Jet Loop Reactor Technology

    PROEFSCHRIFT

    ter verkrijging van de graad van doctor aan de Technische Universiteit Eindhoven, op gezag van de rector magnificus prof.dr.ir. C.J. van Duijn,

    voor een commissie aangewezen door het College voor Promoties, in het openbaar te verdedigen op maandag 2 december 2013 om 16:00 uur

    door

    Snezhana Asenova Hristova

    geboren te Kardzhali, Bulgarije

  • Dit proefschrift is goedgekeurd door de promotoren en de samenstelling van de promotiecommissie is als volgt: voorzitter: prof.dr.ir. J.C. Schouten 1e promotor: prof.dr. D. Vogt 2e promotor: prof.dr. C. Müller leden: prof.dr. P.W.N.M. van Leeuwen (ICIQ)

    prof.dr. D. Cole-Hamilton (University of St Andrews) prof.dr. P. Wasserscheid (Friedrich-Alexander- Universität)

    adviseur(s): prof.dr. R. Franke (Evonik Industries AG)

  • "Essentially, all models are wrong, but some are useful"

    George E. P. Box

  • A catalogue record is available from the Eindhoven University of Technology Library

    ISBN: 978-90-386-3490-6

    The research described in this thesis was part of the European Community's Seventh Framework Programme (FP7/2007-2013), F3 Factory and received financial support under grant agreement n° 228867.

    Cover design by Sabriye Güven

    Druk: TU/e PrintService

    Copyright © 2013 by Snezhana A. Hristova

  • Continuous Homogeneous Hydroformylation

    with

    Integrated Membrane Separation:

    Kinetics, Mechanism and Jet Loop Reactor Technology

  • Table of Contents Chapter 1 ............................................................................................................................................................................ 1

    1.1 Hydroformylation ............................................................................................................................................. 2

    1.2 Hydroformylation Mechanism .......................................................................................................................... 2

    1.3 Kinetic Studies .................................................................................................................................................. 4

    1.4 Jet Loop Reactor ............................................................................................................................................... 5

    1.5 Catalyst Recycling in Continuous Hydroformylation ....................................................................................... 6

    1.6 Ceramic Membrane Nanofiltration ................................................................................................................... 8

    1.7 Aim and Scope of the Research ...................................................................................................................... 10

    1.8 References ...................................................................................................................................................... 11

    Chapter 2 .......................................................................................................................................................................... 13

    2.1 Jet Loop Reactor with Integrated Membrane Separation for Continuous Hydroformylation ......................... 14

    2.2 Reactor Setup .................................................................................................................................................. 15

    2.3 Design Considerations .................................................................................................................................... 19

    2.3.1 Reactor ................................................................................................................................................... 19

    2.3.2 Membrane .............................................................................................................................................. 25

    2.4 Conclusions .................................................................................................................................................... 26

    2.5 Experimental ................................................................................................................................................... 26

    2.5.1 Materials ................................................................................................................................................ 26

    2.5.2 Batch gas absorption experiments .......................................................................................................... 26

    2.6 References ...................................................................................................................................................... 27

    Chapter 3 .......................................................................................................................................................................... 29

    3.1 Introduction .................................................................................................................................................... 30

    3.2 Batch Kinetic Experiments ............................................................................................................................. 31

    3.2.1 Effect of stirring rate to eliminate mass transfer limitations .................................................................. 31

    3.2.2 Mechanism ............................................................................................................................................. 32

    3.2.3 Rate equation and experimental design.................................................................................................. 34

    3.2.4 Hydrogen and carbon monoxide concentrations in solution .................................................................. 36

    3.2.5 Estimation of rate equation parameters .................................................................................................. 37

    3.3 Continuous Reaction ....................................................................................................................................... 38

    3.4 Conclusions .................................................................................................................................................... 40

  • 3.5 Experimental ...................................................................................................................................................41

    3.5.1 Materials ..............................................................................