Chapter 3. The Chiral Switch of Metolachlor: The Development of a Large-Scale Enantioselective Catalytic Process†

  1. Dr. Hans-Ulrich Blaser2,
  2. Dr. Elke Schmidt3
  1. Dr. Hans-Ulrich Blaser2,
  2. Reinhard Hanreich1,
  3. Hans-Dieter Schneider1,
  4. Felix Spindler2,
  5. Beat Steinacher1

Published Online: 13 JAN 2004

DOI: 10.1002/3527602151.ch3

Book Title

Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions

Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions

Additional Information

How to Cite

Blaser, H.-U., Hanreich, R., Schneider, H.-D., Spindler, F. and Steinacher, B. (2004) The Chiral Switch of Metolachlor: The Development of a Large-Scale Enantioselective Catalytic Process, in Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions (eds H.-U. Blaser and E. Schmidt), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, FRG. doi: 10.1002/3527602151.ch3

Editor Information

  1. 2

    Solvias AG, P.O. Box, CH-4002 Basel, Switzerland

  2. 3

    Syngenta Crop Protection AG, CH-4058 Basel, Switzerland

Author Information

  1. 1

    Syngenta Crop Protection, Münchwilen AG, CH-4333 Münchwilen, Switzerland

  2. 2

    Solvias AG, P.O. Box, CH-4002 Basel, Switzerland

  1. †

    This is an amended version of a paper first published in Chimia 1999, 53, 275.

Publication History

  1. Published Online: 13 JAN 2004
  2. Published Print: 6 NOV 2003

ISBN Information

Print ISBN: 9783527306312

Online ISBN: 9783527602155

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CHAPTER TOOLS

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Keywords:

  • chiral switch;
  • metolachlor;
  • enantioselective catalysis;
  • hydrogenation;
  • substitution;
  • alkylation;
  • imine hydrogenation;
  • diphosphine complexes;
  • ligand;
  • MEA imine;
  • reactor;
  • scale-up

Summary

This chapter contains sections titled:

  • Introduction and Problem Statement

  • Route Selection

    • Enamide Hydrogenation

    • Nucleophilic Substitution of an (R)-Methoxyisopropanol Derivative

    • Hydrogenation of MEA Imine

    • Catalytic Alkylation with Racemic Methoxyisopropanol

    • Assessment and Screening of the Proposed Routes

  • Imine Hydrogenation: Laboratory Process

    • Finding the Right Metal-Ligand Combination

      • Screening of Rh-Diphosphine Complexes

      • Screening of Ir-Diphosphine Complexes

      • Synthesis and Screening of a New Ligand Class

    • Optimization of Reaction Medium and Conditions

    • Ligand Fine Tuning

  • Imine Hydrogenation: Technical Process

    • Strategy for Process Development

    • The Production of the MEA Imine at the Required Quality

    • Scale-up of the Ligand Synthesis

    • Fine Optimization of the Ir-Catalyst Formulation

    • Choice of Reactor Technology

    • Scale-Up to the Production Autoclave

    • Work-up, Separation of the Catalyst from the Product

  • Summary and Conclusions

  • Acknowledgements

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