Chapter 5. Production of Chiral C3 and C4 Units via Microbial Resolution of 2,3-Dichloro-1-propanol, 3-Chloro-1,2-propanediol and Related Halohydrins

  1. Dr. Hans-Ulrich Blaser3,
  2. Dr. Elke Schmidt4
  1. Naoya Kasai1,
  2. Toshio Suzuki2

Published Online: 13 JAN 2004

DOI: 10.1002/3527602151.ch13

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

Kasai, N. and Suzuki, T. (2004) Production of Chiral C3 and C4 Units via Microbial Resolution of 2,3-Dichloro-1-propanol, 3-Chloro-1,2-propanediol and Related Halohydrins, 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.ch13

Editor Information

  1. 3

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

  2. 4

    Syngenta Crop Protection AG, CH-4058 Basel, Switzerland

Author Information

  1. 1

    Osaka Prefecture University, Laboratory of Food Chemistry, Division of Applied Biological Chemistry, Graduate School of Agriculture & Biological Sciences, Gakuen-cho, Sakai, Osaka 599-8531, Japan

  2. 2

    Research Laboratories of DAISO Co. Ltd, 9 Otakasu-Cho, Amagasaki, Hyogo 660-0842, Japan

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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Keywords:

  • C3 units;
  • C4 units;
  • microbial resolution;
  • 2,3-dichloro-1-propanol;
  • 3-chloro-1,2-propanediol;
  • halohydrins;
  • immobilized cells;
  • scale-up;
  • stereoselectivity;
  • purification;
  • racemization

Summary

This chapter contains sections titled:

  • Introduction

  • C3 Chiral Synthetic Units

    • (R)- and (S)-2,3-dichloro-1-propanol (DCP)

      • (R)-2,3-Dichloro-1-propanol (DCP) Assimilating Bacterium for (S)-2,3-Dichloro-1-propanol (DCP) and (R)-epichlorohydrin (EP) Production

      • (S)-Epichlorohydrin (EP) Production and Isolation of a DCP Assimilating Bacterium

    • Large-Scale Trials Using Immobilized Cells

      • Production on a 100 L Scale

      • Production on a 5000 L Scale

    • Production of (R)- and (S)-3-Chloro-1,2-propanediol (CPD) and (R)- and (S)-Glycidol (GLD)

      • Screening of (R)- and (S)-3-Chloro-1,2-propanediol (CPD) Assimilating Bacteria

    • Scale-up of the Production of C3 Chiral Synthetic Units

      • Fed-Batch Fermentation and Control

      • Control Logic System

  • Production of C4 Chiral Synthetic Units

    • Production of 4-Chloro-3-acetoxybutyronitrile (BNOAc) by Ester-Degrading Enzymes

    • Production of (R)-4-Chloro-3-hydroxy-butyrate (CHB) and (S)-3-hydroxy-γ-butyrolactone (HL) by Enterobacter sp.

      • Cultivation and Preparation of Enterobacter sp. Resting Cells with High Degradation Activity

      • Ton-Scale Production of (R)-4-Chloro-3-hydroxy-butyrate (CHB) and (S)-3-Hydroxy-c-butyrolactone (HL) by the Resting Cells of Enterobacter sp.

      • Effect of Base on the Stereoselectivity of Enterobacter sp.

      • Intelligent Production of (R)-Methyl 4-chloro-3-hydroxybutyrate (CHBM) and (S)-3-Hydroxy-γ-butyrolactone (HL) with a Fed-Batch System of Substrate

  • Purification of Chiral Units

  • Racemization

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