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Dutch Resolution of Racemates and the Roles of Solid Solution Formation and Nucleation Inhibition

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Novel Optical Resolution Technologies

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 269))

Abstract

An overview is given of the principles of Pasteur resolutions via separation of diastereomeric salts.Thereafter, primary nucleation processes of (chiral) organic compounds in supersaturated solution are consideredfollowed by crystal growth in the presence of tailor-made additives. A representative example of a DutchResolution is presented, the concept of families of resolving agents is defined and examples are given.The phenomenon of reversed Dutch Resolution, resolution of mixtures of families of racemates, is illustrated.The roles of both solid solution formation and nucleation inhibition in Dutch Resolution are discussed.The work is concluded with the results of a broadly based search for nucleation inhibitors for phenylethylamine as resolving agent. This search can serve as a model for the discovery of nucleation inhibitorsfor other resolving agents. The specific role of bifunctional family members of resolving agents as possiblenucleation inhibitors is also discussed.

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Authors and Affiliations

  1. Syncom BV, Kadijk 3, 9747, Groningen AT, The Netherlands

    Richard M. Kellogg & Ton R. Vries

  2. DSM Research, Life Sciences—Advanced Synthesis & Catalysis, P.O. Box 18, 6160, Geleen MD, The Netherlands

    Bernard Kaptein

Authors
  1. Richard M. Kellogg
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  2. Bernard Kaptein
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  3. Ton R. Vries
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Correspondence to Richard M. Kellogg .

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Kenichi Sakai Noriaki Hirayama Rui Tamura

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Kellogg, R.M., Kaptein, B., Vries, T.R. (2007). Dutch Resolution of Racemates and the Roles of Solid Solution Formation and Nucleation Inhibition. In: Sakai, K., Hirayama, N., Tamura, R. (eds) Novel Optical Resolution Technologies. Topics in Current Chemistry, vol 269. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2006_095

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