Semi-continuous temperature cycle-induced deracemization using an axially chiral naphthamide

17 January 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

This study outlines a practical semi-continuous method for temperature cycle-induced deracemization (TCID) using a batch mode crystallizer. We employed an axially chiral naphthamide derivative as a model compound, and deracemized the crystalline phase by conventional TCID. To achieve a continuity of deracemization, we harvested a part of the suspension after the conventional TCID, then feeding a new racemic suspension into the enriched suspension and applying temperature cycles. By leaving a highly enriched crystalline phase as seed crystals to direct the chirality of the following enrichment, the enrichment process was significantly accelerated, verifying the stable and high production efficiency. Furthermore, from the perspective of process productivity, the moderate suspension density is optimal for efficient deracemization. In the naphthamide system, up to 7.71 g·L−1·h−1 of the productivity was achieved. Thanks to the simple operation, the method described here is applicable for most of batch mode deracemization reported to date. In terms of industrial application, the semi-continuous deracemization could be a good option to utilize the existing batch crystallizers.

Keywords

Crystallization
Resolution
Continuous crystallization

Supplementary materials

Title
Description
Actions
Title
Supporting Information
Description
Solubility data of a naphtahmide derivative
Actions

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.