Chiral compounds can exist as pairs of nonsuperimposable
stereoisomers
(enantiomers) possessing the same physical properties but interacting
differently with biological systems. This makes them interesting materials
to be explored by the pharmaceutical and food industries. In this
study, to obtain pure enantiomers from their conglomerates, a method
that involves using a two-vessel system for deracemization of N-(2-methylbenzylidene) phenylglycine amide (NMPA) was developed.
In this method, a suspension was transferred with a pulsating pumping
profile between two inter-connected stirred vessels that were set
at constant temperatures. As the suspension was exposed to more rapid
changes in temperature, it resulted in the speeding up of the process
and thus enhancing productivity in comparison to a single vessel system.
The results confirmed successful deracemization of NMPA. A modified
pumping profile and tubing design eliminated the issue of clogging
of the transfer tubes and ensured effective suspension transfer for
longer durations. Operating parameters, such as initial enantiomeric
excess, vessel residence time, and suspension density were also investigated.
In this method, optimization of residence time was necessary to enhance
the efficiency of the process further. Results confirmed that this
methodology has the potential to be more adaptable and scalable as
it involved no mechanical attrition.
Enantiomeric
purity is of prime importance for several industries,
specifically in the production of pharmaceuticals. Crystallization
processes can be used to obtain pure enantiomers in a suitable solid
form. However, some process variants inherently rely on kinetic enhancement
(preferential crystallization) of the desired enantiomer or on complex
interactions of several phenomena (e.g., attrition-enhanced deracemization
and Viedma ripening). Thus, a process analytical technology able to
measure the enantiomeric composition of both the solid phase and the
liquid phase would be valuable to track and eventually control such
processes. This study presents the design and development of a novel
automated analytical monitoring system that achieves this. The designed
setup tracks the enantiomeric excess (
ee
) using a
continuous closed-loop sampling loop that is coupled to a polarimeter
and an attenuated total reflection Fourier transform infrared spectroscopy
spectrometer. By heating the loop and alternately sampling either
the liquid or the suspension, the combination of these measurements
allows tracking of the
ee
of both the liquid and
the solid. This work demonstrates a proof of concept of both the experimental
and theoretical aspects of the new system.
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