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A Microfluidic Approach for the Study of Ice and Clathrate Hydrate Crystallization
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Crystallization of a polymorphic hydrate system.

F Tian1, H Qu, M Louhi-Kultanen

  • 1Faculty of Pharmaceutical Sciences, Department of Pharmaceutics and Analytical Chemistry, University of Copenhagen, Copenhagen, Denmark.

Journal of Pharmaceutical Sciences
|July 2, 2009
PubMed
Summary
This summary is machine-generated.

Nitrofurantoin forms two monohydrates with different crystal structures. Hydrate II crystallizes more readily and is more stable, hindering the formation of hydrate I due to slower crystallization kinetics and smaller free energy differences.

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Area of Science:

  • Crystallization Science
  • Solid-State Chemistry
  • Pharmaceutical Polymorphism

Background:

  • Nitrofurantoin exists as multiple hydrate forms with identical chemical composition but distinct crystal arrangements.
  • Understanding the formation and stability of these nitrofurantoin monohydrates is crucial for pharmaceutical formulation and manufacturing.

Purpose of the Study:

  • To investigate the crystallization behavior and relative stability of nitrofurantoin monohydrates I and II.
  • To elucidate the factors influencing the preferential formation of one hydrate over the other.

Main Methods:

  • Evaporative crystallization experiments were conducted to study hydrate formation under varying supersaturation and solvent compositions.
  • Cooling crystallization experiments, including seeding trials with hydrate I, were performed to assess nucleation and growth dynamics.
  • Solubility measurements were carried out to determine the thermodynamic stability of both hydrates.

Main Results:

  • Nitrofurantoin monohydrate II exhibited significantly faster crystallization kinetics compared to hydrate I.
  • During cooling crystallization, hydrate II dominated, preventing hydrate I formation even with seeding.
  • Hydrate II demonstrated greater thermodynamic stability, evidenced by its lower solubility (110 ± 4 µg/mL vs. 131 ± 12 µg/mL for hydrate I).
  • The crystal structure of hydrate II showed more extensive hydrogen bonding, contributing to its favorable crystallization.

Conclusions:

  • The preferential formation of nitrofurantoin monohydrate II is attributed to its faster crystallization kinetics, greater thermodynamic stability, and more favorable crystal packing with enhanced hydrogen bonding.
  • The small solubility difference and slow crystallization of hydrate I present challenges for its independent production.