Concomitant Polymorphism and Nucleation Control of <i>DL</i>‐Methionine Through Antisolvent Crystallization

Suresh, Manivel; Srinivasan, K.

doi:10.1002/ceat.202000300

Cited by 9 publications

(9 citation statements)

References 28 publications

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“…According to the POM photographs of the crystallized products, at a FA/W ratio of 1:1, platelike particles were obtained, corresponding to the typical crystal habit of Form I (Figure 3a); while needle-like crystals representing Form II are obtained at a FA/W ratio of 2:1 (Figure 3b). 38,39 Previously, Srinivasan et al 40 prepared methionine polymorphs by adding different amounts of ethanol in water, i.e., β crystals were obtained as the volume fraction of ethanol was less than 0.06, while the α crystals were obtained at a high ethanol fraction (>0.1). Thus, it is important to reveal the reason that results in the formation of distinct polymorphs under different solvent/antisolvent ratios.…”

Section: Resultsmentioning

confidence: 99%

“…Previously, Srinivasan et al prepared methionine polymorphs by adding different amounts of ethanol in water, i.e., β crystals were obtained as the volume fraction of ethanol was less than 0.06, while the α crystals were obtained at a high ethanol fraction (>0.1). Thus, it is important to reveal the reason that results in the formation of distinct polymorphs under different solvent/antisolvent ratios.…”

Section: Resultsmentioning

confidence: 99%

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Solvent–Antisolvent Competitive Interactions Mediate Imidacloprid Polymorphs in Antisolvent Crystallization

Xue

Han

et al. 2021

Crystal Growth & Design

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Imidacloprid (IMI) polymorphs were first found to be sensitive to the content of antisolvent in an antisolvent crystallization process using formic acid (FA) as a solvent and water (W) as an antisolvent. Characterized by XRD, DSC, POM, and Raman, the obtained crystals change from Form II into Form I as the FA/W ratio becomes lower than 1:1. Combined with Hirshfeld surface analysis, it illustrates that IMI molecules have the tail-to-tail and tail-to-head packing modes at a FA/W ratio of 1:1, whereas they adopt the tail-to-tail parallel packing at a FA/W ratio of 2:1. Molecular dynamic simulations disclose that the molecular conformations in the IMI aggregates turn to be approximately the distinct conformations in the corresponding unit cells of crystal Form I and II. The competing parameters were put forward around the active sites of IMI on the basis of the coordination numbers calculated through RDF profiles to understand deeply the competition mechanism of the solute–solvent interactions versus the solute–antisolvent interactions. It is found that as the content of water increases, the solute–antisolvent interactions gradually turn to be dominant around the specific sites, which promotes the conformation change of IMI and then facilitates the nucleation for Form I. These results provide a useful route to study the nucleation pathway of polymorphic products.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Solvent–Antisolvent Competitive Interactions Mediate Imidacloprid Polymorphs in Antisolvent Crystallization

Xue

Han

et al. 2021

Crystal Growth & Design

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“…Nonetheless, if the supersaturation ratio was too high, liquid–liquid phase separation would lead to no crystals, as shown in Figure . Suresh et al revealed the effect of supersaturation levels on the polymorphic form of dl -methionine obtained by antisolvent crystallization, during which the supersaturation was proportionately generated by change in the antisolvent concentrations, as shown in Figure . The results indicated that the stable β-polymorph formed at low supersaturation levels, while a mixture of α- and β-polymorphs was detected at intermediate supersaturation levels, and the metastable α-form was obtained at high supersaturation levels .…”

Section: Traditional Methods For Preparation and Regulation Of Drug P...mentioning

confidence: 99%

“…The results indicated that the stable β-polymorph formed at low supersaturation levels, while a mixture of αand β-polymorphs was detected at intermediate supersaturation levels, and the metastable α-form was obtained at high supersaturation levels. 20 Form I and form II of clopidogrel hydrogen sulfate have been widely applied in the cure of thrombotic diseases. Reactive crystallization is one of the most used techniques for the industrial production of form I of clopidogrel hydrogen sulfate.…”

Section: Traditional Methods For Preparation and Regulation Of Drug P...mentioning

confidence: 99%

An Overview on Polymorph Preparation Methods of Active Pharmaceutical Ingredients

Zhou,

Lv,

Liu

et al. 2023

Crystal Growth & Design

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Polymorphism, which plays an important role in the pharmaceutical industry, is quite common for active pharmaceutical ingredients (API). Owing to the structural differences between polymorphs, they often possess remarkably different physical and chemical properties, thus leading to diversity in curative effects and shelf life. How to precisely control the polymorph of API has attracted the attention of researchers around the world. In this paper, the regulation methods of drug polymorphs are comprehensively reviewed, to give a better view for the future research. The traditional method, including the control of the nucleation and growth process, is systematically introduced and analyzed from the aspects of the action mechanism and their application in recent years. In addition, novel techniques, including templates, microfluidics technology, ultrasound, laser, ionic liquids, and supramolecular gels, are expounded and analyzed in detail. Considerable studies indicate that polymorph control of API is a promising research field. Finally, the existing problems are discussed and the future prospects are given.

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“…Recent studies have revealed the detailed kinetics of orientated attachment and the importance of desolvation on particle aggregation during crystal nucleation [80,151]. The large barrier of this step results in the rare event of crystal nucleation, which may also produce simultaneous nucleation of two crystal structures (polymorphs) [152][153][154], i.e., concomitant crystallization of polymorphs when the nucleation barrier for two polymorphs were comparable. Furthermore, the absence of structure correspondence and solvent-dependent molecular association indicate multiple aggregates of solutes regulated by their surrounding environment that is formed either in pre-nucleation or in the course of nucleation stages.…”

Section: Aggregation-based Multiple Nucleation Pathwaysmentioning

confidence: 99%

Molecular Mechanism of Organic Crystal Nucleation: A Perspective of Solution Chemistry and Polymorphism

Zhou

Tang

2022

Crystals

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Crystal nucleation determining the formation and assembly pathway of first organic materials is the central science of various scientific disciplines such as chemical, geochemical, biological, and synthetic materials. However, our current understanding of the molecular mechanisms of nucleation remains limited. Over the past decades, the advancements of new experimental and computational techniques have renewed numerous interests in detailed molecular mechanisms of crystal nucleation, especially structure evolution and solution chemistry. These efforts bifurcate into two categories: (modified) classical nucleation theory (CNT) and non-classical nucleation mechanisms. In this review, we briefly introduce the two nucleation mechanisms and summarize current molecular understandings of crystal nucleation that are specifically applied in polymorphic crystallization systems of small organic molecules. Many important aspects of crystal nucleation including molecular association, solvation, aromatic interactions, and hierarchy in intermolecular interactions were examined and discussed for a series of organic molecular systems. The new understandings relating to molecular self-assembly in nucleating systems have suggested more complex multiple nucleation pathways that are associated with the formation and evolution of molecular aggregates in solution.

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Concomitant Polymorphism and Nucleation Control of DL‐Methionine Through Antisolvent Crystallization

Cited by 9 publications

References 28 publications

Solvent–Antisolvent Competitive Interactions Mediate Imidacloprid Polymorphs in Antisolvent Crystallization

Solvent–Antisolvent Competitive Interactions Mediate Imidacloprid Polymorphs in Antisolvent Crystallization

An Overview on Polymorph Preparation Methods of Active Pharmaceutical Ingredients

Molecular Mechanism of Organic Crystal Nucleation: A Perspective of Solution Chemistry and Polymorphism

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