Mixing Effect on Stoichiometric Diversity in Benzoic Acid–Sodium Benzoate Cocrystals

Chen, Tzu Hsuan; Yeh, Ken; Chen, Chih‐Wei; Lee, Hung Lin; Hsu, Yu‐Kuei; Lee, Tu

doi:10.1021/acs.cgd.8b01220

Cited by 7 publications

(8 citation statements)

References 35 publications

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“…Characterizations of 2:1 HBz-NaBz co-crystals: All of the TGA scans of co-crystals synthesized at different S 0 values without templating molecules underwent weight losses between 90 to 250 • C, as illustrated in Figure S6, corresponding to the thermal decomposition of HBz [12]. Those weight losses of 59.6-63.1 wt.% were quite close to the theoretical weight loss of 62.9 wt.% (Equation (S1)).…”

Section: Resultsmentioning

confidence: 99%

“…Taking caffeine-maleic acid co-crystals, for example, the solubility values of the stoichiometric ratios of 2:1 and 1:1 are starkly different [11]. In another study, a co-crystal with a single stoichiometric ratio was very difficult to obtain in a bench-scale stirred tank due to hydrodynamic mixing [12]. This evidence suggests that co-crystallization is highly process dependent.…”

Section: Introductionmentioning

confidence: 99%

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Co-Crystallization Kinetics of 2:1 Benzoic Acid–Sodium Benzoate Co-Crystal: The Effect of Templating Molecules in a Solution

2021

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The addition of dissolved templating molecules in crystallization will create “supramolecular assemblies” within the solution, serving as “anchor points” for the solute molecules to nucleate and grow. In this work, nucleation and crystal growth kinetics of 2:1 benzoic acid (HBz)–sodium benzoate (NaBz) co-crystallization with or without templates in a solution were analyzed by monitoring the concentration of the mother liquor during cooling crystallization. The results showed that the addition of the dissolved 2:1 or 1:1 HBz–NaBz co-crystals as templating molecules could reduce the critical free energy barrier of 2:1 HBz–NaBz co-crystal during its nucleation, but did not significantly affect the order of crystal growth rate. On the other hand, the critical free energy barrier of the nucleation process was increased if dissolved NaBz was used as a templating molecule, while a significant rise in the order of crystal growth rate occurred. The crystal habit obtained from the NaBz-templated system was needle-like, suggesting that sodium–sodium coordination chains of NaBz supramolecular assemblies in the solution phase were responsible for creating elongated crystals. Conversely, a large prismatic crystal habit found in non-templated and 2:1 and 1:1 HBz–NaBz co-crystal-templated systems implied that those templating molecules formed sparsely interconnected supramolecular assemblies in the solution phase.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Co-Crystallization Kinetics of 2:1 Benzoic Acid–Sodium Benzoate Co-Crystal: The Effect of Templating Molecules in a Solution

2021

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“…18 The other examples demonstrating the importance of fluid hydrodynamics are the case of butyl paraben 19,20 and benzoic acid−sodium benzoate cocrystal formation. 21 Couette and Taylor introduced the Taylor vortex flow in 1890−1923. 22,23 Subsequently, this novel approach was adapted and extended.…”

Section: Introductionmentioning

confidence: 99%

Influence of Taylor Vortex Flow on the Crystallization ofl-Glutamic Acid as an Organic Model Compound

Trinh

Nguyen

Khuu

et al. 2022

Ind. Eng. Chem. Res.

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The mechanism of polymorph selection is still not fully understood in crystallization. This study demonstrates the impact of Taylor vortex flow on the crystallization and polymorph selection of l-glutamic acid as an organic model compound. Our results show that amorphous intermediates preceded the formation of a crystalline phase. The morphology of these amorphous precursorsranging from spherical, oval, and ellipsoidal to irregular shapeswas governed by the velocity of the Taylor vortex flow. We attribute this observation to a transient liquidlike state of the amorphous precursor; simulations indeed corroborated this assumption as the morphology of droplets of a liquidlike precursor varies with the velocity of fluid motion accordingly. The phase selectivity depended on the intensity of the Taylor vortex flow. We found that the metastable α-form crystallized at low Taylor numbers, whereas the thermodynamically stable β-form was obtained at high Taylor numbers, suggesting an impact of Taylor vortex flow on the amorphous-to-crystalline rearrangement of the intermediates. Moreover, a critical value of the Taylor number as Ta ∼ 3636 was determined, which triggered the fast formation of the β-polymorph. We assume that the high shear rate and mass transfer of Taylor vortex flow facilitate the phase transformation from the α- to the β-polymorph.

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“…Despite its obvious benefits, SBRC seems to be a very obscure technique, as only few studies on the formation of cocrystals in this fashion have been published. SBRC in its most literal sense has been carried out by Chen et al 44 Here, the cocrystallization was induced by partially neutralizing sodium benzoate with HCl. The obtained benzoic acid then cocrystallized with the remaining sodium benzoate.…”

Section: ■ Introductionmentioning

confidence: 99%

Semibatch Reaction Crystallization for Scaled-Up Production of High-Quality CL-20/HMX Cocrystal: Efficient Because of Solid Dosing

Herrmannsdörfer

Klapötke

2021

Crystal Growth & Design

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CL-20/HMX cocrystal is one of the most promising energetic cocrystals, but scaled-up production was prevented by the large inherent solubility difference of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20) and 1,3,5,7-tetranitro-1,3,5,7-tetrazoctane (HMX) and, therefore, unacceptable CL-20 efficiency. Reaction cocrystallization (aka. reaction crystallization or slurry technique) has been extensively used as an efficient, straightforward cocrystallization screening method, but only few attempts at utilizing this method for scaled-up cocrystal production have been undertaken and none have realized its full potential. By utilizing solid dosing and process analytical technology, semibatch reaction cocrystallization (SBRC) provided the first scale-up of high-quality CL-20/HMX cocrystal with a particle diameter D(4,3) of 163 μm and a batch size of 100 g. The CL-20 recovery is 63%, which is over two times better than the theoretical recovery rate of the next best method (evaporation crystallization), and the crystal quality is comparable to crystals obtained from controlled antisolvent crystallization. It is shown that SBRC is a valuable crystallization technique for efficient scale-up of cocrystal systems whose coformers exhibit significantly different solubilities.

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Mixing Effect on Stoichiometric Diversity in Benzoic Acid–Sodium Benzoate Cocrystals

Cited by 7 publications

References 35 publications

Co-Crystallization Kinetics of 2:1 Benzoic Acid–Sodium Benzoate Co-Crystal: The Effect of Templating Molecules in a Solution

Co-Crystallization Kinetics of 2:1 Benzoic Acid–Sodium Benzoate Co-Crystal: The Effect of Templating Molecules in a Solution

Influence of Taylor Vortex Flow on the Crystallization ofl-Glutamic Acid as an Organic Model Compound

Semibatch Reaction Crystallization for Scaled-Up Production of High-Quality CL-20/HMX Cocrystal: Efficient Because of Solid Dosing

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