Additive-assisted preferential crystallization of racemic component: A case of norvaline

Sun, Jie; Wang, Yaping; Gao, Zhenguo; Gong, Junbo; Tang, Weiwei

doi:10.1016/j.jiec.2022.02.054

Cited by 10 publications

(7 citation statements)

References 35 publications

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“…This means that adding these molecules probably did not change the kinetic driving force, supersaturation. Similar conclusions can be drawn from some reports. ,,, …”

Section: Effect Of Tmas On Crystal Nucleationsupporting

confidence: 90%

“…Similar conclusions can be drawn from some reports. 5,33,54,55 However, some special cases should be noted. Some studies have shown that TMAs increased the solubility to varying degrees by promoting the self-association of solute molecules 56,57 or changing the pH of the solution system.…”

Section: Tmas Affect Nucleation By Acting On Solubilitymentioning

confidence: 99%

“…Only pure D-crystals were precipitated from the solution via precisely controlling the amount of L-additives in the solution or combining the circulation crystallization technology. Sun et al 55 successfully resolved norvaline, a racemate compound, by coupling preferential crystallization with a TMA. This could meet the requirements of chiral separation in terms of purity and yield.…”

Section: Process Optimization For Chiral Resolutionmentioning

confidence: 99%

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Role of Tailor-Made Additives in Crystallization from Solution: A Review

Zhu

Gao

et al. 2023

Ind. Eng. Chem. Res.

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Additives which share a similar molecular structure with the crystallizing parent molecule are called tailor-made additives (TMAs). The inclusion of well-chosen TMAs often has a significant impact on crystallization behaviors. However, how TMAs affect the solution crystallization has seldom been systematically summarized in recent years. Herein this paper reviews the role of TMAs in solution crystallization. First, the effects and action mechanisms of TMAs on crystal nucleation and growth are discussed, respectively. Next, the applications of TMAs in the regulation of crystal properties including the polymorphism, crystal habit, crystal size, and chirality are introduced. Then the recent progress of molecular simulation in predicting the role of TMAs is discussed. Finally, we analyze the existing problems in this field and give an outlook on the future development. This paper is helpful and useful to readers interested in the use of TMAs to control crystallization and design crystals with desired properties.

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“…This means that adding these molecules probably did not change the kinetic driving force, supersaturation. Similar conclusions can be drawn from some reports. ,,, …”

Section: Effect Of Tmas On Crystal Nucleationsupporting

confidence: 90%

Section: Tmas Affect Nucleation By Acting On Solubilitymentioning

confidence: 99%

Section: Process Optimization For Chiral Resolutionmentioning

confidence: 99%

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Role of Tailor-Made Additives in Crystallization from Solution: A Review

Zhu

Gao

et al. 2023

Ind. Eng. Chem. Res.

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“…16,17 Preferential crystallization (PC), 18,19 diastereomeric salt formation, 20 and diastereomeric cocrystallization 21,22 are crystallization-based methods for chiral resolution. PC is commonly achieved by seeding with the desired enantiomer or with the assistance of additives 23 and temperature cycling, 24 but it is restricted to racemic conglomerates (only accounting for 5−10% of the racemic mixtures) or slowly crystallizing racemic compounds 25 with a low yield in a single batch process when racemization is absent.…”

Section: ■ Introductionmentioning

confidence: 99%

Green and Strategic Approach for Chiral Resolution by Diastereomeric Salt Formation: The Study of Racemic Ibuprofen

Lee

Hung

Amin

et al. 2023

Ind. Eng. Chem. Res.

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As diastereomeric salt formation is the most popular method for the industrial preparation of single enantiomers, this method is chosen to resolve enantiomers of ibuprofen (IBU) in the present study. This type of chiral resolution process involves three steps: formation of a diastereomeric salt pair of racemic ibuprofen (Rac-IBU) with a chiral resolving agent, (S)-(−)-α-methylbenzylamine (S-MBA) in the presence/absence of a nonchiral agent, potassium hydroxide (KOH), resolution by cooling crystallization in a common solvent, and recovery of the compound with one enriched enantiomer. The present study is to investigate each of the three steps individually toward the chiral resolution of S-IBU, including the effects of (1) equivalent ratio of Rac-IBU-to-S-MBA-to-KOH on diastereomeric excess (%de) and yield upon the formation of the diastereomeric salts, (2) solvent and (3) temperature range for cooling crystallization on %de and yield upon the resolution by cooling crystallization, (4) solvent-to-antisolvent ratio, (5) aging time, and (6) addition rate of antisolvent on enantiomeric excess (%ee) and yield upon the recovery of the S-enriched IBU. Each step is optimized, and the integrated chiral resolution process is scaled up to a 0.5 L scale. Furthermore, practical guidelines are suggested for the future development of chiral resolution processes by diastereomeric salt formation.

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“…Additive-assisted crystallization is one of the most intriguing approaches allowing one to regulate the crystallization and polymorphic output. − Indeed, “tailor-made” additives were previously used for the crystal engineering of bioactive and pharmaceutical compounds. − The presence of even minute amounts of impurities may affect the kinetic and thermodynamic parameters of the crystallization process . The kinetic factors are responsible for crystal nucleation, growth, and dissolution, but the exact working mechanism of impurities on the molecular level is still not fully understood.…”

Section: Introductionmentioning

confidence: 99%

Additive-Assisted Perylene Polymorphism Controlled via Secondary Bonding Interactions

Sonina

Kuimov

Shumilov

et al. 2023

Crystal Growth & Design

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The influence of molecular additives or impurities on crystal growth, morphology, and polymorphism has broad importance in various fields of material science and pharmaceutical engineering. There are numerous examples demonstrating the effect of impurities on the crystallization of pharmaceutical substances; however, systematic studies on the additives' effect on crystallization and properties of organic semiconductors have not yet been reported. Here, we studied additive-assisted crystallization of a model aromatic hydrocarbon compound−perylene−to elaborate the crystal engineering tool for organic optoelectronics and to reveal the underlying mechanism. Anthracene, tetracene, 9,10diphenylanthracene, and rubrene were used as representative additives. We found the optimal additive and conditions for perylene crystallization allowing us to control its polymorphic outcome. The addition of 9,10-diphenylanthracene was demonstrated to lead to a preferable crystallization of metastable β-form of perylene, whereas in the neat conditions, α-form was typically obtained as a stable one. The crystallization of perylene with 9,10diphenylanthracene in high concentrations resulted in their stoichiometric co-crystallization. The perylene:9,10-diphenylanthracene co-crystal structure and optoelectronic properties were evaluated. The co-crystal demonstrated a photoluminescence quantum yield of 45% and hole mobility of 0.025 cm 2 /V s. The co-crystal structure analysis pointed on the stabilization of herringbone packing of perylene by interlayer C−H•••π interactions, allowing the 9,10diphenylanthracene layers to serve as the template for perylene β-polymorph nucleation. The results obtained could serve as the basis for crystallization control and engineering of high-performance materials in organic optoelectronics.

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Additive-assisted preferential crystallization of racemic component: A case of norvaline

Cited by 10 publications

References 35 publications

Role of Tailor-Made Additives in Crystallization from Solution: A Review

Role of Tailor-Made Additives in Crystallization from Solution: A Review

Green and Strategic Approach for Chiral Resolution by Diastereomeric Salt Formation: The Study of Racemic Ibuprofen

Additive-Assisted Perylene Polymorphism Controlled via Secondary Bonding Interactions

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