Purification of hydrobenzoin enantiomers by stripping crystallization

Shiau, Lie‐Ding; Liu, Keng-Fu; Huang, Pin-Hao

doi:10.1016/j.jtice.2013.01.020

Cited by 2 publications

(2 citation statements)

References 8 publications

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“…As an ascendant separation unit, efficient and simpler both in process and equipment than conventional crystallization , SC has been used for the preparation or purification of many solid products. For example, in addition to the substances mentioned above, cresol isomers , S ‐ibuprofen , hydrobenzoin enantiomers , benzene , and 4‐methoxyphenol have also been purified by stripping crystallization.…”

Section: Research Progress Of Each Single Unit In the Hybrid Distillamentioning

confidence: 99%

Research Progress of Hybrid Distillation/Crystallization Technology

Zhou

et al. 2018

Chem Eng & Technol

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The hybrid distillation/crystallization process is successfully applied to separate azeotropes and closely boiling mixtures. This process can not only provide pure products, but also allow for significant energy savings. The research progress and industrial applications of hybrid distillation/crystallization are reviewed. Different sequences of hybrid distillation/crystallization process are presented based on the optimized design. The specific developments of each single unit, namely, distillation and crystallization, in the hybrid process are outlined. Applications of hybrid distillation/crystallization in practical cases are highlighted and analyzed. Finally, the key issues and perspectives for further research of this integrated process are illustrated.

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Section: Research Progress Of Each Single Unit In the Hybrid Distillamentioning

confidence: 99%

Research Progress of Hybrid Distillation/Crystallization Technology

Zhou

et al. 2018

Chem Eng & Technol

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“…27 Traditionally, enantioselective membranes are fabricated using enantioselective carriers, chiral selectors, entrapped enzymes, or proteins, while several limitations or disadvantages include slow mass transport, low enantioselectivity, and poor stability associated with the membranes. 28 Although there are some other methods to achieve enantiomeric separation, for example, stripping crystallization 29,30 and self-disproportionation of enantiomers, 31 they do not work with racemic mixtures. Despite the availability of those chiral resolution methods, it is still difficult to resolve or separate enantiomers.…”

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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Purification of hydrobenzoin enantiomers by stripping crystallization

Cited by 2 publications

References 8 publications

Research Progress of Hybrid Distillation/Crystallization Technology

Research Progress of Hybrid Distillation/Crystallization Technology

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

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