Scale‐up of analytical chromatography to the simulated moving bed separation of the enantiomers of the flavour norterpenoids α‐ionone and α‐damascone

Zenoni, Gianmarco; Quattrini, Francesca; Mazzotti, Marco; Fuganti, Claudio; Morbidelli, Massimo

doi:10.1002/ffj.1088

Cited by 30 publications

(12 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The HPLC‐SMB unit used in this work has been described previously (Pedeferri et al, 1999; Zenoni et al, 2002). It consists of eight HPLC columns (12.5 × 1 cm) packed with the stationary phase Nucleodex®‐β‐PM of particle diameter 10 μm from Macherey‐Nagel (Düren, Germany).…”

Section: Methodsmentioning

confidence: 99%

“…Note that since, in this system, the desorbent is not recycled and always fed fresh, this unit behaves like a closed‐loop system with the same number of columns in the first three sections, and operated in such a way that the desorbent is fully regenerated in section 4, that is, pure desorbent is recycled back to the unit. The bed void fraction is ε* = 0.62 (Zenoni et al, 2002). The extra‐column dead volumes V

_{italicj}^{italicD}

were measured to be 0.605, 2.788, 1.150, and 1.696 mL for each column in section 1, 2, 3, and 4, respectively.…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Experimental assessment of powerfeed chromatography

Zhang¹,

Morbidelli²,

Mazzotti

2004

AIChE Journal

Self Cite

View full text Add to dashboard Cite

show abstract

Section: Methodsmentioning

confidence: 99%

_{italicj}^{italicD}

were measured to be 0.605, 2.788, 1.150, and 1.696 mL for each column in section 1, 2, 3, and 4, respectively.…”

Section: Methodsmentioning

confidence: 99%

Experimental assessment of powerfeed chromatography

Zhang¹,

Morbidelli²,

Mazzotti

2004

AIChE Journal

Self Cite

View full text Add to dashboard Cite

show abstract

“…Enantioseparation of a racemic mixture is the most abundant strategy in industry . There are various separation methods, such as crystallization, kinetic resolution, capillary electrophoresis, membrane technology, simulated moving bed chromatography and enantioselective liquid–liquid extraction . Due to low versatility and excessive solids handling of crystallization with a maximum yield of 50%, the low transport rate and the risk of fouling in membrane technology, and the high cost of simulated moving bed chromatography, enantioselective liquid–liquid extraction seems a potentially attractive technique which is cheaper and easier to scale up to commercial scale and has a large application range .…”

Section: Introductionmentioning

confidence: 99%

Enantioselective liquid–liquid extraction of (D, L)‐valine using metal–BINAP complex as chiral extractant

Tang

2013

J of Chemical Tech & Biotech

View full text Add to dashboard Cite

Background Enantioselective liquid–liquid extraction is a very attractive technology for the production of enantiomerically pure compounds. The objective of this research is to investigate enantioselective liquid–liquid extraction of valine (Val) enantiomers with metal–BINAP complexes as enantioselective extractants. Results Results show that BINAP complex with copper(I) as central ion allows the separation of Val enantiomers with the highest operational selectivity. Efficiency of the extraction depends, often strongly, on a number of process variables, including types of organic solvents, pH of the aqueous phase, concentration of host and substrate, and temperature. Extraction performance of the system can be accurately predicted by the model. By modeling and experiment, an optimal extraction condition was obtained at a pH of 8 and the host concentration of 2.0 × 10‐3 mol L‐1 with the highest enantioselective (α) of 3.65 and performance factor (pf) of 0.086. Conclusions The presented data indicate that Val enantiomers can be efficiently separated by enantioselective liquid–liquid extraction. The model provides a powerful tool for calculating distribution ratio, enantioselectivity, enantiomeric excess and performance factor. It can be used for optimization of the reactive extraction systems. This paper can provide some valuable fundamental data for the production of enantiomerically pure amino acid enantiomers. © 2013 Society of Chemical Industry

show abstract

“…12 Some impressive preparative chiral separations have been demonstrated using centrifugal partition chromatography 13 and simulated moving bed chromatography. 14,15 Another strategy for chiral separations is based on the use of membrane-based approaches. [16][17][18][19][20] When applying immobilized selectors in (liquid) membranes, the amount of selector needed can be reduced greatly.…”

Section: Single Enantiomers Drugsmentioning

confidence: 99%

Enantioseparation of D- and L- isomers of Chiral Drugs for Improving their Bioavailability: Some Techniques Including Micellization with Gemini Surfactants

Singh¹,

Sharma²

2018

IJPER

View full text Add to dashboard Cite

The enantiopure drugs are essential for disease treatment as the human body is amazingly chiral selective. Nearly 50% of drugs are chiral but the pharmacological activity resides with only one isomer, termed as eutomer, whereas the other isomer which is inactive or less potent metabolizes by a different way in the body. This toxic isomer in a racemic drug causes side-effects, genetic disorder or may cause even death if taken in high dosage. Therefore, role of stereochemistry in drug action getting more and more attention of medical practice and one should be good knowledge to make decisions regarding while using single enantiomer of any drug. Most of the drugs used in psychiatric practice are currently available in mixture of enantiomers. For some therapeutics, one particular isomer of chiral drug give better pharmacological results with respect to the target organ, bioavailability in body plasma, low toxicity etc., as compared to racemic mixture of that drug. This article explains the chirality of drugs, the stereochemistry of isomers of chiral drugs, emphasizes the difference in the potential biological and pharmacologic differences between the two enantiomers of a drug, and highlights the novel technique to increase the in-vivo solubility of particularly one isomer of drug, so that the bioavailability of eutomer can be enhanced. This can be done by used of surfactants, which encapsulate the enantiomers of drugs at different extend by micellization.

show abstract

Scale‐up of analytical chromatography to the simulated moving bed separation of the enantiomers of the flavour norterpenoids α‐ionone and α‐damascone

Cited by 30 publications

References 33 publications

Experimental assessment of powerfeed chromatography

Experimental assessment of powerfeed chromatography

Enantioselective liquid–liquid extraction of (D, L)‐valine using metal–BINAP complex as chiral extractant

Enantioseparation of D- and L- isomers of Chiral Drugs for Improving their Bioavailability: Some Techniques Including Micellization with Gemini Surfactants

Contact Info

Product

Resources

About