Triacetylcellulose as a chiral stationary phase for high-performance liquid chromatography

Isaksson, Roland; Erlandsson, Per; Hansson, Lennart; Holmberg, Ann; Berner, Sissi

doi:10.1016/s0021-9673(01)84257-6

Cited by 60 publications

(19 citation statements)

References 27 publications

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“…This counter-current dissolution will cause the loss of crystallinity of the movement is simulated by an appropriated flow adsorbent structure. The microcrystalline structure of switching sequence: the adsorbent bed is divided into this adsorbent will determine the geometric arrangea number of fixed-bed columns, while the inlet and ment of the chiral environment [1,[6][7][8][9].…”

Section: Introductionmentioning

confidence: 99%

Separation of enantiomers of a chiral epoxide by simulated moving bed chromatography

Pais

Loureiro

Rodrigues

1998

Journal of Chromatography A

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The paper deals with chiral separation by simulated moving bed (SMB) chromatography. The separation of chiral epoxide enantiomers in microcrystalline cellulose triacetate using methanol as eluent is considered as illustrative example. The use of microcrystalline cellulose triacetate for the chromatographic separation of enantiomers is first reviewed and a methodology for obtaining basic data (adsorption equilibrium isotherms, axial dispersion and mass transfer coefficient) is discussed. A model for the prediction of the cyclic steady-state performance of the SMB, based on the analogy with the true moving bed, is developed assuming multicomponent adsorption equilibria, axial dispersion flow and linear driving force approximation to describe the intraparticle mass transfer rate. The simulation package is used to predict the effect of operating variables on the process performance and to define the regions for enantiomer separation. A simple optimization procedure is proposed for choosing the best SMB operating conditions. This procedure is extensively tested for the separation of chiral epoxide enantiomers. The experimental operation of a SMB pilot unit was carried out for this system. Purities and recoveries higher than 90% were obtained for both extract and raffinate, using a 420 ml inventory of stationary phase. The SMB pilot allows the continuous resolution of 52 g of racemic mixture per day and per liter of bed, with a solvent consumption of 0.4 l of mobile phase per gram of racemic mixture processed. The simulation package is also used to predict the steady-state internal concentration profiles for the SMB operation with reasonable agreement with experimental results.

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Section: Introductionmentioning

confidence: 99%

Separation of enantiomers of a chiral epoxide by simulated moving bed chromatography

Pais

Loureiro

Rodrigues

1998

Journal of Chromatography A

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“…The best results were obtained when the substituent group was in the 3 position; eg 4-benzyl-3-propionyl-(a = 1.70) and, on MCTA columns, 3-isopropyl-5-p-(2-methoxyethyl)phenyloxymethyl-and 3-isopropyl-5-(anaphtyl)oxymethyl-2-oxazolidinone (a = 1.84 and a = 1.39, respectively; Isaksson and Lamm, 1986). In this case the N-carbonyl group in 3 position does not appear to be essential for chiral recognition.…”

Section: Mcta Layersmentioning

confidence: 99%

“…Efficient analytical procedures for the separation of enantiomers and the control of their optical purity need to be developed since many physiologically important compounds are chiral molecules (Isaksson et al, 1990).…”

Section: Introductionmentioning

confidence: 99%

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Reversed‐phase planar chromatography of some enantiomeric amino acids and oxazolidinones

Lepri

Boddi

Bubba

et al. 2001

Biomedical Chromatography

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The resolution of two enantiomeric amino acids and four structurally related oxazolidinones was evaluated by reversed-phase planar chromatography using both home-made microcrystalline cellulose triacetate (MCTA) layers and mobile phase additivies, such as beta-cyclodextrins (beta-Cy), modified alpha, beta, gamma cyclodextrins and bovine serum albumin (BSA), on commercially available RP-18W/F254 and SilC18-50/UV254 plates. All the enantiomers were partially or baseline resolved by at least one of the chiral phases tested. Densitograms of optical antipodes and their mixtures were measured on MCTA layers developed with hydroalcoholic solvents.

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“…The last decade has seen the commercialization of a large number of chiral stationary phases (CSP) including cyclodextrin (Armstrong and DeMond, 1984;Ward and Armstrong, 1988), interaction (Pirkle et al, 1982;Pirkle and Murray, 1990), protein (Hermansson and Eriksson, 1986;Schill et al, 1986), cellulosic and amylosic phases (Okamoto et al, 1988;Isaksson et al, 1990). The importance of carbohydrates to chiral recognition may be inferred not only from the enantioselectivities exhibited by cyclodextrin-, amylosic-and cellulosic-derived phases but also the fact that two of the protein CSP, the ␣ 1 -acid glycoprotein and the ovomucoid phases, incorporate significant carbohydrate moieties (Iredale et al, 1991).…”

Section: Introductionmentioning

confidence: 99%

Separation of benzodiazepines on a new carbohydrate-based chiral stationary phase for HPLC

Stalcup

Williams

1997

Biomed. Chromatogr.

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Triacetylcellulose as a chiral stationary phase for high-performance liquid chromatography

Cited by 60 publications

References 27 publications

Separation of enantiomers of a chiral epoxide by simulated moving bed chromatography

Separation of enantiomers of a chiral epoxide by simulated moving bed chromatography

Reversed‐phase planar chromatography of some enantiomeric amino acids and oxazolidinones

Separation of benzodiazepines on a new carbohydrate-based chiral stationary phase for HPLC

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