Comparison of liquid and supercritical fluid chromatography mobile phases for enantioselective separations on polysaccharide stationary phases

Khater, Syame; Lozac'h, Marie-Anne; Adam, Isabelle; Francotte, Eric; West, Caroline

doi:10.1016/j.chroma.2016.06.060

Cited by 60 publications

(40 citation statements)

References 29 publications

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“…The temperature can affect the elution strength and mobile phase viscosity and thus allows achieving very high efficiency. Detailed descriptions of various effects of the separation system variables and their consequences for the separation performance in SFC can be found in papers and reviews by the group of West and Lesellier [5,[19][20][21][22][23].…”

Section: Introductionmentioning

confidence: 99%

Cellulose tris‐(3,5‐dimethylphenylcarbamate)‐based chiral stationary phase for the enantioseparation of drugs in supercritical fluid chromatography: comparison with HPLC

Kalíková

Martínková

Schmid

et al. 2018

J of Separation Science

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A cellulose tris-(3,5-dimethylphenylcarbamate)-based chiral stationary phase was studied as a tool for the enantioselective separation of 21 selected analytes with different pharmaceutical and physicochemical properties. The enantioseparations were performed using supercritical fluid chromatography. The effect of the mobile phase composition was studied. Four different additives (diethylamine, triethylamine, isopropylamine, and trifluoroacetic acid) and isopropylamine combined with trifluoroacetic acid were tested and their influence on enantioseparation was compared. The influence of two different mobile phase co-solvents (methanol and propan-2-ol) combined with all the additives was also evaluated. The best mobile phase compositions for the separation of the majority of enantiomers were CO /methanol/isopropylamine 80:20:0.1 v/v/v or CO /propan-2-ol/isopropylamine/trifluoroacetic acid 80:20:0.05:0.05 v/v/v/v. The best results were obtained from the group of basic β-blockers. A high-performance liquid chromatography separation system composed of the same stationary phase and mobile phase of similar properties prepared as a mixture of hexane/propan-2-ol/additive 80:20:0.1 v/v/v was considered for comparison. Supercritical fluid chromatography was found to yield better results, i.e. better enantioresolution for shorter analysis times than high-performance liquid chromatography. However, examples of enantiomers better resolved under the optimized conditions in high-performance liquid chromatography were also found.

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Section: Introductionmentioning

confidence: 99%

Cellulose tris‐(3,5‐dimethylphenylcarbamate)‐based chiral stationary phase for the enantioseparation of drugs in supercritical fluid chromatography: comparison with HPLC

Kalíková

Martínková

Schmid

et al. 2018

J of Separation Science

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“…Shi et al found that the separation of enantiomers of methyl mandelate was satisfactory by means of gas chromatography using β‐cyclodextrin (CyclodexB, 30 m × 0.25 mm × 0.25 μm). Comparing supercritical fluid chromatography (SFC) with HPLC, first, CO 2 is more easily available and less expensive as the mobile phase of SFC; second, only a small amount of polar modifier is added, which has less impact on the environment and operators; in addition, SFC can expand the range of chromatographic analysis by using a variety of detectors, such as UV detector, electron capture detector, and so forth . This leads to the complementarity in the separation of different target compounds .…”

Section: Introductionmentioning

confidence: 99%

“…Comparing supercritical fluid chromatography (SFC) with HPLC, first, CO 2 is more easily available and less expensive as the mobile phase of SFC; second, only a small amount of polar modifier is added, which has less impact on the environment and operators 10 ; in addition, SFC can expand the range of chromatographic analysis by using a variety of detectors, such as UV detector, 11 electron capture detector, and so forth. 12 This leads to the complementarity in the separation of different target compounds. 13 Supercritical fluid chromatography takes the advantages of short analysis time, fast column equilibration, and simple mobile phase system.…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation of chiral mandelic acid derivatives by supercritical fluid chromatography

et al. 2018

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Mandelic acid and its derivatives are important chiral analogs which are widely used in the pharmaceutical synthetic industry. The present study investigated the enantiomeric separation of six mandelic acids (mandelic acid, 2‐chloromandelic acid, 3‐chloromandelic acid, 4‐chloromandelic acid, 4‐bromomandelic acid, 4‐methoxymandelic acid) on the Chiralpak AD‐3 column by supercritical fluid chromatography. The influences of volume fraction of trifluoroacetic acid, type and percentage of modifier, column temperature, and backpressure on the separation efficiency were investigated. And the enantiomer elution order was determined. The results show that, for a given modifier, the retention factor, the separation factor, and the separation resolution decreased gradually with increasing the volume ratio of the modifier. At the same volume ratio of modifier, the retention factor of the mandelic acid and its derivatives increased in the order of methanol, ethanol, and isopropanol, except 3‐chloromandelic acid. The separation factor and the separation resolution decreased with the increase of column temperature (below the temperature limit). The backpressure affected the enantioseparation process: As the backpressure increased, a corresponding decrease in retention factor was observed. Under the same chiral column conditions, the SFC method exhibited faster and more efficient separation with better enantioselectivity than the HPLC method.

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“…Chromatographic methods are most popular, including high-performance liquid chromatography (HPLC), gas chromatography, capillary electrochromatography, thin-layer chromatography, and supercritical fluid chromatography (SFC). [7][8][9] However, there have been relatively few studies on the application of this method for the separation of chiral pesticides. 4,5 In comparison with HPLC, the low viscosity and high diffusivity of supercritical fluid allow much higher flow rates, thereby leading to shorter analysis time, lower solvent consumption, and higher efficiency.…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation of napropamide by supercritical fluid chromatography: Effects of the chromatographic conditions and separation mechanism

et al. 2018

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Supercritical fluid chromatography (SFC) is already used for enantioseparation in the pharmaceutical industry, but it is rarely used for the separation of chiral pesticides. Comparing with high performence liquid chromatography, SFC uses much more environmnetal friendly and economic mobile phase, supercritical CO . In our work, the enantioseparation of an amide herbicide, napropamide, using three different polysaccharide-type chiral stationary phases (CSPs) in SFC was investigated. By studying the effect of different CSPs, organic modifiers, temperature, back-pressure regulator pressures, and flow rates for the enantioseparation of napropamide, we established a rapid and green method for enantioseparation that takes less than 2 minutes: The column was CEL2, the mobile phase was CO with 20% 2-propanol, and the flow rate was 2.0 mL/min. We found that CEL2 demonstrated the strongest resolution capability. Acetonitrile was favored over alcoholic solvents when the CSP was amylose and 2-propanol was the best choice when using cellulose. When the concentration of the modifiers or the flow rate was decreased, resolutions and analysis times increased concurrently. The temperature and back-pressure regulator pressure exhibited only minor influences on the resolution and analysis time of the napropamide enantioseparations with these chiral columns. The molecular docking analysis provided a deeper insight into the interactions between the enantiomers and the CSPs at the atomic level and partly explained the reason for the different elution orders using the different chiral columns.

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Comparison of liquid and supercritical fluid chromatography mobile phases for enantioselective separations on polysaccharide stationary phases

Cited by 60 publications

References 29 publications

Cellulose tris‐(3,5‐dimethylphenylcarbamate)‐based chiral stationary phase for the enantioseparation of drugs in supercritical fluid chromatography: comparison with HPLC

Cellulose tris‐(3,5‐dimethylphenylcarbamate)‐based chiral stationary phase for the enantioseparation of drugs in supercritical fluid chromatography: comparison with HPLC

Enantioseparation of chiral mandelic acid derivatives by supercritical fluid chromatography

Enantioseparation of napropamide by supercritical fluid chromatography: Effects of the chromatographic conditions and separation mechanism

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