New 3-Micron Polysaccharide-based Chiral Columns for Fast HPLC and SFC Geoffrey B. Cox, Norbert M. Maier Chiral Technologies, Inc
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1 New 3-Micron Polysaccharide-based Chiral Columns for Fast HPLC and SFC Geoffrey B. Cox, Norbert M. Maier Chiral Technologies, Inc Pilar Franco and Tong Zhang Chiral Technologies, Europe
2 Benefits of 3-Micron Columns High Speed separations Reduction in analysis time More samples per day Reduction in cost per sample High efficiency separations Higher resolution for difficult samples Higher precision from higher resolution
3 Why Stop at 3-Microns? Pressure 3-Micron columns give attainable pressure drops at high flow rate Pressure increases dramatically with smaller particles [ΔP = f(1/d p2 )] Equipment Conventional HPLC systems cannot reach the high pressures needed for very small particles Conventional HPLC systems need modification for very small particles
4 R s / Time (min) Pressure (bar) Pressure, R s and Particle Size DP Time R s dp Calculated for methanol at the optimum flow velocity for each particle
5 Effect of Equipment on Performance CHIRALPAK Agilent 12 SL Agilent 11 Relative Loss AD -3 (ECV optimized) (standard) (%) Column Size N 1 N 2 N 1 N 2 N 1 N 2 25 x 4.6 mm I.D x 4.6 mm I.D x 4.6 mm I.D (Trifluorophenylethanol; n-hexane/2-propanol 9:1; 1 ml/min, 21 nm, 25 C) The 3-Micron columns may be used in conventional (but modern) HPLC units without significant loss in performance, even with the smaller columns. With older units, small volume flow cells and narrow diameter capillaries may be needed for optimum performance.
6 Reduction in Particle Size Gives Faster Mass Transfer 2.5-Microns Bandwidth due to pore diffusion 1.5-Microns This effect increases with flow velocity
7 HETP (mm) Van Deemter Plots: 3- vs 5-Microns micron CHIRALPAK AD-H CHIRALCEL AD-3 CHIRALPAK IC -3 CHIRALPAK IA -3 9:1 Hexane : IPA trans-stilbene xide Higher optimum flow rate with smaller particles leads to faster analyses and higher efficiency Smaller HETP allows shorter columns and faster analyses.5 3-Micron Flow Velocity (mm/sec)
8 HETP (mm) Van Deemter Plots Reversed Phase Mobile phase: Water-Acetonitrile 6:4 (v/v) Detection: 21 nm Temp.: 25 C Sample volume: 1. microl.25 1-Indanol, 1st Enantiomer Micron CHIRALPAK AD-3R.1 CHIRALPAK AD-3R CHIRALPAK AD-RH.5 3-Micron u (mm/s)
9 2.252 Reversed Phase Tests AD-3R CHIRALPAK AD-3R 15 x 4.6 mm 4% ACN.2M KH 2 P 4.5 ml/min; 25 C 5 1 N1 N Mephenesin (1) Indanol (2) Naphthylethanol (3) Methyl-1-tetralone (4) min After 3 week pressure stability test
10 CHIRALPAK IA (5µm) CHIRALPAK IC (5µm) Selectivity: Transfer From 5-Micron y = 1.367x R 2 = y =.9948x R 2 = CHIRALPAK IA-3 (3µm) CHIRALPAK IC-3 (3µm) Effortless method transfer from 5- to 3-Micron columns
11 k CHIRALPAK IA (5µm) CHIRALPAK IA (5µm) Retention Factors: Transfer from 5-Micron k CHIRALPAK IA-3 (3µm) CHIRALPAK IA-3 (3µm) Effortless method transfer from 5- to 3-Micron columns
12 Transfer to 3-Micron: CHIRALPAK IA-3 mau CHIRALPAK IA (15 x 5.6 mm I.D., 5 mm) Hexane-Isopropanol 9:1 (v/v) UV 21 nm, 25 C flow rate:.6 ml/min * ~ Equal plate numbers 2 N = 18, min mau CHIRALPAK IA-3 (15 x 5.6 mm I.D., 3 mm) Hexane-Isopropanol 9:1 (v/v) UV 21 nm, 25 C flow rate: 1.75 ml/min N = 23, 7 Mecoprop methyl ester: 1,2 trans-stilbene oxide: 3,7 Benzoin ethyl ether: 4,5 Ruelene: 6, min 4 3-fold faster
13 Transfer to 3-Micron: CHIRALPAK IC-3 mau CHIRALPAK IC-5 (15 x 5.6 mm I.D., 3 mm) hexane/2-propanol 9:1 (v/v) UV 21 nm, 25 C flow rate:.6 ml/min 3 4 * ~ Equal plate numbers 2 1 N = 19, min mau 5 4 CHIRALPAK IC-3 (15 x 5.6 mm I.D., 3 mm) Hexane-Isopropanol 9:1 (v/v) UV 21 nm, 25 C flow rate: 1.75 ml/min Phenyl-2,2,2-trifluoroethanol: 1,2 Tetrahydronaphthol: 3,4 Mecoprop methyl ester: 5,6 3 2 N = 21, fold faster
14 High Efficiency Separations - Metolochlor N CH 3 Cl 2 x CHIRALCEL D-3 (15 x 4.6 mm I.D.) R s1,2 2.2 R s3, N N N3 196 N min Serial coupled columns, n-hexane/2-propanol 97.5:2.5 (v/v);.5 ml/min; 235 nm; 15 C
15 CHIRALPAK IA-3 (4.6 x 15 mm) High Speed Separations Cl Cl N N Furoin H Cl min min MtBE-MeH 8:2 (+.1% Ethanolamine) Flow rate: 3.5 ml/min MeH 1% Flow rate: 3. ml/min
16 Pressure Stability For high speed separations, the columns must be pressure stable Extensive pressure testing of the 3-Micron columns shows no practical limit with conventional HPLC systems
17 operational pressure (bar) Pressure Stability 5 4 Column: CHIRALPAK AD-3 (15 x 4.6 mm I.D.) pressurizing solvent: ethanol; stress test performed without guard cartridge ml/min EtH 43 bar operation pressure for 1 week total volume of mobile phase passing through column 23 L (= 14,5 column volumes) exposure time (days) Test EtH 1 Test EtH 2 Test EtH 3 Test EtH 4 Test EtH 5 Test Hex 1 Test Hex 2
18 Column Tests Pressure Stability mau TS Ethanol:.5 ml/min Before min Column: CHIRALPAK AD-3 (15 x 4.6 mm I.D.) mau After min 2 Compound QC-Test N unchallenged N after stress N Diff (%) N1 N2 N1 N2 N1 N2 TS/Ethanol Test EtH Troeger base Hexane / IPA Test EtH TS Hexane/IPA Test Hex
19 Fast Separations N H H N Cl CH xprenolol.hcl Cl Dichlorprop Cl Carbinoxamine N seconds seconds seconds CHIRALPAK AD-3 (5 x 4.6 mm I.D.); for oxprenolol and carbinoxamine: n-hexane/ 2-propanol/diethylamine 9/1/.1 (v/v/v); for dichlorprop: n-hexane/2-propanol/trifluoroacetic acid 9/1/.1 (v/v/v); flow rate: 5. ml/min; UV-detection: 235 nm; temperature: 25 C.
20 Reversed Phase CHIRALPAK AD-3R (4.6 x 15 mm) Tolperisone.2M NH 4 HC 3 aq. (ph9. -DEA) ACN 4:6 Methyl 2-phenylsulfinylacetate H 2 -ACN 6:4 N S
21 mv mv SFC 16 Devrinol CHIRALPAK IC-3 15 x 4.6 mm 15% methanol / C ml/min 12 bar bp N 1 Vince lactam CHIRALPAK IA-3 15 x 4.6 mm 3% methanol / C 2 3 ml/min 12 bar bp N H Minutes Minutes
22 3-Micron Columns Column Normal Reversed SFC Fast High Phase Phase Separations efficiency CHIRALPAK IA-3 CHIRALPAK IC-3 CHIRALPAK AD-3 CHIRALPAK AD-3R CHIRALCEL D-3 CHIRALCEL D-3R
23 Conclusions High efficiency at high flow rates Robust Pressure limit > 4 bar (Determined by HPLC unit) Improves productivity by reduction of analysis time High efficiency allows difficult separations Can be used in conventional HPLC units
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