Supercritical Fluid Chromatography: Past, Present and Future
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1 Supercritical Fluid Chromatography: Past, Present and Future e-sear November 16, 211 Pat Sandra
2 ... I love CO 2 as mobile phase Green Better than NP-LC Cheaper than LC Faster than LC Unique selectivity Complementary to RP-LC & HILIC Compatibility with detectors MD (Semi)-Prep SFC but... Terry Berger in J. Chromatogr. A 1218 (211) 232 This new low noise level makes it possible to validate SFC methods for the first time
3 21st Century Triangle Throughput Productivity Resolution
4 21st Century Triangle Throughput Productivity Resolution
5 Supercritical Fluid Chromatogtraphy: Panacea or Pitfall? London 29
6 Supercritical Fluid Chromatography: The Good, the Bad or the Ugly? Bruges 21
7 Content Fundamentals Past ( /29) Present (29 211) Future
8 P Fundamentals - 1 NO phase transition SOLID LIQUID SUPER- CRITICAL FLUID 73.8 bar GAS 31.1 C T Courtesy of Dr. Christopher Rayner, University of Leeds
9 Fundamentals - 2 R s = N.5 a - 1 k 4 a 1 + k N = L/2d p t R = L/u (k + 1) = N.2d p /u (k + 1)
10 Fundamentals - 3 Density N k a but also on - Viscosity - Solubility Modifiers!s
11 Fundamentals - 4 N SFC = N HPLC u opt SFC = up to 5 times > than u opt HPLC This is only correct for pure CO 2 u opt SFC = up to 2-3 times > than u opt HPLC For CO 2 with 5 to 4% MeOH DP SFC << DP HPLC
12 h Fundamentals SFC HPLC ml/ cm/s 25 mm x 4.6 mm ID x 5 µm RX-Sil
13 Selectivity? Fundamentals - 5 Multi-mode technique from highly polar to apolar solutes but in senso stricto NORMAL PHASE Characterization of Stationary Phases for SFC with the Solvation Parameter Model C. West & E. Lesellier in Advances in Chromatography 21 Vol 48, All NP chiral and achiral stationary phases Dedicated SFC stationary phases 2-Et pyridine, triazol,... DEAP, PPU, DNP (?)
14 Past / : Klesper and Turner first used supercritical fluids as mobile phase in : 1 st commercial SFC instrument introduced by HP 1986: Capillary SFC developed by Lee Scientific 1992: 2 nd commercial SFC instrument introduced by HP HP G125A SFC : R&D 2 28/29: the SFC believers
15 Response Response Response Response Response Response Chiral separations Generic method O 1: X= COOCH 3 4: X= CH 2 COOCH 3 14: X= CH 3 15: X= CH 2 CH 3 h X O 7: X= COOCH 3 1: X= CH 2 COOCH 3 17: X= CH 3 18: X= CH 2 CH A 2 15 B X O z X 2: X= COOCH 3 5: X= CH 2 COOCH 3 16: X= CH 3 h Y O 8: Y= CH 2 COOCH 3, Z= H 11: Y= (CH 2 ) 2 COOCH 3, Z= H 12: Y= H, Z= (CH 2 ) 2 COOCH 3 19: Y= H, Z=CH 2 CH 3 Time (.) 18 2 } 16 C 18 D Time (.) O X X 3: X= COOCH 3 6: X= CH 2 COOMe h O 9: X= COOCH 3 13: X= CH 2 COOCH Time (.) E Time (.) F O Y h O 21: X= CH 2 COOCH 3, Y= H 22: X= H, Y= CH 2 COOCH Time (.) Time (.) COOCH 3 X
16 Books 1988 Modern SFC Ed. Curt White 1988 SFC Ed. Roger Smith 199 Analytical SFC & SFE Ed. Milton Lee & Karin Markides 1995 Packed Columns SFC Terry Berger 1998 SFC with Packed Columns Eds. Klaus Anton & Claire Berger 1999 Practical SFC & SFE Eds. Marcel Caude & Didier Thiebaut
17 the good Packed column SFC has characteristics which logically make it superior to LC for most molecules that can be solvated by SFs. in Packed Column SFC by T.A. Berger 1995 Why could SFC not keep its promises?
18 the bad and the ugly (from the cavilers, pettifoggers, etc.) No fundamental developments Instability in the SFC instrumentation market to difficult... too many parameters Features overemphasized New developments e.g. in column manufacturing, suffered from reproducibility issues, bleeding in MS, etc. The detector issue UV... ELSD, CAD, MS? Robustness IQ/PV? from research to QA/QC validation? Application notes/publications considered competitive but not at all contraproductive
19 Present Desire of environmentally conscious techniques Major instrument companies entered or re-entered the SFC market - Agilent Technologies - Waters - Jasco - (Selerity Technologies) Unique selectivity (NP-LC), complementary to RP-LC and HILIC Robustness at the GC and HPLC level
20 21st Century Triangle Throughput Productivity Resolution
21 Chiral Separations Generic conditions High Productivity R 7 R = 1.42 S 7 R = 1.37 Cellulose LUX-1 (4.6 x 25 mm, 3 µm), SF = CO 2, Modifier = MeOH with.1% TFA +.1% DEA isocratic at 3%, Outlet Pressure = 15 bar, Flow Rate = 2. ml/, Detection = UV 22 nm, Temperature = 5 C
22 Chiral High Throughput mau 5 25 mau mau mau mau LUX C-1 LUX C-2 LUX C-3 LUX C-4 LUX A-2 5 mau mau 4 2 mau AD-3 AD-5 AS-5
23 MS Abundance mau 5 25 LUX C-1 From 5 to 25 mm 5 to 25 mm mau mau mau mau 1 5 mau mau 4 2 mau LUX C-2 LUX C-3 LUX C-4 LUX A-2 AD-3 AD-5 AS-5 x1 2 + EIC(25.) Scan sfcquiral4.d EIC(247.) Scan sfcquiral4.d x x1 + EIC(455.) Scan sfcquiral4.d x1 + EIC(382.) Scan sfcquiral4.d Smooth (1) EIC(438.) Scan sfcquiral43.d x EIC(42.) Scan sfcquiral43.d trans-4-cotinene carboxyline acid Bendrofumethiazide Alprenolol HCl Mepivacaine HCl Verapamil SFC-TOFMS Sample pooling Warfarin
24 mv Thiourea PI-X Trace Analysis Claudio Brunelli Pfizer, Sandwich, UK Blood/plasma Extraction Level ( g/ml) 1.5 (.1%) 7.5 (.5%) 15. (.1%) Lipid profile Mean % Recovery LC-MS % RSD Minutes
25 Generic method for achiral analysis Stationary phase - particle size Column dimensions - Length - ID Mobile phase - CO 2 - Modifier - Additive 1 - Additive 2 more acidic conditions more basic conditions Restrictor Detection Bare silica * 1.8, 3 and 5 µm 5, 1, 15 and 25 cm 2, 3 and 4.6 mm 1 to 5 ml/ MeOH or EtOH 1 to 5% water 5 to 2 mm ammonium formate or acetate Formic or acetic acid Ammonium hydroxide 1 to 2 bar UV-DAD MS (Q, QqQ, TOFMS, Q-TOFMS) ELSD CAD * 2-Et pyridine, Diol, Cyano, Chiral columns, etc.
26 Alcohol ethoxylates CH 3 (CH 2 ) m O(CH 2 CH 2 O) n H RX-SIL column - 25 mm x 4.6 mm x 5 µm; 4 C; Po 1 bar FLOW = 3 ml/ Modifier = methanol/water 95/5 (v/v) + 1 mm ammonium formiate Modifier = 1 to 4% in 2
27 AU 254 nm Princeton Pyridine (4.6 x 25, 3 um) Alltima Silica (4.6 x 25, 3 um) , , , ,13 15, Time () Et-pyridine Silica ) Caffeine 2) Ibuprofen 3) Theophylline 4) Theobroe 5) Thye 6) Adenine 7) Uracil 8) Fenoprofen 9) Flurbiprofen 1) Cortisone 11) Prednisone 12) Cytosine 13) Hypoxanthine 14) Hydrocortisone 15) Prednisolone 16) Sulfamerazine 17) Sulfamethoxazole 18) Sulfadimethioxime 19) Estriol 2) Sulfaguanidine 21) Sulfaquinoxaline 22) Sulfamethizole Columns = 4.6 x 25 mm, 3 µm, Flow Rate 2.5 ml/, Modifier = 5 to 3% in 2 Modifier = MeOH w. 2 mm NH 4 OOCH Pressure = 1 bar, Temperature = 4 C For Research Use Only. Not for use in diagnostic procedures.
28 Triton X RX-SIL column 5 mm x 4.6 mm x 1.8 µm; 4 C; Po 1 bar CO 2 FLOW = 2 ml/ Modifier = methanol/water 95/5 (v/v) + 1 mm ammonium formiate Modifier flow =.4 ml/ to 1.3 ml/ in 5
29 High Resolution - Pesticides P 7 P3 P2 P4 P1 P 6 P5 P 8 P11 P12 P14, P13 P15 P1 P 9 P16 P18 P17 P19 P21 P2 P24 P22 P23 P25 P26 P27 Column = 4 x Zorbax RX-SIL (4.6 x 25 mm, 5 µm), Flow rate = 2. ml/, Outlet P = 15 bar Modifier = MeOH with 2 mm HCOONH 4 (2% H 2 O), % modifier. Detection = 254 nm, Temp = 4 C,
30 Detectors 6 C Caloratherm Heating Element UV Detector BPR MSD CAD ELSD SS Capillary Tubing.12 x 15 mm SS Capillary Tubing.12 x 4 mm LC Pump
31 mau DAD1 A, Sig=254,4 Ref=36,1 (L:\SFC_AGI...52_ELSD\ORE11138_ELSD \ D) A) UV 254 nm mv ELS1 A, Voltage (L:\SFC_AGI...ORE11138_21152_ELSD\ORE11138_ELSD \ D) B) ELSD Theobroe Theophylline 7 Cortisone 1 Prednisone 9 8 Hydrocortisone 1 Prednisolone Sulfaquinoxaline Sulfamerazine m m Column = Zorbax RX-SIL (4.6 x 25 mm, 5 µm), Flow Rate = 2. ml/, Outlet P = 12 bar, SF = CO2, Modifier = MeOH with 2 mm NH4COOH (2% H 2 O), Modifier gradient = -2 : 5-4%, Column T = 4 C, Make-up = MeOH with 2% H 2 O at.2 ml/, Caloratherm = 6 C, Detection = UV (254 nm), ELSD (Evap = Neb = 35 C, smoothing = 3. s, PMT gain = 1, data rate = 4Hz, Flow Rate = 1.6 SLM). For Research Use Only. Not for use in diagnostic procedures.
32 ... a real drug discovery sample UV Single Quad TIC + Single Quad TIC -
33 Sensitive deteration of impurities in achiral pharmaceuticals by supercritical fluid chromatography using the Agilent 126 Infinity Analytical SFC System Publication Number EN High resolution separations by supercritical fluid chromatography using a coupled column approach with the Agilent 126 Infinity Analytical SFC System Publication Number EN Comparison of UV detection limits between the Agilent 126 Infinity Analytical SFC System and an Agilent 12 Series LC System Publication Number EN Chiral impurity analysis and enantiomeric excess deteration with the Agilent 126 Infinity Analytical SFC System Publication Number EN Agilent 126 Infinity SFC/MS Solution Publication Number EN
34 The future... CO 2 is a super fluid as mobile phase Super fluid chromatography? SFC instrumentation New analytical possiblities New challenges in understanding the mechanisms...
35 Green HILIC Column Zorbax RSiL (25 mm x 4.6 mm x 5 µm d p ) - Flow 1 ml/ A HILIC Ethanol/ Ammonium formate 2 mm (95/5) B HILIC Acetonitrile/ Ammonium formate 2 mm (95/5) A. Pereira, A.J. Giron, E. Admasu and P. Sandra, J. Sep. Sci. 33, (21) 1. uracil, 2. thye, 3. guanine, 4. cytosine, 5. adenine For Research Use Only. Not for use in diagnostic procedures.
36 Green HILIC Column Zorbax RX SiL (25 mm x 4.6 mm x 5 µm d p ) - Flow 1 ml/ HILIC Ethanol/ Ammonium formate 2 mm (95/5) HILIC Acetonitrile/ Ammonium formate 2 mm (95/5) 1.5 ml/ of CO ml/ of CO 2 1. uracil, 2. thye, 3. guanine, 4. cytosine, 5. adenine For Research Use Only. Not for use in diagnostic procedures.
37 Modular simplified system Optional Heater Liquid CO 2 Check valve Column Fixed restrictor OVEN Modifier P. Sandra, K. Sandra, A. Pereira, G. Vanhoenacker and F. David, LC.GC Europe 23 (5), (21). A. Pereira, F. David, G. Vanhoenacker, C. Brunelli and P. Sandra, LC.GC North America, November Issue (211).
38 mv mau mau A B C 12 bar FR UV 254 nm ELSD UV 254 nm mv D NO restriction ELSD
39 mau Counts +APCI TIC Scan Frag=225.V SFC d x A DAD1 - A:Sig=254,16 Ref=36,16 SFC d B Acquisition Time () ) Acetone 2) Theophylline 3) Caffeine 4) Cortisone 5) Prednisone 6) Hydrocortisone, 7) Prednisolone 8) Sulfaquinoxaline 9) Sulfamerazine A) APCI - positive mode, B) UV at 254 nm Column RX Sil 5 mm x 4.6 mm x 1.8 µm at 4 C. CO 2 Flow 3.7 ml/. Modifier methanol at.7 ml/ NO restrictor but outlet pressure at ~ 8 Bar For Research Use Only. Not for use in diagnostic procedures.
40 Alberto Pereira Frank David Melissa Dunkle Gerd Vanhoenacker Claudio Brunelli Roman Szucs William Farrell Selerity Technologies (Jody Clark) The SFC believers You for your attention
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