Silanol. Groups Liquid Chromatography

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1 Abstract umber: 0-8P Study of Secondary Interaction Based on Residual lanol Groups for Reversed-Phase Liquid Chromatography II orikazu agae Ph.D, Kouji Yamamoto, Chiaki Kadota Chromaik Technologies Inc. Website: Pittcon 009

2 abstract It has been said that residual silanol groups on a C8 silica stationary phase yielded peak tailing for basic compounds. A lot of efforts have been exerted for reducing effect of residual silanol groups by an end-capping or embedding a polar group in an alkyl chain. Consequently, a sharp peak of a basic compound has been obtained although retention of a basic compound has been getting little. n the other hand, on hydrophilic interaction chromatography (hilic) mode, a silica column is recently used under a mixture of an organic solvent and a buffer solution, which is the same as a mobile phase used for reversed-phase liquid chromatography. In this mode, a peak shape of a basic compound is good not tailing. In other words a silanol group on a silica stationary phase is not a cause for tailing of a basic compound, at least on hilic mode. Pittcon 009

3 We found that a silanol group controlled its activity by the heat treatment didn t make a basic compound tailing even if it existed on the C8 reversed-phase. Secondary interaction based on residual silanol groups for reversed-phase liquid chromatography was evaluated using a C8 stationary phase with silanol groups controlled its activity. It was observed that retention of basic compounds and polar compounds was several times larger than that using a conventional end-capped C8 silica stationary phase, furthermore it dropped as p value of a mobile phase decreased and salt concentration in a mobile phase increased while retention of neutral compounds didn t change completely. It is considered that an ion-exchange interaction occurred clearly by residual silanol groups on a C8 silica stationary phase. As a result, a residual silanol group controlled its activity could change selectivity of basic compounds without peak tailing. Pittcon 009

4 Form of silanol groups and peak shape of pyridine Isolated lanol Column A Column B Column C Vicinal lanol Geminal lanol Pyridine peak 60% C / Pittcon 009

5 ur hypothesis Peak tailing of a basic compound is caused by the state of silanol groups, not by existence of silanol groups on silica surface. lanol groups near a strong hydrophobic site don t occur an ion-exchange interaction etc. rapidly. Consequence Decrease density of alkyl groups and make hydrophobicity low. Control activity of silanol groups near only hydrophobic site Pittcon 009

6 Variation of water on silica s surface Absorbed water Bonded water Desorption of absorbed water (0 ~ 0 C) Desorption of bonded water (~ 00 C) Desorption of silanol group (~ 800 C) Pittcon 009 6

7 Change of silanol groups by heat treatment lanol group - + Low temp. Warped siloxane igh temp. loxane Condensation of silanol group starts from near 00 C. Vacuum heat treatment makes an amount of silanol group low by water deprivation and siloxane produces. Under 00 C, siloxane reverts silanol groups by rehydration. ver 00 C, rehydration do not occur. Pittcon 009 7

8 After heat treatment Control of silanol group loxane near hydrophobic site (C8) is kept at the same state and no silanol goup produces by rehydration. Prevention of tailing for basic compound Active silanol groups for basic compounds heat Change to loxane loxane away from hydrophobic site is rehydrated. Consequently silanol group produces and it is unaffected by hydrophobic site. Increase of retention of polar and basic compounds, in spite of no change of retention of a neutral compound Pittcon 009 8

9 Experiment lica gel Pore diameter: nm,specific surface area: 0 m /g, Particle size: µm Bonded ctadecylsilane Carbon content: % As reference, preparec8 phase with end-capping (TMS) eat treatment in a vacuum Temperature: 00 C,Treatment time: 8 hours As reference, prepare C8 phase without heat treatment Evaluation Column: Sunrise C8-SAC (with heat treatment) Sunrise C8 (with end-capping) Column dimension: 0 mm x.6 mm i.d. Mobile phase: acetonitrile or methanol/buffer solution Pittcon 009 9

10 a) b) c) Comparison of pyridine peak shape C8 with TMS Sunrise C8 C8 without heat treatment C8 with heat treatment Sunrise C8-SAC Mobile phase: 0% C / Flow rate:.0 ml/min Temperature: 0 ºC Sample: =Uracil =Pyridine =Phenol Retention time / min Pittcon 009 0

11 C8 with TMS Sunreise C8 C8 with heat treatment Sunrise C8-SAC Separation of xanthine times longer = Theobromine = Theophylline =Caffeine C C C C C C = Phenol C Time (min) Column dimension: 0 x.6 mm Mobile phase: Methanol/0mM Phosphate buffer (p.)=(0:70) Flow rate:.0 ml/min Temperature: 0 ºC Pittcon 009

12 Separation of antidepressants =Uracil =Propranolol =ortriptyline =Amitriptyline =Toluene C C C C C C C8 with TMS Sunrise C8 Acetonitrile/0mM phosphate buffer p6.0 (80:0) Retention increase by ionexchange interaction C8 with heat treatment Sunrise C8-SAC Acetonitrile/0m phosphate buffer p6.0 (80:0) Time (min) Pittcon 009

13 Control of retention by mobile phase p Acetonitrile/0mM phosphate buffer p.0 (0:0) Acetonitrile/0mM phosphate buffer p. (0:0) Column: C8 with TMS, Sunrise C8, C8 with heat treatment, Sunrise C8- SAC 0 x.6 mm Flow rate:.0 ml/min Temperature: 0 ºC Sample: =Uracil, =Propranolol, =ortriptyline, =Amitriptyline, =Toluene Acetonitrile/0mM phosphate buffer p6.0 (80:0) Time (min) Pittcon 009

14 p.7 nly acetic acid p. p. p.0 p.9 Separation of basic compounds with ammonium acetate: Effect of p =,000 =,00 Column: C8 with heat treatment, Sunrise C8-SAC 0 x.6 mm Mobile phase: Acetonitrile/00mM ammonium acetate(70:0) Flow rate:.0 ml/min Temperature: 0 ºC Sample: =Uracil, =Toluene, =Propranolol, =ortriptyline, =Amitriptyline =,00 An ammonium ion makes a peak shape of a basic compound sharp. =,00 p 6.8 =, Time (min) Pittcon 009

15 Separation of basic compounds with ammonium acetate: Effect of salt concentration 00 mm 00 mm 0 mm =,000 =,00 Column: C8 with heat treatment, Sunrise C8-SAC 0 x.6 mm Mobile phase: Acetonitrile/ ammonium acetate p. (70:0) Flow rate:.0 ml/min Temperature: 0 ºC Sample: =Uracil, =Toluene, =Propranolol, =ortriptyline, =Amitriptyline =,000 mm =,00 0 mm =, Time (min) Pittcon 009

16 Relationship between buffer concentration and retention log k ,000,000 0,000 8,000 6,000,000,000 [amitriptyline] log [buffer concentration] Toluene Propranolol ortriptyline Amitriptyline (ami) z B zb Vr log k = - log[ A] + log[ A] + log + log K z z V z A A A:ion in eluent,b:ion of sample, k:retention of B,K:selection coefficient Z A, Z B :charge,v r, V m :resin volume and mobile phase volume in column m Pittcon A B A

17 Effect of salt of buffer to retention time Retention time (min) Sodium phosphate Sodium citrate Sodium acetate Sodium formate Procainamide ammonium phosphate ammonium citrate ammonium acetate -Acetylprocainamide ammonium formate Tris Column: C8 with heat treatment, Sunrise C8-SAC 0 x.6 mm Mobile phase: Methanol / 0mM buffer p6.8 (70:0) Flow rate:.0 ml/min Temperature: 0 ºC Sample: =Procainamide, =-Acetylprocainamide Pittcon 009 7

18 Effect of salt of buffer to peak asymmetry Asymmetry (USP tailing factor) Sodium citrate Sodium phosphate Sodium acetate Sodium formate ammonium citrate ammonium phosphate Procainamide ammonium acetate ammonium formate -Acetylprocainamide Tris Column: C8 with heat treatment, Sunrise C8-SAC 0 x.6 mm Mobile phase: Methanol / 0mM buffer p6.8 (70:0) Flow rate:.0 ml/min Temperature: 0 ºC Sample: =Procainamide, =-Acetylprocainamide Pittcon 009 8

19 Separation of metal chelating compound ther pure DS A: 0mM phosphoric acid B: 0mM formic acid C8 with heat treatment Column: ther pure DS mm C8 with heat treatment, Sunrise C8-SAC, Mobile phase: A)Acetonitrile/0mM phosphoric acid (0:90) B)acetonitrile/0mM formic acid (0:90) C)acetonitrile/0mM acetic acid (0:90) Flow rate:.0 ml/min Temperature: 0 ºC Sample: =8-Quinolinol,=Caffeine C: 0mM acetic acid Time (min) Time min) Pittcon 009 9

20 Separation of nucleic acid bases C C Column: C8 with heat treatment, Sunrise C8-SAC 0 x.6 mm Mobile phase: 0mM Phosphate buffer p. Flow rate:.0 ml/min Temperature: ºC Sample: =Cytosine,=Uracil, =Cytidine, = Thymine, *=impurity * 0 0 Retention time / min 0 Pittcon 009 0

21 Conclusions Residual silanol group in proposed C8 phase made retention of polar compounds including basic compounds high. lanol group controlled its activity by heat treatment did not make peak of basic compounds be tailing. Furthermore, ion-exchange interaction was recognized and retention of basic compounds could be changed by p or salt concentration in a mobile phase. Proposed C8 phase was effective to separation of a metal chelating compound. It is surmised that hydration or change of state of silanol groups contributed to suppress influence of a metal impurity on a silica support. Pittcon 009

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