Evaluation of a New Ionic Liquid Stationary Phase with PEG Like Selectivity
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1 Evaluation of a New Ionic Liquid Stationary Phase with PEG Like Selectivity L.M.Sidisky, G. A. Baney, J.L. Desorcie, D.L. Shollenberger, G. Serrano, and K.K. Stenerson Supelco, Div. of Sigma-Aldrich Bellefonte, PA USA T sigma-aldrich.com/analytical
2 Overview of Presentation Overview of Ionic Liquids Selectivity Evaluations Selectivity Ranking/ Assignment SLB-IL60 Applications Conclusions 2 sigma-aldrich.com/il-gc
3 Ionic Liquids: Definition and Uses Ionic liquids are a class of solvents with low melting points that consist of organic cations associated with (inorganic or organic) anions Ethyl ammonium nitrate (EtNH + 3)(NO - 3), which has a melting point of 12 C, was described in 1914 P. Walden, Bull. Acad. Imper. Sci. (St. Petersburg) 1800 (1914) Today, they are used as solvents, electrically conducting fluids, and sealants 3
4 Ionic Liquids: Example Structure SLB-IL100 1,9-di(3-vinylimidazolium) nonane bis(trifluoromethyl) sulfonyl imidate Benefits Greater stability compared to polysiloxane polymers and polyethylene glycols Lower column bleed, longer life, and higher thermal limits More resistant to damage from moisture/oxygen Numerous combinations of cations and anions are possible allowing for tailored selectivity, application, or function Dicationic (shown) or polycationic Cations, linkages, and/or anions can be changed Pendant groups can be added to cations and/or linkages 4
5 Common Anions for Ionic Liquid Phases - O N O O S CF 3 S CF 3 O - O O S CF 3 O (NTF 2 - ) (OT f - ) 5
6 SLB-IL60 Phase Structure 1,12-Di(tripropylphosphonium)dodecane bis(trifluoromethylsulfonyl)imide 6
7 Selectivity Evaluations 7 sigma-aldrich.com/il-gc
8 Ionic Liquid Test Mix TCEP Column, 110 ºC toluene n-tridecane 2. Toluene 3. Ethylbenzene 4. p-xylene 5. Isopropylbenzene (Cumene) 6. 1,2,4-Trimethylbenzene 7. 1,2,4,5-Tetramethylbenzene (Durene) 8. Cyclohexanone C
9 Ionic Liquid Columns, 110 ºC Isothermal toluene C13 6 SLB-IL59 1. n-tridecane 2. Toluene 3. Ethylbenzene 4. p-xylene 5. Isopropylbenzene (Cumene) 6. 1,2,4-Trimethylbenzene toluene 3,4 5 6 SLB-IL60 C
10 Ionic Liquid Columns, 110 ºC Isothermal toluene C13 3 SLB-IL n-tridecane 2. Toluene 3. Ethylbenzene 4. p-xylene 5. Isopropylbenzene (Cumene) 6. 1,2,4-Trimethylbenzene ,5 toluene 6 SLB-IL111 C
11 GC Column Polarity Scale and Naming System 11 sigma-aldrich.com/il-gc
12 McReynold s Number Probes Benzene (X)- Aromatics, olefins Butanol (Y)- Alcohols, nitriles, acids 2-Pentanone (Z)- Ketones, ethers, aldehydes, esters, epoxides, dimethyl amino derivatives Nitropropane (U)- Nitro and nitrile compounds Pyridine (S)- Bases, N-heterocycles 2-Methyl-2-pentanol (H)- Branched chain compounds, alcohols 1-Iodobutane (I)- Halogen compounds 2-Octyne (K)- Acetylenic compounds 1,4- Dioxane (L)- Ethers, polyols cis-hydrindane (M)- Polycyclic compounds, steroids 12
13 Description of Our Procedure Each column is characterized with a series of five probes plus several n-alkane markers to determine the retention index for each probe Benzene Butanol 2-Pentanone Nitropropane Pyridine McReynolds Constants are then calculated using the retention index data of the column relative to the retention index data for the same five probes on squalane, the most nonpolar GC stationary phase The five McReynolds Constants are summed to obtain Polarity (P) values, which are then normalized to SLB-IL100 (set at P=100) to obtain Polarity Number (P.N.) values Our procedure was proposed by Prof. Luigi Mondello (University of Messina, Italy). 13
14 Visual Representation 14
15 Experimentally Determined Polarity Numbers P (Polarity) = sum of the first 5 McReynolds Constants. P.N. (Polarity Number) = Polarity (P) normalized to SLB-IL100 (set at P=100). 15
16 SLB-IL60 16 sigma-aldrich.com/il-gc
17 Why SLB-IL60? Improved inertness over SLB-IL59 Complimentary selectivity to PEG phases Higher maximum temperature than PEG phases Lower bleed than PEG phases 17
18 Improved Inertness C1-C12 n-alcohols C isothermal Severe tailing SLB-IL59 C8-OL C9-C12 alcohols adsorbed C8-OL C9-OL C10-OL C11-OL SLB-IL60 C12-OL
19 Complimentary Selectivity to Wax SLB-IL Octanone 2. n-c15 3. n-octanol 4. n-c16 5. n-c17 6. n-c ,6-Dimethylphenol 8. 2,6-Dimethylaniline 9. n-c Wax
20 Higher Max Temp and Lower Bleed than Wax AU SLB-IL60, T f = 300 C 8.3pA FID bleed at published counts Wax #1, T f = 280 C temp. program max pA AU Wax #2, T f = 300 C 129pA
21 Applications BTEX and n-alkanes Solvents on the SLB-IL60 Fatty Acid Methyl Esters 21 sigma-aldrich.com/il-gc
22 BTEX + C9 to C14 n-alkanes 60 C Isothermal BC10 T C11 C9 EB p-xyl m-xyl o-xyl C12 SLB-IL59/ SLB-IL60 IL columns by increasing polarity numbers C13 C C10 B C11 SLB-IL76 Significantly less retention of aliphatics C9 T C12 EB p-xyl m-xyl C13 o-xyl C
23 BTEX + C9 to C14 n-alkanes 60 C Isothermal Most polar IL column C11 C12 C13 elutes before toluene B C13 T C14 EB p-xylm-xyl o-xyl SLB-IL
24 Chlorinated solvents on the SLB-IL60 & Wax ,6 2 All resolved SLB-IL60 yet faster elution Wax ,1-Dichloroethylene 2. trans-1,2-dichloroethylene 3. Methylene chloride 4. 1,1-Dichloroethane 5. Carbon tetrachloride 6. 1,1,1-Trichloroethane 7. Chloroform 8. Trichloroethylene 9. 1,2-Dichloroethane 10. Tetrachloroethene 11. 1,1,1,2-Tetrachloroethane 12. 1,1,2,2-Tetrachloroethane SLB-IL60: 30 m x 0.25 mm I.D. x 0.20 µm Wax: 30 m x 0.25 mm I.D. x 0.25 µm Oven: 40 C (4 min.), 8 C/min. to 200 C Helium, 30 cm/sec, set at 120 C 24
25 Ester & Ether solvents on the SLB-IL60 & Wax , SLB-IL Wax c Methyl formate 2. Ethyl formate 3. Methyl acetate 4. Tetrahydrofuran 5. Ethyl acetate 6. Isopropyl acetate 7. n-propyl acetate 8. 1,4-Dioxane 9. Isobutyl acetate 10. n-butyl acetate 11. Isoamyl acetate 12. n-amyl acetate Butoxyethano C: contaminant (2-Methylbutyl acetate) SLB-IL60: 30 m x 0.25 mm I.D. x 0.20 µm Wax: 30 m x 0.25 mm I.D. x 0.25 µm Oven: 40 C (4 min.), 8 C/min. to 200 C Helium, 30 cm/sec, set at 120 C 25
26 Cis / trans FAMES on SLB-IL60 vs. PEG Type Phase C18:1n9 cis / trans 180 C trans cis SLB-IL60 PEG C18:2n6 cis & trans FAME Isomers- 180 C C18:2n6 tt C18:2n6 tt C18:2n6 cc C18:2n6 cc
27 Peak list and run conditions for FAMEs GC analysis conditions are from methods AOAC and AOCS CE-1i-07 27
28 Fame Elution order- SLB-IL 60 compared to Wax 17: C18:1n9c 18: C18:1n9t 19: C18:2n6c 20: C18:2n6t SUPELCOWAX 10 26: C20:3n6 28: C20:3n3 35: C22:5n3 36: C24:0 37: C22:6n3 SLB-IL60 Notable elution changes from wax column: 1. C18:1n9t elutes before C18:1n9c 2. C18:2n6t elutes before C18:2n6c 3. C20:3n3 elutes before C20:3n6 4. C22:6n3 elutes before C22:5n3 and C24:0 C24:0 28
29 PUFA 3 Standard C14:0 C16:0 C16:1n7 C18:1n9 C20:5n3, C20:4n3? C22:6n3 C16:2n4 C16:3n4 C18:4n3 C18:1n7 C18:2n6 C18:3n3 C18:3n4 C18:0 C20:1n9 C20:3n3 C20:4n6 C22:5n3 SLB-IL60 C14:0 C16:0 C16:1n C18:1n9 C20:5n3 C22:6n3 C18:1n7 C18:3n4 C18:4n3 C20:4n6 Omegawax 250 C16:2n4 C16:3n4 C18:0 C18:2n6 C18:3n3 C20:1n9 C20:4n3 C20:3n3 C22:5n Same analysis conditions as 37-component mix 29
30 Extract of Farm-Raised Atlantic Salmon C16:0 C18:1n9 C14:0 C16:1n7 C18:2n6 C18:3n6 SLB-IL60 C18:3n4 C16:2n4 C16:3n4 C18:0 C18:1n7 C18:3n3 C18:4n3 C20:5n3 C20:3n3 C20:4n3? C20:1n9 C20:4n6 C22:1n9 C22:6n3 C22:5n BHT C16:0 C18:1n9 C18:2n6 C14:0 C16:1n7 C16:2n4 C18:0 C16:3n4 C18:1n7 C18:3n6 C18:3n3 C18:4n3 C18:3n4 C20:1n9 C20:4n6 C20:3n3 C20:4n3 C20:5n3 Omegawax 250 C22:6n3 C22:5n Samples prepared using AOCS Official Method Ce 1k-09; BHT added as an antioxidant 30
31 Conclusions Ionic Liquids are different than traditional polymer GC phases Not susceptible to same stability issues as siloxane and PEG based phases More parts to change thus more possible chemistries possible selectivity Higher temp. limit than traditional phase of comparable polarity Ionic Liquids extend the polarity range of GC phases SLB-IL111 more polar than any traditional phase SLB-IL60 Ionic Liquid Phase offers Improved inertness over SLB-IL59 Complimentary selectivity to PEG phases Higher maximum temperature than PEG phase Lower bleed than PEG phases Can be used for a wide variety of applications 31
32 Acknowledgements Prof. Daniel Armstrong, U. Texas Arlington Prof. Luigi Mondello, U. Messina, Messina, Italy Supelco R&D Team Our customers worldwide 32
33 Thank You 33
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VAL VAL QTY
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