Thermal Desorption combined with dynamic headspace: a versatile tool for miniaturized sample preparation
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1 Thermal Desorption combined with dynamic headspace: a versatile tool for miniaturized sample preparation 4 th Stir Bar Sorptive Extraction Technical Meeting September 18-19, Paris Frank David
2 Tutorial lay-out Methods for the analysis of volatiles DHS principles DHS modes Examples Positioning DHS versus other methods
3 Sample Preparation Methods for Volatiles Static Headspace (SHS) Single equilibrium + single injection = classical SHS CTS refocusing Multiple headspace extraction (MHE) Multiple runs (= Kolb method, e.g. Monomers in polymers) Multiple sampling + trapping + single run (eg HIT-SHS, ITEX) Dynamic Headspace (DHS) Purge & Trap (P&T) Sorptive Extraction Solid Phase Micro-Extraction (SPME) New: SPME Arrow (increased volume of extraction phase) Stir Bar Sorptive Extraction (SBSE)
4 Static Headspace (SHS) Syringe Head Space Bottle Injector
5 Solid Phase Micro-Extraction (SPME) Pierce sample septum Expose fiber Extract Retract fiber Remove Pierce GC Inlet septum Expose fiber Desorb Retract fiber Remove SORPTION DESORPTION
6 SHS or SPME Analysis of Halides and Haloalkenes in pharmaceuticals chloromethane (1) benzyl bromide vinyl chloride (2) bromomethane vinyl bromide 4-methylbenzyl chloride (26) iodomethane 4-methylbenzyl bromide 1-chloro-2-methylpropene 1-chloropropane 4-fluorobenzyl chloride 1-bromo-2-methylpropene 1-bromopropane 4-fluorobenzyl bromide 2-chloroacrylonitrile 1-iodopropane 2-chloroethanol 4-chloro-butyl ether (28) 2-chloropropane 2-bromoethanol cis-1,2-dichloroethylene 2-bromopropane 2-iodoethanol trans-1,2-dibromoethylene 2-iodopropane 3-bromo-2-methyl-acrylonitrile 2-(2-chloroethoxy)ethanol benzyl chloride
7 Analysis of Halides and Haloalkenes Abundance SPME (100 µm PDMS) T IC : A Z 2 & 3 _ n g.d \ D A T A S IM.M S ( * ) T IC : _ S P M E.D \ D A T A S IM.M S ( * ) SHS Time--> Conc: 0.5 ppm in API = 25 ppb in solution
8 HIT-SHS and HIT-SPME option on Gerstel MPS-TDU-CIS
9 HIT-SHS and HIT-SPME option on Gerstel MPS-TDU-CIS
10 Dynamic Headspace Continuous purging of headspace (sample) at controlled temperature for controlled time at controlled flow. Trapping of VOCs (adsorbent, sorbent, +/- cryo) Thermal desorption of trap Goal: exhaustive extraction = highest sensitivity He Tenax
11 DHS TDU
12 WHY DHS? Abundance 60 VOCs in water 1 ppb GC-MSD in scan mode Static headspace (SHS) Sensitivity!! Dynamic headspace (DHS) Time, min
13 WHY DHS? Abundance VOCs in water 1 ppb GC-MSD in scan mode Solid phase microextraction (SPME) 65 µm PDMS/DVB Dynamic headspace (DHS) Sensitivity for the highly volatiles!! and for the other volatiles!! Complete profile less selective Time, min
14 Limonene Method comparison for fruit drink Static Headspace SPME Carbotrap/DVB/PDMS DHS C18 ester (high Mw) 14
15 DHS vs SPME: aldehydes/ketones in water x x TIC Scan etalon haut.d + TIC Scan etalon haut SPME 3.D Zoom: x10 DHS-GC-MS SPME-GC-MS Counts vs. Acquisition Time (min) Compound TIC area in DHS-GC-MS TIC area in SPME-GC-MS Fold sensitivity increase Acetaldehyde Hexanal Nonanone
16 Furaneol Furaneol 8 x DHS vs SPME: yoghurt aroma x EI TIC Scan 1g yoghurt DHS.D +EI TIC Scan 1g yoghurt -SPME.D 1g yoghurt in the vial DHS-GC-MS SPME-GC-MS Counts vs. Acquisition Time (min) trans-hexenal min by DHS and not by SPME
17 DHS vs SPME: beef powder 250mg powder with 1mL water in 20 ml vial x10 8 +EI TIC Scan 250mg powder+water DHS.D x10 8 +EI TIC Scan 250mg powder+1ml water -SPME.D DHS-GC-MS SPME-GC-MS Counts vs. Acquisition Time (min)
18 DHS vs SPME: Cognac XO 2 ml in 20 ml vial ethanol SPME DHS 18
19 DHS modes of operation Classical mode: single extraction single run Tenax or Carbotrap adsorption tube without/with dry purge FEDHS: full evaporation DHS MVM: multi-volatile method Multiple tubes & DHS sampling Desorption & trapping Single GC run Derivatization-DHS DHS Large
20 Same scales Complementary DHS methods for aroma compounds in food acetaldehyde DHS on strong Carbotrap at 10 C Highly volatiles EtOH DHS on Tenax TA at 70 C C18 ester (High Mw)
21 DHS parameters Extraction (classical DHS) Incubation (sample) temperature (as low as possible) Trap: Material Temperature (higher = less water) Time & flow (= x rinses of vial volume) example: 500 ml volume, 50 ml/min = 10 min = 25 rinses Dry purge??? (loss of volatiles) MVM? TDU: desorption temperature (time, flow) CIS: Focusing temperature (w/ packing?) Injection mode (split, splitless) Injection temperature
22 Full evaporation dynamic headspace (FEDHS) 100 μl of aqueous sample is dispensed into a HS vial and purged with inert gas at an elevated temperature (80ºC) using DHS. Volatile and semi-volatile analytes are transferred into the trap (Tenax). After dry purge of water, the trap is thermally desorbed for GC analysis. Higher recovery of hydrophilic compounds Purge gas In 100μL~ 80 80
23 FEDHS method parameters FEDHS conditions Sample volume: 50 µl Trap: Tenax Trap temperature: 40 C Incubation temperature: 80 C Purge: ml/min dry purge ml/min TDU/CIS conditions TDU: 30 C, 60 C/min to 270 C (5 min) Transfer temperature: 280 C (splitless) CIS: -100 C, 12 C/sec to 280 C (7 min) using a Tenax liner
24 DHS vs FEDHS - GC-MS of coffee x TIC Scan DHS Tenax coffee 0,5mL.D 7 6 DHS, 35 C incubation x TIC Scan FEDHS Tenax coffee 0,5mL.D 7 6 FEDHS, 80 C incubation Counts vs. Acquisition Time (min)
25 Selectable 1 D/ 2 D analysis of allergens in cosmetics in combination with FEDHS Abundance 1 D chromatogram of a cosmetic sample (body cream) 4.8e e+07 4e e+07 Abundance 2e e e+07 matrix (glycerin) 3.2e e e+07 2e Time, min 1.6e e Time, min
26 Selectable 1 D/ 2 D analysis of allergens in cosmetics in combination with FEDHS Abundance 4.8e+07 1 D/ 2 D chromatogram of body cream Heart-cut min 4e e+07 Co-elution of matrix + heart-cut farnesol 1 & 2 / isoeugenol / hexyl cinnamaldehyde 2.4e e D Target compounds (23 25 min) Time, min
27 Selectable 1 D/ 2 D analysis of allergens in cosmetics in combination with FEDHS Extracted Ion Chromatograms from 2 D part Abundance GLYCERIN ion 61 hexyl cinnamaldehyde ion Farnesol 1 & 2 ion 69 OTHER MATRIX COMPOUND ion isoeugenol ion Time, min
28 Sequential Dynamic Headspace Sampling incorporating a Multi-Volatile Method (MVM) for Aroma Analysis Developed by Nobuo Ochiai, Kikuo Sasamoto and Jun Gerstel KK
29 Dynamic Headspace Method 1: Very Volatile Analytes (J. Tsunokawa, N. Ochiai, K. Sasamoto, A. Hoffmann, in preparation)
30 Dynamic Headspace Method 2: Volatile or Semi Volatile Analytes (J. Tsunokawa, N. Ochiai, K. Sasamoto, A. Hoffmann, in preparation)
31 Dynamic Headspace Method 3: Volatile, non volatile and hydrophillic analytes (J. Tsunokawa, N. Ochiai, K. Sasamoto, A. Hoffmann, in preparation)
32 Dynamic Headspace Method 4: TDU Multi Desorption (J. Tsunokawa, N. Ochiai, K. Sasamoto, A. Hoffmann, in preparation)
33 Dynamic Headspace Method 4: TDU Multi Desorption (J. Tsunokawa, N. Ochiai, K. Sasamoto, A. Hoffmann, in preparation)
34 Dynamic Headspace Method 4: TDU Multi Desorption (J. Tsunokawa, N. Ochiai, K. Sasamoto, A. Hoffmann, in preparation)
35 Acetaldehyde** 2,3-Butanedione* 2,3-Pentanedione* 1-Methyl pyrrole Furan 2-Methyl butanal 3-Methyl butanal** 2,3,5-Trimethylpyrazine* 4-Vinyl guaiacol * Guaiacol* 2-Methyl pyrazine 2-Acetylpyrrole + Maltol 4-Ethylguaiacol* Furaneol*, ** Pyridine Furfuryl alcohol TIC of a brewed coffee by DHS-MVM TIC m/z 117, 90 Indole O NH HO O m/z 62,47 DMS HO O m/z 151, 152 Vanillin* O Sample: Coffee 100 μl Incubation Temp.: 80 ºC Purge volume: 3000 ml Column: DB-WAX 30 m x 0.25 mm i.d., 0.25 μm thickness
36 Acetaldehyde Furan DMS Propanal 2-Methylfuran Butanal 2,3-Butanedion Pentanal 2,3-Pentanedion DMDS Pyrrole 2,5-Dimethylpyrazine Furfural cis-3-hexenol 1-Hexanol Guaiacol Ethyl decanoate Indole gamma-nonalactone beta-damascenone Coumarin recovery [%] Brewed Coffee Extraction Trap 1 Trap 2 Trap
37 Acetaldehyde Furan DMS Propanal 2-Methylfuran Butanal 2,3-Butanedion Pentanal 2,3-Pentanedion DMDS Pyrrole 2,5-Dimethylpyrazine Furfural cis-3-hexenol 1-Hexanol Guaiacol Ethyl decanoate Indole gamma-nonalactone beta-damascenone Coumarin recovery [%] Brewed Coffee Extraction Trap 1 Trap 2 Trap
38 DHS-Multi-Volatile Method (DHS-MVM )* MVM option (Maestro or later) Multiple Tube Desorption FEDHS Method BXX-X Shincarbon trap Top notes Optimized for enrichment of super VOC and top notes Method BX Shincarbon trap Top to middle note Optimized for enrichment of remaining top notes to middle notes FEDHS Tenax TA trap Middle to base note Optimized for enrichment of remaining middle notes to base notes, polar and low boiling compounds Three TDU tube are sequentially thermal desorbed and cryo-focused on CIS, and then injection into GC-MS * N. Ochiai, J. Tsunokawa, K. Sasamoto, A. Hoffmann, J. Chromatogr. A 1371 (2014)
39 Comparison of BXX-X, BX, FEDHS and MVM for analysis of noodle soup stock TIC (BXX-X) TIC (BX) TIC (FEDHS) TIC (MVM) Courtesy: Gerstel KK, Japan
40 DHS + derivatization Example: Determination of stale-flavor compounds (aldehydes, ketones) using DHS on PFBHA impregnated PDMS tubes and GC-MS Derivatization reaction Pentafluorobenzyl hydroxylamine aldehyde or keton oxime (structural isomers syn/anti) Target solutes: octanal, nonanal, decanal, 2-octenal, 2-nonenal, 2,4-decadienal
41 Determination of stale-flavor compounds using DHS on PFBHA impregnated PDMS tubes and GC-MS DHS method for impregnation DHS method for DHS of beer samples These methods can be put in one sequence consisting of sequential DHS impregnation and (beer) sample analyses Impregnation + dry purge Sampling + TDU desorption
42 SIM chromatogram (5 ppb in beer) Abundance Method is applicable also for other aldehydes (formaldehyde, acetaldehyde, ) Octanal Nonanal Decanal Nonenal Octenal * * * * 2,4-decadienal ,6-Nonadienal Time, min
43 Overlaid SIM chromatograms for Beer & spike at 1 ppb Abundance Nonanal (+/-550 ppt) BEER 2-Octenal (150 ppt).. 2-Nonenal (+/-75 ppt) 2,4-Decadienal.. (25 ppt) SPIKED Time, min
44 DHS Large option for MPS
45
46 Importance of DHS in Flavor Analysis Perception: no technique can deliver the same results as steam destillation (or SAFE) Gerstel DHS: Sensitivity Automation Reduced cross-contamination (e.g. compared to P&T) Flexibility (different modes): DHS > FEDHS > MVM Probably the closest to SDSE & SAFE: full profile 46
47 Volatiles & Aroma Analysis: my toolbox 1. Static headspace (SHS) 2. HS-SPME (headspace) 3. Dynamic Headspace (DHS) 4. Full evaporation DHS (FEDHS) FEDHS is only technque that has the potential to provide profiles identical to liquid injection. 5. Multi Volatile Method (MVM) Remark: more trapping = more difficult desorption and slower injection Need for additional focussing?
48 Quid Semi-Volatiles? Often other chromatographic conditions required/used. How much enrichment needed? Method selection 1. (micro-) Liquid-liquid extraction (in-vial extraction) 2. SBSE (immersion!!!) 3. Solid phase extraction (SPE) 4. FEDHS???
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