Beyond Thermal Desorption: automated solutions for pyrolysis
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1 Beyond Thermal Desorption: automated solutions for pyrolysis 4 th Stir Bar Sorptive Extraction Technical Meeting September 18-19, Paris Frank David
2 Method Selection in Chromatography MW GPC GFC pyrolysis HPLC CE GC IC derivatisation Polarity
3 Pyrolysis Goal: Analyse non-volatile (high molecular weight) compounds (by GC) Polymer characterization Classical systems Filament Curie-point Micro-furnace (remark: CIS 6 PTV goes up to 600 C) Alternative approaches Combined with thermal desorption (extension of TD) What about pyrolysis + HPLC? 3
4 Gerstel PYRO Solution 1: TDU Pyrolysis (TDU-P) GC/MS Thermal Desorption Unit MPS Autosampler Pyrolysis Module with Sample Transport Adapter inserted
5 TDU-P for Automated Pyrolysis
6 TDU Pyrolysis technical features Pyrolysis temp. adjustable from 350 C to 1000 C Quick conversion between TDU and Pyrolysis Completely heated sample pathway avoids carry-over Pt Filament with 4 conductor technology avoids temperature dependency from quality of electrical connections
7 TDU Pyrolysis 4 different Operation Modes (1) (2) (3) (4) Pyro temp. Pyro temp. Pyro temp. Pyro temp. TDU temp. TDU temp. TDU temp. TDU temp. CIS cryofocussing or hot split CIS cryofocussing or hot split CIS cryofocussing or hot split CIS hot split normal flash pyrolysis solvent vent + flash pyrolysis derivatisation + flash pyrolysis simulation of TGA cond.
8 TDU-P: analysis of polypropylene (700 C) PP pyrolyse 1 st blank after pyro
9 Procedure for Thermal Extraction (TE)-GCMS and consecutive Pyrolysis (PYR)-GCMS with the Gerstel TDU-P 1. Sample is put in quartz sample holder (type B) 2. Quartz tub is attached to the transport adapter and put in sample rack (98 positions) 3. Tube is transported to TDU 4. TE (180 C)-GCMSD analysis = analysis of polymer additives and residual monomers 5. PYR (600 C)-GCMSD analysis = analysis of polymer (without additives)
10 Sequential Thermal Extraction Pyrolysis Nylon 11 - TE 350 C > pyrolysis 700 C 100 monomer 55 H H H H H O N H H H H H H H H H H H H H H (replib) Azacyclotridecan-2-one H H H H
11 Sequential Thermal Extraction Pyrolysis Nylon 11 - TE 350 C > pyrolysis 700 C
12 TDU-P for EGA or TGA simulation Pyrolyzer Temperature PYRO Thermal Desorption Unit (TDU) Cooled Injection System (CIS) TDU CIS / PTV: hot split analyte transfer duration: 60 min Time connection to MSD with non-coated transfer capillary
13 Response Polystyrene Standard Check (MW 1,080,000) EGA Simulation 418 C 410 C 450 C Temperature C
14 Response Kraton D1111K Polystyrene/isoprene C C 520 C Temperature C Recommended Pyrolysis Temperature 520 C
15 Kraton D1111K: Total Ion Chromatogram Abundance 2.3e e e+07 2e e e e e e e e e e+07 1e Time--> TIC: _04.D\data.ms Averaged mass spectrum Abundance natural rubber m/z--> Abundance polystyrene m/z-->
16 Oxidative PYROLYSIS V1 V2 Air 4 He GC 2 MSD 3 TDS-PM1 controller 4 TDS-PM1 pyrolyzer
17 PYR-CGC-MS - polystyrene Peak Number Compound 1 tetrahydrofuran 2 toluene 3 ethylbenzene 4 xylene 5 styrene Abundance (*10-3 ) methylstyrene 10 1H-indene diphenylmethane 15 butylated hydroxytoluene 16 1,2-diphenylethane 17 9,10-dihydrophenanthrene 18 stilbene 19 styrene dimer 20 2-methylstilbene ,4-diphenyl-1,3-butadiene 24 styrene dimer derivative Time (min) 31 styrene trimer Polystyrene: TIC
18 OxPYR-CGC-MS - polystyrene Peak Number Compound 1 tetrahydrofuran 2 toluene 3 ethylbenzene 4 xylene 5 styrene 6 benzaldehyde Abundance (*10-3 ) phenol methylstyrene 9 phenylacetaldehyde 10 1H-indene acetophenone 12 3-phenyl-2-propenal phenyl-2-propenol diphenylmethane 15 butylated hydroxytoluene 16 1,2-diphenylethane 17 9,10-dihydrophenanthrene stilbene 19 styrene dimer methylstilbene ,3-diphenyl-1H-pyrazole ,4-diphenyl-1,3-butadiene ,2-diphenylethandedione styrene dimer derivative ,3-diphenylbuten-1-al ,3-diphenyl-2-propen-1-one 27 1,3-diphenylbutenal isomer 0 28 oxygenated styrene dimer derivative oxygenated styrene dimer derivative Time (min) 30 oxygenated styrene dimer derivative 31 styrene trimer 32 oxygenated styrene trimer derivative Polystyrene: TIC
19 Thermochemolysis: pyrolysis and derivatisation carboxylic acids: methylation with TMAH 19
20 FAME (I) FAME (VI) FAME (II) FAME (III) FAME (IV) FAME (V) FA (I) FA (II) FA (III) FA (V) Eocene Amber: pyrolysis without/with TMAH x106 3,5 3 2,5 2 1,5 1 0,5 Pyrolysis-GC-MS x106 4 Thermochemolysis-GC-MS Counts vs. Acquisition Time (min)
21 Gerstel PYRO Solution 2: PyroVial NEW!!!! 21
22 Development of a new pyrolysis RIC Development of a generic pyrolysis interface for GC, LC, SFC, CE NEW Flexible Easy to use Compatible with available instrumentation Fully automated
23 PyroVial Insert vial 17 Body Pt filament 10 Bottom part with ring electrodes
24 PyroVial Calibration Temperature profiles Temperature ( C) Temperature profiles inside PyroVial RSD=1.5% RSD=3.3% Set point ( C) Time (sec) *RSD% expressed for 5 different vials
25 Repeatability Lignin 3 mg HYDROLIC LIGNIN 650 C (5 sec) Liquid desorption with 100 µl MeOH Injection: 2 µl split 1:5 Column: 30 m x 250 µm I.D., 0.25 µm df HP5MS 1 2 3
26 Gas & Liquid injection + Addition of solvent/reagent
27 Example: polyethylene via headspace + liquid injection Gas phase C16 Liquid desorption of rest fraction C12
28 Possibilities for Automated Analysis BEFORE PYROLYSIS Exchange of headspace gas (He, O 2, H 2 ) AFTER PYROLYSIS Gas phase recovery HS injection Addition of reagents/catalysts Liquid desorption of pyrolysate GC, LC... Addition of IS or marker Addition of reagents Fraction collection in PyroVial Addition of IS
29 Catalytic Hydrogenation 4 x10 1,2 1 0,8 0,6 + TIC Scan LDPE_900_He_LIQ_SIM_01.D alkadiene alkene alkane 100 µg LDPE He environment 0,4 0,2 0 4 x10 1,2 1 0,8 + TIC Scan LDPE_900_PdCH2_SIM_LIQ02.D alkane 100 µg LDPE + 4 mg Pd/C H2 environment 0,6 0,4 0,2 0 14,2 14,4 14,6 14, ,2 15,4 15,6 15, ,2 16,4 16,6 16, ,2 17,4 Counts vs. Acquisition Time (min)
30 In-situ Derivatisation Pyr-GCMS PET x107 1,4 1,2 1 + TIC Scan PyroVial01_PET04.D mg PET (+ 5 µl TMAH (25% solution in MeOH)) 650 C (5 sec) Liquid desorption with 100 µl MeOH Injection: 1 µl split 1:5 Column: 30 m x 250 µm I.D., 0.25 µm df HP5MS 0,8 0,6 0,4 0,2 1 2 x TIC Scan PyroVial01_PET02.D Acetophenone 2. Benzoic acid 3. Acetylbenzoic acid 4. Terephthalic acid, monomethyl ester 5. Benzoic acid, methyl ester 6. Terephthalic acid, dimethyl ester Counts vs. Acquisition Time (min)
31 Post-Pyrolysis Derivatisation Cellulose x ,5 5 4,5 4 3,5 3 2,5 2 1,5 1 0,5 No derivatisation + TIC Scan PyroVial01_CELL01.D mg CELLULOSE 500 C (5 sec) µl MSTFA/TMCS 60 C) Liquid desorption with 100 µl MeOH Injection: 1 µl, split 1:5 Column: 30 m x 250 µm I.D., 0.25 µm df HP5MS 1. Furfural 2. 1,4:3,6-dianhydro-a-D-glucopyranose 3. 1,6-anhydro-b-D-glucopyranose (levoglucosan) 4. 1,6-anhydro-b-D-glucofuranose x10 8 1,2 1 Post-pyrolysis derivatisation + TIC Scan PyroVial01_CELL02.D 5. Levoglucosan, triotms 6. b-d-glucofuranose, pentaotms 0,8 0,6 5 0,4 0, Counts vs. Acquisition Time (min)
32 Post-Pyrolysis Derivatisation Differentiation of cellulose and amylose Cellulose Amylose
33 Complementary analytical techniques GC/MS (HS or LD) LC/MS 5 mg Tryptophan 700 C (10 sec) O OH NH 2 N H
34 PYR-HS-GC/MSD Gas phase recovery (500 µl) Injection: split 1:10 Column: 50 m x 200 µm I.D., 0.5 µm df PONA MSD: Scan CO2,N2 2. acetonitrile 3. 2-propenentrile 4. propanenitrile 5. benzene 6. toluene 7. styrene 8. quinoline 9. indole and 6-methyl-1H-indole 11. trimethylbenzonitriles dimethyl-1h-indoles 4-methylquinoline 12. dimethylquinoline 13. 5,6,7-trimethyl-1H-indole
35 PYR-LD-GC/MSD Liquid desorption (200 µl AcCN) Injection: split 1:10 Column: 50 m x 200 µm I.D., 0.5 µm df PONA MSD: Scan 8. quinoline 9. indole and 6-methyl-1H-indole 11. trimethylbenzonitriles dimethyl-1h-indoles 4-methylquinoline 12. dimethylquinoline 13. 5,6,7-trimethyl-1H-indole 14. 2,3,4,9-tetrahydro-1-me-1Hpyrido[3,4-b]indole 15. Quinolinic 16. dimethyl-quinolinecarbonitrile 17. Indolic 18. Quinolinic
36 PYR-LD-LC/UV/MSD Liquid desorption 100 µl AcCN, dil 100µL H20 Injection: 2µL Column: C-18, 3.0 mm I.D., 100 mm L, 3 µm dp Eluens: (A) 0.1% HOAc, (B) AcCN MSD: (+)ESI 210 nm GC amenable LC amenable (+) ESI-MSD C2/C3-1H Indoles / C2-quinolines
37 Pyrolysis followed by HPLC High Resolution Accurate Mass Q-TOF MS for the study of Maillard reaction intermediates.
38 Pyrolysis of proline + glucose GC-MS
39 Glucose Proline Glucuronic acid 1-Acetylpyrrolidine mass 1-deoxy-1-prolinoβ-D-fructose Pyrolysis of proline + glucose LC-QTOF a. x c b. 0 x min retention time (min) min
40 m/z m/z m/z m/z Pyrolysis of Tobacco leaf extract LC-QTOF a. 500 b min min before pyrolysis after pyrolysis c Asparagine Aspartic acid Glucose Proline d Indole min min downregulated upregulated
41 Compatibility Score: Deoxy-1-[2-(3-pyridyl)-1-pyrrolidinyl]-β-D-fructose isomers Peak 1 Peak 2 HO O HO OH O HO OH O N N N N N OH N N N HO OH N OH N N N HO O N OH N
42 Conclusions Hyphenated to all separation techniques Pre- and post-pyro options Flexible and ease-of-use Fully automated Compatible with available instrumentation
43 Acknowledgements RIC team: Bart Tienpont, Rik Slosse, Christophe Devos Gerstel GmbH: Eike Kleine-Benne, Yunyun Nie, Dirk Bremer, Fred Schwartzer On Gerstel booth 43
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