High Sensitivity Analysis of Volatile and Semi-volatile Compounds Using ASAP and GC/MS on an LC/MS Instrument
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1 High Sensitivity Analysis of Volatile and Semi-volatile Compounds Using ASAP and GC/MS on an LC/MS Instrument Charles N. McEwen DuPont Corporate Center for Analytical Sciences Wilmington, DE
2 Why is Solvent Bad for Ionization? Solvent in the gas phase limits ionization to molecules more basic than the solvent Exception is photoionization (not acid/base ionization) but still mediated by solvent Removing solvent and water vapor from ionization region increases types of compounds that can be ionized at atmospheric pressure
3 ASAP Atmospheric-pressure pressure Solids Analysis Probe A rapid method for analysis of volatile and semivolatile compounds in solids, liquids, polymers, and biological tissue
4 ASAP Ion Source N2 nebulizer gas LC connector APCI Probe LC interface probe Heated desolvation gas N2 purge in Teflon plug Melting point capillary Discharge needle MS inlet Mass Spec API source housing N 2 purge vent
5 Safety First ASAP vaporizes materials The ion source should be sealed during analysis (Just as ESI and APCI) and Vented to a hood
6 ASAP Probe
7 AP MALDI Orbitrap with ASAP ESI/APCI Source ASAP Probe
8
9 ASAP Examples Solids probe replacement Accurate mass of mixtures Analysis of polymer additives Analysis of drugs (or explosives) Analysis of biological tissue
10 Replacement for Solids Probe No vacuum lock Fast analysis MH + ions with minimal fragmentation Accurate mass MS/MS for structural information
11 ASAP on QTof Showing Instrument Calibration and 6 Steroid Samples in 3 min. Rapid solids probe analysis at atmospheric pressure of steroids cnmtest 1 a TOF MS ES+ TIC 1.26e5 PEG44 % 1.8 min 2.8 min Total Ion Current Chromatogram of ASAP analysis of 6 steroids Time Rapid solids probe analysis at atmospheric pressure of steroids cnmtest 21 (.415) Cm (21:31) 1 b TOF MS ES+ 1.27e PEG for Instrument Calibration % m/z Rapid solids probe analysis at atmospheric pressure of steroids cnmtest 132 (2.641) AM (Cen,4, 75., Ar,5.,391.28,.8) 1 c MH + -H 2 O MH + TOF MS ES+ 7.65e3 Atmospheric Pressure Mass Spectrum of Steroid % m/z Anal. Chem., 25, 77,
12 Solids Probe Sample for Accurate Mass fish tube2-asap1_ #15 RT:.89 AV: 1 SB: 1.32 NL: 3.39E7 T: FTMS + p APCI corona Full ms [ 1.-1.] C 33 H 58 P C 33 H 57 P 3 Relative Abundance C 33 H 59 P C 33 H 56 P C 36 H 55 P C 36 H 57 P C 43 H C 43 H C 37 H 54 P C 43 H C 43 H C 43 H C 43 H m/z
13 Accurate Mass Measurement for GC/MS GC/MS using low performance MS ASAP on high performance MS for elemental compositions High resolution required MS/MS with accurate mass
14 PrefumeX_ #8-18 RT: AV: 11 NL: 2.3E7 T: FTMS + p APCI corona Full ms [ 1.-8.] C 9 H 7 O 2 1 ASAP of Perfume on Orbitrap C 14 H 19 O 5 N C 14 H 23 O Relative Abundance C 14 H C 13 H 15 O 5 N C 1 H C 8 H 6 O C 11 H 14 O C 2 H C 12 H C 19 H 13 O 2 N 5 C 6 H 19 O 4 N C 17 H 3 O C 2 H 32 O C 21 H 18 N C 27 H C 25 H 35 N C 3 H 5 O m/z
15 Perfume Analysis APGCMS Perfume4 3m DB1 apciperfume4_cv32 Sm (Mn, 1x1) 1 GC/APMS TOF MS ES+ BPI 1.1e % Time
16 Abundance GC/MS of Musk Ketone Using EI, APPI, and APCI EI-MS Scan 3171 (2.49 min): chuck 2.D\data.ms 279 C 13 H 15 O 5 N O OH 3 C N CH 3 CH 3 O N O H 3 C CH O CH m/z--> Photoionization MS Perfume4 DB1 photo_perfume (12.812) 1 APPI-MS TOF MS ES+ 1.3e3 % apciperfume4_cv (12.793) 1 APCI-MS C 14 H 19 O 5 N TOF MS ES % m/z
17 PrefumeX_ #8-18 RT: AV: 11 NL: 2.3E7 T: FTMS + p APCI corona Full ms [ 1.-8.] C 9 H 7 O C 9 H 7 O 2 ASAP of Perfume on Orbitrap C 14 H 23 O 1 C 14 H 23 O C 14 H 19 O 5 N 2 C 14 H 19 O 5 N 2 6 Relative Abundance C 14 H C 14 H C 13 H 15 O 5 N C 13 H 15 O 5 N C 1 H C 8 H 6 O C 11 H 14 O C 2 H C 12 H C 19 H 13 O 2 N 5 C 6 H 19 O 4 N C 17 H 3 O C 2 H 32 O C 21 H 18 N C 27 H C 25 H 35 N C 3 H 5 O m/z
18 EPA 827 Megamix by ASAP as a Function of Time/Temperature Temperature Relative Abundance m/z Mass NL: 1.25E8 EPA827_ #59 RT: 1. AV: 1 SB: T: FTMS + p APCI corona Full m s [ 5.-1.] NL: 1.61E8 EPA827_ #45 RT:.76 AV: 1 SB: T: FTMS + p APCI corona Full m s [ 5.-1.] NL: 1.36E8 EPA827_ #34 RT:.57 AV: 1 SB: T: FTMS + p APCI corona Full m s [ 5.-1.] NL: 5.51E7 EPA827_ #23 RT:.38 AV: 1 SB: T: FTMS + p APCI corona Full m s [ 5.-1.] NL: 5.8E7 EPA827_ #11 RT:.18 AV: 1 SB: T: FTMS + p APCI corona Full m s [ 5.-1.] NL: 9.9E6 EPA827_ #5 RT:.7 AV: 1 SB: T: FTMS + p APCI corona Full m s [ 5.-1.]
19 EPA827_ #4 RT:.6 AV: 1 NL: 6.3E7 T: FTMS + p APCI corona Full m s [ 5.-1.] Relative Abundance C 6 H 8 N C 1 H 8 O 3 N 2 ASAP of Restek EPA 827 Megamix 17.5 C 7 H 7 O C 8 H C 7 H 9 O C 6 H 7 O C 9 H C 8 H 11 O C 8 H 9 O C 9 H C 6 H 15 O 1 N C 9 H 4 O C 9 H 11 O C 9 H 15 O C 11 H C 1 H 9 O C 8 H 5 O C 12 H C 12 H C 9 H 7 O C 13 H C 12 H 12 N m/z Aminobenzene 2. Phenol 3. Methylphenol 4. Dimethylphenol 5. Nitroso-di-propylamine 6. Isophorone 7. Methylnapthalene 8. Acenaphthylene 9. Diphenylamine 8 9
20 Polymer Additive Analysis Obtain additive elemental compositions in seconds No sample extraction required MS/MS for confirmation
21 MASSOUDA_1_PELLET_ #42 RT: 1.26 AV: 1 NL: 1.76E7 T: FTMS + p APCI corona Full ms [ ] ASAP of Additives in Polymer Nonwoven polymer -C 14 H 21 O C 28 H 42 O 2 P C 42 H 63 O 3 P 1 C 42 H 63 O 3 P Irgafos Relative Abundance C 42 H 63 O 4 P Erucamide C 22 H 44 ON C 27 H 4 O 4 N 1 Irgafos 168 oxidized C 8 H C 22 H 44 O 1 N 1 -C 4 H C 38 H 56 O 3 P m/z
22 ASAP of Nonwoven Fiber nonwovan_fabric_ #63 RT: 1.89 AV: 1 NL: 1.E7 T: FTMS + p APCI corona Full ms [ 1.-2.] C 42 H 63 O 3 P Erucamide 2. Fragment of 4 3. Irganox Irgafos Irgafos 168 oxidized 6. Irganox 3114 Relative Abundance C 22 H 44 O 1 N C 28 H 42 O 2 P C 35 H 62 O C 48 H 69 O 6 N m/z
23 ASAP of Drugs On objects In urine or spit without sample preparation Accurate mass MS/MS
24 ASAP of Ibuprofen Tablet Ibuprofen_ #389 RT: 2.53 AV: 1 SB: NL: 9.63E8 T: FTMS + p APCI corona Full ms [ 5.-5.] 1 C 12 H C 12 H (CH 3 ) 2 CHCH 2 C 6 H 4 CH(CH 3 )COOH Relative Abundance C 12 H C 9 H C 9 H 11 C 1 H 11 O C 1 H 11 O C C 5 H 11 4 H C 4 H C 5 H C 6 H 9 C 7 H C 7 H C 7 H 11 C 8 H C 8 H C 9 H C 1 H 9 O C 8 H 5 O C 8 H 7 O C 13 H 16 O 1 C 13 H 18 O C 13 H 19 O m/z
25 Direct ASAP Analysis of Urine Sample 9 hrs After 12 hr Sedafed cnmurin_psuedo_caf_ #33 RT: 1.5 AV: 1 SB: NL: 5.77E7 T: FTMS + p APCI corona Full ms [ 1.-1.] C 1 H 14 N HN CH 3 C 1 H 14 N 9 85 CH Relative Abundance HO HN CH 3 CH H 2 O C 9 H C 9 H 11 N 1 Ephedrine C 1 H 16 ON C 1 H 16 O 1 N C 9 H 14 O C 11 H 15 O 1 N C 11 H 17 O 2 N m/z
26 dollar_bills_ #198 RT: 1.72 AV: 1 NL: 8.56E8 T: FTMS + p APCI corona Full ms [ ] The Famous Cocaine on a Dollar Bill C 8 H 5 O 3 Phthalate C 8 H 5 O 3 Cocaine C 17 H 22 O 4 N C 17 H 22 O 4 N Relative Abundance PhCOOH C 1 H 16 O 2 N C 1 H 16 O 2 N 1 C 24 H 39 O C 24 H 39 O C 6 H 13 O C 1 H C 8 H 7 O C 12 H 25 O C 16 H 23 O C 18 H 39 O C 22 H 41 O C 22 H 41 O 4 N C 25 H 47 O 5 N m/z
27 ASAP of Biological Samples Rapid analysis of volatiles in tissue No sample preparation Accurate mass and MS/MS High resolution desirable
28 ASAP of Carrot carot_ #2 RT:.57 AV: 1 NL: 4.25E6 T: FTMS + p APCI corona Full ms [ 1.-8.] C 6 H 7 O 3 C 4 H C 4 H 56 Beta-carotene Relative Abundance C 6 H 9 O C 9 H 7 O C 15 H 15 O 5 N C 19 H 37 O C 29 H C 29 H 5 O C 21 H 37 O 3 C 13 H 11 O 3 N C 28 H 47 C 33 H C 34 H 63 O C 37 H 67 O C 39 H 68 O C 47 H 61 N C 49 H 65 O 2 N m/z
29 ASAP of Catnip Leaf Normal Growth and After Growth in Cold and Dark Normal Catnip2_ #11 RT:.16 AV: 1 NL: 6.32E6 T: FTMS + p APCI corona Full ms [ 1.-2.] C 1 H 15 O 2 1 catnip_cold_ #54 RT: 1.47 AV: 1 NL: 1.1E8 T: FTMS + p APCI corona Full ms [ 5.-1.] 1 nepetalactone C 1 H 15 O C 2 H 42 N C 28 H 45 O1 N 3 Cold and Dark 95 9 C 1 H 15 O H 3 C O O Relative Abundance Relative Abundance C 9 H C 1 H 13 O 1 CH C 9 H C 1 H 13 O C 14 H C 14 H 21 O1 N C 2 H 39 N C 2 H 46 O1 N C 27 H 45 N C 29 H C 28 H 47 O2 N 3 C 18 H 38 N C 3 H 63 O1 N 3 C 35 H 67 O3 N m/z C 14 H 29 O C 16 H 33 O C 18 H 37 O C 3 H 51 C 22 H 19 O C 33 H C 37 O 3 N C 42 O 3 N m/z
30 Ergosterol Biosynthesis Squalene 2,3-Oxidosqualene Lanosterol Eburicol O Squalene Epoxidase H O Epoxysqualene Cyclase H O C24 Transmethylase H O C14 Demethylase C4 Demethylase H O C14 Reductase Ergosterol Fecosterol H O H O C22 Desaturase C5 Desaturase C24(28) Reductase Δ8 Isomerase
31 ASAP of Fungus Cells AG_FUNGUS_CONTROL_S_ #22 RT:.65 AV: 1 SB: NL: 1.5E5 T: FTMS + p APCI corona Full ms [ 2.-1.] Untreated Internal standard C 28 H 44 O 1 Ergosterol Relative Abundance C 24 H 39 O 4 H O C 25 H C 24 H 48 O C 27 H C 28 H 48 O C 28 H C 31 H 52 O C 28 H C 3 H 49 O C 3 H 5 O C C 28 H H 4 C 3 H C 3 H 61 C 31 H 63 C 32 H m/z AG_FUNGUS_H6573_S_ #25 RT:.73 AV: 1 SB: NL: 3.85E4 T: FTMS + p APCI corona Full ms [ 2.-1.] C 24 H 39 O Treated with Inhibitor Eburicol C 31 H 52 O C 3 H 49 O 1 RelativeAbundance C 24 H 48 O 2 HO C 29 H 47 O C 26 H 51 O C 23 H 46 O C 25 H 49 O C 22 H 43 O C 3 H C 28 H 45 O C 31 H C 26 H 43 O C 31 H 5 O C 31 H 48 O C 28 H 47 O m/z
32 ASAP of Treated Fungus AG_FUNGUS_JP355_S_ #23 RT:.6 AV: 1 SB: NL: 2.53E5 T: FTMS + p APCI corona Full ms [ 2.-1.] 1 Inhibitor added Lanosterol C 29 H 47 O C 3 H 5 O RelativeAbundance C 27 H 42 O C 24 H 48 O C 24 H 39 O 4 C 29 H 49 O C 28 H 45 O C 3 H C 27 H 4 O C 3 H 48 O 1 C 3 H 5 O 2 5 C 26 H 48 C 27 H 5 C 28 H 52 C 29 H C 31 H m/z AG_FUNGUS_YB837_S_ #23-27 RT: AV: 5 SB: NL: 4.52E5 T: FTMS + p APCI corona Full ms [ 2.-1.] C 24 H 48 O 2 1 Inhibitor added S IS Ignosterol ES C 28 H 46 O HO RelativeAbundance HO C 25 H 52 O C 24 H 46 O 4 N C 26 H 44 C 28 H 48 C H 46 O 6 N C 25 H 48 O 5 C 25 H 5 O 4 C 21 H 46 O 4 N C 29 H 46 O C 27 H 49 C 23 H 41 O 2 N C 27 H 52 O m/z
33 ASAP Probe for DESI Analysis of nonvolatiles such as peptides and proteins Patented technology
34 Sigma Peptide Mixture by ASAP Probe DESI SIGMAPEP_ESI_ #19 RT: 3.42 AV: 1 NL: 5.56E4 T: FTMS + p ESI Full ms [ ] Ang III Single Acquisition LeuEnk Relative Abundance Ang III MetEnk m/z
35 Myoglobin by ASAP Probe DESI XtractTemp_ /1/26 4:23:46 PM RT: Relative Abundance Myo Total Ion Chromatogram Myo NL: 6.21E6 TIC M S CYTOC_E SI_ Time (min) CYTOC_ESI_ # 28 RT:.73 AV: 1 NL: E4 T: FTM S + p ESI Full ms [ ] Single Acquisition Relative Abundance m/ z XtractTemp_ # 1 RT: 1. AV: 1 NL: E3 T: FTM S + p ESI Full ms [ ] Deconvoluted molecular ion envelope Relative Abundance m/ z
36 Conclusions ASAP is a rapid method for Analysis of Samples at Atmospheric Pressure ASAP is compatible with LC/MS and AP GC/MS and requires only a simple ion source modification Volatile and semivolatile compounds in solids, liquids, polymers, and biological tissue can be analyzed in seconds The method is especially powerful on high performance mass spectrometers
37 GC/MS on an LC/MS Instrument o Atmospheric Pressure Ionization (API) has primarily been interfaced with liquid chromatography, but it is also an ionization method that can be applied to gas chromatograph. o Any LC/MS instrument can also be used as a GC/MS instrument. o Either APCI or APPI can be used
38 LC/MS Ion Source: GC Interface Probe Replaces LC Probe Purge gas entrance GC Interface probe Advantages over LC/MS O GC provides higher chromatographic resolution and more peak capacity than LC. O Higher sensitivity for certain compounds. O Less problems with analyte solubility. HV Discharge needle Ground plate Purge gas exit Mass Spec Advantages over vacuum GC/MS O Uses high performance LC/MS instrumentation O Mass selected fragmentation for GC/MS Quantitation
39 Waters QTof Agilent GC With autosampler
40 Interface probe Syagen Photoionization Source
41 K25-574A 1 Perfume Analysis: Comparison of UV, LC/MS, GC/APMS UV Diode Array : Diode Array TIC 6.53e7 % K25-574A 1 LC/MS Electrospray : TOF MS ES+ TIC 1.23e % Time A P G C M S P e r f u m e 4 3 m D B 1 a p c ip e r fu m e 4 _ c v 3 2 S m ( M n, 1 x 1 ) T O F M S E S B P I 1.1 e GC/APCI MS % T im e
42 Molecular and MH + Ion Generation A + e ---> A+. + 2e (EI) A + hν ---> A+. + e (APPI) A+. + H2O ---> AH+ +.OH N2 + e ---> N e (APCI) N N2 ---> N4+. + N-2 N4+. + H2O ---> H2O+. + 2N2 H2O+. + H2O ---> H3O+ +.OH H3O+ + A ---> AH+ + H2O N2+./N4+. + A ---> A+. + xn2
43 Comparison of AP GC/MS of n-butyrophenone Using APPI and APCI Photoionization MS photomix1 3m DB1 photo_mix1_cv (7.196) 1 Photoionization n-butyrophenone Odd-electron fragment ions TOF MS ES+ 434 % APGCMS photomix1 3m DB1 apcimix1cv32 53 (7.192) APCI n-butyrophenone MH + fragment ions m/z TOF MS ES+ 1.15e3 % m/z
44 photoperfume4_cv33 1 APPI 9.8 ev Perfume Analysis by API-GC/MS 1)Rose oil 2) Linalool 3) C14H12 4) Geraniol 5) Dimethyl-2,6-octadien-1-ol 6) Vanillin 7) Ionone 8) Coumarin 9)Cetone 1) Dimethoxypropenylbenenee 11) Isomethylionine 12) Diethylphthalate 13) Methyltetradecanoic acid 14) Methylpentadecanone 15) Musk Ketone 16) Civetone TOF MS ES+ BPI 693 % photo_perfume4 1 APPI 1.6 ev TOF MS ES+ BPI 1.52e3 % apciperfume4_cv32 1 APCI % TOF MS ES+ BPI 1.49e Time
45 APPI Spectra of Isomers of methyl-ionone Photoionization MS Perfume4 DB1 photo_perfume4 114 (9.964) 1 O TOF MS ES+ 392 % Photoionization MS Perfume4 DB m/z photo_perfume4 936 (9.172) TOF MS ES e % H 3 C CH 3 CH 3 O CH CH m/z
46 Abundance 45 Electron Impact Spectra of Methyl-ionone Isomers Scan 2424 ( min): chuck 2.D\data.ms 191 O Abundance Scan ( min): 15chuck D\data.ms m/z--> CH 3 O CH 3 H 3 C 2 15 CH CH m/z-->
47 Abundance Comparison of Electron Impact to APPI Spectra of Benzopyran-2-one 9 8 EI Scan 2182 ( min): chuck 2.D\data.ms m/z--> 1 APPI TOF MS ES+ 256 % m/z
48 GC/APMS Restek 827 EPA Mixture APGCMS Restek APCI apci833cv % APCI APGCMS Restek 833 APCI apci833cv33 49 (5.577) 1 % Nitrobenzene TOF MS ES+ 1.29e m/z APGCMS Restek 833 APCI apci833cv33 1 % photo833_cv32 1 % TOF MS ES+ BPI 1.42e Time TOF MS ES+ BPI 1.47e3 TOF MS ES+ BPI 537 photo833_cv APPI 9.8 ev 827 Photoionization MS Restek833 3m DB1 photo833_cv32 57 (6.38) TOF MS ES Dichlorophenol TOF MS ES+ BPI 1.1e3 % % m/z Time
49 Reproducibility Study Restek 827 Megamix by GC/1.6 ev APPI-MS photo8271megamix3 1 Peak width 1.5 sec.5 sec acquisition TOF MS ES+ BPI 1.76e3 % photo8271megamix2 1 TOF MS ES+ BPI 1.73e3 % Time
50 Conclusion o AP-GC/MS extends the capabilities of LC/MS instrumentation. o APPI GC/MS is almost a universal ionization method for volatile compounds. o High sensitivity. o Library search possible with APPI? o Positive/negative ionization, accurate mass, MS/MS, quantitation. o This work has shown that LC/MS instrumentation can be made more powerful and more universal by incorporating the ability to also perform AP GC/MS.
51 Additional Information ASAP: McEwen, McKay, Larsen Anal. Chem., 25, 77, AP GC/MS: McEwen, McKay J. Am. Soc. Mass Spectrom., 25, 16,
52 Acknowledgements Richard G. McKay Barbara S. Larsen Patricia M. Peacock DuPont Corporate Center for Analytical Sciences Waters Corporation (Michael Balogh)
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