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Naphthenic acids research
Matthew S. MacLennan
Chen Lab Group Meeting
March 03, 2014
Outline
• What are Naphthenic acids
again?
• What Cai has tried
• What I have tried
• What I plan to try
Concept of Naphthenic acids
Rogers, V. V; Liber, K.; MacKinnon, M. D. Chemosphere 2002, 48, 519–527.
Headley, J. V.; McMar...
Headley, J. V. et al.
J. Environ. Sci. Health. A. Tox. Hazard.
Subst. Environ. Eng. 2013, 48, 1145–
1163.
R = alkyl group
...
I have forgotten what naphthenic acids
were...
• Oil sands process (affected) water (OSPW)
• Acidified with H2SO4 to pH 2-...
What Cai has tried
• Acidify native sample
• Extract into EtOAc (dry sample)
• Perform NHS-EDC derivatization in DMSO
• In...
EDC-NHS coupling
R
O
O H
EDC-NHS
R
O
NH
N
CH3
CH3
N
CH3
CH3
NH2
DMSO
OH2
EDC-NHS coupling
http://www.piercenet.com/instructions/2160650.pdf
Sample chromatogram
What I have tried
• Sample induced transient isotachophoresis
(tITP) of aqueous derivatized CNLR OSPW (vial
5)
• tITP of a...
Aqueous EDC-Sulfo-NHS coupling
R
O
O H
EDC, Sulfo-NHS
R
O
NH
N
CH3
CH3
N
CH3
CH3
NH2
buffered H2O, pH ~ 7.5
OH2
Aqueous EDC-Sulfo-NHS coupling
http://www.piercenet.com/instructions/2160650.pdf
Acidified derivatized Syn OSPW
Acidified derivatized Syn OSPW
Scan 505 – Suspect peak
Scan 505; m/z 100-400
Scan 505; m/z 450-700
Scan 505; m/z 700-1000
Acidified derivatized CNLR OSPW
tITP injection
Scan 506 – Suspect peak
Scan 506; m/z 150-1400
1093.7
1125.2
1125.9
1138.9
1140.9
1153.5
157.7
169.7
201.7
250.8
268.4
280.0
283.6
290.1
295.8
305...
What I plan to try
• Activation of NAs with NHS or Sulfo-NHS (UV
active); Dry-stable
• Fischer esterification with MeOH-HC...
20140324   matthew - naphthenic acids
20140324   matthew - naphthenic acids
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20140324 matthew - naphthenic acids

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20140324 matthew - naphthenic acids

  1. 1. Naphthenic acids research Matthew S. MacLennan Chen Lab Group Meeting March 03, 2014
  2. 2. Outline • What are Naphthenic acids again? • What Cai has tried • What I have tried • What I plan to try
  3. 3. Concept of Naphthenic acids Rogers, V. V; Liber, K.; MacKinnon, M. D. Chemosphere 2002, 48, 519–527. Headley, J. V.; McMartin, D. W. J. Environ. Sci. Heal. Part A 2004, 39, 1989–2010.
  4. 4. Headley, J. V. et al. J. Environ. Sci. Health. A. Tox. Hazard. Subst. Environ. Eng. 2013, 48, 1145– 1163. R = alkyl group X = COOH, R, OH, Sox, Nox, SH Y = C, S, N Note: ring structures may not be fully saturated.
  5. 5. I have forgotten what naphthenic acids were... • Oil sands process (affected) water (OSPW) • Acidified with H2SO4 to pH 2-2.5 • Extracted into organic phase (DCM, EtOAc, hexanes) and dried to form film • Film reconstituted in solvent of choice for further preprocessing • = Naphthenic acids fraction compounds (NAFCs)
  6. 6. What Cai has tried • Acidify native sample • Extract into EtOAc (dry sample) • Perform NHS-EDC derivatization in DMSO • Inject reaction mixture into CE-MS with 1% HCOOH/50% MeOH acidic buffer • (PrO)3Si(PEI) coated capillary for EOF
  7. 7. EDC-NHS coupling R O O H EDC-NHS R O NH N CH3 CH3 N CH3 CH3 NH2 DMSO OH2
  8. 8. EDC-NHS coupling http://www.piercenet.com/instructions/2160650.pdf
  9. 9. Sample chromatogram
  10. 10. What I have tried • Sample induced transient isotachophoresis (tITP) of aqueous derivatized CNLR OSPW (vial 5) • tITP of aqueous derivatized Syn OSPW (vial 4)
  11. 11. Aqueous EDC-Sulfo-NHS coupling R O O H EDC, Sulfo-NHS R O NH N CH3 CH3 N CH3 CH3 NH2 buffered H2O, pH ~ 7.5 OH2
  12. 12. Aqueous EDC-Sulfo-NHS coupling http://www.piercenet.com/instructions/2160650.pdf
  13. 13. Acidified derivatized Syn OSPW
  14. 14. Acidified derivatized Syn OSPW
  15. 15. Scan 505 – Suspect peak
  16. 16. Scan 505; m/z 100-400
  17. 17. Scan 505; m/z 450-700
  18. 18. Scan 505; m/z 700-1000
  19. 19. Acidified derivatized CNLR OSPW tITP injection
  20. 20. Scan 506 – Suspect peak
  21. 21. Scan 506; m/z 150-1400 1093.7 1125.2 1125.9 1138.9 1140.9 1153.5 157.7 169.7 201.7 250.8 268.4 280.0 283.6 290.1 295.8 305.4 536.3 551.3 560.6 575.7 589.5 604.2 804.5 828.5 842.7 856.6 872.0 886.7
  22. 22. What I plan to try • Activation of NAs with NHS or Sulfo-NHS (UV active); Dry-stable • Fischer esterification with MeOH-HCl; CE-ESI- MS – Commonly used derivatization in lipidomics – Good for fragmentation

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