Effect of thermal treatment on acidic organic species from athabasca bitumen heavy vacuum gas oil, analyzed by negative-ion electrospray fourier transform ion cyclotron resonance (FT-ICR) mass spectrometry

Energy and Fuels

Volumn 23, Issue 1, 2009, Pages 314-319

  Smith, Donald F ^a,b,c   Rodgers, Ryan P ^a,b,c   Rahimi, Parviz ^a,b,c   Teclemariam, Alem ^a,b,c   Marshall, Alan G ^a,b,c  

^a FLORIDA STATE UNIVERSITY   (United States)

^b FLORIDA STATE UNIVERSITY   (United States)

^c NATIONAL CENTRE FOR UPGRADING TECHNOLOGY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACID DECOMPOSITIONS; ATHABASCA BITUMENS; CARBON NUMBER DISTRIBUTIONS; CARBON NUMBERS; COMPOSITIONAL CHANGES; CORE STRUCTURES; DOUBLE BONDS; FOURIER TRANSFORM ION CYCLOTRON RESONANCE MASS SPECTROMETRIES; HEAVY VACUUM GAS OIL; HETERO ATOMS; HIGHER TEMPERATURES; ION ELECTROSPRAY; ION ELECTROSPRAY IONIZATIONS; LIQUID PRODUCTS; MOLECULAR TRANSFORMATIONS; NAPHTHENIC ACIDS; ORGANIC SPECIES; RELATIVE ABUNDANCES; SWEEP GAS; THERMAL TREATMENTS; TOTAL ACID NUMBERS; TREATMENT TEMPERATURES;

ATMOSPHERIC TEMPERATURE; BITUMINOUS MATERIALS; CARBOXYLIC ACIDS; CONDENSERS (LIQUEFIERS); CYCLOTRONS; DISTILLATION; ELECTRON CYCLOTRON RESONANCE; ELECTROSPRAY IONIZATION; FLUID CATALYTIC CRACKING; GAS OILS; GASES; HEAT TREATMENT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IONIZATION OF GASES; LIQUIDS; MASS SPECTROMETERS; MASS SPECTROMETRY; NEGATIVE IONS; ORGANIC ACIDS; PLASMAS; RESONANCE; SPECTRUM ANALYSIS; TANNING; VACUUM; VACUUM PUMPS;

FOURIER TRANSFORMS;

EID: 64249161508     PISSN: 08870624     EISSN: None     Source Type: Journal    
DOI: 10.1021/ef8005564     Document Type: Article

References (44)

1. Berkowitz, N.; Speight, J. G. Oil sand of Alberta. Fuel 1975, 54 (3), 138-149.
2. Turnbull, A.; Slavcheva, E.; Shone, B. Factors controlling naphthenic acid corrosion. Corrosion 1998, 54(11), 922-930.
3. Slavcheva, E.; Shone, B.; Turnbull, A. Review of naphthenic acid corrosion in oil refining. Br. Corros. J. 1999, 34(2), 125-131.
4. Laredo, G. C.; Lopez, C. R.; Alvarez, R. E.; Cano, J. L. Naphthenic acids, total acid number and sulfur content profile characterization in Isthmus and Maya crude oils. Fuel 2004, 83 (11-12), 1689-1695.
5. Laredo, G. C.; Lopez, C. R.; Alvarez, R. E.; Castillo, J. J.; Cano, J. L. Identification of naphthenic acids and other corrosivity-related characteristics in crude oil and vacuum gas oils from a Mexican refinery. Energy Fuels 2004, 18, 1687-1694.
6. Yu, S. K. T.; Green, J. B. Determination of total hydroxyls and carboxyls in petroleum and syncrudes after chemical derivatization by infrared spectroscopy. Anal. Chem. 1989, 61 (11), 1260-1280.
7. Rudzinski, W. E.; Oehlers, L.; Zhang, Y. Tandem mass spectrometric characterization of commercial naphthenic acids and a maya crude oil. Energy Fuels 2002, 16, 1178-1185.
8. Tomczyk, N. A.; Winans, R. E.; Shinn, J. H.; Robinson, R. C. On the nature and origin of acidic species in petroleum. 1. Detailed acid type distribution in a california crude oil. Energy Fuels 2001, 15 (6), 1498-1504.
9. Seifert, W. K.; Teeter, R. M. Identification of polycyclic aromatic and heterocyclic crude oil carboxylic acids. Anal. Chem. 1970, 42 (7), 750-758.
10. Hao, C.; Headley, J. V.; Peru, K. M.; Frank, R.; Yang, P.; Solomon, K. R. Characterization and pattern recognition of oil-sand naphthenic acids using comprehensive two-dimensional gas chromatography/time-of-flight mass spectrometry. J. Chromatogr., A 2005, 1067, 277-284.
11. St. John, W. P.; Rughania, J.; Green, S. A.; McGinnisa, G. D. Analysis and characterization of naphthenic acids by gas chromatography-electron impact mass spectrometry of tert-butyldimethylsilyl derivatives. J. Chromatogr., A 1998, 807, 241-251.
12. Holowenko, F. M.; MacKinnonb, M. D.; Fedorak, P. M. Characterization of naphthenic acids in oil sands wastewatersbygas chromatography-mass spectrometry. Water Res. 2002, 36, 2843-2855.
13. Clemente, J. S.; Prasad, N. G. N.; MacKinnon, M. D.; Fedorak, P. M. A statistical comparison of naphthenic acids characterized by gas chromatography-mass spectrometry. Chemosphere 2003, 50, 1265-1274.
14. Hsu, C. S.; Dechert, G. J.; Robbins, W. K.; Fukuda, E. K. Naphthenic acids in crude oils characterized by mass spectrometry. Enegry Fuels 2000, 14 (1), 217-223.
15. Fan, T. Characterization of naphthenic acids in petroleum by fast atom bombardment mass spectrometry. Enegry Fuels 1991, 5, 371-375.
16. Dzidic, I.; Somerville, A. C.; Raia, J. C.; Hart, H. V. Determination of naphthenic acids in California crudes and refinery wastewaters by fluoride ion chemical ionization mass spectrometry. Anal. Chem. 1988, 60 (13), 1318-1323.
17. Hsu, C. S.; Liang, Z.; Campana, J. E. Hydrocarbon characterization by ultrahigh resolution Fourier transform ion cyclotron resonance mass spectrometry. Anal. Chem. 1994, 66 (6), 850-855.
18. Zhan, D. L.; Fenn, J. B. Electrospray mass spectrometry of fossil fuels. Int. J. Mass Spectrom. 2000, 194 (2-3), 197-208.
19. Qian, K.; Robbins, W. K.; Hughey, C. A.; Cooper, H. J.; Rodgers, R. P.; Marshall, A. G. Resolution and identification of elemental compositions for more than 3000 crude acids in heavy petroleum by negative-ion microelectrospray high-field Fourier transform ion cyclotron resonance mass spectrometry. Energy Fuels 2001, 15 (6), 1505-1511.
20. Hughey, C. A.; Rodgers, R. P.; Marshall, A. G.; Qian, K.; Robbins, W. K. Identification of acidic NSO compounds in crude oils of different geochemical origins by negative ion electrospray Fourier transform ion cyclotron resonance mass spectrometry. Org. Geochem. 2002, 33 (7), 743-759.
21. Stanford, L. A.; Kim, S.; Klein, G. C.; Smith, D. F.; Rodgers, R. P.; Marshall, A. G. Identification of water-soluble heavy crude oil organicacids, bases, and neutrals by electrospray ionization and field desorption ionization Fourier transform ion cyclotron resonance mass spectrometry. Environ. Sci. Technol. 2007, 41 (8), 2696-2702.
22. Stanford, L. A.; Kim, S.; Rodgers, R. P.; Marshall, A. G. Characterization of compositional changes in vacuum gas oil distillation cuts by electrospray ionization Fourier transform-ion cyclotron resonance (FT-ICR) mass spectrometry. Energy Fuels 2006, 20 (4), 1664-1673.
23. Stanford, L. A.; Rodgers, R. P.; Marshall, A. G.; Czarnecki, J.; Wu, X. A.; Taylor, S. Detailed elemental compositions of emulsion interfacial material versus parent oil for nine geographically distinct light, medium, and heavy crude oils, detected by negative- and positive-ion electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry. Energy Fuels 2007, 21 (2), 973-981.
24. Purcell, J. M.; Hendrickson, C. L.; Rodgers, R. P.; Marshall, A. G. Atmospheric pressure photoionization Fourier transform ion cyclotron resonance mass spectrometry for complex mixture analysis. Anal. Chem. 2006, 78 (16), 5906-5912.
25. Smith, D. F.; Schaub, T. M.; Rahimi, P.; Teclemariam, A.; Rodgers, R. P.; Marshall, A. G. Self-association of organic acids in petroleum and Canadian bitumen characterized by low- and high-resolution mass spectrometry. Energy Fuels 2007, 21 (3), 1309-1316.
26. Blum, S. C.; Olmstead, W. N. Viscosity reduction by heat soakinduced naphthenic acid decomposition in hydrocarbon oils. U.S. Patent 5,976,360, April 24, 1997.
27. Blum, S. C.; Olmstead, W. N.; Bearden, R., Jr. Thermal decomposition of naphthenic acids. U.S. Patent 5,820,750, Feb 9, 1996.
28. Marshall, A. G.; Hendrickson, C. L.; Jackson, G. S. Fourier transform ion cyclotron resonance mass spectrometry: A primer. Mass Spectrom. Rev. 1998, 17 (1), 1-35.
29. Marshall, A. G.; Rodgers, R. P. Petroleomics: The next grand challenge for chemical analysis. Acc. Chem. Res. 2004, 37 (1), 53-59.
30. Rodgers, R. P.; Schaub, T. M.; Marshall, A. G. Petroleomics: MS returns to its roots. Anal. Chem. 2005, 77 (1), 20A-27A.
31. American Society for Testing and Materials (ASTM). ASTM Standard D1160-03. In Standard Test Method for Distillation of Petroleum Products at Reduced Pressure; ASTM International: West Conshohocken, PA, 2003.
32. American Society for Testing and Materials (ASTM). ASTM Standard D664-07. In Standard Test Method for Acid Number of Petroleum Products by Potentiometric Titration; ASTM International: West Conshohocken, PA, 2003.
33. Senko, M. W.; Canterbury, J. D.; Guan, S.; Marshall, A. G. A highperformance modular data system for FT-ICR mass spectrometry. Rapid Commun. Mass Spectrom. 1996, 10, 1839-1844.
34. Hendrickson, C. L.; Quinn, J. P.; Emmett, M. R.; Marshall, A. G. Quadrupole mass filtered external accumulation for Fourier transform ion cyclotron resonance mass spectrometry. In the 48th American Society for Mass Spectrometry Annual Conference on Mass Spectrometry and Allied Topics, Long Beach, CA, 2000; MPB 083.
35. Emmett, M. R.; White, F. M.; Hendrickson, C. L.; Shi, S. D. H.; Marshall, A. G. Application of micro-electrospray liquid chromatography techniques to FT-ICR MS to enable high-sensitivity biological analysis. J. Am. Soc. Mass Spectrom. 1998, 9 (4), 333-340.
36. Blakney, G. T.; van der Rest, G.; Johnson, J. R.; Freitas, M. A.; Drader, J. J.; Shi, S. D.-H.; Hendrickson, C. L.; Kelleher, N. L.; Marshall, A. G. Further improvements to the MIDAS data station for FT-ICR mass spectrometry, In Proceedings of the 49th American Society for Mass Spectrometry Conference on Mass Spectrometry and Allied Topics, Chicago, IL, May 2001; WPM265.
37. Ledford, E. B., Jr.; Rempel, D. L.; Gross, M. L. Space charge effects in Fourier transform mass spectrometry. Mass calibration. Anal. Chem. 1984, 56, 2744-2748.
38. Shi, S. D.-H.; Drader, J. J.; Freitas, M. A.; Hendrickson, C. L.; Marshall, A. G. Comparison and interconversion of the two most common frequency-to-mass calibration functions for Fourier transform ion cyclotron resonance mass spectrometry. Int. J. Mass Spectrom. 2000, 195/196, 591-598.
39. 2 = 14.0000 for high resolution mass spectrometry of organic compounds. Anal. Chem. 1963, 35 (13), 2146-2154.
40. Hughey, C. A.; Hendrickson, C. L.; Rodgers, R. P.; Marshall, A. G.; Qian, K. Kendrick mass defect spectroscopy: A compact visual analysis for ultrahigh-resolution broadband mass spectra. Anal. Chem. 2001, 73, 4676-4681.
41. Fu, J.; Kim, S.; Rodgers, R. P.; Hendrickson, C. L.; Marshall, A. G. Nonpolar compositional analysis of vacuum gas oil distillation fractions by electron ionization Fourier transform ion cyclotron resonance mass spectrometry. Energy Fuels 2006, 20 (2), 661-667.
42. Smith, D. F.; Schaub, T. M.; Rodgers, R. P.; Rahimi, P.; Marshall, A. G. In Characterization of acidic species from Athabasca Canadian bitumen by negative ion ESI FT-ICR MS. Oilsands 2006, Edmonton, Alberta, Canada, Feb 22-24, 2006.
43. Boto, A.; Hernandez, R.; Suarez, E.; Betancor, C.; Rodriguez, M. S. Tandem carbon-radical peroxidation-addition to carbonyl groups reaction. A new synthesis of steroidal β-peroxy lactones. J. Org. Chem. 1995, 60 (25), 8209-8217.
44. CAS Registry Number 171366-97-5. 2007 ed.