Asphaltenes, Heavy Oils, And Petroleomics,9780387317342

Asphaltenes, Heavy Oils, And Petroleomics

by ; ; ;
Edition: 1st
ISBN13: 9780387317342
ISBN10: 0387317341
Format: Hardcover
Pub. Date: 2006-12-30
Publisher(s): Springer Nature
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Summary

With substantial contributions from experienced University and industrial scientists and engineers, this work will have real application towards improving process efficiency and improvement in the trillion-dollar global petroleum industry. It presents an overview of the emerging field of petroleomics, which endeavors to understand the fundamental components of crude oil. Petroleomics promises to revolutionize petroleum science in much the same way that genomics transformed the study of medicine not long ago. Asphaltenes are a particular focus, with many chapters devoted to the analysis of their structure and properties.

Table of Contents

1. Petroleomics and Structure–Function Relations of Crude Oils and Asphaltenes
Oliver C. Mullins
1 Introduction
1
2 Evolution of the Oil Patch
5
3 Phenomological Petroleum Analysis
7
4 Petroleomics
10
5 Building Up Petroleum Science A Brief Outline
10
6 Asphaltenes: An Update of the Yen Model
13
7 Future Outlook in Petroleum Science
14
References
16
2. Asphaltene Molecular Size and Weight by Time-Resolved Fluorescence Depolarization
Henning Groenzin and Oliver C. Mullins
1 Introduction
17
1.1 Overview
17
1.2 Chemical Bonding of Functional Groups in Asphaltenes
18
1.3 Techniques Employed to Study the Size of Asphaltenes
18
1.4 Time-Resolved Fluorescence Depolarization (TRFD)
21
1.5 The Optical Range Relevant to Asphaltene Investigations
22
1.6 Structure Predictions from TRFD
26
2 Theory
27
2.1 The Spherical Model
27
2.2 The Anisotropic Rotator
30
3 Experimental Section
33
3.1 Optics Methods
33
3.2 Sample Preparation
35
3.3 Solvent Resonant Quenching of Fluorescence
37
4 Results and Discussion
39
4.1 Basic TRFD of Asphaltenes
39
4.2 Many Virgin Crude Oil Asphaltenes—and Sulfoxide
43
4.3 Asphaltene Solubility Subfractions
43
4.4 Asphaltenes and Resins
45
4.5 Coal Asphaltenes versus Petroleum Asphaltenes
45
4.6 Thermally Processed Feed Stock
50
4.7 Alkyl-Aromatic Melting Points
53
4.8 Asphaltene Molecular Structure 'Like your Hand' or 'Archipelago'
54
4.9 Considerations of the Fluorescence of Asphaltenes
56
4.10 Asphaltene Molecular Diffusion; TRFD vs Other Methods
57
5 Conclusions
59
References
60
3. Petroleomics: Advanced Characterization of Petroleum-Derived Materials by Fourier Transform Ion Cyclotron Resonance Mass Spectrometry (FT-ICR MS)
Ryan P. Rodgers and Alan G. Marshall
1 Introduction
63
2 FT-ICR MS
65
2.1 Mass Accuracy and Mass Resolution
67
2.2 Kendrick Mass and Kendrick Plots
68
2.3 van Krevelen Diagrams
73
2.4 DBE and Z Number
75
2.5 ESI for Access to Polars
75
2.6 EI, FD, and APPI for Access to Nonpolars
76
3 Molecular Weight Determination by Mass Spectrometry
78
3.1 Low Molecular Weight for Petroleum Components
79
3.2 Mass Spectrometry Caveats
82
3.3 High Molecular Weight for Petroleum Components
83
4 Aggregation
84
5 Petroleomics
87
Acknowledgments
88
Glossary
89
References
89
4. Molecular Orbital Calculations and Optical Transitions of PAHs and Asphaltenes
Yosadara Ruiz-Morales
1 Introduction
95
2 Computational Details
100
3 Results and Discussion
102
3.1 Topological Characteristics of PAHs
103
3.2 The HOMO–LUMO Optical Transition
106
3.3 Aromaticity in PAHs and Asphaltenes: Application of the Y-rule
119
3.4 The FAR Region in Asphaltenes
124
3.5 Most Likely PAH Structural Candidates of the FAR Region in Asphaltenes from 5 to 10 Aromatic Rings
127
4 Conclusions
135
Acknowledgments
135
References
135
5. Carbon X-ray Raman Spectroscopy of PAHs and Asphaltenes
Uwe Bergmann and Oliver C. Mullins
1 Introduction
139
2 Theory
142
3 Experiment
143
4 Results and Discussion
145
5 Conclusion and Outlook
152
Acknowledgments
153
References
153
6. Sulfur Chemical Moieties in Carbonaceous Materials
Sudipa Mitra-Kirtley and Oliver C. Mullins
1 Introduction
157
2 Carbonaceous Materials
159
2.1 Production and Deposition of Organic Matter
159
2.2 Diagenesis
160
2.3 Sulfur in Carbonaceous Sediments
161
2.4 Kerogen Formation
162
2.5 Coal and Kerogen Macerals
162
2.6 Catagenesis
164
2.7 Asphaltene Fractions in Crude Oils
165
3 X-Ray Absorption Near Edge Structure (XANES)
165
4 Experimental Section
168
4.1 Synchrotron Beamline
168
4.2 Samples
169
4.3 Least Squares Fitting Procedure
171
5 Results and Discussions
172
5.1 Sulfur XANES on Kerogens
174
5.2 Sulfur XANES on Oil Fractions
175
5.3 Sulfur K-Edge XANES on Coals
176
5.4 Nitrogen XANES
178
6 Conclusion
183
References
184
7. Micellization
Stig E. Friberg
1 Introduction
189
2 Micelles in Aqueous Solutions
190
3 Inverse Micellization in Nonpolar Media
194
4 Asphaltene Association in Crude Oils
199
5 Conclusions
201
Acknowledgments
202
References
202
8. Insights into Molecular and Aggregate Structures of Asphaltenes Using HRTEM
Atul Sharma and Oliver C. Mullins
1 Introduction
205
2 Theory of HRTEM and Image Analysis
208
2.1 Basics of HRTEM
208
2.2 Quantitative Information from TEM Images
212
3 Experimental Section
218
3.1 Samples
218
3.2 HRTEM Method
218
4 Results and Discussion
219
5 Conclusions
227
Acknowledgments
228
References
228
9. Ultrasonic Spectroscopy of Asphaltene Aggregation
Gaelle Andreatta, Neil Bostrom, and Oliver C. Mullins
1 Introduction
231
2 Ultrasonic Spectroscopy
233
2.1 Ultrasonic Resonances
234
2.2 Plane Wave Propagation
235
2.3 Experimental Section
236
2.4 Compressibility of Liquids and Ultrasonic Velocity
238
3 Micellar Aggregation Model
238
3.1 Theory
238
3.2 Experimental Results on Surfactants
241
4 Experimental Results on Asphaltenes
247
4.1 Background
247
4.2 Ultrasonic Determination of Various Asphaltenes Aggregation Properties
248
4.3 Comparison of Experimental Results on UG8 Asphaltenes and Maltenes
253
4.4 Differences Between Coal and Petroleum Asphaltenes
254
5 Conclusion
255
References
255
10. Asphaltene Self-Association and Precipitation in Solvents—AC Conductivity Measurements
Eric Sheu, Yicheng Long, and Hassan Hamza
1 Introduction
259
2 Experimental
264
2.1 Sample
264
2.2 Instrument
264
2.3 Measurement
265
3 Theory
266
4 Results
269
5 Discussion and Conclusion
274
6 Future Perspective
276
References
276
11. Molecular Composition and Dynamics of Oils from Diffusion Measurements
Denise E. Freed, Natalia V. Lisitza, Pabitra N. Sen, and Yi-Qiao Song
1 Introduction
279
2 General Theory of Molecular Diffusion
280
3 Experimental Method
282
4 Mixtures of Alkanes
283
4.1 Chain-Length Dependence
284
4.2 Dependence on Mean Chain Length and Free Volume Model
285
4.3 Comparison with Experiments
287
4.4 Viscosity
289
4.5 Discussion
291
5 Dynamics Of Asphaltenes In Solution
292
5.1 The Proton Spectrum of Asphaltene Solutions
292
5.2 The Diffusion Constant and Diffusion Spectrum
293
5.3 Discussion
294
6 Conclusions
296
Acknowledgment
296
References
296
12. Application of the PC-SAFT Equation of State to Asphaltene Phase Behavior
P. David Ting, Doris L. Gonzalez, George J. Hirasaki, and Walter G. Chapman
1 Introduction
301
1.1 Asphaltene Properties and Field Observations
302
1.2 The Two Views of Asphaltene Interactions
303
1.3 Our View and Approach
305
2 Introduction to SAFT
306
2.1 PC-SAFT Pure Component Parameters
307
2.2 PC-SAFT Characterization of a Recombined Oil
307
2.3 Comparison of Results and Analysis of Asphaltene Behavior
313
2.4 Effect of Asphaltene Polydispersity on Phase Behavior
317
3 Summary and Conclusions
323
Acknowledgments
324
References
325
13. Application of Isothermal Titration Calorimetry in the Investigation of Asphaltene Association
Daniel Merino-Garcia and Simon Ivar Andersen
1 Introduction
329
2 The Concept of Micellization
330
3 Experimental
331
3.1 Asphaltene Separation
331
4 Application of ITC to Surfactants
332
4.1 Nonaqueous Systems
334
5 ITC Experiments with Asphaltene Solutions: Is There a CMC?
335
6 Modeling ITC Experiments
338
7 Application of ITC to Various Aspects of Asphaltene Association and Interaction with Other Substances
340
7.1 Investigation of Asphaltene Subfractions
341
7.2 Effect of Methylation of Asphaltenes
343
7.3 Interaction of Asphaltene with Other Compounds
345
8 Conclusions
350
Acknowledgments
350
References
351
14. Petroleomics and Characterization of Asphaltene Aggregates Using Small Angle Scattering
Eric Y. Sheu
1 Introduction
353
2 Asphaltene Aggregation
355
3 SAXS and SANS
356
4 SAXS and SANS Instruments
362
5 SAXS and SANS Experiments and Results
364
5.1 SAXS Measurement on Ratawi Resin and Asphaltene
365
5.2 SANS Measurement on Asphaltene Aggregation, Emulsion, and Dispersant Effect
367
6 Discussion
371
7 Conclusion
372
8 Future Perspectives
373
Acknowledgments
373
References
373
15. Self-Assembly of Asphaltene Aggregates: Synchrotron, Simulation and Chemical Modeling Techniques Applied to Problems in the Structure and Reactivity of Asphaltenes
Russell R. Chianelli, Mohammed Siadati, Apurva Mehta, John Pople, Lante Carbognani Ortega, and Long Y. Chiang
1 Introduction
375
2 WAXS Synchrotron Studies and Sample Preparation
377
3 SAXS
380
3.1 Fractal Objects
381
3.2 Scattering from Mass Fractal Objects
383
3.3 Scattering from a Surface Fractal Object
383
4 SAXS Studies of Venezuelan and Mexican Asphaltenes
383
5 Self-Assembly of Synthetic Asphaltene Particles
393
6 Conclusions
399
Acknowledgments
399
References
400
16. Solubility of the Least-Soluble Asphaltenes
Jill S. Buckley, Jianxin Wang, and Jefferson L. Creek
1 Introduction
401
1.1 Importance of the Least-Soluble Asphaltenes
402
1.2 Detection of the Onset of Asphaltene Instability
403
1.3 Asphaltenes as Colloidal Dispersions
403
1.4 Asphaltenes as Lyophilic Colloids
405
1.5 Solubility of Large Molecules
405
1.6 Solubility Parameters
406
1.7 Flory–Huggins Predictions: The Asphaltene Solubility Model (ASM)
412
2 Asphaltene Instability Trends (ASIST)
414
2.1 ASIST Established by Titrations with n-Alkanes
414
2.2 Use of ASIST to Predict Onset Pressure
417
3 Asphaltene Stability in Oil Mixtures
420
4 Some Remaining Problems
424
4.1 Effect of Temperature on ASIST
425
4.2 Polydispersity and Amount of Asphaltene
425
4.3 Wetting, Deposition, and Coprecipitation
426
4.4 Model Systems and Standards
426
5 Conclusions
427
Acknowledgment
427
References
428
Appendix I: Asphaltene Onset Detection by Batch Titration
429
Appendix II: Historical Interpretations of n-Alkane Titration Data
432
Appendix III: Calculation of Solubility Parameters Using PVTsim
432
Appendix IV: Oil and Asphaltene Properties
434
Appendix V: Prediction of Live Oil Asphaltene Stability from ASIST
436
17. Dynamic Light Scattering Monitoring of Asphaltene Aggregation in Crude Oils and Hydrocarbon Solutions
Igor K. Yudin and Mikhail A. Anisimov
1 Introduction
439
2 Dynamic Light Scattering Technique
441
3 Aggregation of Asphaltenes in Toluene–Heptane Mixtures
448
4 Aggregation of Asphaltenes in Crude Oils
454
5 Stabilization of Asphaltene Colloids
460
6 Viscosity and Microrheology of Petroleum Systems
462
7 Conclusions
465
Acknowledgments
466
References
466
18. Near Infrared Spectroscopy to Study Asphaltene Aggregation in Solvents
Kyeongseok Oh and Milind D. Deo
1 Introduction
469
2 Literature
470
3 Experimental
472
4 Results and Discussion
473
4.1 Asphaltene Aggregation or Self-Association
473
4.2 Onset of Asphaltene Precipitation
475
4.3 Effect of the Solvent
479
4.4 Asphaltene Subfractions
485
5 Conclusions
486
Acknowledgments
487
References
487
19. Phase Behavior of Heavy Oils
John M. Shaw and Xiangyang Zou
1 Introduction
489
2 Origin of Multiphase Behavior in Hydrocarbon Mixtures
490
3 Phase Behavior Prediction
493
3.1 Bulk Phase Behavior Prediction for Hydrocarbon Mixtures
493
3.2 Asphaltene Precipitation and Deposition Models
494
4 Experimental Methods and Limitations
495
5 Phase Behavior Observations and Issues
497
5.1 Heavy Oil
497
5.2 Heavy Oil + Solvent Mixtures
500
5.3 Phase Behavior Reversibility
504
6 Conclusions
506
Acknowledgments
507
References
507
20. Selective Solvent Deasphalting for Heavy Oil Emulsion Treatment
Yicheng Long, Tadeusz Dabros, and Hassan Hamza
1 Introduction
511
2 Bitumen Chemistry
512
3 Stability of Water-in-Bitumen Emulsions
515
3.1 In situ Bitumen Emulsion and Bitumen Froth
515
3.2 Size Distributions of Emulsified Water Droplets and Dispersed Solids
516
3.3 Stabilization Mechanism of Bitumen Emulsions
518
4 Effect of Solvent on Bitumen Emulsion Stability
519
5 Treatment of Bitumen Emulsions with Aliphatic Solvents
522
5.1 Behavior of Bitumen Emulsion upon Dilution
522
5.2 Settling Characteristics of Bitumen Emulsions Diluted with Aliphatic Solvent
524
5.3 Settling Curve and Settling Rate of WD/DS/PA Aggregates
526
5.4 Structural Parameters of WD/DS/PA Aggregates
531
5.5 Measuring Settling Rate of WD/DS/PA Aggregates Using In-Line Fiber-Optic Probe
534
5.6 Asphaltene Rejection
537
5.7 Product Quality—Water and Solids Contents
538
5.8 Product Quality—Micro-Carbon Residue (MCR)
540
5.9 Product Quality—Metals Contents
542
5.10 Product Quality—Sulfur and Nitrogen Contents
542
5.11 Viscosity of Bitumen
543
6 Conclusion
543
Acknowledgments
545
References
545
21. The Role of Asphaltenes in Stabilizing Water-in-Crude Oil Emulsions
Johan Sjöblom, Pál V. Hemmingsen, and Harald Kallevik
1 Introduction
549
2 Chemistry of Crude Oils and Asphaltenes
551
2.1 Analytical Separation of Crude Oil Components
551
2.2 Solubility and Aggregation of Asphaltenes
554
2.3 Characterization of Crude Oils by Near Infrared Spectroscopy
555
2.4 Asphaltene Aggregation Studied by High-Pressure NIR Spectroscopy
556
2.5 Disintegration of Asphaltenes Studied by NIR Spectroscopy
559
2.6 Asphaltene Aggregation Studied by NMR
563
2.7 Adsorption of Asphaltenes and Resins Studied by Dissipative Quartz Crystal Microbalance (QCM-D™)
563
2.8 Interfacial Behavior and Elasticity of Asphaltenes
566
3 Chemistry of Naphthenic Acids
569
3.1 Origin and Structure
570
3.2 Phase Equilibria
570
4 Water-in-Crude Oil Emulsions
572
4.1 Stability Mechanisms
572
4.2 Characterization by Critical Electric Fields
573
4.3 Multivariate Analysis and Emulsion Stability
574
4.4 High-Pressure Performance of W/O Emulsions
578
Acknowledgments
584
References
584
22. Live Oil Sample Acquisition and Downhole Fluid Analysis
Go Fujisawa and Oliver C. Mullins
1 Introduction
589
2 Wireline Fluid Sampling Tools
591
3 Downhole Fluid Analysis with Wireline Tools
593
3.1 Measurement Physics
593
3.2 DFA Implementation in Wireline Tools
601
4 Live Oil Sampling Process
604
4.1 Contamination
604
4.2 Phase Transition
606
4.3 Chain of Custody
607
5 "What Is the Nature of the Hydrocarbon Fluid?"
608
6 "What Is the Size and Structure of the Hydrocarbon-Bearing Zone?"
610
7 Conclusions
614
References
615
23. Precipitation and Deposition of Asphaltenes in Production Systems: A Flow Assurance Overview
Ahmed Hammami and John Ratulowski
1 Introduction
617
2 Chemistry of Petroleum Fluids
619
2.1 Saturates
621
2.2 Aromatics
621
2.3 Resins
621
2.4 Asphaltenes
622
3 Petroleum Precipitates and Deposits
622
3.1 Petroleum Waxes
622
3.2 Asphaltene Deposits
623
3.3 Diamondoids
623
3.4 Gas Hydrates
623
4 Terminology: Precipitation vs. Deposition
624
5 Mechanisms of Asphaltene Precipitation: What We Think We Know and Why?
625
5.1 Colloidal Model
626
5.2 Effect of Compositional Change
626
5.3 Effect of Pressure Change
628
5.4 The de Boer Plot
630
5.5 Reversibility of Asphaltene Precipitation
631
6 Sampling
631
7 Laboratory Sample Handling and Analyses
634
7.1 Sample Handling and Transfer
634
7.2 Compositional Analyses
635
7.3 Oil-Based Mud (OBM) Contamination Quantification
635
7.4 Dead Oil Characterization
637
7.5 Dead Oil Asphaltene Stability Tests
640
8 Live Oil Asphaltene Stability Techniques
643
8.1 Light Transmittance (Optical) Techniques
643
8.2 High Pressure Microscope (HPM)
647
8.3 Deposition Measurements
651
9 Asphaltene Precipitation Models
652
Acknowledgment
656
References
656
Index 661

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