Development of new oil/water partitioning tracers for the determination of residual oil saturation in the inter-well region of water-flooded reservoirs

Authors

Mario Helder Lopes da Silva
Keywords: petroleumsgeologi, IOR

Synopsis

Most of the hydrocarbon-rich large unexplored basins are located in remote and/or highly environmentally sensitive regions. As more and more oilfields reach maturity at the end of the secondary stage of recovery, while on average more than 50% of the original reserves of hydrocarbons are left in place, the future of oil production on the Norwegian Continental shelf (NCS) will increasingly rely on IOR projects to face the demand. A partitioning inter-well tracer test (PITT) is a type of tracer test that measures the water contactable saturation of immobile oil (SOR) in the inter-well region of water flooded reservoirs. Knowledge about SOR in the swept volumes between injector/producer pairs is a key parameter for the design and evaluation of IOR projects. The PITT explores the lag in production experienced by an oil/water partitioning tracer relatively to a passive water tracer which directly correlates to SOR. This principle was introduced to the industry in 1971 and relied on the use of molecules successfully applied in hydrology and/or labelled with radioactive nuclides for easier detection. The conditions encountered in oil reservoirs, particularly in deep oil formations, are significantly harsher than in the near surface subsoil. Thus, several unsuccessful inter-well tracer tests resulted from a poor selection of the tracer compounds used at that time because of insufficient knowledge about their behaviour under typical reservoir conditions. Much work has been done to improve the original concept of the PITT regard its deployment and interpretation. However, little effort has been put in place to establish a systematic procedure for selecting, testing and describing the dynamic behaviour of the substances used as oil/water partitioning tracers. Thus, this thesis aims to present a methodology for selection and testing of new PITT tracer candidates, with the results and findings of its application to a selected group of molecules.

 The methodology presented here starts by describing the base requirements for selection of new oil/water partitioning tracer candidates. Additionally, guidelines for testing and qualification are presented. There are several steps in the qualification procedure. These can be divided into static stability experiments, development of analytical methods for laboratory samples, development of analytical methods for identification and quantification of the stable molecules in real produced waters, characterisation of the oil/water partition coefficient (K) of the molecules, and dynamic flooding experiments using cores of consolidated sedimentary rock. Following this method, step by step, 16 molecules from 4 different chemical “families” were selected and tested for qualification as new oil/water partitioning tracers. The static stability experiments evaluated the thermal stability of the PITT tracer candidates, in the absence and presence of typical reservoir rock materials, different pH conditions, and elevated salinity up to 150 0C for 12 weeks contact time. Ultra-performance liquid chromatography (UPLC) coupled with ultra-violet detection (UV) and high-resolution mass spectrometry (HRMS), and gas chromatography (GC) coupled with flame ionisation detection (FID) were the techniques used to follow the concentration of the PITT tracer candidates along the 12 weeks of experiment. UPLC-HRMS was used to try to obtain relevant information to describe the observed phenomena. The static stability experiments proved that only 5 of the 16 tested compounds were stable for 12 weeks up to 150 ℃. Two additional compounds were stable for the same period up to 125 ℃. This is sufficient to allow for their use in most oilfields, and they were thus included as possible inter-well PITT tracers. These experiments also revealed dramatic interactions between some of the studied molecules and clay minerals of undefined nature, as well as thermally driven degradation of the candidates that is well described by a pseudo-first order kinetic model. The latter two findings open the possibility of using tracers to retrieve information about temperature and geochemistry/mineralogy in the inter-well region, though the latter requires further development.

 A method based on sequential direct immersion (DI) headspace (HS) solid-phase microextraction (SPME) proved effective as analytical sample pre-treatment followed by GC-MS/MS for analysis of the PITT tracer candidate concentrations in real production waters. The DI-HS-SPME-GC-MS/MS method allows for quantification of the stable molecules investigated in low ng/L concentrations and introduces significant improvements in comparison to the commonly used methodologies for analysis of tracers in produced waters: it requires just 5 mL of sample and eliminates the need for use of organic solvents in the laboratory. Furthermore, sample processing times are significantly reduced as the cleaning/concentration step becomes much faster. This is of utmost importance for a PITT, as several hundreds of samples are analysed in these examinations.

 The characterisation of the K-values of the stable PITT tracer candidates revealed that they will likely vary along the volume swept between injector/producer pairs. K is influenced primarily by the ionic strength of the aqueous phase and composition of the hydrocarbon phase, and to a smaller extent by temperature T. The influence of temperature can, however, be very relevant: The K-value is used in the calculation of SOR together with the times of arrival of the different tracers using the same landmark of their respective production curves (i.e., the theoretically most correct is the first moments of the curves). It is likely that the temperature varies between injector and producer well-pairs. The variation of the K-value as function of T needs to be accounted for to determine accurate SOR values. Variations of the ionic strength will lead to even bigger variations of the K-value independently of the valency of the ions present in the aqueous phase. The experiments performed also confirmed the constant and reversible equilibrium distribution of the oil/water tracer candidates between hydrocarbon and aqueous phases, as well as their suitability for use on most oilfields of the NCS.

 The flooding experiments were performed on sandstone and chalk cores prepared both to pure water saturation and to residual oil saturation, SOR. Residence time distribution analysis (RTD) was used to interpret the production curves. These experiments proved that the PITT tracer candidates behave as water tracers in the absence of hydrocarbons, with no significant difference encountered between their production curves and the ones obtained from the reference water tracer (tritiated water). SOR was determined for two different mass recovery landmarks in each of the experiments for all partitioning tracers using the K-values previously determined in the experiments for characterisation of the K-values. Good agreement between all SOR values measured by the tracer candidates and the values determined by a balance to the oil used to prepare the cores was encountered. This is also valid when SOR measured by the tracers is compared to the value obtained by the differences in water flooded pore volumes measured by tritiated water.

 The methodology presented and applied in this thesis produced 7 new oil/water partitioning tracers ready to be used in oil fields with low probability of failure. The findings and observations presented here can be incorporated into reservoir models to obtain more accurate data from PITTs, and consequently better reservoir description. Furthermore, the reinjection of produced waters will lead to contaminations of the inter-well region with tracers used there. Thus, the present study offers guidelines and methods for the development of new tracers. The oil industry, service companies, and other researchers working with tracer technology will be the primary beneficiaries of this study, that will hopefully contribute to disseminate the use of PITTs by the industry. This technology has a large potential to contribute to a future efficient and profitable oil production.

Author Biography

Mario Helder Lopes da Silva

The National IOR Centre of Norway,
University of Stavanger
mario.silva@ife.no

References

Adams, T.B., Doull, J., Feron, V.J., Goodman, J.I., Marnett, L.J., Munro, I.C., Newberne, P.M., Portoghese, P.S., Smith, R.L., Waddell, W.J., Wagner, B.M., 2002. The FEMA GRAS assessment of pyrazine derivatives used as flavor ingredients. Food and Chemical Toxicology 40, 429-451.

https://doi.org/10.1016/S0278-6915(01)00123-5

Ahmad, M., Tasneem, M.A., Rafiq, M., Khan, I.H., Farooq, M., Sajjad, M.I., 2003. Interwell tracing by environmental isotopes at Fimkassar Oilfield, Pakistan. Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 58, 611-619.

https://doi.org/10.1016/S0969-8043(03)00059-9

Ahsan, H.M., Breedlove, B.K., Piangrawee, S., Mian, M.R., Fetoh, A., Cosquer, G., Yamashita, M., 2018. Enhancement of electrocatalytic abilities for reducing carbon dioxide: functionalization with a redoxactive ligand-coordinated metal complex. Dalton Transactions 47, 11313-11316.

https://doi.org/10.1039/C8DT02288G

AlAbbad, M.A., Sanni, M.L., Kokal, S., Krivokapic, A., Dye, C., Dugstad, Ø., Hartvig, S.K., Huseby, O.K., 2018. A Step Change for Single-Well Chemical-Tracer Tests: Field Pilot Testing of New Sets of Novel Tracers. SPE-181408-PA Preprint, 13.

https://doi.org/10.2118/181408-PA

Alasalvar, C., Shahidi, F., Cadwallader, K.R., 2003. Comparison of natural and roasted Turkish tombul hazelnut (Corylus avellana L.) volatiles and flavor by DHA/GC/MS and descriptive sensory analysis. J. Agric. Food Chem. 51, 5067-5072.

https://doi.org/10.1021/jf0300846

Asadi, M., Shook, G.M., 2010. Application of Chemical Tracers in IOR: A Case History, North Africa Technical Conference and Exhibition. Society of Petroleum Engineers, Cairo, Egypt, p. 11.

https://doi.org/10.2118/126029-MS

Austine, J., van Batenburg, D.W., Southwick, J.G., Zarubinska, M.A., Paramanathan, S., Bouwmeester, R.C.M., Kechut, N.I., Viig, S.O., Haugen, O.B., Brandvoll, Ø., 2015. Laboratory Evaluation of Inter-Well Partitioning Tracers for the Determination of Remaining Oil Saturation after ASP Flooding, SPE Asia Pacific Enhanced Oil Recovery Conference. Society of Petroleum Engineers, Kuala Lumpur, Malaysia, p. 14.

https://doi.org/10.2118/174610-MS

Babu Valapa, R., Loganathan, S., Pugazhenthi, G., Thomas, S., Varghese, T.O., 2017. Chapter 2 - An Overview of Polymer-Clay Nanocomposites, in: Jlassi, K., Chehimi, M.M., Thomas, S. (Eds.), ClayPolymer Nanocomposites. Elsevier, pp. 29-81.

https://doi.org/10.1016/B978-0-323-46153-5.00002-1

Bae, E., Na, J.-G., Chung, S.H., Kim, H.S., Kim, S., 2010. Identification of about 30 000 Chemical Components in Shale Oils by Electrospray Ionization (ESI) and Atmospheric Pressure Photoionization (APPI) Coupled with 15 T Fourier Transform Ion Cyclotron Resonance Mass Spectrometry (FT-ICR MS) and a Comparison to Conventional Oil. Energy & Fuels 24, 2563-2569.

https://doi.org/10.1021/ef100060b

Bakaikina, N.V., Kenessov, B., Ul'yanovskii, N.V., Kosyakov, D.S., 2018. Quantification of transformation products of rocket fuel unsymmetrical dimethylhydrazine in soils using SPME and GC-MS. Talanta 184, 332-337.

https://doi.org/10.1016/j.talanta.2018.02.047

Belver, C., Bañares Muñoz, M.A., Vicente, M.A., 2002. Chemical Activation of a Kaolinite under Acid and Alkaline Conditions. Chemistry of Materials 14, 2033-2043.

https://doi.org/10.1021/cm0111736

Bhattacharyya, K.G., Gupta, S.S., 2008. Adsorption of a few heavy metals on natural and modified kaolinite and montmorillonite: A review. Advances in Colloid and Interface Science 140, 114-131.

https://doi.org/10.1016/j.cis.2007.12.008

Bjørnstad, T., 1991. Selection of tracers for oil and gas evaluation, Norway, p. 48.

Bjørnstad, T., Haugen, O.B., Hundere, I.A., 1994. Dynamic behavior of radio-labelled water tracer candidates for chalk reservoirs. Journal of Petroleum Science and Engineering 10, 223-238.

https://doi.org/10.1016/0920-4105(94)90083-3

Blank, I., Sen, A., Grosch, W., 1992. Potent odorants of the roasted powder and brew of Arabica coffee Z. Lebensm.-Unters.-Forsch. 195, 239-245.

https://doi.org/10.1007/BF01202802

Boyaci, E., Gorynski, K., Viteri, C.R., Pawliszyn, J., 2016. A study of thin film solid phase microextraction methods for analysis of fluorinated benzoic acids in seawater. Journal of Chromatography A 1436, 51-58.

https://doi.org/10.1016/j.chroma.2016.01.071

Buttery, R.G., Stern, D.J., Ling, L.C., 1994. Studies on flavor volatiles of some sweet corn products. J. Agric. Food Chem. 42, 791-795.

https://doi.org/10.1021/jf00039a038

Câmara, J.S., Alves, M.A., Marques, J.C., 2006. Multivariate analysis for the classification and differentiation of Madeira wines according to main grape varieties. Talanta 68, 1512-1521.

https://doi.org/10.1016/j.talanta.2005.08.012

Causin, E., Rochon, J., Marzorati, D., 1990. Field Measurements of Remaining Oil Saturation, SPE/DOE Enhanced Oil Recovery Symposium. Society of Petroleum Engineers, Tulsa, Oklahoma, p. 9.

https://doi.org/10.2118/20260-MS

Cerny, C., Grosch, W., 1994. Precursors of ethyldimethylpyrazine isomers and 2,3-diethyl-5-methylpyrazine formed in roasted beef Z. Lebensm.-Unters.-Forsch. 198, 210-214.

https://doi.org/10.1007/BF01192597

Cooke, C.E.J., 1971. "Method of determining fluid saturations in reservoirs" (US Patent 3,590,923). Esso Production Research Company, USA.

de Hoffmann, E., Stroobant, V., 2007. Mass Spectrometry: Principles and Applications, 3rd Edition. John Wiley & Sons, New York.

Deans, H.A., 1971. "Method of determining fluid saturations in reservoirs" (US Patent 3,623,842). Esso Production Research Company, USA.

Deans, H.A., 1978. Using Chemical Tracers To Measure Fractional Flow And Saturation In-Situ, SPE Symposium on Improved Methods of Oil Recovery. Society of Petroleum Engineers, Tulsa, Oklahoma, p. 10. Dearden, J.C., Bresnen, G.M., 1988. The Measurement of Partition Coefficients. Quantitative Structure-Activity Relationships 7, 133-144.

Dugstad, O., Viig, S., Krognes, B., Kleven, R., Huseby, O., 2013. Tracer monitoring of enhanced oil recovery projects, in: Haugan, A. (Ed.), Tracer 6 - the 6th International Conference on Tracers and Tracing Methods. E D P Sciences, Cedex A.

https://doi.org/10.1051/epjconf/20135002002

Esteruelas, M.A., Garcı́a-Obregón, T., Herrero, J., Oliván, M., 2011. Osmium-Catalyzed Oxidation of Primary Alcohols with Molecular Oxygen. Organometallics 30, 6402-6407.

https://doi.org/10.1021/om200684m

Eurachem, 2014. The Fitness for Purpose of Analytical Methods: A Laboratory Guide to Method Validation and Related Topics: Second edition. www.eurachem.org.

Fakhru'l-Razi, A., Pendashteh, A., Abdullah, L.C., Biak, D.R.A., Madaeni, S.S., Abidin, Z.Z., 2009. Review of technologies for oil and gas produced water treatment. Journal of Hazardous Materials 170, 530- 551.

https://doi.org/10.1016/j.jhazmat.2009.05.044

Frank, D.C., Owen, C.M., Patterson, J., 2004. Solid phase microextraction (SPME) combined with gas-chromatography and olfactometry-mass spectrometry for characterization of cheese aroma compounds. LWT - Food Science and Technology 37, 139-154.

https://doi.org/10.1016/S0023-6438(03)00144-0

Gutiérrez, M.C., Carriazo, D., Ania, C.O., Parra, J.B., Ferrer, M.L., del Monte, F., 2011. Deep eutectic solvents as both precursors and structure directing agents in the synthesis of nitrogen doped hierarchical carbons highly suitable for CO2 capture. Energy & Environmental Science 4, 3535-3544.

https://doi.org/10.1039/c1ee01463c

Hartvig, S.K., Huseby, O., Yasin, V., Ogezi, O., Ernst, B., Reimann, S., Leonhardt, B., 2015. Use of a New Class of Partitioning Tracers to Assess EOR and IOR Potential in the Bockstedt Field.

https://doi.org/10.3997/2214-4609.201412118

Hedegaard, K., Graue, A., 2011. Does Wettability Affect the Strength of Chalk?, 45th U.S. Rock Mechanics / Geomechanics Symposium. American Rock Mechanics Association, San Francisco, California, p. 6.

Higashimoto, S., Kitao, N., Yoshida, N., Sakura, T., Azuma, M., Ohue, H., Sakata, Y., 2009. Selective photocatalytic oxidation of benzyl alcohol and its derivatives into corresponding aldehydes by molecular oxygen on titanium dioxide under visible light irradiation. Journal of Catalysis 266, 279-285.

https://doi.org/10.1016/j.jcat.2009.06.018

Hirsh, A.J., Zhang, J., Zamurs, A., Fleegle, J., Thelin, W.R., Caldwell, R.A., Sabater, J.R., Abraham, W.M., Donowitz, M., Cha, B., Johnson, K.B., St. George, J.A., Johnson, M.R., Boucher, R.C., 2008. Pharmacological Properties of N-(3,5-Diamino-6- chloropyrazine-2-carbonyl)-N′-4-[4-(2,3- dihydroxypropoxy)phenyl]butyl-guanidine Methanesulfonate (552-02), a Novel Epithelial Sodium Channel Blocker with Potential Clinical Efficacy for Cystic Fibrosis Lung Disease. Journal of Pharmacology and Experimental Therapeutics 325, 77-88.

https://doi.org/10.1124/jpet.107.130443

Hjuler, M.L., Fabricius, I.L., 2009. Engineering properties of chalk related to diagenetic variations of Upper Cretaceous onshore and offshore chalk in the North Sea area. Journal of Petroleum Science and Engineering 68, 151-170.

https://doi.org/10.1016/j.petrol.2009.06.005

Janado, M., Yano, Y., Doi, Y., Sakamoto, H., 1983. Peculiar effects of alkali thiocyanates on the activity coefficients of aromatic hydrocarbons in water. Journal of Solution Chemistry 12, 741-754.

https://doi.org/10.1007/BF00647385

Jiang, S., 2012. Clay Minerals from the Perspective of Oil and Gas Exploration, in: Valaškova, M., Martynkova, G.S. (Eds.), Clay Minerals in Nature - Their Characterization, Modification and Application. InTech, Rijeka, p. Ch. 2.

https://doi.org/10.5772/47790

Jousse, F., Jongen, T., Agterof, W., Russell, S., Braat, P., 2002. Simplified Kinetic Scheme of Flavor Formation by the Maillard Reaction. Journal of Food Science 67, 2534-2542.

https://doi.org/10.1111/j.1365-2621.2002.tb08772.x

Kaviani, S., Izadyar, M., 2018. The possibility of iron chelation therapy in the presence of different HPOs; a molecular approach to the noncovalent interactions and binding energies. Journal of Molecular Structure 1166, 448-455.

https://doi.org/10.1016/j.molstruc.2018.04.065

King, P.J., Morton, F., Sagarra, A., 1973. Chemistry and physics of petroleum, in: Hobson, G.D., Pohl, W. (Eds.), Modern petroleum technology, 4th ed. Applied Science Publishers, Barking, U.K.

Leo, A., Hansch, C., Elkins, D., 1971. Partition coefficients and their uses. Chemical Reviews 71, 525-616.

https://doi.org/10.1021/cr60274a001

Li, C., Huang, Y., Dong, X., Sun, Z., Duan, X., Ren, B., Zheng, S., Dionysiou, D.D., 2019. Highly efficient activation of peroxymonosulfate by natural negatively-charged kaolinite with abundant hydroxyl groups for the degradation of atrazine. Applied Catalysis B: Environmental 247, 10-23.

https://doi.org/10.1016/j.apcatb.2019.01.079

Lichtenberger, G.J., 1991. Field Applications of Interwell Tracers for Reservoir Characterization of Enhanced Oil Recovery Pilot Areas, SPE Production Operations Symposium. Society of Petroleum Engineers, Oklahoma City, Oklahoma.

https://doi.org/10.2118/21652-MS

Liu, S.-m., Wu, C.-H., Huang, H.-J., 1998. Toxicity and anaerobic biodegradability of pyridine and its derivatives under sulfidogenic conditions. Chemosphere 36, 2345-2357.

https://doi.org/10.1016/S0045-6535(97)10203-X

Lucas, L.L., Unterweger, M.P., 2000. Comprehensive Review and Critical Evaluation of the Half-Life of Tritium. Journal of Research of the National Institute of Standards and Technology 105, 541-549.

https://doi.org/10.6028/jres.105.043

Lucia, F.J., 1995. ROCK-FABRIC PETROPHYSICAL CLASSIFICATION OF CARBONATE PORE-SPACE FOR RESERVOIR CHARACTERIZATION. AAPG Bull.-Am. Assoc. Petr. Geol. 79, 1275-1300.

https://doi.org/10.1306/7834D4A4-1721-11D7-8645000102C1865D

Luo, L., Kim, S.-W., Lee, H.-K., Kim, I.-D., Lee, H., Lee, J.-K., 2017. Anti-oxidative effects of 4-hydroxybenzyl alcohol in astrocytes confer protective effects in autocrine and paracrine manners. PLOS ONE 12, e0177322.

https://doi.org/10.1371/journal.pone.0177322

Madland, M.V., Hiorth, A., Omdal, E., Megawati, M., HildebrandHabel, T., Korsnes, R.I., Evje, S., Cathles, L.M., 2011. Chemical Alterations Induced by Rock-Fluid Interactions When Injecting Brines in High Porosity Chalks. Transport in Porous Media 87, 679-702.

https://doi.org/10.1007/s11242-010-9708-3

Makoś, P., Fernandes, A., Przyjazny, A., Boczkaj, G., 2018. Sample preparation procedure using extraction and derivatization of carboxylic acids from aqueous samples by means of deep eutectic solvents for gas chromatographic-mass spectrometric analysis. Journal of Chromatography A 1555, 10-19.

https://doi.org/10.1016/j.chroma.2018.04.054

Mannam, M.R., Devineni, S.R., Pavuluri, C.M., Chamarthi, N.R., Kottapalli, R.S.P., 2019. Urea and thiourea derivatives of 3- (trifluoromethyl)-5,6,7,8-tetrahydro-[1, 2, 4]triazolo[4,3-a]pyrazine: Synthesis, characterization, antimicrobial activity and docking studies. Phosphorus, Sulfur, and Silicon and the Related Elements 194, 922-932.

https://doi.org/10.1080/10426507.2019.1577845

Mantri, K., Komura, K., Kubota, Y., Sugi, Y., 2005. Friedel-Crafts alkylation of aromatics with benzyl alcohols catalyzed by rare earth metal triflates supported on MCM-41 mesoporous silica. Journal of Molecular Catalysis A: Chemical 236, 168-175

https://doi.org/10.1016/j.molcata.2005.04.020

Mautner, F.A., Traber, M., Fischer, R.C., Reichmann, K., Vicente, R., 2018. Synthesis and characterization of pseudohalide-metal(II) complexes with 4-methoxypyridine as co-ligand. Polyhedron 144, 30- 35.

https://doi.org/10.1016/j.poly.2018.01.012

Meinardus, H.W., Dwarakanath, V., Ewing, J., Hirasaki, G.J., Jackson, R.E., Jin, M., Ginn, J.S., Londergan, J.T., Miller, C.A., Pope, G.A., 2002. Performance assessment of NAPL remediation in heterogeneous alluvium. Journal of Contaminant Hydrology 54, 173-193.

https://doi.org/10.1016/S0169-7722(01)00161-9

Menéndez, B., Zhu, W., Wong, T.-F., 1996. Micromechanics of brittle faulting and cataclastic flow in Berea sandstone. Journal of Structural Geology 18, 1-16.

https://doi.org/10.1016/0191-8141(95)00076-P

Morad, M., Nowicka, E., Douthwaite, M., Iqbal, S., Miedziak, P., Edwards, J.K., Brett, G.L., He, Q., Morgan, D., Alshammari, H., Bethell, D., Knight, D.W., Sankar, M., Hutchings, G.J., 2017. Multifunctional supported bimetallic catalysts for a cascade reaction with hydrogen auto transfer: synthesis of 4-phenylbutan-2-ones from 4-methoxybenzyl alcohols. Catal. Sci. Technol. 7, 1928-1936.

https://doi.org/10.1039/C7CY00184C

Morse, J.W., Arvidson, R.S., 2002. The dissolution kinetics of major sedimentary carbonate minerals. Earth-Sci. Rev. 58, 51-84.

https://doi.org/10.1016/S0012-8252(01)00083-6

Muller, K., Seubert, A., 2012. Ultra trace determination of fluorobenzoic acids in tap and reservoir water using solid-phase extraction and gas chromatography-mass spectrometry. Journal of chromatography. A 1260, 9-15.

https://doi.org/10.1016/j.chroma.2012.08.050

Muller, K., Seubert, A., 2014. Ultra trace determination of fluorobenzoic acids in reservoir and ground water using isotope dilution gas chromatography mass spectrometry. Isotopes in environmental and health studies 50, 277-284.

https://doi.org/10.1080/10256016.2014.891995

Müller, R., Rappert, S., 2010. Pyrazines: occurrence, formation and biodegradation. Applied Microbiology and Biotechnology 85, 1315- 1320.

https://doi.org/10.1007/s00253-009-2362-4

Nasr, K., Meimoun, J., Favrelle-Huret, A., Winter, J.D., Raquez, J.M., Zinck, P., 2020. Enzymatic Polycondensation of 1,6-Hexanediol and Diethyl Adipate: A Statistical Approach Predicting the Key-Parameters in Solution and in Bulk. Polymers 12, 15.

https://doi.org/10.3390/polym12091907

NPD, 2020. "Facts about oil production". https://www.npd.no/en/facts/production/, accessed on 23.09.2020.

Prado, G.H.C., Rao, Y., de Klerk, A., 2017. Nitrogen Removal from Oil: A Review. Energy & Fuels 31, 14-36.

https://doi.org/10.1021/acs.energyfuels.6b02779

Salager, J.-L., Marquez, N., Graciaa, A., Lachaise, J., 2000. Partitioning of Ethoxylated Octylphenol Surfactants in Microemulsion−Oil−Water Systems: Influence of Temperature and Relation between Partitioning Coefficient and Physicochemical Formulation. Langmuir 16, 5534-5539.

https://doi.org/10.1021/la9905517

Sangster, J., 1989. Octanol‐Water Partition Coefficients of Simple Organic Compounds. Journal of Physical and Chemical Reference Data 18, 1111-1229.

https://doi.org/10.1063/1.555833

Sanni, M., Al-Abbad, M., Kokal, S., Dugstad, Ø., Hartvig, S., Huseby, O., 2018. Pushing the envelope of residual oil measurement: A field case study of a new class of inter-well chemical tracers. Journal of Petroleum Science and Engineering 163, 538-545.

https://doi.org/10.1016/j.petrol.2017.12.076

Scandura, G., Palmisano, G., Yurdakal, S., Tek, B.S., Özcan, L., Loddo, V., Augugliaro, V., 2016. Selective photooxidation of ortho-substituted benzyl alcohols and the catalytic role of ortho-methoxybenzaldehyde. Journal of Photochemistry and Photobiology A: Chemistry 328, 122- 128.

https://doi.org/10.1016/j.jphotochem.2016.05.022

Schwarzenbach, R.P., Gschwend, P.M., Imboden, D.M., 2002. Partitioning: Molecular Interactions and Thermodynamics, Environmental Organic Chemistry, pp. 57-96.

https://doi.org/10.1002/0471649643

Serres-Piole, C., Commarieu, A., Garraud, H., Lobinski, R., Preud'homme, H., 2011a. New Passive Water Tracers for Oil Field Applications. Energy & Fuels 25, 4488-4496.

https://doi.org/10.1021/ef2007485

Serres-Piole, C., Moradi-Tehrani, N., Lobinski, R., Preud'homme, H., 2011b. Direct sensitive simultaneous determination of fluorinated benzoic acids in oil reservoir waters by ultra high-performance liquid chromatography-tandem mass spectrometry. Journal of Chromatography A 1218, 5872-5877.

https://doi.org/10.1016/j.chroma.2011.06.028

Serres-Piole, C., Preud'homme, H., Moradi-Tehrani, N., Allanic, C., Jullia, H., Lobinski, R., 2012. Water tracers in oilfield applications: Guidelines. Journal of Petroleum Science and Engineering 98-99, 22-39.

https://doi.org/10.1016/j.petrol.2012.08.009

Shen, J., Chen, Y., Wu, S., Wu, H., Liu, X., Sun, X., Li, J., Wang, L., 2015. Enhanced pyridine biodegradation under anoxic condition: The key role of nitrate as the electron acceptor. Chemical Engineering Journal 277, 140-149.

https://doi.org/10.1016/j.cej.2015.04.109

Shook, G.M., Pope, G.A., Asakawa, K., 2009. Determining Reservoir Properties and Flood Performance From Tracer Test Analysis, SPE Annual Technical Conference and Exhibition. Society of Petroleum Engineers, New Orleans, Louisiana, p. 19.

https://doi.org/10.2118/124614-MS

Stephan, C., Dicko, M., Stringari, P., Coquelet, C., 2018. Liquid-liquid equilibria of water + solutes (acetic acid/ acetol/furfural/guaiacol/methanol/phenol/propanal) + solvents (isopropyl acetate/toluene) ternary systems for pyrolysis oil fractionation. Fluid Phase Equilibria 468, 49-57

https://doi.org/10.1016/j.fluid.2018.04.016

Strand, S., Standnes, D.C., Austad, T., 2006. New wettability test for chalk based on chromatographic separation of SCN− and SO42−. Journal of Petroleum Science and Engineering 52, 187-197.

https://doi.org/10.1016/j.petrol.2006.03.021

Surlyk, F., Stemmerik, L., Ahlborn, M., Harlou, R., Lauridsen, B.W., Rasmussen, S.L., Schovsbo, N., Sheldon, E., Thibault, N., 2010. The cyclic Rordal Member - a new lithostratigraphic unit of chronostratigraphic and palaeoclimatic importance in the upper Maastrichtian of Denmark. Bull. Geol. Soc. Den. 58, 89-98.

https://doi.org/10.37570/bgsd-2010-58-07

Takahashi, K., Hoshino, N., Noro, S.I., Nakamura, T., Akutagawa, T., 2014. A Crystal Structures, Dielectric, and CO2-Adsorption Properties of One-Dimensional Cu(II)(2)(Adamantane-1-carboxylate)(4)(pyrazine) (infinity) Coordination Polymers with Polar Ligands. Sci. Adv. Mater. 6, 1417-1424.

https://doi.org/10.1166/sam.2014.1831

Tang, J.S., 1992. Interwell Tracer Tests To Determine Residual Oil Saturation To Waterflood At Judy Creek Bhl'a'pool. PETSOC-91-04-01 31, 12. Tang, J.S., 1995. Partitioning Tracers and In-Situ Fluid Saturation Measurements. SPE-22344-PA 10, 33 - 39.

https://doi.org/10.2118/22344-PA

Tang, J.S., 2003. Propagation of phenol in aquifer with reversible adsorption, Proceedings of the Go-Expo Gas and Oil Exposition and the 4 Annual Canadian International Petroleum Conference and the 54 Annual Technical Meeting of the Petroleum Society of CIM : Global Challenges and Technology Integration. Petroleum Society of CIM, Canada.

https://doi.org/10.2118/2003-191

Tang, J.S., Harker, B., 1991. Interwell Tracer Test To Determine Residual Oil Saturation In A Gas-Saturated Reservoir. Part II: Field Applications. PETSOC-91-04-01 30, 34 - 42.

https://doi.org/10.2118/91-04-01

Tao, X., Zhou, S., Xiang, Z., Ma, J., Hou, R., Zhu, Y., Wei, X., 2017. Fabrication of continuous ZrB2 nanofibers derived from boron containing polymeric precursors. Journal of Alloys and Compounds 697, 318-325.

https://doi.org/10.1016/j.jallcom.2016.12.121

Tayyib, D., Al-Qasim, A., Kokal, S., Huseby, O., 2019. Overview of Tracer Applications in Oil and Gas Industry, SPE Kuwait Oil & Gas Show and Conference. Society of Petroleum Engineers, Mishref, Kuwait, p. 21.

https://doi.org/10.2118/198157-MS

Thomson, B.A., 1998. Atmospheric pressure ionization and liquid chromatography/mass spectrometry-together at last. Journal of the American Society for Mass Spectrometry 9, 187-193.

https://doi.org/10.1016/S1044-0305(97)00285-7

Valverde-Muñoz, F.J., Seredyuk, M., Muñoz, M.C., Znovjyak, K., Fritsky, I.O., Real, J.A., 2016. Strong Cooperative Spin Crossover in 2D and 3D FeII-MI,II Hofmann-Like Coordination Polymers Based on 2- Fluoropyrazine. Inorg. Chem. 55, 10654-10665.

https://doi.org/10.1021/acs.inorgchem.6b01901

Viig, S.O., Juilla, H., Renouf, P., Kleven, R., Krognes, B., Dugstad, O., Huseby, O.K., 2013. Application of a New Class of Chemical Tracers To Measure Oil Saturation in Partitioning Interwell Tracer Tests, SPE International Symposium on Oilfield Chemistry. Society of Petroleum Engineers, The Woodlands, Texas, USA.

https://doi.org/10.2118/164059-MS

Vorlicek, T.P., Helz, G.R., 2002. Catalysis by mineral surfaces: Implications for Mo geochemistry in anoxic environments. Geochimica et Cosmochimica Acta 66, 3679-3692.

https://doi.org/10.1016/S0016-7037(01)00837-7

Werle, P., Morawietz, M., Lundmark, S., Sörensen, K., Karvinen, E., Lehtonen, J., 2008. Alcohols, Polyhydric. In Ullmann's Encyclopedia of Industrial Chemistry, (Ed.).

https://doi.org/10.1002/14356007.a01_305.pub2

Whitehouse, B.G., 1985. Observation of abnormal solubility behavior of aromatic hydrocarbons in seawater. Marine Chemistry 17, 277-284.

https://doi.org/10.1016/0304-4203(85)90001-5

Wood, K.N., Tang, S., Luckasavitch, R.J., 1990. Interwell Residual Oil Saturation at Leduc Miscible Pilot, SPE Annual Technical Conference and Exhibition. Society of Petroleum Engineers, New Orleans, Louisiana.

https://doi.org/10.2118/20543-MS

Xie, W.-H., Shiu, W.-Y., Mackay, D., 1997. A review of the effect of salts on the solubility of organic compounds in seawater. Marine Environmental Research 44, 429-444.

https://doi.org/10.1016/S0141-1136(97)00017-2

Yamada, K., Brousseau, M., Honma, W., Iimura, A., Imase, H., Iwaki, Y., Kawanami, T., LaSala, D., Liang, G., Mitani, H., Nonomura, K., Ohmori, O., Pan, M., Rigel, D.F., Umemura, I., Yasoshima, K., Zhu, G., Mogi, M., 2017. Discovery of a Novel Piperidine-Based Inhibitor of Cholesteryl Ester Transfer Protein (CETP) That Retains Activity in Hypertriglyceridemic Plasma. Journal of Medicinal Chemistry 60, 8466- 8481.

https://doi.org/10.1021/acs.jmedchem.7b00900

Yu, A.-N., Zhang, A.-D., 2010. The effect of pH on the formation of aroma compounds produced by heating a model system containing lascorbic acid with l-threonine/l-serine. Food Chemistry 119, 214-219.

https://doi.org/10.1016/j.foodchem.2009.06.026

Yu, A.-N., Zhou, Y.-Y., Yang, Y.-N., 2017. Kinetics of browning and correlations between browning degree and pyrazine compounds in lascorbic acid/acidic amino acid model systems. Food Chemistry 221, 1678-1684.

https://doi.org/10.1016/j.foodchem.2016.10.119

Yu, W.H., Li, N., Tong, D.S., Zhou, C.H., Lin, C.X., Xu, C.Y., 2013. Adsorption of proteins and nucleic acids on clay minerals and their interactions: A review. Applied Clay Science 80-81, 443-452

https://doi.org/10.1016/j.clay.2013.06.003

Zhang, J., Wong, T.-F., Davis, D.M., 1990. Micromechanics of pressureinduced grain crushing in porous rocks. Journal of Geophysical Research: Solid Earth 95, 341-352.

https://doi.org/10.1029/JB095iB01p00341

Cover for Development of new oil/water partitioning tracers for the determination of residual oil saturation in the inter-well region of water-flooded reservoirs
Published
March 25, 2021