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Journal of Petroleum Engineering & Technology Original Research

Guanidine as a Starting Material for Preparing a Scale Inhibitor

  1. Othman O. Dakhil* Department of Pharmaceutical Chemistry, University of Benghazi
  2. Khaled A. Saleh Department of Chemistry, Libyan Academy
  3. Abdulqader A. Imrage Department of Chemistry, University of Benghazi
  4. Mahjoub A.M. Elaoud Al-Jouf Oil Technology Company

Abstract

Oilfield scale inhibition, which can obstruct fluid flow in pipelines, valves, and pumps during oil production and processing, is critical for preventing scale formation. Effective scale inhibitors (SIs) minimize downtime and enhance productivity by preventing the build-up of insoluble crystals in water systems. In oil processing, scale formation results from the precipitation of salts due to incompatible aqueous phases, leading to equipment blockage. Phosphonates are highly effective chelating agents for divalent and trivalent metal ions, capable of inhibiting crystal growth and scale formation under extreme conditions, such as high temperatures and fluctuating pH levels. These properties make them valuable in oilfields, cooling systems, desalination, pulp, paper, textiles, and detergents, where they function as SIs, chelating agents, and bleach stabilizers. In this study, ((1-methyl-3,3-bis(phosphonomethyl)guanidino) methyl) phosphonic acid was synthesized, and its effectiveness in reducing scale deposition in pipelines was evaluated. The compound chelates metal ions and inhibits crystal growth. Guanidine was selected as the starting material owing to its potential for phosphonate substitution. Although the initial aim was to introduce five phosphonate groups, steric hindrance and nitrogen bond stability resulted in the successful incorporation of these three groups. The structures and compositions of the synthesized compounds were confirmed by NMR, FT-IR, and mass spectrometry. Further evaluation of its scale inhibition efficiency will provide insights into its potential as an advanced inhibitor in oilfield applications.

Keywords

References (22)

  1. Kelland MA. Production Chemicals for the Oil and Gas Industry. 2014. doi:10.1201/b16648
  2. Garber KB, Vincent LM, Alexander JJ, Bean LJH, Bale S, Hegde M. Reassessment of Genomic Sequence Variation to Harmonize Interpretation for Personalized Medicine. The American Journal of Human Genetics. 2016;99(5):1140-1149. doi:10.1016/j.ajhg.2016.09.015
  3. Kiran YB, Devendranath Reddy C, Gunasekar D, Suresh Reddy C, Leon A, Barbosa LCA. Synthesis and anticancer activity of new class of bisphosphonates/phosphanamidates. European Journal of Medicinal Chemistry. 2008;43(4):885-892. doi:10.1016/j.ejmech.2007.05.014
  4. Sharma SK, Chaudhary A, Singh RV. Gray chemistry versus green chemistry: Challenges and opportunities. Rasayan J Chem. 2008;1:68–92.
  5. Kukhar VP, Hudson HR. Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity. Chichester: John Wiley & Sons; 2000.
  6. Emile C, Joseph R, inventors; Hooker Chemical Corp, assignee. Monoesters of phosphonic acids and alkali metal or alkaline earth metal salts thereof. United States patent US 3358057. 1967 Dec 12.
  7. Jordan MM, Mackay EJ. Scale Control in Chalk Reservoirs: The Challenge of Understanding the Impact of Reservoir Processes and Optimizing Scale Management by Chemical Placement and Retention—From the Laboratory to the Field. SPE Middle East Oil and Gas Show and Conference. 2007. doi:10.2118/105189-ms
  8. Demadis KD, Yang B, Young PR, Kouznetsov DL, Kelley DG. Rational Development of New Cooling Water Chemical Treatment Programs for Scale and Microbial Control. Advances in Crystal Growth Inhibition Technologies. 215-234. doi:10.1007/0-306-46924-3_16
  9. Mady MF, Bagi A, Kelland MA. Synthesis and Evaluation of New Bisphosphonates as Inhibitors for Oilfield Carbonate and Sulfate Scale Control. Energy & Fuels. 2016;30(11):9329-9338. doi:10.1021/acs.energyfuels.6b02117
  10. Kim SH, Semenya D, Castagnolo D. Antimicrobial drugs bearing guanidine moieties: A review. European Journal of Medicinal Chemistry. 2021;216:113293. doi:10.1016/j.ejmech.2021.113293
  11. Zamperini C, Maccari G, Deodato D, Pasero C, D’Agostino I, Orofino F, et al. Identification, synthesis and biological activity of alkyl-guanidine oligomers as potent antibacterial agents. Scientific Reports. 2017;7(1). doi:10.1038/s41598-017-08749-6
  12. Moussa A. Two Functional Guanidine Groups Are Responsible For the Biological Activity of Streptomycin and Functionally Equivalent Molecules. Journal of Chromatography & Separation Techniques. 2014;05(06). doi:10.4172/2157-7064.1000e126
  13. Dakhil O, Yahya Y, Abdalkrim H, Eltawaty S. Chemical separation of compounds from antituberculosis drug and their antibacterial biological activity. Alq J Med App Sci. 2022;5(1):274–281. doi:10.5281/zenodo.6581958.
  14. Jiménez PD. Improving squeeze scale inhibitor adsorption and flow back characteristics with surfactants [thesis]. Stavanger: University of Stavanger; 2014.
  15. Ebetino FH, Francis MD, Rogers MJ, Russell RGG. Mechanisms of action of etidronate and other bisphosphonates. Rev Contemp Pharmacother. 1998;9:233–243.
  16. Sparidans RW, Twiss IM, Talbot S. Bisphosphonates in bone diseases. Pharm World Sci. 1998;20:206–213. doi:10.1023/A:1008626026484.
  17. Maeda K. Metal phosphonate open-framework materials. Microporous and Mesoporous Materials. 2004;73(1-2):47-55. doi:10.1016/j.micromeso.2003.10.018
  18. Rodan GA, Martin TJ. Therapeutic Approaches to Bone Diseases. Science. 2000;289(5484):1508-1514. doi:10.1126/science.289.5484.1508
  19. Hirabayashi H, Sawamoto T, Fujisaki J, Tokunaga Y, Kimura S, Hata T. Dose‐dependent pharmacokinetics and disposition of bisphosphonic prodrug of diclofenac based on osteotropic drug delivery system (ODDS). Biopharmaceutics & Drug Disposition. 2002;23(8):307-315. doi:10.1002/bdd.323
  20. Popov KI, Kovaleva NE, Rudakova GY, Kombarova SP, Larchenko VE. Recent state-of-the-art of biodegradable scale inhibitors for cooling-water treatment applications (Review). Thermal Engineering. 2016;63(2):122-129. doi:10.1134/s0040601516010092
  21. Nowack B. Environmental chemistry of phosphonates. Water Research. 2003;37(11):2533-2546. doi:10.1016/s0043-1354(03)00079-4
  22. Elayatt AK, Altarhoni HK, Elaoud MAM. Evaluation of diethylene triamine-pentamethylene phosphonic acid (DTPMP) as a scale inhibitor of calcium carbonate scales in oil field water. Am J Energy Res. 2016;5(12):130–142.
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