Synthesis and Antiscaling Evaluation of Novel Hydroxybisphosphonates for Oilfield Applications

Abstract

Organophosphorous compounds are still widely used as potential scale inhibitors in the upstream oil and gas industry, particularly in squeeze treatments as they have good adsorption properties on rock and are easily detectable. However, most phosphonate-based scale inhibitors have some drawbacks, such as poor biodegradability and various incompatibilities with the production system. The low toxicity of bisphosphonates motivated us to test a series of aliphatic and aromatic hydroxybisphosphonates as new oilfield scale inhibitors for calcium carbonate (calcite) and barium sulfate (barite) scales. Thus, the well-known bone-targeting drugs 3-amino-1-hydroxypropane-1,1-bisphosphonic acid (pamidronic acid, SI-1), 4-amino-1-hydroxybutane-1,1-bisphosphonic acid (alendronic acid, SI-2), 5-amino-1-hydroxypentane-1,1-bisphosphonic acid (SI-3), and hydroxyphenylmethylene-1,1-bisphosphonic acid (fenidronic acid, SI-6) are studied along with novel, specially designed bisphosphonates (1,4-dihydroxybutane-1,1,4,4-tetrayl)­tetrakisphosphonic acid (SI-4), (1,6-dihydroxyhexane-1,1,6,6-tetrayl)­tetrakisphosphonic acid (SI-5), and ((4- aminophenyl)­(hydroxy)­methylene)­bisphosphonic acid (SI-7) in a dynamic tube-blocking scale rig at 100 °C and 80 bar according to typical North Sea conditions. The scale inhibition performance of the new SIs was compared to that of the commercial 1-hydroxyethylidene bisphosphonic acid (HEDP) and aminotrismethylenephosphonic acid (ATMP). The results indicate that all synthesized hydroxybisphosphonates provide reasonable inhibition performance against calcite scaling and show good thermal stability at 130 °C for 7 days under anaerobic conditions.

Fosfomycin and Its Derivatives: New Scale Inhibitors for Oilfield Applications

“…This improvement may be because SI-3 is a linear structure with a hydroxyl group that could provide extra binding capabilities in contrast to the epoxide ring of SI-1 . 18 As mentioned earlier, the chemical structure of SI-3 is closely analogous to HPAA except for the carboxyl group. Due to this functional group, HPAA provided inhibition of more than 10% at concentrations of up to 5 ppm, which is not the case of SI-1 or SI-3 .…”

“…Similarly, our research group has developed a series of low toxicity bisphosphonates, commonly used as bone-targeting drugs, as new SIs against carbonate and sulfate oilfield scales. 18 …”

CoAl-LDHs@Fe3O4 decorated with cobalt nanowires and cobalt nanoparticles for a heterogeneous electro-Fenton process to degrade 1-hydroxyethane-1,1-diphosphonic acid and glyphosate

“…1 Phosphonate is a common type of organic phosphorus compound, 2,3 which is widely used in industries, because of its stability, threshold effect and scaling inhibition functional moieties. 3,4 However, most phosphonate-based materials have poor biodegradability, and therefore, traditional biological wastewater treatment plants have difficulty in completely mineralizing them. 3 1-Hydroxyethane-1,1-diphosphonic acid (HEDP) is a typical example of phosphonates.…”

“… 5 It has wide applications, first being used as a scale inhibitor in the water treatment industry. 6 Then, it is considered as an effective corrosion inhibitor in oil and gas industry, 4 iron and steel industry 7 and wastewater reverse osmosis (RO) systems. 8 HEDP has two phosphonic groups (C–PO 3 H 2 ).…”

New C‐3 Substituted 1H‐ and 2H‐Indazolephosphonic Acid Regioisomers: Synthesis, Spectroscopic Characterization and X‐Ray Diffraction Studies

“…The applications of bisphosphonates range from drugs, mostly of them for bone diseases therapy, to metal chelating agents, magnetic resonance imaging and scintigraphy, or diverse material sciences, such fuel cells membranes, solar cells dyes or coating agents. [37][38][39][40][41][42][43][44][45][46][47][48][49][50][51] Despite the difficulties in the preparation and purification of BP derivatives, the importance of their applications stimulate the search of new derivatives.…”