Overview of the Synthesis of Salts of Organophosphonic Acids and Their Application to the Management of Oilfield Scale

Mady, Mohamed F.; Kelland, Malcolm A.

doi:10.1021/acs.energyfuels.7b00708

Cited by 54 publications

(54 citation statements)

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“…This functional group was incorporated in a broad diversity of molecules and polymers to introduce specific properties including water solubility, coordination or supramolecular properties. Several books, book chapters or reviews have been focused on the construction of the P–C bond [ 1 ], on the description of the different classes of phosphorus-containing functional groups [ 2 ], on specific applications (hybrid materials [ 3 ], surface modification [ 4 ], oil industry [ 5 ]) or dedicated to a family of compounds (e.g., aminophosphonic acids [ 6 ], organometallic phosphonic acids [ 7 ]). However, no recent review was focused on the different methods that can be employed to prepare phosphonic acids which is a function needed to address numerous applications that are summarized in the first part of this review (section 2).…”

Section: Reviewmentioning

confidence: 99%

Phosphonic acid: preparation and applications

Sevrain¹,

Berchel²,

Couthon³

et al. 2017

Beilstein J. Org. Chem.

137

103

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The phosphonic acid functional group, which is characterized by a phosphorus atom bonded to three oxygen atoms (two hydroxy groups and one P=O double bond) and one carbon atom, is employed for many applications due to its structural analogy with the phosphate moiety or to its coordination or supramolecular properties. Phosphonic acids were used for their bioactive properties (drug, pro-drug), for bone targeting, for the design of supramolecular or hybrid materials, for the functionalization of surfaces, for analytical purposes, for medical imaging or as phosphoantigen. These applications are covering a large panel of research fields including chemistry, biology and physics thus making the synthesis of phosphonic acids a determinant question for numerous research projects. This review gives, first, an overview of the different fields of application of phosphonic acids that are illustrated with studies mainly selected over the last 20 years. Further, this review reports the different methods that can be used for the synthesis of phosphonic acids from dialkyl or diaryl phosphonate, from dichlorophosphine or dichlorophosphine oxide, from phosphonodiamide, or by oxidation of phosphinic acid. Direct methods that make use of phosphorous acid (H3PO3) and that produce a phosphonic acid functional group simultaneously to the formation of the P–C bond, are also surveyed. Among all these methods, the dealkylation of dialkyl phosphonates under either acidic conditions (HCl) or using the McKenna procedure (a two-step reaction that makes use of bromotrimethylsilane followed by methanolysis) constitute the best methods to prepare phosphonic acids.

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Section: Reviewmentioning

confidence: 99%

Phosphonic acid: preparation and applications

Sevrain¹,

Berchel²,

Couthon³

et al. 2017

Beilstein J. Org. Chem.

137

103

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“…Methylamine hydrochloride, ethylamine (70%), 1-butylamine (99%), hexylamine (99%), 1-octylamine (99%), 1-dodecylamine (99%), formaldehyde (36.5% aqueous solution), phosphorus acid and hydrochloric acid (37% aqueous solution) were supplied from commercial sources and used as received, without further purification. All diphosphonic acid molecules are synthesized via the Mannich-type reaction (also known as Irani-Moedritzer) according to appropriately modified published procedures [23,24,25], see Figure 1. The detailed synthesis protocols are included in the Supplementary Information (SI).…”

Section: Synthesis Of Diphosphonic Acid Corrosion Inhibitorsmentioning

confidence: 99%

Homologous alkyl side-chain diphosphonate inhibitors for the corrosion protection of carbon steels

Moschona

Pleşu

Colodrero

et al. 2021

Chemical Engineering Journal

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C8-D), dodecylamine-N,N-bis(methylenephosphonate) (DBMP, C12-D), with carbon steel surfaces are studied by XPS at pH = 3.0. Structurally, they all possess two methylenephosphonate moieties connected to a single N atom. The third substituent on N is a non-polar, variable-length alkyl chain, -(CH 2 ) x CH 3 , where x = 0 (C1-D), 1 (C2-D), 3 (C4-D), 5 (C6-D), 7 (C8-D), and 11 (C12-D). XPS studies (on pristine solid diphosphonate samples and also on carbon steel specimens, immersed in aqueous solutions), indicate significant deprotonation of the diphosphonic acid molecules upon interaction with the 2 metallic surface. They also prove that this surface interaction results in adsorption on the surface via the deprotonated phosphonic acid moieties. The adsorption of inhibitors on the metal surface was investigated by potentiodynamic polarization and electrochemical impedance spectroscopy. The changes detected in the charge transfer resistance (R ct ) and constant phase element (CPE) independently confirm inhibitors adsorption on metal surface. Attenuated Total Reflectance-Fourier Transform Infrared (ATR-FTIR) spectroscopy and Scanning Electron Microscopy was used to investigate the nature of deposited film. Small alkyl chain diphosphonates (C1-D, C2-D and C4-D) exhibited lower corrosion resistance due to the thin, porous and/or incomplete layer formed on carbon steel surface. Longer alkyl chain molecules (C6-D, C8-D and C12-D) were found to adsorb more efficiently and form a more organized and thicker layer. The best results were obtained in the case of C8-D (lower corrosion current, higher R ct and surface coverage). In the presence of C8-D the corrosion rate was reduced by a factor of 6.

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“…16 Furthermore, the drawbacks of commercial aminomethylenephosphonate SIs motivated us to synthesize and evaluate new SIs based on the aminomethylene-free phosphonate group. 11 This study aims to synthesize aminomethylene-free phosphonates derived from fosfomycin as the starting compound and evaluate their performance as oilfield SIs. Fosfomycin belongs to the class of phosphonic antibiotics used for the treatment of urinary tract infections (UTIs).…”

Section: Introductionmentioning

confidence: 99%

“…Polyphosphates, phosphate esters, non-polymeric phosphonates, aminophosphonates, polyphosphonates, polysulfonates, and polycarboxylates are among the most common classes of SIs used in oilfield applications. 11 Most current SIs have a trade-off between inhibition performance and costs. However, they lack other important characteristics that must be considered before their application in the field, such as calcium tolerance and biodegradability.…”

Section: Introductionmentioning

confidence: 99%

Fosfomycin and Its Derivatives: New Scale Inhibitors for Oilfield Applications

Mady

Ortega

2022

ACS Omega

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Aminomethylenephosphonate-based scale inhibitors (SIs) have been widely studied and recognized for several decades to mitigate various oilfield scales. However, most of these compounds afforded several drawbacks, such as poor biodegradability and intolerance with the production system. As environmental regulations become more rigid, new production chemicals must adhere to certain criteria to qualify for use in the oil and gas industry, particularly in areas with strict regulations, such as the Norwegian Sea. The low toxicity of fosfomycin encouraged us to test fosfomycin and related molecules as new aminomethylene-free phosphonate SIs for calcite and gypsum scales. The tested chemicals are fosfomycin disodium salt ( SI-1 ), fosfomycin trometamol ( SI-2 ), and hydrolysis of fosfomycin called 1,2-dihydroxypropyl phosphonic acid ( SI-3 ). The inhibition efficiency of all these chemicals was evaluated against calcite and gypsum scales compared to commercial oilfield scale inhibitor hydroxyphosphonoacetic acid ( HPAA ) according to the NACE Standard TM0374-2007. In addition, the calcite scale inhibition efficiency of all aminomethylene-free phosphonate SIs ( SI-1 to SI-3 and HPAA ) was investigated based on the Heidrun oilfield, Norway. Moreover, we have reported the calcium compatibility of these chemicals at various concentrations of SIs and calcium ions at 80 °C over 24 h. All new aminomethylene-free phosphonate SIs showed good gypsum and calcite inhibition performance. It was also found that all tested chemicals derived from fosfomycin demonstrated excellent compatibility with calcium ions of up to 1000 ppm throughout the 24 h experiment period compared to HPAA .

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Overview of the Synthesis of Salts of Organophosphonic Acids and Their Application to the Management of Oilfield Scale

Cited by 54 publications

References 106 publications

Phosphonic acid: preparation and applications

Phosphonic acid: preparation and applications

Homologous alkyl side-chain diphosphonate inhibitors for the corrosion protection of carbon steels

Fosfomycin and Its Derivatives: New Scale Inhibitors for Oilfield Applications

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