Overview of the Synthesis of Salts of Organophosphonic Acids and

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Overview of the Synthesis of Salts of Organophosphonic Acids and Their Application to the Management of Oilfield Scale Mohamed F. Mady*,†,‡ and Malcolm A. Kelland† †

Department of Mathematics and Natural Sciences, Faculty of Science and Technology, University of Stavanger, 4036 Stavanger, Norway ‡ Department of Green Chemistry, National Research Centre, 33 El Bohouth Street, Dokki, Giza 12622, Egypt ABSTRACT: Phosphonate-based scale inhibitors (SIs) have been used in the oil industry for decades. They are excellent inhibitors particularly of Group II sulfate scales and offer several advantages over other classes of oilfield SIs that contain predominantly carboxylate or sulfonate groups. For example, phosphonates show superior binding to reservoir rocks, giving them long squeeze lifetimes. The superior binding means non-polymeric phosphonate molecules can be used, whereas polymers with carboxylate or sulfonate groups need to be polymeric. Phosphonates are also easily detected by atomic absorption spectroscopy. Most phosphonate-based SIs are aminomethylenephosphonates, yet there are many other methods to introduce the phosphonate group into an organic molecule. This review surveys practical routes to synthesize phosphonate-based molecules and investigations that have been carried out for their use as oilfield SIs.

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INTRODUCTION Scale formation is the deposition of sparingly soluble inorganic salts from aqueous solutions. Oilfield wells producing water are often likely to develop deposits of inorganic scale at some time during their lifetime. Scale can deposit on almost any surface, so that, once a scale layer is first formed, it will continue to become thicker unless treated. Scale can block pore throats in the near-well bore region or in the well itself, causing formation damage and loss of well productivity.1,2 It can also deposit on equipment in the well, causing it to malfunction. Scale can occur anywhere along the production conduit, narrowing the internal diameter and blocking flow, and can even occur as far along as the processing facilities.3,4 Alongside corrosion and gas hydrates, scale formation is probably one of the three biggest water-related production problems and needs to be anticipated in advance to determine the best treatment strategy.5−8 The four commonest scales encountered in the oil industry are calcium carbonate (calcite and aragonite), and the sulfate salts of calcium (gypsum), strontium (celestite), and barium (barite).1 Carbonate scaling is dependent upon the equilibrium between bicarbonate, carbonate, and carbon dioxide relative to changes in the temperature and pressure.9 Metal ions, such as calcium or iron(II) ions, can form insoluble carbonates, as illustrated in the following equation:

useful method of preventing scale formation in the oil and gas industry is the use of scale inhibitors (SIs). SIs work by preventing either nucleation and/or crystal growth of the scale. They are deployed in several ways but most commonly in downhole squeeze treatments or by continuous injection at the well head.11−13 Phosphonic acids are organophosphorus compounds containing C-PO(OH)2 moieties.14,15 Phosphates, which contain P−O−C bonds, are less hydrolytically stable and less compatible with calcium ions. Therefore, they find limited use in oil industry applications. Phosphonic acid and their salts, phosphonates, have a wide range of applications in the agricultural, chemical, and pharmaceutical industries.16−20 Natural phosphonic acids include 2-aminoethylphosphonate and phosphonoacetic acid. Some anthropogenic phosphonic acids are good complexing and chelating agents.21,22 For example, it is well-known that phosphonic acids play an efficient role in controlling apatite nucleation and crystal growth.31 In addition, organophosphonic acid compounds and their salts are an important class of SIs used for oilfield scale control.23−30 Some of them are small non-polymeric SI molecules with only a few phosphonate groups, while others are polymeric compounds with many attached phosphonate groups.1 Often the phosphonate is attached as an aminomethylenephosphonate group, where the amine group also plays a part in the inhibition process acting as a Lewis base ligand. Placing phosphonate groups within the SI can be helpful to determine the concentration of the SI in the produced water. This information, if interpreted correctly, can be useful for determining when to resqueeze a well if the SI concentration is close to dropping to the minimum inhibitor concentration (MIC) for complete scale inhibition.32 These and other

Ca 2 + + CO32 − → CaCO3

In addition, Group II metal ions, except magnesium, present in the formation water can form sulfate scales when mixed with sulfate ions. This can occur when injected seawater is present, either as part of a well treatment or from seawater breakthrough for increased oil recovery. BaSO4 is the least soluble sulfate scale and hardest to control. Ba 2 + + SO4 2 − → BaSO4

Received: March 9, 2017 Revised: April 18, 2017 Published: April 20, 2017

Scale remediation processes must be easy to deploy and nondamaging to the wellbore, tubing, and reservoir.10 The most © XXXX American Chemical Society

A

DOI: 10.1021/acs.energyfuels.7b00708 Energy Fuels XXXX, XXX, XXX−XXX

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Figure 1. Schematic presentation of (A) synthesis of phosphonate esters by the reaction of active functional groups of polymeric and non-polymeric molecules, e.g., hydroxyl, aldehyde, amino, or CC double bond with H-phosphonate dialkyl esters, (B) hydrolysis of phosphonate esters, and (C) acidic hydrolysis of phosphonate esters incorporating amide groups.

properties discussed later make phosphonates an attractive class of oilfield SI, especially if they are also environmentally friendly. Various synthetic routes have been investigated to synthesize phosphonic acids, including carbon−phosphorus, carbon− carbon, or carbon−nitrogen bond formation.33−38 Most of these methods depend upon two-step reaction pathways, as shown in Figure 1, in which the first step is the Michaelis− Arbuzov or Michaelis−Becker reaction. This uses alkyl phosphonates, which contain a P−H bond, as phosphonating reagents. Examples include dimethyl phosphite and diethyl phosphite. When reacted with a base followed by a nucleophilic substitution of phosphorus on an haloalkane, this affords an alkyl phosphonate with a new P−C bond. In the second step, the hydrolysis of phosphonate esters is mediated by trimethylsilyl chloride (TMSCl) or hydrochloric acid, as shown in Figure 1A.39−42 Unfortunately, starting from phosphonate esters is usually not a viable economical option for the oilfield industry. In addition, it is hard to control the hydrolysis process in the presence of a strong acid, such as HCl, because chemicals containing amide and/or ester groups, such as proteins, would be degraded by acid hydrolysis (Figure 1B).43 A rare example of an industrial SI that is manufactured by hydrolysis of a H-phosphonate diester is 1,2,4-phosphonobutanetricarboxylic acid (PBTCA), as shown in Figure 2.44 The entry point to PBTCA synthesis is via phosphonosuccinic acid tetraalkyl esters. These are produced in a Michael addition reaction between a dialkyl phosphite (such as dimethyl phosphite) and maleic acid or fumaric acid dialkyl esters in the presence of alkali metal alkoxides. The reaction of these

Figure 2. Synthesis of 1,2,4-phosphonobutanetricarboxylic acid (PBTCA).

tetraalkyl esters with methyl acrylate affords a pentamethyl ester, which, when hydrolyzed, gives PBTCA. To our knowledge, there is no review on the synthesis of phosphonic acid analogues without using H-phosphonate dialkyl esters. The aim of this review is, therefore, to provide an overview of different synthetic approaches to manufacturing phosphonic acid derivatives, which avoid the step of hydrolysis of phosphonate esters. Furthermore, we will present the importance of organophosphonic acids and their salts for the oil and gas industry. There is an increasing focus on using environmentally friendly SIs to approve the offshore regulations (OSPARCOM) for oilfield chemicals.45 Therefore, we have also summarized all recent publications and patents devoted to the synthesis of modified biodegradable cores attached to phosphonic acid moieties. B


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SYNTHESIS OF AMINOMETHYLENEPHOSPHONIC ACIDS Moedritzer−Irani Reaction. The Moedritzer−Irani reaction was discovered in 1966 by Kurt Moedritzer and Riyad R. Irani.46 A series of aminomethylenephosphonic acids can be prepared by the reaction of an amine, formaldehyde, and phosphorous acid in the presence of a catalytic amount of hydrochloric acid under conventional and microwave irradiation conditions, as given in Figure 3.47 A plausible mechanism

triethylenetetramine, with epichlorohydrin and then reacting the amine groups with formaldehyde and phosphorous acid to give the final product, a N-phosphonomethylated amino-2hydroxypropylene polymer having a molecular weight of between about 300 and 5000.55 The amino group in aminomethylenephosphonic acids increases the metal binding abilities by the interaction of both amine and phosphonic acid to form greater metal−ligand (ML) complex stability than a phosphonic acid group alone.56 Aminomethylenephosphonic acids have significant applications for continuous injection but particularly for SI squeeze treatments. Aminomethylenephosphonate groups have excellent chemisorption properties onto the rock matrix as well as fairly good thermal stability, making SIs based around this functional group good for long squeeze lifetimes.57 The mechanistic understanding of the chemistry of the rock− aminomethylenephosphonic acid (SI) interactions has been reported.58,59 However, there are some limitations to the use of some aminomethylenephosphonic acid SI derivatives in the presence of high calcium ion concentrations. Too much calcium ions lead to incompatibility with the SI, leading to precipitation and deposition, not of inorganic scale but a calcium−SI complex. This can cause poor placement of the SI and formation damage.60 In addition, the seawater biodegradation of many aminomethylenephosphonic acids is low. Attempts to make more environmentally acceptable and biodegradable SIs containing phosphonic acid groups have been reported.29 One of these attempts to find greener SIs involves the phosphonation of amino acids. Devaux et al. have described a Moedritzer−Irani reaction for a series of amino acids, e.g., L-phenyl alanine, L-isoleucine, D,L-leucine, L-valine, Lglutamic acid, and L-lysine hydrochloride.61,62 The modified amino acids were tested for sulfate scale inhibition and seawater compatibility with calcium ion. Bodnar et al. have patented the partial alkylenephosphonation of L-lysine hydrochloride as a commercial green SI for squeeze treatment, as shown in Figure 6.63 These alkylenephosphonic acids exhibit improved environmental properties and good inhibition performance for oilfield scale compared to the fully substituted species. Common non-phosphorus environmentally friendly SIs that have been used in the oil and gas industry include polyaspartates and carboxymethyl inulin (CMI).64 Chitosan is an aminopolysaccharide and widely reported as a potential biodegradable polymer for use in medical and industrial applications.65−73 Heras et al. have synthesized aminomethylphosphonic acid chitosan by the reaction of amino

Figure 3. General equation for the synthesis of aminomethylenephosphonic acids by the Moedritzer−Irani reaction. A double substitution on a primary amine is shown here.

for this method of introducing methylenephosphonate groups into molecules attached to primary and secondary amines, polyamines, and ammonia was reported by Zon et al.48 The commercial chelate N-(phosphonomethyl)iminodiacetic acid (PMIDA) and the well-known herbicide N(phosphonomethyl)glycine (“glyphosate”) are made by the Moedritzi−Irani reaction (Figure 4).

Figure 4. (Left) N-(Phosphonomethyl)iminodiacetic acid (PMIDA) and (right) N-(phosphonomethyl)glycine (“glyphosate”).

Many commercial aminomethylenephosphonic acid SIs are also synthesized using the Moedritzer−Irani reaction.49−54 Figure 5 summarizes the structures of common oilfield SIs with t h i s f u n c t io n a l g r o up . T h e y i n c l u d e a m i n o t r i s (methylenephosphonic acid) (ATMP), ethylenediamine tetra(methylenephosphonic acid) (EDTMP), diethylenetriaminepenta(methylenephosphonic acid) (DTPMP), hexamethylenediaminetetra(methylenephosphonic acid) (HDTMP), and bis(hexamethylenetriaminepenta(methylenephosphonic acid)) (BHMTMP). Phosphonomethylated polyamines are particularly useful for barite scale inhibition and for squeeze applications. They are made by reacting a small polyalkyleneamine, such as

Figure 5. Common oilfield SIs containing aminomethylenephosphonate groups. C


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Figure 6. Phosphonation of L-lysine hydrochloride by the Moedritzer−Irani reaction as SI.

groups in chitosan with phosphorous acid and formaldehyde in the presence of glacial acetic acid as a catalyst instead of HCl, to avoid the hydrolysis of chitosan (Figure 7).74 Recently, Dhara

Hyperbranched polymers and dendrimers have drawn much recent attention as a result of their unique chemical and physical properties as well as potential medical and industrial applications, such as for coating additives, drug and gene delivery, macromolecular building blocks, and nanotechnology.80−85 Hyperbranched polyethylenimines (HPEIs) are a commercial class of hyperbranched polyamines, which are prepared by cationic ring opening of aziridine.86,87 Villemin et al. have reported the phosphonated polyethylenimines (PEIPs) by the route of Moedritzer−Irani under microwave irradiation, as shown in Figure 8. Totally PEIP was used as an anticorrosion inhibitor as well as an efficient resin for metal ion extraction. Furthermore, the partially PEIP-functionalized silver nanoparticles have been investigated as potential antibacterial agents.88 The addition of several anionic vinylic monomers (vinyl phosphonic, vinyl sulfonic, acrylic, maleic, and aconitic acids) to HPEIs produced a series of polymers that were investigated for their performance as carbonate and sulfate SIs.89 Reasonable inhibition performance was observed. In addition, HPEI with a molecular weight of 1200 functionalized with maleic or aconitic acid showed seawater biodegradation rates of up to 34% in 28 days, increasing to over 60% in 60 days. Zhang et al. have patented a new class of phosphonic acid SIs for oilfield scale based on a trimethylolpropane core with peripheral dendrimeric amino groups.90 The amino groups are modified with methylenephosphonic acid groups, as shown in Figure 9, wherein n is an integer from 1 to 5. This phosphonicacid-terminated dendrimer has high calcium tolerance and excellent scale inhibition of calcium carbonate, calcium sulfate, and barium sulfate. It is proposed for use in industrial water systems of circulating cooling water, oilfield flooding, and reverse osmosis and particularly suitable for water treatment needing high calcium tolerance. Reddmore et al. have developed a series of N,N-dialkylene phosphonic acids of alkylene diamines as SIs for carbonate and sulfate scale, as shown in Figure 10A.91 The results showed that

Figure 7. Synthesis pathway of phosphonated chitosan under reflux and microwave irradiation conditions.

et al.75 have performed the first synthesis of N-methylene phosphonic acid chitosan under microwave irradiation. The product yield and reaction time were improved as well as the molecular weight and viscosity. Demadis et al. have reported zwitterionic phosphomethylated chitosan (PCH) as a good inhibitor for silicic acid condensation at concentrations of 40− 200 ppm.76 In addition, blends of PCH with polyethylenimine (PEI) were shown to be effective inhibitors of silicic acid condensation using 20 ppm of each polymer.77,78 Phosphonation of chitosan amino groups by the introduction of phosphonic acid onto amino groups by a one-pot Moedritzer−Irani reaction has been reported in numerous papers.79 In addition, other routes have been reported in the literature for the phosphonation of chitosan without using the Moedritzer− Irani reaction.65 D


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Figure 8. Schematic of partial and total phosphonation of hyperbranched polyethylenimines (PEIs).

the phosphonic acid SIs attached to amino groups gave an improved inhibition effect at high temperatures. Several patents describe the synthesis of phosphonic-acid-based SIs with an attached alkanol group for high-temperature, high-pressure applications. 92−94 For example, ethanolamine-N,N-bis(methylenephosphonate) (EBMP) was prepared by reacting together ethanolamine, formaldehyde, and phosphorous acid in the presence of hydrochloric acid. A cyclic ester of EBMP is also formed at this stage (Figure 10B). EPMB is a commercially available highly effective SI for carbonate and sulfate scale at high temperatures, up to 120−150 °C.95 It was also reported that the acyclic ester of EPMP showed poor scale inhibition for oilfield scale. Davis et al.96 have performed the hydrolysis of EBMP cyclic ester by heating the mixture solution of EBMP and its cyclic ester in strongly alkaline conditions at a temperature of 100 °C to give a higher ratio of the nonesterified product. Sulfonated polymers, such as polyvinylsulfonic acid (PVS), are particularly useful for high-temperature squeeze applications for inhibiting sulfate scale. They also show better calcium compatibility than phosphonate SIs.97−100 In an attempt to capture the useful properties of both functional groups, Derek et al. have synthesized a series of oilfield SIs combining both sulfonate and aminomethylenephosphonate groups.101 They are made by reacting an amine with propane sultone,

Figure 9. Synthesis of a phosphonic-acid-terminated dendrimer with a trimethylolpropane core.

Figure 10. Synthesis of phosphonic acid SIs functionalized with hydroxyl and/or amino groups. E


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chlorotoluene with phosphorous acid and phosphorus trichloride at 80−90 °C, as shown in Figure 14.110 EDTMP is normally delivered as its sodium salt and is used in water treatment as an anti-scaling and anti-corrosion agent. Ueda et al. have invented a method of processing imagewise exposed silver halide color photographic material based on a phosphonation of aromatic derivatives containing iminodiacetic acid, as presented in Figure 15.111

formaldehyde, and phosphorous acid, as shown in Figure 11. These compounds gave improved inhibition of carbonate and sulfate scale at high temperatures compared to prior art compounds at the time.

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BISPHOSPHONATES (BPS) BPs are pyrophosphate analogues, characterized by a P−C−P moiety, in which oxygen in the P−O−P moiety has been replaced by a carbon atom, as shown in Figure 16.112 BPs were discovered in the 18th century, and they were initially used to inhibit scale and corrosion as well as for use as complexing agents in the textile, fertilizer, and oil industries.113−117 In addition to the industrial applications, they have been used as drugs for the treatment of various bone diseases.118−120 In this section, we will present one-pot chemical synthesis routes for BPs and their salts without using the hydrolysis methods of BP di- and/or tetra-esters as well as their application in the oilfield as scale and corrosion inhibitors. One class of BPs are the aminoalkylidenediphosphonic acids. This class of phosphonates has been used as chelating agents, surfactants, corrosion inhibitors, and SIs. Figure 17 summarized the known methods used for the preparation of aminoalkylidenediphosphonic acid derivatives. They were first prepared in a 50% yield by the reaction of acetonitrile with phosphorus trihalides in the presence of phosphorous acid. The reaction mixture is subsequently treated with water, as shown in method A of Figure 17.121−123 Kaabak et al. have improved the synthesis of aminoalkylidendiphosphonic acids under mild conditions, starting from commercial phosphorus trichloride and nitrile in the presence of water at room temperature, and, without using phosphorous acid, afforded aminobisphosphonates in high yield, as explained in method B of Figure 17.124 In addition, Chai et al. have patented a series of organo-α-aminodiphosphonic acids by reacting mono- and/or bis-nitriles with phosphorous acid at elevated temperatures, as shown in method C of Figure 17.125 These aminoalkylidendiphosphonic acids showed an improved carbonate scale inhibition effect compared to a blank test. Very recently, we have synthesized and investigated a series of novel BPs with one or two aminobisphosphonate groups, −C(NH2)(PO3H2)2. We have studied their seawater biodegradability, calcium carbonate and barium sulfate scale inhibition, and compatibility with Ca2+ ions. In addition, we functionalized aminophosphonates with methylenephosphonate groups using the Moedritzer−Irani reaction to give new classes of SIs, as shown in Figure 18.126 It was found that the new BP compounds showed good calcium carbonate and barium sulfate scale inhibition compared to the commercial products, DTPMP and ATMP, as well as reasonable seawater biodegradation (>20%) in some cases. In addition, it was reported that some aminoalkylidendiphosphonic acids have been used as reactive intermediates for the synthesis of anti-scalant and anti-corrosion agents. 3,5Bis(1,1-diphosphonoalkylaminomethyl)-4-hydroxybenzenesulfonic acid, 3-(1,1-diphosphonoalkylaminomethyl)-4-hydroxybenzenesulfonic acid, and their salts were synthesized by the reaction of 1,1-diphosphonoethylamine, 4-hydroxybenzenesulfonic acid, and formaldehyde at pH 9−10, as shown in Figure 19.127

Figure 11. Synthesis of amino−phosphonic−sulfonic acid SIs.

A series of phosphonic acids containing aromatic and heterocycle rings have been synthesized and used as water treatment agents.102,103 In addition, it is known that some phosphonic acids, including heterocycles, are effective corrosion inhibitors for metals. Recently, Borghei et al. synthesized a new imidazoline derivative, {[(benzimidazol-2-ylmethyl)imino]bis(methylene)}bis(phosphonic acid) (BMIBMBP), as shown in Figure 12. This molecule gave calcium carbonate scale inhibition and carbon steel corrosion inhibition.104

Figure 12. Synthesis route of the imidazoline derivative as a scale and corrosion inhibitor.

Phosphonating chloroalkyl amine hydrochloride has been carried out using the Moedritzer−Irani reaction to afford chloroalkyliminobis(methylene phosphonic acid)s. These molecules have been used as reactive intermediates in many industrial and pharmaceutical applications for introducing aminomethylenephosphonate groups into a chemical.105 For example, Notte et al. have reported some novel SIs by treatment of 3-chloropropyliminobis(methylene phosphonic acid) (CPIBMPA) with amino, hydroxyl, and thiol compounds in an aqueous medium having a pH of 8 or higher.106−108 Figure 13 summarizes some reactions of CPIBMPA. Reactions with alkanolamines (ethanolamine), polyamines (linear polyethylenimine), amino acids (glycine, D,L-alanine, β-alanine, glutamic acid, aspartic acid, glycine, and L-serine), thiols (dodecyl thiol), thioacids (thioglycolic acid and L-cysteine), and phenols have also been reported. Phosphonation of Iminodiacetic Acids. As indicated above, most amino(bismethylenephosphonates) (ABMPs), with two methylenephosphonate groups on the same amine group, are synthesized by the treatment of primary amines with phosphorous acid and aqueous HCl but with varying yields. In contrast, Schwarzenbach et al. have developed a one-step process for preparing ABPMs in high yields by treating iminodiacetic acid derivatives with phosphorous acid and phosphorus trichloride to afford N,N-methylene bisphosphonates.109 Mishra et al. improved the process for preparation of ethylenediaminetetramethylenephosphonic acid (EDTMP) by the reaction of ethylenediaminetetraacetic acid (EDTA) in F


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Figure 13. Phosphonation of amino, thiol, and hydroxy groups by 3-chloropropyliminobis(methylene phosphonic acid) (CPIBMPA).

Figure 14. Synthesis of ethylenediaminetetramethylenephosphonic acid (EDTMP) by phosphonation of ethylenediaminetetraacetic acid (EDTA).

Figure 15. Phosphonation of aromatic compounds containing iminodiacetic acid groups.

1-Hydroxyethylidene diphosphonic acid (HEDP) and its tetrasodium or potassium salts are well-known SIs and corrosion inhibitors.1 The introduction of the hydroxyl group increases the binding affinity of the molecule to Group II scales. Van Rosmalen et al. have studied the influences of amino and hydroxyl BPs on the growth inhibition of barium sulfate crystals. The results have been interpreted using a hypothesis that growth inhibition occurs as a result of simultaneous coordination of the cations and hydrogen bonding of the anions at the active growth spots on the crystal surface.129 Vepsäläinen et al. have invented a novel approach to remove metals from aqueous solutions using a series of BPs incorporating different functional groups, e.g., amino, hydroxyl, and an aromatic ring.130,131 11-Amino-1-hydroxyundecylidene1,1-bisphosphonic acid (N10O in Figure 21) has been

Figure 16. (Left) Structure of polyphosphoric acid and (right) general structure of bisphosphonic acids.

Other classes of BP compounds containing a hydroxyl group instead of an amino moiety were prepared from the corresponding carboxylic acids by treatment with a mixture of phosphorous acid and phosphorus trichloride, followed by quenching with water (Figure 20).128 It was found that using methansulfonic acid (MsOH) as a solvent improved the yield of the reaction and was preferred for large-scale preparation. G


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Figure 17. General methods for the synthesis of aminoalkylidendiphosphonic acids.

Figure 20. General methods for the synthesis of hydroxyalkylidenediphosphonic acids. Figure 18. Structures of new SIs containing BP groups.

produced in an almost quantitative yield on a 1 kg scale and tested successfully for its ability to collect metal cations from different sources, such as groundwater and mining process waters.132 Derivitization of the amine group using the Moedritizi−Irani reaction to increase the number of phosphonate groups was not carried out.

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PHOSPHONYLATION BY TETRAPHOSPHORUS HEXOXIDE (P4O6) It is well-known that phosphonic acids have widespread commercial acceptance for a variety of industrial applications as well as disease treatment. Therefore, there is great interest to find economical routes to prepare phosphonic acids in a high yield. Schülke et al. have reported for the first time the synthesis of a series of phosphonic acids by the reaction of P4O6 with

Figure 21. Structure of metal ion removal, including BP groups.

different electrophilic and nucleophilic compounds to afford inorganic and organic phosphorus compounds in high yields.133 Recently, Notte et al. have prepared a series of phosphonic acids in the presence of different homogeneous and/or heterogeneous Brönsted acid catalysts to provide a one-step

Figure 19. Synthesis of mono- and di(1,1-diphosphono-1-alkylaminomethyl)-4-hydroxybenzenesulfonic acids. H


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Figure 22. Synthesis of phosphonic acids using tetraphosphorus hexoxide (P4O6).

(Figure 24). The percentage of phosphorus monomer will vary between polymer strands in end-capped polymers because the

synthesis method capable of selectively delivering phosphonate compounds in high purity and high yield, as shown in Figure 22.134−138

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POLYPHOSPHONATES There are two main categories of commercial polyphosphonates: those with a polyamine backbone and those with a polyvinyl backbone. It was reported that the SIs with a polyamine backbone are phosphonated by the Moedritzer− Irani reaction to afford a molecular weight in the range of 300− 5000 (Figure 23).55 These classes of polymers are useful for

Figure 24. (Left) Vinylphosphonic acid (VPA) and (right) vinylbisphosphonic acid (VDPA).

polymerization is not fully controlled. This variation, in turn, will vary the strength of the chemisorption of the polymer strands onto a rock in a squeeze treatment. This then leads to selective desorption of the polymer strands, with the strands with the least phosphorus desorbing first, giving, over time, a false reading of the amount of polymer in the produced water if phosphorus detection is used alone to determine the polymer concentration. Nevertheless, several phosphorus end-capped polyvinyl scales are used commercially. VPA is one such monomer used in end-capped polyvinyl SIs. The VPA monomer is made in a two-step reaction. In the first step, ethyne (acetylene) is reacted with a dialkyl phosphonate ester to give a vinyl dialkyl phosphonate ester.151 VPA is then formed by hydrolysis of the ester in the presence of an acidic or a basic catalyst. However, the product of such a hydrolysis has been found to be substantially impure and contaminated with alcohols and other organics. A higher yield route is via hydrolysis of bis(β-haloalkyl) ester of VPA, preferably bis(βchloroethyl) ester in the presence of a ketone or an aldehyde.152 An alternate route is via high-temperature catalytic cleavage of dialkyl esters of 2-acetoxyethane phosphonic acid.153 Copolymers of VPA with unsaturated dicarboxylic anhydrides (ring opened in water to carboxylic acids) have been claimed as Ba/Sr SIs. Examples are VPA/isobutylene/ maleic anhydride copolymers hydrolyzed to give carboxylic acid groups.154

Figure 23. Synthesis of polyphosphonates with polyamine backbones.

sulfate scale inhibition particularly for squeeze applications.139−142 Unfortunately, this synthetic method is not efficient for polymers with backbones incorporating ester and/or amide groups because the acidic conditions lead to the hydrolysis of these functional groups. There are many vinylic compounds that contain phosphonate groups that can be used to make polyvinyl polymers.143−149 In general, these monomers are relatively expensive compared to say the common carboxylic or sulfonic acid monomers, such as (meth)acrylic, maleic, or vinylsulfonic acid. Therefore, some of them are used only as end-capping monomers to introduce some phosphorus into the polymer, often for ease of SI detection.150 Two examples are vinylphosphonic acid (VPA) and vinylbisphosphonic acid (VDPA) I


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trimethylsilane to give the calixarene tetraphosphonic acid, as shown in Figure 28.168−170

Another phosphorus-containing monomer is VDPA. This can be made by thermal removal of water from salts of αhydroxyalkane diphosphonic acid dimers (Figure 25).155 Several end-capped VDPA copolymers are commercial SIs.156−158

Figure 25. Synthesis of vinylbisphosphonic acid (VDPA).

Various acrylate, acrylamido, or styrene monomers with phosphonic acid groups have been used in polymers, sometimes in oilfield SIs but particularly for investigations into new dental materials. Some examples of these monomers are given in Figure 26.159−163 Low-molecular-weight poly(acrylic acid) with nitrilodi(methylenephosphonic acid) chain ends have been investigated as SIs.164

Figure 28. Tetraphosphonic acid derivatives of calixarenes.

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AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. ORCID

Mohamed F. Mady: 0000-0002-4636-0066 Malcolm A. Kelland: 0000-0003-2295-5804 Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS The authors gratefully acknowledge Total E&P Norge AS for financial support.

Figure 26. Vinylic monomers containing phosphonic acid groups.

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MISCELLANEOUS PHOSPHONATE SIS Phosphinopoly(carboxylic acid) (PPCA) also contains a phosphonic acid group, but in this case, the phosphorus atom is bonded to two carbon atoms (Figure 27). PPCA is a well-

REFERENCES

(1) Kelland, M. A. Production Chemicals for the Oil and Gas Industry, 2nd ed.; CRC Press (Taylor & Francis Group): Boca Raton, FL, 2014. (2) Frenier, W. W.; Ziauddin, M. Formation, Removal and Inhibition of Inorganic Scale in the Oilfield Environment; Society of Petroleum Engineers (SPE) Publishing: Richardson, TX, 2008. (3) Amjad, Z. The Science and Technology of Industrial Water Treatment; CRC Press (Taylor & Francis Group): Boca Raton, FL, 2010. (4) Sallis, J. D.; Juckes, W.; Anderson, M. E. In Mineral Scale Formation and Inhibition; Amjad, Z., Ed.; Plenum Press: New York, 1995. (5) Kelland, M. A. Energy Fuels 2006, 20, 825−847. (6) (a) Peabody, A. W. In Control of Pipeline Corrosion, 2nd ed.; Bianchetti, R. L., Ed.; NACE International: Houston, TX, 2001. (b) Craig, B. Oilfield Metallurgy and Corrosion, 3rd ed.; MetCorr (NACE): Houston, TX, 2004. (7) Uhlig, H. H.; Revie, R. W. Corrosion and Corrosion Control, 3rd ed.; Wiley-Interscience: New York, 1985. (8) (a) Chilingar, G. V.; Mourhatch, R.; Al-Qahtani, G. The Fundamentals of Corrosion and Scaling: A Handbook for Petroleum and Environmental Engineers; Gulf Publishing Company: Houston, TX, 2008. (b) Davies, M.; Scott, P. J. B. Oilfield Water Technology; National Association of Corrosion Engineers (NACE): Houston, TX, 2006. (9) Atkinson, G.; Mecik, M. J. Pet. Sci. Eng. 1997, 17, 113. (10) Amjad, Z. Mineral Scale Formation and Inhibition; Plenum Press: New York, 1995; pp 354. (11) Tomson, M. B.; Fu, G.; Watson, M. A.; Kan, A. T. SPE Prod. Facil. 2003, 18, 192. (12) Stewart, N. J.; Walker, P. A. M. U.S. Patent 6,527,983, 2003.

Figure 27. Phosphinopoly(carboxylic acid) (PPCA).

known oilfield SI.165−167 It differs from the phosphonate monomer end-capped SI polymers in containing only one phosphorus atom per polymer chain. These telomeric phosphinocarboxylic acids usually have a low molecular weight (200−1000 g/mol) and are made by reacting an unsaturated carboxylic acid, such as acrylic acid, with sodium hypophosphite. Calixarenes bearing phosphonic acid groups have been shown to induce the mesocrystal formation of barium sulfate, despite being relatively low-molecular-weight additives. These calixarenes are a synthesis in three steps from the parent calixarene by bromination of the aromatic rings, substitution with a phosphonodiester, and reaction of this with bromoJ


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