Synthesis and preliminary evaluation of chelating resins containing α-aminoalkylphosphonic groups

Ménard, Laurent; Fontaine, Laurent; Brosse, Jean‐Claude

doi:10.1016/0923-1137(94)90022-1

Cited by 15 publications

(3 citation statements)

References 20 publications

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“…Resins containing phosphonic groups have been synthesized and reported in the literature , and used for ecotoxic metals recovery. Resins with α-aminoalkylphosphonic groups have been synthesized as well by the addition of diethylphosphonate followed by hydrolysis , or by adding phosphorous acid on the corresponding polyimines. They have been used for the preliminary evaluation of the sorption capacity toward the Ca 2+ and Co 2+ ions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Phosphonate Ester/Phosphonic Acid Grafted Styrene−Divinylbenzene Copolymer Microbeads and Their Utility in Adsorption of Divalent Metal Ions in Aqueous Solutions

Popa

Davidescu

Negrea

et al. 2008

Ind. Eng. Chem. Res.

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In this paper the preparation and characterization of some chelating resins, phosphonate grafted on polystyrene−divinylbenzene supports, are reported. The resins were prepared by an Arbuzov-type reaction between chloromethyl polystyrene−divinylbenzene copolymers and triethylphosphite, yielding the phosphonate ester copolymer (resin A). This can be hydrolyzed by HCl to yield the phosphonate/phosphonic acid copolymer (resin B). The phosphonate resins A and B were characterized by determination of the phosphorus content, infrared spectrometry, and thermal analysis. The total sorption capacity of the phosphonate ester functionalized resin (A) and phosphonate/phosphonic acid functionalized resin (B) for divalent metal ions such as Ca2+, Cu2+, and Ni2+ was studied in aqueous solutions. Resin A retains ∼3.25 mg of Ca2+/g of copolymer and 2.75 mg of Cu2+/g of copolymer, but retains no Ni2+ at pH 1. On the other hand, resin B retains 8.46 mg of Ca2+/g of copolymer, 7.17 mg of Cu2+/g of copolymer, and no Ni2+ at pH 1. Efficient Ni2+ retention was observed at pH 7 only for the phosphonate/phosphonic acid functionalized resin (B) at the level of 19 mg of Ni2+/g of polymer B. Polymer A was incapable of retaining Ni2+ at pH 7.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Phosphonate Ester/Phosphonic Acid Grafted Styrene−Divinylbenzene Copolymer Microbeads and Their Utility in Adsorption of Divalent Metal Ions in Aqueous Solutions

Popa

Davidescu

Negrea

et al. 2008

Ind. Eng. Chem. Res.

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“…Among the mimics of natural bioactive molecules, α-amino phosphonates are important owing to their vast applications in biochemistry. , As a result of continuous efforts in this area, utilization of α-amino phosphonates are expanding into many new channels. , Among all the biological applications of α-amino phosphonates, more importantly it exhibits wide range of potential activities against cancer, − tuberculosis, , HIV , and bacterial agents, etc. − Amino phosphonates have been used as mimics of peptides, enzyme inhibitors and also as therapeutic agents for many diseases. − Apart from biological applications of amino phosphonates, α-amino phosphonates are serving as synthons for the construction of many new chemical entities. − Amino phosphonates facilitate simple methods for the synthesis of highly functionalized indoles, isocoumarins and many other heterocycles. − …”

Section: Introductionmentioning

confidence: 99%

A Green Approach to the Synthesis of α-Amino Phosphonate in Water Medium: Carbene Insertion into the N–H Bond by Cu(I) Catalyst

2016

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Synthesis of amino phosphonates is more important owing to their significant applications in the biological systems. There are few methods already known in the literature to make these molecules; however, known methods have their own disadvantages. In this regard, synthesis of different kinds of amino phosphonates have been achieved via phosphonate substituted carbene insertion into the N-H bond of aniline catalyzed by readily available copper salt under mild reaction conditions in water. In order to find an efficient catalyst for carbene insertion reaction in neat water, a large number of transition metal catalysts were screened, and we found that the [Cu(CHCN)]ClO was the best catalyst under employed reaction conditions. Using this environmentally benign methodology (copper catalyzed reaction in water), a large number of biologically important amino phosphonates have been synthesized, isolated (37 examples), and characterized using standard analytical and spectroscopic techniques.

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“…In order to study the influence of the furan substitution pattern, we first synthesized dimethylphosphonate-terminated furan-functionalized PEO monomethyl ethers 5a-c and their phosphonic acid-terminated homologues 6a-b according to our reported procedure (Scheme 2) 22,23 combining the click CuAAC 3 and the Kabachnik-Fields [24][25][26][27] reaction that is rarely utilized in polymer chemistry. 23,[28][29][30][31][32] Next we looked into the role of the furan substitution position onto the DA/rDA reactivity of the prepared furan-functionalized phosphonated PEOs by using N-methylmaleimide as a model dienophile.…”

Section: Introductionmentioning

confidence: 99%

Phosphonated furan-functionalized poly(ethylene oxide)s using orthogonal click chemistries: synthesis and Diels–Alder reactivity

et al. 2015

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The synthesis and the reactivity in Diels-Alder and retro Diels-Alder (DA/rDA) reactions of a series of novel phosphonated furan-functionalized PEO monomethyl ethers were investigated. Dimethylphosphonate-terminated furan-functionalized PEO monomethyl ethers and their phosphonic acid-terminated derivatives have been successfully prepared by using a combination of click copper-catalyzed 1,3dipolar cycloaddition and Kabachnik-Fields reactions. Influence of both the substitution pattern of the furan ring and the solvent onto the DA/rDA process were investigated. It was found that the 3-substituted furan is the more reactive and that water facilitates both the DA and the rDA reactions, while maintaining the polymeric structure intact. The results demonstrate the potential of such structures for dynamic covalent applications and controlled drug delivery systems such as thermoreversible linkage of biological entities onto metallic nanoparticles.Scheme 1 The concept of magnetically stimulated rDA reaction using IONPs. † Electronic supplementary information (ESI) available: Detailed experimental procedures and NMR spectra. See a Determined by 1 H NMR spectroscopy by comparing the peak areas of the CH-O groups of oxanorbornene at δ = 5.13-5.39 ppm and the methylene protons of the PEO in α of the triazole ring at δ = 4.52 ppm. PaperPolymer ChemistryPolym. Chem. This journal is

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Synthesis and preliminary evaluation of chelating resins containing α-aminoalkylphosphonic groups

Cited by 15 publications

References 20 publications

Synthesis and Characterization of Phosphonate Ester/Phosphonic Acid Grafted Styrene−Divinylbenzene Copolymer Microbeads and Their Utility in Adsorption of Divalent Metal Ions in Aqueous Solutions

Synthesis and Characterization of Phosphonate Ester/Phosphonic Acid Grafted Styrene−Divinylbenzene Copolymer Microbeads and Their Utility in Adsorption of Divalent Metal Ions in Aqueous Solutions

A Green Approach to the Synthesis of α-Amino Phosphonate in Water Medium: Carbene Insertion into the N–H Bond by Cu(I) Catalyst

Phosphonated furan-functionalized poly(ethylene oxide)s using orthogonal click chemistries: synthesis and Diels–Alder reactivity

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