Extraction of alkaline earth cations from aqueous solutions by crown ether carboxylic acids

Strzelbicki, Jerzy; Bartsch, Richard A.

doi:10.1021/ac00237a026

Cited by 59 publications

(28 citation statements)

References 3 publications

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“…The Na + ion, with a size of 2.2 A, 27 can fit into the cavity (2.0-2.4 A) of DB16C5 very well, and therefore the Na + -crown ether complex may be stronger than that of other alkali metal ions. 28 The frequency shift sequence for alkali earth metal ions by the C60-crown ether-coated PZ detector is Ba > Ca > Sr 2+ > Mg 2+ , as shown in Fig. 6.…”

Section: Resultsmentioning

confidence: 97%

Fullerene‐Crown Ether Coated Piezoelectric Crystal Liquid Chromatographic Detector for Metal Ions and Polar/Nonpolar Organic Molecules

Hung¹,

Shih²

2000

J Chinese Chemical Soc

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Fullerene(C60)-dibenzo-16-crown-5-oxyacetic acid (DBI6C5-OCH2-COOC60) was prepared and applied as the coating material on piezoelectric quartz crystals for detection of various metal ions and polar/nonpolar organic molecules. The C60-crown ether-coated piezoelectric crystal sensor with a home-made computer inter face for signal acquisition and data processing was applied as an ion Chromatographie (IC) detector for various metal ions, e.g., alkali metal, alkaline earth metal and transition-metal ions. The piezoelectric detector exhib ited quite good sensitivity of 10 4 ~ 10 6 Hz/M and good detection limit of 10" 3 ~ 10" 4 M for these metal ions. The C60-crown ether piezoelectric detector compared well with the commercial conductivity detector convention ally used for metal ions. The ionic size and ionic charge seemed to have significant effect on the frequency re sponse of the piezoelectric detector. The C60-crown ether coated piezoelectric crystal sensor was also em ployed as a high performance liquid Chromatographie (HPLC) detector for various polar organic molecules with frequency responses in the order: amines > carboxylic acids > alcohols > ketones. Furthermore, nonpolar organic molecules, e.g., n-hexane, 1-hexene and 1-hexyne, were also detected with this piezoelectric crystal de tector. The frequency responses of the piezoelectric crystal detector for these nonpolar organic molecules were in the following order: alkynes » alkenes > alkanes. The effects of solvents and flow rate on the frequency re sponses of the piezoelectric crystal detector were investigated. The C60-crown ether coated piezoelectric crys tal detector also showed short response time (< 1 min.) and good reproducibility.

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Section: Resultsmentioning

confidence: 97%

Fullerene‐Crown Ether Coated Piezoelectric Crystal Liquid Chromatographic Detector for Metal Ions and Polar/Nonpolar Organic Molecules

Hung¹,

Shih²

2000

J Chinese Chemical Soc

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“…This stoichiometry is anticipated also from electroneutrality of the complexes transferred into chloroform phase, taking into account that transfer of strongly hydrated C1-and OH-anions into the low polar organic phase has low probability (5).…”

Section: Extraction From a 000167 M Solution Of Divalent Metal Chlormentioning

confidence: 97%

“…Synthesis of n-dodecyloligo(oxyethy1ene) carboxylic acids [1][2][3][4][5][6] Xylene (500 mL) was heated over 1 mol (23 g) of metallic sodium until the mixture came to a boil. Thereafter, the mixture was slowly heated while being stirred vigorously and a white-grey suspension of sodium was obtained.…”

Section: Reagentsmentioning

confidence: 99%

Extraction of Zn(II), Cd(II), and Hg(II) by dodecyloligo(oxyethylene) carboxylic acids

Strzelbicki¹,

Charewicz²,

Beger³

et al. 1988

Can. J. Chem.

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. Can. J. Chem. 66, 1695 (1988). The synthesis of a series of n-dodecyloligo(oxyethylene) carboxylic acids of general formula ClzH25(OCH2CH2)nOCH2COOH (n = 0 to 5) and application of these compounds for the separation of Zn(lI), Cd(II), and Hg(I1) in extraction are reported. Negligible extractability of the metal ions investigated was found usingdodecyloxyacetic acid (n = 0) which indicated that complexation resulted from metal-cation interaction with oxygen atoms of the polyoxyethylene chain incorporated into the molecule of complexon. In extractions from aqueous solutions containing ZnCl,, CdCI2, HgC12, and NaOH (pH regulator), loading of the organic phases increased for extractants with more oxyethylene units. In particular, Hg(I1) extractability and molecular structure of the extractant are related. The selectivity of extraction increased drastically if NaCl was added to the initial aqueous phase, as the extractabilities of Cd(I1) and, particularly, Hg(1I) declined while the extractability of Zn(I1) remained high. Selectivity of extraction is produced by the complex chemical equilibria resulted from complexation of the metal cation by an alkyloligoether carboxylic acid in the organic phase and by C1-and OH-anions in the aqueous phase. Thus, aqueous solution parameters greatly influence the efficiency and the selectivity of the extraction process and suitable experimental conditions are very important.JERZY STRZELBICKI, WITOLD CHAREWICZ, JORG BEGER, et LUTZ HINZ. Can. J. Chem. 66, 1695 (1988). On a rCalisC la synthttse d'une sCrie d'acides n-dodCcyloligo(oxyCthyl~ne)carboxyliques de formule gCnCrale ClzH25(OCH2CH2),OCH2C0OH (n = 0 a 5) et on a examink I'utilitC de ces composCs pour sCparer et extraire les ions Zn(II), Cd(l1) et Hg(I1). La quantitC d'ions mktalliques extraite par I'acide dodCcyloxyacCtique (n = 0) est nkgligeable; ce rCsultat indique que la complexation est diie aux interactions des ions mktalliques avec les atomes d'oxyghe de la chaine polyoxyCthylttne incorporCe dans la molCcule complexante. Lors d'extractions effectuCes a partir de solutions aqueuses contenant du ZnC12, du CdC12, du HgC12 et du NaOH (pour rCgulariser le pH), les molCcules complexantes contenant le plus grand nombre dlunitCs oxymCthyl6nes provoquent une augmentation de la concentration des ions extraits dans les phases organiques; on a pu mettre en Cvidence une relation entre la facilitC d'extraction du Hg(I1) et la structure molCculaire des molCcules complexantes. La sClectivitC des extractions augmente d'une f a~o n drastique lorsqu'on ajoute du NaCl h la phase aqueuse initiale; dans ces conditions, la facilitC d'extraction du Cd(I1) et, en particulier, celle du Hg(I1) diminuent alors que celle du Zn(I1) demeure ClevCe. La sClectivitC des extractions est le reflet d'Cquilibres chimiques complexes qui proviennent de la complexation des cations mitalliques par un acide alkyloligoCther carboxylique dans la phase organique et par les anions C1-et OH-dans la phase aqueuse. Ainsi, les paramtttres de la solution aqueuse influence...

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“…Attachment of a lipophilic alkyl group was found to reduce loss of ionized sym-dibenzo-16-crown-5-oxyacetic acid from a chloroform solution into a contacting aqueous solution during competitive solvent extraction of alkali metal cations [5]. (Tables 2-4) with an alkyl, branched alkyl, cycloalkyl, fluoroalkyl, aryl, aralkyl, alkenyl and alkynyl group attached to the polyether ring carbon geminal to an oxyacetic acid side arm were prepared by reaction of the corresponding lariat ether alcohol with sodium or potassium hydride in tetrahydrofuran followed by addition of bromoacetic acid.…”

Section: Synthesis Of Sym-(r)dibenzo-16-crown-5-oxyacetic Acidsmentioning

confidence: 99%

“…For several years, we have been involved in the design and preparation of lariat ether carboxylic acids and the study of their behavior in metal ion separation processes [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20]. These ligands have been found to be effective chelating agents for alkali and alkaline earth metal cations and trivalent lanthanide ions .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of lariat ether carboxylic acids based on dibenzo‐16‐crown‐5

Bartsch

Cowey

Elshani

et al. 2001

Journal of Heterocyclic Chem

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Synthetic routes to forty‐seven dibenzo‐16‐crown‐5 compounds with pendant carboxylic acid groups are reported. When taken together with previously described lariat ether carboxylic acids, these new compounds provide several series with systematic structural variations including changes in the identity and attachment site(s) of one or more lipophilic groups and the length of the spacer that connects the carboxylic acid group to the polyether framework.

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Extraction of alkaline earth cations from aqueous solutions by crown ether carboxylic acids

Cited by 59 publications

References 3 publications

Fullerene‐Crown Ether Coated Piezoelectric Crystal Liquid Chromatographic Detector for Metal Ions and Polar/Nonpolar Organic Molecules

Fullerene‐Crown Ether Coated Piezoelectric Crystal Liquid Chromatographic Detector for Metal Ions and Polar/Nonpolar Organic Molecules

Extraction of Zn(II), Cd(II), and Hg(II) by dodecyloligo(oxyethylene) carboxylic acids

Synthesis of lariat ether carboxylic acids based on dibenzo‐16‐crown‐5

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