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Title: Polymer-supported sulfonated catechol and linear catechol amide ligands and their use in selective metal ion removal and recovery from aqueous solutions

Abstract

The present invention concerns the synthesis of several biomimetically important polymer-supported, sulfonated catechol (PS-CATS), sulfonated bis-catechol linear amide (PS-2-6-LICAMS) and sulfonated 3,3-linear tris-catechol amide (PS-3,3-LICAMS) ligands, which chemically bond to modified 6% crosslinked macroporous polystyrene-divinylbenzene beads (PS-DVB). These polymers are useful for the for selective removal and recovery of environmentally and economically important metal ions from aqueous solution, as a function of pH. The Fe.sup.3+ ion selectivity shown for PS-CATS, PS-2-6-LICAMS, and PS-3,3-LICAMS polymer beads in competition with a similar concentration of Cu.sup.2+, Zn.sup.2+, Mn.sup.2+, Ni.sup.2+,Mg.sup.2+, Al.sup.3+, and Cr.sup.3+ ions at pH 1-3. Further, the metal ion selectivity is changed at higher pH values in the absence of Fe.sup.3+ (for example, Hg.sup.2+ at pH 3). The rates of selective removal and recovery of the trivalent metal ions, e.g. Fe.sup.3+ Al.sup.3+ ion etc. with the PS-CATS, PS-2-6-LICAMS, and PS-3,3-LICAMS polymer beads use determined are useful as well as equilibrium selectivity coefficient (K.sub.m) values for all metal competition studies. The chelate effect for the predisposed octahedral PS-3,3-LICAMS polymer pendant ligand is the reason that this ligand has a more pronounced selectivity for Fe.sup.3+ ion in comparison to the PS-CATS polymer beads. The predisposed square planar PS-2-6-Mn.sup.2+, Ni.sup.2+, and Mg.sup.2+, than either PS-CATSmore » or PS-3,3-LICAMS. However, Fe.sup.3+ ion still dominates in competition with other divalent and trivalent metal ions. In the absence of Fe.sup.3+, the polymer ligand is selective for Al.sup.3+, Cu.sup.2+ or Hg.sup.2+. The changing of the cavity size from two CH.sub.2 groups to six CH.sub.2 groups in the PS-2-6-LICAMS polymer pendant ligand series does not effect the order of metal ion selectivity.

Inventors:
 [1]
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  1. Berkeley, CA
Issue Date:
Research Org.:
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
OSTI Identifier:
870910
Patent Number(s):
5622996
Assignee:
Regents of University of California (Oakland, CA)
Patent Classifications (CPCs):
C - CHEMISTRY C08 - ORGANIC MACROMOLECULAR COMPOUNDS C08F - MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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DOE Contract Number:  
AC03-76SF00098
Resource Type:
Patent
Country of Publication:
United States
Language:
English
Subject:
polymer-supported; sulfonated; catechol; linear; amide; ligands; selective; metal; removal; recovery; aqueous; solutions; concerns; synthesis; biomimetically; ps-cats; bis-catechol; ps-2-6-licams; 3-linear; tris-catechol; ps-3; 3-licams; chemically; bond; modified; crosslinked; macroporous; polystyrene-divinylbenzene; beads; ps-dvb; polymers; useful; environmentally; economically; solution; function; ph; selectivity; shown; polymer; competition; similar; concentration; cu; zn; mn; mg; 1-3; changed; values; absence; example; hg; rates; trivalent; etc; determined; equilibrium; coefficient; studies; chelate; effect; predisposed; octahedral; pendant; ligand; reason; pronounced; comparison; square; planar; ps-2-6-mn; dominates; divalent; changing; cavity; size; six; series; polymer beads; trivalent metal; aqueous solution; aqueous solutions; ph value; ph values; selective removal; square planar; chemically bond; selective metal; sulfonated catechol; polymer-supported sulfonated; similar concentration; catechol amide; amide ligands; linear catechol; /521/525/

Citation Formats

Fish, Richard H. Polymer-supported sulfonated catechol and linear catechol amide ligands and their use in selective metal ion removal and recovery from aqueous solutions. United States: N. p., 1997. Web.
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Fish, Richard H. Polymer-supported sulfonated catechol and linear catechol amide ligands and their use in selective metal ion removal and recovery from aqueous solutions. United States.
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Fish, Richard H. Wed . "Polymer-supported sulfonated catechol and linear catechol amide ligands and their use in selective metal ion removal and recovery from aqueous solutions". United States. https://www.osti.gov/servlets/purl/870910.
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@article{osti_870910,
title = {Polymer-supported sulfonated catechol and linear catechol amide ligands and their use in selective metal ion removal and recovery from aqueous solutions},
author = {Fish, Richard H},
abstractNote = {The present invention concerns the synthesis of several biomimetically important polymer-supported, sulfonated catechol (PS-CATS), sulfonated bis-catechol linear amide (PS-2-6-LICAMS) and sulfonated 3,3-linear tris-catechol amide (PS-3,3-LICAMS) ligands, which chemically bond to modified 6% crosslinked macroporous polystyrene-divinylbenzene beads (PS-DVB). These polymers are useful for the for selective removal and recovery of environmentally and economically important metal ions from aqueous solution, as a function of pH. The Fe.sup.3+ ion selectivity shown for PS-CATS, PS-2-6-LICAMS, and PS-3,3-LICAMS polymer beads in competition with a similar concentration of Cu.sup.2+, Zn.sup.2+, Mn.sup.2+, Ni.sup.2+,Mg.sup.2+, Al.sup.3+, and Cr.sup.3+ ions at pH 1-3. Further, the metal ion selectivity is changed at higher pH values in the absence of Fe.sup.3+ (for example, Hg.sup.2+ at pH 3). The rates of selective removal and recovery of the trivalent metal ions, e.g. Fe.sup.3+ Al.sup.3+ ion etc. with the PS-CATS, PS-2-6-LICAMS, and PS-3,3-LICAMS polymer beads use determined are useful as well as equilibrium selectivity coefficient (K.sub.m) values for all metal competition studies. The chelate effect for the predisposed octahedral PS-3,3-LICAMS polymer pendant ligand is the reason that this ligand has a more pronounced selectivity for Fe.sup.3+ ion in comparison to the PS-CATS polymer beads. The predisposed square planar PS-2-6-Mn.sup.2+, Ni.sup.2+, and Mg.sup.2+, than either PS-CATS or PS-3,3-LICAMS. However, Fe.sup.3+ ion still dominates in competition with other divalent and trivalent metal ions. In the absence of Fe.sup.3+, the polymer ligand is selective for Al.sup.3+, Cu.sup.2+ or Hg.sup.2+. The changing of the cavity size from two CH.sub.2 groups to six CH.sub.2 groups in the PS-2-6-LICAMS polymer pendant ligand series does not effect the order of metal ion selectivity.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {1997},
month = {1}
}
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Works referenced in this record:

Structural and spectroscopic characterization of chiral ferric tris-catecholamides: unraveling the design of enterobactin
journal, February 1992

Rational reduction of the conformational space of a siderophore analog through nonbonded interactions: the role of entropy in enterobactin
journal, July 1993

Modern Research in Ion Exchange
book, January 1986

Abtrennung von Schwermetallionen mit Polystyrolaustauschern
journal, January 1980

Synthese von chelatbildenden ionenaustauschern auf der basis von Polystyrol
journal, October 1980

The Chemistry of Transition Metal Complexes Containing Catechol and Semiquinone Ligands
book, January 1994

Biomimetic metal encapsulation
journal, November 1990

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