Novel metal chelating chitosan derivative: attachment of iminodiacetate moieties via a hydrophilic spacer group

Abstract

. Can. J. Chem. 69, 585 (1991).Chitosan has been reductively N-alkylated with a 6-0-substituted galactose derivative bearing an iminodiacetate residue, to give a chitosan derivative having a hydrophilic branch and a metal chelating group. The Cu(I1) binding capacity of the derivative was comparable to native chitosan, but showed better ion-exchange ability. The product was water soluble, giving viscous 1% aqueous solutions that showed decreased viscosity upon addition of Cu(I1) ions.Key words: chitosan, derivative, chelation, solubilization, viscosity.KEVIN R. HOLME et LAURANCE D. HALL. Can. J. Chem. 69,585 (1991).Dans le but d'obtenir un dtrivC du chitosane portant une portion hydrophile et un groupement chtlatant, on a proctdt a une rtduction N-alkylante du chitosane avec un dtrivt 6-0-substitut du galactose portant une portion iminodiacttate. La capacitt de chtlation du Cu(I1) de ce dtrivC est semblable a celle du chitosane naturel; toutefois, il prtsente une meilleure habilitt l'tchange ionique. Le produit est soluble dans l'eau et les solutions aqueuses a 1% sont visqueuses; ce rtsultat dtmontre que la viscositt diminue par addition d'ions Cu(I1).

A Pyrazole‐Expanded EDTA Ligand and its Pentanuclear Iron(III) Complex

“…For the synthesis of target ligand H 5 L we initially followed a strategy developed earlier for other pyrazole‐based ligands (Scheme , left branch) 6,7. It starts from the tetrahydropyranyl(thp)‐protected pyrazole building block I ,6c which in this case was reacted with iminodiacetic acid (protected as the methyl ester)8 to attach the side arms. However, this reaction did not reach full conversion under usual conditions, and hence some modifications were necessary for the present system.…”

“…Materials: Potassium iodide, sodium thiosulfate, sodium sulfate, sodium carbonate, and potassium hydroxide (all Grüssing) as well as perchloric acid (Merck) and all solvents were used as purchased. 3, 5‐Bis(chloromethyl)‐1‐(tetrahydropyran‐2‐yl)‐1 H ‐pyrazole6c and dimethyl iminodiacetate (as the hydrochloride)8 were synthesized with slight modifications according to the described procedures.…”

“…Synthesis of III: dimethyl iminodiacetate hydrochloride8 (5.14 g, 26.0 mmol), II (5.63 g, 13.0 mmol), and water free Na 2 CO 3 (13.0 g, 122.7 mmol) were suspended in acetonitrile (100 mL). The resulting yellow suspension was stirred for two days at room temperature under exclusion of light.…”

Interaction of Ag(I), Hg(II), and Cu(II) with 1,2-ethanedithiol immobilized on chitosan: Thermochemical data from isothermal calorimetry

“…To increase the adsorption capacity, various chemically modified chitosans have been prepared [23][24][25][26][27][28][29]. Based on the success of employing Schiff reactions, we introduce an aldehyde that could couple the ligand 1,2-ethanedithiol (QTDT) to the surface of chitosan, yielding a QTDT material.…”

Synthesis of carboxylated chitosan and its adsorption properties for cadmium (II), lead (II) and copper (II) from aqueous solutions

“…A number of reviews deal with chemical modifications of chitosan and its applications (Kurita 2001;Harish Prashanth & Tharanathan 2007;Mourya & Inamdar 2008). The grafting of carboxylic functions has frequently been regarded as an interesting process for increasing the sorption properties of chitosan (Lopez-de-Alba et al 1987;Holme & Hall 1991). The adsorption properties of N-carboxyalkyl or O-carboxyalkyl chitosan derivatives already have a large number of reports (Delben & Muzzarelli 1989;Wan Ngah & Liang 1998;Hon & Tang 2000;Lee et al 2005;Sun et al 2007).…”