Retention behavior of hydroxybenzene derivatives on polymer resin immobilized with macrocyclic polyamines

Takashi Mukuno, Koji Takahashi, Toshihiko Imato

Research output: Contribution to journalArticle

Abstract

Four kinds of macrocyclic polyamine (MCPA)-immobilized polymer resins were prepared by reacting macroreticular-type chloromethylated polystyrene (CPS) with [9]aneN3, [14]aneN4, [15]aneN5 and [18]aneN6. The retention times of the solutes (dihydroxybenzene, hydroxybenzoic acid and dihydroxybenzoic acid isomers) were measured for a column packed with the MCPA-immobilized polymer resin by using a liquid-chromatographic method. Phosphate buffer solutions of pH 1.8, 4.5 and 6.8 were used as eluents. The distribution coefficients of the solutes on the MCPA-immobilized polymer resin were calculated from the capacity factors obtained by the retention time and volume of the resin and liquid phases in the column. Linear polyamines, such as diethvlenetriamine and triethylenetetramine, were immobilized on lhe polymer resin, and the distribution coefficients of the solutes on these resins were measured as well as the unmodified resin for a comparison with the MCPA-immobilized polymer resin. The MCPA-immobilized polymer resins showed higher adsorptivity for the solutes than did the linear polyamine-immobilized polymer resin. Especially, the [15]aneN5-immobilized polymer resin showed selective adsorptivity for the isomers of dihydroxybenzene among the MCPA-immobilized polymer resin. The distribution coefficients of the MCPA-immobilized polymer resin for hydroxybenzene isomers increased in the order para < meta < ortho isomer. The same sequence was observed for the isomers of hydroxybenzoic acid when phosphate buffer solutions of pH 1.8 and 4.5 were used as eluents. For dihydroxybenzoic acid isomers, the distribution coefficients of the MCPA-immobilized polymer resin increased in the order 3,5- = 3,4- < 2,5- isomers. The hydrogen-bonding interaction between the MCPA-immobilized resin and the solutes is estimated to be more effective than the electrostatic interaction for the distribution of the solutes on the MCPA-immobilized resin.

Original languageEnglish
Pages (from-to)1111-1115
Number of pages5
Journalbunseki kagaku
Volume47
Issue number12
DOIs
Publication statusPublished - Dec 1998

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All Science Journal Classification (ASJC) codes

  • Analytical Chemistry

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