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Determination of the Acid-Base Dissociation Constant of Acid-Degradable Hexamethylenetetramine by Capillary Zone Electrophoresis

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Abstract

The acid-base equilibrium of hexamethylenetetramine (hexamine) was analyzed with its effective electrophoretic mobility by capillary zone electrophoresis. Although hexamine is degradable in a weakly acidic aqueous solution, and the degraded products of ammonia and formaldehyde can be formed, the effective electrophoretic mobility of hexamine was measured in the pH range between 2.8 and 6.9. An acid-base dissociation equilibrium of the protonated hexamine was analyzed based on the mobility change, and an acid dissociation constant of pKa = 4.93 ± 0.01 (mean ± standard error, ionic strength: 0.020 mol dm−3) was determined. The monoprotic acid-base equilibrium of hexamine was confirmed through comparisons of its electrophoretic mobility with the N-ethylquinolinium ion and with the monocationic N-ethyl derivative of hexamine, as well as a slope analysis of the dissociation equilibrium.

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Acknowledgments

This study was supported in part by the Grant-in-Aid for Scientific Research Program (KAKENHI) of the Japan Society for the Promotion of Science (JSPS), Grant Number 26410154. The authors are grateful to Dr. Fujinaga (Tokushima University) and Dr. Ueta (Tokushima University) for the LC-MS measurements.

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Authors and Affiliations

  1. Graduate School of Science and Technology, Tokushima University, 2-1 Minamijyousanjima-cho, Tokushima, 770-8506, Japan

    Toshio Takayanagi, Masashi Kurashina & Hitoshi Mizuguchi

  2. Graduate School of Advanced Technology and Science, Tokushima University, 2-1 Minamijyousanjima-cho, Tokushima, 770-8506, Japan

    Natsumi Shimakami

  3. Paper Industry Innovation Center, Ehime University, 127 Mendori-cho, Shikokuchuo, Ehime, 799-0113, Japan

    Tomoki Yabutani

Authors
  1. Toshio Takayanagi
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  2. Natsumi Shimakami
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  3. Masashi Kurashina
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  4. Hitoshi Mizuguchi
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  5. Tomoki Yabutani
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Takayanagi, T., Shimakami, N., Kurashina, M. et al. Determination of the Acid-Base Dissociation Constant of Acid-Degradable Hexamethylenetetramine by Capillary Zone Electrophoresis. ANAL. SCI. 32, 1327–1332 (2016). https://doi.org/10.2116/analsci.32.1327

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  • DOI: https://doi.org/10.2116/analsci.32.1327

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