Synthesis and characterization of diethyl-p-vinylbenzyl phosphonate monomer: precursor of ion exchange polymers for fuel cells

 

M. Ocampo-Fernández¹, Ana M. Herrera², T. Méndez-Bautista², J. García-Serrano^2*

 

¹ Posgrado en Ciencia de Materiales, Universidad Autónoma del Estado de Hidalgo Carretera Pachuca-Tulancingo Km. 4.5, 42184, Mineral de la Reforma, Hgo., México.

² Centro de Investigaciones en Materiales y Metalurgia, Universidad Autónoma del Estado de Hidalgo Carretera Pachuca-Tulancingo Km. 4.5, 42184, Mineral de la Reforma, Hgo., México. *jserrano@uaeh.edu.mx

 

Recibido: 18 de mayo de 2009.
Aceptado: 9 de junio de 2009.

 

Abstract

Synthesis of diethyl-p-vynilbenzyl phosphonate (DEpVBP) monomer and its homopolymer, precursors of ion exchange materials, are reported. DEpVBP monomer was synthesized by means of Michaelis-Arbusov reaction of p-vinylbenzyl chloride with tryethyl phosphite in the presence of cupric chloride using chlorebenzene as solvent with a yield of 75%. Homopolymer was synthesized by free radical polymerization reaction using AIBN as a free radical initiator at 70 ºC in DMF. The structures of the compounds were determined from NMR, FT-IR and Raman spectroscopy. Good thermal stability of homopolymer (up to 200 ºC) indicates that theses compounds are excellent candidates to be used in the development of new proton exchange membranes for fuel cells.

Keywords: Ion exchange polymers; Phosphonated polymers; Metallorganic compounds.

 

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Acknowledgments

M. Ocampo-Fernandez acknowledges to CONACyT, Mexico for the graduate fellowship. The work was partially supported by PROMEP, Mexico.

 

References

[1]. Itoh T.; Hamaguchi Y.; Uno, T.; Kubo, M.; Aihara, Y.; Sonai, A. Solid State Ionics, 177, 185 (2006).         [ Links ]

[2]. Linkous, C. A.; Anderson, H.R.; Kopitzke, R.W.; Nelson, G.L. Int. J. Hydrogen Energy, 23, 525 (1998).         [ Links ]

[3]. Madden, T. H.; Stuve, E. M.; J. Electrochem. Soc., 150, E571 (2003).         [ Links ]

[4]. Bryant, D. E.; Kilner, A. J. Mol. Catal. A: Chem., 193, 83 (2003).         [ Links ]

[5]. García-Serrano, J.; Pal, U.; Herrera, Ana M.; Salas, P.; Angeles-Chavez, C. Chem. Mater. 20, 5146 (2008).         [ Links ]

[6]. Gudrun Schmidt-Naake, Chem. Eng. Technol, 28, (2005).         [ Links ]

[7]. Donald J. Burton, Journal of Fluorine Chemistry, 82, 13 (1997).         [ Links ]

[8]. Parvole, J. Macromolecules, 41, 3893 (2008).         [ Links ]

[9]. Kotov, S.; Burton, D. J. Fluorine Chem. 82, 13 (1997).         [ Links ]

[10]. Jakoby, K.; Nunes, S. P. Macromol.Chem.Phys., 204, 61 (2003).         [ Links ]

[11]. Bhattacharya, A.; Thyagarajan, G. Chem. Rev. 81, 415 (1981).         [ Links ]

[12]. Cabasso, I.; Yu, Z. J. Polym. Sci. Part A 28, 227 (1990).         [ Links ]

[13]. Tamber, H.;Smid J.; Cabasso I. Chem. Mater 9, 1335 (1997).         [ Links ]

[14]. Nakanishi, K. Infrared absorption spectroscopy (Holden- Day, San Francisco, 1962).         [ Links ]

[15]. Danilich, M.J.; Burton, D.J.; Marchant, R.E. Vib. Spectroscopy 9, 229 (1995).         [ Links ]

[16]. Popa, A., Davidescu, C.M.; Negrea, P.; Ilia, G.; Katsaros, A.; Demadis, K.D. Ind. Eng. Chem. Res. 47, 2010 (2008).         [ Links ]

[17]. Yamabe, M.; Akiyama, K.; Akatsuka, Y.; Kato, M. European Polymer Journal 36, 1035 (2000).         [ Links ]