Abstract
Three p-phenylenediamine antioxidants (p-phenylenediamine-N,N,N′,N′-tetrapropionic acid tetramethyl ester, p-phenylenediamine-N,N,N′-tripropionic acid trimethyl ester, and p-phenylenediamine-N, N′-dipropionic acid dimethyl ester) were successfully synthesized via atom-economic aza-Michael addition of pphenylenediamine to methyl acrylate p-romoted by graphene oxide in water. The synthesized compounds were characterized by NMR, ESI-MS spectra, and elemental analyses. The effects of the solvent and graphene oxide on the reaction were investigated.
Similar content being viewed by others
References
Reingruber, E. and Buchberger, W., J. SeP.Sci., 2010, vol. 33, p. 3463.
Narathichat, M., Sahakaro, K., and Nakason, C., J. Appl. Polym. Sci., 2010, vol. 115, p. 1702.
Xiao, F., Zhou, Y., and Yang, W., Russ. J. Gen. Chem., 2014, vol. 84, p. 2218.
Klein, E., Cibulková, Z., and Lukeš, V., Polym. Degrad. Stab., 2005, vol. 88, p. 548.
Rapta, P., Vargova, A., Polovkova, J., Gatial, A., Omelka, L., Majzlik, P., and Breza, M., Polym. Degrad. Stab., 2009, vol. 94, p. 1457.
You, B., Zhou, D., Yang, F., and Ren, X.-C., Colloids Surf. A, 2011, vol. 392, p. 365.
Abdelwahab, N.A., El-Nashar, D.E., and El-Ghaffar, M.A., Mater. Des., 2011, vol. 32, p. 238.
Singh, R.P., Vishwa Prasad, A., and Pandey, J.K., Macromol. Chem. Phys., 2001, vol. 202, p. 672.
Gryn’ova, G., Ingold, K.U., and Coote, M.L., J. Am. Chem. Soc., 2012, vol. 134, p. 12979.
Cibulková, Z., Černá, A., Šimon, p., Uhlár, J., Kosár, K., and Lehocký, P., J. Therm. Anal. Calorim., 2012, vol. 108, p. 415.
Wang, X.-F., Wang, B.-B., Song, L., Wen, P.-Y., Tang, G., and Hu, Y., Polym. Degrad. Stab., 2013, vol. 98, p. 1945.
Cibulková, Z., Šimon, p., Lehocký, P., Kosár, K., and Chochulová, A., J. Therm. Anal. Calorim., 2009, vol. 97, p. 535.
Cibulková, Z., Šimon, P., Lehocký, P., and Balko, J., J. Therm. Anal. Calorim., 2005, vol. 80, p. 357.
Cataldo, F., Polym. Degrad. Stab., 2001, vol. 72, p. 287.
Polshettiwar, V. and Varma, R.S., Tetrahedron, 2010, vol. 66, p. 1091.
Mungse, H.P. and Khatri, O.P., J. Phys. Chem. C, 2014, vol. 118, p. 14394.
Zhang, F., Jiang, H., Wu, X., Mao, Z., and Li. H., ACS Appl. Mater. Interfaces, 2015, vol. 7, p. 1669.
Su, C.-L., and Loh, K.-P., Acc. Chem. Res., 2013, vol. 46, p. 2275.
Dreyer, D.R., Todd, A.D., and Bielawski, C.W., Chem. Soc. Rev., 2014, vol. 43, p. 5288.
Verma, S., Mungse, H.P., Kumar, N., Choudhary, S., Jain, S.L., Sain, B., and Khatri, O.P., Chem. Commun., 2011, vol. 47, p. 12673.
Author information
Authors and Affiliations
Corresponding author
Additional information
The text was submitted by the authors in English.
Rights and permissions
About this article
Cite this article
Li, YT., Zhang, QP., Xiao, F. et al. Graphene oxide promoted synthesis of p-phenylenediamine antioxidants. Russ J Gen Chem 86, 356–359 (2016). https://doi.org/10.1134/S1070363216020262
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363216020262