Copyright (c) 2017 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization and Radical Polymerization of Novel Furan Substituted Acrylamide
Corresponding Author(s) : Mustafa Tombul
Asian Journal of Chemistry,
Vol. 29 No. 2 (2017): Vol 29 Issue 2
Abstract
N-[(Furan-2-yl)methyl]acrylamide (FMA) was synthesized via the reaction of furfurylamine with acryloyl chloride and the chemical structure was elucidated by 1H NMR, 13C NMR and FTIR analyses. Free radical polymerization of N-[(furan-2-yl)methyl]acrylamide was performed employing benzoyl peroxide (BPO) initiator under inert atmosphere of nitrogen in toluene. The monomer concentration and initiator concentration ranges were 8.8 × 10-2 to 13.2 × 10-2 mol L-1 and 3.4 × 10-3 to 20.7 × 10-3 mol L-1, respectively. The rate of polymerization (Rp) was found to be Rp = k[BPO]0.51[FMA]1.69. The overall activation energy of 84 kJ mol-1 was obtained in the temperature range 70-90 °C. The FTIR spectra of the prepared polymer indicate disappearance of the band at 1620 cm-1, which is basically due to the olefinic C=C stretching, confirming the polymerization of N-[(furan-2-yl)methyl]acrylamide.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- X. Chen, M.A. Dam, K. Ono, A. Mal, H. Shen, S.R. Nutt, K. Sheran and F. Wudl, Science, 295, 1698 (2002).
- H. Laita, S. Boufi and A. Gandini, Eur. Polym. J., 33, 1203 (1997).
- A. Gandini, Polym. Chem., 1, 245 (2010).
- M. Shi and M.S. Shoichet, J. Biomater. Sci. Polym. Ed., 19, 1143 (2008).
- S. Kantevari, T. Yempala, G. Surineni, B. Sridhar, P. Yogeeswari and D. Sriram, Eur. J. Med. Chem., 46, 4827 (2011).
- M. Shi, K. Ho, A. Keating and M.S. Shoichet, Adv. Funct. Mater., 19, 1689 (2009).
- H. Liu, B. Lepoittevin, C. Roddier, V. Guerineau, L. Bech, J.-M. Herry, M.-N. Bellon-Fontaine and P. Roger, Polymer, 52, 1908 (2011).
- M.Z. Elsabee, E.A. Ali, S.M. Mokhtar and M. Eweis, React. Funct. Polym., 71, 1187 (2011).
- N. Sibold, P.J. Madec, S. Masson and T.N. Pham, Polymer, 43, 7257 (2002).
- R. Ribic, L. Habjanec, M. Brgles, S. Tomic and J. Tomasic, Bioorg. Med. Chem., 17, 6096 (2009).
- C. Song, L. Li, F. Wang, J. Deng and W. Yang, Polym. Chem., 2, 2825 (2011).
- A.M. Atta, H.S. Ismail and A.M. Elsaaed, J. Appl. Polym. Sci., 123, 2500 (2012).
- T. Singh and R. Singhal, J. Appl. Polym. Sci., 125, 1267 (2012).
- Z. Liu, M. Cardosi, J. Rodgers, G. Lillie and L. Simpson, React. Funct. Polym., 70, 715 (2010).
- H.M. Li, J. Zhuang, H.B. Liu, L. Feng and W. Dong, Polym. Eng. Sci., 52, 431 (2012).
- M. Liu, J. Chen, Y.P. Cheng, Y.N. Xue, R.X. Zhuo and S.W. Huang, Macromol. Biosci., 10, 384 (2010).
- J.I. Ngadaonye, L.M. Geever, M.O. Cloonan and C.L. Higginbotham, J. Polym. Res., 19, 9822 (2012).
- B. Singh, G.S. Chauhan, S. Kumar and N. Chauhan, Carbohydr. Polym., 67, 190 (2007).
- P.A. Kavakli, C. Uzun and O. Guven, React. Funct. Polym., 61, 245 (2004).
- F.A. Al-Sagheer, A.A.M. Ali, M.A. Reyad and M.Z. Elsabee, Polym. Int., 44, 88 (1997).
- A.Z. El-Sonbati, M.A. Diab and R.H. Mohamed, Polym. Int., 60, 1467 (2011).
- M. Solener, J. Appl. Polym. Sci., 109, 1461 (2008).
- C.H. Bamford and E. Schofield, Polymer, 24, 433 (1983).
- K. Behari, K. Taunk and R. Das, Polym. Int., 46, 126 (1998).
References
X. Chen, M.A. Dam, K. Ono, A. Mal, H. Shen, S.R. Nutt, K. Sheran and F. Wudl, Science, 295, 1698 (2002).
H. Laita, S. Boufi and A. Gandini, Eur. Polym. J., 33, 1203 (1997).
A. Gandini, Polym. Chem., 1, 245 (2010).
M. Shi and M.S. Shoichet, J. Biomater. Sci. Polym. Ed., 19, 1143 (2008).
S. Kantevari, T. Yempala, G. Surineni, B. Sridhar, P. Yogeeswari and D. Sriram, Eur. J. Med. Chem., 46, 4827 (2011).
M. Shi, K. Ho, A. Keating and M.S. Shoichet, Adv. Funct. Mater., 19, 1689 (2009).
H. Liu, B. Lepoittevin, C. Roddier, V. Guerineau, L. Bech, J.-M. Herry, M.-N. Bellon-Fontaine and P. Roger, Polymer, 52, 1908 (2011).
M.Z. Elsabee, E.A. Ali, S.M. Mokhtar and M. Eweis, React. Funct. Polym., 71, 1187 (2011).
N. Sibold, P.J. Madec, S. Masson and T.N. Pham, Polymer, 43, 7257 (2002).
R. Ribic, L. Habjanec, M. Brgles, S. Tomic and J. Tomasic, Bioorg. Med. Chem., 17, 6096 (2009).
C. Song, L. Li, F. Wang, J. Deng and W. Yang, Polym. Chem., 2, 2825 (2011).
A.M. Atta, H.S. Ismail and A.M. Elsaaed, J. Appl. Polym. Sci., 123, 2500 (2012).
T. Singh and R. Singhal, J. Appl. Polym. Sci., 125, 1267 (2012).
Z. Liu, M. Cardosi, J. Rodgers, G. Lillie and L. Simpson, React. Funct. Polym., 70, 715 (2010).
H.M. Li, J. Zhuang, H.B. Liu, L. Feng and W. Dong, Polym. Eng. Sci., 52, 431 (2012).
M. Liu, J. Chen, Y.P. Cheng, Y.N. Xue, R.X. Zhuo and S.W. Huang, Macromol. Biosci., 10, 384 (2010).
J.I. Ngadaonye, L.M. Geever, M.O. Cloonan and C.L. Higginbotham, J. Polym. Res., 19, 9822 (2012).
B. Singh, G.S. Chauhan, S. Kumar and N. Chauhan, Carbohydr. Polym., 67, 190 (2007).
P.A. Kavakli, C. Uzun and O. Guven, React. Funct. Polym., 61, 245 (2004).
F.A. Al-Sagheer, A.A.M. Ali, M.A. Reyad and M.Z. Elsabee, Polym. Int., 44, 88 (1997).
A.Z. El-Sonbati, M.A. Diab and R.H. Mohamed, Polym. Int., 60, 1467 (2011).
M. Solener, J. Appl. Polym. Sci., 109, 1461 (2008).
C.H. Bamford and E. Schofield, Polymer, 24, 433 (1983).
K. Behari, K. Taunk and R. Das, Polym. Int., 46, 126 (1998).