The Malaysian Journal of Analytical Sciences Vol 14
No 2 (2010): 88 – 99
SYNTHESIS AND CHARACTERIZATION OF SEVERAL LAURYL CHITOSAN DERIVATIVES
Nadhratun Naiim Mobarak, Md.Pauzi Abdullah*
School of Chemical Sciences and Food Technology,
Faculty of Science and Technology, Universiti Kebangsaan
Malaysia,
43600 UKM Bangi, Selangor Darul Ehsan, Malaysia
*Corresponding author: mpauzi@ukm.my
Abstract
Three
derivatives of chitosan namely lauryl chitosan, lauryl succinyl chitosan and
lauryl carboxymethyl chitosan had been synthesized in this study. The synthesis
of lauryl carboxymethyl chitosan and lauryl succinyl chitosan require two steps
of reaction whereas for lauryl chitosan only one step was required. Lauryl carboxymethyl
chitosan was prepared by reacting chitosan with monochloroacetic acid to form
carboxymethyl chitosan. The synthesis of lauryl succinyl chitosan involved the
reaction between chitosan with succinic anhydride to form succinyl chitosan.
After that, the carboxymethyl chitosan and succinyl chitosan were reacted with
dodecanal to form lauryl carboxymethyl chitosan and lauryl succinyl chitosan,
respectively. The addition of lauryl group onto the derivative aim at producing
chitosan derivatives having both hydrophobic and hydrophillic properties. The
chemical structures of the derivatives were characterized by Fourier Transform
Infrared (FTIR), 1H Nuclear Magnetic Resonance (1H NMR)
and Elemental Analysis (CHNS). In the IR spectrum of carboxymethyl chitosan and
succinyl chitosan, peaks at 1645-1630 cm-1, representing C=O were clearly seen. After the substitution
of lauryl group on the derivatives, the presence of peaks at 2930-2860 cm-1
indicates the C-H stretching of lauryl group. The presence of
lauryl group was further supported by the presence of peaks at about 0.8-1.7
ppm in the 1H NMR spectra that assigned for hydrogen that attached
to lauryl group. Elemental analysis was used to compare the derivatives
prepared with the theoretical values.
Keywords: Hydrophilic,
Hydrophobic and Chitosan.
References
1. Ma, G.,
Yang, D., Kennedy, J.F. & Nie, J. 2008. Synthesize and characterization of
organic-soluble acylated chitosan. Carbohydrate Polymers.75: 390-394.
2. Rinaudo,
M. 2006. Chitin and chitosan: Properties and application. Progress in
Polymer Science.31: 603-632.
3. Kurita,
K., Mori, S., Nishiyama, Y. & Harata, M. 2002. N-Alkylation of chitin and
some characteristics of the novel derivatives. Polymer Bulletin.48:159-166.
4. Sui,W., Wang, Y., Dong, S. & Chen, Y.
2008. Preparation and properties of an amphiphilic derivative of succinyl-chitosan. Colloids and Surfaces A: Physicochem. Eng.
Aspects. 316 : 171-175.
5. Tikhonov, V.E., Stepnova, E.A, Babak, V.G.,
Krakyukhina, M.A., Brezin, B.B. & Yamskov, I.A. 2008. Reactive &
Functional Polymers. 68: 436-445.
6. Ramos,
V.M., Rodriguez, N.M., Rodriguez, M.S., Heras, A. & Agullo, E. 2003.
Modified chitosan carrying phosphonic and alkyl groups. Carbohydrate
Polymers. 51:425-429.
7. Chen, X.G.
& Park, H.J. 2003. Chemical characteristics of O-carboxymethyl chitosans
related to the preparation conditions. Carbohydrate Polymers 53: 355-359.
8. Zhu, A., Yuan, L. & Lu, Y. 2007.
Synthesis and aggregation behavior of N-succinyl-O-carboxymethylchitosan in
aqueous solutions. Colloids Polymer Science 285:1535-1541.
9. Elsabee, M.Z, Morsi, R.E. & Al-Sabagh,
A.M. 2009. Surface active properties of chitosan and its derivatives. Colloids
and Surfaces B: Biointerfaces, 74:1-16.
10. Pavia, D.L., Lampman, G.M., & Kriz, G.S.
2001. “Introduction to spectroscopy”,third edition/Ed.
11. Miwa, A., Ishibe, A., Nakano, M., Yamahira,
T., Itai, S., Jinno, S., & Kawahara, H. 1998. Development of Novel Chitosan
Derivatives as Micellar Carriers of Taxol. Pharmaceutical Research.
15(12):1844-1850.
12. Zhang, C., Ping, Q., Zhang, H. & Shen, J.
2003. Synthesis and characterization of water soluble O-succinyl-chitosan. European
Polymer Journal 39 1629-1634.
13. Aiping, Z.,
Lanhua, Y. & Yan, L. 2007. Synthesis and
aggregation behavior of N-succinyl-o-carboxymethylchitosan in aqueous
solutions. Colloid Polym Sci 285: 1534-1541.
14. Muzzarelli,
R.A.A,Frega, N., Miliani, M.,Muzzarelli, C. & Cartolari, M. 2000. Interaction of
chitin, chitosan, N-lauryl chitosan and N-dimethylaminopropyl chitosan with
olive oil. Carbohydrate Polymers 43:263-268.