Malaysian Journal of Analytical Sciences Vol 19 No 1 (2015): 230 – 235

 

 

 

SINTESIS SURFAKTAN ASID AMINO TERASIL-N DARIPADA

L-PROLINA DAN PALMITOIL KLORIDA

 

(Synthesis of  N-Acylated Amino Acid Surfactant from L-Proline and Palmitoyl Chloride)

 

Meutia Fadhilah Hasibuan, Mohd. Wahid Samsudin, Rahimi M. Yusop, Suria Ramli*

 

Pusat Pengajian Sains Kimia dan Teknologi Makanan,

Fakulti Sains dan Teknologi

Universiti Kebangsaan Malaysia, 43000 UKM Bangi, Selangor D.E, Malaysia

 

*Corresponding author: su_ramli@ukm.edu.my

 

 

Abstrak

Surfaktan asid amino terasil-N yang kurang toksik, boleh dibiodegradasi dan mesra alam telah dihasilkan daripada tindak balas antara asid amino L-prolina dengan palmitoil klorida melalui proses asilasi menggunakan kaedah Schotten-Baumann. Produk hasil tindak balas berbentuk mendakkan putih dengan peratusan hasil mentah 72% dan takat lebur 52^oC - 58^oC. Kumpulan berfungsi amida yang dikesan menggunakan kaedah Transfromasi Fourier Infra Merah menunjukkan kehadiran N-palmitoil prolina. Analisis ketulenan menggunakan Kromatografi Cecair Prestasi Tinggi dan Lapisan Nipis menunjukkan hasil tindak balas merupakan campuran.

 

Kata kunci: surfaktan terbiodegradasi, asid amino terasil-N, tindak balas pengamidaan, Schotten-Baumann.

 

Abstract

A biodegradable, less toxic and environmentally friendly N-acylated amino acid surfactant was prepared from the amino acid L-proline and palmitoyl chloride through acylation reaction using the Schotten-Baumann reaction condition. The reaction result was a white flake form and the percentage of the crude yield was 72% with melting point in range of 52^oC - 58^oC. Functional group of amide which was detected using Fourier Transform Infrared method showed the presence of N-palmitoyl proline. The purity analysis using High Performance Liquid Chromatography and Thin Layer Chromatography showed the result was a mixture compound.

 

Keywords: biodegradable surfactant, N-acylated amino acids, amidation reaction, Schotten-Baumann

 

References

1.       Takehara, M., Moriyuki, H., Yoshimura, I. and Yoshida, R. (1972). Surface active N-acylglutamate: II Physicochemical properties of long chain N-acylglutamic acids and their sodium salts. Journal of American Chemical Society 49(3): 143-150.

2.       Imae, T., Takashi, Y. and Muramatsu, H. (1992). Formation of fibrous molecular assemblies by amino acid surfactants in water. Journal of American Chemical Society 114(9): 3414-3419.

3.       2010. Schotten-Baumann Reaction. Comprehensive Organic Name Reactions and Reagents. 573:2536–2539

4.       Infante, M. R., Pérez, L., Pinazo, A., Clapés, P., Morán, M. C., Angelet, M., García, M. T. and Vinardell, M. P. (2004). Amino acid-based surfactants. Comptes Rendus Chimie 7: 583-592.

5.       Mhaskar, S. Y., Prasad, R. B. N., and Lakshminarayana. G., (1990). Synthesis of N-acyl amino acids and correlation of structure with surfactant properties of their sodium salts. Journal of the American Oil Chemists’ Society 67(12): 1015-1019.

6.       McMurry, J. (2008). Organic Chemistry. 7e. United States: Brooks/Cole.

7.       Zainab Idris. (2010). Diamidation of Azelaic Acid with Amino Acids and Their Structural Characterization. Tesis Ph.D. Universiti Kebangsaan Malaysia.

8.       Pavia, Lampman, Kriz and Vyvyan. (2010). Infrared Spectroscopy. Dlm. Spectroscopy, hlm 125-187. 4th edition. United States: Brooks/Cole

9.       Harun, N. S., Talip, N. N. M., Hong, L. K., Jamil, M. S. M., & Yusop, R. M. (2013). Phase Behaviour of Fatty Alcohol Sulphate and Fatty Alcohol Ether Sulphate from Palm Based. Malaysian Journal of Analytical Sciences, 17(1), 139-145..

10.    Hong, L. K., Harun, N. S., Jamil, M. S. M., & Yusop, R. M. (2013). Phase Behavior and Rheology of Fatty Alcohol Sulphate, Fatty Alcohol Ether Sulphate from Palm based and Mixtures with other Surfactants. Malaysian Journal of Analytical Sciences, 17(1), 101-108.