AJAC  Vol.4 No.9 , September 2013
Green Synthesis, Composition Analysis and Surface Active Properties of Sodium Cocoyl Glycinate
ABSTRACT

Cocoyl glycine was synthesized directly from coconut oil and sodium glycinate in yield of 87%. IR, ESI-MS and LC/MS analysis results showed that cocoyl glycine consists of a series of acyl glycines with different acyl chain lengths, and the proportion of each component was consistent with the composition of fatty acids derived from coconut oil. The surface tension and the Critical Micelle Concentration (CMC) of corresponding sodium salt were evaluated. The result showed that sodium cocoyl glycinate reduced the surface tension of water to a minimum value of approximately 33 mN·m-1 at CMC of 0.21 mmol·L-1.


Cite this paper
G. Zhang, B. Xu, F. Han, Y. Zhou, H. Liu, Y. Li, L. Cui, T. Tan and N. Wang, "Green Synthesis, Composition Analysis and Surface Active Properties of Sodium Cocoyl Glycinate," American Journal of Analytical Chemistry, Vol. 4 No. 9, 2013, pp. 445-450. doi: 10.4236/ajac.2013.49056.
References
[1]   R. S. Lanigan, “Final Report on the Safety Assessment of Cocoyl Sarcosine, Lauroyl Sarcosine, Myristoyl Sarcosine, Oleoyl Sarcosine, Stearoyl Sarcosine, Sodium Cocoyl Sarcosinate, Sodium Lauroyl Sarcosinate, Sodium Myristoyl Sarcosinate, Ammonium Cocoyl Sarcosinate, and Ammonium Lauroyl Sarcosinate,” International Journal of Toxicology, Vol. 20, No. 1, 2001, pp.1-14. doi:10.1080/10915810152902547X

[2]   G. O. Reznik, P. Vishwanath, M. A. Pynn, J. M. Sitnik, J. J. Todd, J. Wu, et al., “Use of Sustainable Chemistry to Produce an Acyl Amino Acid Surfactant,” Applied Microbiology and Biotechnology, Vol. 86, No. 5, 2010, pp. 1387-1397. doi:10.1007/s00253-009-2431-8

[3]   A. Hartmann and G. Speit, “The Contribution of Cytotoxicity to DNA Effects in the Single Cell Gel Test (comet assay),” Toxicology Letters, Vol. 90, No. 2-3, 1997, pp. 183-188. doi:10.1016/S0378-4274(96)03847-7

[4]   J. D. Xia, Y. M. Xia and I. A. Nnanna, “Structure-Function Relationship of Acyl Amino Acid Surfactants: Surface Active and Antimicrobial Properties,” Journal of Agricultural and Food Chemistry, Vol. 43, No. 4, 1995, pp. 867-871. doi:10.1021/jf00052a004

[5]   P. Mary and D. D. Bendejacq, “Interactions between Sulfobetaine-Based Polyzwitterions and Polyelectrolytes,” Journal of Physical Chemistry B, Vol. 112, No. 8, 2008, pp. 2299-2310. doi:10.1021/jp0769274

[6]   E. Jungermann, J. F. Gerecht and I. J. Krems, “The Preparation of Long Chain N-Acylamino Acids,” Journal of the American Chemical Society, Vol. 78, No. 1, 1956, pp. 172-174. doi:10.1021/ja01582a049

[7]   R. Bordes and K. Holmberg, “Physical Chemical Characteristics of Dicarboxylic Amino Acid-based Surfactants,” Colloids and Surfaces A: Physicochemical and Engineering Aspects, Vol. 391, No. 1-3, 2011, pp. 32-41. doi:10.1016/j.colsurfa.2011.03.023

[8]   M. Gerova, F. Rodrigues, J.-F. Lamère, A. Dobrev and S. Fery-Forgues, “Self-assembly Properties of Some Chiral N-Palmitoyl Amino Acid Surfactants in Aqueous Solution,” Journal of Colloid and Interface Science, Vol. 319, No. 2, 2008, pp. 526-533. doi:10.1016/j.jcis.2007.12.004

[9]   M. Hassanzadeh, M. Kambarani, L. Tayebi, F. Yazdian, “Kinetic Study of Sodium Cocoyl Sarcosinate Synthesis and Factors Affecting the Reaction on Bench and Pilot Scales,” Journal of Surfactants and Detergents, Vol. 15, No. 5, 2012, pp. 551-556. doi:10.1007/s11743-012-1333-4

[10]   S.-F. Wang, T. Furuno and Z. Cheng, “Synthesis of New Amino Acid-type Amphoteric Surfactants from Tall Oil Fatty Acid,” Journal of Wood Science, Vol. 47, No. 6, 2001, pp. 470-475. doi:10.1007/BF00767900

[11]   T. Izumi, Y. Yagimuma and M. Haga, “Enzymatic Syntheses of N-Lauroyl-β-Alanine Homologs in Organic Media,” Journal of the American Oil Chemists’ Society, Vol. 74, No. 7, 1997, pp. 875-878. doi:10.1007/s11746-997-0231-9

[12]   R. Valivety, P. Jauregi, I. Gill and E. Vulfson, “Chemo-Enzymatic Synthesis of Amino Acid-Based Surfactants,” Journal of the American Oil Chemists’ Society, Vol. 74, No. 7, 1997, pp. 879-886. doi:10.1007/s11746-997-0232-8

[13]   L. Goujard, M.C. Figueroa and P. Villeneuve, “Chemo-Enzymatic Synthesis of N-Arachidonoyl Glycine,” Biotechnology Letters, Vol. 26, No. 15, 2004, pp. 1211-1216. doi:10.1023/B:BILE.0000036597.25673.33

[14]   H. Bidin, M. Basri, S. M. Radzi, A. Ariff, R. N. Z. R. A. Rahman and A. B. Salleh, “Optimization of Lipase-Catalyzed Synthesis of Palm Amino Acid Surfactant Using Response Surface Methodology (RSM),” Industrial Crops and Products, Vol. 30, No. 2, 2009, pp. 206-211. doi:10.1016/j.indcrop.2009.03.006

[15]   K. A. G. Gopala, R. Gaurav, S. B. Ajit, K. P. K. Prasanth and C. Preeti, “Coconut Oil: Chemistry, Production and Its Applications—A Review,” Indian Coconut Journal, Vol. 73, No. 3, 2010, pp.15-27.

[16]   E. M. A. Dauqan, H. A. Sani, A. Abdullah and Z. M. Kasim. “Fatty Acids Composition of Four Different Vegetable Oils (Red Palm Olein, Palm Olein, Corn Oil and Coconut Oil) by Gas Chromatography,” 2011 2nd International Conference on Chemistry and Chemical Engineering, Chengdu, China, 29-31 July 2011, pp. 31-34. http://www.ipcbee.com/vol14/6-C016.pdf

[17]   T. Yoshimura, A. Sakato, K. Tsuchiya, T. Ohkubo, H. Sakai, M. Abe, et al., “Adsorption and Aggregation Properties of Amino Acid-based N-alkyl Cysteine Monomeric and N,N’-Dialkyl Cystine Gemini Surfactants,” Journal of Colloid and Interface Science, Vol. 308, No. 2, 2007, pp. 466-473. doi:10.1016/j.jcis.2006.11.038

[18]   V. Dana, P. Aurelia, E. C. Irina and C. C. Mihai, “Aspects Regarding the Synthesis and Surface Properties of Some Glycine Based Surfactants,” Scientific Bulletin— Universitatea Politehnica din Bucuresti, Series B, Vol. 73, No. 3, 2011, pp. 147-154.

[19]   G. B. Ray, S. Ghosh and S. P. Moulik, “Physicochemical Studies on the Interfacial and Bulk Behaviors of Sodium N-Dodecanoyl Sarcosinate (SDDS),” Journal of Surfactants and Detergents, Vol. 12, No. 2, 2009, pp. 131-143. doi:10.1007/s11743-008-1105-3

[20]   A. Sivasamy, M. Krishnaveni and P.G. Rao, “Preparation, Characterization, and Surface and Biological Properties of N-Stearoyl Amino Acids,” Journal of the American Oil Chemists’ Society, Vol. 78, No. 9, 2001, pp. 897-902. doi:10.1007/s11746-001-0361-5

 
 
Top