Zwitterionic surfactants—β-alkyl aspartates are prepared by the addition reaction of ammonia to alkyl maleates. Factors are discussed that influence the quality and yields of obtained β-alkyl aspartates. Structures of obtained surfactants are confirmed by 1H NMR and IR spectra. The applicability of these materials is characterized by evaluation of their surface activity, toxicity and biodegradability.
References
[1]
Perez, L., Pinazo, A., Garcia, T.M., Lozano, M., Manresa, A., Vinardell, M.P., Mitjans, M., Pons, R. and Infante, R.M. (2009) Cationic Surfactants from Lysine: Synthesis, Micellization and Biological Evaluation. European Journal of Medicinal Chemistry, 44, 1884-1892. http://dx.doi.org/10.1016/j.ejmech.2008.11.003
[2]
Albert, R., Danklmaier, J., Hoenig, H. and Kandolf, H. (1987) A Simple and Convenient Synthesis of β-Aspartates and γ-Glutamates. Synthesis, 1987, 635-637. http://dx.doi.org/10.1055/s-1987-28030
[3]
Suzuk, M., Yumoto, M., Shirai, H. and Hanabusa, K. (2008) A Family of Low-Molecular-Weight Organogelators Based on Nα, Nε-diacyl-L-Lysine: Effect of Alkyl Chains on Their Organogelation Behavior. Tetrahedron, 64, 10395-10400. http://dx.doi.org/10.1016/j.tet.2008.08.061
[4]
Boros, M., Koekoesi, J., Vamos, J., Koevesdi, I. and Noszal, B. (2007) Methods for Syntheses of N-Methyl-DL-As-partic Acid Derivatives. Amino Acids, 33, 709-717. http://dx.doi.org/10.1007/s00726-006-0453-4
[5]
Zilkha, A. and Bachi, M.D. (1959) Syntheses of N-Alkyl Aspartic Acids and N2-Alkyl-α-Asparagines. The Journal of Organic Chemistry, 24, 1096-1098. http://dx.doi.org/10.1021/jo01090a015
[6]
Bordes, R. and Holmberg, K. (2015) Amino Acid-Based Surfactants: Do They Deserve More Attention? Advances in Colloid and Interface Science, 222, 79-91. http://dx.doi.org/10.1016/j.cis.2014.10.013
[7]
Rosen, M.J. and Kunjappu, J.T. (2012) Surfactants and Interfacial Phenomena. 4th Edition, John Wiley & Sons Ltd., New York. http://dx.doi.org/10.1002/9781118228920
[8]
Bordes, R. and Holmberg, K. (2009) Amino Acid-Based Surfactants. In: Somasundaran, P., Ed., Encyclopedia of Surface and Colloid Science, 2nd Edition, Taylor & Francis, Goeteborg.
[9]
Infante, M.R., Perez, I., Pinazo, A., Clapes, P. and Moran, M.C. (2003) Amino Acid-Based Surfactants. In: Holmberg, K., Ed., Novel Surfactants: Preparation, Applications and Biodegradability, Marcel Dekker, Inc., New York, Basel. http://dx.doi.org/10.1201/9780203911730.ch5
[10]
Vulfson, E. (2001) Enzymatic Synthesis of Surfactants. In: Friedli, F.E., Ed., Detergency of Specialty Surfactants, Marcel Dekker, Inc., New York.
[11]
Valivety, R., Gill, I.S. and Vulfson, E.N. (1998) Application of Enzymes to the Synthesis of Amino Acid-Based Bola and Gemini Surfactants. Journal of Surfactants and Detergents, 1, 177-185. http://dx.doi.org/10.1007/s11743-998-0017-3
[12]
Valivety, R., Jauregi, P., Gill, I. and Vulfson, E. (1997) Chemo-Enzymatic Synthesis of Amino Acid-Based Surfactants. Journal of the American Oil Chemists’ Society, 74, 879-886. http://dx.doi.org/10.1007/s11746-997-0232-8
[13]
Li, Y. (2011) Synthesis and Physicochemical Study of Novel Amino Acid Based Surfactants. Master Thesis, Chalmers University, Goeteborg.
[14]
(2016) Daphtoxkit FTM Magna. Crustacean Toxicity Screening Test for Freshwater Standard Operational Procedure. http://www.microbiotests.be/SOPs/Daphtoxkit%20magna%20F%20SOP%20-%20A5.pdf
[15]
(2016) Rapidtoxkit. Microbiotest for Rapid Detection of Water Contamination. Standard Operational Procedure. http://www.microbiotests.be/SOPs/Rapidtoxkit%20F%20SOP%20-%20A5
[16]
Laskovs, A., Laskovs, E., Grinbergs, A., Uljanovs, A. and Mutere, O. (2011) Consortium P1035 of Microorganisms-Destructors and Its Use for Degradation of Hydrocarbons. Latvian Patent No LV14347.
[17]
Conway, R.A., Waggy, G.T., Spiegel, M.H. and Berglund, R.L. (1983) Environmental Fate and Effects of Ethylene Oxide. Environmental Science & Technology, 17, 107-112. http://dx.doi.org/10.1021/es00108a009
[18]
NaleczJawecki, G., Szczesny, L., Solecka, D. and Sawicki, J. (2011) Short Ingestion Tests as Alternative Proposal for Conventional Range Finding Assays with Thamnocephalus platyurus and Brachionus calyciflorus. International Journal of Environmental Science and Technology, 8, 687-694. http://dx.doi.org/10.1007/BF03326253
[19]
Torokné, A., Vasdinnyei, R. and Asztalos, B.M. (2007) A Rapid Microbiotest for the Detection of Cyanobacterial Toxins. Environmental Toxicology, 22, 64-68. http://dx.doi.org/10.1002/tox.20235
[20]
(2014) OECD Guidelines for the Testing of Chemicals. Test No. 310: Ready Biodegradability—CO2 in Sealed Vessels (Headspace Test). http://dx.doi.org/10.1787/2074577x