Synthesis and surfactant properties of N-acylation compounds derived from hydrolysis degradation products of N-(β-cianoethyl)-ε-caprolactam

Synthesis and surfactant properties of N-acylation compounds derived from hydrolysis degradation products of N-(β-cianoethyl)-ε-caprolactam

N-acyl amino acids can be used as active surface agents in the detergents industry, as well as in the pharmaceutical industry and cosmetics. Properties of these compounds are superior to those of fatty acids soaps and they are not toxic to the environment and have low Kraft points, because of peptide bonds (CO–NH). Acylation at the nitrogen atom can be performed with good yields without catalysts, for strong nucleophilic derivatives. The synthesis of some derivatives of 4-azasebacic acid, which are hydrolysis degradation products from N-(β -cianoethyl)-ε-caprolactam, has been described and the N-acylation processes for these compounds are also presented. The obtained products have been characterized using various methods: IR, UV-VIS, $^ 1 HNMR,^ {13}C-NMR$, elemental analysis, TLC, m.p. (Boethius), and in some cases refractive index. The most important surfactant properties of these N-acylated products were investigated using the surface tension method. The related thermodynamic parameters were also calculated.

___

  • 1. Liyun, Q.; Yun, F.; Zeyun, W.; Liangyu, J.; Yiyou, W. J. Surf. Deterg. 2008, 11, 55-59.
  • 2. Bondarev A., Cuiban F., Mihai S., Pˆantea O., Trˆımbita¸su E. N-acylation of some hydrolysis degradation products of N-(β -cianoethyl)-ε-caprolactam, Sixth National Conference on Chemistry 16th National Symposium ‘Polymers 2008’, Sofia, Bulgaria, 10-14 September 2008.
  • 3. Fisher, G. H.; Amino Acids 2007, 32, 1-6.
  • 4. S´anchez, L.; Mitjans, M.; Infante, M. R.; Garc´ı´y, M.; Manresa, M. A.; Vinardell, P. Amino Acids 2007, 32, 133-136.
  • 5. Nishimura, K.; Tomoda, Y.; Nakamoto, Y.; Kawada, T.; Ishii, Y.; Nagata, Y. Amino Acids 2007, 32, 59-62.
  • 6. Silverstein, R. M.; Webster F.; Kiemle D. Spectrometric Identification of Organic Compounds, John Wiley & Sons, Inc., 2005.
  • 7. Franses, E. I.; Prosser, A. J.; Infante, M.; Perez, L.; Pinazo, A.; Surfactant Science Series, 2004, 117, 65-92.
  • 8. Laschewski, A.;enside Surfactants Detergents 2003, 40, 246-249.
  • 9. Popescu, G.; Albu, B.; Nuta, D.; Rata, D.; Aldea, E.; Dinescu, G.; Olteanu, M.; Bucharest University Bulletin – Chemistry 2003, I-II, 49 -53.
  • 10. Varade, D.; Mody, S.; Ankleshwaria, H.; Bahadur, P.;enside Surfactants Detergents 2003, 40 , 46-51.
  • 11. Zana, R.;olloid and Interface Science 2002, 97, 203-205.
  • 12. Greksdova, O.; Oremnsova, J.;enside Surfactants Detergents 2002, 39, 40-47.
  • 13. Cuiban, F.; Bolocan, I.; Barbu, E.;rkivoc 2001, N-Substituted derivatives of ε - caprolactam and their thermal and chemical behavior, In memoriam C.D. Nenitzescu on the occasion of his 100th birthday.
  • 14. Holmberg, K.; Colloid and Interface Science 2001, 6, 148-151.
  • 15. Berna, J. L.; Battersby, N.; Cavalli, L.; Fletcher, R.; Guldner, A.; Schowanek, D.; Steber, J.;enside Surfactants Detergents 2001, 38, 86-93.
  • 16. Beller, M.; Eckert, M.; Angewandte Chemie International Edition 2000, 6, 1010-1027.
  • 17. Padmashree, T. S.; Vijayalakshmi, L; Puttaraj, S. J. Food Sci. Technol. 1987, 24, 221-225.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

Determination of trace element contents of Thymus species from Turkey

F. Zehra KÜÇÜKBAY, Ebru KUYUMCU

Nile Blue-hexacyanoferrate carbon paste modified electrode as an amperometric sensor for determination of hydrazine

Reza Emamali SABZI, Elnaz MINAIE, Khalil FARHADI, Mir Maqsoud GOLZAN

Quantum chemical studies on tautomerism and basicity behavior of some 1,2,4-triazole derivatives

Cemil ÖĞRETİR, Yadigar GÜLSEVEN SIDIR, İsa SIDIR and Erol TAŞAL

Computational study on nitronium squarate – potential oxidizers for solid rocket propulsion

Elif GÖKÇINAR, Thomas M. KLAPÖTKE

Determination of ceftriaxone, ceftizoxime, paracetamol, and diclofenac sodium by capillary zone electrophoresis in pharmaceutical formulations and in human blood serum

Amber SOLANGI, Saima MEMON, Arfana MALLAH, Najma MEMON

Biotransformation of danazol by Fusarium solani and Gibberella fujikuorii, and prolyl endopeptidase inhibition studies of transformed products

Muhammad Iqbal CHOUDHARY

Ethyl 5-oxo-3-arylamino-2,5-dihydroisoxazole-4- carboxylates as sources of imidazopyrimidine and aminoindole derivatives

Ahmad POURSATTAR MARJANI, Jabbar KHALAFY

Vapor phase alkylation of toluene using various alcohols over H3PO4/MCM-41 catalyst: Influence of reaction parameters on Vapor phase alkylation of toluene using various alcohols over H3PO4/MCM-41 catalyst: influence of reaction parameters on selectivity and conversion

Alireza ABBASPOURRAD, Roozbeh Javad KALBASI, Farzad ZAMANI

Comparative essential oil analysis of Geranium sylvaticum extracted by hydrodistillation and microwave distillation

Nuran KAHRİMAN, Gonca TOSUN, Hasan GENÇ, Nurettin YAYLI

Synthesis and surfactant properties of N-acylation compounds derived from hydrolysis degradation products of N-(β-cianoethyl)-ε-caprolactam

Andreea BONDAREV