Preparation and evaluation of sulphonamide nonionic surfactants

M. H. M. Ahmed

doi:10.3989/gya.053509

Authors

M. H. M. Ahmed Chemistry Department, Faculty of Science, Benha University

DOI:

https://doi.org/10.3989/gya.053509

Keywords:

Biological activity, Nonionic surfactant, K10 clay catalyst, Surface activity

Abstract

Alkyl (octyl, decyl and dodecyl; C₈,C₁₀ and C₁₂) benzene sulphonyl chloride was used in the preparation of a novel series of nonionic surfactants (IV-VI)a-c, (VII-IX) a-c and (X-XII)a-c. The preparations were completed by reacting each alkyl (C₈,C₁₀ and C₁₂) benzene sulphonyl chloride with ethanolamine to give (I-III) respectively. The resulting products were reacted separately with ethylene oxide in the presence of different (base KOH, Lewis acid SnCl₄ and k10 clay) catalysts to produce different moles of nonionic surfactants (5, 7 and 9) in sequence corresponding to (IV-VI)a-c, (VII-IX) a-c and (X-XII)a-c respectively. The chemical structures of prepared nonionic surfactants were elucidated by IR and ¹HNMR spectra. The surface activity, biodegradability and biological activities of the prepared compounds were investigated. The obtained data show that these compounds have good surface and biological activities as well as reasonable biodegradability properties.

Downloads

Download data is not yet available.

References

Ahmed MHM, El-Dougdoug WIA, Sallay P. 2002. Preparation and evaluation of surface active properties of oxypropylated aralkyl sulphate. Journal of Olaj, Szappan, Kozmetika 51, 77- 80.

Ahmed MHM, Sallay P, Rusznak I, Farkas L. 1996. Determination of the average ethoxylation degree. Journal of Tenside Surfactants Detergents 33, 410-411.

Al-Haiza MA, Mostafa MS, El-Kady MY. 2003. Synthesis and Biological Evaluation of Some New Coumarin Derivatives. Molecules 8, 275-286. doi:10.3390/80200275

Amin MS, Eissa AMF, Shaaban AF, El-Sawy AA, El-Sayed R. 2004. New heterocycles having a double characters; as antimicrobial and surface active agents. Part 1: Nonionic compounds from fatty acid isothiocyanate. Grasas Y Aceites 55, 370-376.

Assassi N, Azira H, Tazerouti A. 2006. Recent progress in the manufacture of alkanesulfonates photosulfochlorination of single chain length (C12 – C16) n-alkanes using SO2Cl at high conversion rates in pure phase and in presence of solvent. Journal of Surfactants and Detergents 9, 249-257. doi:10.1007/s11743-006-5005-0

Azira H, Assassi N, Tazerouti A. 2003. Synthesis of long chain alkanesulfonates by photosulfochlorination using sulfuryl chloride. Journal of Surfactants and Detergents 6, 55-59. doi:10.1007/s11743-003-0248-3

Bailey FE Jr., Joseph VK. 1991. Alkylene Oxides and Their Polymers. Marcel Dekker, Inc., New York. Basel, 35, Ch. 7, p 205.

Braun AM, Maurette MT, Oliveros E. 1986. Technologies photochimiques, 1st edn. Presses Polytechniques Romandes, Lausanne, p 337.

Chiu-Chun Lai, Keng-Ming Chen. 2008. Preparation and surface activity of polyoxyethylene-carboxylated modified Gemini surfactants. Colloids and Surfaces A: Physicochem. Eng. Aspects 320, 6-10. doi:10.1016/j.colsurfa.2007.12.056

Cohen AW, Rosen MJ. 1981. Wetting properties of nonionic surfactants of homogeneous structure. Journal of American Oil Chemist’s Society (S & D). 1062-1066.

Durham K. 1961. Surface Activity and Detrgency, MacMillan Co. Ltd. London.

Egorov NS. 1965. Microbe antagonists and Biological Assessment of their Antibiotics Activity, Moscow, Vysshaya Shkola Publishers (in Russia).

El-Sukkary MA, El-Sawy AA, El-Dib F. 1987. Synthetic Detergents from Crude rice bran oil. Hungarian Journal of Industrial Chemistry 15, 317-322.

Etre ET, Richard RE, Darid A. 1974. Biodegradable surfactants derived from corn starch. Journal of American Oil Chemist’s Society 51, 486-491. doi:10.1007/BF02635857

Fainerman VB, Mobius D, Miller R. 2001. Surfactants: Chemistry, Interfacial Properties, Applications, Elsevier, Amsterdam-London-New York- Oxford- Paris - Shannon - Tokyo 1st edn. Ch. 1. p 9.

Falbe J. 1987. Surfactants in Consumers Products, Springer-Verlag, Heidelberg New York London Pairs Tokyo, p. 149.

Findely A. 1963 Practical Chemistry” Longmans, London, 6th, 1040 .

Hreczuch W, Trathnigg B, Dziwinski E, Pyzalski K. 2001. Direct Ethoxylation of a Longer-Chain Aliphatic Ester. Journal of Tenside Surfactants Detergents 4, 167-173. doi:10.1007/s11743-001-0171-7

Maria S, Holmberg K. 2005. Synthesis, Stability, and Biodegradability Studies of a Surface-Active Amide. Journal of Tenside Surfactants Detergents 8, (4), 331-336. doi:10.1007/s11743-005-0364-0

Mousli RE, Amel T. 2007. Direct Method of Preparation of Dodecanesulfonamide Derivatives and Some Surface Properties. Journal of Surfactants and Detergents 10, 279-285. doi:10.1007/s11743-007-1043-5

Nico M van Os. 1998. Nonionic Surfactants Organic Chemistry, Surfactant Science Series” Marcel Dekker, INC, 72, Ch. 1, p 4-33.

Reinskje T, Thorsten S, Jan BFN Engberts. 2004. Aggregation behavior of p-n-alkylbenzamidinium chloride surfactants. Journal of Colloid and Interface Science 276, 212-220. doi:10.1016/j.jcis.2004.03.030 PMid:15219451

Rosen JM. 2004. Surfactants and Interfacial phenomena. Third Edn. A John Wiley & Sons, INC., Publication. P. 208.

Saito Y, Sato T, Anazawa I. 1989. Correlation between Distribution of oxyethylene chain and Physicochemical Properties of Nonionic Surfactants. Yakuzaigaku, 49, 180-183.

Sallay P, Bekássy S, Ahmed MH, Farkas L, Rusznák I. 1997 .A Novel Way for Hydroxyethylation by Clay Catalyst. Tetrahedron Letters 38, 661-664. doi:10.1016/S0040-4039(96)02386-6

Sallay P, Ahmed MHM, Bekasy S, Farkas L, Vig A, Rusznak I. 2000. Molar Mass Distribution of Hydroxyethylation of aralkyl alcohols. Periodic Polytechnica Series Chemical Engineering 44, 95-110.

Sandler RS, Hemlock L. 1989 U.S.P.O., 0 371 271 B1S 4.

Sandler RS. 1991 U.S.P.O., 2 028 717.

Schönfeld N. 1967. Surface Active Ethylene Oxide Adducts. Pergamon press, Oxford p 25, 45.

Takeshi H. 1970. Studies of ester containing surfactant: Preparation and properties of sodium sulphalkanoates. Bulletin Chemical Society of Japan 43, 2236-2240. doi:10.1246/bcsj.43.2236