Characterization, surface properties and biological activity of some synthesized anionic surfactants

Nabel A. Negm; Salah M. Tawfik

Journal of Industrial and Engineering Chemistry, Vol.20, No.6, 4463-4472, November, 2014

DOI10.1016/j.jiec.2014.02.018 Export Citation

Characterization, surface properties and biological activity of some synthesized anionic surfactants

Nabel A. Negm, and Salah M. Tawfik^†

Egyptian Petroleum Research Institute, Nasr City, Cairo, Egypt

E-mail:

In this study, esterification reaction between four different fatty alcohols (octyl, dodecyl, hexdecyl and octadecyl alcohol) and phosphoric acid was performed. The produced compound was reacted with polyethylene glycol-400. Then, the reaction product was quenched using sodium hydroxide to form the desired anionic gemini surfactants. The chemical structures of the synthesized surfactants were recognized by FT-IR and 1H NMR spectroscopy. The synthesized surfactants showed higher surface activity. The emulsion stability measurements showed the applicability of these surfactants as emulsifying agents. The foaming power measurements showed the synthesized surfactants have low ability to foam formation. The thermodynamic parameters showed their tendency toward adsorption at the interfaces and also micellization in the bulk of their solutions. The studied surfactants were evaluated as antimicrobial agents against pathogenic bacteria using inhibition zone diameters. The synthesized surfactants showed good antimicrobial activities against the tested microorganisms including Gram positive, Gram negative as well as fungi. The promising inhibition efficiency of these compounds against the pathogenic bacteria facilitates them to be applicable in the petroleum field as new categories of biocides.

Keywords:Antimicrobial activity;Anionic surfactants;Surface activity;Thermodynamic parameters

[References]

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Yoshimura T, Nyuta K, Esumi K, Langmuir, 21(7), 2682 (2005)
Nyuta K, Yoshimura T, Tsuchiya K, Ohkubo T, Sakai H, Abe M, Esumi K, Langmuir, 22(22), 9187 (2006)
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Oda R, Huc I, Homo JC, Heinrich B, Schmutz M, Candau S, Langmuir, 15(7), 2384 (1999)
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Sikiric M, Primozic I, Filipovic-Vincekovic N, J. Colloid Interface Sci., 250(41), 221 (2002)
Sikiric M, Primozic I, Talmon Y, Filipovic-Vincekovic N, J. Colloid Interface Sci., 281(2), 473 (2005)
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Duivenvoorde FL, Feiters MC, Vandergaast SJ, Engberts JB, Langmuir, 13(14), 3737 (1997)
Jaeger DA, Wang YP, Pennington RL, Langmuir, 18(24), 9259 (2002)
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Zhu YP, Masuyama A, Okahara M, J. Am. Oil Chem. Soc., 68, 268 (1991)
Imokawa G, Tsutsumi H, Kurosaki T, J. Am. Oil Chem. Soc., 55, 141 (1978)
Negm NA, Egypt. J. Chem., 45, 483 (2002)
Negm NA, Aiad IA, J. Surf. Deterg., 12, 313 (2009)
Liu XP, Feng J, Zhang L, Gong QT, Zhao S, Yu JY, Colloids Surf. A: Physicochem. Eng. Asp., 362, 39 (2010)
Chavda S, Bahadur P, Aswal VK, J. Surf. Deterg., 14, 353 (2011)
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Muanza DN, Kim BW, Euler KL, Williams L, Int. J. Pharmacogn., 32, 337 (1994)
Behpour M, Ghoreishi SM, Soltani N, Niasari MS, Corrosion Sci., 51, 1073 (2009)
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Negm NA, Zaki MF, Colloids Surf. A: Physicochem. Eng. Asp., 322, 97 (2008)
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Zana R, Levy H, Colloids Surf. A: Physicochem. Eng. Asp., 127, 229 (1997)
Negm NA, Amouna SM, J. Surf. Deterg, 7(1), 23 (2004)
Dreja M, Pyckhout-Hintzen W, Mays H, Tieke B, Langmuir, 15(2), 391 (1999)
Bendjeriou-Sedjerari A, Derrien G, Charnay C, Zajac J, De Menorval LC, Lindheimer M, J. Colloid Interface Sci., 331(2), 281 (2009)
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Ye Z, Zhang F, Han L, Colloids Surf. A: Physicochem. Eng. Asp., 322, 138 (2008)
Negm NA, Egypt. J. Chem., 45(3), 483 (2002)
Nair R, Shah A, Baluja S, Chanda S, J. Serb. Chem. Soc., 71(7), 733 (2006)
Cukurovali A, Yilmaz I, Gur S, Kazaz C, Eur. J. Med. Chem., 41, 201 (2006)
Negm NA, Morsy SMI, Said MM, Bioorg. Med. Chem., 13, 5921 (2005)
Koch A, Clin. Microbiol. Rev., 16(4), 673 (2003)
Walsh F, Amyes S, Curr. Opin. Microbiol., 7(5), 439 (2004)
Chernomordik I, Kozlov MM, Zimmerberg J, J. Membr. Biol., 146, 1 (1995)
Saier MH Jr., Enzymes in Metabolic Pathways: A Comparative Study of Mechanism, Structure, Evolution, and Control, Harper & Row, New York, 1987.

[Referenced By]

[1] Rosen MJ, Chemtech, 23, 30 (1993)

[2] Zana R, Xia J (Eds.), Gemini Surfactants, Marcel Dekker, New York, 2003.

[3] Zhu YP, Masuyama A, Okahara M, J. Am. Oil Chem. Soc., 67, 459 (1990)

[4] Alami E, Holmberg K, J. Colloid Interface Sci., 239(1), 230 (2001)

[5] Alami E, Holmberg K, Eastoe J, J. Colloid Interface Sci., 247(2), 447 (2002)

[6] Seredyuk V, Alami E, Nyden M, Holmberg K, Peresypkin AV, Menger FM, Langmuir, 17(17), 5160 (2001)

[7] Holmberg K, Adv. Colloid Interface Sci., 13, 100 (2003)

[8] Yoshimura T, Nyuta K, Esumi K, Langmuir, 21(7), 2682 (2005)

[9] Nyuta K, Yoshimura T, Tsuchiya K, Ohkubo T, Sakai H, Abe M, Esumi K, Langmuir, 22(22), 9187 (2006)

[10] Zhou T, Zhao J, J. Colloid Interface Sci., 331(22), 476 (2009)

[11] Oda R, Huc I, Candau SJ, Angew. Chem.-Int. Edit., 37(2), 2689 (1998)

[12] Oda R, Huc I, Homo JC, Heinrich B, Schmutz M, Candau S, Langmuir, 15(7), 2384 (1999)

[13] Wang X, Wang J, Wang Y, Ye J, Yan H, Thomas RK, J. Phys. Chem. B, 107(7), 11428 (2003)

[14] Sikiric M, Primozic I, Filipovic-Vincekovic N, J. Colloid Interface Sci., 250(41), 221 (2002)

[15] Sikiric M, Primozic I, Talmon Y, Filipovic-Vincekovic N, J. Colloid Interface Sci., 281(2), 473 (2005)

[16] Bai GY, Wang JB, Wang YJ, Yan H, Thomas RK, J. Phys. Chem. B, 106(26), 6614 (2002)

[17] Menger FM, Littau CA, J. Am. Chem. Soc., 115, 10082 (1993)

[18] Duivenvoorde FL, Feiters MC, Vandergaast SJ, Engberts JB, Langmuir, 13(14), 3737 (1997)

[19] Jaeger DA, Wang YP, Pennington RL, Langmuir, 18(24), 9259 (2002)

[20] Shukla D, Tyagi VK, Surf. Rev. Lett., 14, 991 (2007)

[21] Zhu YP, Masuyama A, Okahara M, J. Am. Oil Chem. Soc., 68, 268 (1991)

[22] Imokawa G, Tsutsumi H, Kurosaki T, J. Am. Oil Chem. Soc., 55, 141 (1978)

[23] Negm NA, Egypt. J. Chem., 45, 483 (2002)

[24] Negm NA, Aiad IA, J. Surf. Deterg., 12, 313 (2009)

[25] Liu XP, Feng J, Zhang L, Gong QT, Zhao S, Yu JY, Colloids Surf. A: Physicochem. Eng. Asp., 362, 39 (2010)

[26] Chavda S, Bahadur P, Aswal VK, J. Surf. Deterg., 14, 353 (2011)

[27] Sayed GH, Ghuiba FM, Abdou MI, Badr EA, Tawfik SM, Negm NA, J. Surf. Deterg., 15, 735 (2012)

[28] Smail DAI, Negm NA, J. Fac. Edn., 26, 47 (2001)

[29] Muanza DN, Kim BW, Euler KL, Williams L, Int. J. Pharmacogn., 32, 337 (1994)

[30] Behpour M, Ghoreishi SM, Soltani N, Niasari MS, Corrosion Sci., 51, 1073 (2009)

[31] Tao Z, Zhang S, Li W, Hou B, Corrosion Sci., 51, 2588 (2009)

[32] Negm NA, Zaki MF, Colloids Surf. A: Physicochem. Eng. Asp., 322, 97 (2008)

[33] Rosen MJ, Surfactants and interfacial phenomena, 3rd ed., John Wiley and Sons, New York, 2004p. 144.

[34] Zana R, Levy H, Colloids Surf. A: Physicochem. Eng. Asp., 127, 229 (1997)

[35] Negm NA, Amouna SM, J. Surf. Deterg, 7(1), 23 (2004)

[36] Dreja M, Pyckhout-Hintzen W, Mays H, Tieke B, Langmuir, 15(2), 391 (1999)

[37] Bendjeriou-Sedjerari A, Derrien G, Charnay C, Zajac J, De Menorval LC, Lindheimer M, J. Colloid Interface Sci., 331(2), 281 (2009)

[38] Rosen MJ, Mathias JH, Davenport L, Langmuir, 15(21), 7340 (1999)

[39] Tsubone K, Arakawa Y, Rosen MJ, J. Colloid Interface Sci., 262(2), 516 (2003)

[40] Gad EAM, El-Sukkary MMA, Ismail DA, J. Am. Oil Chem. Soc., 74, 1 (1997)

[41] Ye Z, Zhang F, Han L, Colloids Surf. A: Physicochem. Eng. Asp., 322, 138 (2008)

[42] Negm NA, Egypt. J. Chem., 45(3), 483 (2002)

[43] Nair R, Shah A, Baluja S, Chanda S, J. Serb. Chem. Soc., 71(7), 733 (2006)

[44] Cukurovali A, Yilmaz I, Gur S, Kazaz C, Eur. J. Med. Chem., 41, 201 (2006)

[45] Negm NA, Morsy SMI, Said MM, Bioorg. Med. Chem., 13, 5921 (2005)

[46] Koch A, Clin. Microbiol. Rev., 16(4), 673 (2003)

[47] Walsh F, Amyes S, Curr. Opin. Microbiol., 7(5), 439 (2004)

[48] Chernomordik I, Kozlov MM, Zimmerberg J, J. Membr. Biol., 146, 1 (1995)

[49] Saier MH Jr., Enzymes in Metabolic Pathways: A Comparative Study of Mechanism, Structure, Evolution, and Control, Harper & Row, New York, 1987.