Synthesis of eco-friendly fatty acid based zwitterionic biosurfactants from coconut oil sources and characterization of their interfacial properties

DaNan Yea; YeJin Lee; KiHo Park; JongChoo Lim

Journal of Industrial and Engineering Chemistry, Vol.97, 287-298, May, 2021

DOI10.1016/j.jiec.2021.02.012 Export Citation

Synthesis of eco-friendly fatty acid based zwitterionic biosurfactants from coconut oil sources and characterization of their interfacial properties

DaNan Yea, YeJin Lee, KiHo Park, and JongChoo Lim^†

Department of Chemical and Biochemical Engineering, Dongguk University-Seoul, 3-26 Phil-Dong, Choong-Ku, Seoul 100-715, South Korea

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In this study, three different types of fatty acid based biosurfactants were prepared from coconut oil and the successful synthesis was confirmed by using FT-IR, 1H-NMR and 13C-NMR analysis. Interfacial characteristics assessment has shown that all of the prepared FEA surfactants are excellent in surfactant activity and effective in reducing interfacial free energy. In particular, FEA-3 is found to possess good soil removal capacity and emulsification activity since the molecules of FEA-3 surfactant are more closely packed at the interface and thus more efficient at lowering the interfacial energy. Environmental compatibility tests such as biodegradability, oral toxicity, and skin/eye irritation revealed that FEA-3 surfactant is easily biodegradable, mild, non-toxic and non-irritating, suggesting that FEA-3 surfactant can be employed in detergent products formulation.

Keywords:Fatty acid based biosurfactant;Coconut oil;Environmental compatibility;Interfacial property;Detergent products formulation

[References]

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Mohamed AS, Mohamed MZ, J. Surfactants Deterg., 13, 159 (2010)
Lim JC, Kim JS, Mo DH, Lee JS, Appl. Chem. Eng., 50, 112 (2012)
Iwasaki T, Ogawa M, Esumi K, Meguro K, Langmuir, 7, 30 (1991)
Danov KD, Kralchevska SD, Kralchevsky PA, Ananthapadmanabhan KP, Lips A, Langmuir, 20(13), 5445 (2004)
Henkel M, Muller MM, Kugler JH, Lovaglio RB, Contiero J, Syldatk C, Hausmann R, Process Biochem., 47(8), 1207 (2012)
Haba E, Espuny MJ, Busquets M, Manresa A, J. Appl. Microbiol., 88(3), 379 (2000)
Vijayakumar S, Saravanan VK, Res. J. Microbiol., 10, 181 (2015)
Maag H, J. Am. Oil. Chem.’ Soc., 61, 259 (1984)
Holmberg K, Curr. Opin. Colloid Interface Sci., 6, 148 (2001)
Shin KH, Kim KW, Environ. Geochem. Health, 26, 5 (2004)
Shekhar S, Sundaramanickam A, Balasubramanian T, Crit. Rev. Environ. Sci. Technol., 45, 1522 (2015)
Ghojavand H, Vahabzadeh F, Azizmohseni F, Biotechnol. Bioprocess Eng., 16, 72 (2011)
Ilori MO, Adebusoye SA, Ojo AC, World J. Microbiol. Biotechnol., 24, 2539 (2008)
Lee SM, Lee JY, Yu HP, Lim JC, Colloids Surf. A: Physicochem. Eng. Asp., 536, 224 (2018)
Johansson I, Svensson M, Curr. Opin. Colloid Interface Sci., 6, 178 (2001)
Yea DN, Lee SM, Jo SH, Yu HY, Lim JC, J. Surfact. Deterg., 21, 541 (2018)
Lee SM, Lee JY, Yu HP, Lim JC, J. Ind. Eng. Chem., 38, 157 (2016)
Lim JC, Han DS, Colloids Surf. A: Physicochem. Eng. Asp., 389, 166 (2011)
KSM KS 2714 Testing method for biodegradability of synthetic detergent, (2007).
OECD Guideline for testing of chemicals: Acute oral toxicity (No.423), (2002).
OECD/OCDE Guideline for testing of chemicals: Acute dermal irritation/corrosion (No.404), (2015).
OECD/OCDE Guideline for testing of chemicals: Acute eye irritation/corrosion (No.405), (2015).
Miller CA, Neogi P, Interfacial phenomena: Equilibrium and Dynamic Effects, Marcel Dekker, New York, 1985.
Jiang Y, Geng T, Li Q, Li G, Ju H, J. Mol. Liq., 204, 126 (2015)
Chang H, Wang Y, Cui Y, Li G, Zhang B, Zhao X, Wei W, Colloids Surf. A: Physicochem. Eng. Asp., 500, 230 (2016)
Ju H, Jiang Y, Geng T, Wang Y, Zhang C, J. Mol. Liq., 225, 606 (2017)
Lim H, Lee S, Mo D, Lim J, Korean Chem. Eng. Res., 50(6), 969 (2012)
Kim JS, Park JS, Lim JC, Korean Chem. Eng. Res., 47(1), 31 (2009)
Negm NA, Tawfik SM, J. Ind. Eng. Chem., 20(6), 4463 (2014)
Liu X, Zhao Y, Li Q, Jiao T, Niu J, J. Mol. Liq., 216, 185 (2016)
Schroder V, Behrend O, Schubert H, J. Colloid Interface Sci., 202(2), 334 (1998)
Souilem S, Kobayashi I, Neves MA, Jlaiel L, Isoda H, Sayadi S, Nakajima M, Food Res. Int., 62, 467 (2014)
Chung DW, Lim JC, Colloids Surf. A: Physicochem. Eng. Asp., 336, 35 (2009)
Kang EK, Lee BM, Hwang HA, Lim JC, J. Ind. Eng. Chem., 17(5-6), 845 (2011)
Lim JC, Kang EK, Park JM, Kang HC, Lee BM, J. Ind. Eng. Chem., 18(4), 1406 (2012)
Lee BM, Kim JH, Kim SS, Lim JC, Appl. Chem. Eng., 23(5), 433 (2012)
Lim JC, Park JM, Park CJ, Lee BM, Colloid Polym. Sci., 291, 855 (2013)
Lim JC, Lee MC, Lim TK, Kim BJ, Colloids Surf. A: Physicochem. Eng. Asp., 446, 80 (2014)

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[1] Keller DS, Luner P, Colloids Surf. A: Physicochem. Eng. Asp., 161, 401 (2000)

[2] Mohamed AS, Mohamed MZ, J. Surfactants Deterg., 13, 159 (2010)

[3] Lim JC, Kim JS, Mo DH, Lee JS, Appl. Chem. Eng., 50, 112 (2012)

[4] Iwasaki T, Ogawa M, Esumi K, Meguro K, Langmuir, 7, 30 (1991)

[5] Danov KD, Kralchevska SD, Kralchevsky PA, Ananthapadmanabhan KP, Lips A, Langmuir, 20(13), 5445 (2004)

[6] Henkel M, Muller MM, Kugler JH, Lovaglio RB, Contiero J, Syldatk C, Hausmann R, Process Biochem., 47(8), 1207 (2012)

[7] Haba E, Espuny MJ, Busquets M, Manresa A, J. Appl. Microbiol., 88(3), 379 (2000)

[8] Vijayakumar S, Saravanan VK, Res. J. Microbiol., 10, 181 (2015)

[9] Maag H, J. Am. Oil. Chem.’ Soc., 61, 259 (1984)

[10] Holmberg K, Curr. Opin. Colloid Interface Sci., 6, 148 (2001)

[11] Shin KH, Kim KW, Environ. Geochem. Health, 26, 5 (2004)

[12] Shekhar S, Sundaramanickam A, Balasubramanian T, Crit. Rev. Environ. Sci. Technol., 45, 1522 (2015)

[13] Ghojavand H, Vahabzadeh F, Azizmohseni F, Biotechnol. Bioprocess Eng., 16, 72 (2011)

[14] Ilori MO, Adebusoye SA, Ojo AC, World J. Microbiol. Biotechnol., 24, 2539 (2008)

[15] Lee SM, Lee JY, Yu HP, Lim JC, Colloids Surf. A: Physicochem. Eng. Asp., 536, 224 (2018)

[16] Johansson I, Svensson M, Curr. Opin. Colloid Interface Sci., 6, 178 (2001)

[17] Yea DN, Lee SM, Jo SH, Yu HY, Lim JC, J. Surfact. Deterg., 21, 541 (2018)

[18] Lee SM, Lee JY, Yu HP, Lim JC, J. Ind. Eng. Chem., 38, 157 (2016)

[19] Lim JC, Han DS, Colloids Surf. A: Physicochem. Eng. Asp., 389, 166 (2011)

[20] KSM KS 2714 Testing method for biodegradability of synthetic detergent, (2007).

[21] OECD Guideline for testing of chemicals: Acute oral toxicity (No.423), (2002).

[22] OECD/OCDE Guideline for testing of chemicals: Acute dermal irritation/corrosion (No.404), (2015).

[23] OECD/OCDE Guideline for testing of chemicals: Acute eye irritation/corrosion (No.405), (2015).

[24] Miller CA, Neogi P, Interfacial phenomena: Equilibrium and Dynamic Effects, Marcel Dekker, New York, 1985.

[25] Jiang Y, Geng T, Li Q, Li G, Ju H, J. Mol. Liq., 204, 126 (2015)

[26] Chang H, Wang Y, Cui Y, Li G, Zhang B, Zhao X, Wei W, Colloids Surf. A: Physicochem. Eng. Asp., 500, 230 (2016)

[27] Ju H, Jiang Y, Geng T, Wang Y, Zhang C, J. Mol. Liq., 225, 606 (2017)

[28] Lim H, Lee S, Mo D, Lim J, Korean Chem. Eng. Res., 50(6), 969 (2012)

[29] Kim JS, Park JS, Lim JC, Korean Chem. Eng. Res., 47(1), 31 (2009)

[30] Negm NA, Tawfik SM, J. Ind. Eng. Chem., 20(6), 4463 (2014)

[31] Liu X, Zhao Y, Li Q, Jiao T, Niu J, J. Mol. Liq., 216, 185 (2016)

[32] Schroder V, Behrend O, Schubert H, J. Colloid Interface Sci., 202(2), 334 (1998)

[33] Souilem S, Kobayashi I, Neves MA, Jlaiel L, Isoda H, Sayadi S, Nakajima M, Food Res. Int., 62, 467 (2014)

[34] Chung DW, Lim JC, Colloids Surf. A: Physicochem. Eng. Asp., 336, 35 (2009)

[35] Kang EK, Lee BM, Hwang HA, Lim JC, J. Ind. Eng. Chem., 17(5-6), 845 (2011)

[36] Lim JC, Kang EK, Park JM, Kang HC, Lee BM, J. Ind. Eng. Chem., 18(4), 1406 (2012)

[37] Lee BM, Kim JH, Kim SS, Lim JC, Appl. Chem. Eng., 23(5), 433 (2012)

[38] Lim JC, Park JM, Park CJ, Lee BM, Colloid Polym. Sci., 291, 855 (2013)

[39] Lim JC, Lee MC, Lim TK, Kim BJ, Colloids Surf. A: Physicochem. Eng. Asp., 446, 80 (2014)