A Novel Bio-based Sulfonic Zwitterionic Surfactant Derived from Transgenic Soybean Oil and its Performance in Surface and Interfacial Activities

Document Type : Research Paper

Authors

1 East China University of Science and Technology, Shanghai, China

2 East China University of Science and Technology

Abstract

Bio-based surfactants have attracted increasing attention due to their renewable resources and excellent surface properties. In this study, a novel bio-based sulfonic zwitterionic surfactant (BSZS) derived from transgenic soybean oil was prepared using a simple reaction route with two steps of the amidation and quaterisation. The bio-based sulfonic zwitterionic surfactant showed a critical micelle concentration (CMC) as low as 33.34 mg/L with a surface tension of 28.50 mN/m. In addition, it also showed good performance in foamability, emulsibility, and wettability. The excellent performances indicated the great potential applications of the bio-based sulfonic surfactant from vegetable oils in both daily life and industrial fields.
Bio-based surfactants have attracted increasing attention due to their renewable resources and excellent surface properties. In this study a novel biobased sulfonic zwitterionic surfactant (BSZS) derived from genetically modified(GM) soybean oil was prepared using a simple reaction route with two steps of the amidation and quaterisation. The BSZS showed a critical micelle concentration (CMC) as low as 33.3 mg/L with a surface tension of 28.5 mN/m. In addition, it also showed good performance in foamability, emulsibility and wettability. The excellent performances indicated great potential applications of the bio-based sulfonic surfactant from vegetable oil in both daily life and industrial fields.

Keywords


REFERENCES
Small L. E., Garrison Jr P. H., Winkler W. M., Seaman S. A., and et al., “Ultra Mild Skin Cleansing Composition,” U. S. Patent, 1987, 4, 812-253.
Shah D. O. and Schchter R. S., “Improved Oil Recovery by Surfactant and Polymer Flooding (1st ed.),” Academic Press of the United Kingdom, 1997, 1-205.
Banat I. M., “Bio-surfactants Production and Possible Uses in Microbial Enhanced Oil Recovery and Oil Pollution Remediation: A Review,” Bioresource Technology, 1995, 51, 1-12.
Urum K., Grigson S., Pekdemir T., and McMenamy S., “A Comparison of the Efficiency of Different Surfactants for Removal of Crude Oil from Contaminated Soils,” Chemosphere, 2006, 62, 1403-1410.
Owoseni O., Nyankson E., Zhang Y., Adams S. J., and et al., “Release of Surfactant Cargo from Interfacially-active Halloysite Clay Nanotubes for Oil Spill Remediation,” Langmuir, 2014, 30, 13533-13541.
Foley P., Beach E. S., and Zimmerman J. B., “Derivation and Synthesis of Renewable Surfactants,” Chemical Society Reviews, 2012, 41, 1499-1518.
Sreenu M., Rao B. V., Prasad R. B. N., Sujitha P., and et al., “Synthesis, Surface and Biological Properties of Sodium N-Acyl Isoleucines,” European Journal of Lipid Science and Technology, 2014, 116, 193-206.
Rajabi F. and Luque R., “An Efficient Renewable-Derived Surfactant for Aqueous Esterification Reactions,” RSC Advances, 2014, 4, 5152-5155.
Abdelkader M. B., Azizi N., Chemli M., Chevalier Y., and et al., “Synthesis and Emulsifier Properties of a New Bio-Sourced Surfactant Based on Isosorbide,” Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2016, 492, 1-11.
Fan Z., Zhao Y., Preda F., Clacens J. M., and et al., “Preparation of Bio-Based Surfactants from Glycerol and Dodecanol by Direct Etherification,” Green Chemistry, 2015, 17, 882-892.
Huang K., Zhang P., Zhang J., Li S., Li M., and et al., “Preparation of Bio-based Epoxies Using Tung Oil Fatty Acid-Derived C21 Diacid and C22 Triacid and Study of Epoxy Properties,” Green Chemistry, 2013, 15, 2466-2475.
Negm N. A., El-Farargy A. F., Halim E. A. A., El-lboudy S., and et al., “Novel Bio-based Nonionic Surfactants: Synthesis, Surface Activity and Corrosion Inhibition Efficiency against Aluminum Alloy Dissolution in Acidic Media,” Journal of surfactants and detergents, 2014, 17, 1203-1211.
Hu J., Jin Z., Chen T.-Y., Polley J. D., and et al., “Anionic Polymerizable Surfactants from Bio-based Ω-Hydroxy Fatty Acids,” Macromolecules, 2013, 47, 113-120.
Miao S., Wang P., Su Z., and Zhang S., “Vegetable-Oil-Based Polymers as Future Polymeric Biomaterials,” Acta biomaterialia, 2014, 10, 1692-1704.
Biermann U., Bornscheuer U., Meier M. A., Metzger J. O., and et al., “Oils and Fats as Renewable Raw Materials in Chemistry,” Angewandte Chemie International Edition, 2011, 50, 3854-3871.
Wu M. H., Wan L. Z., and Zhang Y. Q., “A Novel Sodium N-Fatty Acyl Amino Acid Surfactant Using Silkworm Pupae as Stock Material,” Scientific reports, 2014, 4, 4428.
Zhang Q. Q., Cai B. X., Xu W. J., Gang H. Z., and et al., “The Rebirth of Waste Cooking Oil to Novel Bio-Based Surfactants,” Scientific reports, 2015, 5.
Zhang Q. Q., Cai B. X., Xu W. J., Gang H. Z., and et al., “Novel Zwitterionic Surfactant Derived from Castor Oil and Its Performance Evaluation for Oil Recovery,” Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2015, 483, 87-95.
Feng D., Zhang Y., Chen Q., Wang J., et al., “Synthesis and Surface Activities of Amidobetaine Surfactants with Ultra-Long Unsaturated Hydrophobic Chains,” Journal of surfactants and detergents, 2012, 15, 657-661.
Wang H., Gang H., Ye R., and Mu B., “Interaction between Bio-surfactant Surfactin and Cationic Surfactant Cetyl Trimethyl Ammonium Bromide in Mixed Micelle,” Colloid and Polymer Science, 2014, 292, 3169-3176.
Lu T., Lan Y., Liu C., Huang J. et al., “Surface Properties, Aggregation Behavior and Micellization Thermodynamics of a Class of Gemini Surfactants with Ethyl Ammonium Headgroups,” Journal of colloid and interface science, 2012, 377, 222-230.
Eastoe J., Nave S., Downer A., Paul A. et al., “Adsorption of Ionic Surfactants at the Air-Solution Interface,” Langmuir, 2000, 16, 4511-4518.
Zhang Q. Q., Cai B. X., Gang H. Z., Yang S. Z., et al., “A Family of Novel Bio-Based Zwitterionic Surfactants Derived from Oleic Acid,” RSC Advances, 2014, 4, 38393-38396.
Nedyalkov M., Alexandrova L., Platikanov D., Levecke B., et al., “Wetting Properties of Aqueous Solutions of Hydrophobically Modified Inulin Polymeric Surfactant,” Colloid and Polymer Science, 2008, 286, 713-719.
Sreenu M., Rao B. V. S. K., Prasad R. B. N., Sujitha P. et al., “Synthesis, Surface and Biological Properties of Sodium N-Acyl Isoleucines,” European Journal of Lipid Science and Technology, 2014, 116, 193-206.
Sreenu M., Nayak R. R., Prasad R. B. N., and Sreedhar B., “Synthesis, Surface and Micellar Properties of Sodium N-Oleoyl Amino Acids,” Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2014, 449, 74-81.
Ng W., Rana D., Neale G., and Hornof V., “Physicochemical Behavior of Mixed Surfactant Systems: Petroleum Sulfonate and Lignosulfonate,” Journal of applied polymer science, 2003, 88, 860-865.
Dai X., Suo J., Duan X., Bai Z., and et al., “A Study of the Technical Route of the Synthesis of Alkylbenzenes for Use as an Oil Displacement Agent,” Journal of surfactants and detergents, 2008, 11, 111-115.
Chen L., Zhang G., Ge J., Jiang P., and et al., “Research of the Heavy Oil Displacement Mechanism by Using Alkaline/Surfactant Flooding System,” Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2013, 434, 63-71.
Tang M., Zhang G., Ge J., Jiang P., and et al., “Investigation into the Mechanisms of Heavy Oil Recovery by Novel Alkaline Flooding,” Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2013, 421, 91-100.
Zhao X., Bai Y., Wang Z., Shang X., and et al., “Low Interfacial Tension Behavior between Organic Alkali/Surfactant/Polymer System and Crude Oil,” Journal of Dispersion Science and Technology, 2013, 34, 756-763.
Liu Q., Dong M., Yue X., and Hou J., “Synergy of Alkali and Surfactant in Emulsification of Heavy Oil in Brine,” Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2006, 273, 219-228.
Qiao W., Li J., Zhu Y., and Cai H., “Interfacial Tension Behavior of Double Long-Chain 1, 3, 5-Triazine Surfactants for Enhanced Oil Recovery,” Fuel, 2012, 96, 220-225.
Fekarcha L. and Tazerouti A., “Surface Activities, Foam Properties, HLB, and Krafft Point of Some N-Alkanesulfonates (C14–C18) with Different Isomeric Distributions,” Journal of surfactants and detergents, 2012, 15, 419-431.