Methyl Ester Sulfonate (MES) Surfactant Production from Waste Cooking Oil (WCO) with Microwave Technology
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Keywords:
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Methyl Ester Sulfonate , Microwave, Surfactant, Transesterification, Waste Cooking Oil
Abstract
Traction Energy Asia 2020 reported that 3 million kilolitres of WCO were collected in Indonesia in 2019, 1.6 million kilolitres from urban households. WCO poses risks due to common reuse or disposal. Repurposing for MES surfactant is vital. Hence, this study aims to produce an MES surfactant from WCO feedstock using NaHSO3 as a microwave-assisted reactant by observing the influence of variables such as reactant mole ratio, catalyst concentration, sulfonation reaction time, and microwave power. The adsorption method involves vacuum filtration of WCO to remove impurities, mixing with activated carbon, and settling before a second filtration. Transesterification transforms WCO into methyl ester through mixing with methoxide solution with a molar ratio of methanol to WCO of 1:9 and a 1 wet% NaOH catalyst based on WCO, followed by washing and drying. Sulfonation involves reacting methyl ester with NaHSO3 (1:1, 1:2, 1:3, 1:4) and CaO catalyst (1%, 1.5%, 2%, 2.5%). The reaction occurs in a microwave at power variations of 300, 450, 600, and 750 Watts, as well as with variations in time of 20, 30, 40, 50, and 60 minutes. After that, it ends with purifying and neutralizing to produce MES. The optimal conditions for MES production are a 1:2 molar ratio of reactants, 1.5% CaO catalyst concentration, 20 minutes, and 450 W, yielding 48.06%. MES characteristics: pale yellow color, density of 0.859 g/cm3, viscosity of 1.780 cSt, and surface tension of 32.62 dyne/cm. FTIR analysis confirms sulfonic acid groups at 1195.27 cm−1 and 1169.1 cm−1 wavelengths.
References
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Da Rosa, C. F. C., Freire, D. M. G., & Ferraz, H. C. (2015). Biosurfactant microfoam: Application in the removal of pollutants from soil. Journal of Environmental Chemical Engineering, 3(1), 89–94.
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Efiyanti, L., Indrawan, D. A., Arif, Z., Hutapea, D., & Septina, A. D. (2020). Synthesis and application of a sulfonated carbon catalyst for a hydrolysis reaction. Indonesian Journal of Science and Technology, 5(3), 410–420.
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Jesus, C. F., Alves, A. A. S., Fiuza, S. M., Murtinho, D., & Antunes, F. E. (2021). Mini-review: Synthetic methods for the production of cationic sugar-based surfactants. Journal of Molecular Liquids, 342, 117389.
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Johnson, P., Trybala, A., Starov, V., & Pinfield, V. J. (2021). Effect of synthetic surfactants on the environment and the potential for substitution by biosurfactants. Advances in Colloid and Interface Science, 288, 102340.
Karami, Z., Emam-Djomeh, Z., Mirzaee, H. A., Khomeiri, M., Mahoonak, A. S., & Aydani, E. (2015). Optimization of microwave assisted extraction (MAE) and Soxhlet extraction of phenolic compound from licorice root. Journal of Food Science and Technology, 52(6), 3242–3253.
Kulkarni, D., & Jaspal, D. (2023). Surfactants in wastewater: Development, current status and associated challenges. Materials Today: Proceedings.
Kumar, S., Shamsuddin, M. R., Farabi, M. S. A., Saiman, M. I., Zainal, Z., & Taufiq-Yap, Y. H. (2020). Production of methyl esters from waste cooking oil and chicken fat oil via simultaneous esterification and transesterification using acid catalyst. Energy Conversion and Management, 226, 113366.
Lam, S. S., Wan Mahari, W. A., Ok, Y. S., Peng, W., Chong, C. T., Ma, N. L., & Tsang, D. C. W. (2019). Microwave vacuum pyrolysis of waste plastic and used cooking oil for simultaneous waste reduction and sustainable energy conversion: Recovery of cleaner liquid fuel and techno-economic analysis. Renewable and Sustainable Energy Reviews, 115, 109359.
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Liu, C., Duan, X., Chen, Q., Chao, C., Lu, Z., Lai, Q., & Megharaj, M. (2019). Investigations on pyrolysis of microalgae Diplosphaera sp. MM1 by TG-FTIR and Py-GC/MS: Products and kinetics. Bioresource Technology, 294, 122126.
Liu, K., Y. Sun, M. Cao, J. Wang, J. R. Lu, and H. Xu (2020). Rational Design, Properties, and Applications of Biosurfactants: A Short Review of Recent Advances. Current Opinion in Colloid and Interface Science, 45; 57–67.
Mahfud, M., U. Kalsum, and V. Aswie (2020). Biodiesel Production through Catalytic Microwave In-Situ Transesterification of Microalgae (Chlorella sp.). International Journal of Renewable Energy Development, 9(1); 113–117.
Mansur, D., N. Astrini, and T. Tasrif (2007). Sodium Bisulfite as SO₃ Source for Synthesis of Methyl Ester Sulfonate Using RBD Stearin as Raw Material. IPTEK The Journal for Technology and Science, 18(4); 161–167.
Marti-Mestres, G. and F. Nielloud (2002). Emulsions in Health Care Applications - An Overview. Journal of Dispersion Science and Technology, 23(1-3); 419–439.
Masakorala, K., A. Turner, and M. T. Brown (2011). Toxicity of Synthetic Surfactants to the Marine Macroalga, Ulva lactuca. Water, Air, & Soil Pollution, 218(1); 283–291.
Masuda, M., H. Odake, K. Miura, K. Ito, K. Yamada, and K. Oba (1993). Biodegradation of 2-Sulfonatofatty Acid Methyl Ester (α-SFMe). II. Biodegradation Pathways of α-SFMe. Progress in Colloid and Polymer Science, 42; 206–213.
Masyithah, Z., E. K. Sinaga, P. A. Gultom, and A. Ginting (2020). Synthesis of N-Acyl Arginine Surfactants from Tetradecanol and Arginine Using Tert-Amyl Alcohol. ARPN Journal of Engineering and Applied Sciences, 15(23); 2770–2777. Retrieved from www.arpnjournals.com.
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Mi, J., J. Cheng, K. H. Ng, and N. Yan (2024). Biomass to Green Surfactants: Microwave-Assisted Transglycosylation of Wheat Bran for Alkyl Glycosides Production. Bioresource Technology, 401; 130738.
Nollet, M., H. Boulghobra, E. Calligaro, and J. D. Rodier (2019). An Efficient Method to Determine the Hydrophile-Lipophile Balance of Surfactants Using the Phase Inversion Temperature Deviation of CiEj/n-Octane/Water Emulsions. International Journal of Cosmetic Science, 41(1); 99–108.
Ohbu Fujiwara, Y., K. M. Abe, K. M. Ohbu Fujiwara, and Y. Abe (1998). Physicochemical Properties of α-Sulfonated Fatty Acid Esters. Progress in Colloid and Polymer Science, 109; 206–213.
Pan, F., Z. Li, H. Gong, J. T. Petkov, and J. R. Lu (2018). Membrane-Lytic Actions of Sulphonated Methyl Ester Surfactants and Implications to Bactericidal Effect and Cytotoxicity. Journal of Colloid and Interface Science, 531; 18–27.
Panda, A., A. Kumar, S. Mishra, and S. S. Mohapatra (2020). Soapnut: A Replacement of Synthetic Surfactant for Cosmetic and Biomedical Applications. Sustainable Chemistry and Pharmacy, 17; 100297.
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Qadariyah, L. (2021). The Effect of Reaction Time and Temperature on the Synthesis of Methyl Ester Sulfonate Surfactant from Palm Oil as a Feedstock Using Microwave-Assisted Heating. AJCHE, 16(6); e63786.
Qadariyah, L., S. Sahila, C. Sirait, C. P. E. Purba, D. S. Bhuana, and M. Mahfud (2022). Surfactant Production of Methyl Ester Sulfonate from Virgin Coconut Oil Using Aluminum Oxide with Microwave Assistance. International Journal of Technology, 13(2); 378–388.
Roduner, E. (2014). Understanding Catalysis. Chemical Society Reviews, 43(24); 8226–8239.
Sahila, S., L. Qadariyah, and M. Mahfud (2021). The Study on Factors Affecting the Synthesis of Methyl Ester Sulfonate from Palm Oil Using CaO Catalyst with Microwave-Assisted. Journal of Physics: Conference Series, 1845(1); 012004.
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Sashikesh, G., P. Anushkkaran, Y. Praveena, M. Arumukham, V. Kugamoorthy, and V. Kandasamy (2023). A Comparison Study of the Efficacy of Different Activated Charcoals Derived from Palmyra Kernel Shell in Removing Phenolic Compounds. Current Research in Green and Sustainable Chemistry, 6; 100355.
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Sharma, K., S. S. Toor, J. Brandão, T. H. Pedersen, and L. A. Rosendahl (2021). Optimized Conversion of Waste Cooking Oil into Ecofriendly Bio-Based Polymeric Surfactant - A Solution for Enhanced Oil Recovery and Green Fuel Compatibility. Journal of Cleaner Production, 294; 126214.
Slamet, M. Ibadurrohman, and P. P. Wulandari (2017). Synthesis of Methyl Ester Sulfonate Surfactant from Crude Palm Oil as an Active Substance of Laundry Liquid Detergent. AIP Conference Proceedings, 1904(1); 020058.
Sorhie, V., Alemtoshi, B. Gogoi, B. Walling, S. A. Acharjee, and P. Bharali (2022). Role of Micellar Nanoreactors in Organic Chemistry: Green and Synthetic Surfactant Review. Sustainable Chemistry and Pharmacy, 30; 100875.
Soy, R., P. K. Kipkemboi, and K. Rop (2020). Synthesis, Characterization, and Evaluation of Solution Properties of Sesame Fatty Methyl Ester Sulfonate Surfactant. ACS Omega, 5(44); 28643–28655.
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Anggraini, I. F., Said, M., & Faizal, M. (2019). Production methyl ester sulfonate (MES) based rubber seeds as one of chemical injection solution in enhanced oil recovery (EOR) process. Science and Technology Indonesia, 4(2), 52–56.
Aswie, V., Qadariyah, L., & Mahfud, M. (2021). Pyrolysis of microalgae Chlorella sp. using activated carbon as catalyst for biofuel production. Bulletin of Chemical Reaction Engineering & Catalysis, 16(1), 205–213.
Aswie, V., Qadariyah, L., & Mahfud, M. (2022). Kinetics and characterization of microalgae biofuel by microwave-assisted pyrolysis using activated carbon. Journal of Engineering and Technological Sciences, 54(2), 318–331.
Auliya Putri, E. F., Indahyanti, E., Mardiana, D., Lestari, M. L. A. D., & Ningsih, Z. (2023). Okra mucilage extract as a co-surfactant increased the curcumin nanoemulsion stability and encapsulation efficiency. Science and Technology Indonesia, 8(3), 509–515.
Azman, N. S., Marliza, T. S., Asikin-Mijan, N., Hin, T. Y. Y., & Khairuddin, N. (2021). Production of biodiesel from waste cooking oil via deoxygenation using Ni-Mo/AC catalyst. Processes, 9(5).
Buchori, L., Labibah Ubay, D., & Syahidah, K. (2018). Biodiesel production from waste cooking oil purified with activated charcoal of salak peel. Reaktor, 18(3), 149–154.
Corin, K. C., & O’Connor, C. T. (2014). A proposal to use excess Gibbs energy rather than HLB number as an indicator of the hydrophilic-lipophilic behavior of surfactants. Minerals Engineering, 58, 17–21.
Da Rosa, C. F. C., Freire, D. M. G., & Ferraz, H. C. (2015). Biosurfactant microfoam: Application in the removal of pollutants from soil. Journal of Environmental Chemical Engineering, 3(1), 89–94.
Dolganova, I., Dolganov, I., Ivashkina, E., Zykova, A., & Sladkov, D. (2024). Studying the alkylbenzenes sulfonation process using the mathematical model considering the mass transfer. South African Journal of Chemical Engineering, 48, 196–203.
Drakontis, C. E., & Amin, S. (2020). Biosurfactants: Formulations, properties, and applications. Current Opinion in Colloid and Interface Science, 48, 77–90.
Dudley, G. B., Richert, R., & Stiegman, A. E. (2015). On the existence of and mechanism for microwave-specific reaction rate enhancement. Chemical Science, 6, 2144–2152.
Efiyanti, L., Indrawan, D. A., Arif, Z., Hutapea, D., & Septina, A. D. (2020). Synthesis and application of a sulfonated carbon catalyst for a hydrolysis reaction. Indonesian Journal of Science and Technology, 5(3), 410–420.
Ghaedrahmati, A., Jafarian, H., Khani Moghanaki, S., & Eivani, A. R. (2023). On the normal and inverse Portevin–Le Chatelier behavior in hot rolled Inconel 617 superalloy. Journal of Materials Research and Technology, 26, 445–461.
Hariani, P. L., Riyanti, F., & Fadilah, A. (2016). The influence of time reaction to characteristic of methyl ester sulfonate from seed oil ketapang. Indonesian Journal of Fundamental and Applied Chemistry, 1(1), 14–18.
Hill, K. (2001). Fats and oils as oleochemical raw materials. Journal of Oleo Science, 50(5), 433–444.
Hingu, S. M., Gogate, P. R., & Rathod, V. K. (2010). Synthesis of biodiesel from waste cooking oil using sonochemical reactors. Ultrasonics Sonochemistry, 17(5), 827–832.
Huang, D., Xu, H., Jacob, B., Ma, R., Yuan, S., Zhang, L., & Cheng, Z. (2020). Microwave-assisted preparation of two-dimensional amphiphilic nanoplate herding surfactants for offshore oil spill treatment. Journal of Loss Prevention in the Process Industries, 66, 104213.
Iman, N., Rahman, A., & Nurhaeni, D. (2016). Synthesis of methyl ester sulfonic (MES) from methyl laurate. Kovalen, 2(2), 54–66.
Ivankovic, T., Hrenovic, J., & Gudelj, I. (2009). Toxicity of commercial surfactants to phosphate-accumulating bacterium. Acta Chimica Slovenica, 56(4), 888–895.
Jahan, R., Bodratti, A. M., Tsianou, M., & Alexandridis, P. (2020). Biosurfactants, natural alternatives to synthetic surfactants: Physicochemical properties and applications. Advances in Colloid and Interface Science, 275, 102061.
Jesus, C. F., Alves, A. A. S., Fiuza, S. M., Murtinho, D., & Antunes, F. E. (2021). Mini-review: Synthetic methods for the production of cationic sugar-based surfactants. Journal of Molecular Liquids, 342, 117389.
Jin, Y., Tian, S., Guo, J., Ren, X., Li, X., & Gao, S. (2016). Synthesis, characterization and exploratory application of anionic surfactant fatty acid methyl ester sulfonate from waste cooking oil. Journal of Surfactants and Detergents, 19(3), 467–475.
Johnson, P., Trybala, A., Starov, V., & Pinfield, V. J. (2021). Effect of synthetic surfactants on the environment and the potential for substitution by biosurfactants. Advances in Colloid and Interface Science, 288, 102340.
Karami, Z., Emam-Djomeh, Z., Mirzaee, H. A., Khomeiri, M., Mahoonak, A. S., & Aydani, E. (2015). Optimization of microwave assisted extraction (MAE) and Soxhlet extraction of phenolic compound from licorice root. Journal of Food Science and Technology, 52(6), 3242–3253.
Kulkarni, D., & Jaspal, D. (2023). Surfactants in wastewater: Development, current status and associated challenges. Materials Today: Proceedings.
Kumar, S., Shamsuddin, M. R., Farabi, M. S. A., Saiman, M. I., Zainal, Z., & Taufiq-Yap, Y. H. (2020). Production of methyl esters from waste cooking oil and chicken fat oil via simultaneous esterification and transesterification using acid catalyst. Energy Conversion and Management, 226, 113366.
Lam, S. S., Wan Mahari, W. A., Ok, Y. S., Peng, W., Chong, C. T., Ma, N. L., & Tsang, D. C. W. (2019). Microwave vacuum pyrolysis of waste plastic and used cooking oil for simultaneous waste reduction and sustainable energy conversion: Recovery of cleaner liquid fuel and techno-economic analysis. Renewable and Sustainable Energy Reviews, 115, 109359.
Lin, C. S. K., Pfaltzgraff, L. A., Herrero-Davila, L., Mubofu, E. B., Abderrahim, S., Clark, J. H., & Luque, R. (2013). Food waste as a valuable resource for the production of chemicals, materials and fuels: Current situation and global perspective. Energy and Environmental Science, 6(2), 426–464.
Liu, C., Duan, X., Chen, Q., Chao, C., Lu, Z., Lai, Q., & Megharaj, M. (2019). Investigations on pyrolysis of microalgae Diplosphaera sp. MM1 by TG-FTIR and Py-GC/MS: Products and kinetics. Bioresource Technology, 294, 122126.
Liu, K., Y. Sun, M. Cao, J. Wang, J. R. Lu, and H. Xu (2020). Rational Design, Properties, and Applications of Biosurfactants: A Short Review of Recent Advances. Current Opinion in Colloid and Interface Science, 45; 57–67.
Mahfud, M., U. Kalsum, and V. Aswie (2020). Biodiesel Production through Catalytic Microwave In-Situ Transesterification of Microalgae (Chlorella sp.). International Journal of Renewable Energy Development, 9(1); 113–117.
Mansur, D., N. Astrini, and T. Tasrif (2007). Sodium Bisulfite as SO₃ Source for Synthesis of Methyl Ester Sulfonate Using RBD Stearin as Raw Material. IPTEK The Journal for Technology and Science, 18(4); 161–167.
Marti-Mestres, G. and F. Nielloud (2002). Emulsions in Health Care Applications - An Overview. Journal of Dispersion Science and Technology, 23(1-3); 419–439.
Masakorala, K., A. Turner, and M. T. Brown (2011). Toxicity of Synthetic Surfactants to the Marine Macroalga, Ulva lactuca. Water, Air, & Soil Pollution, 218(1); 283–291.
Masuda, M., H. Odake, K. Miura, K. Ito, K. Yamada, and K. Oba (1993). Biodegradation of 2-Sulfonatofatty Acid Methyl Ester (α-SFMe). II. Biodegradation Pathways of α-SFMe. Progress in Colloid and Polymer Science, 42; 206–213.
Masyithah, Z., E. K. Sinaga, P. A. Gultom, and A. Ginting (2020). Synthesis of N-Acyl Arginine Surfactants from Tetradecanol and Arginine Using Tert-Amyl Alcohol. ARPN Journal of Engineering and Applied Sciences, 15(23); 2770–2777. Retrieved from www.arpnjournals.com.
Maurad, Z. A., R. Ghazali, P. Siwayanan, Z. Ismail, and S. Ahmad (2006). Alpha-Sulfonated Methyl Ester as an Active Ingredient in Palm-Based Powder Detergents. Journal of Surfactants and Detergents, 9(2); 161–167.
Mi, J., J. Cheng, K. H. Ng, and N. Yan (2024). Biomass to Green Surfactants: Microwave-Assisted Transglycosylation of Wheat Bran for Alkyl Glycosides Production. Bioresource Technology, 401; 130738.
Nollet, M., H. Boulghobra, E. Calligaro, and J. D. Rodier (2019). An Efficient Method to Determine the Hydrophile-Lipophile Balance of Surfactants Using the Phase Inversion Temperature Deviation of CiEj/n-Octane/Water Emulsions. International Journal of Cosmetic Science, 41(1); 99–108.
Ohbu Fujiwara, Y., K. M. Abe, K. M. Ohbu Fujiwara, and Y. Abe (1998). Physicochemical Properties of α-Sulfonated Fatty Acid Esters. Progress in Colloid and Polymer Science, 109; 206–213.
Pan, F., Z. Li, H. Gong, J. T. Petkov, and J. R. Lu (2018). Membrane-Lytic Actions of Sulphonated Methyl Ester Surfactants and Implications to Bactericidal Effect and Cytotoxicity. Journal of Colloid and Interface Science, 531; 18–27.
Panda, A., A. Kumar, S. Mishra, and S. S. Mohapatra (2020). Soapnut: A Replacement of Synthetic Surfactant for Cosmetic and Biomedical Applications. Sustainable Chemistry and Pharmacy, 17; 100297.
Perkins, W. S. (1998). Surfactants - A Primer. ATI - Dyeing, Printing and Finishing, 27; 51–54.
Permadani, R. L., M. Ibadurrohman, and Slamet (2018). Utilization of Waste Cooking Oil as Raw Material for Synthesis of Methyl Ester Sulfonates (MES) Surfactant. IOP Conference Series: Earth and Environmental Science, 105(1); 012036.
Qadariyah, L. (2021). The Effect of Reaction Time and Temperature on the Synthesis of Methyl Ester Sulfonate Surfactant from Palm Oil as a Feedstock Using Microwave-Assisted Heating. AJCHE, 16(6); e63786.
Qadariyah, L., S. Sahila, C. Sirait, C. P. E. Purba, D. S. Bhuana, and M. Mahfud (2022). Surfactant Production of Methyl Ester Sulfonate from Virgin Coconut Oil Using Aluminum Oxide with Microwave Assistance. International Journal of Technology, 13(2); 378–388.
Roduner, E. (2014). Understanding Catalysis. Chemical Society Reviews, 43(24); 8226–8239.
Sahila, S., L. Qadariyah, and M. Mahfud (2021). The Study on Factors Affecting the Synthesis of Methyl Ester Sulfonate from Palm Oil Using CaO Catalyst with Microwave-Assisted. Journal of Physics: Conference Series, 1845(1); 012004.
Sakamoto, K., R. Y. Lochhead, H. I. Maibach, and Y. Yamashita (2017). Cosmetic Science and Technology: Theoretical Principles and Applications. Elsevier, second edition.
Sashikesh, G., P. Anushkkaran, Y. Praveena, M. Arumukham, V. Kugamoorthy, and V. Kandasamy (2023). A Comparison Study of the Efficacy of Different Activated Charcoals Derived from Palmyra Kernel Shell in Removing Phenolic Compounds. Current Research in Green and Sustainable Chemistry, 6; 100355.
Scott, M. J. and M. N. Jones (2000). The Biodegradation of Surfactants in the Environment. Biochimica et Biophysica Acta, 1508(1); 235–251. Retrieved from www.elsevier.com/locate/bba.
Sharma, K., S. S. Toor, J. Brandão, T. H. Pedersen, and L. A. Rosendahl (2021). Optimized Conversion of Waste Cooking Oil into Ecofriendly Bio-Based Polymeric Surfactant - A Solution for Enhanced Oil Recovery and Green Fuel Compatibility. Journal of Cleaner Production, 294; 126214.
Slamet, M. Ibadurrohman, and P. P. Wulandari (2017). Synthesis of Methyl Ester Sulfonate Surfactant from Crude Palm Oil as an Active Substance of Laundry Liquid Detergent. AIP Conference Proceedings, 1904(1); 020058.
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Authors
Qadariyah, L., Ryvalda, D. S. ., Aditama, N. Y., Aswie, V., & Mahfud, M. (2024). Methyl Ester Sulfonate (MES) Surfactant Production from Waste Cooking Oil (WCO) with Microwave Technology. Science and Technology Indonesia, 9(4), 929–940. https://doi.org/10.26554/sti.2024.9.4.929-940
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