D-Optimal Design Optimization for Esterification of Palm Fatty Acids Distillate with Polyhydric Alcohols for Biolubricants Production

Document Type : Research Article

Authors

Department of Chemical Sciences, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, MALAYSIA

Abstract

Plant-based bio-lubricant is crucial to be developed and adopted by many industries.  This is due to the presence of toxicity risk, climate change, energy security as well green-environmental approach issues. The utilization of palm oil processing industries' by-product, palm fatty acid distillate (PFAD-based bio-lubricants is one way of a green environment approach. A synthesis of polyol esters based on PFAD for bio-lubricants was carried out. The esterification of PFAD with high-degree polyhydric alcohols trimethylolpropane (TMP), di-trimethylopropane (di-TMP), pentaerythritol (PE), and di-pentaerythritol (Di-PE) in the presence of sulphuric acid (H2SO4) catalyst have been performed. The optimization of the esterification reaction process was evaluated using a D-optimal design based on three reaction parameters; H2SO4 concentration (%) for the catalyst, esterification time (h), and esterification temperature (°C).  The chemical structure of the synthesized polyol esters was characterized and confirmed by using FT-IR and NMR (1H and 13C) spectroscopies. The results showed that PFAD-based polyesters of PFAD-TMP ester successfully produced high yields of 93% compared to others.  The synthesized PFAD-based polyesters showed good lubrication properties with high viscosity indices in the range of 141-187, pour points (-5 to 5 ºC), flash points (230-360 ºC), and oxidative stability temperature (188-301 °C), respectively. The ester functional group present in the chemical structure of PFAD-based polyesters showed a positive impact on the lubrication properties. The study indicated that PFAD-based polyesters are plausible to be used in industrial bio-lubricant applications.

Keywords

Main Subjects

References

[1] Parveez G.K.A., Hishamuddin E., Loh S.K., Ong-Abdullah M., Salleh K.M., Bidin M.N.I.Z., Sundram S., Hasan Z.A.A., Idris Z., Oil Palm Economic Performance in Malaysia and R&D Progress in 2019, J. Oil Palm Res., 32: 159-190 (2020).
[2] Ahmed W.A., Salih N., Salimon J., Synthesis, Characterization, Tribological and Rheological Properties of Di (2-Butyloctyl) Dicarboxylate Esters for Environmentally Friendly Biolubricant Applications, Biointerface Res. Appl. Chem., 13: 278 (2023). 
[3] Samidin S., Salih N., Salimon J., Synthesis and Characterization of Trimethylolpropane Based Esters as Green Biolubricant Basestock, Biointerface Res. Appl. Chem., 11: 13638–13651 (2021).
[4] Lye Y.N., Salih N., Salimon J., Optimization of Partial Epoxidation on Jatropha curcas Oil Based Methyl Linoleate Using Urea-hydrogen Peroxide a 4nd Methyltrioxorhenium Catalyst,  Appl. Sci. Eng. Prog., 14, 89-99 (2021).
[5] Jumaah, M.A., Khaleel, F.L., Salih, N. et al. Synthesis of Tri, Tetra, and Hexa-Palmitate Polyol Esters from Malaysian Saturated Palm Fatty Acid Distillate for Biolubricant Production, Biomass Conv. Bioref. https://doi.org/10.1007/s13399-022-0251.7-x (2022).
[6] Cecilia J.A., Plata D.B., Saboya R.M.A., de Luna F.M.T., Cavalcante C.L., Rodríguez-Castellón E., An Overview of the Biolubricant Production Process: Challenges and Future Perspectives, Processes, 8: 1–24 (2020).
[7] Salih N., Salimon J.,  A Review on New Trends, Challenges and Prospects of Ecofriendly Friendly Green Food-Grade Biolubricants, Bioiterface Res. Appl. Chem., 12: 1185 - 1207 (2022).
[8] Jumaah M.A., Salih N., Salimon J., D-Optimal Design Optimization of Unsaturated Palm, Comptes Rendus Chimie, 25: 93-112 (2022).
[9] Menkiti M.C., Anaehobi H.C., Onukwuli O.D., Kinetics and Parametric Study of Transesterification Synthesis of Biolubricant from Melon-Based Methyl Esters, Biofuels., 7: 489-500 (2016).
[10] Liu H., Liu H., Zhu C., Parker R.G., Effects of Lubrication on Gear Performance: A Review, Mech. Mach. Theory., 145: 103701 (2020).
[11] Aziz N.A.M., Yunus, R., Hamid, H.A., Ghassan A.A.K., Omar R., Rashid U., Abbas Z., An Acceleration of Microwave-Assisted Transesterification of Palm Oil-Based Methyl Ester into Trimethylolpropane Ester, Sci. Rep. 10: 19652 (2020).
[12] Fadzel F.M., Salimon J., Derawi D., Biolubricant Production from Palm Stearin Fatty Acids and Pentaerythritol, Malaysian J. Chem., 21: 50-63 (2019).
[13] Nor N.M., Derawi D., Salimon J., Esterification and Evaluation of Palm Oil as Biolubricant Base Stock, Malaysian J. Chem., 21: 28–35 (2019).
[14] Fernandes K., Papadaki A., da Silva J.A.C., Fernandez-Lafuente R., Enzymatic Esterification of Palm Fatty-Acid Distillate for the Production of Polyol Esters with Biolubricant Properties, Ind. Crops Prod., 116: 90-96 (2018).
[15] Jumaah M.A., Yusoff M.F.M., Salimon J., Bahadi M., Physical Characteristic of Plam Fatty Acid Distillate, J. Chem. Pharm. Sci., 12: 1-5 (2019).
[16] Palmquist D.L., Palm Fats for Livestock Feeding, Palm Oil Development, 40: 10-16 (2005).
[17] Handojo L.A., Indarto A., Shofinita D., Saadi M.R., Yulistia  D., Hasyyati F.I., Calcium Soap from Palm Fatty Acid Distillate for Ruminant Feed: The Influence of Initial Mixing Temperature. IOP Conf. Ser.: Mater. Sci. Eng., 543: 012017 (2019).
[18] Top A.G.M., Production and Utilization of Palm Fatty Acid Distillate (PFAD), Lipid Technol., 22:11-13 (2010).
[19] Vernon F.M.J., “Firelighter with Palm Fatty Acid Distillate”, Standard Brands (UK) Ltd U.S. Patent Application 15/749,703, 2018.
[20] Kapor N.Z.A., Maniam G.P., Rahim M.H.A., Yusoff M.M., Palm Fatty Acid Distillate as a Potential Source for Biodiesel Production - A Review,
J. Clean. Prod., 143: 1-9 (2017).
[21] Akinfalabi S.-I., Rashid U., Shean T.Y.C., Nehdi I.A., Sbihi H.M., Gewik M.M., Esterification of Palm Fatty Acid Distillate for Biodiesel Production Catalyzed by Synthesized Kenaf Seed Cake-Based Sulfonated Catalyst, Catalysts, 9: 482 (2019).
[22] Teo K.T., Hassan A., Gan S.N., UV-Curable Urethane Acrylate Resin from Palm Fatty Acid Distillate, Polymers, 10: 1374 (2018).
[23] Papadaki A., Fernandes K.V., Chatzifragkou A., Aguieiras E.C.G., da Silva J. A. C., Roberto F.-L., Seraphim P., Apostolis K., Denise M.G.F., Bioprocess Development for Biolubricant Production Using Microbial Oil Derived via Fermentation from Confectionery Industry Wastes., Bioresour Technol., 267: 311-318 (2018).
[24] Deshmane V.G., Gogate P.R., Pandit A.B., Ultrasound Assisted Synthesis of Isopropyl Esters from Palm Fatty Acid Distillate, Ultrasonics Sonochem., 16: 345-350 (2009).
[25] Lokman I.M., Goto M., Rashid U., Taufiq-Yap Y.H., Sub-and Supercritical Esterification of Palm Fatty Acid Distillate with Carbohydrate-Derived Solid Acid Catalyst, Chem. Eng. J., 284: 872-878 (2016).
[26] Ibrahim S.F., Asikin-Mijan N., Ibrahim M.L., Abdulkareem-Alsultan G., Izham S.M., Taufiq-Yap Y.H., Sulfonated Functionalization of Carbon Derived Corncob Residue via Hydrothermal Synthesis Route for Esterification of Palm Fatty Acid Distillate, Energy Convers. Manag., 210: 112698 (2020).
[27] Derawi D., Salimon J., Potential of Palm Olein as Green Lubricant Source: Lubrication Analysis and Chemical Characterization, Malaysian J. Anal. Sci., 18: 245–250 (2014).
[28] Koh M.Y., Tinia T.I., Idris A., Synthesis of Palm Based Biolubricant in an Oscillatory Flow Reactor (OFR), Ind. Crops Prod., 52: 567–574 (2014).
[29] Ahmed W.A., Salih N., Salimon J., Lubricity, Tribological and Rheological Properties of Green Ester Oil Prepared from Bio-Based Azelaic Acid, Asian J. Chem., 33: 1363-1369 (2021).
[30] Salih N., Salimon J., Review on Eco-Friendly Green Biolubricants from Renewable and Sustainable Plant Oil Sources, Biointerface Res. Appl. Chem., 11: 13303-13327 (2021).
[31] ASTM D-2270, “Standard Practice for Calculating Viscosity Index from Kinematic Viscosity at 40 and 100°C”, ASTM, West Conshohocken, PA, USA.
[32]  Reza M.B., Mohsen A.-P., Hamid R.S., Optimization of Mechanical Properties Using D-Optimal Factorial Design of Experiment: Electromagnetic Stir Casting Process of A357−SiC Nanocomposite, Trans. Nonferrous Met. Soc. China, 30: 1183-1194 (2020).
[33] Anthony C.A., "Optimal Design", Wiley Statistics Reference Online, John Wiley & Sons, Ltd (2015).
[34] Xu W., Wong W.K., Tan K.C., Xu J., Finding High-Dimensional D-Optimal Designs for Logistic Models via Differential Evolution, IEEE Access. 7: 7133–7146 (2019).
[35] Resit U, Roger A.L., Mark L.M., Response Surface Model Building and Multidisciplinary Optimization Using D-Optimal Designs, 7th AIAA/USAF/NASA/ISSMO Symposium on Multidisciplinary Analysis and Optimization (1998).
[36] Holm R., Jensen I.H.M., Sonnergaard J., Optimization of Self-Microemulsifying Drug Delivery Systems (SMEDDS) Using a D-Optimal Design and the Desirability Function, Drug Dev. Ind. Pharm., 32: 1025-1032 (2006).
[37] Kuram E., Ozcelik B., Bayramoglu M., Demirbas E., Simsek B.T.,  Optimization of Cutting Fluids and Cutting Parameters during End Milling by Using D-optimal Design of Experiments, J. Clean. Prod., 42: 159-166 (2013).
[38] Bahadi M., Salih N., Salimon J., D-Optimal Design Optimization for the Separation of Oleic Acid from Malaysian High Free Fatty Acid Crude Palm Oil Fatty Acids Mixture Using Urea Complex Fractionation, Appl. Sci. Eng. Prog., 14, 175–186 (2021).
[39] Bahadi M., Yusoff M.F., Salimon J., Derawi D. Optimization of Response Surface Methodology by D-Optimal Design for Alkaline Hydrolysis of Crude Palm Kernel Oil, Sains Malaysiana, 49: 29-41 (2020).
[40] Nor N.M., Salih N., Salimon J., Optimization of the Ring Opening of Epoxidized Palm Oil Using D-Optimal Design, Asian J. Chem., 33: 67–75 (2021).
[41] Grčić I., Vujević D., Koprivanac N., The Use of D-Optimal Design to Model the Effects of Process Parameters on Mineralization and Discoloration Kinetics of Fenton-Type Oxidation, Chem. Eng. J., 157: 408–419 (2010).
[42] Bahadi M., Salimon J., Derawi D., Synthesis of Di-Trimethylolpropane Tetraester-Based Biolubricant from Elaeis guineensis Kernel Oil via Homogeneous Acid Catalyzed Transesterification, Renew. Energy, 171: 981–993 (2021).
[43] Chan C.H., Tang S.W., Mohd N.K., Lim W.H., Yeong S.K., Idris Z., Tribological Behavior of Biolubricant Base Stocks and Additives, Renew. Sust. Energy Rev., 93: 145–157, 2018.
[44] Jumaah M.A., Salih N., Salimon J., Optimization for Esterification of Saturated Palm Fatty Acid Distillate By D-optimal Design Response Surface Methodology for Biolubricant Production, Turk. J. Chem., 45: 1391-1407 (2021).
[45] Nor N.M., Salih N., Salimon J., Chemically Modified Jatropha curcas Oil for Biolubricant Applications, Hem. Ind. 75: 117-128 (2021).
[46] Owuna F.J., Dabai M.U., Sokoto M.A., Dangoggo S.M., Bagudo B.U., Birnin-Yauri U.A., Hassan L.G., Sada I., Abubakar A.L., Jibrin, M.S., Chemical Modification of Vegetable Oils for the Production of Biolubricants Using Trimethylolpropane: A Review, Egypt. J. Pet. 29: 75–82 (2020).
[47] Al-Arafi N., Salih N., Salimon J., Synthesis, Characterization, Tribological and Rheological Properties of Oleyl Oleate Based Biolubricant, Egypt. J. Chem., 65: 419-433 (2022).
[48] Totten G.E., Westbrook S.R., Shah R.J., ˝Fuels and Lubricants Handbook: Technology, Properties, Performance, and Testing˝, USA, New York, ASTM International (2019).
[49] Cermak S.C., Brandon K.B., Isbell T.A., Synthesis and Physical Properties of Estolides from Lesquerella and Castor Fatty Acid Esters, Ind. Crops Prod., 23: 54-64 (2006).
[50] Encinar J.M., Nogales-Delgado S., Sánchez N., González J.F., Biolubricants from Rapeseed and Castor Oil Transesterification by Using Titanium Isopropoxide as a Catalyst: Production and Characterization, Catalysts, 10, 366 (2020).
[51] Bahadi, M., Yusoff, M.F., Salimon, J., Derawi, D., Optimization of Response Surface Methodology by D-Optimal Design for Synthesis of Food-Grade Palm Kernel Based Biolubricant, Ind. Crops Prod., 139: 111452 (2019).

Files

Share

How to cite

Statistics