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Synthesis of tri, tetra, and hexa-palmitate polyol esters from Malaysian saturated palm fatty acid distillate for biolubricant production

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Abstract

Palm fatty acid distillate is a processing by-product resulting from physical refining of crude palm oil products. Producing renewable fuels and biodegradable ester-based biolubricants using saturated palm fatty acid distillate (SFA) is one of environmentally friendly and an efficient way to reuse such by-product for the production of feasible high-end products. This study was carried out to synthesize and determine the optimal conditions for the esterification of Malaysian SFA with high degree polyhydric alcohols (trimethylolpropane, TMP; di-trimethylolpropane, Di-TMP; pentaerythritol, PE; and di-pentaerythritol, Di-PE) in the presence of sulfuric acid as catalyst. The esterification reaction parameters involved such as amount of catalyst, effect of reaction temperature (°C) and time (h), and effect of different alcohols, and molar ratio used was investigated. The results showed that the ester yield percentages varied with the corresponding reaction parameters and chemical structure of the alcohol used. The resultant esters with small-branched hydrocarbon chain alcohol produced the highest yield percentage for the SFA-TMP tri-ester (89 ± 3%) followed by the SFA-Di-TMP tetra-ester (87 ± 4%), SFA-PE tetra-ester (83 ± 5%), and SFA-Di-PE hexa-ester (77 ± 4%), respectively. The results showed the reaction temperature has more significant effect on the esterification reaction yield as compared to other parameters. The lubrication properties of the synthesized polyol esters indicated their appropriateness to be used as grease and bearing lubricant application.

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References

  1. Tulashie SK, Kotoka F (2020) The potential of castor, palm kernel, and coconut oils as biolubricant base oil via chemical modification and formulation. Therm Sci Eng Prog 16:100480. https://doi.org/10.1016/j.tsep.2020.100480

    Article  Google Scholar 

  2. Ahmed WA, Salih N, Salimon J (2021) Lubricity, tribological and rheological properties of green ester oil prepared from bio-based azelaic acid. Asian J Chem 33:1363–1369. https://doi.org/10.14233/ajchem.2021.23209

    Article  Google Scholar 

  3. Salih N, Salimon J (2022) A review on new trends, challenges and prospects of ecofriendly friendly green food-grade biolubricants. Biointerface Res Appl Chem 12:1185–1207. https://doi.org/10.33263/BRIAC121.11851207

    Article  Google Scholar 

  4. Afifah AN, Syahrullail S, Azlee NIW, Sidik NAC, Yahya WJ, Abd Rahim E (2019) Biolubricant production from palm stearin through enzymatic transesterification method. Biochem Eng J 148:178–184. https://doi.org/10.1016/j.bej.2019.05.009

    Article  Google Scholar 

  5. Sapawe N, Hanafi MF, Samion S (2019) The use of palm oil as new alternative biolubricant for improving anti-friction and anti-wear properties. Mater today: proceed 19:1126–1135. https://doi.org/10.1016/j.matpr.2019.11.005

    Article  Google Scholar 

  6. Salih N, Salimon J (2021) A Review on eco-friendly green biolubricants from renewable and sustainable plant oil sources. Biointerface Res Appl Chem 11:13303–13327. https://doi.org/10.33263/BRIAC115.1330313327

    Article  Google Scholar 

  7. Calero J, Luna D, Sancho ED, Luna C, Bautista FM, Romero AA, Posadillo A, Berbel J, Verdugo-Escamilla C (2015) An overview on glycerol-free processes for the production of renewable liquid biofuels, applicable in diesel engines. Renew Sustain Energy Rev 42:1437–1452. https://doi.org/10.1016/j.rser.2014.11.007

    Article  Google Scholar 

  8. Nor NM, Salih N, Salimon J (2021) Optimization of the ring opening of epoxidized palm oil using D-optimal design. Asian J Chem 33:67–75. https://doi.org/10.14233/ajchem.2021.22938

    Article  Google Scholar 

  9. Mba OI, Dumont MJ, Ngadi M (2015) Palm oil: processing, characterization and utilization in the food industry - a review. Food Biosci 10:26–41. https://doi.org/10.1016/j.fbio.2015.01.003

    Article  Google Scholar 

  10. Teng S, Khong KW, Ha NC (2020) Palm oil and its environmental impacts: a big data analytics study. J Clean Prod 274:122901. https://doi.org/10.1016/j.jclepro.2020.122901

    Article  Google Scholar 

  11. Japir AA, Salih N, Salimon J (2021) Synthesis and characterization of biodegradable palm palmitic acid based bioplastic. Turkish J Chem 45:585–599. https://doi.org/10.3906/kim-2011-31

    Article  Google Scholar 

  12. Koushki M, Nahidi M, Cheraghali F (2015) Physico-chemical properties, fatty acid profile and nutrition in palm oil. Arch Adv Biosci 6:117–134. https://doi.org/10.22037/jps.v6i3.9772

    Article  Google Scholar 

  13. Ludin NA, Bakri MAM, Kamaruddin N, Sopian K, Deraman MS, Hamid NH, Asim N, Othman MY (2014) Malaysian oil palm plantation sector: exploiting renewable energy toward sustainability production. J Clean Prod 65:9–15. https://doi.org/10.1016/j.jclepro.2013.11.063

    Article  Google Scholar 

  14. Mannu A, Ferro M, Dugoni GC, Garroni S, Taras A, Mele A (2020) Response surface analysis of density and flash point in recycled waste cooking oils. Chem Data Collect 25:100329. https://doi.org/10.1016/j.cdc.2019.100329

    Article  Google Scholar 

  15. Zulkifli NWM, Azman SSN, Kalam MA, Masjuki HH, Yunus R, Gulzar M (2016) Lubricity of bio-based lubricant derived from different chemically modified fatty acid methyl ester. Tribol Int 93:555–562. https://doi.org/10.1016/j.triboint.2015.03.024

    Article  Google Scholar 

  16. Ping BTY, Yusof M (2009) Characteristics and properties of fatty acid distillates from palm oil. Oil palm bull 59:5–11

    Google Scholar 

  17. Metre AV, Nath K (2015) Super phosphoric acid catalyzed esterification of palm fatty acid distillate for biodiesel production: physicochemical parameters and kinetics. Polish J Chem Technol 17:88–96. https://doi.org/10.1515/pjct-2015-0013

    Article  Google Scholar 

  18. Jumaah MA, Yousif MFM, Salimon J, Murad B (2019) Separation of saturated and unsaturated fatty acids of palm fatty acid distilled via low-temperature methanol crystallization. Malaysian J Chem 21:8–16

    Google Scholar 

  19. Baharudin KB, Taufiq-Yap YH, Hunns J, Isaacs M, Wilson K, Derawi D (2019) Mesoporous NiO/Al-SBA-15 catalysts for solvent-free deoxygenation of palm fatty acid distillate. Micropor Mesopor Mat 276:13–22. https://doi.org/10.1016/j.micromeso.2018.09.014

    Article  Google Scholar 

  20. Haraldsson G (1984) Separation of saturated/unsaturated fatty acids. J Am Oil Chem Soc 61:219–222. https://doi.org/10.1007/BF02678772

    Article  Google Scholar 

  21. Bahadi M, Salih N, Salimon J (2021) 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. https://doi.org/10.14416/j.asep.2021.03.004

    Article  Google Scholar 

  22. Machado NT, Brunner G (1997) Separation of saturated and unsaturated fatty acids from palm fatty acids distillates in continuous multistage counter current columns with supercritical carbon dioxide as solvent: a process design methodology. Ciênc Tecnol Aliment 17:361–370

    Article  Google Scholar 

  23. Qiwen Y, Guoming Y, Haijun L (2021) Extraction and separation of unsaturated fatty acids from sunflower oil. IOP Conf Series: Earth Environ Sci 680:012063. https://doi.org/10.1088/1755-1315/680/1/012063

    Article  Google Scholar 

  24. Nor NM, Derawi D, Salimon J (2019) Esterification and evaluation of palm oil as biolubricant base stock. Malaysian J Chem 21:28–35

    Google Scholar 

  25. Nowicki J, Stańczyk D, Drabik J, Mosio-Mosiewski J, Woszczyński P, Warzała M (2016) Synthesis of fatty acid esters of selected higher polyols over homogeneous metallic catalysts. J Am Oil Chem Soc 93:973–981. https://doi.org/10.1007/s11746-016-2840-7

    Article  Google Scholar 

  26. Pavia DL, Lampman GM, Kriz GS, Vyvyan JR (2015) Introduction to spectroscopy, 5th edn. Cengage Learning Inc, USA

    Google Scholar 

  27. Polansky R, Prosr P, Vik R, Moravcova D, Pihera J (2017) Comparison of the mineral oil lifetime estimates obtained by differential scanning calorimetry, infrared spectroscopy, and dielectric dissipation factor measurements. Thermochim Acta 647:86–93. https://doi.org/10.1016/j.tca.2016.12.002

    Article  Google Scholar 

  28. Alexandri E, Ahmed R, Siddiqui H, Choudhary MI, Tsiafoulis CG, Gerothanassis IP (2017) High resolution NMR spectroscopy as a structural and analytical tool for unsaturated lipids in solution. Molecules 22:1663. https://doi.org/10.3390/molecules22101663

    Article  Google Scholar 

  29. Mortier RM, Fox MF, Orszulik S (2010) Chemistry and technology of lubricants, 3rd edn. Springer, New York

    Google Scholar 

  30. Lye YN, Salih N, Salimon J (2021) Optimization of partial epoxidation on Jatropha curcas oil based methyl linoleate using urea-hydrogen peroxide and methyltrioxorhenium catalyst. Appl Sci Eng Prog 14:89–99. https://doi.org/10.14416/j.asep.2020.12.006

    Article  Google Scholar 

  31. Jumaah MA, Salih N, Salimon J (2021) Optimization for esterification of palm fatty acid distillate based biolubricant using D-optimal design. Iran J Chem Chem Eng. https://doi.org/10.30492/IJCCE.2021.521586.4481

  32. Samidin S, Salih N, Salimon J (2021) Synthesis and characterization of trimethylolpropane based esters as green biolubricant basestock. Biointerface Res Appl Chem 11:13638–13651. https://doi.org/10.33263/BRIAC115.1363813651

    Article  Google Scholar 

  33. Nor NM, Salih N, Salimon J (2021) Chemically modified Jatropha curcas oil for biolubricant applications. Hem Ind 75:117–128. https://doi.org/10.2298/HEMIND200809009N

    Article  Google Scholar 

  34. Jumaah MA, Salih N, Salimon J (2022) Optimization process for the synthesis of polyol-oleates from Malaysian unsaturated palm fatty acid distillate. Iran J Chem Chem Eng. https://doi.org/10.30492/IJCCE.2022.526491.4617

  35. Ocholi O, Menkiti M, Auta M, Ezemagu I (2018) Optimization of the operating parameters for the extractive synthesis of biolubricant from sesame seed oil via response surface methodology. Egypt J Pet 27:265–275. https://doi.org/10.1016/j.ejpe.2017.04.001

    Article  Google Scholar 

  36. Owuna FJ, Dabai MU, Sokoto MA, Dangoggo SM, Bagudo BU, Birnin-Yauri UA, Hassan LG, Sada I, Abubakar AL, Jibrin MS (2020) Chemical modification of vegetable oils for the production of biolubricants using trimethylolpropane: a review. Egypt J Pet 29:75–82. https://doi.org/10.1016/j.ejpe.2019.11.004

    Article  Google Scholar 

  37. Totten GE, Westbrook SR, Shah RJ (2003) Fuels and lubricants handbook: technology, properties, performance, and testing New York, USA.

  38. Cermak SC, Brandon KB, Isbell TA (2006) Synthesis and physical properties of estolides from lesquerella and castor fatty acid esters. Ind Crops Prod 23:54–64. https://doi.org/10.1016/j.indcrop.2005.04.001

    Article  Google Scholar 

  39. Verma P, Dwivedi G, Behura AK, Patel DK, Verma TN, Pugazhendhi A (2020) Experimental investigation of diesel engine fuelled with different alkyl esters of karanja oil. Fuel 275:117920. https://doi.org/10.1016/j.fuel.2020.117920

    Article  Google Scholar 

  40. Warasanam S, Pengprecha S (2012) Synthesis of pour point depressant from dicarboxylic acid for biodiesel. Proceed Inter Conf Chem Process Environ Issues, Singapore 15–16:183–186

    Google Scholar 

  41. Encinar JM, Nogales-Delgado S, Sánchez N, González JF (2020) Biolubricants from rapeseed and castor oil transesterification by using titanium isopropoxide as a catalyst: production and characterization. Catalysts 10:366. https://doi.org/10.3390/catal10040366

    Article  Google Scholar 

  42. Chan CH, Tang SW, Mohd NK, Lim WH, Yeong SK, Idris Z (2018) Tribological behavior of biolubricant base stocks and additives. Renew Sust Energy Rev 93:145–157. https://doi.org/10.1016/j.rser.2018.05.024

    Article  Google Scholar 

  43. Arbain NH, Salimon J, Salih N, Ahmed WA (2022) Optimization for epoxidation of Malaysian Jatropha curcas oil based trimethylolpropane ester biolubricant. Appl Sci Eng Prog. https://doi.org/10.14416/j.asep.2021.10.009

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Funding

This project received funding from Universiti Kebangsaan Malaysia under the research grant no. GUP-2016–058 and Sime Darby Plantation Berhad through grant no. ST-2014–019.

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Authors and Affiliations

  1. Department of Petroleum Process Systems and Control Engineering, College of Petroleum Process Engineering, Tikrit University, Tikrit, Iraq

    Majd Ahmed Jumaah & Firas Layth Khaleel

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

    Nadia Salih & Jumat Salimon

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  1. Majd Ahmed Jumaah
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Contributions

Majd Ahmed Jumaah: investigation and methodology. Firas Layth Khaleel: formal data analysis and data curation. Nadia Salih: visualization, writing—original draft, and writing—review and editing. Jumat Salimon: conceptualization, funding acquisition, resources, project administration, supervision, validation, and writing—review and editing.

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Correspondence to Nadia Salih or Jumat Salimon.

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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. 14, 1919–1937 (2024). https://doi.org/10.1007/s13399-022-02517-x

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