Optimization for esterification of saturated palm fatty acid distillate by D-optimal design response surface methodology for biolubricant production

Optimization for esterification of saturated palm fatty acid distillate by D-optimal design response surface methodology for biolubricant production

This work presents a synthesis of palm fatty acid distillate (PFAD)-based esters to produce biolubricant oils through the esterification reaction between saturated palm fatty acid distillate (SFA-PFAD) with different types of high degree polyhydric alcohols such as trimethylolpropane (TMP), di-trimethylolpropane (Di-TMP), pentaerythritol (PE), and di-pentaerythritol (Di-PE) in the presence of sulfuric acid as catalyst. The chemical structures of synthesized SFA PFAD-based esters were characterized and confirmed by using FTIR, NMR $(^1H and ^{13}C)$ spectroscopies and GC-FID chromatography. The FTIR spectra of SFA PFAD-based ester products clearly showed the peaks of C=O and C–O of ester group at $1732–1740 cm^{−1} and at 1239–1162 cm^{−1}$, respectively. Furthermore, $^1H$ NMR spectra confirmed the proton chemical shift $(-CH_2-O-)$ of the ester group at 3.80–4.01 ppm. The 13C NMR spectra confirmed the carbon chemical shifts of ester carbonyl signals at 171.09–174.07 ppm and secondary carbons (CH2-C = O) at 40.57–42.44 ppm. The results showed that the optimum conditions for the esterification of SFA-TMP was obtained at acid catalysts of 5%, esterification time and temperature of 6 h and 150 °C, respectively. The results have shown the ester products yields have been significantly increased up to 93% with selectivity of 99% SFA-TMP tri-ester after the optimization process by using D-optimal design. The results for lubrication properties have shown that the SFA PFAD-based esters have low-temperature properties with pour points value in the range of 18–35 °C, flash point (270–310 °C), onset oxidative stability temperature (251–322 °C) and viscosity indices (115–131), respectively. The results showed that the presence of many esters functional groups in the molecule structure of SFA PFAD-based esters provides a positive impact on the lubrication properties. Overall, the results indicated that the SFA PFAD-based esters can be used as biolubricant base oils with pour point depressants.

___

  • 1. Gryglewicz S, Oko F. Dicarboxylic acid esters as components of modern synthetic oils. Industrial Lubrication and Tribology 2005; 57 (3): 128-132. doi: 10.1108/00368790510595101
  • 2. Knothe G, Steidley KR. Kinematic viscosity of biodiesel fuel components and related compounds. Influence of compound structure and comparison to petrodiesel fuel components. Fuel 2005; 84 (9): 1059-1065. doi: 10.1016/j.fuel.2005.01.016
  • 3. Erhan SZ. Industrial uses of plant oils, USA: Boca Raton, AOCS Press, 2005.
  • 4. Nagendramma P, Kaul S. Development of ecofriendly/biodegradable lubricants: An overview. Renewable and Sustainable Energy Reviews 2012; 16 (1): 764-774. doi: 10.1016/j.rser.2011.09.002
  • 5. Boyde S. Hydrolytic stability of synthetic ester lubricants. Journal of Synthetic Lubrication 2000; 16 (4): 297-312. doi: 10.1002/jsl.3000160403
  • 6. Kiss AA, Bildea CS. A review of biodiesel production by integrated reactive separation technologies. Journal of Chemical Technology & Biotechnology 2012; 87 (7): 861-879. doi: 10.1002/jctb.3785
  • 7. Hama S, Kondo A. Enzymatic biodiesel production: an overview of potential feedstocks and process development. Bioresource Technology 2013; 135: 386-395. doi: 10.1016/j.biortech.2012.08.014
  • 8. Calero J, Luna D, Sancho ED, Luna C, Bautista FM et al. An overview on glycerol-free processes for the production of renewable liquid biofuels, applicable in diesel engines. Renewable and Sustainable Energy Reviews 2015; 42: 1437-1452. doi: 10.1016/j.rser.2014.11.007
  • 9. Vernon FMJ. Standard Brands (UK) Ltd., Firelighter with palm fatty acid distillate. U.S. Patent Application 15/749,703, 2018.
  • 10. Kapor NZA; Maniam GP, Rahim MHA, Yusoff MM. Palm fatty acid distillate as a potential source for biodiesel production - a review. Journal of Cleaner Production 2017; 143: 1-9. doi: 10.1016/j.jclepro.2016.12.163
  • 11. Ping BTY, Yusof M. Characteristics and properties of fatty acid distillates from palm oil. Oil Palm Bulletin 2009; 59: 5-11.
  • 12. Majd AJ, Mohamad Firdaus MY, Salimon J, Murad B. Separation of saturated and unsaturated fatty acids of palm fatty acid distilled via low-temperature methanol crystallization. Malaysian Journal of Chemistry 2019; 21: 8-16.
  • 13. Baharudin KB, Taufiq-Yap YH, Hunns J, Isaacs M, Wilson K et al. Mesoporous NiO/Al-SBA-15 catalysts for solvent-free deoxygenation of palm fatty acid distillate. Microporous and Mesoporous Materials 2019; 276: 13-22. doi: 10.1016/j.micromeso.2018.09.014
  • 14. Widodo S, Khoiruddin K, Ariono D, Subagjo S, Wenten IG. Re-refining of waste engine oil using ultrafiltration membrane. Journal of Environmental Chemical Engineering 2020; 8 (3): 103789. doi: 10.1016/j.jece.2020.103789
  • 15. Koh MY, Tinia TI, Idris A. Synthesis of palm based biolubricant in an oscillatory flow reactor (OFR). Industrial Crops and Products 2014; 52: 567-574. doi: 10.1016/j.indcrop.2013.10.042
  • 16. Nowicki J, Stańczyk D, Drabik J, Mosio-Mosiewski J, Woszczyński P et al. Synthesis of fatty acid esters of selected higher polyols over homogeneous metallic catalysts. Journal of the American Oil Chemists’ Society 2016; 93 (7): 973-981. doi: 10.1007/s11746-016-2840-7
  • 17. Japir AA, Salih N, Salimon J. Synthesis and characterization of biodegradable palm palmitic acid based bioplastic. Turkish Journal of Chemistry 2021; 45: 585-599. doi:10.3906/kim-2011-31
  • 18. 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. Applied Science and Engineering Progress 2021; 14 (2): 175-186. doi: 10.14416/j.asep.2021.03.004
  • 19. Stachowiak GW, Batchelor AW. Engineering tribology, USA: New York, Elsevier Butterworth-Heinemann, 2005.
  • 20. Almasvandi MH, Rahimi M, Tagheie Y. Microfluidic cold stripping of H2S from crude oil in low temperature and natural gas consumption. Journal of Natural Gas Science and Engineering 2016; 34: 499-508. doi: 10.1016/j.jngse.2016.07.021
  • 21. Zhang Z, Zheng H. Optimization for decolorization of azo dye acid green 20 by ultrasound and H2O2 using response surface methodology. Journal of Hazardous Materials 2009; 172 (2-3): 1388-1393. doi: 10.1016/j.jhazmat.2009.07.146
  • 22. Eriksson L, Jaworska J, Worth AP, Cronin MT, McDowell RM et al. Methods for reliability and uncertainty assessment and for applicability evaluations of classification-and regression-based QSARs. Environmental Health Perspectives 2003; 111 (10): 1361-1375. doi: 10.1289/ehp.5758
  • 23. Myers RH, Montgomery DC, Vining GG, Borror CM, Kowalski SM. Response surface methodology: a retrospective and literature survey. Journal of Quality Technology 2004; 36 (1): 53-77. doi: 10.1080/00224065.2004.11980252
  • 24. Awang R, Ghazuli MR, Basri M. Immobilization of lipase from Candida Rugosa on palm-based polyurethane foam as a support material. American Journal of Biochemistry and Biotechnology 2007; 3 (3): 163-166. doi: 10.3844/ajbbsp.2007.163.166
  • 25. Sharma BK, Adhvaryu A, Liu Z, Erhan, SZ. Chemical modification of vegetable oils for lubricant applications. Journal of the American Oil Chemists' Society 2006; 83 (2): 129-136. doi: 10.1007/s11746-006-1185-z
  • 26. Bahadi M, Salih N, Salimon J. Synthesis and characterization of green biodegradable palm oleic acid based polyester. Biointerface Research in Applied Chemistry 2021; 11 (6): 14359-14371. doi: 10.33263/BRIAC116.1435914371
  • 27. Pavia DL, Lampman GM, Kriz GS, Vyvyan JR. Introduction to spectroscopy. 5th Ed., Cengage Learning, Inc.: USA, 2015.
  • 28. Alexandri E, Ahmed R, Siddiqui H, Choudhary MI, Tsiafoulis CG, Gerothanassis IP. High resolution NMR spectroscopy as a structural and analytical tool for unsaturated lipids in solution. Molecules 2017; 22 (10): 1663. doi: 10.3390/molecules22101663
  • 29. Mortier RM, Fox MF, Orszulik S. Chemistry and technology of lubricants. 3rd ed., New York: Springer, 2010.
  • 30. Lye YN, Salih N, Salimon J. Optimization of partial epoxidation on Jatropha curcas oil based methyl linoleate using urea-hydrogen peroxide and methyltrioxorhenium catalyst. Applied Science and Engineering Progress 2021; 14 (1): 89-99. doi: 10.14416/j.asep.2020.12.006
  • 31. Salih N, Salimon J. A Review on eco-friendly green biolubricants from renewable and sustainable plant oil sources. Biointerface Research in Applied Chemistry 2021; 11 (5): 13303-13327. doi: 10.33263/BRIAC115.1330313327
  • 32. Nor NM, Salih N, Salimon J. Chemically modified Jatropha curcas oil for biolubricant applications. Hemijska Industrija 2021; 75 (2): 117- 128. doi: 10.2298/hemind200809009n
  • 33. Salimon J, Salih N. Modification of epoxidized ricinoleic acid for biolubricant base oil with improved flash and pour points. Asian Journal of Chemistry 2010; 22: 5468-5476.
  • 34. Samidin S, Salih N, Salimon J. Synthesis and characterization of trimethylolpropane based esters as green biolubricant basestock. Biointerface Research in Applied Chemistry 2021; 11 (5): 13638-13651. doi: 10.33263/BRIAC115.1363813651
  • 35. Polansky R, Prosr P, Vik R, Moravcova D, Pihera J. Comparison of the mineral oil lifetime estimates obtained by differential scanning calorimetry, infrared spectroscopy, and dielectric dissipation factor measurements. Thermochimica Acta 2017; 647: 86-93. doi: 10.1016/j.tca.2016.12.002
  • 36. Nor NM, Salih N, Salimon J. Optimization of the ring opening of epoxidized palm oil using D-optimal design. Asian Journal of Chemistry 2021; 33 (1): 67-75. doi: 10.14233/ajchem.2021.22938
  • 37. Salih N, Salimon J. A Review on new trends, challenges and prospects of ecofriendly friendly green food-grade biolubricants. Biointerface Research in Applied Chemistry 2022; 12 (1): 1185-1207. doi: 10.33263/BRIAC121.11851207
  • 38. Arbain NH, Salimon J. The effects of various acid catalyst on the esterification of Jatropha curcas oil based trimethylolpropane ester as biolubricant base stock. E-Journal of Chemistry 2011; 8 (1): 33-40. doi: 10.1155/2011/789374
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

Enhancement of dispersion stability of inorganic additives via poly(sodium-4- styrenesulfonate) treatment geared to hydrogel applications

Filiz BORAN, Merve OKUTAN

Effect of current density on the microstructure and morphology of the electrodeposited nickel coatings

Amel BOUKHOUIETE, Saliha BOUMENDJEL, Nour El Houda SOBHI

Antiinfective properties of ursolic acid-loaded chitosan nanoparticles against Staphylococcus aureus

Fatemeh GHASEMZADEH, Ghasem D. NAJAFPOUR, Maedeh MOHAMMADI

Photocatalytic decomposition of textile dyestuffs by photosensitive metal oxide catalysts

Gülin Selda POZAN SOYLU, Esra Yeliz ALTUN, Z. Tuba ŞİŞMANOĞLU

Sn(II)/PN@AC catalysts: synthesis, physical-chemical characterization, and applications

Yibo WU, Yongjun HAN, Li WANG, Qinbin LI, Wei MA, Fu XV, Fuxiang LI

N doping of $TiO_2$ nanocrystal for efficient photodegradation of organic pollutants under ultraviolet and visible light irradiation

Qianrui LV, Xiaoyou YU

Ultrasound assisted supramolecular liquid phase microextraction procedure for Sudan I at trace level in environmental samples

Özgür ÖZALP, Furkan UZCAN, Mustafa SOYLAK

Pyridine substituted BODIPYs: synthesis, characterization and cholinesterease, α-glucosidase inhibitory, DNA hydrolytic cleavage effects

Zekeriya BIYIKLIOĞLU, Burak BARUT, Hüseyin BAŞ

Advances in polymer based Friedlander quinoline synthesis

Rajendra PATIL, Jagdish CHAVAN, Shivnath PATEL, Anil BELDAR

Preparation of G-CuO NPs and G-ZnO NPs with mallow leaves, investigation of their antibacterial behavior and synthesis of bis(indolyl)methane compounds under solventfree microwave assisted dry milling conditions using G-CuO NPs as a catalyst

Maden SULAK