Synthesis of Ester from Waste Cooking Oil (WCO) and Pentaerythritol via Dean-Stark Distillation for Potential Use as Biolubricant

Juliati Br Tarigan; Ebenezer Primsa  Ginsu; Cut Fatimah Zuhra

doi:10.32734/jcnar.v7i1.20548

Authors

Juliati Br Tarigan Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Sumatera Utara, Medan, 20155, Indonesia
Ebenezer Primsa Ginsu Postgraduate School of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Sumatera Utara, Medan, 20155, Indonesia
Cut Fatimah Zuhra Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Sumatera Utara, Medan, 20155, Indonesia

DOI:

https://doi.org/10.32734/jcnar.v7i1.20548

Keywords:

Biolubricant, Dean-Stark Distillation, Pentaerythritol, Synthesis, Waste Cooking Oil

Abstract

Waste cooking oil (WCO) is a group of oils or fats that have been used for cooking or frying repeatedly and are no longer suitable for use. Repeated heating of cooking oil will cause the formation of trans fatty acids that trigger coronary heart disease (CHD). This study aims to synthesize esters as biolubricant candidates from WCO. WCO was purified using 0.05% (v/v) of H₃PO₄ and 2% (w/v) of bleaching earth, then saponified with ethanolic NaOH and hydrolyzed with 25% H₂SO₄. The fatty acids obtained were then esterified with pentaerythritol using a dean-stark distillation apparatus with 2% H2SO4 catalyst and toluene solvent at a temperature of 170-180°C for 6 hours. The results of the acid number analysis showed an ester conversion of 83.08%. Furthermore, the FT-IR spectra showed the presence of C=O (1730 cm⁻¹) and C–O–C (1178 cm⁻¹) groups, indicating the formation of esters. These results indicate that esters from used cooking oil have the potential to be environmentally friendly biolubricants.

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References

Vemullapalli V, Lakkoju B. A potential pentaerythritol-based bio-lubricants from 10-undecylenic acid: Its physico-chemical assessment. Journal of the Indian Chemical Society. 2023 Jun 1;100(6).

Aziz NAM, Yunus R, Rashid U, Syam AM. Application of response surface methodology (RSM) for optimizing the palm-based pentaerythritol ester synthesis. Ind Crops Prod. 2014 Aug 25;62:305–12.

Jumaah A. D-Optimal Design Optimization for Esterification of Palm Fatty Acids Distillate with Polyhydric Alcohols for Biolubricants Production. Vol. 41, J. Chem. Chem. Eng. Research Article.

Máximo F, Bastida J, Montiel C, Gómez M, Murcia MD, Barqueros C, et al. Branched saturated esters and diesters: Sustainable synthesis of excellent biolubricants. Catal Today. 2024 Mar 1;429.

Salimon J, Salih N, Yousif E. Biolubricants: Raw materials, chemical modifications and environmental benefits. Vol. 112, European Journal of Lipid Science and Technology. 2010. p. 519–30.

Soni H, Bhattu M, Verma M, Kaur M, Al-Kahtani AA, Hussain Lone I, et al. From kitchen to cosmetics: Study on the physicochemical and antioxidant properties of waste cooking oil-derived soap. J King Saud Univ Sci. 2024 Nov 1;36(10).

Cárdenas J, Orjuela A, Sánchez DL, Narváez PC, Katryniok B, Clark J. Pre-treatment of used cooking oils for the production of green chemicals: A review. Vol. 289, Journal of Cleaner Production. Elsevier Ltd; 2021.

Yaakob Z, Mohammad M, Alherbawi M, Alam Z, Sopian K. Overview of the production of biodiesel from Waste cooking oil. Renewable and Sustainable Energy Reviews [Internet]. 2013;18:184–93. Available from: https://www.sciencedirect.com/science/article/pii/S1364032112005588

Balasubramaniam B, Sudalaiyadum Perumal A, Jayaraman J, Mani J, Ramanujam P. Comparative analysis for the production of fatty acid alkyl esterase using whole cell biocatalyst and purified enzyme from Rhizopus oryzae on waste cooking oil (sunflower oil). Waste Management [Internet]. 2012;32(8):1539–47. Available from: https://www.sciencedirect.com/science/article/pii/S0956053X12001213

Mannu A, Ferro M, Di Pietro ME, Mele A. Innovative applications of waste cooking oil as raw material. Sci Prog. 2019 Jun 1;102(2):153–60.

Capuano D, Costa M, Di Fraia S, Massarotti N, Vanoli L. Direct use of waste vegetable oil in internal combustion engines. Vol. 69, Renewable and Sustainable Energy Reviews. Elsevier Ltd; 2017. p. 759–70.

Chrysikou LP, Dagonikou V, Dimitriadis A, Bezergianni S. Waste cooking oils exploitation targeting EU 2020 diesel fuel production: Environmental and economic benefits. J Clean Prod. 2019 May 10;219:566–75.

Karmee SK. Liquid biofuels from food waste: Current trends, prospect and limitation. Renewable and Sustainable Energy Reviews [Internet]. 2016;53:945–53. Available from: https://www.sciencedirect.com/science/article/pii/S1364032115010114

Joshi JR, Bhanderi KK, Patel J V., Karve M. Chemical modification of waste cooking oil for the biolubricant production through transesterification process. Journal of the Indian Chemical Society. 2023 Mar 1;100(3).

Borugadda VB, Goud V V. Improved thermo-oxidative stability of structurally modified waste cooking oil methyl esters for bio-lubricant application. J Clean Prod [Internet]. 2016;112:4515–24. Available from: https://www.sciencedirect.com/science/article/pii/S0959652615007751

Pujiastuti C, Sumada K, Armidianti M, Rimarsya A, Ahmad B. Bleaching Earth Recovery from Waste to Purify Coocking Oil by Extraction-Activation Method. Journal of Research and Technology. 2022;8(2):169–77.

Noubigh A, Abderrabba M. Investigation on solvent effect, transfer properties and preferential solvation of pentaerythritol in (methanol, ethanol and 2-propanol) + water mixtures. J Mol Liq. 2025 Mar 15;422.

Khairuddin MM, Abdullah A, Nor NM. Synthesis and Characterization of Sunflower Oil Unsaturated Fatty Acid Pentaerythritol Ester as Green Biolubricant Base Stock. Vol. 26, Malaysian Journal of Chemistry. 2024.

Emel’ianov V V., Krasnykh EL, Portnova S V., Levanova S V. Synthetic oils based on pentaerythritol esters. Vapor pressure and enthalpy of vaporization. Fuel. 2022 Mar 15;312.

He C, Guo Z, Deng Z, Li S, Zhang X. Enzyme-catalyzed preparation of polyol ester lubricants and performance research-based on pelargonic acid, oleic acid and trimethylolpropane. Biochem Eng J. 2022 Nov 1;187.

Aziz NAM, Yunus R, Rashid U, Zulkifli NWM. Temperature effect on tribological properties of polyol ester-based environmentally adapted lubricant. Tribol Int [Internet]. 2016;93:43–9. Available from: https://www.sciencedirect.com/science/article/pii/S0301679X15004168

Raof NA, Yunus R, Rashid U, Azis N, Yaakub Z. Effect of molecular structure on oxidative degradation of ester based transformer oil. Tribol Int. 2019 Dec 1;140.

Wang Y, Liang Y, Li Y, Rui W, He J, Zhao M. Synthesis, tribological properties and oxidative stability of polyol esters base oils containing pentaerythritol complex esters. Tribol Int [Internet]. 2024;195:109618. Available from: https://www.sciencedirect.com/science/article/pii/S0301679X24003700

Harmami SB, Meliana Y, Wahyuningsih P, Gozan M. Optimization of ethyl oleate from oleic acid and ethanol with Dean-Stark trap technology by response surface methodology. In: E3S Web of Conferences. EDP Sciences; 2024.

Zubenko SO. The simple method of vegetable oils and oleochemical products acid value determination. Catalysis and Petrochemistry [Internet]. 2021;(31):69–74. Available from: http://kataliz.org.ua/index.php/journal/article/view/16

Mannu Alberto, Ferro Monica, Pietro ME Di, Mele Andrea. Innovative applications of waste cooking oil as raw material. Sci Prog [Internet]. 2019 Jun 1;102(2):153–60. Available from: https://doi.org/10.1177/0036850419854252

Issariyakul T, Dalai AK. Biodiesel from vegetable oils. Renewable and Sustainable Energy Reviews [Internet]. 2014;31:446–71. Available from: https://www.sciencedirect.com/science/article/pii/S1364032113007508

Chozhavendhan S, Vijay Pradhap Singh M, Fransila B, Praveen Kumar R, Karthiga Devi G. A review on influencing parameters of biodiesel production and purification processes. Current Research in Green and Sustainable Chemistry [Internet]. 2020;1–2:1–6. Available from: https://www.sciencedirect.com/science/article/pii/S2666086520300023

Menalla E, Serna JG, Cantero D, Cocero MJ. Hydrothermal hydrolysis of triglycerides: Tunable and intensified production of diglycerides, monoglycerides, and fatty acids. Chemical Engineering Journal [Internet]. 2024;493:152391. Available from: https://www.sciencedirect.com/science/article/pii/S1385894724038786

Razzak SA, Zakir Hossain SM, Ahmed U, Hossain MM. Cleaner biodiesel production from waste oils (cooking/vegetable/frying): Advances in catalytic strategies. Fuel [Internet]. 2025;393:134901. Available from: https://www.sciencedirect.com/science/article/pii/S0016236125006258

Chemat F, Vian MA, Ravi HK, Khadhraoui B, Hilali S, Perino S, et al. Review of alternative solvents for green extraction of food and natural products: Panorama, principles, applications and prospects. Vol. 24, Molecules. MDPI AG; 2019.

Hamnas A, Unnikrishnan G. Bio-lubricants from vegetable oils: Characterization, modifications, applications and challenges – Review. Renewable and Sustainable Energy Reviews [Internet]. 2023;182:113413. Available from: https://www.sciencedirect.com/science/article/pii/S1364032123002708

Nor NM, Salih N, Salimon J. Optimization and lubrication properties of Malaysian crude palm oil fatty acids based neopentyl glycol diester green biolubricant. Renew Energy. 2022 Nov 1;200:942–56.

McNutt J, He Q (Sophia). Development of biolubricants from vegetable oils via chemical modification. Journal of Industrial and Engineering Chemistry [Internet]. 2016;36:1–12. Available from: https://www.sciencedirect.com/science/article/pii/S1226086X16000708

Salimon J, Salih N, Yousif E. Synthesis, Characterization and Physicochemical Properties of Oleic Acid Ether Derivatives as Biolubricant Basestocks [Internet]. Vol. 60, J. Oleo Sci. 2011. Available from: http://www.jstage.jst.go.jp/browse/jos/http://mc.manusriptcentral.com/jjocs

Fernandes KV, Papadaki A, da Silva JAC, Fernandez-Lafuente R, Koutinas AA, Freire DMG. Enzymatic esterification of palm fatty-acid distillate for the production of polyol esters with biolubricant properties. Ind Crops Prod [Internet]. 2018;116:90–6. Available from: https://www.sciencedirect.com/science/article/pii/S0926669018301717

Panchal TM, Patel A, Chauhan DD, Thomas M, Patel J V. A methodological review on bio-lubricants from vegetable oil based resources. Renewable and Sustainable Energy Reviews [Internet]. 2017;70:65–70. Available from: https://www.sciencedirect.com/science/article/pii/S1364032116308061

Knothe G, Steidley KR. A comparison of used cooking oils: A very heterogeneous feedstock for biodiesel. Bioresour Technol [Internet]. 2009;100(23):5796–801. Available from: https://www.sciencedirect.com/science/article/pii/S0960852409006981

Rabelo SN, Ferraz VP, Oliveira LS, Franca AS. FTIR Analysis for Quantification of Fatty Acid Methyl Esters in Biodiesel Produced by Microwave-Assisted Transesterification. International Journal of Environmental Science and Development [Internet]. 2015;6(12):964–9. Available from: http://www.ijesd.org/show-72-1091-1.html

Farobie O, Matsumura Y. Biodiesel Production in Supercritical Methanol Using a Novel Spiral Reactor. Procedia Environ Sci [Internet]. 2015;28:204–13. Available from: https://www.sciencedirect.com/science/article/pii/S187802961500239X

Meher LC, Churamani CP, Arif Md, Ahmed Z, Naik SN. Jatropha curcas as a renewable source for bio-fuels—A review. Renewable and Sustainable Energy Reviews [Internet]. 2013;26:397–407. Available from: https://www.sciencedirect.com/science/article/pii/S1364032113003687

Borugadda VB, Goud V V. Synthesis of Waste Cooking Oil Epoxide as a Bio-Lubricant Base Stock: Characterization and Optimization Study. Journal of Bioprocess Engineering and Biorefinery. 2014 Sep 9;3(1):57–72.