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Synthesis of 2-Hidroxyethyl Ester (2-HEE) and 2-Hydroxypropyl Ester (2-HPE) from Castor Oil as Bioadditives to Improve the Cold Flow Characteristic of Biodiesel

Yulfi Zetra , Nirmala Puteri Batari , Talitha Fitra Firdausya , Yunita Alfiyati Firdausa , Rizka Berliana Putri , R.Y. Perry Burhan , Yuly Kusumawati

Published
May 14, 2026

Vol. 9 No. 1 (2026)
Pages 238-256

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Open Access
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Abstract

The utilization of biodiesel continues to increase along with the development of renewable energy. However, biodiesel tends to exhibit poorer cold flow properties compared to petroleum diesel. In this study, castor oil, a non-edible vegetable oil, was modified into 2-hydroxyethyl ester (2-HEE) and 2-hydroxypropyl ester (2-HPE) to improve the cold flow characteristic of biodiesel. The transesterification of 2-HEE and 2-HPE was carried out using fatty acid methyl esters (FAME) derived from castor oil with ethylene glycol (for 2-HEE) and propylene glycol (for 2-HPE), assisted by a K₂CO₃ catalyst at 150 °C, a mixing speed at 500 rpm, under a vacuum system. The optimum molar ratio of FAME to polyol was 1:10, yielding 69.63% for 2-HEE and 56.84% for 2-HPE. GC–MS analysis showed product abundances of 98.17% for 2-HEE (dominated by 2-hydroxyethyl ricinoleate at 77.4%) and 98.97% for 2-HPE (dominated by 2-hydroxypropyl ricinoleate at 77.9%). The addition of 2% v/v 2-HEE to biodiesel reduced the cloud point by 2.2 °C, the pour point by 3 °C, the flash point by 3 °C, and the density by 0.005 g/cm³, while increasing the kinematic viscosity by 0.21 cSt. Meanwhile, the addition of 2% v/v 2-HPE reduced the cloud point by 3.1 °C, the pour point by 4.3 °C, the flash point by 8 °C, and the density by 0.001 g/cm³, with an increase in kinematic viscosity of only 0.01 cSt. The 2-HPE compound showed superior performance as a bioadditive compared to 2-HEE in improving the cold flow characteristic of biodiesel without significantly altering its physical properties.

Keywords

Bioadditives; Biodiesel; Castor oil; Cold flow

References

  1. [1] A. Gautam, “Chemical Engineering and Processing - Process Intensification Optimization and Control of Continuous Biodiesel Production Processes : A Review,” Chemical Engineering and Processing - Process Intensification, vol. 213, no. April, p. 110323, 2025, doi: 10.1016/j.cep.2025.110323.
  2. [2] S. N. Gebremariam and J. M. Marchetti, “Economics of biodiesel production: Review,” Energy Conversion and Management, vol. 168, no. February, pp. 74–84, 2018, doi: 10.1016/j.enconman.2018.05.002.
  3. [3] Y. S. Pradana, I. G. B. N. Makertihartha, A. Indarto, T. Prakoso, and T. H. Soerawidjaja, “A Review of Biodiesel Cold Flow Properties and Its Improvement Methods: Towards Sustainable Biodiesel Application,” Energies, vol. 17, no. 18, p. 4543, 2024, doi: 10.3390/en17184543.
  4. [4] S. Y. Giraldo, L. A. Rios, and N. Suárez, “Comparison of glycerol ketals, glycerol acetates and branched alcohol-derived fatty esters as cold-flow improvers for palm biodiesel,” Fuel, vol. 108, no. x, pp. 709–714, 2013, doi: 10.1016/j.fuel.2013.02.039.
  5. [5] M. Abe, S. Hirata, H. Komatsu, K. Yamagiwa, and H. Tajima, “Thermodynamic selection of effective additives to improve the cloud point of biodiesel fuels,” Fuel, vol. 171, pp. 94–100, 2016, doi: 10.1016/j.fuel.2015.12.053.
  6. [6] H. Mulyani and A. Sujarwata, Lemak dan Minyak, 1st ed. Metro: Lembaga Penerbitan UM Metro, 2018.
  7. [7] A. V. Veličković, D. D. Rajković, J. M. Avramović, A. M. Marjanović Jeromela, M. S. Krstić, and V. B. Veljković, “Advancements in biodiesel production from castor oil: A comprehensive review,” Energy Conversion and Management, vol. 330, no. December 2024, 2025, doi: 10.1016/j.enconman.2025.119622.
  8. [8] D. Rajan, A. Benesh, and K. M. Nampoothiri, “Biomanufacturing of ricinoleic acid from castor oil using immobilized lipase of Pseudomonas guariconensis as biocatalyst,” Biocatalysis and Agricultural Biotechnology, vol. 58, no. February, p. 103184, 2024, doi: 10.1016/j.bcab.2024.103184.
  9. [9] R. A. Firmansyah, R. Y. Perry Burhan, Y. Zetra, and D. Prasetyoko, “The Development of Triglyceride-Based Additives and Their Lubricity Properties for Low Sulfur Fossil Diesel: A Review,” Journal of Tribology, vol. 144, no. 10, pp. 1–21, Oct. 2022, doi: 10.1115/1.4054398.
  10. [10] Y. Zetra, R. B. Putri, T. F. Firdhausya, Y. A. Firdausa, and R. Y. P. Burhan, “Synthesis of Waste Cooking Oil Based Bioadditive Through Transesterification and Its Feasibility as Lubricity Enhancer Bioadditives For Low-Sulfur Diesel Fuel : Preliminary Investigation,” Automotive Experiences, vol. 8, no. 2, pp. 436–450, 2025, doi: 10.31603/ae.14461.
  11. [11] M. U. H. Suzihaque, N. Syazwina, H. Alwi, U. K. Ibrahim, S. Abdullah, and N. Haron, “A sustainability study of the processing of kitchen waste as a potential source of biofuel: Biodiesel production from waste cooking oil (WCO),” Materials Today: Proceedings, vol. 63, pp. S484–S489, 2022, doi: 10.1016/j.matpr.2022.04.526.
  12. [12] Y. Zetra, R. A. B. Hariyanto, R. A. Firmansyah, R. Y. P. Burhan, and Pusparatu, “Lubricity Performance of Ethylene Glycol Ester from Soybean Oil as a Lubricity Enhancer Bio-Additive for Low-Sulfur Diesel Fuel,” Malaysian Journal of Fundamental and Applied Sciences, vol. 19, no. 4, pp. 481–493, Aug. 2023, doi: 10.11113/mjfas.v19n4.2843.
  13. [13] R. K. Elango, K. Sathiasivan, C. Muthukumaran, V. Thangavelu, M. Rajesh, and K. Tamilarasan, “Transesterification of castor oil for biodiesel production: Process optimization and characterization,” Microchemical Journal, vol. 145, no. October 2018, pp. 1162–1168, 2019, doi: 10.1016/j.microc.2018.12.039.
  14. [14] A. Firmansyah, Y. Zetra, R. Y. P. Burhan, D. Prasetyoko, and N. Jamarun, “Synthesis of 2-Hydroxyethyl Esters from Castor Oil as Lubrication Bio-Additive Candidates for Low-Sulfur Fossil Diesel,” Indonesian Journal of Chemistry, vol. 22, no. 1, p. 845, Jun. 2022, doi: 10.22146/ijc.73038.
  15. [15] G. P. Maniam, H. S. Lim, and N. Mat Hussin, “Effect of Free Fatty Acid on Transesterification of Waste Cooking Oil,” Current Science and Technology, vol. 3, no. 1, pp. 57–63, 2023, doi: 10.15282/cst.v3i1.10290.
  16. [16] P. Talwan, D. Gautam, R. Kumar, S. Kumar, A. Moudgil, and K. Varsha, “Experimental Study of Castor Oil from Plant Seed Ricinus Communis : Extraction and Chemical Modification,” Journal of Chemical Health Risks, vol. 14, pp. 501–506, 2024, [Online]. Available: https://www.jchr.org/index.php/JCHR/article/view/2326
  17. [17] K. Ramezani, S. Rowshanzamir, and M. H. Eikani, “Castor oil transesterification reaction: A kinetic study and optimization of parameters,” Energy, vol. 35, no. 10, pp. 4142–4148, 2010, doi: 10.1016/j.energy.2010.06.034.
  18. [18] M. Takayama, “Metastable McLafferty rearrangement reaction in the electron impact ionization of stearic acid methyl ester,” International Journal of Mass Spectrometry and Ion Processes, vol. 144, no. 3, pp. 199–204, 1995, doi: 10.1016/0168-1176(95)04169-L.
  19. [19] T. M. Chaouche, F. Haddouchi, I. Ghellai, and S. Souad, “Physicochemical parameters of oil extracted from Ricinus communis L. seeds,” Journal of Natural Product Research and Applications (JNPRA), vol. 1, no. 1, pp. 46–53, 2021, doi: 10.46325/jnpra.v1i01.5.
  20. [20] O. J. Omohu and A. C. Omale, “Physicochemical Properties and Fatty Acid Composition of Castor Bean Ricinus communis L . Seed Oil,” European Journal of Biophysics, vol. 5, no. 4, pp. 62–65, 2017, doi: 10.11648/j.ejb.20170504.11.
  21. [21] W. Abdelmoez et al., “Kinetic and Thermodynamics studies for Castor Oil Extraction Using Subcritical Water Technology,” Journal of Oleo Science, vol. 485, no. 6, pp. 477–485, 2016, doi: 10.5650/jos.ess15298.
  22. [22] O. M. A. Ali, M. A. A. Zaini, and J. M. Danlami, “Oxidation Stability of Castor Oil in Solvent Extraction,” Jurnal Teknologi, vol. 6, pp. 239–244, 2016, doi: 10.11113/jt.v78.4571.
  23. [23] M. Inomata, N. Hirai, N. Takeda, and H. Ohigashi, “Mechanism of the formation of a dehydrated ion by an unusual loss of oxygen at the 4′-carbonyl group of abscisic acid methyl ester in electron ionization mass spectrometry,” Journal of Mass Spectrometry, vol. 40, no. 8, pp. 1035–1043, 2005, doi: 10.1002/jms.878.
  24. [24] D. D. Ebbing and S. D. Gammon, General Chemistry. Boston New York: Houghton Mifflin Company, 2007.
  25. [25] T. . G. Solomons and C. B. Fryhle, Organic Chemistry, 10th ed., vol. 1, no. 1. United States: John Wiley & Sons, Inc., 2016.
  26. [26] S. Hederos and L. Baltzer, “Nucleophile selectivity in the acyl transfer reaction of a designed enzyme.,” Biopolymers, vol. 79, no. 6, pp. 292–299, Dec. 2005, doi: 10.1002/bip.20351.
  27. [27] R. H. Petrucci, F. G. Herring, J. D. Madura, and C. Bissonnette, General Chemstry Principles and Modern Applications, 11th ed., vol. 284, no. 5751. Canada, 2017. doi: 10.1038/284096b0.
  28. [28] N. P. Batari, Y. Zetra, R. Y. P. Burhan, T. Fitra, Y. A. Firdausa, and R. B. Putri, “Synthesis and Physicochemical Characterization of Castor Oil Methyl Ester,” Fullerene, vol. 10, no. 1, pp. 101–111, 2025, doi: 10.37033/fjc.v10i2.751.
  29. [29] M. A. Hazrat et al., “A Mini Review on the Cold Flow Properties of Biodiesel and its Blends,” Frontiers in Energy Research, vol. 8, no. December 2020, pp. 1–8, 2020, doi: 10.3389/fenrg.2020.598651.
  30. [30] C. Lamaisri, V. Punsuvon, S. Chanprame, and A. Arunyanark, “Relationship between fatty acid composition and biodiesel quality for nine commercial palm oils,” Songklanakarin Journal of Science and Technology, vol. 37, no. 4, pp. 389–395, 2015.
  31. [31] J. Joelianingsih, M. Christwardana, and I. S. Purwaningsih, “Prediction of Palm Based Biodiesel Properties Through the Preparation of Empirical Equation,” International Journal of Oil Palm, vol. 2, no. 1, pp. 12–23, Jan. 2019, doi: 10.35876/ijop.v2i1.25.
  32. [32] T. Yang et al., “Influence of polar groups on the depressive effects of polymethacrylate polymers as cold flow improvers for diesel fuel,” Fuel, vol. 290, no. January, p. 120035, 2021, doi: 10.1016/j.fuel.2020.120035.
  33. [33] R. O. Dunn, “Correlating the cloud point of biodiesel with its fatty acid methyl ester composition: Multiple regression analyses and the weighted saturation factor (wSF),” Fuel, vol. 300, no. May, p. 120820, 2021, doi: 10.1016/j.fuel.2021.120820.
  34. [34] P. Sivakumar, A. Sircar, B. Deka, A. Silviya Anumegalai, P. Suresh Moorthi, and N. Yasvanthrajan, “Flow improvers for assured flow of crude oil in midstream pipeline - A review,” Journal of Petroleum Science and Engineering, vol. 164, pp. 24–30, 2018, doi: 10.1016/j.petrol.2018.01.022.
  35. [35] A. K. F. Achmad, N. A. Fathurrahman, E. S. Kunarti, C. S. Wibowo, M. Khalil, and A. A. Al-Saadi, “Optimizing cold-flow properties and oxidation stability of B40 biodiesel blend with turpentine oil and ethanol: Experimental and quantum chemical approach,” Fuel, vol. 381, no. PA, p. 133258, 2025, doi: 10.1016/j.fuel.2024.133258.
  36. [36] A. B. Dikko, A. D. Ahmed, T. Pascal, and A. Alkasim, “Variations Of Excess Viscosities Of Alcohol-Water And Alcohol-Alcohol Mixtures With Temperature,” International Journal of Scientific and Technology Research, vol. 3, no. 9, pp. 306–308, 2014.
  37. [37] K. Lakzian, H. Liaw, E. Lakzian, and V. Gerbaud, “A comprehensive review on flash point behavior of binary ignitable mixtures : Trends , influencing factors , safety and fuel design implications , and future directions,” Progress in Energy and Combustion Science, vol. 108, no. September 2024, p. 101222, 2025, doi: 10.1016/j.pecs.2025.101222.
  38. [38] K. R. Bukkarapu and A. Krishnasamy, “A critical review on available models to predict engine fuel properties of biodiesel,” Renewable and Sustainable Energy Reviews, vol. 155, no. November 2021, p. 111925, 2022, doi: 10.1016/j.rser.2021.111925.
  39. [39] N. Damanik, I. Prahastono, T. H. Soerawidjaja, I. K. Reksowardojo, T. A. F. Soelaiman, and H. B. Tambunan, “Investigation of Coconut Methyl Ester (CME)-Palm Oil Methyl Ester (POME)-Diesel Blends Volatility BT - Sustainable Development with Renewable Energy,” in Sustainable Development with Renewable Energy, N. S. Caetano, Ed., Cham: Springer Nature Switzerland, 2024, pp. 113–123.
  40. [40] R. Koul, N. Kumar, and R. . Singh, “A review on the production and physicochemical properties of renewable diesel and its comparison with biodiesel,” Energy Sources, Part A: Recovery, Utilization, and Environmental Effects, vol. 43, no. 18, pp. 2235–2255, Sep. 2021, doi: 10.1080/15567036.2019.1646355.
  41. [41] N. N. Siti Mariam, S. S. Hoong, T. I. Tuan Noor Maznee, M. Z. Arniza, and R. M. Yusop, “Solketal Levulinate Ester As a Potential Fuel Additive for Palm Biodiesel,” Journal of Oil Palm Research, vol. 36, no. 1, pp. 104–114, 2024, doi: 10.21894/jopr.2023.0004.
  42. [42] M. Bahadi, J. Salimon, and D. Derawi, “Synthesis of di-trimethylolpropane tetraester-based biolubricant from Elaeis guineensis kernel oil via homogeneous acid-catalyzed transesterification,” Renewable Energy, vol. 171, pp. 981–993, 2021, doi: 10.1016/j.renene.2021.02.163.
  43. [43] T. C. Ming, N. Ramli, O. T. Lye, M. Said, and Z. Kasim, “Strategies for decreasing the pour point and cloud point of palm oil products,” European Journal of Lipid Science and Technology, vol. 107, no. 7–8, pp. 505–512, 2005, doi: 10.1002/ejlt.200400944.
  44. [44] W. A. Ahmed, A. Yarmo, N. Salih, M. D. Derawi, M. R. Yusop, and J. Salimon, “Synthesis and Lubricity Properties Analysis of Branched Dicarboxilate Ester Based Lubricant,” Malaysian Journal of Analytical Sciences, vol. 19, no. 1, pp. 106–117, 2015.
  45. [45] W. A. Ahmed, E. Yousif, M. H. Al-mashhadani, M. A. Yarmo, N. Salih, and J. Salimon, “Utjecaj dugolančanog i razgranatog alkohola na mazivost estera na bazi dodekandiojske kiseline (The Effect of Long-chain and Branched Alcohol on Lubricity of Dodecanedioic Acid Based Ester),” Kemija u industriji, vol. 70, no. 1–2, pp. 13–22, 2021, doi: 10.15255/KUI.2020.014.
  46. [46] C. Hu et al., “Ester Oils Prepared from Fully Renewable Resources and Their Lubricant Base Oil Properties,” ACS Omega, vol. 6, pp. 16346–16355, 2021, doi: 10.1021/acsomega.1c00808.
  47. [47] N. Chavhan, A. Mokashi, S. Chandak, B. Chaware, P. Bongarde, and S. Bodhe, “Development of bio lubricant from castor oil via chemical softening: An ease towards sustainable substitute,” Materials Today: Proceedings, no. September, 2023, doi: 10.1016/j.matpr.2023.09.061.
  48. [48] Musyaroh, W. Wijayanti, M. N. Sasongko, and Winarto, “Influence of sweet orange peel oil additive on physicochemical properties of gasoline,” Alexandria Engineering Journal, vol. 61, no. 6, pp. 4875–4888, 2022, doi: 10.1016/j.aej.2021.09.057.
  49. [49] H. Hindarso, Aylianawati, and M. E. Sianto, “Biodiesel production from the microalgae nannochloropsis by microwave using CaO and MgO catalysts,” International Journal of Renewable Energy Development, vol. 4, no. 1, pp. 72–76, 2015, doi: 10.14710/ijred.4.1.72-76.
  50. [50] J. F. Sierra-Cantor and C. A. Guerrero-Fajardo, “Methods for improving the cold flow properties of biodiesel with high saturated fatty acids content: A review,” Renewable and Sustainable Energy Reviews, vol. 72, no. April 2016, pp. 774–790, 2017, doi: 10.1016/j.rser.2017.01.077.
  51. [51] S. D. Romano and P. A. Sorichetti, “Refractive Index and Effective Polarizability of Biodiesel,” Journal of Petroleum & Chemical Engineering, pp. 1–5, 2023.
  52. [52] R. Zhang, W. Wang, J. Li, S. Xu, and Y. Wang, “Insights into how carbon chain length and branch position of alcohol solvents affect solid – liquid thermodynamic behavior of form I of probucol,” Journal of Thermal Analysis and Calorimetry, vol. 149, no. 7, pp. 2941–2952, 2024, doi: 10.1007/s10973-024-12883-5.
  53. [53] Wahyudi, M. Nadjib, and A. Parmono, “Pengaruh Densitas dan Viskositas Biodiesel Campuran Jatropha–Sawit Terhadap Sudut Injeksi,” Jurnal Ilmiah Indonesia, vol. 7, no. 09, 2022, doi: 10.36418/syntax-literate.v7i9.13502.
  54. [54] A. Moreau, M. Sobrino, J. Zambrano, J. J. Segovia, M. A. Villamañán, and M. Carmen Martín, “Viscosities and densities of different alcohols (1-propanol, 2-propanol, 1-pentanol and 2-pentanol) at high pressures,” Journal of Molecular Liquids, vol. 344, p. 117744, Dec. 2021, doi: 10.1016/j.molliq.2021.117744.
  55. [55] T. Odisu, L. Edomwonyi-Otu, E. Bassey, and E. Ohimor, “Effect of Branched and Straight Chained Alcohols on Performance of Crude oil Demulsifiers,” Journal of Applied Sciences and Environmental Management, vol. 23, no. 1, p. 59, Feb. 2019, doi: 10.4314/jasem.v23i1.10.
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Published May 14, 2026
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Copyright Copyright (c) 2026 Yulfi Zetra, Nirmala Puteri Batari, Talitha Fitra Firdausya, Yunita Alfiyati Firdausa, Rizka Berliana Putri, R.Y. Perry Burhan, Yuly Kusumawati
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Keywords
  • Bioadditives
  • Biodiesel
  • Castor oil
  • Cold flow

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