Research Article
BibTex RIS Cite

Synthesis of Plant-Based Ester for Metalworking Fluids and Tribological Performance

Year 2025, Volume: 13 Issue: 1, 430 - 442, 30.01.2025
https://doi.org/10.29130/dubited.1501022

Abstract

Lubricants derived from plant-based raw materials offer great potential for the development of environmentally friendly and renewable esters due to their easier and faster biodegradability, reducing dependence on petrochemical raw materials and creating new synthesis processes. The increasing burden of environmental regulations and the depletion of petroleum-derived raw materials have prompted many industries to opt for products based on natural raw materials. Due to these positive effects, vegetable oil-based esters have recently been considered as potential candidates for industrial use. In this context, ester synthesis from cottonseed oil, a natural biodegradable raw material source, was carried out by transesterification with isopropyl alcohol. The structure of the synthesized ester was elucidated by GC-FID and FTIR and important physical parameters such as acid number, saponification
number, viscosity and density of the ester were investigated. The synthesized isopropyl cottonseed oil ester was used to formulate a synthetic metalworking fluid at concentrations of 2%, 4% and 6%. The tribological properties of the formulated metalworking fluid were evaluated using the Reichert test and the chip corrosion test. It was found that the addition of 6% isopropyl cottonseed oil ester to the synthetic metalworking fluid exhibited the best tribological properties.

Supporting Institution

This work is supported by 3-S Engineering R&D Department (Project no: PTZ-10 and PTZ-15).

References

  • [1] S. Miao, P. Wang, Z. Su, and S. Zhang, “Vegetable-oil-based polymers as future polymeric biomaterials,” Acta Biomaterialia, vol. 10, no. 4, pp. 1692–1704, 2014.
  • [2] L. Isom and M. Hanna, “Biodiesel current and future perspectives,” in Handbook of Plant-Based Biofuels, LCC, USA: CRC Press, 2008, pp. 177–181.
  • [3] Y. X. Xu and M. A. Hanna, “Synthesis and characterization of hazelnut oil-based biodiesel,” Industrial Crops and Products, vol. 29, no. 2–3, pp. 473–479, 2009.
  • [4] G. Salinas-Solano, J. Porcayo-Calderon, L. M. Martinez, J. Canto, M. Casales, O. Sotelo-Mazon, J. Hanao and L. Martinez-Gomez, “Development and evaluation of a green corrosion inhibitor based on rice bran oil obtained from agro-industrial waste,” Industrial Crops and Products, vol. 119, pp. 111–124,2018.
  • [5] B. Kamya, H. Wang, T. Razipour, D. W. Chambers, A. S. Bassi and C. Xu, “Production of high-end bio-lubricant products via epoxidation of canola oil trimethylolpropane (COTMP) esters,” Industrial Crops and Products, vol. 222, no. 3, pp. 119-127, 2024.
  • [6] R. Sankaranarayanan, N. R. J. Hynes, J. S. Kumar and G. M. Krolczyk, “A comprehensive review on research developments of vegetable-oil based cutting fluids for sustainable machining challenges,” Journal of Manufacturing Processes, vol. 67, pp. 286–313, 2021.
  • [7] D. F. Silva-Alvarez, I. Dominguez-Lopez, M. A. Vidales Hurtado, C. GutierrezAntonio, K. A. Flores-Garay, and A. L. Garcia-Garcia, “A review on the menagerie of green fluids and nanoparticles to develop sustainable biolubricant technologies,” Environmental Technology & Innovation Journal, vol. 33, pp. 103-115, 2024.
  • [8] S. A. Lawal, I. A. Choudhury, and Y. Nukman, “Evaluation of vegetable and mineral oil-in-water emulsion cutting fluids in turning AISI 4340 steel with coated carbide tools,” Journal of Cleaner Production, vol. 66, pp. 610–618, 2014.
  • [9] M. R. Noor El-Din, M. R. Mishrif, S. V. Kailas, and J. K. Mannekote, “Studying the lubricity of new eco-friendly cutting oil formulation in metal working fluid,” Industrial Lubrication and Tribology, vol. 70, no. 9, pp. 1569–1579, 2018.
  • [10] C. He, Y. Yan, S. Li, L. Zhang, X. Zhao, Z. Deng and X. Zhang, “Modification of cottonseed oil with lipases and ionic liquid catalysts to prepare highly branched lubricant with low pour point and high viscosity,” Biochemical Engineering Journal, vol. 192, p. 108-118, 2023.
  • [11] S. Patil, K. Rajurkar, S. Patil and A. Pratap, “Synthesis of guerbet esters and its application in drilling and grinding oil” Tribology International, vol. 177, pp. 107-119, 2023.
  • [12] Acid Value of Fats and Oils, AOCS Official Method Cd 3d-63, 2017.
  • [13] Saponification Value of Industrial Oils and Derivatives, AOCS Official Method Tl 1a-64, 2022.
  • [14] Standard Test Method for Kinematic Viscosity of Transparent and Opaque Liquids, ASTM D445, 2024.
  • [15] Standard Test Methods for Specific Gravity, Apparent, of Liquid Industrial Chemicals, ASTM D891, 2016.
  • [16] Standard Test Method for Flash Point and Fire Point of Liquids by Tag Open-Cup Apparatus, ASTM D1310, 2018.
  • [17] Fatty Acid in Edible Oils and Fats by Capillary GLC, AOCS Official MEthod Ce 1a-13, 2017.
  • [18] G. Pipuš, I. Plazl, and T. Koloini, “Esterification of benzoic acid with 2-ethylhexanol in a microwave stirred-tank reactor,” Industrial & Engineering Chemistry Research, vol. 41, no. 5, pp. 1129–1134, 2002.
  • [19] B. Seidel and D. Meyer, “Investigation of the influence of aging on the lubricity of metalworking fluids by means of design of experiment,” Lubricants, vol. 7, no. 11, p. 94, 2019.
  • [20] Testing of cooling lubricants; determination of corrosion preventing characteristics of cooling lubricants mixed with water; chip/filter paper method, European Standarts DIN 51360 2, 1981.
  • [21] M. A. Zia, S. H. Shah, S. Shoukat, Z. Hussain, S. U. Khan, and N. Shafqat, “Physicochemical features, functional characteristics, and health benefits of cottonseed oil: a review,” Brazilian Journal of Biology, vol. 82, pp.1-15, 2022. [22] P. Dubey, P. Sharma, and V. Kumar, “FTIR and GC–MS spectral datasets of wax from Pinus roxburghii Sarg. needles biomass,” Data Brief, vol. 15, pp. 615–622, 2017.
  • [23] R. Padmini, P. V. Krishna and G. K. Rao, “Effectiveness of vegetable oil based nanofluids as potential cutting fluids in turning AISI 1040 steel,” Tribology International, vol. 94, pp. 490-501, 2016.
  • [24] S. M. Alves, B. S. Barros, M. F. Trajano, K. S. B. Ribeiro and E. Moura, “Tribological behavior of vegetable oil-based lubricants with nanoparticles of oxides in boundary lubrication conditions” Tribology International, vol. 65, pp. 28-36, 2013.
  • [25] S. Gill and A. Rowntree, “Liquid lubricants for spacecraft applications,” in Chemistry and Technology of Lubricants, Dordrecht, Netherlands: Springer, 2009, pp. 375–387.
  • [26] R. L. Stambaugh and B. G. Kinker, “Viscosity index improvers and thickeners,” in Chemistry and Technology of Lubricants, Dordrecht, Netherlands: Springer, 2009, pp. 153-187. [27] E. Brinksmeier, D. Meyer, A. G. Huesmann-Cordes and C. Herrmann, "Metalworking fluids mechanisms and performance," CIRP Annals, vol. 64, no. 2, pp. 605-628, 2015.
  • [28] B. Kamyab, H. Wang, C. Xu, D. W. Chambers, and A. S. Bassi, “Preparing vegetable oils-based metalworking fluids by a hydrolysis-esterification two-step process,” Biomass Bioenergy, vol. 183, pp. 167-175, 2024.
  • [29] I. S. Afonso, G. Nobrega, R. Lima, J. R. Gomes, and J. E. Ribeiro, “Conventional and recent advances of vegetable oils as metalworking fluids: a review,” Lubricants, vol. 11, no. 4, pp. 160-178, 2023.
  • [30] A. Adhvaryu, S. Z. Erhan, and J. M. Perez, “Tribological studies of thermally and chemically modified vegetable oils for use as environmentally friendly lubricants,” Wear, vol. 257, no. 3–4, pp. 359–367, 2004.
  • [31] B. Podgornik, S. Jacobson, and S. Hogmark, “Influence of EP and AW additives on the tribological behaviour of hard low friction coatings,” Surface and Coatings Technology, vol. 165, no. 2, pp. 168–175, 2003.
  • [32] N. J. Fox and G. W. Stachowiak, “Vegetable oil-based lubricants—A review of oxidation,” Tribology International, vol. 40, no. 7, pp. 1035–1046, 2007.
  • [33] S. Soni and M. Agarwal, “Lubricants from renewable energy sources – a review,” Green Chemistry Letters and Reviews, vol. 7, no. 4, pp. 359–382, 2014.

Metal İşleme Sıvısında Kullanılan Bitkisel Yağ Bazlı Ester Sentezi ve Tribolojik Performansı

Year 2025, Volume: 13 Issue: 1, 430 - 442, 30.01.2025
https://doi.org/10.29130/dubited.1501022

Abstract

Bitkisel bazlı hammaddelerden elde edilen yağlayıcılar, daha kolay ve daha hızlı biyolojik olarak
parçalanabilmeleri, petrokimyasal hammaddelere bağımlılığı azaltmaları ve yeni sentez süreçleri
yaratmaları nedeniyle çevre dostu ve yenilenebilir esterlerin geliştirilmesi için büyük bir potansiyel
sunmaktadır. Çevresel düzenlemelerin artan yükü ve petrol türevi hammaddelerin tükenmesi, birçok
endüstriyi doğal hammaddelere dayalı ürünleri tercih etmeye yöneltmiştir. Bu olumlu etkiler nedeniyle,
bitkisel yağ bazlı esterler son zamanlarda endüstriyel kullanım için potansiyel adaylar olarak
değerlendirilmektedir. Bu bağlamda, biyolojik olarak parçalanabilen doğal bir hammadde kaynağı olan
pamuk tohumu yağından ester sentezi, izopropil alkol ile transesterifikasyon yoluyla gerçekleştirilmiştir.
Sentezlenen esterin yapısı GC-FID ve FTIR ile aydınlatılmış ve esterin asit sayısı, sabunlaşma sayısı,
viskozitesi ve yoğunluğu gibi önemli fiziksel parametreleri incelenmiştir. Sentezlenen izopropil pamuk
tohumu yağı esteri, %2, %4 ve %6 konsantrasyonlarında sentetik bir metal işleme sıvısı formüle etmek
için kullanılmıştır. Formüle edilen metal işleme sıvısının tribolojik özellikleri Reichert testi ve talaşlı
korozyon testi kullanılarak değerlendirilmiştir. Sentetik metal işleme sıvısına %6 izopropil pamuk
tohumu yağı esteri ilavesinin en iyi tribolojik özellikleri sergilediği bulunmuştur.

Supporting Institution

3-S Mühendislik Müşavirlik San. ve Tic. A.Ş.

References

  • [1] S. Miao, P. Wang, Z. Su, and S. Zhang, “Vegetable-oil-based polymers as future polymeric biomaterials,” Acta Biomaterialia, vol. 10, no. 4, pp. 1692–1704, 2014.
  • [2] L. Isom and M. Hanna, “Biodiesel current and future perspectives,” in Handbook of Plant-Based Biofuels, LCC, USA: CRC Press, 2008, pp. 177–181.
  • [3] Y. X. Xu and M. A. Hanna, “Synthesis and characterization of hazelnut oil-based biodiesel,” Industrial Crops and Products, vol. 29, no. 2–3, pp. 473–479, 2009.
  • [4] G. Salinas-Solano, J. Porcayo-Calderon, L. M. Martinez, J. Canto, M. Casales, O. Sotelo-Mazon, J. Hanao and L. Martinez-Gomez, “Development and evaluation of a green corrosion inhibitor based on rice bran oil obtained from agro-industrial waste,” Industrial Crops and Products, vol. 119, pp. 111–124,2018.
  • [5] B. Kamya, H. Wang, T. Razipour, D. W. Chambers, A. S. Bassi and C. Xu, “Production of high-end bio-lubricant products via epoxidation of canola oil trimethylolpropane (COTMP) esters,” Industrial Crops and Products, vol. 222, no. 3, pp. 119-127, 2024.
  • [6] R. Sankaranarayanan, N. R. J. Hynes, J. S. Kumar and G. M. Krolczyk, “A comprehensive review on research developments of vegetable-oil based cutting fluids for sustainable machining challenges,” Journal of Manufacturing Processes, vol. 67, pp. 286–313, 2021.
  • [7] D. F. Silva-Alvarez, I. Dominguez-Lopez, M. A. Vidales Hurtado, C. GutierrezAntonio, K. A. Flores-Garay, and A. L. Garcia-Garcia, “A review on the menagerie of green fluids and nanoparticles to develop sustainable biolubricant technologies,” Environmental Technology & Innovation Journal, vol. 33, pp. 103-115, 2024.
  • [8] S. A. Lawal, I. A. Choudhury, and Y. Nukman, “Evaluation of vegetable and mineral oil-in-water emulsion cutting fluids in turning AISI 4340 steel with coated carbide tools,” Journal of Cleaner Production, vol. 66, pp. 610–618, 2014.
  • [9] M. R. Noor El-Din, M. R. Mishrif, S. V. Kailas, and J. K. Mannekote, “Studying the lubricity of new eco-friendly cutting oil formulation in metal working fluid,” Industrial Lubrication and Tribology, vol. 70, no. 9, pp. 1569–1579, 2018.
  • [10] C. He, Y. Yan, S. Li, L. Zhang, X. Zhao, Z. Deng and X. Zhang, “Modification of cottonseed oil with lipases and ionic liquid catalysts to prepare highly branched lubricant with low pour point and high viscosity,” Biochemical Engineering Journal, vol. 192, p. 108-118, 2023.
  • [11] S. Patil, K. Rajurkar, S. Patil and A. Pratap, “Synthesis of guerbet esters and its application in drilling and grinding oil” Tribology International, vol. 177, pp. 107-119, 2023.
  • [12] Acid Value of Fats and Oils, AOCS Official Method Cd 3d-63, 2017.
  • [13] Saponification Value of Industrial Oils and Derivatives, AOCS Official Method Tl 1a-64, 2022.
  • [14] Standard Test Method for Kinematic Viscosity of Transparent and Opaque Liquids, ASTM D445, 2024.
  • [15] Standard Test Methods for Specific Gravity, Apparent, of Liquid Industrial Chemicals, ASTM D891, 2016.
  • [16] Standard Test Method for Flash Point and Fire Point of Liquids by Tag Open-Cup Apparatus, ASTM D1310, 2018.
  • [17] Fatty Acid in Edible Oils and Fats by Capillary GLC, AOCS Official MEthod Ce 1a-13, 2017.
  • [18] G. Pipuš, I. Plazl, and T. Koloini, “Esterification of benzoic acid with 2-ethylhexanol in a microwave stirred-tank reactor,” Industrial & Engineering Chemistry Research, vol. 41, no. 5, pp. 1129–1134, 2002.
  • [19] B. Seidel and D. Meyer, “Investigation of the influence of aging on the lubricity of metalworking fluids by means of design of experiment,” Lubricants, vol. 7, no. 11, p. 94, 2019.
  • [20] Testing of cooling lubricants; determination of corrosion preventing characteristics of cooling lubricants mixed with water; chip/filter paper method, European Standarts DIN 51360 2, 1981.
  • [21] M. A. Zia, S. H. Shah, S. Shoukat, Z. Hussain, S. U. Khan, and N. Shafqat, “Physicochemical features, functional characteristics, and health benefits of cottonseed oil: a review,” Brazilian Journal of Biology, vol. 82, pp.1-15, 2022. [22] P. Dubey, P. Sharma, and V. Kumar, “FTIR and GC–MS spectral datasets of wax from Pinus roxburghii Sarg. needles biomass,” Data Brief, vol. 15, pp. 615–622, 2017.
  • [23] R. Padmini, P. V. Krishna and G. K. Rao, “Effectiveness of vegetable oil based nanofluids as potential cutting fluids in turning AISI 1040 steel,” Tribology International, vol. 94, pp. 490-501, 2016.
  • [24] S. M. Alves, B. S. Barros, M. F. Trajano, K. S. B. Ribeiro and E. Moura, “Tribological behavior of vegetable oil-based lubricants with nanoparticles of oxides in boundary lubrication conditions” Tribology International, vol. 65, pp. 28-36, 2013.
  • [25] S. Gill and A. Rowntree, “Liquid lubricants for spacecraft applications,” in Chemistry and Technology of Lubricants, Dordrecht, Netherlands: Springer, 2009, pp. 375–387.
  • [26] R. L. Stambaugh and B. G. Kinker, “Viscosity index improvers and thickeners,” in Chemistry and Technology of Lubricants, Dordrecht, Netherlands: Springer, 2009, pp. 153-187. [27] E. Brinksmeier, D. Meyer, A. G. Huesmann-Cordes and C. Herrmann, "Metalworking fluids mechanisms and performance," CIRP Annals, vol. 64, no. 2, pp. 605-628, 2015.
  • [28] B. Kamyab, H. Wang, C. Xu, D. W. Chambers, and A. S. Bassi, “Preparing vegetable oils-based metalworking fluids by a hydrolysis-esterification two-step process,” Biomass Bioenergy, vol. 183, pp. 167-175, 2024.
  • [29] I. S. Afonso, G. Nobrega, R. Lima, J. R. Gomes, and J. E. Ribeiro, “Conventional and recent advances of vegetable oils as metalworking fluids: a review,” Lubricants, vol. 11, no. 4, pp. 160-178, 2023.
  • [30] A. Adhvaryu, S. Z. Erhan, and J. M. Perez, “Tribological studies of thermally and chemically modified vegetable oils for use as environmentally friendly lubricants,” Wear, vol. 257, no. 3–4, pp. 359–367, 2004.
  • [31] B. Podgornik, S. Jacobson, and S. Hogmark, “Influence of EP and AW additives on the tribological behaviour of hard low friction coatings,” Surface and Coatings Technology, vol. 165, no. 2, pp. 168–175, 2003.
  • [32] N. J. Fox and G. W. Stachowiak, “Vegetable oil-based lubricants—A review of oxidation,” Tribology International, vol. 40, no. 7, pp. 1035–1046, 2007.
  • [33] S. Soni and M. Agarwal, “Lubricants from renewable energy sources – a review,” Green Chemistry Letters and Reviews, vol. 7, no. 4, pp. 359–382, 2014.
There are 31 citations in total.

Details

Primary Language English
Subjects Catalysis and Mechanisms of Reactions, Tribology
Journal Section Articles
Authors

Ertuğrul Kaya 0000-0003-1579-6411

Publication Date January 30, 2025
Submission Date June 13, 2024
Acceptance Date November 2, 2024
Published in Issue Year 2025 Volume: 13 Issue: 1

Cite

APA Kaya, E. (2025). Synthesis of Plant-Based Ester for Metalworking Fluids and Tribological Performance. Duzce University Journal of Science and Technology, 13(1), 430-442. https://doi.org/10.29130/dubited.1501022
AMA Kaya E. Synthesis of Plant-Based Ester for Metalworking Fluids and Tribological Performance. DUBİTED. January 2025;13(1):430-442. doi:10.29130/dubited.1501022
Chicago Kaya, Ertuğrul. “Synthesis of Plant-Based Ester for Metalworking Fluids and Tribological Performance”. Duzce University Journal of Science and Technology 13, no. 1 (January 2025): 430-42. https://doi.org/10.29130/dubited.1501022.
EndNote Kaya E (January 1, 2025) Synthesis of Plant-Based Ester for Metalworking Fluids and Tribological Performance. Duzce University Journal of Science and Technology 13 1 430–442.
IEEE E. Kaya, “Synthesis of Plant-Based Ester for Metalworking Fluids and Tribological Performance”, DUBİTED, vol. 13, no. 1, pp. 430–442, 2025, doi: 10.29130/dubited.1501022.
ISNAD Kaya, Ertuğrul. “Synthesis of Plant-Based Ester for Metalworking Fluids and Tribological Performance”. Duzce University Journal of Science and Technology 13/1 (January 2025), 430-442. https://doi.org/10.29130/dubited.1501022.
JAMA Kaya E. Synthesis of Plant-Based Ester for Metalworking Fluids and Tribological Performance. DUBİTED. 2025;13:430–442.
MLA Kaya, Ertuğrul. “Synthesis of Plant-Based Ester for Metalworking Fluids and Tribological Performance”. Duzce University Journal of Science and Technology, vol. 13, no. 1, 2025, pp. 430-42, doi:10.29130/dubited.1501022.
Vancouver Kaya E. Synthesis of Plant-Based Ester for Metalworking Fluids and Tribological Performance. DUBİTED. 2025;13(1):430-42.