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Epoxy Acyloxy Castor Polyol Esters: Multifunctional Base Oil for Aviation to Marine Formulations

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Abstract

With an intention to develop base oils with multi-functional properties, about 16 epoxy acyloxy castor polyol esters were prepared. Acyloxy castor polyols were prepared by the acylation of hydroxy functionality of castor fatty acids (acetylated, propionylated, butanoylated and hexanoylated) using kieselguhr-G method followed by reaction with polyols namely trimethylolpropane (TMP), neopentyl glycol (NPG), pentaerythritol (PE) and 2-ethyl hexanol (2-EtH) in 95–98% yields. Acyloxy castor polyol esters were epoxidized at the double bond to yield epoxy acyloxy castor polyol esters in 98–99% yields. The base stocks were characterized by 1H and 13C NMR, ESI–MS. When evaluated for base oil properties, exhibited high viscosity indices (86.27 to 427.01), very low pour points (–52 to –42°C) and high oxidative (30 to 50 min) and thermal (200 to 335°C) stabilities. These base stocks with good viscosity properties can withstand heavy loads, supported by low wear scar diameter. Overall the base stocks with superior properties can find applications right from aviation to marine engine formulations.

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REFERENCES

  1. Karmakar, G., Ghosh, P., and Sharma, B.K., Lubricants, 2017, vol. 5, no. 4, pp. 44–61. https://doi.org/10.3390/lubricants5040044

  2. Kamalakar, K., Mahesh, G.V., Prasad, R.B.N., and Karuna, M.S.L., J. Oleo Sci., 2015, vol. 64, no. 12, pp. 1283–1295. https://doi.org/10.5650/jos.ess15133

    Article  CAS  Google Scholar 

  3. Wagner, H., Luther, R., and Mang, T., Appl. Cat. A: Gen., 2001, vol. 221, pp. 429–442. https://doi.org/10.1016/S0926-860X(01)00891-2

  4. Goyan, R.L., Melley, R.E., Wissner, P.A., and Ong, W.C., Lubric. Eng., 1998, vol. 54, no. 7, pp. 10–17. ISSN: 0024-7154

  5. Lehrang Biologisch Abbvaubare Schmierstoffe und Arbeits flussigkeiten Speziell auf Pflanzlicher Basis, Bauman, W., Bauman, K., and Kotal, P., Eds., Technische Akadamie Esslingen, 1997.

  6. Yunus, R., Fakhrul-Razi, A., Ooi, T.L., Iyuke, S.E., and Perez, J.M., Eur. J. Lipid Sci. Technol., 2004, vol. 106, pp. 52–60. https://doi.org/10.1002/ejlt.200300862

  7. Geethanjali, G., Kour, S.M., Padmaja, K.V., Karuna, M.S.L., and Prasad, R.B.N., Ind. Eng. Chem. Res., 2013, vol. 52, no. 47, pp. 16598–16605. https://doi.org/10.1021/ie4024325

  8. Kamalakar, K., Sai Manoj, G.N.V.T., Prasad, R.B.N., and Karuna, M.S.L., Ind. Crops and Prod., 2015, vol. 76, pp. 456–466. https://doi.org/10.1016/j.indcrop.2015.07.050

  9. Sammaiah, A., Padmaja, K.V., and Prasad, R.B.N., J. Oleo Sci., 2014, vol. 63, no. 6, pp. 637–643. https://doi.org/10.5650/jos.ess13172

    Article  CAS  Google Scholar 

  10. Chan, C.H., Tang, S.W., Mohd, N.K., Lim, W.H., Yeong, S.K., and Idris, Z., Renew. Sust. Energ. Rev., 2018, vol. 93, pp. 145–157. https://doi.org/10.1016/j.rser.2018.05.024

  11. Reeves, C.J., Menezes, P.L., Jen, T.C., and Lovell, M.R., Tribol. Int., 2015, vol. 90, pp. 123–134. https://doi.org/10.1016/j.triboint.2015.04.021

  12. Rani, S., Joy, M.L., and Nair, K.P., Ind. Crops Prod., 2015, vol. 65, pp. 328–333. https://doi.org/10.1016/j.indcrop.2014.12.020

  13. Lundgren, S.M., Persson, K., Mueller, G., Kronberg, B., Clarke, J., Chtaib, M., and Claesson, P.M., Langmuir, 2007, vol. 23, no. 21, pp. 10598–10602. https://doi.org/10.1021/la700909v

  14. Goud, V.V., Patwardhan, A.V., Dinda, S., and Pradhan, N.C., Eur. J. Lipid Sci. Technol., 2007, vol. 109, pp. 575–584. https://doi.org/10.1002/ejlt.200600298

  15. Meyer, P.P., Techaphattana, N., Manundawee, S., Sangkeaw, S., Junlakan, W., and Tongurai, C., Thammasat Int. J. Sci. Technol., 2008, vol. 13, pp. 1–5.

    Google Scholar 

  16. Hilker, I., Bothe, D., Pruss, J., and Warnecke, H.-J., Chem. Eng. Sci., 2001, vol. 56, pp. 427–432. https://doi.org/10.1016/S0009-2509(00)00245-1

  17. Cai, S.F., Wang, L.S., and Fan, C.L., Molecules, 2009, vol. 14, no. 8, pp. 2935–2946. https://doi.org/10.3390/molecules14082935

  18. Rusch, M. and Warwel, S., Ind. Crops Prod., 1999, vol. 9, pp. 125–132. https://doi.org/10.1016/S0926-6690(98)00023-5

  19. Padmaja, K.V., Rao, B.V.S.K., Reddy, R.K., Bhaskar, P.S., Singh, A.K., and Prasad, R.B.N., Ind. Crops Prod., 2012, vol. 35, pp. 237–240. https://doi.org/10.1016/j.indcrop.2011.07.005

  20. Schneider, M.P., J. Sci. Food Agric., 2006, vol. 86, pp. 1769–1780. https://doi.org/10.1002/jsfa.2559

  21. Harry-O’kuru, R.E., Biresaw, G., Cermak, S.C., Gordon, S.H., and Vermillion, K., J. Agric. Food Chem., 2011, vol. 59, pp. 4725–4735. https://doi.org/10.1021/jf104746v

  22. Cannon, G.S. and Kotowski, J.A., Patent US 6340658 B1, 2002.

  23. Bunker, S.P. and Wool, R.P., J. Polym. Sci. A. Polym. Chem., 2002, vol. 40, pp. 451–458. https://doi.org/10.1002/pola.10130

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ACKNOWLEDGMENTS

Authors would like to thank Director CSIR-IICT for the necessary laboratory facilities. IICT Communication Number: IICT/Pubs./2022/071.

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Correspondence to M. S. L. Karuna or Devarapaga Madhu.

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Azmeera, T., Kotte, K., Vidavalur, S. et al. Epoxy Acyloxy Castor Polyol Esters: Multifunctional Base Oil for Aviation to Marine Formulations. Pet. Chem. 62, 1273–1282 (2022). https://doi.org/10.1134/S0965544122070210

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