Statistical optimization of the synthesis of plant-derived fatty acid esters of TMP over homogeneous organometallic tin catalyst

1. Erhan, S.Z. & Asadauskas, S. (2000) Lubricant basestocks from vegetable oils. Ind. Crop. Prod. 11, 277–282. DOI: 10.1016/S0926-6690(99)00061-8.10.1016/S0926-6690(99)00061-8Open DOISearch in Google Scholar

2. Alias, N.H., Yunus, R., Idris, A. & Omar, R. (2009) Effects of additives on oxidation characteristics of palm oil-based trimethylolpropane ester in hydraulics applications. Eur. J. Lipid Sci. Technol. 111, 368–375. DOI: 10.1002/ejlt.200800136.10.1002/ejlt.200800136Open DOISearch in Google Scholar

3. Pettersson, A. (2007) High-performance base fluids for environmentally adapted lubricants. Tribol. Int. 40, 638–645. DOI: 10.1016/j.triboint.2005.11.016.10.1016/j.triboint.2005.11.016Open DOISearch in Google Scholar

4. Kiriliauskaite, V., Bendikiene, V. & Juodka, B. (2011) Synthesis of trimethylolpropane esters of oleic acid by Lipoprime 50T. J. Ind. Microbiol. Biot. 38, 1561–1566. DOI: 10.1007/s10295-011-0946-3.10.1007/s10295-011-0946-3Open DOISearch in Google Scholar

5. Willing, A. (2001) Lubricants based on renewable resources – an environmentally compatible alternative to mineral oil products. Chemosphere 43, 89–98. DOI: 10.1016/S0045-6535(00)00328-3.10.1016/S0045-6535(00)00328-3Open DOISearch in Google Scholar

6. Nagendramma, P. (2011) Study of pentaerythritol tetraoleate ester as industrial gear oil Lubr. Sci. 23, 355–362. DOI: 10.1002/ls.161.10.1002/ls.161Open DOISearch in Google Scholar

7. McNutt, J. & He, Q. (2016) Development of biolubricants from vegetable oils via chemical modification. J. Ind. Eng. Chem. 36, 1–12. DOI: 10.1016/j.jiec.2016.02.008.10.1016/j.jiec.2016.02.008Open DOISearch in Google Scholar

8. Syahir, A.Z., Zulkifli, N.W.M., Masjuki, H.H., Kalam, M.A., Alabdulkarem, A, Gulzar, M., Khuong, L.S. & Harith, M.H. (2017) A review on bio-based lubricants and their applications. J. Clean. Sci. 168, 997–1016. DOI: 10.1016/j.jclepro.2017.09.106.10.1016/j.jclepro.2017.09.106Search in Google Scholar

9. Panchal, T.M., Patel, A., Chauhan, D.D., Thomas, M. &Pate, J.V. (2017) A methodological review on bio-lubricants from vegetable oil based resources. Renev. Sustain. Energ, Rev., 70, 65–70. DOI: 10.1016/j.rser.2016.11.105.10.1016/j.rser.2016.11.105Open DOISearch in Google Scholar

10. Zainal, N.A., Zulkifli, N.W.M., Gulzar, M. & Masjuki, H.H. (2018) A review on the chemistry, production, and technological potential of bio-based lubricants. Renev. Sustain. Energ, Rev., 82, 80–102.10.1016/j.rser.2017.09.004Search in Google Scholar

11. Bongardt, F., Bossmann, B., Westfechtel, A. & Giede, W. (1996) Synthetische ester aus alkoholen und fettsäuregemischen aus ölsäurereichen, stearinsäurearmen pflanzenölen. German Pat. DE 4444137.Search in Google Scholar

12. Lämsä, M. (1996) Process for preparing a synthetic ester from a vegetable oil. World Pat. WO 1996007632 A1.Search in Google Scholar

13. Leleu, G., Bédague, P. & Silion, S. (1977) Trimethylol-propane esters useful as base lubricants for motor oils. USA Pat. US 4061581.Search in Google Scholar

14. Tsai, M, Laemmle JT (1987) Metalworking with a trimethylolalkane ester lubricant. USA Pat US 4655947.Search in Google Scholar

15. Mattei, L., Pacor, P. & Piccone, A. (1995) Oils with Low Environmental Impact for Modern Combustion Engines. Synth. Lubr. 26,49–52. DOI: 10.1007/s11746-998-0094-8.10.1007/s11746-998-0094-8Open DOISearch in Google Scholar

16. Lawate, S.S. & Lal, L. (1998) High oleic polyol esters, compositions and lubricants, functional fluids and greases containing the same. USA Pat. US 5773391.Search in Google Scholar

17. Yunus, R., Fakhru’l-Razi, A., Ooi, T.L., Biak, D.L. & Iyuke, S.E. (2004) Kinetics of transesterification of palm-based methyl esters with trimethylolpropane. J. Am. Oil Chem. Soc. 81, 497–503. DOI: 10.1007/s11746-004-0930-7.10.1007/s11746-004-0930-7Open DOISearch in Google Scholar

18. Uosukainen, E., Linko, Y.Y., Lämsä, M., Tervakangas, T. & Linko, P. (1998) Transesterification of trimethylolpropane and rapeseed oil methyl ester to environmentally acceptable lubricants. J. Am. Oil Chem. Soc. 75, 1557–1563. DOI: 10.1007/s11746-998-0094-8.10.1007/s11746-998-0094-8Open DOISearch in Google Scholar

19. Wang, E., Ma, X., Tang, Sh., Yan, R., Wang, Y., Riley, W.W. & Reaney, M.J.T. (2014) Synthesis and oxidative stability of trimethylolpropane fatty acid triester as a biolubricant base oil from waste cooking oil. Biomass Bioenerg. 66, 371–378, DOI: 10.1016/j.biombioe.2014.03.022.10.1016/j.biombioe.2014.03.022Open DOISearch in Google Scholar

20. Chang, T., Yunus, R., Rashid, U., Choong, T. S.Y., Biak, D.R.A. & Syam, A.M. (2015) Palm Oil Derived Trimethylol-propane Triesters Synthetic Lubricants and Usage in Industrial Metalworking Fluid. J. Oleo Sci. 64, 143–151.10.5650/jos.ess1416225748374Search in Google Scholar

21. Hamid, H.A., Yunus, R., Rashid, U., Choong, T. S.Y., Ali, S. & Syam, A.M. (2016) Synthesis of high oleic palm oil--based trimethylolpropane esters in a vacuum operated pulsed loop reactor. Fuel, 166, 560–566.10.1016/j.fuel.2015.11.022Search in Google Scholar

22. Srinivas, D. & Kotwal, M. (2013) Process for preparing biodegradable lubricant base oils World Pat. WO 2013175509.Search in Google Scholar

23. Brini, S., Psaro, R., Zaccheria, F. & Ravasio, M.N. (2014) Process or the synthesis of esters of fatty acids in the presence of catalyst. World Pat. WO 201400659.Search in Google Scholar

24. Zaccheria, F., Mariani, M., Psaro, R., Bondioli, P. & Ravasio, N. (2016) Environmentally friendly lubricants through a zero waste process. Appl. Catal. B: Environ. 181, 581–586. DOI: 10.1016/j.apcatb.2015.08.032.10.1016/j.apcatb.2015.08.032Open DOISearch in Google Scholar

25. Kotwal, M., Kumar, A. & Darbha, S. (2013) Three-dimensional, mesoporous titanosilicates as catalysts for producing biodiesel and biolubricants. J. Mol. Catal. A, Chemical 377, 65–73. DOI: 10.1016/j.molcata.2013.04.029.10.1016/j.molcata.2013.04.029Open DOISearch in Google Scholar

26. Varhadi, P., Kotwal, M. & Srinivas, D. (2013) Zirconium phenyl phosphonate phosphite as a highly active, reusable, solid acid catalyst for producing fatty acid polyol. Appl. Catal. A: General 462–463, 129–136. DOI: 10.1016/j.apcata.2013.04.043.10.1016/j.apcata.2013.04.043Open DOISearch in Google Scholar

27. Oh, J., Yang, S., Kim, Ch., Choi, I., Kim, J. & Lee, H. (2013) Synthesis of biolubricants using sulfated zirconia catalysts. Appl Catal A: General 455, 164–171. DOI: 10.1016/j.apcata.2013.01.032.10.1016/j.apcata.2013.01.032Open DOISearch in Google Scholar

28. Nagendramma, P., Kaul, S. & Bisht, R.P.S. (2010) Study of synthesized ecofriendly and biodegradable esters: fire resistance and lubricating properties. Lubr. Sci. 22,103–110. DOI: 10.1002/ls.108.10.1002/ls.108Open DOISearch in Google Scholar

29. Linko, Y.Y., Tervakangas, T., Lamsa, M. & Linko, P. (1997) Production of trimethylolpropane esters of rapeseed oil fatty acids by immobilized lipase. Biotechnol. Tech. 11, 889–892. DOI: 10.1023/A:1018410316231.10.1023/A:1018410316231Open DOISearch in Google Scholar

30. Åkerman, C.O., Gaber, Y., Ghanid, N.A., Lämsäe, M. & Hatti-Kaul, R. (2011) Clean synthesis of biolubricants for low temperature applications using heterogeneous catalysts. J. Mol. Catal. B. Enzym. 72 263–269. DOI: 10.1016/j.molcatb.2011.06.014.10.1016/j.molcatb.2011.06.014Open DOISearch in Google Scholar

31. Åkerman, C.O., Hagström, A.E.V., Mollaahmad, M.A., Karlsson, S. & Hatti-Kaul, R. (2011) Biolubricant synthesis using immobilised lipase: Process optimization of trimethylol-propane oleate production. Process. Biochem. 46, 2225–2231. DOI: 10.1016/j.procbio.2011.08.006.10.1016/j.procbio.2011.08.006Open DOISearch in Google Scholar

32. Bongardt, F., Bossmann, B., Westfechtel, A. & Giede, W. (1996) Synthetische Ester aus Alkoholen und Fettsäuregemischen aus ölsäurereichen, stearinsäurearmen Pflanzenölen. German Pat. DE 4444137.Search in Google Scholar

33. Dai, J., Li, D., Zhao, Y. & Xiu, Zh. (2014) Statistical Optimization for Biodiesel Production from Soybean Oil in a Microchannel Reactor. Ind. Eng. Chem. Res. 53 9325–9330. DOI: DOI: 10.1021/ie4037005.10.1021/ie4037005Open DOISearch in Google Scholar

34. El-Gendy, N.S., Deriase, S.F. & Hamdy, A. (2014) Statistical optimization of biodiesel production from sunflower waste cooking oil using basic heterogeneous biocatalyst prepared from eggshells. Egypt J. Petrol. 24, 37–48. DOI: 10.1016/j.ejpe.2015.02.004.10.1016/j.ejpe.2015.02.004Open DOISearch in Google Scholar

35. Nowicki, J., Stańczyk, D., Drabik, J., Mosio-Mosiewski, J., Woszczyński, P. & Warzała, M. (2016) Synthesis of Fatty Acid Esters of Selected Higher Polyols Over Homogeneous Metallic Catalysts. J. Am. Oil Chem. Soc. 93, 973–981. DOI: 10.1007/s11746-016-2840-7.10.1007/s11746-016-2840-7491938627418694Open DOISearch in Google Scholar

36. Ash, M. & Ash, I. (2004) Handbook of Green Chemicals, Endicott NY, USA: Synapse Info Resources Inc.,Search in Google Scholar