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

Nowicki, Janusz; Drabik, Jolanta; Stańczyk, Dorota; Mosio-Mosiewski, Jan; Woszczyński, Piotr

doi:10.2478/pjct-2018-0024

Abstract

A class of very important industrial-grade biolubricants was synthesized from plant-derived fatty acids (oleic and isostearic acid) by direct esterification of trimethylolpropane according to novel effective and high selective method using Sn bis(2-ethylhexanoate) as catalyst. Model transesterification reactions were performed with oleic and isostearic acids to optimize the reaction conditions to obtain maximum content of TMP triesters. Used specific homogeneous Sn catalyst allows to obtain TMP esters with very high content of triesters, above of 94 wt% without deep vacuum purifying distillation. Both TMP esters were evaluated for their physicochemical and tribological properties using ASTM standards. Both TMP esters exhibited high viscosity indexes and excellent low temperature properties.

References

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)00061-8
Open DOI Search in Google Scholar Back to article
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.200800136
Open DOI Search in Google Scholar Back to article
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.2005.11.016
Open DOI Search in Google Scholar Back to article
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/s10295-011-0946-3
Open DOI Search in Google Scholar Back to article
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)00328-3
Open DOI Search in Google Scholar Back to article
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.161
Open DOI Search in Google Scholar Back to article
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.2016.02.008
Open DOI Search in Google Scholar Back to article
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.2017.09.106
Search in Google Scholar Back to article
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.2016.11.105
Open DOI Search in Google Scholar Back to article
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.2017.09.004
Search in Google Scholar Back to article
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 Back to article
12. Lämsä, M. (1996) Process for preparing a synthetic ester from a vegetable oil. World Pat. WO 1996007632 A1.
Search in Google Scholar Back to article
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 Back to article
14. Tsai, M, Laemmle JT (1987) Metalworking with a trimethylolalkane ester lubricant. USA Pat US 4655947.
Search in Google Scholar Back to article
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/s11746-998-0094-8
Open DOI Search in Google Scholar Back to article
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 Back to article
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/s11746-004-0930-7
Open DOI Search in Google Scholar Back to article
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/s11746-998-0094-8
Open DOI Search in Google Scholar Back to article
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.2014.03.022
Open DOI Search in Google Scholar Back to article
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.ess1416225748374
Search in Google Scholar Back to article
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.2015.11.022
Search in Google Scholar Back to article
22. Srinivas, D. & Kotwal, M. (2013) Process for preparing biodegradable lubricant base oils World Pat. WO 2013175509.
Search in Google Scholar Back to article
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 Back to article
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.2015.08.032
Open DOI Search in Google Scholar Back to article
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.2013.04.029
Open DOI Search in Google Scholar Back to article
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.2013.04.043
Open DOI Search in Google Scholar Back to article
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.2013.01.032
Open DOI Search in Google Scholar Back to article
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.108
Open DOI Search in Google Scholar Back to article
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:1018410316231
Open DOI Search in Google Scholar Back to article
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.2011.06.014
Open DOI Search in Google Scholar Back to article
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.2011.08.006
Open DOI Search in Google Scholar Back to article
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 Back to article
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/ie4037005
Open DOI Search in Google Scholar Back to article
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.2015.02.004
Open DOI Search in Google Scholar Back to article
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/s11746-016-2840-7491938627418694
Open DOI Search in Google Scholar Back to article
36. Ash, M. & Ash, I. (2004) Handbook of Green Chemicals, Endicott NY, USA: Synapse Info Resources Inc.,
Search in Google Scholar Back to article

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

Abstract

Paradigm

My account