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Partially Dehydrated Castor Oil-Based Isoalkyl and Polyol Esters as Potential Base Stocks for Industrial Applications
Corresponding Author(s) : Siddaiah Vidavalur
Asian Journal of Chemistry,
Vol. 34 No. 7 (2022): Vol 34 Issue 7, 2022
Abstract
Partially dehydrated castor oil (PDCO) which is of less use in the paint and furniture coating formulations has been modified to develop biolubricant base stocks. PDCO (44.1%, non-conjugated linoleic acid; 32%, conjugated linoleic acid (18:2) isomers and 15.3% ricinoleic acid) obtained from a local industry was hydrolyzed under alkaline conditions. The fatty acids obtained (PDCFAs) in 98% yields were reacted with polyols namely 2-ethyl hexanol, neopentyl glycol, trimethylol propyl, pentaerythritol to obtain respective isoalkyl erters and esters of polyol with >95% yield. The base stocks exhibited very high viscosity indices (187.288 to 187.687), excellent pour point (-25 to -40 ºC) and high flash points (212 to 317 ºC) required for a variety of industrial applications namely metal working, hydraulic, forging, cutting fluid, gear oil applications. The tribological properties of PDCO, exhibited very low WSD (0.72-0.79 mm) and WSVs (0.82-0.83 mm3) with high load carrying capacities (180-220 kg) indicating low friction and less energy losses between the sliding surfaces. This was also accompanied by very high thermo-oxidation stabilities [Oxidation stability (230-242 ºC); Onset temperature (300-381 ºC)] of the base stacks due to branching. Overall all the PDCO isoalkyl and polyol esters exhibited excellent properties suitable for a wide range of industrial applications on par with mineral oil based lubricants.
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- C.H. Chan, S.W. Tang, N.K. Mohd, W.H. Lim, S.K. Yeong and Z. Idris, Renew. Sustain. Energy Rev., 93, 145 (2018); https://doi.org/10.1016/j.rser.2018.05.024
- Directive 2009/28/ec of the European Parliament and of the Council on the Promotion of the Use of Energy from Renewable Sources and Amending and Subsequently Repealing Directives 2001/77/EC and 2003/30/EC.
- https://www.financialexpress.com/economy/not-only-crude-indiaheavily-depends-on-dible-oil-imports-too-heres-why-there-isproduction crisis/1860047/
- D.S. Ogunniyi, Bioresour. Technol., 97, 1086 (2006); https://doi.org/10.1016/j.biortech.2005.03.028
- H. Mutlu and M.A.R. Meier, Eur. J. Lipid Sci. Technol., 112, 10 (2010); https://doi.org/10.1002/ejlt.200900138
- W. George, J. Priest and J.D. Von Mikusch, Ind. Eng. Chem., 32, 1314 (1940); https://doi.org/10.1021/ie50364a018.
- O. Grummitt and D. Marsh, J. Am. Oil Chem. Soc., 30, 21 (1953); https://doi.org/10.1007/BF02639914
- V. Atimuttigul, S. Damrongsakkul and W. Tanthapanichakoon, Korean J. Chem. Eng., 23, 672 (2006); https://doi.org/10.1007/BF02706813
- K. Kamalakar, G. Mahesh, R.B.N. Prasad and M.S.L. Karuna, J. Oleo Sci., 64, 1283 (2015); https://doi.org/10.5650/jos.ess15133
- V. Yelchuri, T. Azmeera and M.S.L. Karuna, SN Appl. Sci., 1, 1214 (2019); https://doi.org/10.1007/s42452-019-1263-0
- A. Sammaiah, K.V. Padmaja and R.B.N. Prasad, Indian Patent 2466/DEL/2014 (2014).
- K. Kamalakar, A.K. Rajak, R.B.N. Prasad and M.S.L. Karuna, Ind. Crops Prod., 51, 249 (2013); https://doi.org/10.1016/j.indcrop.2013.08.058
- Acid Value of Fats and Oils, In: Official Methods and Recommended Practices of the AOCS, 5th ed, Champaign, Illinois, AOCS Cd 3d-53 (2009).
- Iodine Value of Fats and Oils, In: Official Methods and Recommended Practices of the AOCS, 5th ed., Champaign, Illinois, AOCS Cd 1-25 (2003).
- Hydroxyl Values of Fatty Oils and Alcohols, In: Official Methods and Recommended Practices of the AOCS, 5th ed., Champaign, Illinois, AOCS Cd 13-60 (1997).
- Saponification Value, In: Official Methods and Recommended Practices of the AOCS, 5th ed, Champaign, Illinois, AOCS Cd 3-25 (2003).
- Oxirane Oxygen in Epoxidized Materials, In: Official Methods and Recommended Practices of the AOCS, 5th ed., Champaign, Illinois, AOCS Cd 9-57 (1997).
- Standard Test Method for Density, Relative Density and API Gravity of Liquids by Digital Density Meter, ASTM International, ASTM D 4052 (2011).
- Standard Test Method for Kinematic Viscosity of Transparent and Opaque Liquids, ASTM International, ASTM D 445-10 (1998).
- Viscosity Index Standard Practice for Calculating Viscosity Index from Kinematic Viscosity at 40 and 100 ºC, ASTM International, ASTM D 2270-0501 (1991).
- Standard test Method Flash Point by Pensky-martens Closed Cup Tester, ASTM International, ASTM D 93 (2002).
- Standard Test Method for Pour Point of Petroleum Products, ASTM International, ASTM D 97 (2005).
- Standard Test Method for Corrosiveness to Copper from Petroleum Products by Copper Strip Test, ASTM International, ASTM D 130 (2004).
- Standard Test Methods for Oxidation Onset Temperature of Hydrocarbons by Differential Scanning Calorimetry, ASTM International, ASTM E 2009-08 (2009).
- A. Sammaiah, K.V. Padmaja and R.B.N. Prasad, Eur. J. Lipid Sci. Technol., 118, 486 (2016); https://doi.org/10.1002/ejlt.201500109
- Determination of Extreme Pressure and Anti-Wear Properties of Lubricants-Four Ball Machine Method, ASTM International, ASTM IP 239 (2002).
- Standard Test Method for Wear Preventive Characteristics of Lubricating Fluid (Four Ball Method), ASTM International, ASTM D 4172 (2002).
- G. Gorla, S.M. Kour, K.V. Padmaja, M.S.L. Karuna and R.B.N. Prasad, Ind. Eng. Chem. Res., 52, 16598 (2013); https://doi.org/10.1021/ie4024325
- G. Gorla, S.M. Kour, K.V. Padmaja, M.S.L. Karuna and R.B.N. Prasad, Ind. Eng. Chem. Res., 53, 8685 (2014); https://doi.org/10.1021/ie5009986
- E.R. Booser, Eds.: M.H. Grant, Lubrication and Lubricants; In: Kirk’s Othmer Encyclopedia of Chemical Technology, Wiley-Interscience Chichester, U.K., Ed. 4, vol. 15, p. 463 (1992).
- R. Leslie, Rudnick, Synthetics, Mineral Oils, and Bio-Based Lubricants, 3rd Edition, Chemistry and Technology, CRC Press, Ed.: 3 (2020).
- N.W.M. Zulkifli, M.A. Kalam, H.H. Masjuki, M. Shahabuddin and R. Yunus, Energy, 54, 167 (2013); https://doi.org/10.1016/j.energy.2013.01.038
References
C.H. Chan, S.W. Tang, N.K. Mohd, W.H. Lim, S.K. Yeong and Z. Idris, Renew. Sustain. Energy Rev., 93, 145 (2018); https://doi.org/10.1016/j.rser.2018.05.024
Directive 2009/28/ec of the European Parliament and of the Council on the Promotion of the Use of Energy from Renewable Sources and Amending and Subsequently Repealing Directives 2001/77/EC and 2003/30/EC.
https://www.financialexpress.com/economy/not-only-crude-indiaheavily-depends-on-dible-oil-imports-too-heres-why-there-isproduction crisis/1860047/
D.S. Ogunniyi, Bioresour. Technol., 97, 1086 (2006); https://doi.org/10.1016/j.biortech.2005.03.028
H. Mutlu and M.A.R. Meier, Eur. J. Lipid Sci. Technol., 112, 10 (2010); https://doi.org/10.1002/ejlt.200900138
W. George, J. Priest and J.D. Von Mikusch, Ind. Eng. Chem., 32, 1314 (1940); https://doi.org/10.1021/ie50364a018.
O. Grummitt and D. Marsh, J. Am. Oil Chem. Soc., 30, 21 (1953); https://doi.org/10.1007/BF02639914
V. Atimuttigul, S. Damrongsakkul and W. Tanthapanichakoon, Korean J. Chem. Eng., 23, 672 (2006); https://doi.org/10.1007/BF02706813
K. Kamalakar, G. Mahesh, R.B.N. Prasad and M.S.L. Karuna, J. Oleo Sci., 64, 1283 (2015); https://doi.org/10.5650/jos.ess15133
V. Yelchuri, T. Azmeera and M.S.L. Karuna, SN Appl. Sci., 1, 1214 (2019); https://doi.org/10.1007/s42452-019-1263-0
A. Sammaiah, K.V. Padmaja and R.B.N. Prasad, Indian Patent 2466/DEL/2014 (2014).
K. Kamalakar, A.K. Rajak, R.B.N. Prasad and M.S.L. Karuna, Ind. Crops Prod., 51, 249 (2013); https://doi.org/10.1016/j.indcrop.2013.08.058
Acid Value of Fats and Oils, In: Official Methods and Recommended Practices of the AOCS, 5th ed, Champaign, Illinois, AOCS Cd 3d-53 (2009).
Iodine Value of Fats and Oils, In: Official Methods and Recommended Practices of the AOCS, 5th ed., Champaign, Illinois, AOCS Cd 1-25 (2003).
Hydroxyl Values of Fatty Oils and Alcohols, In: Official Methods and Recommended Practices of the AOCS, 5th ed., Champaign, Illinois, AOCS Cd 13-60 (1997).
Saponification Value, In: Official Methods and Recommended Practices of the AOCS, 5th ed, Champaign, Illinois, AOCS Cd 3-25 (2003).
Oxirane Oxygen in Epoxidized Materials, In: Official Methods and Recommended Practices of the AOCS, 5th ed., Champaign, Illinois, AOCS Cd 9-57 (1997).
Standard Test Method for Density, Relative Density and API Gravity of Liquids by Digital Density Meter, ASTM International, ASTM D 4052 (2011).
Standard Test Method for Kinematic Viscosity of Transparent and Opaque Liquids, ASTM International, ASTM D 445-10 (1998).
Viscosity Index Standard Practice for Calculating Viscosity Index from Kinematic Viscosity at 40 and 100 ºC, ASTM International, ASTM D 2270-0501 (1991).
Standard test Method Flash Point by Pensky-martens Closed Cup Tester, ASTM International, ASTM D 93 (2002).
Standard Test Method for Pour Point of Petroleum Products, ASTM International, ASTM D 97 (2005).
Standard Test Method for Corrosiveness to Copper from Petroleum Products by Copper Strip Test, ASTM International, ASTM D 130 (2004).
Standard Test Methods for Oxidation Onset Temperature of Hydrocarbons by Differential Scanning Calorimetry, ASTM International, ASTM E 2009-08 (2009).
A. Sammaiah, K.V. Padmaja and R.B.N. Prasad, Eur. J. Lipid Sci. Technol., 118, 486 (2016); https://doi.org/10.1002/ejlt.201500109
Determination of Extreme Pressure and Anti-Wear Properties of Lubricants-Four Ball Machine Method, ASTM International, ASTM IP 239 (2002).
Standard Test Method for Wear Preventive Characteristics of Lubricating Fluid (Four Ball Method), ASTM International, ASTM D 4172 (2002).
G. Gorla, S.M. Kour, K.V. Padmaja, M.S.L. Karuna and R.B.N. Prasad, Ind. Eng. Chem. Res., 52, 16598 (2013); https://doi.org/10.1021/ie4024325
G. Gorla, S.M. Kour, K.V. Padmaja, M.S.L. Karuna and R.B.N. Prasad, Ind. Eng. Chem. Res., 53, 8685 (2014); https://doi.org/10.1021/ie5009986
E.R. Booser, Eds.: M.H. Grant, Lubrication and Lubricants; In: Kirk’s Othmer Encyclopedia of Chemical Technology, Wiley-Interscience Chichester, U.K., Ed. 4, vol. 15, p. 463 (1992).
R. Leslie, Rudnick, Synthetics, Mineral Oils, and Bio-Based Lubricants, 3rd Edition, Chemistry and Technology, CRC Press, Ed.: 3 (2020).
N.W.M. Zulkifli, M.A. Kalam, H.H. Masjuki, M. Shahabuddin and R. Yunus, Energy, 54, 167 (2013); https://doi.org/10.1016/j.energy.2013.01.038