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Optimization of the Ring Opening of Epoxidized Palm Oil using D-Optimal Design
Corresponding Author(s) : Nadia Salih
Asian Journal of Chemistry,
Vol. 33 No. 1 (2021): Vol 33 Issue 1
Abstract
In the presence of a catalyst, p-toluenesulfonic acid (PTSA), the ring of epoxidized palm oil (EPO) was opened using oleic acid (OA). The optimization effects of different process variables including the mol ratio of EPO/OA, reaction temperature, PTSA percentage and reaction time was performed by response surface methodology (RSM). To assess the effects of process variables and interactions among them, a D-optimal design was used as an RSM tool to acquire the maximum response value. The following are the optimum conditions achieved at the reaction time of 4.73 h in the RSM study: 1.02% PTSA, 3 EPO/OA mol ratio and 119.14 ºC reaction temperature. These conditions resulted in 84% yield, 0.041% oxirane oxygen content (OOC), 59.4 mg/g iodine value (IV), and 118.7 mg/g hydroxyl value (HV). The results are in a excellent agreement with the values predicted using a regression model.
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- A. Campanella, E. Rustoy, A. Baldessari and M.A. Baltanas, Bioresour.Technol., 101, 245 (2010); https://doi.org/10.1016/j.biortech.2009.08.035
- J. Salimon, N. Salih and E. Yousif, J. Saudi Chem. Soc.,15, 195 (2011);https://doi.org/10.1016/j.jscs.2010.08.00474
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- H. Schuster, L.A. Rios, P.P. Weckes and W.F. Hoelderich, Appl. Catal. A Gen., 348, 266 (2008); https://doi.org/10.1016/j.apcata.2008.07.004
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- H. Baumann, M. Bühler, H. Fochem, F. Hirsinger, H. Zoebelein and J.Falbe, Angew. Chem., 27, 41 (1988); https://doi.org/10.1002/anie.198800411
- J. Salimon, B.M. Abdullah and N. Salih, Arab. J. Chem., 9, S1053 (2016); https://doi.org/10.1016/j.arabjc.2011.11.002
- V. Von, Heterogeneously Catalyzed Reactions with Vegetable Oils: Epoxidation and Nucleophilic Epoxide Ring-Opening with Alcohols. M.Sc-Chemisch Ingenieur Luis Alberto Rios, Aus Medellin, Colombia (2002).
- J. Salimon, B.M. Abdullah, R.M. Yusop, N. Salih and E. Yousif, Springerplus, 2, 429 (2013); https://doi.org/10.1186/2193-1801-2-429
- V.B. Borugadda and V.V. Goud, Energy Sci. Eng., 3, 371 (2015); https://doi.org/10.1002/ese3.77
- D. Firestone, American Oil Chemists Society (AOCS), Standard Methods Ca 5a-40 for the Estimation of Free Fatty Acid Value, Official Methods and Recommended Practices of the American oil Chemists Society, Champaign, IL, USA: AOCS, edn 5 (1990).
- S.A. Hassanzadeh-Tabrizi and E. Taheri-Nassaj, J. Sol-Gel Sci. Technol., 57, 212 (2011); https://doi.org/10.1007/s10971-010-2344-0
- N.A.M. Aziz, R. Yunus, U. Rashid and A.M. Syam, Ind. Crops Prod.,62, 305 (2014); https://doi.org/10.1016/j.indcrop.2014.08.040
- P. Manivannan and M. Rajasimman, J. Food Process Eng., 34, 804 (2011); https://doi.org/10.1111/j.1745-4530.2009.00436.x
- A.A.W. Japir, J. Salimon, D. Derawi, M. Bahadi and M.R. Yusop, Asian J. Chem., 28, 2549 (2016); https://doi.org/10.14233/ajchem.2016.20095
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- J. Salimon, B.M. Abdullah and N. Salih, Chem. Cent. J., 6, 65 (2012); https://doi.org/10.1186/1752-153X-6-65
- M.A. Bahadi, J. Salimon, A.W.M. Japir and N. Salih, Malays. J. Anal. Sci., 20, 5 (2016).
- J. Salimon, M. Said, S. Ramli and M. Lazim, Oil and Fat Analysis,UKM Publishing: Bangi, Malaysia (2006).
- P.E. Sonnet and T.A. Foglia, J. Am. Oil Chem. Soc., 73, 461 (1996); https://doi.org/10.1007/bf02523919
- M.A. Bahadi, J. Salimon and A.W.M. Japir, AIP Conf. Proc., 1784, 030002 (2016); https://doi.org/10.1063/1.4966740
- B.K. Körbahti and A. Tanyolac, J. Hazard. Mater., 151, 422 (2008); https://doi.org/10.1016/j.jhazmat.2007.06.010
- G. Haraldsson, J. Am. Oil Chem. Soc., 61, 219 (1984); https://doi.org/10.1007/BF02678772
References
A. Campanella, E. Rustoy, A. Baldessari and M.A. Baltanas, Bioresour.Technol., 101, 245 (2010); https://doi.org/10.1016/j.biortech.2009.08.035
J. Salimon, N. Salih and E. Yousif, J. Saudi Chem. Soc.,15, 195 (2011);https://doi.org/10.1016/j.jscs.2010.08.00474
J. Salimon, N. Salih and B.M. Abdullah, J. Biomed. Biotechnol., 2012,1 (2012); https://doi.org/10.1155/2012/693848
H. Schuster, L.A. Rios, P.P. Weckes and W.F. Hoelderich, Appl. Catal. A Gen., 348, 266 (2008); https://doi.org/10.1016/j.apcata.2008.07.004
R. Wang and T.P. Schuman, eXPRESS Poly. Lett., 7, 272 (2013); https://doi.org/10.3144 expresspolymlett.2013.25
H. Baumann, M. Bühler, H. Fochem, F. Hirsinger, H. Zoebelein and J.Falbe, Angew. Chem., 27, 41 (1988); https://doi.org/10.1002/anie.198800411
J. Salimon, B.M. Abdullah and N. Salih, Arab. J. Chem., 9, S1053 (2016); https://doi.org/10.1016/j.arabjc.2011.11.002
V. Von, Heterogeneously Catalyzed Reactions with Vegetable Oils: Epoxidation and Nucleophilic Epoxide Ring-Opening with Alcohols. M.Sc-Chemisch Ingenieur Luis Alberto Rios, Aus Medellin, Colombia (2002).
J. Salimon, B.M. Abdullah, R.M. Yusop, N. Salih and E. Yousif, Springerplus, 2, 429 (2013); https://doi.org/10.1186/2193-1801-2-429
V.B. Borugadda and V.V. Goud, Energy Sci. Eng., 3, 371 (2015); https://doi.org/10.1002/ese3.77
D. Firestone, American Oil Chemists Society (AOCS), Standard Methods Ca 5a-40 for the Estimation of Free Fatty Acid Value, Official Methods and Recommended Practices of the American oil Chemists Society, Champaign, IL, USA: AOCS, edn 5 (1990).
S.A. Hassanzadeh-Tabrizi and E. Taheri-Nassaj, J. Sol-Gel Sci. Technol., 57, 212 (2011); https://doi.org/10.1007/s10971-010-2344-0
N.A.M. Aziz, R. Yunus, U. Rashid and A.M. Syam, Ind. Crops Prod.,62, 305 (2014); https://doi.org/10.1016/j.indcrop.2014.08.040
P. Manivannan and M. Rajasimman, J. Food Process Eng., 34, 804 (2011); https://doi.org/10.1111/j.1745-4530.2009.00436.x
A.A.W. Japir, J. Salimon, D. Derawi, M. Bahadi and M.R. Yusop, Asian J. Chem., 28, 2549 (2016); https://doi.org/10.14233/ajchem.2016.20095
J. Salimon, B.M. Abdullah and N. Salih, Chem. Cent. J., 5, 67 (2011); https://doi.org/10.1186/1752-153X-5-67
J. Salimon, B.M. Abdullah and N. Salih, Chem. Cent. J., 6, 65 (2012); https://doi.org/10.1186/1752-153X-6-65
M.A. Bahadi, J. Salimon, A.W.M. Japir and N. Salih, Malays. J. Anal. Sci., 20, 5 (2016).
J. Salimon, M. Said, S. Ramli and M. Lazim, Oil and Fat Analysis,UKM Publishing: Bangi, Malaysia (2006).
P.E. Sonnet and T.A. Foglia, J. Am. Oil Chem. Soc., 73, 461 (1996); https://doi.org/10.1007/bf02523919
M.A. Bahadi, J. Salimon and A.W.M. Japir, AIP Conf. Proc., 1784, 030002 (2016); https://doi.org/10.1063/1.4966740
B.K. Körbahti and A. Tanyolac, J. Hazard. Mater., 151, 422 (2008); https://doi.org/10.1016/j.jhazmat.2007.06.010
G. Haraldsson, J. Am. Oil Chem. Soc., 61, 219 (1984); https://doi.org/10.1007/BF02678772