Epoxidation of methyl esters derived from Jatropha oil: An optimization study

Authors

  • M. Mushtaq Chemical Engineering Department, Universiti Technologi PETRONAS
  • Isa M. Tan Chemical Engineering Department, Universiti Technologi PETRONAS
  • M. Nadeem Subsurface Technology, PETRONAS Research Sdn. Bhd (PRSB)
  • C. Devi Chemical Engineering Department, Universiti Technologi PETRONAS
  • S. Y. C. Lee Chemical Engineering Department, Universiti Technologi PETRONAS
  • M. Sagir Chemical Engineering Department, Universiti Technologi PETRONAS
  • U. Rashid Institute of Advanced Technology, Universiti Putra Malaysia

DOI:

https://doi.org/10.3989/gya.084612

Keywords:

Characterization, Epoxidised Jatropha oil, Optimization, Response surface methodology

Abstract


The optimization of the epoxidation reaction of methyl esters obtained from Jatropha oil was appraised. Response surface methodology (RSM) based on a central composite rotatable design (CCRD) was employed for the experimental design. Four reaction variables namely hydrogen peroxide/ C=C mole ratio, formic acid/C=C mole ratio, reaction temperature and reaction time were evaluated. The optimum epoxidation conditions calculated by the quadratic model were 3.12 moles of hydrogen peroxide/C=C moles, 0.96 moles of formic acid/C=C moles, a reaction temperature of 70.0 °C and a reaction time of 277 minutes. A reaction optimized by the proposed process parameters provided a yield of 92.89 ± 1.29 wt.% with relatively improved reaction time. Hydrogen peroxide concentration and reaction temperature were found to be the most significant variables while reaction temperature and hydrogen peroxide showed strong interactions. The epoxidized methyl esters were analyzed using FT-IR, 1H NMR and 13C NMR techniques. This study suggested relatively higher molar ratio of formic acid required than was proposed in the literature.

Downloads

Download data is not yet available.

References

Aerts H, Jacobs P. 2004. Epoxide yield determination of oils and fatty acid methyl esters using 1H NMR. J. Am. Oil Chem. Soc. 81, 841-846. http://dx.doi.org/10.1007/s11746-004-0989-1

Anwar F, Zafar SN, Rashid, U. 2006. Characterization of Moringa oleifera seed oil from drought and irrigated regions of Punjab, Pakistan. Grasas Aceites 57, 160-168. http://dx.doi.org/10.3989/gya.2006.v57.i2.32

Aslan N. 2008. Application of response surface methodology and central composite rotatable design for modeling and optimization of a multi-gravity separator for chromite concentration. Powder Technol. 185, 80-86. http://dx.doi.org/10.1016/j.powtec.2007.10.002

Brossard-González CO, Ferrari RA, Pighinelli AL, Parka KJ. 2010. Preliminary evaluation of anhydrous ethanol as a solvent in the oilseed extraction of Jatropha curcas L. Grasas Aceites 61, 295-302.

Campanella, A.Baltanás, M. A. 2006. Degradation of the oxirane ring of epoxidized vegetable oils in liquidliquid heterogeneous reaction systems. Chem. Eng. J. 118, 141-152. http://dx.doi.org/10.1016/j.cej.2006.01.010

Campanella A, Fontanini C, Baltanas M. 2008a. High yield epoxidation of fatty acid methyl esters with performic acid generated in situ. Chem. Eng. J. 144, 466-475. http://dx.doi.org/10.1016/j.cej.2008.07.016

Campanella A, Fontanini C, Baltanás MA. 2008b. High yield epoxidation of fatty acid methyl esters with performic acid generated in situ. Chem. Eng. J. 144, 466-475. http://dx.doi.org/10.1016/j.cej.2008.07.016

Dahlke B, Hellbardt S, Paetow MZW. 1995. Polyhydroxy fatty acids and their derivatives from plant oils. J. Am. Oil Chem. Soc. 72, 349-353. http://dx.doi.org/10.1007/BF02541095

Doll K, Erhan S. 2006. Synthesis and performance of surfactants based on epoxidized methyl oleate and glycerol. J. Surfactants Deterg. 9, 377-383. http://dx.doi.org/10.1007/s11743-006-5016-x

Du G, Tekin A, Hammond E, Wood L. 2004. Catalytic epoxidation of methyl linoleate. J. Am. Oil Chem. Soc. 81, 477-480. http://dx.doi.org/10.1007/s11746-004-0926-3

Gan L, Goh S, Ooi K. 1992. Kinetic studies of epoxidation and oxirane cleavage of palm olein methyl esters. J. Am. Oil Chem. Soc. 69, 347-351. http://dx.doi.org/10.1007/BF02636065

Ghadge SV, Raheman H. 2006. Process optimization for biodiesel production from mahua (Madhuca indica) oil using response surface methodology. Bioresour. Technol. 97, 379-384. http://dx.doi.org/10.1016/j.biortech.2005.03.014 PMid:15908200

Goswami D, Basu JK, De S. 2012. Optimal hydrolysis of mustard oil to erucic acid: A biocatalytic approach. Chem. Eng. J. 181–182, 542-548. http://dx.doi.org/10.1016/j.cej.2011.11.070

Goud V, Pradhan N, Patwardhan A. 2006. Epoxidation of karanja (Pongamia glabra) oil by H2O2. J. Am. Oil Chem. Soc. 83, 635-640. http://dx.doi.org/10.1007/s11746-006-1250-7

Goud VV, Dinda S, Patwardhan AV, Pradhan NC. 2010. Epoxidation of Jatropha (Jatropha curcas) oil by peroxyacids. Asia-Pac. J. Chem. Eng. 5, 346-354.

Goud VV, Patwardhan AV, Dinda S, Pradhan NC. 2007. Kinetics of epoxidation of jatropha oil with peroxyacetic and peroxyformic acid catalysed by acidic ion exchange resin. Chem. Eng. Sci. 62, 4065-4076. http://dx.doi.org/10.1016/j.ces.2007.04.038

Guillén MD, Cabo N. 1997a. Characterization of edible oils and lard by fourier transform infrared spectroscopy. Relationships between composition and frequency of concrete bands in the fingerprint region. J. Am. Oil Chem. Soc. 74, 1281-1286. http://dx.doi.org/10.1007/s11746-997-0058-4

Guillén MD, Cabo N. 1997b. Infrared spectroscopy in the study of edible oils and fats. J. Sci. Food Agric. 75, 1-11. http://dx.doi.org/10.1002/(SICI)1097-0010(199709)75:1<1::AID-JSFA842>3.0.CO;2-R

Ibrahim HM, Abou-Arab AA, Abu-Salem FM. 2011. Antioxidant and antimicrobial effects of some natural plant extracts added to lamb patties during storage. Grasas Aceites 62, 139-148. http://dx.doi.org/10.3989/gya.066510

Jiang ST, Niu L. 2011. Optimization and evaluation of wheat germ oil extracted by supercritical CO2. Grasas Aceites 62, 181-189. http://dx.doi.org/10.3989/gya.078710

Khlebnikova T, Pai Z, Fedoseeva L, Mattsat Y. 2009. Catalytic oxidation of fatty acids. II. Epoxidation and oxidative cleavage of unsaturated fatty acid esters containing additional functional groups. React. Kinet. Catal. Lett. 98, 9-17. http://dx.doi.org/10.1007/s11144-009-0054-9

Kleinová A, Fodran P, Brncalová, Cvengros J. 2008. Substituted esters of stearic acid as potential lubricants. Biomass Bioenerg. 32, 366-371. http://dx.doi.org/10.1016/j.biombioe.2007.09.015

Kumar A, Sharma S. 2008. An evaluation of multipurpose oil seed crop for industrial uses (Jatropha curcas L.): A review. Ind. Crop. Prod. 28, 1-10. http://dx.doi.org/10.1016/j.indcrop.2008.01.001

Lin B, Yang L, Dai H, Yi, A. 2008. Kinetic Studies on Oxirane Cleavage of Epoxidized Soybean Oil by Methanol and Characterization of Polyols. J. Am. Oil Chem. Soc. 85, 113-117. http://dx.doi.org/10.1007/s11746-007-1187-5

Miyake Y, Yokomizo K, Matsuzaki N. 1998. Determination of unsaturated fatty acid composition by highresolution nuclear magnetic resonance spectroscopy. J. Am. Oil Chem. Soc. 75, 1091-1094.

Mungroo R, Pradhan NC, Goud VV, Dalai AK. 2008. Epoxidation of canola oil with hydrogen peroxide catalyzed by acidic ion exchange resin. J. Am. Oil Chem. Soc. 85, 887-896. http://dx.doi.org/10.1007/s11746-008-1277-z

Naidir F, Yunus R, Ramli I, Mohd-Ghazi TI. 2011. Response surface methodology for optimization of epoxidized trimethylolpropane ester synthesis from palm oil. Int. J. Chem. React. Eng. 9.

Petrovi ZS, Zlatani A, Lava CC, Sinadinovi-Fi?er S. 2002. Epoxidation of soybean oil in toluene with peroxoacetic and peroxoformic acids - kinetics and side reactions. Eur. J. Lipid Sci. Technol. 104, 293- 299. http://dx.doi.org/10.1002/1438-9312(200205)104:5<293::AID-EJLT293>3.0.CO;2-W

Rashid U, Ibrahim M, Ali S, Adil M, Hina S, Bukhari I H,Yunus R. 2012. Comparative study of the methanolysis and ethanolysis of maize oils using alkaline catalysts. Grasas Aceites 63, 35-43. http://dx.doi.org/10.3989/gya.06891

Seniha-Güner F, Yagci Y, Tuncer-Erciyes A. 2006. Polymers from triglyceride oils. Prog. Polym. Sci. 31, 633-670. http://dx.doi.org/10.1016/j.progpolymsci.2006.07.001

Sun S, Ke X, Cui L, Yang G, Bi Y, Song F, Xu X. 2011. Enzymatic epoxidation of Sapindus mukorossi seed oil by perstearic acid optimized using response surface methodology. Ind. Crop. Prod. 33, 676-682. http://dx.doi.org/10.1016/j.indcrop.2011.01.002

Vlek T, Petrovi Z. 2006. Optimization of the chemoenzymatic epoxidation of soybean oil. J. Am. Oil Chem. Soc. 83, 247-252. http://dx.doi.org/10.1007/s11746-006-1200-4

Wilson R, Smith R, Wilson P, Shepherd MJ, Riemersma RA. 1997. Quantitative gas chromatography-mass spectrometry isomer-specific measurement of hydroxy fatty acids in biological samples and food as a marker of lipid peroxidation. Anal. Biochem. 248, 76-85. http://dx.doi.org/10.1006/abio.1997.2084 PMid:9177726

Downloads

Published

2013-03-30

How to Cite

1.
Mushtaq M, Tan IM, Nadeem M, Devi C, Lee SYC, Sagir M, Rashid U. Epoxidation of methyl esters derived from Jatropha oil: An optimization study. grasasaceites [Internet]. 2013Mar.30 [cited 2021Sep.19];64(1):103-14. Available from: https://grasasyaceites.revistas.csic.es/index.php/grasasyaceites/article/view/1414

Issue

Section

Research