Grasas y Aceites, Vol 64, No 1 (2013)

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

M. Mushtaq
Chemical Engineering Department, Universiti Technologi PETRONAS, Malaysia

Isa M. Tan
Chemical Engineering Department, Universiti Technologi PETRONAS, Malaysia

M. Nadeem
Subsurface Technology, PETRONAS Research Sdn. Bhd (PRSB), Malaysia

C. Devi
Chemical Engineering Department, Universiti Technologi PETRONAS, Malaysia

S. Y. C. Lee
Chemical Engineering Department, Universiti Technologi PETRONAS, Malaysia

M. Sagir
Chemical Engineering Department, Universiti Technologi PETRONAS, Malaysia

U. Rashid
Institute of Advanced Technology, Universiti Putra Malaysia, Malaysia


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.


Characterization; Epoxidised Jatropha oil; Optimization; Response surface methodology

Full Text:



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.

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.

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.

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.

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.

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.

Dahlke B, Hellbardt S, Paetow MZW. 1995. Polyhydroxy fatty acids and their derivatives from plant oils. J. Am. Oil Chem. Soc. 72, 349-353.

Doll K, Erhan S. 2006. Synthesis and performance of surfactants based on epoxidized methyl oleate and glycerol. J. Surfactants Deterg. 9, 377-383.

Du G, Tekin A, Hammond E, Wood L. 2004. Catalytic epoxidation of methyl linoleate. J. Am. Oil Chem. Soc. 81, 477-480.

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.

Ghadge SV, Raheman H. 2006. Process optimization for biodiesel production from mahua (Madhuca indica) oil using response surface methodology. Bioresour. Technol. 97, 379-384. 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.

Goud V, Pradhan N, Patwardhan A. 2006. Epoxidation of karanja (Pongamia glabra) oil by H2O2. J. Am. Oil Chem. Soc. 83, 635-640.

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.

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.

Guillén MD, Cabo N. 1997b. Infrared spectroscopy in the study of edible oils and fats. J. Sci. Food Agric. 75, 1-11.<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.

Jiang ST, Niu L. 2011. Optimization and evaluation of wheat germ oil extracted by supercritical CO2. Grasas Aceites 62, 181-189.

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.

Kleinová A, Fodran P, Brncalová, Cvengros J. 2008. Substituted esters of stearic acid as potential lubricants. Biomass Bioenerg. 32, 366-371.

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.

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.

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.

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.<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.

Seniha-Güner F, Yagci Y, Tuncer-Erciyes A. 2006. Polymers from triglyceride oils. Prog. Polym. Sci. 31, 633-670.

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.

Vlek T, Petrovi Z. 2006. Optimization of the chemoenzymatic epoxidation of soybean oil. J. Am. Oil Chem. Soc. 83, 247-252.

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. PMid:9177726

Copyright (c) 2013 Consejo Superior de Investigaciones Científicas (CSIC)

Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.

Contact us

Technical support