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The course of epoxidation of sesame oil (SO) with performic acid formed „in situ” by the reaction of 30 wt% hydrogen peroxide and formic acid in the presence of sulfuric acid(VI) as a catalyst was studied. The most advantageous of the technological independent parameters of epoxidation are as follows: temperature 80°C, H2O2 C=C 3.5:1, HCOOH/C=C 0.8:1, amount of catalyst as H2SO4 /(H2O2 +HCOOH) 1 wt%, stirring speed at least 700 rpm, reaction time 6 h. The iodine number (IN), epoxy number (EN), a relative conversion to oxirane (RCO) and oxirane oxygen content (EOe) were determined every hour during the reaction. Under optimal conditions the sesame oil conversion amounted to 90.7%, the selectivity of transformation to epoxidized sesame oil was equal to 93.2%, EN = 0.34 mol/100 g, IN = 0.04 mol/100 g oil (10.2 g/100 g oil), a relative conversion to oxirane RCO = 84.6%, and oxirane oxygen content of EOe = 5.5%.
Słowa kluczowe
Czasopismo
Rocznik
Tom
Strony
53--59
Opis fizyczny
Bibliogr. 32 poz., rys., tab.
Twórcy
autor
- West Pomeranian University of Technology Szczecin, Institute of Organic Chemical Technology, Faculty of Chemical Technology and Engineering, Pułaskiego 10, 70-322 Szczecin, Poland
autor
- West Pomeranian University of Technology Szczecin, Institute of Organic Chemical Technology, Faculty of Chemical Technology and Engineering, Pułaskiego 10, 70-322 Szczecin, Poland
autor
- West Pomeranian University of Technology Szczecin, Institute of Organic Chemical Technology, Faculty of Chemical Technology and Engineering, Pułaskiego 10, 70-322 Szczecin, Poland
Bibliografia
- 1. Gan, L.H., Ooi, K.S., Goh, S.H., Gan, L.M. & Leong, Y.C. (1995). Epoxidized esters of palm olein as plasticizers for poly(vinyl chloride). Europ. Polym. J. 31, 719–724. DOI: 10.1016/0014-3057(95)00031-3.
- 2. Bunker, S.P. & Wool, R.P. (2002). Synthesis and characterization of monomers and polymers for adhesives from methyl oleate. J. Polym. Sci. Part A: Polym. Chem. 40, 451–458. DOI: 10.1002/pola.10130.
- 3. Petrović, Z.S., Zlatanić, A., Lava, C.C. & Sinadović-Fišer, 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. DOI: 10.1002/1438-9312(200205)104:5<293::AIDEJLT293>3.0.CO;2-W.
- 4. Meshram, P.D., Puri, R.G. & Patil, H.V. (2011). Epoxidation of wild safflower (carthamus oxyacantha) oil with peroxy acid in presence of strongly acidic cation exchange resin IR-122 as catalyst. Int. J. Chem. Tech. Res. 3(3), 1152–1163.
- 5. Goud, V.V., Patwardhan, A.V., Dinda, S. & Pradhan, N.C. (2007). Epoxidation of karanja (Pongamia glabra) oil catalyzed by acidic ion exchange resin. Eur. J. Lipid. Sci. Technol. 109, 575–584. DOI: 10.1002/ejlt.200600298.
- 6. Gurbanov, M.Sh., Mamedov, B.A. (2009). Epoxidation of flax oil with hydrogen peroxide in a conjugate system in the presence of acetic acid and chlorinated cation exchanger KU-2x8 as catalyst. Russ. J. Appl. Chem. 82(8), 1483–1487. DOI: 10.1134/S1070427209080308.
- 7. Poli, E., Clacens, J.M., Barrault, J., Pouilloux, Y. (2009). Solvent-free selective epoxidation of fatty esters over a tungstenbased catalyst. Catal. Today. 140(1–2), 19–22. DOI: 10.1016/j.cattod.2008.07.004.
- 8. Benaniba, M.T., Belhaneche-Bensemra, N. & Gelbard, G. (2007). Kinetics of tungsten-catalyzed sunflower oil epoxidation studied by 1H NMR. Eur. J. Lipid Sci. Technol. 109(12), 1186–1193. DOI: 10.1002/ejlt.200700114.
- 9. Rios, L.A., Weckes, P., Schuster, H. & Hoelderich, W.F. (2005). Mesoporous and amorphous Ti-silicas on the epoxidation of vegetable oils. J. Catal. 232(1), 19–26. DOI: 10.1016/j.jcat.2005.02.011.
- 10. Ye, X., Jiang, P., Zhang, P., Dong, Y., Jia, Ch., Zhang, X. & Xu, H. (2010). Novel Ti and mesoporous molecular sieves: synthesis, characterization and catalytic activity in the epoxidation of vegetable oil. Catal. Lett. 137(1–2), 88–93. DOI: 10.1007/s10562-010-0334-z.
- 11. Gerbase, E., Gregório, J.R., Martinelli, M., Brasil, M.C. & Mendes, A.N.F. (2002). Epoxidation of soybean oil by the methyltrioxorenium CH2Cl2/H2O2 catalytic biphasic system. J. Am. Oil Chem. Soc. 79(2), 179–181. DOI: 10.1007/s11746-002-0455-0.
- 12. Rüsch gen. Klaas, M. & Warwel, S. (1999). Complete and partial epoxidation of plant oils by lipase-catalyzed perhydrolysis. Ind. Crop. Prod. 9(2), 125–132. DOI: 10.1016/S0926-6690(98)00023-5.
- 13. Milchert, E., Malarczyk, K. & Kłos, M. (2015). Technological Aspects of Chemoenzymatic Epoxidation of Fatty Acids, Fatty Acid Esters and Vegetable Oils: A Review. Molecules 20(12), 21481–21493. DOI: 10.3390/molecules201219778.
- 14. Metzger, J.O. & Bornscheuer, U.T. (2006). Lipids as renewable resources: Current state of chemical and biotechnological conversion and divesification. Appl. Microbiol. Biotechnol. 71(1), 13–22. DOI: 10.1007/s00253-006-0335-4.
- 15. Tan, S.G. & Chow, W.S. (2010). Biobased Epoxidized Vegetable Oils and Its Greener Epoxy Blends: A Review. Polym. Plast. Technol. Eng. 49(15), 1581–1590. DOI: 10.1080/03602559.2010.512338.
- 16. Patil, H., Waghmare, J. (2013). Catalyst for epoxidation of oils: a review. Discovery 3(7), 10–14.
- 17. Bang Hyo-Jeong, Kim Cheong-Tae, Byung Hee Kim (2014). Liquid and gas chromatographic analyses of triacylglycerols for Asian sesame oil traceability. Eur. J. Lipid Sci. Technol. 116(10), 1354–1362. DOI: 10.1002/ejlt.201400089.
- 18. Saydut, A., Duz, M.Z., Kaya, C., Kafadar, C. & Hamamci, A.B. (2008). Transesterified sesame (Sesamum indicum L.) seed oil as a biodiesel fuel. Bioresource Technol. 99(14), 6656–6660. DOI: 10.1016/j.biortech.2007.11.063.
- 19. Mohamed, H.M.A. & Awatif, I.I. (1998). The use of sesame oil unsaponiftable matter as a natural antioxidant. Food Chem. 62 (3), 269–276. DOI: 10.1016/S0308-8146(97)00193-3.
- 20. Mordret, F. (1968). Detection of sesame oil. J. Crops Grass 6, 389–397.
- 21. Filippis, P.D., Scarsella, M. & Verdone, N. (2009). Peroxyformic acid formation: a kinetic study. Ind. Eng. Chem. Res. 48(3), 1372–1375. DOI: 10.1021/ie801163j.
- 22. Musik, M. & Michert, E. (2017). Selectice epoxidation of sesame oil with peracetic acid. Mol. Catalysis 433, 170–174. DOI: 10.1016/j.mcat.2017.02.012.
- 23. International standard EN ISO 5508, Analysis by gas chromatography of methyl esters of fatty acids.
- 24. International standard EN ISO 3961, Animal and vegetable fats and oils. Determination of iodine value.
- 25. International standard EN ISO 3001, Plastics, epoxy compounds. Determination of epoxy equivalent.
- 26. Gupta, S.S., Guchhait, A., Sarkar, S. & Ghosh, M. (2016). Comparative evaluation of the physico-chemical properties of chemically and enzymatically epoxidised soybean oil. Int. Res. J. Chem. 1(2), 17–24.
- 27. Mungroo, R., Pradhan, N.C., Goud, V.V. & Dalai, A.K. (2008). Epoxidation of canola oil with hydrogen peroxide catalyzed by acidic ion exchange resin. J. Am. Oil Chem. Soc. 85(9), 887–896. DOI: 10.1007/s11746-008-1277-z.
- 28. Goud, V.V., Dinda, S., Patwardhan, A.V. & Pradhan, N.C. (2010). Epoxidation of jatropha (Jatropha curcas) oil by peroxyacids. Asia-Pacyfi c J. Chem. Eng. 5(2), 346–354. DOI: 10.1002/apj.285.
- 29. Stenmark, G.A. (1958). Determination of alpha-glycol content of epoxy resins. Anal. Chem. 30(3), 381–383. DOI: 10.1021/ac60135a020.
- 30. Goud, V.V., Patwardhan, A.V. & Pradhan, N.C. (2006). Studies on the epoxidation of mahua oil (Madhumica indica) by hydrogen peroxide. Bioresource Technol. 97(12), 1365–1371. DOI: 10.1016/j.biortech.2005.07.004.
- 31. Moreno, V.C., Russo, V., Tesser, R. & Serio, M.D., Salzano E. (2017). Thermal risk in semi-batch reactors: the epoxidation of soybean oil. Process Saf. Environ. Prot.109, 529–537. DOI: 10.1016/j.psep.2017.05.001.
- 32. Leveneur, S. (2017). Thermal safety assessment through the concept of structure-reactivity: application to vegetable oil valorization. Org. Process Res. Dev. 21(4), 543–550. DOI: 10.1021/acs.oprd.6b00405.
Uwagi
Opracowanie rekordu w ramach umowy 509/P-DUN/2018 ze środków MNiSW przeznaczonych na działalność upowszechniającą naukę (2018).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-8d960bf2-12f9-4dab-9dc0-0a8f3f64208d