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Technological aspects of vegetable oils epoxidation in the presence of ion exchange resins: a review

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Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
A review paper of the technology basics of vegetable oils epoxidation by means of peracetic or performic acid in the presence of acidic ion exchange resins has been presented. The influence of the following parameters: temperature, molar ratio of acetic acid and hydrogen peroxide to ethylenic unsaturation, catalyst loading, stirring intensity and the reaction time on a conversion of ethylenic unsaturation, the relative percentage conversion to oxirane and the iodine number was discussed. Optimal technological parameters, mechanism of epoxidation by carboxylic peracids and the possibilities of catalyst recycling have been also discussed. This review paper shows the application of epoxidized oils.
Rocznik
Strony
128--133
Opis fizyczny
Bibliogr. 47 poz., rys., tab.
Twórcy
autor
  • West Pomeranian University of Technology, Szczecin, Institute of Organic Chemical Technology, K. Pulaskiego 10, 70-322 Szczecin, Poland
  • West Pomeranian University of Technology, Szczecin, Institute of Organic Chemical Technology, K. Pulaskiego 10, 70-322 Szczecin, Poland, kornelia.malarczyk@zut.edu.pl
autor
  • West Pomeranian University of Technology, Szczecin, Institute of Organic Chemical Technology, K. Pulaskiego 10, 70-322 Szczecin, Poland
Bibliografia
  • 1. 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.
  • 2. Güner, F.S., Yağci, Y. & Erciyes, A.T. (2006). Polymers from Triglyceride oils. Prog. Polym. Sci. 31, 633-670. DOI: 10.1016/j.progpolymsci.2006.07.001.
  • 3. Alam, M., Akram, D., Sharmin, E., Zafar, F. & Ahmad, S. (2014). Vegetable oil based eco-friendly coating materials: A review article. Arab. J. Chem. 7, 469-479. DOI: 10.1016/j. arabjc.2013.12.023.
  • 4. Dinda, A., Patwarthan, A.V., Goud, V.V. & Pradhan, N.N. (2008). Epoxidation of cottonseed oil by aqueous hydrogen peroxide catalysed by liquid inorganic acids. Bioresour. Technol. 99, 3737-3744.
  • 5. 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.
  • 6. Rios, L.A., Weckes, P., Schuster, H. & Hoelderich, W.F. (2005). Mesoporous and amorphous Ti-silicas on the epoxidation of vegetable oils. J Catal. J. Catal. 232(1), 19-26. DOI: 10.1016/j.jcat.2005.02.011.
  • 7. Benaniba, M.T., Belhaneche-Bensemra, N. & Gelbard, G. (2003). Stabilization of PVC by epoxidized sunflower oil in the presence of zinc and calcium stearates. Polym. Degrad. Stabil. 82(2), 245-249. DOI: 10.1016/S0141-3910(03)00178-2.
  • 8. Saurabh, T., Patnaik, M., Bhagt, S.L. & Renge, V.C. (2011). Epoxidation of Vegetable Oils: A Review. Int. J. Adv. Eng. Technol. 2(4), 491-501.
  • 9. Metzger, J.O. & Bornscheuer, U. (2006). Lipids as renewable resources: current state of chemical and biotechnological conversion and diversifi cation. Appl. Microbiol. Biotechnol. 71(1), 13-22. DOI: 10.1007/s00253-006-0335-4.
  • 10. Piazza, G.J. & Foglia, T.A. (2005). Preparation of fatty amide polyols via epoxidation of vegetable oil amides by oat seed peroxygenase. J. Am. Oil Chem. Soc. 82(7), 481-485. DOI: 10.1007/s11746-005-1097-y.
  • 11. Gurbanov, M.S., Chalabiev, Ch.A., Mamedov, B.A. & Efendiev, A.A. (2005). Epoxidation of soybean oil in the course of cooxidation with hydrogen peroxide in the presence of propanoic acid and chlorinated KU-2 8 cation exchanger. Russ. J. Appl. Chem. 78, 1678-1681.
  • 12. Carlson, K.D. & Chang, S.P. (1985). Chemical epoxidation of a natural unsaturated epoxy seed oil from Vernonia galamensis and a look at epoxy oil markets. J. Am. Oil Chem. Soc. 62(5), 934-939. DOI: 10.1007/BF02541763.
  • 13. Hang, X. & Yang, H. (1999). Model for Cascade Continuous Epoxidation Process. J. Am. Oil Chem. Soc. 76, 89-92. DOI: 10.1007/s11746-999-0052-0.
  • 14. Lathi, P.S. & Mattiasson, B. (2007). Green approach for the preparation of biodegradable lubricant basestock from epoxidized vegetable oil. Appl. Catal. Envrion. 69, 207-212.
  • 15. Salimon, J., Abdullah, B.M., Yusop, R.M. & Salih, N. (2014). Synthesis, reactivity and application studies for different biolubricants Chem. Cent. J. 8(16), 1-11. DOI: 10.1186/1752-153X-8-16.
  • 16. Biswas, A., Adhvaryu, A., Gordon, S.H., Erhan S.Z. & Willett, J.L. (2005). Synthesis of Diethylamine-Functionalized Soybean Oil. J. Agric. Food Chem. 53(24), 9485-9490. DOI: 10.1021/jf050731o.
  • 17. Chlebicki, J. & Matyschok, H. (2005). Synteza i epoksydowanie estrów etylowych nienasyconych kwasów tłuszczowych oraz ich wykorzystanie w produkcji związków powierzchniowo czynnych. Przem. Chem. 84(12), 933-938.
  • 18. Ligadas, G., Ronda, J.C., Galia, M. & Cadiz, V. (2010). Plant oils as platform chemicals for polyurethane synthesis:current state-of-the-art. Biomacromolecules 11(11), 2825-2835. DOI: 10.1021/bm100839x.
  • 19. Zhang, Ch., Madbouly, S.A. & Kessler, M.R. (2015). Biobased polyurethanes prepared from different vegetable oils. Appl. Math. Interfaces 7(2), 1226-1233. DOI: 10.1021/ am5071333.
  • 20. Roth, M., Tang, Q., Malherbe, R. & Schoenenberger, C. (2001). U.S. Patent No. 6,194,490 B1. Brewster, NY (US): Vantico, Inc.
  • 21. Thames, S.F. & Yu, H. (1999). Cationic UV-cured coatings of epoxide-containing vegetable oils. Surf. Coat. Tech. 115(2), 208-214. DOI: 10.1016/S0257-8972(99)00244-3.
  • 22. Rüsch gen Klaas, M. & Warwel, S. (1999). Complete and partial epoxidation of plant oil by lipase-catalysed perhydrolysis. Ind. Crop. Prod. 9(2), 125-132. DOI: 10.1016/S0926-6690(98)00023-5.
  • 23. Mc Kenna, A.L., Fatty amides, synthesis, properties, reactions and applications. Witco Chemical Corporation, Humko Chemical. Division, Memphis, 1982, 111-194.
  • 24. Goud, V.V., Patwardhan, A.V., Dinda, S. & Pradhan, N.C. (2007). Epoxidation of karanja (Pongamia glabra) oil catalysed by acidic ion exchange resin. Eur. J. Lipid Sci. Technol. 109, 575-584. DOI: 10.1002/ejlt.200600298.
  • 25. Goud, V.V., Patwardhan, A.V., Dinda, S. & Pradhan, N.C. (2007). Kinetics of epoxidation of jatropha oil with peroxyacetic and peroxyformic acid catalysed by acidic ion exchange resin. Chem. Eng. Sci. 62(15), 4065-4076. DOI: 10.1016/j.ces.2007.04.038.
  • 26. Milchert, E. & Smagowicz, A. (2009). The Influence of Reaction Parameters on the Epoxidation of Rapeseed Oil with Peracetic Acid. J. Am. Oil Chem. Soc. 86, 1227-1233. DOI: 10.1007/s11746-009-1455-7.
  • 27. Goud, V.V., Patwardhan, A.V. & Pradhan, N.C. (2006). Studies on the epoxidation of mahua oil (Madhumica indica) by hydrogen peroxide. Biores. Technol. 97(12), 1365-1371. DOI: 10.1016/j.biortech.2005.07.004.
  • 28. Schmitz, W.R. & Wallace, J.G. (1954). Epoxidation of methyl oleate with hydrogen peroxide. J. Am. Oil Chem. Soc. 31(9), 363-365. DOI: 10.1007/BF02545510.
  • 29. Matyschok, H. & Chlebicki, J. (2001). Synthesis and epoxidation of methyl esters of unsaturated fatty acids. Pol. J. Appl. Chem. 45(1-2), 13-23.
  • 30. Milchert, E. & Kłos, M. (2013). Epoksydacja zużytych olejów roślinnych kwasem nadoctowym. Przem. Chem. 92, 670-674.
  • 31. Gurbanov, M.S. & Mamedov, M.A. (2009). Epoxidation of flax oil with hydrogen peroxide in a conjugate system in the presence of acetic acid and chlorinated cation exchanger KU-2×8 as catalyst. Russ. J. Appl. Chem. 82(8), 1483-1487.
  • 32. Milchert, E., Smagowicz, A. & Lewandowski, G. (2010). Optimization of the Epoxidation of Rapeseed Oil with Peracetic Acid. Org. Proc. Res. Dev. 14, 1094-1101. DOI: 10.1021/ op900240p.
  • 33. Zheng, J.L., Wärnå, J., Salmi, T., Burel, F., Taouk, B. & Leveneur, S. (2016). Kinetic modeling strategy for an exothermic multiphase reactor system: Application to vegetable oils epoxidation using Prileschajew method. AIChE Journal 62(3), 726-741. DOI: 10.1002/aic.15037.
  • 34. Leveneur, S., Zheng, J., Taouk, B., Burel, F., Wärnå, J. & Salmi, T. (2014). Interaction of thermal and kinetic parameters for a liquid-liquid reaction system: Application to vegetable oils epoxidation by peroxycarboxylic acid. J. Taiwan Inst. Chem. E. 45, 1449-1458. DOI: 10.1016/j.jtice.2014.01.015.
  • 35. Goud, V.V., Patwardhan, A.V. & Pradhan, N.C. (2006). Epoxidation of Karanja (Pongamia glabra) Oil by H2O2. J. Am. Oil Chem. Soc. 83(7), 635-640. DOI: 10.1007/s11746-006-1250-7.
  • 36. Goud, V.V., Patwardhan, A.V. & Pradhan, N.C. (2007). Kinetics of in situ Epoxidation of Natural Unsaturated Triglycerides Catalyzed by Acidic Ion Exchange Resin. Ind. Eng. Chem. Res. 46(10), 3078-3085. DOI: 10.1021/ie060146s.
  • 37. Campanella, A. & Baltanás, M.A. (2006). Degradation of the oxirane ring of epoxidized vegetable oils in liquid-liquid heterogeneous reaction systems. Chem. Eng. J. 118(3), 141-152. DOI: 10.1016/j.cej.2006.01.010.
  • 38. Petrović, Z.S., Zlatanić, A., Lava, C.C. & Sinadinović- Fišer, S. (2002). Epoxidation of soybean oil in toluene with peroxoacetic and peroxoformic acids - kinetics and side reactions. Eur. J. Lipid Sci. Technol. 104(5), 293-299. DOI: 10.1002/1438-9312(200205)104:5<293::AID-EJLT293>3.0.CO;2-W.
  • 39. Rangarajan, B., Havey, A., Grulke, E.A. & Culnan, P.D. (1995). Kinetic parameters of a two-phase model forin situ epoxidation of soybean oil. J. Am. Oil Chem. Soc. 72(10), 1161-1169. DOI: 10.1007/BF02540983.
  • 40. Doll, K.M., Bantchev, G.B. & Murray, R.E. Bismuth, (2013). Bismuth(III) Trifl uoromethanesulfonate Catalyzed Ring-Opening Reaction of Mono Epoxy Oleochemicals To Form Keto and Diketo Derivatives. ACS Sust. Chem. Eng. 1, 39-45. DOI: 10.1021/sc300092r.
  • 41. Carlson, K.D., Kleiman, R. & Bagby, M.O. (1994). Epoxidation of Lesquerella and Limnanthes (Meadowfoam) Oils. J. Am. Oil Chem. Soc. 71(2), 175-182. DOI: 10.1007/BF02541553.
  • 42. Sinadinović-Fišer, S., Janković, M. & Petrović, Z.S. (2001). Kinetics of in situ epoxidation of soybean oil in bulk catalyzed by ion exchange resin. J. Am. Oil Chem. Soc. 78(7), 725-731. DOI: 10.1007/s11746-001-0333-9.
  • 43. Jourdan-Laforte, E. (1980). U.S. Patent No. 4,215,058 A. Paris: L’Air Liquide, Societe Anonyme pourl’Etude et l’Exploitation des Brevets Georges Claude.
  • 44. Janković, M.R., Sinadinović-Fišer, S.V. & Govedarica, O.M. (2014). Kinetics of the Epoxidation of Castor Oil with Peracetic Acid Formed in Situ in the Presence of an Ion-Exchange Resin. Ind. Eng. Chem. Res. 53(22), 9357-9364. DOI: 10.1021/ie500876a.
  • 45. Dinda, S., Goud, V.V., Patwardhan, A.V. & Pradhan, N.C. (2011). Selective epoxidation of natural triglycerides using acidic ion exchange resin as catalyst. Asia-Pacific J. Chem. Eng. 6(6), 870-878. DOI: 10.1002/apj.466.
  • 46. Sinadinović-Fišer, S., Janković, M. & Borota, O. (2012). Epoxidation of castor oil with peracetic acid formed in situ in the presence of an ion exchange resin. Chem. Eng. Proc. 62, 106-113. DOI: 10.1016/j.cep.2012.08.005.
  • 47. Nowak, J. A., Zillner, T.A. & Mullin, L.P. (2004). U.S. Patent No. 6,734,315 B1. Chicago: The C.P. Hall Company
Uwagi
Opracowanie ze środków MNiSW w ramach umowy 812/P-DUN/2016 na działalność upowszechniającą naukę.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-d25eaa1c-d063-4363-a7ed-432bae02e9ec
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