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

Milchert, Eugeniusz; Malarczyk-Matusiak, Kornelia; Musik, Marlena

doi:10.1515/pjct-2016-0059

Abstract

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.

References

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.10.1007/s11746-008-1277-z
Search in Google Scholar Back to article
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.2006.07.001.10.1016/j.progpolymsci.2006.07.001
Search in Google Scholar Back to article
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.
Search in Google Scholar Back to article
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, 3737-3744.10.1016/j.biortech.2007.07.015
Search in Google Scholar Back to article
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), 21481-21493.10.3390/molecules201219778
Search in Google Scholar Back to article
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.2005.02.011.10.1016/j.jcat.2005.02.011
Search in Google Scholar Back to article
7. Benaniba, M.T., Belhaneche-Bensemra, N. & Gelbard, G. (2003). Stabilization of PVC by epoxidized sunfl ower oil in the presence of zinc and calcium stearates. Polym. Degrad. Stabil. 82(2), 245-249. DOI: 10.1016/S0141-3910(03)00178-2.10.1016/S0141-3910(03)00178-2
Search in Google Scholar Back to article
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.
Search in Google Scholar Back to article
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/s00253-006-0335-4.10.1007/s00253-006-0335-416604360
Search in Google Scholar Back to article
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.10.1007/s11746-005-1097-y
Search in Google Scholar Back to article
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, 1678-1681.10.1007/s11167-005-0585-4
Search in Google Scholar Back to article
12. Carlson, K.D. & Chang, S.P. (1985). Chemical epoxidation of a natural unsaturated epoxy seed oil fromVernonia galamensis and a look at epoxy oil markets. J. Am. Oil Chem. Soc. 62(5), 934-939. DOI: 10.1007/BF02541763.10.1007/BF02541763
Search in Google Scholar Back to article
13. Hang, X. & Yang, H. (1999). Model for Cascade Continuous Epoxidation Process. J. Am. Oil Chem. Soc. 76, 89-92. DOI: 10.1007/s11746-999-0052-0.10.1007/s11746-999-0052-0
Search in Google Scholar Back to article
14. Lathi, P.S. & Mattiasson, B. (2007). Green approach for the preparation of biodegradable lubricant basestock from epoxidized vegetable oil. Appl. Catal. Envrion. 69, 207-212.10.1016/j.apcatb.2006.06.016
Search in Google Scholar Back to article
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-8-16.10.1186/1752-153X-8-16
Search in Google Scholar Back to article
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.10.1021/jf050731o
Search in Google Scholar Back to article
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.
Search in Google Scholar Back to article
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.10.1021/bm100839x
Search in Google Scholar Back to article
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/ am5071333.10.1021/am5071333
Search in Google Scholar Back to article
20. Roth, M., Tang, Q., Malherbe, R. & Schoenenberger, C. (2001). U.S. Patent No. 6,194,490 B1. Brewster, NY (US): Vantico, Inc.
Search in Google Scholar Back to article
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)00244-3.10.1016/S0257-8972(99)00244-3
Search in Google Scholar Back to article
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)00023-5.10.1016/S0926-6690(98)00023-5
Search in Google Scholar Back to article
23. Mc Kenna, A.L., Fatty amides, synthesis, properties, reactions and applications. Witco Chemical Corporation, Humko Chemical. Division, Memphis, 1982, 111-194.
Search in Google Scholar Back to article
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.200600298.10.1002/ejlt.200600298
Search in Google Scholar Back to article
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.2007.04.038.10.1016/j.ces.2007.04.038
Search in Google Scholar Back to article
26. Milchert, E. & Smagowicz, A. (2009). The Infl uence of Reaction Parameters on the Epoxidation of Rapeseed Oil with Peracetic Acid. J. Am. Oil Chem. Soc. 86, 1227-1233. DOI: 10.1007/s11746-009-1455-7.10.1007/s11746-009-1455-7
Search in Google Scholar Back to article
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.2005.07.004.10.1016/j.biortech.2005.07.00416122922
Search in Google Scholar Back to article
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/BF02545510.10.1007/BF02545510
Search in Google Scholar Back to article
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.
Search in Google Scholar Back to article
30. Milchert, E. & Kłos, M. (2013). Epoksydacja zużytych olejów roślinnych kwasem nadoctowym. Przem. Chem. 92, 670-674.
Search in Google Scholar Back to article
31. Gurbanov, M.S. & Mamedov, M.A. (2009). Epoxidation of fl ax 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), 1483-1487.10.1134/S1070427209080308
Search in Google Scholar Back to article
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.10.1021/op900240p
Search in Google Scholar Back to article
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.15037.10.1002/aic.15037
Search in Google Scholar Back to article
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.2014.01.015.10.1016/j.jtice.2014.01.015
Search in Google Scholar Back to article
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/s11746-006-1250-7.10.1007/s11746-006-1250-7
Search in Google Scholar Back to article
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.10.1021/ie060146s
Search in Google Scholar Back to article
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.2006.01.010.10.1016/j.cej.2006.01.010
Search in Google Scholar Back to article
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.10.1002/1438-9312(200205)104:5<;293::AID-EJLT293>3.0.CO;2-W
Search in Google Scholar Back to article
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/BF02540983.10.1007/BF02540983
Search in Google Scholar Back to article
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.10.1021/sc300092r
Search in Google Scholar Back to article
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/BF02541553.10.1007/BF02541553
Search in Google Scholar Back to article
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/s11746-001-0333-9.10.1007/s11746-001-0333-9
Search in Google Scholar Back to article
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.
Search in Google Scholar Back to article
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.10.1021/ie500876a
Search in Google Scholar Back to article
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.466.10.1002/apj.466
Search in Google Scholar Back to article
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.2012.08.005.10.1016/j.cep.2012.08.005
Search in Google Scholar Back to article
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
Search in Google Scholar Back to article

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

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