Microwave Assisted Cationic Polymerization of Different Type Palm Oils with Boron Trifluoride Ethereal Catalyst

https://doi.org/10.22146/ijc.26680

Muhamad Farid(1*), Bambang Soegijono(2), Zainal Alim Mas’ud(3)

(1) Department of Physics, Universitas Indonesia, Kampus Baru UI, Depok 16424, Indonesia
(2) Department of Physics, Universitas Indonesia, Kampus Baru UI, Depok 16424, Indonesia
(3) Department of Chemistry, Bogor Agricultural University, Jl. Tanjung Kampus IPB Darmaga, Bogor 16680, West Java, Indonesia
(*) Corresponding Author

Abstract


Indonesia is a major producer of palm oils. However, more than 76% of the production is exported as crude palm oil (CPO) with low economic values. Chemical conversion is necessary to produce more valuable derivatives of renewable biobased material including a thermoplastic polymer. In this study, crude palm oils (CPO), refined-bleached deodorized palm oil (RBDPO) and refined bleached deodorized palm oil olein (RBDPOO) were converted under microwave-assisted cationic polymerization with the boron trifluoride ethereal catalyst. The precursors were irradiated using the commercial microwave with various reaction conditions. The raw material compositions, iodine values, and functional groups of the raw material and polymers were analyzed by gas chromatography, titrimetry, and Fourier Transform infrared spectrophotometry, respectively. The differential scanning calorimetric (DSC) was used to observe the thermal characteristics of the polymers. The iodine value of the resulting polymer products was lower than the raw materials which indicated the decrease of the C=C bonds due to the polymerization. This result is supported by the decreased intensity of alkene bands in the infrared spectra of the product. The DSC thermogram curve proved that the product is a thermoplastic polymer with a melting point ranged from 40.3 to 45.2 °C; and the freezing point of 22.5 to
28.1 °C. In conclusion, palm oil-based thermoplastic polymer was successfully synthesized and characterized, and the best result was achieved when using RBDPOO as starting material.

Keywords


palm oil; cationic polymerization; microwave; biobased materials

Full Text:

Full Text PDF


References

[1] FAO, 2016, FAOSTAT, http://faostat3.fao.org/download/Q/QC/E, accessed on May 7, 2016.

[2] BPS, 2016, Luas Areal Tanaman Perkebunan Besar Menurut Jenis Tanaman (000 Ha, 1995-2014*), https://www.bps.go.id/linkTabelStatis/view/id/1665, accessed on May 7, 2016.

[3] Sulistyanto, A.I., and Akyuwen, R., 2011, Factors affecting the performance of Indonesian’s crude palm oil export, International Conference on Economics and Finance Research, IPEDR, vol. 4, 281–289.

[4] Corma, A., Iborra, S., and Velty, A., 2007, Chemical routes for the transformation of biomass into chemicals, Chem. Rev., 107 (6), 2411–2502.

[5] Appalasami, S., and de Vries, R.J., 1990, The future of palm oil in oleochemicals, Palm Oil Dev., 14 (3), 18–29.

[6] Rupilius, W., and Ahmad, S., 2006, The changing world of oleochemicals, Palm Oil Dev., 44 (15), 21–28.

[7] Petrović, Z.S., 2010, Polymers from biological oils, Contemp. Mater., I (1), 39–50.

[8] Larock, R.C., Hanson, M., and Li, F., 2002, Lewis acid-catalyzed polymerization of biological oils and resulting polymeric materials, U.S. Patent 2002/0095007 A1, July 18, 2002.

[9] Ionescu, M., and Petrović, Z.S., 2008, Cationic polymerization of biological oils, U.S. Patent 2008/0281071 A1, November 13, 2008.

[10] Ionescu, M., and Petrović, Z.S., 2009, Cationic polymerization of biological oils with superacid catalysts, U.S. Patent 7501479 B2, March 10, 2009.

[11] Ionescu, M., and Petrović, Z.S., 2009, Cationic polymerization of biological oils, U.S. Patent 2009/0309064 A1, December 17, 2009.

[12] Ionescu, M., and Petrović, Z.S., 2011, “Polymerization of Soybean Oil with Superacids” in Soybean-Applications and Technology, Eds. Tzi, B.N., InTech, Rijeka, Croatia, 365–386.

[13] Ionescu, M., and Petrović, Z.S., 2011, Cationic polymerization of biological oils, U.S. Patent 8013088 B2, September 6, 2011.

[14] Zong, L., Zhou, S., Sgriccia, N., Hawley, M.C., and Kempel, L.C., 2003, A review of microwave-assisted polymer chemistry (MAPC), J. Microwave Power Electromagn. Energy, 38 (1), 49–74.

[15] Sinnwell, S., and Ritter, H., 2007, Recent advances in microwave-assisted polymer synthesis, Aust. J. Chem., 60 (10), 729–743.

[16] Sosnik, A., Gotelli, G., and Abraham, G.A., 2011, Microwave-assisted polymer synthesis (MAPS) as a tool in biomaterials science: How new and how powerful, Prog. Polym. Sci., 36 (8), 1050–1078.

[17] AOAC, 2012, AOAC official method 993.20, Iodine value of fats and oils wijs (cyclohexane–acetic acid solvent) method, 19th ed., Official methods of analysis of AOAC international, AOAC, Arlington, Virginia.

[18] AOAC, 2012, AOAC official method 969.33, Fatty acids in oils and fats preparation of methyl esters boron trifluoride method, 19th ed., Official methods of analysis of AOAC international, AOAC, Arlington, Virginia.

[19] AOAC, 2012, AOAC official method 963.22, Methyl esters of fatty acids in oils and fats gas chromatographic method, 19th ed., Official methods of analysis of AOAC international, AOAC, Arlington, Virginia.

[20] Shimadzu Corporation, 2002, Instruction Manual IRPrestige-21, Shimadzu Corporation, Kyoto, 78.

[21] Firestone, D., 1994, Determination of the iodine value of oils and fats: summary of collaborative study, J. AOAC Int., 77 (3), 674–676.

[22] Balai Besar Industri Agro, 2013, Laporan uji profisiensi Balai Besar Industri Agro Tahun 2013 komoditas: crude palm oil (CPO), Balai Besar Industri Agro, Bogor.

[23] Siew W.L, 2011, “Palm Oil” in Vegetable Oils in Food Technology Composition, Properties and Uses, 2nd ed., Eds., Gunstone, F.D., Blackwell Publishing Ltd., Oxford, 25–58.

[24] Komite Akreditasi Nasional, 2008, Program Uji Profisiensi KAN XI/2008: Minyak Goreng, Jakarta.

[25] Chapman, D., 1965, Infrared spectroscopy of lipids, J. Am. Oil Chem. Soc., 42 (5), 353–371.

[26] Freeman, N.K., 1968, Applications of infrared absorption spectroscopy in the analysis of lipids, J. Am. Oil Chem. Soc., 45 (11), 798–809.

[27] Guillén, M.D., and Cabo, N., 1997, Infrared spectroscopy in the study of edible oils and fats, J. Sci. Food Agric., 75 (1), 1–11.

[28] Guillén, M.D., and Cabo, N., 1997, 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 (10), 1281–1286.

[29] Farag, R.S., Hewedi, F.M., Abo-Raya, S.H., and El-baroty, G.S.A., 1991, A comparative study on the deterioration of oils by microwave and conventional heating, Grasas y Aceites, 42 (3), 187–193.

[30] Kreps, F., Vrbiková, L., Schmidt, S., Sekretár, S., and Híreš, O., 2014, Chemical changes in microwave heated vegetable oils, Eur. J. Lipid Sci. Technol., 116 (12), 1685–1693.

[31] Abbas Ali, M., Bin Mesran, M.H., Abd Latip, R., Othman, N.H., and Nik Mahmood, N.A., 2016, Effect of microwave heating with different exposure times on the degradation of corn oil, IFRJ, 23 (2), 842–848.

[32] Whiteley, J.M., Elizabeth and Turner, L.B., 1941. Treating fatty oils and the like, U. S. Patent 2260417, October 28, 1941.

[33] Cowan, J.C., Wheeler, D.H., Teeter, H.M., Paschke, R.E., Scholfield, C.R., Schwab, A.A., Jackson, J.E., Bull, W.C., Earle, F.R., Foster, R.J., Bond, W.C., Beal, R.E., Skell, P.S., Wolff, I.A., and Mehltretter, C., 1949, Polymerization of drying oils, Ind. Eng. Chem., 41 (8), 1647–1653.

[34] Croston, C.B., Tubb, I.L., Cowan, J.C., and Teeter, H.M., 1952, Polymerization of drying oils. VI. Catalytic polymerization of fatty acids and esters with boron trifluoride and hydrogen fluoride, J. Am. Oil Chem. Soc., 29 (8), 331–333.

[35] Pavia, D.L., Lampman, G.M., Kriz, G.S., and Vyvyan, J.R., 2009, Introduction to Spectroscopy, 4th ed., Brooks/Cole, Cengage Learning, Belmont, 15–104.

[36] Li, F.K., and Larock, R.C., 2002, Novel polymeric materials from biological oils, J. Polym. Environ., 10 (1-2), 59–67.

[37] Lu, Y.S., and Larock, R.C., 2009, Novel polymeric materials from vegetable oils and vinyl monomers: Preparation, properties, and applications, ChemSusChem, 2 (2), 136–147.

[38] Xia Y., and Larock, R.C., 2010, Vegetable oil-based polymeric materials: synthesis, properties, and applications, Green Chem., 12 (11), 1893–1909.

[39] Xia, Y., Quirino, R.L., and Larock, R.C., 2013, Bio-based thermosetting polymers from vegetable oils, J. Renewable Mater., 1 (1), 3–27.

[40] Llevot, A., 2017, Sustainable synthetic approaches for the preparation of plant oil‑based thermosets, J. Am. Oil Chem. Soc., 94 (2), 169–186.

[41] Kawamura, K., 1979, The DSC thermal analysis of crystallization behavior in palm oil, J. Am. Oil Chem. Soc., 56 (8), 753–758.

[42] Kawamura, K., 1980, The DSC thermal analysis of crystallization behavior in palm oil, II, J. Am. Oil Chem. Soc., 57 (1), 48–52.

[43] Man, Y.B.C., Haryati, T., Ghazali, H.M., and Asbi, B.A., 1999, Composition and thermal profile of crude palm oil and its products, J. Am. Oil Chem. Soc., 76 (2), 237–242.

[44] Zhang, X., Li, L., Xie, H., Liang, Z., Su, J., Liu, G., and Li, B., 2013, Comparative analysis of thermal behavior, isothermal crystallization kinetics and polymorphism of palm oil fractions, Molecules, 18 (1), 1036–1052



DOI: https://doi.org/10.22146/ijc.26680

Article Metrics

Abstract views : 708 | views : 753


Copyright (c) 2018 Indonesian Journal of Chemistry

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

 


Indonesian Journal of Chemisty (ISSN 1411-9420 / 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web
Analytics View The Statistics of Indones. J. Chem.