Directed Study of Abietic Acid Reaction in Pine Rosin under Non-Precious-Metal Catalyst
Abstract
Pine rosin of Pinus merkusii Jung at de Vriese is produced industrially from a distillation process of pine sap. The high total Indonesian production leads the primary derivatization strategy into several derivates to fulfill the market demand. Abietic acid (AA) is a major compound in pine rosin, used as the object of observation in this study. The general methodology for transformation reported involves using palladium (Pd) and platinum (Pt)-based catalysts. Both are precious metal catalysts to proceed with oxidative dehydrogenative-aromatization of the rosin. The synthesized product provides dehydroabietic acid (DHA) derivatives in high yield. This paper reports that non-precious metal-based catalysts such as iron (Fe), zinc (Zn), or copper (Cu) with iodine (I2) were applied to deliver the reaction by steam cracking without nitrogen (N2) and oxygen (O2) for economical, efficient, and greenway’s catalyst. It was found that a similar product was isolated, including several by-products. Under high temperatures with a various metal transitions and halogen by FeCl3-I2 and Cu(NO3)2.3H2O and ZnCl2 catalyst, four compounds were identified employing spectroscopic methods in the reaction product: 7-hydroxy-dehydroabietic acid (5), 1,7-dihydroxy-dehydroabietic acid (6), 7-isopropyl-1-methylphenanthren-9-ol (7) and polymer (8). This modified pine rosin was mainly used as an emulsifier for the synthetic rubber industry, varnish, ink, paper sizing, etc. The products are determined based on LC-MS/MS, UV-Vis, and ATR-FTIR spectroscopy.
Keywords
References
Abdel-raouf, M. E., and M.Abdul, M. (2018). Rosin : Chemistry, Derivatives, and Applications : A Review. Bio-Accent, 4(039), 1–16.
Adilbekov, D. (2016). ANALYTICAL ANALYSIS OF ROMAN AMPHORAE. October.
Alvarez, M. et al. (2007). Regioselective Routes Towards 14-Hydroxyabietane Diterpenes. A Formal Synthesis of Immunosuppressant (-)-Triptolide from (+)-Abietic Acid. Tetrahedron, 63(45), 11204–11212. https://doi.org/10.1016/j.tet.2007.07.088
Berg, K.J., Boon J.J. (2000). Mass Spectrometric Methodology for the Analysis of Highly Oxidized Diterpenoid Acids in Old Master Paintings. Journal of Mass Spectrometry, 35(512–533).
Brocas, A., Llevlot, A., and Mantzaridis, C. (2014). Epoxidized Rosin Acids As Co-Precursors For Epoxy Resins. Design Monomers and Polymers, 17(4), 301–310. https://doi.org/10.1080/15685551.2013.840504
Corryanti., and Rahmawati, R. (2015). Terobosan Memperbanyak Pinus (Pinus Merkusii). PUSLITBANG PERUM PERHUTANI.
Fan. Huahua. (2020). Mechanistic Understanding of Ethane Dehydrogenation and Aromatization over Zn/ZSM-5: Effects of Zn Midification and CO2 Co-Reactant. https://doi.org/10.1039/D0CY01566K
Frances, M., Gardere, Y., and Duret, E. (2020). Effect of Heat Treatment on Pinus Pinaster Rosin: A study of Physico Chemical Changes and Influence on the Quality of Rosin Linseed Oil Varnish. Industrial Crops and Products, 155(July). https://doi.org/10.1016/j.indcrop.2020.112789
Gonçalves, M. D., and Al., E. (2018). Dehydroabietic Acid Isolated from Pinus Elliottii Exerts in Vitro Antileishmanial Action by Pro-Oxidant Effect, Inducing ROS Production in Promastigote and Downregulating Nrf2/Ferritin Expression in Amastigote Forms of Leishmania Amazonensis. Fitoterapia, 128, 224–232. https://doi.org/10.1016/J.FITOTE.2018.05.027
Gu, Y., and Al., E. (2020). Effects of Pretreated Carbon Supports in Pd/C Catalysts on Rosin Disproportionation Catalytic Performance. Chemical Engineering Science, 216(February), 115588. https://doi.org/10.1016/j.ces.2020.115588
Hongo, T. (2008). Adsorption Ability for Several Harmful Anions and Thermal Behaviour of Zn-Fe Layered Double Hydroxide. 116, 1350, 192–197.
Kugler, S., Ossowicz, P., Kornelia, M., and Wierzbicka, E. (2019). Advances in Rosin-Based Chemicals: The Latest Recipes, Applications and Future Trends. Molecules, 24(9), 1–51. https://doi.org/10.3390/molecules24091651
Kuspradini, H., Rosamah, E., Sukaton, E., Arung, E. T., and Kusuma, I. W. (2016). Pengenalan Jenis Getah : Gum Lateks Resin.
Lemonidou, H. E. (2010). AA. Ni–Nb–O Mixed Oxides as Highly Active and Selective Catalysts for Ethane Production Via Ethane Oxidative Dehydrogenation. Journal Catalyst, 270, 67–75.
Li, J. L. X. L. W. (2014). Kinetics of Gum Rosin Oxidation Under 365 nm Ultraviolet Irradiation. Monatsh Chem, 209–212. https://doi.org/10.1007/s00706-013-1014-7
Li, Y. et al. (2019). Iodine-Promoted Intermolecular Dehydrogenation Diamination : Synthesis of Unsymmetrical α, β-diamido Ketones. An Asian Journal. https://doi.org/10.1002/asia.201900170
Li, Y., Xu, X., Niu, M., and Chen, J. (2019). Thermal Stability of Abietic Acid and Its Oxidation Products. Energy and Fuels, 33(11), 11200–11209. https://doi.org/10.1021/acs.energyfuels.9b02855
Martín-ramos, P. et al. (2018). Potential of ATR-FTIR Spectroscopy for the Classification of Natural Resins. BEMS Reports, 4(1), 3–6.
Meesupthong, R., Yingkamhaeng, N., Nimchua, T., Pinmanee, P., Mussatto, S. I., Li, B., and Sukyai, P. (2020). Xylanase pretreatment of energy cane enables facile cellulose nanocrystal isolation. Cellulose. https://doi.org/10.1007/s10570-020-03559-y
Meesupthong, R., Yinkamhaenf, N., and Al., E. (2018). Aromatization of Hydrocarbons by Oxidative Dehydrogenation Catalyzed by Nickel Porphyrin with Molecular Oxygen. Catalysis Communications, 117, 85–89. https://doi.org/https://doi.org/10.1016/j.catcom.2018.09.003
Mitani, K. et al. (2007). Analysis of Abietic Acid and Dehydroabietic Acid in Food Samples by In-Tube Solid-Phase Microextraction Coupled with Liquid Chromatography-Mass Spectrometry. Journal of Chromatography A, 1146(1), 61–66. https://doi.org/10.1016/j.chroma.2007.01.118
Mostafalu, R., Heydari, A., Banaci, A., and Ghorbani, F. (2017). The Use of Palladium Nanoparticles Supported on Active Carbon for Synthesis of Disproportionate Rosin ( DPR ). Journal of Nanostructure in Chemistry, 7(1), 61–66. https://doi.org/10.1007/s40097-017-0220-y
Pagacz, J. et al. (2019). Preliminary Thermal Characterization of Natural Resins from Different Botanical Sources and Geological Environments. Journal of Thermal Analysis and Calorimetry, 0. https://doi.org/10.1007/s10973-019-08157-0
Pasternak, I.S., Vadekar, M. (1970). Sulphur / Halogen Promoted Oxidative Dehydrogenation of Hydrocarbons. The Canadian Journal of Chemical Engineering, 48.
Primaningtyas, A., and Widyorini, R. (2020). Evaluasi Proses Produksi Industri Gondorukem dari Tinjauan Aliran Massa dan Energi (Studi kasus PGT Sapuran) [Evaluation of the Gum Rosin Industrial Production Process Based on Mass and Energy Balances (PGT Sapuran case study). Jurnal Riset Industri Hasil Hutan, 12(1), 39. https://doi.org/10.24111/jrihh.v12i1.5996
Ramos, Martin. Fernandez, P. (2018). Potential of ATR-FTIR spectroscopy for the classification of Natural Resins. BEMS Rep., 4(1), 3–6.
Setianingsih, T. (2017). Metal Precious. International Journal of ChemTech Research, 10(6), 10–19.
Skoufa Z, et al. (2015). On Ethane ODH Mechanism and Nature of Active Sites Over NiO-Based Catalysts Via Isotopic Labeling and Methanol Sorption Studies. J. Catalyst, 322, 118–129.
Smeds, A. I., Eklund, P. C., and M. Willfor, S. (2017). Characterization of High-Molar-Mass Fractions in a Scots Pine (Pinus Sylvestris L.) Knotwood Ethanol Extract. DE GRUYER.
Upham, D. C., Gordon, M. J., Metin, H., and McFariand, E. W. (2016). Halogen-Mediated Oxidative Dehydrogenation of Propane Using Iodine or Molten Lithium Iodide. Catalysis Letters. https://doi.org/10.1007/s10562-016-1701-1
Y., T. (2014). Analysis of The Components of Hard Resin in Hops (Humulus Lupulus L.) and Structural Elucidation of Their Transformation Products Formed During the Brewing process. Journal of Agricultural and Food Chemistry, 62(47), 11602–11612.
Yusubov, M. S., and Zhdankin, V. V. (2015). Iodine Catalysis : A green Alternative to Transition Metals in Organic Chemistry and Technology. Resource-Efficient Technologies, 782, 1–19. https://doi.org/10.1016/j.reffit.2015.06.001
DOI: 10.15408/jkv.v8i1.22802
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