Nopol synthesis from β-pinene and turpentine oil over Sn-MCM-41
DOI:
https://doi.org/10.17533/udea.redin.343244Keywords:
turpentine oil, β-pinene, nopol, Prins reaction, Lewis acid, Sn, MCM-41Abstract
Nopol was obtained by the Prins condensation of β-pinene and paraformaldehyde over Sn-MCM-41. The catalyst was synthesized by chemical vapor deposition using a Sn salt over MCM-41. Reactions were carried out using either high purity β-pinene or turpentine oil as a starting material. The effect of catalyst Sn loading, temperature, type of solvent, catalyst amount, and reaction time on nopol selectivity was studied. Catalyst samples were characterized by XRD, IR, UV-VIS, elemental analysis and BET surface area. Low Sn loaded Sn-MCM-41 yields near 100% nopol with high purity β-pinene; whereas using turpentine as β-pinene source, nopol selectivities up to 93% were attained for equimolar ratios of reactants.
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Universidad de Concepción Chile. Trementina. http:// www.udec.cl/sqrt/fich/TREMENT.htm. Consultado el 14 de noviembre de 2003.
S. R. J. Robbins y W. S. A. Matthews. “Los productos menores del bosque. Su valor global es muy importante”. Décima conferencia mundial de la mancomunidad. Oxford, septiembre de 1974. FAO 2003. http://www.fao.org/docrep/f1360S/f1360SO2.htm. Consultado el 10 de julio de 2004.
G. Sun. “Turpentine (more than paint thinner!), Applications Chemist”. Separations times 12, 2 (1998). Agilent Technologies, 2000-2003. http://www.chem.agilent.com/. Consultado el 14 de noviembre de 2003.
R. E. Kirk y D. F. Othmer. Encyclopedia of chemical technology. John Wiley & sons. 2.a ed. 1963. Vol. 19. p. 803.
J. Wiley. “Terpene Resins”. Encyclopedia of Polymer science and technology plastics resins rubbers fibers. 1.a ed. Vol. 13. 1964.
J. P. Bain. “Nopol. I. The reaction of β-pinene with formaldehyde”. En: J. Am. Chem. Soc. Vol. 68. 1946. pp. 638-641. DOI: https://doi.org/10.1021/ja01208a032
E. Arundale, L. A. Mikeska. “The olefin-aldehyde condensation. The Prins Reaction”. Chem. Rev. Vol. 52. N.o 1. 1953. pp. 505-555. DOI: https://doi.org/10.1021/cr60160a004
K. Bauer, D. Garbe, H. Surburg. “Common Fragrance and Flavor Materials. Preparation, Properties and Uses”. VCH Verlagsgesellschaft. 1990. p. 59.
R. S. Downing, H. Van Bekkum, R. A. Sheldon. “Zeolites and related materials for the solid-acid catalyzed production of fine chemicals”. En: Cattech Vol. 2. 1997. pp. 95-109.
A. Corma, E. García. “Lewis acids: from conventional homogeneous to green homogeneous and heterogeneous catalysis”. En: Chem. Rev. Vol. 103. 2003. pp. 4307-4366. DOI: https://doi.org/10.1021/cr030680z
A. L. Villa de P.; E. Alarcón; C. Montes de C. “Synthesis of Nopol over MCM-41 catalysts”. En: Chem. Commun. 2002. pp. 2654-2655. DOI: https://doi.org/10.1039/B206239A
U. R. Pillai, E. Sahle Demessie. “Mesoporous iron phosphate as an active, selective and recyclable catalyst for the synthesis of nopol by Prins condensation”. En: Chem. Commun. 2004. pp. 826-827. DOI: https://doi.org/10.1039/b313747c
M. Grün, K. Unger, A. Matsumoto, K. Tsutsumi. “Novel pathways for the preparation of mesoporous MCM-41 materials: control of porosity and morphology”. En: Microporous Mater. Vol. 27. 1999. pp. 207-216. DOI: https://doi.org/10.1016/S1387-1811(98)00255-8
K. Chaudhari, T. K. Das, P. R. Rajmohanan, K. Lazar, S. Sivasanker, A. J. Chandwadkar. “Synthesis, characterization and catalytic properties of mesoporous Tin-containing analogs of MCM-41”. En: J. Catal. Vol. 183. 1999. pp. 281-291. DOI: https://doi.org/10.1006/jcat.1999.2394
A. Severino, J. Vital, L. S. Lobo, L. S. “Isomerization of α-pinene over TiO2: kinetics and catalyst optimization”. En: M. Guisnet et al. Heterogeneous Catalysis and Fine Chemicals III. Elsevier Science Publishers. 1993. pp. 685-693. DOI: https://doi.org/10.1016/S0167-2991(08)63383-2
A. Severino, A. Esculcas, J. Rocha, J. Vital, L. S. Lobo. “Effect of extra-lattice aluminium species on the activity, selectivity and stability of acid zeolites in the liquid phase isomerisation of α-pinene.” En: Applied Catalysis A: General. Vol. 142. 1996. pp. 255-278. DOI: https://doi.org/10.1016/0926-860X(96)00091-9
J. C. van der Waal, H. Van Bekkum, J. M. Vita. “The hydration and isomerization of α-pinene over zeolite beta. A new coupling reaction between α-pinene and ketones”. En: Journal of Molecular Catalysis A: Chemical. Vol. 105. 1996. 185-192. DOI: https://doi.org/10.1016/1381-1169(95)00244-8
D. V. Banthorpe, D. Whittaker. “Rearrangements of pinane derivatives”. En: Q. Rev. Chem. Soc. Vol. 20. 1966. pp. 373-387. DOI: https://doi.org/10.1039/qr9662000373
G. J. Gainsford, C. Hosie, R. J. Weston, N. B. Milestone. “Reactions of pinenes over zeolites”. En: Proceedings of 15th Meeting of North American Catalysis Society. Illinois. May 18-22. 1997. p. 132.
V. P. Wystrach, L. H. Barnum, M. Garber. “Liquid phase catalytic isomerization of α-pinene”. En: J. Am. Chem. Soc. Vol. 79. 1957. pp. 5786-5790. DOI: https://doi.org/10.1021/ja01578a053
G. L. Kaiser. “Isomerization of alpha-pinene to betapinene with neutralized alumina-supported catalyst”. USA Patent N.o 4000208. December 28. 1976.
A. Corma, M. T. Navarro, M. Renz. “Lewis acidic Sn (IV) centers-grafted onto MCM-41- as catalytic sites for the Baeyer-Villiger oxidation with hydrogen peroxide”. En: Journal of Catalysis. Vol. 219. 2003. pp. 242-246. DOI: https://doi.org/10.1016/S0021-9517(03)00190-8
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