Powrót do 2/20152/2015 pp. 9-15
Epoksydacja limonenu na wybranych katalizatorach tytanowo-silikalitowych
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The studies on limonene epoxidation over the titanium silicate catalysts such as: TS-1, Ti-MWW, Ti-MCM-41 and Ti-SBA-15 with methanol or acetonitrile as solvents and with 30 wt% hydrogen peroxide as an oxidant were carried out. Limonene epoxidation was performed in the water bath, under reflux, at the temperature range of 70-100oC and during 60-180 minutes. After the appropriate reaction time a sample was taken from the reaction mixture and it was analyzed by the GC method. The best from the studied catalysts was TS-1. During the epoxidation with TS-1 catalyst, only 1,2-epoxylimonene was formed, without by-product, such as 1,2-epoxylimonene diol. During the epoxidations over other titanium silicate catalysts 1,2-epoxylimonene and its diol or only 1,2-epoxylimonene itself were formed. The aim of these studies was to determine to which compounds may limonene react at the reaction conditions and in the presence of titanium-silicate catalyst - qualitative research.
Słowa kluczowelimonene epoxidation, 1,2-epoxylimonene, hydrogen peroxide
Literatura1. Trytek, M., Paduch, R., Fiedurek, J., Kandefer-Szerszeń, M., Monoterpeny – stare związki, nowe zastosowania i biotechnologiczne metody ich otrzymywania, Biotechnologia, 2007, 1(76), s. 135-155.
2. Kasprzykowska, R., Kołodziejczyk, A.S., Stachowiak, K., Jankowska, E., Preparatyka i analiza związków naturalnych, Gdańsk, 2014, Wydawnictwo Uniwersytetu Gdańskiego,.
3. Szczepanik, A., Sobkowiak, A., Utlenianie limonenu tlenem cząsteczkowym i nadtlenkiem wodoru, Wiadomości Chemiczne, 2009, 63(7-8), s. 601-634.
4. Pakdel, H., Pantea, D.M., Roy, C., Production of dl-limonene by vacuum pyrolysis of used tires, J. Anal. Appl. Pyrolysis, 2001, 57, pp. 91-107.
5. Matura, M., Sköld, M., Börje, A., Andersen, K. E., Bruze, M., Frosch, P., Goossens, A., Johansen, J. D., Svedman, C, White, I. R., Karlberg, A.T., Selected oxidized fragrance terpenes are common contact allergens, Contact Dermatitis, 2005, 52(6), pp. 320-328.
6. United States Environmental Protection Agency, R.E.D. Facts, Limonene, EPA-738-F-94-030 September 1994.
7. Cagnoli, M.V., Casucelli, S.G., Alvarez, A.M., Benogoa, J.F., Gallegos, N.G., Samaniego, N.M., Crivello, M.E., Ghione, G.E., Perez, C.F., Herrero, E.R., Marchetti, S.G., “Clean” limonene epoxidation using Ti-MCM-41 catalyst, Appl. Catal. A, 2005, 287, pp. 227-235.
8. Coates, G., Byrne, C., Allen, S., Lobkovsky, E., Alternating Copolymerization of Limonene Oxide and Carbon Dioxide, J. A. Chem. Soc., 2004, 126, pp. 11404-11405.
9. Corma, A., Iborra, S., Vielty, A., Chemical routes for the transformation of biomass into chemicals, Chem. Rev., 2007, 107, pp. 2411-2502.
10. Thomas, A.F., Bessiere, Y., Limonene, Natural Product Reports, 1989, I. 3, pp. 291-309.
11. Oliviera, P., Rojas-Carvantes, M.L., Ramoms, A.M., Fonesca, I.M., Botelho de Rego, A.M.,
Vital, J., Limonene oxidation over V2O5/TiO2 catalysts, Catal. Today, 2006, 118, pp. 307-314.
12. Pena, A., Viga, S., Sapelli, M., Martinez, N., Marquez, V., Dellacassa, E., Bussi, J., Limonene oxidation by molecular oxygen under solvent-free conditions: The influence of peroxides and
catalysts on the reaction rate, React. Kinet. Mech. Catal., 2012, 107, pp. 263-275.
13. Strassberg, Z., Ramos-Fernandez, E.V., Boonstra, A., Jorna, R., Tanase, S., Rotjenberg, G., Synthesis, characterization and testing of a new V2O5/Al2O3-MgO catalyst for butane dehydrogenation and limonene oxidation, Dalton Trans., 2013, 42, pp. 5546-5553.