The oxidation of limonene at raised pressure and over the various titanium-silicate catalysts

• Autorzy: Wróblewska A. , Makuch E. , Miądlicki P.

Identyfikatory

DOI

10.1515/pjct-2015-0072

• Języki publikacji: EN

Abstrakty

EN

This work presents the studies on the oxidation of limonene with hydrogen peroxide and tert-butyl hydroperoxide (TBHP) in the presence of : TS-2, Ti-Beta, Ti-MCM-41 and Ti-MWW catalysts, at the autogenic pressure and atmospheric pressure. The examination were performed at the following conditions: the temperature of 140°C (studies in the autoclave) and 80°C (studies in glass reactor), the molar ratio of limonene/oxidant (H2O2 or WNTB) = 1:1, the methanol concentration 80 wt%, the catalyst content 3 wt%, the reaction time 3 h and the intensity of stirring 500 rpm. The analysis of the results showed that in process not only 1,2-epoxylimonene was formed but also: 1,2-epoxylimonene diol, carveol, carvone and perillyl alcohol but for 1,2-epoxylimonene obtaining the better method was the method at the autogenic pressure and in the presence of TBHP.

Słowa kluczowe

EN

limonene oxidation; hydrogen peroxide; TBHP

• Wydawca: West Pomeranian University of Technology. Publishing House
• Czasopismo: Polish Journal of Chemical Technology
• Rocznik: 2015
• Tom: Vol. 17, nr 4
• Strony: 82--87
• Opis fizyczny: Bibliogr. 29 poz., rys., tab.

Twórcy

autor

Wróblewska A.

• West Pomeranian University of Technology, Szczecin, Institute of Organic Chemical Technology, ul. Pulaskiego 10, 70-322 Szczecin, Poland

autor

Makuch E.

• West Pomeranian University of Technology, Szczecin, Institute of Organic Chemical Technology, ul. Pulaskiego 10, 70-322 Szczecin, Poland

autor

Miądlicki P.

• West Pomeranian University of Technology, Szczecin, Institute of Organic Chemical Technology, ul. Pulaskiego 10, 70-322 Szczecin, Poland

Bibliografia

• 1. Santa, A.M., Vergara, J.C., Palacio, L.A. & Echavarria, A. (2008). Limonene epoxidation by molecular sieves zinco-phosphates and zincochromates. Catal. Today 2008, 133–135, 80–86. DOI: 10.1016/j.cattod.2007.12.025.
• 2. Cagnoli, M.V., Casuscelli, S.G., Alvarez, A.M., Bengoa, J.F., Gallegos, N.G., Samaniego, N.M., Crivello, M.E., Ghione, G.E., Pérez, C.F., Herrero, E.R., Marchettia, S.G. (2005). “Clean” limonene epoxidation using Ti-MCM-41 catalyst. Appl. Catal. A: General 287(2), 227–235. DOI: 10.1016/j.apcata.2005.04.001.
• 3. Pena, A., Veiga, S., Sapelli, M., Martinez, N., Marquez, V., Dellacassa, E. & Bussi, J. (2012). Limonene oxidation by molecular oxygen under solvent-free conditions: The influence of peroxides and catalysts on the reaction rate. React. Kinet. Mech. Catal. 107, 263–275. DOI: 10.1007/s11144-012-0485-6.
• 4. Monteiro, J.L.F. & Veloso, C.O. (2004). Catalytic conversion of terpenes into fine chemicals. Top. Catal. 27, 169–180. DOI: 1022-5528/04/0200–0169/0.
• 5. Rodrigues, S.N., Fernandes, I., Martins, I.M., Mata, V.G., Barreiro, F. & Rodrigues, A.E. (2008). Microencapsulation of limonene for textile application. Ind. Eng. Chem. Res. 47 (12), 4142–4147. DOI: 10.1021/ie800090c.
• 6. Corma, A., Iborra, S. & Velty, A. (2007). Chemical routes for the transformation of biomass into chemicals. Chem. Rev. 107, 2411–2512. DOI: 10.1021/cr050989d.
• 7. Arizaga, B., Leon, A., Burguen. N., Lopez, A., Paz, D., Martınez, N., Lorenzo, D., Dellacassa, E. & Bussi, J. (2007). A clean process for the production of oxygenated limonene derivatives starting from orange oil. J. Chem. Technol. Biotechnol. 82, 532–538. DOI: 10.1002/jctb.1690.
• 8. Nguyen, T.T.T., Nguyen Chau, D.K., Duus, F. & Le, T.N. (2013). Green synthesis of carvenone by montmorillonite-catalyzed isomerization of 1,2-limonene oxide. J. Org. Chem. 3, 206–209. DOI: 10.4236/ijoc.2013.33027.
• 9. Byrne, C.M., Allen, S.D., Lobkovsky, E.B. & Coates, G.W. (2004). Alternating copolymerization of limonene oxide and carbon dioxide. J. Am. Chem. Soc. 126, 11404–11405. DOI: 10.1021/ja0472580.
• 10. Almeida, A.A.A., Carvalho, R.B.F., Silva, O.A., Sousa, D.P. & Freitas, R.M. (2014). Potential antioxidant and anxiolytic effects of (+)-limonene epoxide in mice after marble-burying test. Pharmacol. Biochem. Behav. 118, 69–78. DOI: 10.1016/j.pbb.2014.01.006.
• 11. Almeida, A.A.A., Costa, J.P., Carvalho, R.B.F., Sousa, D.P. & Freitas, R.M. (2012). Evaluation of acute toxicity of a natural compound (+)-limonene epoxide and its anxiolytic-like action. Brain Res. 1448, 56–62. DOI: 10.1016/j.brainres.2012.01.070.
• 12. Gupta, A. & Myrdal, P.B. (2004). Development of a perillyl alcohol topical cream formulation. Int. J. Pharm. 26, 373–383. DOI: 10.1016/j.ijpharm.2003.09.026.
• 13. Gupta, A., Stratton, S.P. & Myrdal, P.B. (2005). An HPLC method for quantitation of perillyl alcohol in a topical pharmaceutical cream formulation. J. Pharm. Biomed. Anal. 37, 447–452. DOI: 10.1016/j.jpba.2004.02.039.
• 14. Bonon, A.J., Mandelli, D., Kholdeeva, O.A., Barmatova, M.V., Kozlov, Y.N. & Shulpin, G.B. (2009). Oxidation of alkene and olefins with hydrogen peroxide in acetonitrile solution catalyzed by a mesoporous titanium-silicate Ti-MMM-2. Appl. Catal. A General 365, 96–104. DOI: 10.1016/j.apcata.2009.05.060.
• 15. Berlini, Ch., Guidotti, M., Moretti, G., Psaro, R. & Ravasio, N. (2000). Catalytic epoxidation of unsaturated alcohols on Ti-MCM-41. Catal. Today 60, 209–225. DOI: 10.1016/S0920-5861(00)00338-2.
• 16. Cagnoli, M.V., Casuscelli, S.G., Alvarez, A.M., Bengoa, J.F., Gallegos, N.G., Crivello, M.E., Herrero, E.R. & Marchetti, S.G. (2005). Ti-MCM_41 silylation: development of a simple methodology for its estimation. Silylation effect on the activity and selectivity in the limonene oxidation with H2O2. Catal. Today 107–108, 397–403. DOI: 10.1016/j.cattod.2005.07.034.
• 17. Marino, D., Gallegos, N., Bengoa, J.F., Alvarez, A.M., Cagnoli, M.V., Casuscelli, S.G., Herrero, E.R. & Marchetti, S.G. (2008). Ti-MCM-41 catalysts prepared by post-synthesis methods. Limonene epoxidation with H2O2. Catal. Today 133–135, 632–638. DOI: 10.1016/j.cattod.2007.12.111.
• 18. Chiker, F., Launay, F., Nogier, J.P. & Bonardet, J.L. (2003). Green epoxidation on Ti-mesoporous catalysts. Environ. Chem. Lett. 1, 117–120. DOI: 10.1007/s10311-003-0031-x.
• 19. Chiker, F., Launay, F., Nogier, J.P. & Bonardet, J.L. (2003). Green and selective epoxidation of alkenes catalysed by new TiO2-SiO2 SBA mesoporous solids. Green Chem. 5, 318–322. DOI: 10.1039/B300244F.
• 20. Wróblewska, A. (2014). The epoxidation of limonene over the TS-1 and Ti-SBA-15 catalysts, Molecules 19, 19907–19992. DOI: 10.3390/molecules191219907.
• 21. Reddy, J.S., Kumar, R. & Ratnasamy, P. (1990). Titanium silicalite-2: Synthesis, characterization and catalytic properties. Appl. Catal. A: General 58, L1–L4. DOI: 10.1016/S0166-9834(00)82273-3.
• 22. Camblor, M.A., Corma, A. & Perez-Pariente, J. (1993). Synthesis of titanoaluminosilicates isomorphous to zeolite Beta, active as oxidation catalysts. Zeolites 13, 82–87.
• 23. Grun, M., Unger, K.K., Matsumoto, A. & Tsutsumi, K. (1999). Novel pathways for the preparation of mesoporous MCM-41 materials: control of porosity and morphology. Micropor. Mesopor. Mater. 27, 207–216.
• 24. Wu, P., Tatsumi, T., Komatsu, T. & Yashima, T. (2001). A novel titanosilicate with MWW structure. I. Hydrothermal synthesis, elimination of extraframework titanium, and characterizations. J. Phys. Chem. B 105(15), 2897. DOI: 10.1021/jp002816s.
• 25. Wróblewska, A. (2008). Epoxidation of allylic compounds with hydrogen peroxide and in the presence of the titanium silicate catalyst. Szczecin, Poland: Publishing House of Technical University of Szczecin (in Polish).
• 26. Wróblewska, A. (2006). Optimization of the reaction parameters of epoxidation of allyl alcohol with hydrogen peroxide over TS-2 catalyst. Appl. Catal A: General 309, 192–200. DOI: 10.1016/j.apcata.2006.05.004.
• 27. Wróblewska, A., Fajdek, A., Wajzberg, J. & Milchert E. (2009). Epoxidation of allyl alcohol over mesoporous Ti-MCM-41 catalyst. J. Hazard. Mater. 170, 405–410. DOI: 10.1016/j.jhazmat.2009.04.082.
• 28. Wróblewska, A., Fajdek, A., Milchert, E. & Grzmil, B. (2010). The Ti-MWW catalyst – its characteristic and catalytic properties in the epoxidation of allyl alcohol by hydrogen peroxide. Pol. J. Chem. Technol. 12(1), 29–34. DOI: 10.2478/v10026-010-0006-1.
• 29. Golowa, B.M., Motowiljak, L.W., Politanskij, S.F., Stjepanow, M.W. & Czeljadin, W.T. (1974). The establishing the products in the process of glycerol obtaining during the epoxidation of allyl alcohol. Zawod. Lab. 40, 1192–1194. (in Russian).