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Environmental friendly method of the epoxidation of limonene with hydrogen peroxide over the Ti-SBA-15 catalyst

Treść / Zawartość
Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
This work presents the studies on the epoxidation of limonene to 1,2-epoxylimonene with hydrogen peroxide and over the titanium-silicate Ti-SBA-15 catalyst. The main object of the research was a solvent effect on the epoxidation process. The influence of solvents, such as: methanol, toluene, propan-2-ol (isopropyl alcohol), acetonitrile and ethanol has been studied. Furthermore, the influence of temperature in the range of 0-120°C and the reaction time in the range of 0.25-48 h have been investigated. Gas chromatography and iodometric titration methods were used to establish the products of this process and amount of the unreacted hydrogen peroxide. 1,2-Epoxylimonene, 1,2-epoxylimonene diol, perillyl alcohol, carvone and carveol have been determined as the main products of this process. All these compounds are very valuable raw materials for organic syntheses, medicine or cosmetic and food industry.
Rocznik
Strony
6--12
Opis fizyczny
Bibliogr. 29 poz., rys.
Twórcy
  • West Pomeranian University of Technology, Szczecin, Faculty of Chemical Technology and Engineering, Institute of Organic Chemical Technology, Pulaskiego 10, 70-322 Szczecin, Poland
autor
  • West Pomeranian University of Technology, Szczecin, Faculty of Chemical Technology and Engineering, Institute of Organic Chemical Technology, Pulaskiego 10, 70-322 Szczecin, Poland
autor
  • West Pomeranian University of Technology, Szczecin, Faculty of Chemical Technology and Engineering, Institute of Organic Chemical Technology, Pulaskiego 10, 70-322 Szczecin, Poland
Bibliografia
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  • 2. Nunes, L.C.C., De Almeida, A.A.C., De Carvalho, R.B.F., Cardoso, L.T., De Moraes, J.N.E., De Souza, D.P. & De Freitas, R.J. (2012). BR Patent No 102012006336.
  • 3. Yapa, A.S., Wang, H., Pyle, M., Shrestha, T.B., Troyer, D.L., Wendel, S.O. & Bossmann, S.H. (2016). Abstracts, 51st Midwest Regional Meeting of the American Chemical Society, Manhattan, KS, United States, October 26-28, 312.
  • 4. Chen, T., Levin, D. & Pupalli, S. (2016) Patent WO No US17543, PCT Int. Appl.
  • 5. De Carvalho, C.C.C.R. & Da Fonseca, M.M.R. (2006). Carvone: Why and how should one bother to produce this terpene, Food Chem. 95:413-422. DOI: 10.1016/j.foodchem.2005.01.003.
  • 6. Panda, H. (2005). The Complete Technology Book on Herbal Perfumes & Cosmetics, 234-248, Delhi : National Institute of Industrial Research.
  • 7. Nadealian, Z., Mirkhani, V., Yadollahi, B., Moghadam, M., Tangestaninejad, S. & Mohammadpoor-Baltork, I. (2013) Selective oxidation of alkenes using [BMIM]5[PW11ZNO39]3H2O hybrid catalyst. J. Iran. Chem. Soc. 10(4), 777-782.
  • 8. Wroblewska, A., Makuch, E. & Miadlicki, P. (2016). The studies on the limonene oxidation over the microporous TS-1 catalyst. Catal. Today, 268, 121-129. DOI: 10.1016/j.cattod.2015.11.008.
  • 9. Granadeiro, C.M., Barbosa, A.D.S., Ribeiro, S., Santos, I.C.M.S., De Castro, B., Cunha-Silva, L. & Balula, S.S. (2014). Oxidative catalytic versatility of a trivacant polyoxotungstate incorporated into MIL-101(Cr). Catal. Sci. Technol. 4: 1416-1425. DOI: 10.1039/C3CY00853C.
  • 10. Hua, L., Chen, J., Chen, C., Zhu, W., Yu, Y., Zhang, R., Guo, L., Song, B., Gan, H. & Hou, Z. (2014). Immobilization of polyoxometalate-based ionic liquid on carboxymethyl cellulose for epoxidation of olefins. New J. Chem. 38, 3953-3959. DOI: 10.1039/C4NJ00270A.
  • 11. Serra, S. (2015). MnO2/TBHP: A versatile and userfriend ly combination of reagents for the oxidation of allylic and benzylic methylene functional groups. Eur. J. Org. Chem. 29, 6472-6478. DOI: 10.1002/ejoc.201500829.
  • 12. Silvestre-Alberó, J., Domine, M.E., Jordá, J.L., Navarro, M.T., Reya, F., Rodríguez-Reinoso, F. & Corma, A. (2015). Spectroscopic, calorimetric, and catalytic evidences of hydrophobicity on Ti-MCM-41 silylated materials for olefin epoxidations. Appl. Catal. A, 507, 14-25. DOI: 10.1016/j.apcata.2015.09.029.
  • 13. Fernandes, C.I., Carvalho, M.D., Ferreira, L.P., Nunes, C.D. & Vaz, P.D. (2014). Organometallic Mo complex anchored to magnetic iron oxide nanoparticles as highly recyclable epoxidation catalyst. J. Organomet. Chem. 760, 2-10. DOI: 10.1016/j.jorganchem.2014.01.035.
  • 14. Tangestaninejad, S., Moghadam, M., Mirkhani, V., Mohammadpoor-Baltork, I. & Saeedi, M.S. (2010). Efficient epoxidation of alkenes with sodium periodate catalyzed by reusable manganese(III) salophen supported on multi-wall carbon nanotubes. Appl. Catal. A, 381,233-241. DOI: 10.1016/j.apcata.2010.04.013.
  • 15. Lima, L.F., Cardozo-Filho, L., Arroyo, P.A., Márquez- -Alvarez, H. & Antunes, O.A.C. (2005). Metal(salen)-catalyzed oxidation of limonene in supercritical CO2. React. Kinet. Catal. Lett. 84, 69-77. DOI: 10.1007/s11144-005-0192-7.
  • 16. Ma, B., Zhao, W., Zhang, F., Zhang, Y., Wu, S. & Ding, Y. (2014). A new halide-free efficient reaction-controlled phase-transfer catalyst based on silicotungstate of [(C18H37)2(CH3)2N]3[SiO4H(WO5)3] for olefin epoxidation, oxidation of sulfides and alcohols with hydrogen peroxide. RSC Adv. 4: 32054-32062. DOI: 10.1039/C4RA04036H.
  • 17. Santos, I.C.M.S., Gamelas, J.A.S., Duarte, T.A.G., Simoes, M.M.Q., Neves, M.G.P.M.S., Cavaleiro, J.A.S. & Cavaleiro, A.M.V. (2017). Catalytic homogeneous oxidation of monoterpenes and cyclooctene with hydrogen peroxide in the presence of sandwich-type tungstophosphates [M4(H2O)2(PW9O34)2]n−, M = CoII, MnII and FeIII. J. Mol. Catal. A: Chem. 426, 593-599. DOI: 10.1016/j.molcata.2016.10.021.
  • 18. Nunes, C.D., Vaz, P.D., Veiros, L.F., Moniz, T., Rangel, M., Realista, S., Mourato, A.C. & Calhorda, M.J. (2015). Vanadyl cationic complexes as catalysts in olefin oxidation. Dalton Trans., 44,5125-5138. DOI: 10.1039/C4DT03174A.
  • 19. Nadealian, Z., Mirkhani, V., Yadollahi, B., Moghadam, M., Tangestaninejad, S. & Mohammadpoor-Baltrok, I. (2013). Selective oxidation of alkenes using [bmim]5[PW11ZnO39]·3H2O hybrid catalyst. J. Iran. Chem. Soc. 10, 777-782. DOI: 10.1007/ s13738-012-0212-2.
  • 20. Bento, A, Sanches, A., Vaz, P.D. & Nunes, C.D. (2016) Catalytic Application of Fe-doped MoO2 Tremella-Like Nanosheets. Top. Catal. 59, 1123-1131. DOI: 10.1007/s11244-016-0631-x.
  • 21. Wróblewska, A., Makuch, E., Młodzik, J., Koren, Z.C. & Michalkiewicz, B. (2017). Fe/nanoporous carbon catalysts obtained from molasses for the limonene oxidation process. Catal. Lett. 147, 150-160. DOI: 10.1007/s10562-016-1910-7.
  • 22. Cagnoli, M.V., Casuscelli, S.G., Alvarez, A.M., Bengoa, J.F., Gallegos, N.G., Samaniego, N.M., Cribello, M.E., Ghinoe, G.E., Perez, C.F., Herrero, E.R. & Marchetti, 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.
  • 23. Wróblewska, A. (2014). The epoxidation of limonene over the TS-1 and Ti-SBA-15 catalysts. Molecules. 19, 19907-19922. DOI: 10.3390/molecules191219907.
  • 24. Berube, F., Kleitz, F. & Kaliaguine, S. (2008). A comprehensive study of titanium-substituted SBA-15 mesoporous materials prepared by direct synthesis. J. Phys. Chem. 112(37),14403-14411. DOI: 10.1021/jp803853m.
  • 25. Makuch, E. & Wróblewska, A. (2013). Preparation of titanium-silicate catalyst Ti-SBA-15. Chemik, 67,811-816.
  • 26. Wróblewska, A. & Makuch, E. (2014). Regeneration of the Ti-SBA-15 catalyst used in the process of allyl alcohol epoxidation with hydrogen peroxide. J. Adv. Oxid. Technol. 17, 44-52. DOI: 10.1515/jaots-2014-0106.
  • 27. Wróblewska, A. & Makuch, E. (2012). The utilization of Ti-SBA-15 catalyst in the epoxidation of allylic alcohols. Reac. Kinet. Mech. Cat. 105, 451-468. DOI: 10.1007/s11144-011-0405-1.
  • 28. Melero, J.A., Iglesias, J., Arsuaga, J.M., Sainz-Pardo, J., de Frutos, P. & Blazquez, S. (2007). Synthesis and catalytic activity of organic-inorganic hybrid Ti-SBA-15 materials. J. Mater. Chem. 17, 377-385. DOI: 10.1039/B610868G.
  • 29. Corma, A., Esteve, P. & Martinez, A. (1996). Solvent effects during the oxidation of olefins and alcohols with hydrogen peroxide on Ti-beta catalyst: the influence of the hydrophilicity-hydrophobicity of the zeolite. J. Catal. 161,11-19. DOI: 10.1006/jcat.1996.0157 .
Uwagi
Opracowanie rekordu w ramach umowy 509/P-DUN/2018 ze środków MNiSW przeznaczonych na działalność upowszechniającą naukę (2019).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-d07ab368-f2d9-4456-bd95-8757fe84fac7
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