Skip to main content
Log in

New α-pinene isomerization catalysts

  • General Review
  • Published:
Catalysis in Industry Aims and scope Submit manuscript

Abstract

Current views of the mechanism of the catalytic isomerization of α-pinene were discussed. Catalytic systems, modifiers, process conditions, and the effect of process conditions on catalytic activity and on the target-product (camphene, dipentene) selectivities of the process were considered. α-Pinene isomerization was investigated over a Belarussian natural aluminosilicate (Al-Si RB), its derivatives modified with HCl and H3PO4, modified diatomite (Al/Dia), and bentonite (ZSM-5/Ben). The commercial aluminosilicate catalyst AS-36 was used as a reference sample. Al-Si RB was treated with 10% HCl (50–250 ml/g) or 10% H3PO4 (50–100 ml/g) at 50°C for 3 h. α-Pinene was isomerized in a round-bottom flask with a backflow condenser under flowing nitrogen. The rotational speed of the stirrer was 10 rps. The highest catalytic activity and the highest camphene selectivity were observed for Al-Si RB treated with 50 ml/g of HCl. With activated Al-Si RB and As-36, 85% α-pinene conversion at 130°C and a catalyst concentration of 0.5 wt % was attained in 5.5 and 7 h, respectively. The camphene selectivity for Al-Si RB treated with 50 ml/g of HCl was 61%, being ∼20 and ∼10% higher than in the case of AS-36 and Al/Dia, respectively. Al-Si RB retained its catalytic activity for 70 h and could be fully regenerated with acetone.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Kheifits, L.A. and Dashunin, I.M., Dushistye veshchestva i drugie produkty dlya parfyumerii (Fragrances and Other Products for Perfumery), Moscow: Khimiya, 1994.

    Google Scholar 

  2. Koverninskii, I.N., Komarov, V.I., Tret’yakov, S.I., et al., Kompleksnaya khimicheskaya pererabotka drevesiny (Integrated Wood Processing), Arkhangel’sk: Arkh. Gos. Tekh. Univ., 2002.

    Google Scholar 

  3. Ryazanova, T.V., Tikhomirova, G.V., and Pochekutov, I.S., Ross. Khim. Zh., 2004, vol. 48, no. 3, p. 95.

    CAS  Google Scholar 

  4. Vyrodov, V.A., Kislitsin, A.N., and Glukhareva, M.I., Tekhnologiya lesokhimicheskikh proizvodstv (Chemical Technology of Wood), Moscow: Lesnaya Prom-st’, 1987, p. 35.

    Google Scholar 

  5. Agabekov, V.E. and Sen’kov, G.M., Katal. Promst’, 2007, no. 4, p. 38.

  6. Rudakov, G.A., Khimiya i tekhnologiya kamfary (Camphor: Chemistry and Technology), Moscow: Lesnaya Promyshlennost’, 1976, p. 42.

    Google Scholar 

  7. Tanabe, K., Katalizatory i kataliticheskie protsessy (Catalysts and Catalytic Processes), Moscow: Mir, 1993.

    Google Scholar 

  8. Lopez, C.M., Machado, F.J., Rodriguez, K., et al., Catal. Lett., 1999, vol. 62, p. 221.

    Article  CAS  Google Scholar 

  9. Masini, O., Grzona, L., Comelli, N., et al., J. Chil. Chem. Soc., 2003, no. 4, p. 48.

  10. Comelli, N.A., Ponzi, E.N., and Ponzi, M.I., Chem. Eng. J., 2006, vol. 117, no. 2, p. 93.

    Article  CAS  Google Scholar 

  11. Yadav, M.Kr., Chudasama, C.D., and Jasra, R.V., J. Mol. Catal. A: Chem., 2004, vol. 216, no. 1, p. 51.

    Article  CAS  Google Scholar 

  12. Severino, A., Esculsas, A., Rocha, J., et al., Appl. Catal., A, 1996, vol. 142, p. 255.

    Article  CAS  Google Scholar 

  13. Gündüz, G., Dimitrova, R., Yilmaz, S., et al., J. Mol. Catal. A.: Chem., 2005, vol. 225, p. 253.

    Article  Google Scholar 

  14. Volzone, C., Masini, O., Comelli, N.A., et al., Mater. Chem. Phys., 2005, vol. 93, p. 296.

    Article  CAS  Google Scholar 

  15. Hammache, S. and Goodwin, J.G., Jr., J. Catal., 2003, vol. 218, p. 258.

    Article  CAS  Google Scholar 

  16. Akpolat, O., Gündüz, G., Özkan, F., and Besün, N., Appl. Catal., A, 2004, vol. 265, no. 1, p. 11.

    Article  CAS  Google Scholar 

  17. Simakova, I.L., Solkina, Yu.S., and Moroz, B.L., et al., Appl. Catal., A, 2010, vol. 385, p. 136.

    Article  CAS  Google Scholar 

  18. Begün, N., Özkan, F., and Gündüz, G., Appl. Catal., A, 2002, vol. 224, p. 285.

    Article  Google Scholar 

  19. Özkan, F., Gündüz, G., Akpolat, O., et al., Chem. Eng. J., 2003, vol. 91, p. 257.

    Article  Google Scholar 

  20. Ward, J.W., J. Catal., 1996, p. 238.

  21. Roman-Aguirre, M., Gochi, Y., Sanchez, A., et al., Appl. Catal., A, 2008, vol. 334, nos. 1–2, p. 59.

    CAS  Google Scholar 

  22. Gündüz, G., Dimitrova, R., and Yilmaz, S., Appl. Catal., A, 2005, vol. 282, p. 61.

    Article  Google Scholar 

  23. Battalova, Sh.B. and Mukitanova, T.R., Gidroliz. Lesokhim. Promst’, 1984, no. 2, p. 8.

  24. Allahverdiev, A., Irandoust, S., and Murzin, D.Y., J. Catal., 1999, vol. 185, p. 352.

    Article  CAS  Google Scholar 

  25. Yamamoto, T., Tanaka, T., and Funabiki, T., J. Phys. Chem., 1999, vol. 103, no. 31, p. 6450.

    Article  CAS  Google Scholar 

  26. Sen’kov, G.M., Nikitina, A.M., and Agabekov, V.E., Vestsi Nats. Akad. Navuk Belarusi, Ser. Khim. Navuk, 2004, no. 4, p. 36.

  27. Startseva, L.G., Extended Abstract of Cand. Sci. (Eng.) Dissertation, Leningrad: Academy of Wood Chemistry, 1983.

    Google Scholar 

  28. Vyrodov, V.A. and Startseva, L.G., in Lesokhimiya i podsochka (Wood Chemistry and Tapping), Moscow: VNIPIEIlesprom, 1989, p. 9.

    Google Scholar 

  29. Soboleva, S.V., Extended Abstract of Cand. Sci. (Eng.) Dissertation, Krasnoyarsk: Siberian State Technol. Univ., 2001.

    Google Scholar 

  30. Ryazanova, T.V., Tikhomirova, G.V., Soboleva, S.V., and Radbil, A.B., Khim. Rastit. Syr’ya, 2000, no. 1, p. 89.

  31. Findik, S. and Gündüz, G., J. Am. Oil Chem. Soc., 1997, vol. 74, no. 9, p. 1145.

    Article  CAS  Google Scholar 

  32. Unveren, E., Gündüz, G., and Özcan, F., Chem. Eng. Commun., 2005, vol. 192, no. 3, p. 386.

    Article  Google Scholar 

  33. Ebmeyer, F., J. Mol. Struct. THEOCHEM, 2002, vol. 582, nos. 1–3, p. 251.

    Article  CAS  Google Scholar 

  34. Sen’kov, G.M., Nikitina, A.M., Gorbatsevich, M.F., et al., Vestsi Nats. Akad. Navuk Belarusi, Ser. Khim. Navuk, 2000, no. 3, p. 79; no. 4, p. 93.

  35. Sen’kov, G.M., Nikitina, A.M., and Agabekov, V.E., Trudy XV Mezhd. nauchno-tekh. konf. “Khimicheskie reaktivy, reagenty i protsessy malotonnazhnoi khimi” (Proc. XV Int. Conf. on Chemicals, Reagents, and Small-Scale Chemical Processes), Ufa, 2003, p. 12.

  36. Satterfield, Ch.N., Heterogeneous Catalysis in Practice, New York: McGraw-Hill, 1980.

    Google Scholar 

  37. Sen’kov, G.M., Nikitina, A.M., and Agabekov, V.E., Trudy XVII Mezhd. nauchno-tekh. konf. “Khimicheskie reaktivy, reagenty i protsessy malotonnazhnoi khimi” (Proc. XVII Int. Conf. on Chemicals, Reagents, and Small-Scale Chemical Processes), Ufa, 2005, vol. 2. p. 7.

    Google Scholar 

  38. Chukin, G.D., Opticheskie metody v adsorbtsii i katalize: Mater. VI Vses. shkoly-seminara (Proc. VI Workshop on Optical Methods in Adsorption and Catalysis), Alma-Ata, 1984, p. 61.

  39. Ione, K.G., Polifunktsional’nyi kataliz na tseolitakh (Polyfunctional Catalysis by Zeolites), Novosibirsk: Nauka, 1982.

    Google Scholar 

  40. Piguzova, L.I., Vysokokremnezemnye tseolity i ikh primenenie v neftepererabotke i neftekhimii (High-Silica Zeolites and Their Use in Petroleum Refining and Petroleum Chemistry), Moscow: Khimiya, 1974.

    Google Scholar 

  41. Topchieva, K.V. and Thong Kho Shi, Aktivnost’ i fizikokhimicheskie svoistva vysokokremnistykh tseolitov (Activity and Physicochemical Properties of High-Silica Zeolites), Moscow: Mosk. Gos. Univ., 1976.

    Google Scholar 

  42. Sen’kov, G.M., Nikitina, A.M., and Agabekov, V.E., Trudy XVIII Mezhd. nauchno-tekh. konf. “Khimicheskie reaktivy, reagenty i protsessy malotonnazhnoi khimi” (Proc. XVIII Int. Conf. on Chemicals, Reagents, and Small-Scale Chemical Processes), Minsk, 2005, p. 46.

  43. Arai, H. and Machida, M., Appl. Catal., A, 1996, vol. 138, p. 161.

    Article  CAS  Google Scholar 

  44. Yamamoto, T., Tanaka, T., Matsuyama, T., and Funabiki, T., Phys. Chem. Chem. Phys., 1999, vol. 1, no. 11, p. 2841.

    Article  CAS  Google Scholar 

  45. Klimanskaya, T.V., Extended Abstract of Cand. Sci. (Eng.) Dissertation, Krasnoyarsk: Siberian State Technol. Univ., 2003.

    Google Scholar 

  46. Volzone, C., Masini, O., Comelli, N., et al., Appl. Catal., A, 2001, vol. 214, p. 213.

    Article  CAS  Google Scholar 

  47. Sen’kov, G.M., Nikitina, A.M., and Agabekov, V.E., Trudy XXI Mezhd. nauchno-tekh. konf. “Khimicheskie reaktivy, reagenty i protsessy malotonnazhnoi khimi” (Proc. XXI Int. Conf. on Chemicals, Reagents, and Small-Scale Chemical Processes), Ufa, 2008, vol. 1, p. 58.

    Google Scholar 

  48. Sen’kov, G.M., Sidorenko, A.Yu., and Agabekov, V.E., Trudy XXII Mezhd. nauchno-tekh. konf. “Khimicheskie reaktivy, reagenty i protsessy malotonnazhnoi khimi” (Proc. XXII Int. Conf. on Chemicals, Reagents, and Small-Scale Chemical Processes), Ufa, 2009, p. 75.

  49. Sidorenko, A.Yu., Sen’kov, G.M., and Agabekov, V.E., IV Vserossiiskaya konferentsiya “Khimiya i polnaya pererabotka biomassy lesa” (IV Russian Conf. on Chemistry and Total Processing of Wood Biomass), St. Petersburg, 2010, p. 94.

  50. Sen’kov, G.M., Nikitina, A.M., Agabekov, V.E., Bondarenko, S.N., Kozlov, N.G., and Shkarubo, V.V., Belarussian Patent 12925, 2009.

  51. Allakhverdiev, A.I., Sokolova, N.A., and Gunduz, G., Russ. J. Phys. Chem., 1998, vol. 72, no. 10, p. 1816.

    CAS  Google Scholar 

  52. Ecormier, M.A., Wilson, K., and Lee, A.F., J. Catal., 2003, vol. 215, no. 1, p. 57.

    Article  CAS  Google Scholar 

  53. Grzona, L., Comelli, N., Masini, O., et al., React. Kinet. Catal. Lett., 2000, vol. 69, no. 2, p. 271.

    Article  CAS  Google Scholar 

  54. Comelli, N.A., Ponzi, E.N., and Ponzi, M.I., J. Am. Oil Chem. Soc., 2005, vol. 82, no. 7, p. 531.

    Article  CAS  Google Scholar 

  55. Komarov, V.S. and Rat’ko, A.I., Adsorbenty: poluchenie, struktura, svoistva (Adsorbents: Preparation, Structure, and Properties), Minsk: Belarus. Nauka, 2009, p. 88.

    Google Scholar 

  56. Magaril, R.Z., Teoreticheskie osnovy khimicheskikh protsessov pererabotki nefti (Theoretical Foundations of Petroleum Refining), Moscow: Knizhnyi Dom “Universitet,” 2008, p. 186.

    Google Scholar 

  57. Battalova, Sh.B., Mukitanova, T.R., and Dzhakisheva, R.D., Izv. Akad. Nauk Kaz. SSR, 1977, no. 2, p. 71.

  58. Tishchenko, V.E. and Rudakov, G.A., Zh. Prikl. Khim., 1933, vol. 6, no. 4, p. 698.

    Google Scholar 

  59. Comelli, N., Grzona, L., Masini, O., et al., J. Chil. Chem. Soc., 2004, vol. 49, no. 3, p. 245.

    Article  CAS  Google Scholar 

  60. Rudin, M.G. and Drabkin, A.E., Kratkii spravochnik neftepererabotchika (Petroleum Refiner’s Concise Handbook), Leningrad: Khimiya, 1980, p. 322.

    Google Scholar 

  61. Sen’kov, G.M., Nikitina, A.M., and Agabekov, V.E., Trudy XX Mezhd. nauchno-tekh. konf. “Khimicheskie reaktivy, reagenty i protsessy malotonnazhnoi khimi” (Proc. XX Int. Conf. on Chemicals, Reagents, and Small-Scale Chemical Processes), Minsk, 2007, p. 92.

  62. Radbil, A.B., Extended Abstract of Doctoral (Eng.) Dissertation, Krasnoyarsk: Siberian State Technol. Univ., 2009.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Original Russian Text © V.E. Agabekov, G.M. Sen’kov, A.Yu. Sidorenko, Nguyen Dinh Tuyen, Vu Anh Tuan, 2011, published in Kataliz v Promyshlennosti.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Agabekov, V.E., Sen’kov, G.M., Sidorenko, A.Y. et al. New α-pinene isomerization catalysts. Catal. Ind. 3, 319–330 (2011). https://doi.org/10.1134/S2070050411040027

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S2070050411040027

Keywords

Navigation