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A Kinetic Study of the Liquid Phase Acetoxylation of α-Pinene

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Abstract

The present study introduces kinetic modeling of liquid phase α-pinene acetoxylation with acetic acid over an ion-exchange resin catalyst. The reaction was carried out in a laboratory scale high-pressure autoclave. α-terpinyl (35 wt%) and bornyl (40 wt%) acetates were the primary products. The predominant reaction pathways were identified and evaluated.

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References

  1. Corma A, Iborra S, Velty A (2007) Chem Rev 107:2411–2502

    Article  CAS  Google Scholar 

  2. Erman WE (1985) Chemistry of the monoterpenes, an encyclopedic handbook. Marcel Dekker, New York

    Google Scholar 

  3. Gainsford GJ, Hosie CF, Weston RJ (2001) Appl Catal A: Gen 209:269–277

    Article  CAS  Google Scholar 

  4. Izak P, Mateus NMM, Afonso CAM, Crespo JG (2005) Sep Purif Tech 41:141–145

    Article  CAS  Google Scholar 

  5. Liu S, Xie C, Yu S, Liu F, Ji K (2008) Catal Comm 9:1634–1638

    Article  CAS  Google Scholar 

  6. Mäki-Arvela P, Holmbom B, Salmi T, Murzin DY (2007) Catal Rev 49:197–340

    Article  Google Scholar 

  7. Monteiro JLF, Veloso CO (2004) Catalytic conversion of terpenes into fine chemicals. Top Catal 27:1–4

    Article  Google Scholar 

  8. Muller P, Lamparsky D (1991) Perfumes, art, science and technology. Elsevier Applied Science, New York, NY

    Book  Google Scholar 

  9. Cao W, Li F, Li X, Yiang L (1995) Huaxue Yu Nianhe l:14

    Google Scholar 

  10. Hensen K, Mahaim C, Holderich WF (1997) Appl Catal A: Gen 149:311–329

    Article  CAS  Google Scholar 

  11. Nomura M, Kyouda M, Fujihara Y, Tajima K, Otani T (1994) Yukagaku 43:1089

    CAS  Google Scholar 

  12. Xiao S, Jiang W, Zhou P (1989) Linchan Huaxue Yu Gongye 9(2):9

    CAS  Google Scholar 

  13. Zhou P, Jiang W, Guo Y, Chen X, Xiao S (1989) Chin Sci Bull 34(2):125

    CAS  Google Scholar 

  14. Yadav MK, Patil MV, Jasra RV (2009) J Mol Catal A: Chem 297:101–109

    Article  CAS  Google Scholar 

  15. Matsubara Y, Tanaka K, Urata M, Fukunaga T, Kuwata M, Takahashi K, Nippon Kagaku Kaishi, 1975, 855 (Chem Abstr, 1976, 84, 180398)

  16. Nomura M, Fujihara Y, Nippon Kagaku Kaishi, 1983, 1818 (Chem Abstr, 1984, 100, 192083)

  17. Tan Q, Day DF, Cadwallader KR (1998) Proc Biochem 33:29

    Article  CAS  Google Scholar 

  18. Robles-Dutenhefner PA, da Silva KA, Siddiqui MRH, Kozhevnikov IV, Gusevskaya EV (2001) J Mol Catal A: Chem 175:33–42

    Article  CAS  Google Scholar 

  19. Gusevskaya E, Robles-Dutenhefner PA, Ferreira VMS (1998) Appl Catal A: Gen 174:177–186

    Article  CAS  Google Scholar 

  20. Chandak HS, Lad NP, Dange DS (2012) Greener and facile aqueous synthesis of pyrazoles using Amberlyst-70 as a recyclable catalyst. Green Chem Lett Rev 5:135–138

    Article  CAS  Google Scholar 

  21. Spivey AvjJ (1999) Catalysis, vol 14. Chemical Society (Great Britain), Royal Society of Chemistry (Great Britain)

  22. Chimal-Valencia O, Robau-Sanchez A, Collins-Martinez V, Aguilar-Elgueezabal A (2004) Ion exchange resins as catalyst for the isomerization of a-pinene to camphene. Biores Tech 93:119–123

    Article  CAS  Google Scholar 

  23. Orjuela A, Yanez AJ, Santhanakrishnan A, Lira CT, Miller DJ (2012) Kinetics of mixed succinic acid/acetic acid esterification with Amberlyst 70 ion exchange resin as catalyst. Chem Eng J 188:98–107

    Article  CAS  Google Scholar 

  24. Xu ZP, Chuang KT (1997) Chem Eng Soc 52(17):3011

    Article  CAS  Google Scholar 

  25. Haario H (2001) Modest 6.0 A. User’s Guide, Prof. Math Helsinki

Download references

Acknowledgments

Umeå University Business Graduate School, Processum Biorefinery Initiative AB, Aditya Birla Domsjö Fabriker, Holmen Energi AB, MoRe Research and M-real Husum are gratefully acknowledged for the financial support. The Bio4Energy program is acknowledged. Rohm and Haas Nordic representative is gratefully acknowledged for providing the catalyst samples.

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Authors and Affiliations

  1. Technical Chemistry, Department of Chemistry, Chemical-Biological Center, Umeå University, 90187, Umeå, Sweden

    M. Golets, S. Ajaikumar, W. Larsson & J.-P. Mikkola

  2. Processum Biorefinery Initiative AB, 89186, Örnsköldsvik, Sweden

    D. Blomberg

  3. Aditya Birla Domsjö Fabriker AB, 89186, Örnsköldsvik, Sweden

    H. Grundberg

  4. Laboratory of Industrial Chemistry and Reaction Engineering, Process Chemistry Centre, Åbo Akademi University, Biskopsgatan 8, 20500, Turku, Finland

    J. Wärnå, T. Salmi & J.-P. Mikkola

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  1. M. Golets
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  2. S. Ajaikumar
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  3. W. Larsson
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  4. D. Blomberg
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  6. J. Wärnå
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  7. T. Salmi
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  8. J.-P. Mikkola
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Correspondence to M. Golets or J.-P. Mikkola.

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Golets, M., Ajaikumar, S., Larsson, W. et al. A Kinetic Study of the Liquid Phase Acetoxylation of α-Pinene. Top Catal 55, 649–656 (2012). https://doi.org/10.1007/s11244-012-9844-9

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