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Selective Synthesis of Perillyl Alcohol from β-Pinene Epoxide over Ti and Mo Supported Catalysts

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Abstract

Isomerization of β-pinene epoxide to perillyl alcohol using several materials based on titanium and molybdenum is reported. The metals were incorporated on SBA-15, MCM-41 and SiO2 supports by incipient wetness impregnation and characterized by XRD, atomic absorption, BET, Raman spectroscopy, diffuse reflectance UV–Vis spectroscopy, TPD-NH3 and 29Si NMR. After metal incorporation, crystallinity and surface area of both MCM-41 and SBA-15 decreased. UV–Vis and Raman also revealed the presence of MoO3 species and no presence of TiO2. In addition, Ti materials showed less amount of acid sites than catalysts containing Mo. Synthesis of perillyl alcohol from β-pinene epoxide was affected by the content of acid sites; Mo/SBA-15 catalyst was more active than Mo/MCM-41 and Mo/SiO2 supported materials. Over Mo/SBA-15 a complete β-pinene epoxide conversion and perillyl alcohol selectivity of 63% were obtained at 1 h of reaction, results that are similar to the best activity reported up to now; Mo/SBA-15 can be recycled at least six times without any appreciable loss of conversion nor selectivity. Finally, a reaction pathway is proposed based on experimental information, explaining the exclusive formation of perillyl alcohol from β-pinene epoxide.

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Acknowledgements

Authors thank funding from the Ministry of Science, Technology and Innovation, the Ministry of Education, the Ministry of Industry, Commerce and Tourism and ICETEX, programme Ecosistema Científico-Colombia Científica, from the Francisco José de Caldas Fund, Grant RC-FP44842-212-2018. The authors thank also to Universidad de Antioquia for financial support. The authors thank professor Gustavo Fuentes for technical assistance in the UV–Vis, Raman and NMR characterization of the catalysts.

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Authors and Affiliations

  1. Environmental Catalysis Research Group, Chemical Engineering Department, Engineering Faculty, Universidad de Antioquia, Calle 70 No. 52-21, Medellín, Colombia

    Maria Camila Cruz, Julián E. Sánchez-Velandia, Saleth Causíl & Aída Luz Villa

  2. Centro de Investigaciones en Catálisis, Escuela de Química, Facultad de Ciencias, Universidad Industrial de Santander, Bucaramanga, Colombia

    Julián E. Sánchez-Velandia

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  1. Maria Camila Cruz
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Cruz, M.C., Sánchez-Velandia, J.E., Causíl, S. et al. Selective Synthesis of Perillyl Alcohol from β-Pinene Epoxide over Ti and Mo Supported Catalysts. Catal Lett 151, 2279–2290 (2021). https://doi.org/10.1007/s10562-020-03489-1

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