TY - JOUR
T1 - Synthesis of Florol via Prins cyclization over heterogeneous catalysts
AU - Lasne, Basile
AU - Mäki-Arvela, Päivi
AU - Aho, Atte
AU - Vajglova, Zuzana
AU - Eränen, Kari
AU - Kumar, Narendra
AU - Sánchez-Velandia, Julián E.
AU - Peurla, Markus
AU - Mondelli, Cecilia
AU - Pérez-Ramírez, Javier
AU - Murzin, Dmitry Yu
N1 - Funding Information:
Electron microscopy samples were processed and analyzed in the Electron Microscopy Laboratory, Institute of Biomedicine, University of Turku, which receives financial support from Biocenter Finland. J.E. S-V is grateful Pontificia Universidad Javeriana for the “Apoyo a Estancias Postdoctorales” (2020-2021) program.
Funding Information:
Electron microscopy samples were processed and analyzed in the Electron Microscopy Laboratory, Institute of Biomedicine, University of Turku, which receives financial support from Biocenter Finland. J.E. S-V is grateful Pontificia Universidad Javeriana for the ?Apoyo a Estancias Postdoctorales? (2020-2021) program.
Publisher Copyright:
© 2021 Elsevier Inc.
PY - 2022/1
Y1 - 2022/1
N2 - In this work, several heterogeneous micro- and mesoporous, acidic catalysts were tested for the selective synthesis of Florol®, an industrial product formed via condensation and rehydration starting from isoprenol and isovaleraldehyde in dimethylcarbonate as a solvent. The results showed that a mildly acidic, microporous H-Beta-300 with SiO2/Al2O3 ratio of 300 was the best catalyst, giving 72% selectivity with 99% conversion at 40 °C when using the molar ratio isoprenol to isovaleraldehyde of 1:5. More acidic zeolites gave slightly lower selectivity, while the lowest selectivity (up to 52%) was obtained with mesoporous catalysts exhibiting mild acidity and no strong Brønsted acid sites. Selectivity to pyranols was nearly constant when changing temperature, while a larger excess of isovaleraldehyde promoted formation of tetrahydropyranol. H-Beta-300 catalyst was successfully after calcination at 400 °C. DFT calculations pointed out on the parallel formation of tetrahydro pyranols and dihydropyrans, which are the corresponding dehydration products.
AB - In this work, several heterogeneous micro- and mesoporous, acidic catalysts were tested for the selective synthesis of Florol®, an industrial product formed via condensation and rehydration starting from isoprenol and isovaleraldehyde in dimethylcarbonate as a solvent. The results showed that a mildly acidic, microporous H-Beta-300 with SiO2/Al2O3 ratio of 300 was the best catalyst, giving 72% selectivity with 99% conversion at 40 °C when using the molar ratio isoprenol to isovaleraldehyde of 1:5. More acidic zeolites gave slightly lower selectivity, while the lowest selectivity (up to 52%) was obtained with mesoporous catalysts exhibiting mild acidity and no strong Brønsted acid sites. Selectivity to pyranols was nearly constant when changing temperature, while a larger excess of isovaleraldehyde promoted formation of tetrahydropyranol. H-Beta-300 catalyst was successfully after calcination at 400 °C. DFT calculations pointed out on the parallel formation of tetrahydro pyranols and dihydropyrans, which are the corresponding dehydration products.
KW - DFT
KW - Florol
KW - Isoprenol
KW - Isovaleraldehyde
KW - Mesoporous materials
KW - Prins cyclization
KW - Zeolites
UR - http://dx.doi.org/10.1016/j.jcat.2021.12.008
U2 - 10.1016/j.jcat.2021.12.008
DO - 10.1016/j.jcat.2021.12.008
M3 - Article
AN - SCOPUS:85121906463
SN - 0021-9517
VL - 405
SP - 288
EP - 302
JO - Journal of Catalysis
JF - Journal of Catalysis
ER -